U.S. patent application number 09/930790 was filed with the patent office on 2002-09-26 for 1 - (3-heterocyclylphenyl) isothiourea, -isourea, -guanidine and -amidine herbicidal agents.
This patent application is currently assigned to Intellectual Property Department, BASF Aktiengesellschaft. Invention is credited to Karp, Gary M..
Application Number | 20020137929 09/930790 |
Document ID | / |
Family ID | 26791724 |
Filed Date | 2002-09-26 |
United States Patent
Application |
20020137929 |
Kind Code |
A1 |
Karp, Gary M. |
September 26, 2002 |
1 - (3-heterocyclylphenyl) isothiourea, -isourea, -guanidine and
-amidine herbicidal agents
Abstract
There are provided 1-(3-heterocyclyphenyl)isothiourea, -isourea,
-guanidine and -amidine compounds of formula I 1 Further provided
are compositions and methods comprising those compounds for the
control of undesirable plant species.
Inventors: |
Karp, Gary M.; (Princeton
Junction, NJ) |
Correspondence
Address: |
BASF Corporation
Patent Law Department
P.O. Box 400
Princeton
NJ
08543-0400
US
|
Assignee: |
Intellectual Property Department,
BASF Aktiengesellschaft
Carl-Bosch-Strasse 38
Ludwigshafen
DE
D-67056
|
Family ID: |
26791724 |
Appl. No.: |
09/930790 |
Filed: |
August 16, 2001 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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09930790 |
Aug 16, 2001 |
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09368340 |
Aug 4, 1999 |
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6303783 |
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60096448 |
Aug 13, 1998 |
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Current U.S.
Class: |
544/60 ; 544/133;
544/367; 546/209; 548/117 |
Current CPC
Class: |
C07D 211/88 20130101;
C07D 239/54 20130101; A01N 43/74 20130101; C07D 209/48 20130101;
C07D 417/12 20130101; C07D 403/12 20130101; C07D 417/14 20130101;
C07D 249/12 20130101; C07D 413/12 20130101; C07D 405/12
20130101 |
Class at
Publication: |
544/60 ; 544/133;
544/367; 546/209; 548/117 |
International
Class: |
C07D 417/02 |
Claims
What is claimed is:
1. A compound having the structural formula I 144wherein X and Y
are each independently hydrogen, halogen, nitro, cyano,
C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl or
S(O).sub.mR.sub.1; R is hydrogen, a C.sub.1-C.sub.8alkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.8alkenyl,
C.sub.5-C.sub.7-cycloalkenyl or C.sub.3-C.sub.8alkynyl group,
wherein each group is optionally substituted with any combination
of one to six halogen atoms, one or two cyano groups, one or two
nitro groups, one or two C(W)R.sub.2 groups, one or two
C(W)OR.sub.3 groups, one or two C(W)NR.sub.4R.sub.5 groups, one or
two P(V) (OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one
or two SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups, one or
two OC(W)R.sub.11 groups, one or two NR.sub.12S(O).sub.nR.sub.13
groups, one or two C(W)NR.sub.12S(O).sub.nR.s- ub.13 groups, one 4-
to 10-membered heterocyclic ring option-ally substituted with any
combination of one or two oxo groups, one or two thioxo groups, one
to three halogen atoms, one to three nitro groups, one to three
cyano groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxy- alkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonyalkyl groups, one to three
C.sub.3-C.sub.6haloalkyl-carbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups, or one phenyl group
optionally substituted with any combination of one to three halogen
atoms, one to three nitro groups, one to three cyano groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups,-one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two C.sub.2-C.sub.6-
haloalkoxyalkyl groups, one or two C(O)OR.sub.14 groups, one or two
C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonyl-alkyl groups, one to three
C.sub.3-C.sub.6haloalkyl-carbonylalkyl groups one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups, a 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one or two oxo groups, one or two thioxo groups, one to three
halogen atoms, one to three nitro groups, one to three cyano
groups, one to three C.sub.1-C.sub.4-alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxy-- alkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxy-carbonylalkyl groups, one to three
C.sub.3-C.sub.6halo-alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6-alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6-haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups, phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three nitro groups, one to three cyano groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4-haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups,
OR.sub.17,NR.sub.18R.sub.19,NR.sub.20S(O).sub.qR.sub.21,NR-
.sub.22C(V)R.sub.23,NR.sub.24P(V)(OR.sub.25).sub.2,
C(V)NR.sub.20S(O).sub.qR.sub.21,cyano,S(O).sub.qR.sub.26,P(V)(OR.sub.27).-
sub.2,C (V) R.sub.28 or C(V) OR.sub.29; W is O, S, NR.sub.30,
NOR.sub.31 or NNR.sub.32R.sub.33; V and Z are each independently O
or S; R.sub.1 and R.sub.14 are each independently
C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4haloalkyl; R.sub.2 is
hydrogen, C.sub.2-C.sub.6alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6-alkoxyalk- yl,
C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxy-carbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two C.sub.2-C.sub.6-
alkoxyalkyl groups, one or two C.sub.2-C.sub.6haloalkoxy- -alkyl
groups, one or two nitro groups, one or two cyano groups, one
NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxy-carbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one C.sub.3-C.sub.6-
alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylca- rbonylalkyl group, a 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one or two oxo groups, one or two thioxo groups, one to three
halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxy-alkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyalkyl groups, one or two nitro groups, one
or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxy-carbonyl group, one
C.sub.2-C.sub.6alkylcarbony- l group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-- carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group, C.sub.1-C.sub.4alkyl
substituted with one phenyl group wherein the phenyl group is
optionally substituted with any combination of one to three halogen
atoms, one or two nitro groups, one or two cyano groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or C.sub.1-C.sub.4alkyl
substituted with one 4- to 10-membered heterocyclic ring wherein
the heterocyclic ring is optionally substituted with any
combination of one to three halogen atoms, one or two nitro groups,
one or two cyano groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.3 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cyclo-alky- l, C.sub.3-C.sub.6alkenyl
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalk- yl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, furfural optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or an alkali metal, alkaline
earth metal, manganese, copper, zinc, cobalt, silver, nickel,
ammonium or organic ammonium cation; R.sub.4 and R.sub.5 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.1-C.sub.6alkoxy, hydroxy, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6haloalkoxycarbonylalky- l,
C.sub.2-C.sub.6hydroxy-carbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl- ,
C.sub.2-C.sub.6halo-alkylsulfonylalkyl, S(O).sub.pR.sub.16, phenyl
optionally substituted with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, provided that only one of R.sub.4
and R.sub.5 can be hydroxy or C.sub.1-C.sub.6alkoxy, and when
R.sub.4 and R.sub.5 are taken together with the atom to which they
are attached, they represent a three- to seven-membered saturated
or unsaturated ring optionally interrupted by oxygen, sulfur or
nitrogen, and optionally substituted with one to three methyl
groups or one or more halogen atoms; R.sub.6, R.sub.25 and R.sub.27
are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, phenyl optionally substituted with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.7,
R.sub.8 and R.sub.17 are each independently hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.2-C.sub.6haloalkoxyalkyl, C.sub.2-C.sub.6alkylcarbonylalkyl,
C.sub.2-C.sub.6haloalkylcarbonylalkyl,
C.sub.2-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6haloalkoxycarbonylalky- l,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalky- l,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C(V)NR.sub.12S(O).sub.nR.sub.13, phenyl optionally substituted with
any combination of one to three halogen atoms, one or two cyano
groups, one or two nitro groups, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.9, R.sub.10, R.sub.18,
R.sub.19, R.sub.32 and R.sub.33 are each independently hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6halo-alkylcarbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6-haloalkoxycarbonylal- kyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalky- l,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4 haloalkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and when R.sub.9 and R.sub.10 or
R.sub.18 and R.sub.19 or R.sub.32 and R.sub.33 are taken together
with the atom to which they are attached, they represent a three-
to seven-membered saturated or unsaturated ring optionally
interrupted by oxygen, sulfur or nitrogen, and optionally
substituted with one to three methyl groups or one or more halogen
atoms; R.sub.1, is hydrogen, C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.7cyclo-alky- l,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxy-alkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkyl-carbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6halo-alkoxycarbonylal- kyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4 haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.12, R.sub.15, R.sub.20 and
R.sub.24 are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6alkenyl or
C.sub.3-C.sub.6alkynyl; R.sub.13, R.sub.21, R.sub.22, R.sub.23,
R.sub.26, R.sub.28 and R.sub.29 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6haloalkoxycarbonylalk- yl, phenyl optionally
substituted with any combination of one to three
halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxya- lkyl groups, one or two nitro groups,
one or two cyano groups, one C.sub.3-C.sub.6alkoxy-carbonylalkyl
group, one C.sub.3-C.sub.6haloalkoxy-- carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group or one
C.sub.2-C.sub.6hydroxycarbonylalkyl group, a 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxy- alkyl groups, one or two nitro groups,
one or two cyano groups, one C.sub.3-C.sub.6alkoxy-carbonylalkyl
group, one C.sub.3-C.sub.6haloalkoxy-- carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group or one
C.sub.2-C.sub.6hydroxycarbonylalkyl group, benzyl optionally
substituted on the phenyl ring with any combination of one to three
halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.16
is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cyclo-alkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalky- l,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl, phenyl optionally
substituted on the phenyl ring with any combination of one to three
halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
furfural optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.30 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cyclo-alkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one C.sub.2-C.sub.6alkoxy-alkyl
group, one C.sub.2-C.sub.6haloalkoxyalkyl group, one
NR.sub.15S(O).sub.nR.sub.16 group, one C.sub.2-C.sub.6alkoxyca-
rbonyl group, one C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6alkyl-carbo- nylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group or one
C.sub.3-C.sub.6haloalkyl-carbonylalkyl group, a 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one C.sub.2-C.sub.6alkoxyalkyl
group, one C.sub.2-C.sub.6haloalkoxyalkyl group, one
NR.sub.15S(O).sub.nR.sub.16 group, one C.sub.2-C.sub.6alkoxyca-
rbonyl group, one C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6alkyl-carbo- nylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group or one
C.sub.3-C.sub.6haloalkyl-carbonylalkyl group, benzyl optionally
substituted on the phenyl ring with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4, haloalkoxy groups, or
furfural optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.31
is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.2-C.sub.6haloalkoxyalkyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6haloalkoxycarbonylalk- yl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalk- yl,
C.sub.2-C.sub.6hydroxy-carbonylalkyl,
C(V)NR.sub.12S(O).sub.nR.sub.13, phenyl optionally substituted with
any combination of one to three halogen atoms, one or two cyano
groups, one or two nitro groups, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, a 4- to 10-membered heterocyclic
ring optionally substituted with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; A is --O--, --S(O).sub.r--,
--NR.sub.34-- or --CR.sub.35R.sub.36--; B is
--CR.sub.37R.sub.38(CR.sub.39R.sub.40).sub.s--, --C (.dbd.T)-- or
--C(.dbd.CR.sub.41R.sub.42)--; R.sub.34, R.sub.35, R.sub.36,
R.sub.37, R.sub.38, R.sub.39 and R.sub.40 are each independently
hydrogen, halogen, C.sub.1-C.sub.6alkyl optionally substituted with
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one or two C(W)R.sub.2 groups, one or two
C(W)OR.sub.3 groups, one or two C(W)NR.sub.4R.sub.5 groups, one or
two P(V)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or
two SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups or one or
two OC(W)R.sub.21.sup.- groups, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C(V)NR.sub.12S(O).sub.nR.sub.13, phenyl optionally substituted with
any combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxya- lkyl groups, one or two nitro groups,
one or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6halo-alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one C.sub.3-C.sub.6
alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6halo-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6alkyl-carbonylalkyl group or one
C.sub.3-C.sub.6haloalkyl-- carbonylalkyl group, a 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxy-alkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyalkyl groups, one or two nitro groups, one
or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxy-carbonyl group, one
C.sub.2-C.sub.6alkylcarbony- l group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-- carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group, C.sub.1-C.sub.4alkyl
substituted with one phenyl group wherein the phenyl group is
optionally substituted with any combination of one to three halogen
atoms, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxy-carbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbon- yl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6-haloalkylcarbonyl group, one
C.sub.3-C.sub.6alkoxy-carbon- ylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarb- onylalkyl group, one
C.sub.3-C.sub.8alkoxycarbonylalkoxy group or one
C.sub.2-C.sub.8hydroxycarbonylalkoxy group, or C.sub.1-C.sub.4alkyl
substituted with one 4- to 10-membered heterocyclic ring wherein
the heterocyclic ring is optionally substituted with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxya- lkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxyca- rbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6-haloalkylcarbonylalkyl group, and when R.sub.35 and
R.sub.36 or R.sub.37 and R.sub.38 or R.sub.39 and R.sub.40 are
taken together with the atom to which they are attached, they
represent a ring in which R.sub.35R.sub.36, or R.sub.37R.sub.38 or
R.sub.39R.sub.40 is a C.sub.2-C.sub.6alkylene group; T is O, S,
NR.sub.30, NOR.sub.31 or NNR.sub.32R.sub.33; R.sub.41 and R.sub.42
are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.1-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl,
C.sub.2-C.sub.6-alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl,
hydroxy-carbonyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6halo-alkoxycarbonylalk- yl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl- ,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups or one
C.sub.3-C.sub.8-alkoxycarbonylalkoxy group, benzyl optionally
substituted on the phenyl ring with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
furfural optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and when
R.sub.41 and R.sub.42 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring option-ally interrupted with one
group selected from O, S(O).sub.r or NR.sub.31, and optionally
substituted with one to three methyl groups or one or more halogen
atoms; m and r are each independently an integer of 0, 1 or 2; n, p
and q are each independently an integer of 1 or 2; s is an integer
of 0 or 1; Q is selected from 145D and D.sub.1 are each
independently O or S; E is hydroxy, halogen, C.sub.1-C.sub.4alkoxy
or C.sub.1-C.sub.4alkylthio; R.sub.43 and R.sub.44 are each
independently hydrogen, halogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyi, C.sub.3-C.sub.7acycloalky- l,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, cyano, amino, hydroxy or benzyl, and when
R.sub.43 and R.sub.44 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted by oxygen,
sulfur or nitrogen, and optionally substituted with one to three
methyl groups or one or more halogen atoms; R.sub.45 and R.sub.46
are each independently hydrogen, halogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, OR.sub.51, S(O).sub.tR.sub.52 or
NR.sub.53R.sub.54, and when R.sub.45 and R.sub.46 are taken
together with the atom to which they are attached, they represent a
three- to seven-membered saturated or unsaturated ring optionally
interrupted by oxygen, sulfur or nitrogen, and optionally
substituted with one to three methyl groups or one or more halogen
atoms; R.sub.47, R.sub.49 and R.sub.50 are each independently
hydrogen, halogen or C.sub.1-C.sub.6alkyl; R.sub.48 is hydrogen,
halogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.1-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl, OR.sub.51 or
SR.sub.52; R.sub.51 and R.sub.52 are each independently hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl,
C.sub.1-C.sub.7cycloalkyl, C.sub.1-C.sub.4cyanoalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, benzyl or phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.53 is hydrogen,
C.sub.1-C.sub.4alkyl, benzyl or phenyl optionally substituted with
any combination of one to three halogen atoms, one or two cyano
groups, one or two nitro groups, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.54 in hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.7cyclo-alkyl, benzyl, S(O).sub.tR.sub.52 or phenyl
optionally substituted with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; and t is
an integer of 0, 1 or 2; and
the agriculturally acceptable salts thereof.
2. The compound according to claim 1 wherein X is hydrogen or
halogen; Y is hydrogen, halogen, nitro or cyano; R is hydrogen, a
C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.8alkenyl, C.sub.5-C.sub.7cycloalkenyl or
C.sub.3-C.sub.8alkynyl group, wherein each group is optionally
substituted with any combination of one to six halogen atoms, one
or two cyano groups, one or two nitro groups, one or two
C(O)R.sub.2 groups, one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups, one or two SR.sub.8 groups, one or two
NR.sub.9R.sub.10 groups, one or two OC(O)R.sub.11 groups, one or
two NR.sub.12S(O).sub.nR.sub.13 groups, one or two
C(O)NR.sub.12S(O).sub.nR.s- ub.13 groups, one 4- to 10-membered
heterocyclic ring optionally substituted with any combination of
one or two oxo groups, one or two thioxo groups, one to three
halogen atoms, one to three nitro groups, one to three cyano
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6lalkoxyalkyl groups, one or two
C.sub.2-C.sub.6-haloalkoxy- alkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonyalkyl groups, one to three
C.sub.3-C.sub.6haloalkyl-carbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(O)NR.sub.15S(O).sub.pR- .sub.16 groups, or one phenyl group
optionally substituted with any combination of one to three halogen
atoms, one to three nitro groups, one to three cyano groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6- alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(O)NR.sub.15S(O).sub.pR- .sub.16 groups, phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three nitro groups, one to three cyano groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4-haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups or one or two
NR.sub.15S(O).sub.pR.sub.1, groups, OR.sub.17, NR.sub.18R.sub.19,
NR.sub.20S(O).sub.qR.sub.21, NR.sub.22C(O)R.sub.23, C(O)NR.sub.20S
(O).sub.qR.sub.21, S(O).sub.qR.sub.26, C(O)R.sub.28 or
C(O)OR.sub.29; Z is O; R.sub.14 is C.sub.1-C.sub.4alkyl or
C.sub.1-C.sub.4haloalkyl; R.sub.2 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, or phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two C.sub.2-C.sub.6alkoxyalkyl
groups, one C.sub.2-C.sub.6alkoxyca- rbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6haloalkoxycarbonylalkyl group; R.sub.3 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cyclo-alky- l, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyal- kyl,
C.sub.2-C.sub.6haloalkoxyalkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
phenyl optionally substituted with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, furfural optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or an alkali metal, alkaline
earth metal, manganese, copper, zinc, cobalt, silver, nickel,
ammonium or organic ammonium cation; R.sub.4 and R.sub.5 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.1-C.sub.6alkoxy, hydroxy,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, S(O).sub.pR.sub.16, phenyl
optionally substituted with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, provided that only one of R.sub.4
and R.sub.5 can be hydroxy or C.sub.1-C.sub.6alkoxy, and when
R.sub.4 and R.sub.5 are taken together with the atom to which they
are attached, they represent a three- to seven-membered saturated
or unsaturated ring optionally interrupted by oxygen, sulfur or
nitrogen, and optionally substituted with one to three methyl
groups or one or more halogen atoms; R.sub.6 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.7
and R.sub.8 are each independently hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxy-carbonylalky- l; R.sub.17 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-C.sub.6alkoxyalky- l, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.2-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl- ,
C.sub.2-C.sub.6hydroxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.9
and R.sub.10 are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6alkylcarbonylalkyl,
C.sub.1-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl, or phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and when R.sub.9 and R.sub.10 are
taken together with the atom to which they are attached, they
represent a three- to seven-membered saturated or unsaturated ring
optionally interrupted by oxygen, sulfur or nitrogen, and
optionally substituted with one to three methyl groups or one or
more halogen atoms; R.sub.10 and R.sub.19 are each independently
hydrogen, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6al
koxycarbonylalkyl, C.sub.3-C.sub.6haloalkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylalk- yl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalk- yl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the phenyl ring with any combination of one to three halogen atoms,
one or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and when R.sub.18 and R.sub.19
are taken together with the atom to which they are attached, they
represent a three- to seven-membered saturated or unsaturated ring
optionally interrupted by oxygen, sulfur or nitrogen, and
optionally substituted with one to three methyl groups or one or
more halogen atoms; R.sub.11 is hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.1-C.sub.6haloalkyl; R.sub.12, R.sub.15 and R.sub.20 are each
independently hydrogen or C.sub.1-C.sub.6alkyl; R.sub.13, R.sub.16,
R.sub.21 and R.sub.26 are each independently C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.22 is hydrogen or
C.sub.1-C.sub.6alkyl; R.sub.23 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cyclo-alky- l,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkyl-carbonylalk- yl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6halo-alkoxycarbonyl- alkyl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three C.sub.1-C.sub.4-
haloalkoxy groups; R.sub.28 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7-cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6alkoxy-carbonylalkyl, or phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.29
is hydrogen, C.sub.1-C.sub.6alkyl or benzyl; A is --O--,
--S(O).sub.r--, or --NR.sub.34--; B is --CR.sub.37R.sub.38--,
--C(O)-- or --C(.dbd.CR.sub.41R.sub.42)--; R.sub.34 is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one or two C(O)R.sub.2 groups, one or two C(O)OR.sub.3 groups, one
or two C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2
groups, one or two OR.sub.7 groups, one or two SR.sub.8 groups, one
or two NR.sub.9R.sub.10 groups or one or two OC(O)R.sub.11 groups,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C(O)NR.sub.12S(O).sub.nR.sub.13, phenyl
optionally substituted with any combination of one to three halogen
atoms, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalk- yl group or one
C.sub.3-C.sub.6alkyl-carbonylalkyl group, or C.sub.1-C.sub.4alkyl
substituted with one phenyl group wherein the phenyl group is
optionally substituted with any combination of one to three halogen
atoms, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, groups, one
C.sub.2-C.sub.6alkoxy-car- bonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6-alkylcarb- onylalkyl group; R.sub.37 and R.sub.38
are each independently hydrogen, halogen, C.sub.1-C.sub.6alkyl
optionally substituted with one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one or two C(O)R.sub.2
groups, one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups, one or two SR.sub.8 groups, one or two
NR.sub.9R.sub.10 groups or one or two OC(O)R.sub.11 groups,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C(O)NR.sub.12S(O).sub.nR.sub.13, phenyl
optionally substituted with any combination of one to three halogen
atoms, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalky- l group or one
C.sub.3-C.sub.6alkylcarbonylalkyl group, or C.sub.1-C.sub.4alkyl
substituted with one phenyl group wherein the phenyl group is
optionally substituted with any combination of one to three halogen
atoms, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxy-carbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6-alkylcarb- onylalkyl group, and when R.sub.37 and
R.sub.38 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.37R.sub.38 is a
C.sub.2-C.sub.6alkylene group; R.sub.41 and R.sub.42 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl,
hydroxy-carbonyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxy-carbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, benzyl optionally substituted on
the
phenyl ring with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or furfural optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and when R.sub.41 and R.sub.42
are taken together with the atom to which they are attached, they
represent a three- to seven-membered saturated or unsaturated ring
optionally interrupted with one group selected from O, S(O).sub.r
or NR.sub.31, and optionally substituted with one to three methyl
groups or one or more halogen atoms; r is an integer of 0, 1 or 2;
n, p and q are each independently an integer of 1 or 2; Q is
selected from 146D and D.sub.1 are each independently O or S;
R.sub.43 and R.sub.44 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl, amino, or
benzyl; R.sub.45 and R.sub.46 are each independently hydrogen,
halogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl or C.sub.3-C.sub.6alkynyl, and when
R.sub.45 and R.sub.46 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted by oxygen,
sulfur or nitrogen, and optionally substituted with one to three
methyl groups or one or more halogen atoms; and R.sub.47 and
R.sub.48 are each independently hydrogen, halogen or
C.sub.1-C.sub.6alkyl.
3. The compound according to claim 2 wherein X is hydrogen,
fluorine or chlorine; Y is fluorine, chlorine, nitro or cyano; R is
hydrogen, C.sub.1-C.sub.8alkyl optionally substituted with any
combination of one to six halogen atoms, one or two cyano groups,
one or two nitro groups, one or two C(O)R.sub.2 groups, one or two
C(O) OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two P(O)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or
two SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups, one or two
C(O)NR.sub.12S(O).sub.nR.sub.13 groups, one furyl group optionally
substituted with any combination of one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one or two C(O)OR.sub.14 groups or one or two C(O)R.sub.14
groups, one pyridyl group optionally substituted with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups, one or two C(O)OR.sub.14 groups
or one or two C(O)R.sub.14 groups, or one phenyl group optionally
substituted with any combination of one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one or two C(O)OR.sub.14 groups or one or two C(O)R.sub.14
groups, phenyl optionally substituted with any combination of one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two C.sub.2-C.sub.6alkoxyalkyl
groups, one or two C(O)OR.sub.14 groups, one or two C(O)R.sub.14
groups, one to three C.sub.3-C.sub.6alkoxycarbonylalkyl groups or
one or two NR.sub.15S(O).sub.pR.sub.16 groups,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.8alkenyl,
C.sub.3-C.sub.8alkynyl, OR.sub.17, NR.sub.18R.sub.19, C(O)R.sub.28
or C(O)QOR.sub.29; Z is O; R.sub.14 is C.sub.1-C.sub.4alkyl;
R.sub.2 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.2-C.sub.6alkoxyalkyl or C.sub.3-C.sub.6-alkoxycarbonylalkyl;
R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalky- l,
C.sub.2-C.sub.6haloalkoxyalkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
phenyl optionally substituted with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4-haloalkoxy groups; R.sub.4 and R.sub.5 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.6alkoxycarbon- ylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4halo-alkoxy groups, and when
R.sub.4 and R.sub.5 are taken together with the atom to which they
are attached, they represent a ring in which R.sub.4R.sub.5 is a
C.sub.2-C.sub.6alkylene group; R.sub.6 is hydrogen,
C.sub.1-C.sub.6alkyl or benzyl; R.sub.7 and R.sub.8 are each
independently hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxy-carbonylalkyl; R.sub.17 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6-hydroxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.9
and R.sub.10 are each independently hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.3-C.sub.6alkoxycarbonylalkyl, and when R.sub.9 and
R.sub.10 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.9R.sub.10 is a
C.sub.2-C.sub.6alkylene group; R.sub.18 and R.sub.19 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, or phenyl optionally
substituted with any combination of one to three halogen atoms, one
or two cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and when R.sub.18 and R.sub.19
are taken together with the atom to which they are attached, they
represent a ring in which R.sub.18R.sub.19 is a
C.sub.2-C.sub.6alkylene group; R.sub.12 and R.sub.15 are each
independently hydrogen or C.sub.1-C.sub.6alkyl; R.sub.13 and
R.sub.16 are each independently C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6halo-alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.28 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.6alkenyl C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6alkoxycarbo- nylalkyl, or phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; R.sub.29
is hydrogen, C.sub.1-C.sub.6alkyl or benzyl; A is --O--,
--S(O).sub.r--, or --NR.sub.34--; B is --CR.sub.37R.sub.38-- or
--C(.dbd.CR.sub.41R.sub.42)-- -; R.sub.34 is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one or two
C(O)OR.sub.3 groups or one or two C(O) NR.sub.4R.sub.5 groups,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6alkyl-carbonylalkyl group, or benzyl optionally
substituted on the phenyl ring with any combination of one to three
halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; R.sub.37 and R.sub.38 are each
independently hydrogen, halogen, C.sub.1-C.sub.6 alkyl optionally
substituted with one or two cyano groups, one or two C(O)R.sub.2
groups, one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups or one or two NR.sub.9R.sub.10 groups,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C(O)NR.sub.12S(O).sub.nR.sub.13, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one to three C.sub.1-C.sub.4alkyl
groups, one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one C.sub.2-C.sub.6
alkylcarbonyl group, one C.sub.3-C.sub.6alkoxycarbonylalkyl group
or one C.sub.3-C.sub.6 alkylcarbonylalkyl group, and when R.sub.37
and R.sub.38 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.37R.sub.38 is a
C.sub.2-C.sub.6alkylene group; R.sub.41 and R.sub.42 are each
independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl,
hydroxy-carbonyl, or phenyl optionally substituted with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; r is an integer of 0, 1 or 2; n
and p are each independently an integer of 2; and Q is selected
from 147
4. The compound according to claim 3 wherein X is fluorine; Y is
chlorine; R is C.sub.1-C.sub.8alkyl optionally substituted with any
combination of one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O) (OR.sub.6).sub.2
groups, one or two OR.sub.7 groups, one or two SR.sub.8 groups, one
or two NR.sub.9R.sub.10 groups, one or two
C(O)NR.sub.12S(O).sub.nR.sub.13 groups, one furyl group or one
phenyl group optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4alkoxy groups or one nitro group, phenyl
optionally substituted with any combination of one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one or two C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.3-C.sub.6alkoxycarbon- ylalkyl groups or one or two
NR.sub.15S(O).sub.pR.sub.16 groups, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.8alkenyl or C.sub.3-C.sub.8alkynyl; Z is O; R.sub.3
is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, phenyl optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or benzyl optionally substituted
on the phenyl ring with any combination of one to three halogen
atoms, one or two cyano groups, one or two nitro groups, one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4-haloalkoxy groups; R.sub.4
and R.sub.5 are each independently hydrogen or
C.sub.1-C.sub.6alkyl, and when R.sub.4 and R.sub.5 are taken
together with the atom to which they are attached, they represent a
ring in which R.sub.4R.sub.5 is a C.sub.2-C.sub.6alkylene group;
R.sub.6 is hydrogen or C.sub.1-C.sub.6alkyl; R.sub.7 and R.sub.8
are each independently hydrogen, C.sub.1-C.sub.6alkyl
C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxycarbonylalkyl- ; R.sub.9 and R.sub.10 are
each independently hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl, and when R.sub.9 and R.sub.10
are taken together with the atom to which they are attached, they
represent a ring in which R.sub.9R.sub.10 is a
C.sub.2-C.sub.6alkylene group; R.sub.12 and R.sub.15 are hydrogen;
R.sub.13 and R.sub.16 are each independently C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.6-haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6alkynyl, or benzyl optionally substituted on the
phenyl ring with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; A is --O-- or --S(O).sub.r--; B
is --CR.sub.37R.sub.38-- or --C(.dbd.CR.sub.41R.sub.42)--; R.sub.37
and R.sub.38 are each independently hydrogen, halogen,
C.sub.1-C.sub.6alkyl optionally substituted with one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two OR.sub.7 groups or one or two NR.sub.9R.sub.10 groups, or
benzyl optionally substituted on the phenyl ring with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups or one C.sub.3-C.sub.6alkoxycar-
bonylalkyl group, and when R.sub.37 and R.sub.38 are taken together
with the atom to which they are attached, they represent a ring in
which R.sub.37R.sub.38 is a C.sub.2-C.sub.6alkylene group; R.sub.41
and R.sub.42 are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl or
hydroxy-carbonyl; r is an integer of 0, 1 or 2; n and p are each
independently an integer of 2; and Q is selected from 148
5. The compound according to claim 4 selected from the group
consisting of
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl-
}-1-cyclohexene-1,2-dicarboximide;
3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo--
2-thiazolidinylidene)amino]phenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H-
)-pyrimidinedione; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazol-
idineacetate;
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-d-
ioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-de-
lta5,alpha-thiazoli-dineacetic acid, diethyl ester; ethyl
5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluoro-phenyl}imino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6--
acetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethy-
l)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidin-
eacetate;
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazo-
lidineacetic acid, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
rifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazo-
lidinediacetic acid, 3-ethyl methyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-m-
ethyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imi-
no}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester;
ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)met-
hyl]-4-oxo-3-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-ox-
o-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester; methyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetate; methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
rifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazo-
lidinediacetic acid, 3-ethyl 2-fluoroethyl ester; 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-
-oxo-3-thiazolidineacetate; allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-
-3-thiazolidineacetate; isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo--
3-thiazolidineacetate;
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazol-
idinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidi-
nedione; cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
olidineacetate; ethyl
5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-t-
hiazolidineacetate;
3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinylide-
ne)amino]-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidi-
nedione;
3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidinyl-
idene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedion-
e;
3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidinyli-
dene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione-
; ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineace-
tate;
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorop-
henyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
methyl
2-{(2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepropionate;
methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyriziidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineace-
tate, D-; methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-.alpha.-(p-nitrob-
enzyl)-3-thiazolidineacetate, L-; ethyl
a-benzyl-2-{{2-chloro-5-[3,6-dihyd-
ro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoropheny-
l}imino}-4-oxo-3-thiazolidineacetate, L-; and methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
li-dineacetate, DL-.
6. A method for the control of undesirable plant species which
comprises applying to the foliage of said plants or to the soil or
water containing seeds or other propagating organs thereof, a
herbicidally effective amount of a compound having the structural
formula I 149wherein A, B, Q, R, X, Y and Z are as described in
claim 1.
7. The method according to claim 6 wherein A, B, Q, R, X, Y and Z
are as described in claim 2.
8. The method according to claim 7 wherein A, B, Q, R, X, Y and Z
are as described in claim 3.
9. The method according to claim 8 wherein A, B, Q. R, X, Y and Z
are as described in claim 4.
10. The method according to claim 9 wherein the compound is
selected from the group consisting of
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazol-
i-dinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;
3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-
-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetate;
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-th-
iazoli-dineacetic acid, diethyl ester; ethyl
5-{{2-chloro-5-[3,6-dihydro-3-
-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}im-
ino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6-acetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-
-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid,
3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacetate-
;
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineace-
tic acid, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl methyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester; ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-d-
ineacetate; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)me-
thyl]-4-oxo-3-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,-
6-dioxo-4-(tri-flucromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-o-
xo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;
methyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetate; methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
rifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazo-
lidinediacetic acid, 3-ethyl 2-fluoroethyl ester; 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-
-oxo-3-thiazolidineacetate; allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-
-3-thiazolidineacetate; isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-
-3-thiazolidineacetate;
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazo-
lidinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione; cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-
-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thia-
zolidineacetate; ethyl
5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-d-
ioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3--
thiazolidineacetate;
3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinyli--
dene)amino]-2-fluorophenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrim-
idinedione;
3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione;
3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidin-
ylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedi-
one; ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidine-
acetate;
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluo-
rophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropionate;
methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacet-
ate, D-; methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-.alpha.-(p-nitrob-
enzyl)-3-thiazolidineacetate, L-; ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-
-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluor-
ophenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetate, DL-.
11. The method according to claim 6 wherein the compound is applied
to the foliage of the undesirable plant species or to the soil or
water containing seeds or other propagating organs thereof in the
presence of crop plants, crop seeds or other crop propagating
organs.
12. The method according to claim 11 wherein the crop is a cereal
crop.
13. The method according to claim 12 wherein the cereal crop is
selected from the group consisting of corn, wheat and rice.
14. The method according to claim 13 wherein the cereal crop is
corn and the compound is selected from the group consisting of
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl-
}-1-cyclohexene-1,2-dicarboximide; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-met-
hyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino-
}-4-oxo-3-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiaz-
olidinediacetic acid, 3-ethyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl--
2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4--
oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl isopropyl ester; ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-di-
hydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoroph-
enyl}imino}-4-oxo-3-thiazolidine-acetate;
2-{{2-chloro-5-[3,6-dihydro-3-me-
thyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imin-
o}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester;
isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetate; methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
ri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiaz-
olidinediacetic acid, 3-ethyl 2-fluoroethyl ester; 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
and
2-{(2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(-
2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester.
15. The method according to claim 13 wherein the cereal crop is
wheat and the compound is selected from the group consisting of
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-th-
iazoli-dineacetic acid, diethyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methy-
l-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-
-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl methyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl isopropyl ester; ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-di-
hydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoroph-
enyl}imino}-4-oxo-3-thiazolidine-acetate; ethyl
2-{{2-chloro-5-[3,6-dihydr-
o-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-pheny-
l}imino}-5-[(methylcarbamoyl)methyl]-4-oxo-3-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-
-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl (2-propynyl) ester; isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-
-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-
imino}-4-oxo-5-thiazolidineacetate; methyl
.alpha.-benzyl-2-{{2-chloro-5-[-
3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fl-
uorophenyl}imino}-4-oxo-3-thiazolidineacetate, L-;
2-{{2-chloro-5-[3,6-dih-
ydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophe-
nyl}-imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl
2-fluoroethyl ester; 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-th-
iazolidine-acetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidi-
nediacetic acid, 3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-
-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-
-(hydroxyethyl)-4-oxo-3-thiazolidineacetate; and cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate.
16. The method according to claim 13 wherein the cereal crop is
rice and the compound is selected from the group consisting of
ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethy-
l)-1
(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluorophenyl-
}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropionate;
methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacet-
ate, L-; methyl
.alpha.-benzyl-2-{{2-chloro-5-(3,6-dihydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)-1
(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3--
thiazolidineacetate, D-; methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-d-
ioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-.a-
lpha.-(p-nitrobenzyl)-3-thiazolidineacetate, L-; ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacet-
ate, L-; and methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-
-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyri-midinyl]-4-fluorophenyl}i-
mino}-4-oxo-3-thiazolidineacetate, DL-.
17. The method according to claim 11 wherein the crop is
soybean.
18. The method according to claim 17 wherein the compound is
selected from the group consisting of ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dih-
ydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophe-
nyl}imino}-4-oxo-3-thiazolidine-acetate;
2-{{2-chloro-5-[3,6-dihydro-3-met-
hyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino-
}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl 2-fluoroethyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester; allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate; and
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylid-
ene)amino]phenyl}-1-methyl-6-(tri-fluoromethyl)-2,4(1H,3H)-pyrimidinedione-
.
19. The method according to claim 6 wherein the compound is applied
to the foliage of the undesirable plant species or to the soil or
water containing seeds or other propagating organs thereof at a
rate of about 0.01 kg/ha to 1 kg/ha.
20. The method according to claim 6 wherein the compound is applied
in combination with or in conjunction with one or more other
biological compounds.
21. A herbicidal composition which comprises an inert solid or
liquid carrier and a herbicidally effective amount of a compound
having the structural formula I 150wherein A, B, Q, R, X, Y and Z
are as described in claim 1.
22. The composition according to claim 21 wherein A, B, Q, R, X, Y
and Z are as described in claim 2.
23. The composition according to claim 22 wherein A, B, Q, R, X, Y
and Z are as described in claim 3.
24. The composition according to claim 23 wherein A, B, Q, R, X, Y
and Z are as described in claim 4.
25. The composition according to claim 24/ wherein the compound is
selected from the group consisting of
N-{4-chloro-2-fluoro-5-[(3-methyl-4-
-oxo-2-thiazolidinylidene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide;
3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]phenyl}-
-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)p-
yrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate;
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,alpha-th-
iazoli-dineacetic acid, diethyl ester; ethyl
5-{{2-chloro-5-[3,6-dihydro-3-
-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}im-
ino}-7-oxo-4-thia-6-azaspiro[2.4]heptane-6-acetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic acid,
3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacetate-
;
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineace-
tic acid, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl methyl ester;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
,5-thiazolidinediacetic acid, 3-ethyl isopropyl ester; ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidin-
eacetate; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)meth-
yl]-4-oxo-3-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo--
3,5-thiazolidinediacetic acid, 3-ethyl (2-propynyl) ester; methyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetate; methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate, L-;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
rifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazo-
lidinediacetic acid, 3-ethyl 2-fluoroethyl ester; 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetate;
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-
-oxo-3-thiazolidine-acetate; allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,-
6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-
-3-thiazolidineacetate; isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-
-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo--
3-thiazolidineacetate;
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazol-
idinylidene)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidi-
nedione; cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
olidineacetate; ethyl
5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-t-
hiazolidineacetate;
3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinyli-d-
ene)amino]-2-fluorophenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimi-
dinedione;
3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidin-
ylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedi-
one;
3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidiny-
lidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedio-
ne; ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinea-
cetate;
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluor-
ophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)--
pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepropionate;
methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacet-
ate, D-; methyl
2-{{2-chloro-5-[3,G-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-.alpha.-(p-nitrobe-
nzyl)-3-thiazolidineacetate, L-; ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6--
dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-
phenyl}imino}-4-oxo-3-thiazolidineacetate, L-; and methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyri-midinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
oli-dineacetate, DL-.
26. The composition according to claim 21 which further comprises
one or more other biological compounds.
27. A compound having the structural formula 151wherein U is
--N.dbd.C.dbd.NR, --N.dbd.C.dbd.S or 152Q is 153D, D.sub.1, R,
R.sub.43, R.sub.44, R.sub.45, R.sub.46, R.sub.47, R.sub.48, X and Y
are as described in claim 1.
28. The compound according to claim 27 wherein U is
--N.dbd.C.dbd.NR, --N.dbd.C.dbd.S or 154Q is 155X is hydrogen,
fluorine or chlorine; Y is fluorine, chlorine, nitro or cyano; R is
hydrogen, C.sub.1-C.sub.6 alkyl optionally substituted with one to
three halogen atoms, one or two C(O)OR.sub.3 groups, one cyano
group, one OR.sub.7 group, one SR.sub.8 group, one
P(O)(OR.sub.6).sub.2 group, or a C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, phenyl, benzyl or furfural group, wherein
each group is optionally substituted with one to three halogen
atoms, one C.sub.1-C.sub.3alkoxy group or one C(O)OR.sub.3 group;
R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.3alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; and R.sub.8 is hydrogen,
C.sub.1-C.sub.3alkyl or C.sub.3-C.sub.6alkoxycarbonyl.
29. A method for the preparation of a compound having the
structural formula 156wherein Q is 157X is hydrogen, fluorine or
chlorine; Y is fluorine, chlorine, nitro or cyano; R is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two C(O)OR3 groups, one cyano group, one
OR.sub.7 group, one SR.sub.8 group, one P(O)(OR.sub.6).sub.2 group,
or a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl, benzyl
or furfural group, wherein each group is optionally substituted
with one to three halogen atoms, one C.sub.1-C.sub.3alkoxy group or
one C(O)OR.sub.3 group; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.6alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; and R.sub.8 is hydrogen,
C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6alkoxycarbonyl which method
comprises reacting a substituted aniline compound having the
structural formula 158wherein Q. X and Y are as described above
with an isothiocyanate compound having the structural
formulaS.dbd.C.dbd.N--Rwher- ein R is as described above.
30. The method according to claim 29 wherein the reaction is
conducted in the presence of a solvent.
31. A method for the preparation of a compound having the
structural formula 159wherein Q is 160X is hydrogen, fluorine or
chlorine; Y is fluorine, chlorine, nitro or cyano; R is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two C(O)OR.sub.3 groups, one cyano group, one
OR.sub.7 group, one SR.sub.8 group, one P(O)(OR.sub.6).sub.2 group,
or a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl, benzyl
or furfural group, wherein each group is optionally substituted
with one to three halogen atoms, one C.sub.1-C.sub.3alkoxy group or
one C(O)OR.sub.3 group; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.3alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; and R.sub.8 is hydrogen,
C.sub.1-C.sub.3alkyl or C.sub.3-C.sub.6alkoxycarbonyl which method
comprises reacting an isothiocyanate compound having the structural
formula 161wherein Q. X and Y are as described above with a primary
amine compound having the structural formulaH.sub.2NRwherein R is
as described above.
32. The method according to claim 31 wherein the reaction is
conducted in the presence of a solvent.
33. A method for the preparation of a compound having the
structural formula 162wherein Q is 163X is hydrogen, fluorine or
chlorine; Y is fluorine, chlorine, nitro or cyano; R is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two C(O)OR.sub.3 groups, one cyano group, one
OR.sub.7 group, one SR.sub.8 group, one P(O)(OR.sub.6).sub.2 group,
or a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl, benzyl
or furfural group, wherein each group is optionally substituted
with one to three halogen atoms, one C.sub.1-C.sub.3alkoxy group or
one C(O)OR.sub.3 group; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.3alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; R.sub.8 is hydrogen,
C.sub.1-C.sub.3alkyl or C.sub.3-C.sub.6alkoxycarbonyl; R.sub.37 and
R.sub.38 are each independently hydrogen, halogen,
C.sub.1-C.sub.6alkyl optionally substituted with one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two OR.sub.7 groups or one or two NR.sub.9R.sub.10 groups, or
benzyl optionally substituted on the phenyl ring with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups or one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, and when R.sub.37 and
R.sub.38 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.37R.sub.38 is a
C.sub.2-C.sub.6alkylene group; R.sub.4 and R.sub.5 are each
independently hydrogen or C.sub.1-C.sub.6alkyl, and when R.sub.4
and R.sub.5 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.4 and R.sub.5 is a
C.sub.2-C.sub.6alkylene group; and R.sub.9 and R.sub.10 are each
independently hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl, and when R.sub.9 and R.sub.10
are taken together with the atom to which they are attached, they
represent a ring in which R.sub.9R.sub.10 is a
C.sub.2-C.sub.6alkylene group which method comprises reacting a
substituted thiourea compound having the structural formula
164wherein Q, R, X and Y are as described above with a ketone
compound having the structural formula 165wherein R.sub.37 and
R.sub.38 are as described above, and X.sub.1 is halogen.
34. The method according to claim 33 wherein the reaction is
conducted in the presence of a solvent.
35. The method according to claim 33 wherein the reaction is
conducted in the presence of a base.
36. A method for the preparation of a compound having the
structural formula 166wherein Q is 167X is hydrogen, fluorine or
chlorine; Y is fluorine, chlorine, nitro or cyano; R is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two C(O)OR.sub.3 groups, one cyano group, one
OR.sub.7 group, one SR.sub.8 group, one P(O)(OR.sub.6).sub.2 group,
or a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl, benzyl
or furfural group, wherein each group is optionally substituted
with one to three halogen atoms, one C.sub.1-C.sub.3alkoxy group or
one C(O)OR.sub.3 group; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.6alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; and R.sub.8 is hydrogen,
C.sub.1-C.sub.3alkyl or C.sub.3-C.sub.6alkoxycarbonyl which method
comprises reacting a substituted thiourea compound having the
structural formula 168wherein Q, R, X and Y are as described above
with a compound having the structural
formulaR.sub.55SO.sub.2Clwherein R.sub.55 is C.sub.1-C.sub.4alkyl
or phenyl optionally substituted with one or two
C.sub.1-C.sub.4alkyl groups in the presence of a base.
37. A method for the preparation of a compound having the
structural formula 169wherein Q is 170X is hydrogen, fluorine or
chlorine; Y is fluorine, chlorine, nitro or cyano; R is hydrogen,
C.sub.1-C.sub.6alkyl optionally substituted with one to three
halogen atoms, one or two C(O)OR.sub.3 groups, one cyano group, one
OR.sub.7 group, one SR.sub.8 group, one P(O)(OR.sub.6).sub.2 group,
or a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl, benzyl
or furfural group, wherein each group is optionally substituted
with one to three halogen atoms, one C.sub.1-C.sub.3alkoxy group or
one C(O)OR.sub.3 group; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl
or C.sub.1-C.sub.6haloalkyl; R.sub.6 is hydrogen of
C.sub.1-C.sub.3alkyl; R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; R.sub.8 is hydrogen,
C.sub.1-C.sub.3alkyl or C.sub.3-C.sub.6alkoxycarbonyl; R.sub.37 and
R.sub.38 are each independently hydrogen, halogen,
C.sub.1-C.sub.6alkyl optionally substituted with one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two OR.sub.7 groups or one or two NR.sub.9R.sub.10 groups, or
benzyl optionally substituted on the phenyl ring with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups or one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, and when R.sub.37 and
R.sub.38 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.37R.sub.38 is a
C.sub.2-C.sub.6alkylene group; R.sub.4 and R.sub.5 are each
independently hydrogen or C.sub.1-C.sub.6alkyl, and when R.sub.4
and R.sub.5 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.4 and R.sub.5 is a
C.sub.2-C.sub.6alkylene group; R.sub.9 and R.sub.10 are each
independently hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl, and when R.sub.9 and R.sub.10
are taken together with the atom to which they are attached, they
represent a ring in which R.sub.9R.sub.10 is a
C.sub.2-C.sub.6alkylene group; and A is O, N or S which method
comprises reacting a substituted carbodiimide having the structural
formula 171wherein Q, R, X and Y are as described above with a
compound having the structural formula 172wherein A, R.sub.37 and
R.sub.38 are as described above.
38. The method according to claim 37 wherein the reaction is
conducted in the presence of a catalyst.
Description
BACKGROUND OF THE INVENTION
[0001] Weeds cause tremendous global economic losses by reducing
crop yields and lowering crop quality. In the United States alone,
agronomic crops must compete with hundreds of weed species.
[0002] In spite of the commercial herbicides available today,
damage to crops caused by weeds still occurs. Accordingly, there is
ongoing research to create new and more effective herbicides.
[0003] JP 07304759-A and DE 3505432-A describe certain
iminothiazolone derivatives which are useful as herbicidal agents.
However, none of the compounds described in those applications are
substituted with the 3-heterocyclylphenyl group of the present
invention.
[0004] U.S. Pat. No. 3,287,466 describes certain
3-alkyl-4-imino-5-(arylim- ino)-2-thiazolidinone compounds which
are useful as herbicidal agents. However, the arylimino groups of
those compounds are not substituted with the heterocyclyl groups of
this invention.
[0005] It is therefore an object of the present invention to
provide compounds which are highly effective for controlling
undesirable plant species.
[0006] It is also an object of the present invention to provide
methods for controlling undesirable plant species.
[0007] These and other objects of the present invention will become
more apparent from the detailed description thereof set forth
below.
SUMMARY OF THE INVENTION
[0008] The present invention describes
1-(3-heterocyclyl-phenyl)isothioure- a, -isourea, -guanidine and
-amidine compounds which are useful as herbicidal agents.
[0009] The 1-(3-heterocyclylphenyl)isothiourea, -isourea,
-guanidine and -amidine compounds of the present invention have the
structural formula I 2
[0010] wherein p0 X and Y are each independently hydrogen, halogen,
nitro, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl or
S(O).sub.mR.sub.1;
[0011] R is hydrogen,
[0012] a C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.8alkenyl, C.sub.1-C.sub.7-cycloalkenyl or
C.sub.3-C.sub.8alkynyl group, wherein each group is optionally
substituted with any combination of one to six halogen atoms, one
or two cyano groups, one or two nitro groups, one or two
C(W)R.sub.2 groups, one or two C(W)OR.sub.3 groups, one or two
C(W)NR.sub.4R.sub.5 groups, one or two P(V)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups, one or two SR.sub.8 groups, one or two
NR.sub.9R.sub.10 groups, one or two OC(W)R.sub.11 groups, one or
two NR.sub.12S(O).sub.nR.sub.13 groups, one or two
C(W)NR.sub.12S(O).sub.nR.sub.13 groups,
[0013] one 4- to 10-membered heterocyclic ring optionally
substituted with any combination of one or two oxo groups, one or
two thioxo groups, one to three halogen atoms, one to three nitro
groups, one to three cyano groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.1-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxy- alkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonyalkyl groups, one to three
C.sub.3-C.sub.6haloalkyl-carbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups, or
[0014] one phenyl group optionally substituted with any combination
of one to three halogen atoms, one to three nitro groups, one to
three cyano groups, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two C.sub.2-C.sub.6
haloalkoxyalkyl groups, one or two C(O)OR.sub.14 groups, one or two
C(O)R.sub.14 groups, one to three
C.sub.1-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.1-C.sub.6alkylcarbonyl-alkyl groups, one to three
C.sub.3-C.sub.6haloalkyl-carbonylalkyl groups one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups,
[0015] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one or two oxo groups, one or two thioxo
groups, one to three halogen atoms, one to three nitro groups, one
to three cyano groups, one to three C.sub.1-C.sub.4-alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxy-- alkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxy-carbonylalkyl groups, one to three
C.sub.3-C.sub.6halo-alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6-alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6-haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15(O).sub.pR.- sub.16 groups,
[0016] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three nitro groups, one to three cyano
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4-haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6Ealkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(W)NR.sub.15S(O).sub.pR- .sub.16 groups,
[0017] OR.sub.17,
[0018] NR.sub.18R.sub.19,
[0019] NR.sub.20S(O).sub.qR.sub.21,
[0020] NR.sub.22C(V)R.sub.23,
[0021] NR.sub.24P(V)(OR.sub.25).sub.2,
[0022] C(V)NR.sub.20S(O).sub.qR.sub.21,
[0023] cyano,
[0024] S(O).sub.qR.sub.26,
[0025] P(V)(OR.sub.27).sub.2,
[0026] C(V)R.sub.28 or
[0027] C(V)OR.sub.29;
[0028] W is O, S, NR.sub.30, NOR.sub.31 or NNR.sub.32R.sub.33;
[0029] V and Z are each independently O or S;
[0030] R.sub.1 and R.sub.14 are each independently
C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4haloalkyl;
[0031] R.sub.2 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.7cycloalky- l, C.sub.1-C.sub.6-haloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-C.sub.6-alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxy-carbonylalkyl,
[0032] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxy-a- lkyl groups, one or two nitro groups,
one or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxy-carbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylca- rbonylalkyl group,
[0033] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one or two oxo groups, one or two thioxo
groups, one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxy-alkyl groups, one or two
C.sub.2-C.sub.6haloalkoxya- lkyl groups, one or two nitro groups,
one or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylca- rbonylalkyl group,
[0034] C.sub.1-C.sub.4alkyl substituted with one phenyl group
wherein the phenyl group is optionally substituted with any
combination of one to three halogen atoms, one or two nitro groups,
one or two cyano groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0035] C.sub.1-C.sub.4alkyl substituted with one 4- to 10-membered
heterocyclic ring wherein the heterocyclic ring is optionally
substituted with any combination of one to three halogen atoms, one
or two nitro groups, one or two cyano groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4 haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups; p0 R.sub.3 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cyclo-alkyl, C.sub.3-C.sub.6alkenyl
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalkyl- ,
C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
[0036] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0037] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups,
[0038] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0039] an alkali metal, alkaline earth metal, manganese, copper,
zinc, cobalt, silver, nickel, ammonium or organic ammonium
cation;
[0040] R.sub.4 and R.sub.5 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.1-C.sub.6alkoxy, hydroxy,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6halo-alkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalky- l, C.sub.3-C.sub.6,
haloalkoxycarbonylalkyl, C.sub.2-C.sub.6hydroxycarbony- lalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl, C.sub.2-C.sub.6haloalkylsulfony-
lalkyl, S(O).sub.pR.sub.16,
[0041] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0042] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, or
[0043] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0044] provided that only one of R.sub.4 and R.sub.5 can be hydroxy
or C.sub.1-C.sub.6alkoxy, and
[0045] when R.sub.4 and R.sub.5 are taken together with the atom to
which they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted by oxygen,
sulfur or nitrogen, and optionally substituted with one to three
methyl groups or one or more halogen atoms;
[0046] R.sub.6, R.sub.25 and R.sub.27 are each independently
hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6haloalkyl,
[0047] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0048] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0049] R.sub.7, R.sub.8 and R.sub.17 are each independently
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalky- l, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6aloalkynyl, C.sub.2-C.sub.6alkoxyalkyl,
C.sub.2-C.sub.6haloalkoxyalkyl, C.sub.2-C.sub.6alkylcarbonylalkyl,
C.sub.2-C haloalkylcarbonylalkyl,
C.sub.2-C.sub.6-alkoxycarbonylalkyl,
C.sub.2-C.sub.6haloalkoxycarbonylalk- yl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalk- yl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C(V)NR.sub.12S(O).sub.nR.sub.13,
[0050] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0051] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4halo-alkoxy groups, or
[0052] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0053] R.sub.9, R.sub.10, R.sub.18, R.sub.19, R.sub.32 and R.sub.33
are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6halo-alkylcarbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6-haloalkoxycarbonylal- kyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalky- l,
C.sub.2-C.sub.6haloalkylsulfonylalkyl,
[0054] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0055] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three C.sub.1-C.sub.4
haloalkoxy groups, or
[0056] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and
[0057] when R.sub.9 and R.sub.16 or R.sub.18 and R.sub.19 or
R.sub.32 and R.sub.33 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted by oxygen,
sulfur or nitrogen, and optionally substituted with one to three
methyl groups or one or more halogen atoms;
[0058] R.sub.11 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.7cyclo-alkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkyl-carbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalky- l,
C.sub.3-C.sub.6halo-alkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonyl- alkyl,
[0059] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0060] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0061] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0062] R.sub.12, R.sub.15, R.sub.20 and R.sub.24 are each
independently hydrogen,
[0063] C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.6alkenyl or C.sub.3-C.sub.6alkynyl;
[0064] R.sub.13, R.sub.21, R.sub.22, R.sub.23, R.sub.26, R.sub.28
and R.sub.29 are each independently hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl- ,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6haloalkoxycarbonylalk- yl,
[0065] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two C.sub.2-C.sub.6
alkoxyalkyl groups, one or two C.sub.2-C.sub.6halo-alkoxy- alkyl
groups, one or two nitro groups, one or two cyano groups, one
C.sub.3-C.sub.6alkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-- carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group or one
C.sub.2-C.sub.6hydroxycarbonylalkyl group,
[0066] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxyalkyl groups, one or two nitro groups,
one or two cyano groups, one C.sub.3-C.sub.6alkoxy-carbonyl- alkyl
group, one C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarb- onylalkyl group or one
C.sub.2-C.sub.6hydroxycarbonylalkyl group,
[0067] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.6haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0068] furfural optionally substituted with any combination of one
to three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0069] R.sub.16 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.1-C.sub.6cyclo-alkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalky- l,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl,
[0070] phenyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups,
[0071] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0072] furfural optionally substituted with any combination of one
to three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0073] R.sub.30 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.6-cyclo-alkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
[0074] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one
C.sub.2-C.sub.6alkoxy-alkyl group, one
C.sub.2-C.sub.6haloalkoxyalkyl group, one
NR.sub.15S(O).sub.nR.sub.16- , group, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalk- yl group, one
C.sub.3-C.sub.6alkyl-carbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group or one
C.sub.3-C.sub.6haloalkyl-carbonylalkyl group,
[0075] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one C.sub.2-C.sub.6alkoxyalkyl
group, one C.sub.2-C.sub.6haloalkoxyalkyl group, one
NR.sub.15S(O).sub.nR.sub.16 group, one C.sub.2-C.sub.6alkoxyca-
rbonyl group, one C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6alkyl-carbo- nylalkyl group, one
C.sub.3-C.sub.6haloalkoxy-carbonylalkyl group or one
C.sub.3-C.sub.6haloalkyl-carbonylalkyl group,
[0076] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4-haloalkoxy groups, or
[0077] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0078] R.sub.31 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.7Cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6haloalkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6-haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalky- l,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalk- yl,
C.sub.2-C.sub.6haloalkylsulfonylalkyl,
C.sub.2-C.sub.6hydroxy-carbonyl- alkyl,
C(V)NR.sub.12S(O).sub.pR.sub.13,
[0079] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0080] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups,
[0081] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0082] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0083] A is --O--, --S(O).sub.r--, --NR.sub.34-- or
--CR.sub.35R.sub.36--;
[0084] B is --CR.sub.37R.sub.38(CR.sub.39R.sub.40).sub.s--,
--C(.dbd.T)-- or --C(.dbd.CR.sub.41R.sub.42)--;
[0085] R.sub.34, R.sub.35, R.sub.36, R.sub.37, R.sub.38, R.sub.39
and R.sub.40 are each independently hydrogen, halogen,
[0086] C.sub.1-C.sub.6alkyl optionally substituted with one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one or two C(W)R.sub.2 groups, one or two C(W)OR.sub.3
groups, one or two C(W)NR.sub.4R.sub.5 groups, one or two
P(V)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or two
SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups or one or two
OC(W)R.sub.11 groups,
[0087] C.sub.3-C.sub.7cycloalkyl,
[0088] C.sub.3-C.sub.6alkenyl,
[0089] C.sub.3-C.sub.6haloalkenyl
[0090] C.sub.3-C.sub.6alkynyl,
[0091] C.sub.3-C.sub.6haloalkynyl,
[0092] C(V)NR.sub.12S(O).sub.nR.sub.13,
[0093] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6halo-alkoxya- lkyl groups, one or two nitro groups,
one or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6halo-alkoxycarbonyl group, one C
2-C.sub.6alkylcarbonyl group, one C.sub.2-C.sub.6haloalkylcarbonyl
group, one C.sub.3-C.sub.6alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6halo-alk- oxycarbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group,
[0094] a 4- to 10-membered heterocyclic ring optionally substituted
with any combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyalkyl groups, one or two nitro groups, one
or two cyano groups, one NR.sub.15S(O).sub.pR.sub.16 group, one
C.sub.2-C.sub.6-alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxyc- arbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group,
[0095] C.sub.1-C.sub.4alkyl substituted with one phenyl group
wherein the phenyl group is optionally substituted with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6-haloalkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, one
C.sub.3-C.sub.6haloalkoxyca- rbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group, one
C.sub.3-C.sub.6haloalkylcarbonylalkyl group, one
C.sub.3-C.sub.8alkoxycar- bonylalkoxy group or one
C.sub.2-C.sub.8hydroxycarbonylalkoxy group, or
[0096] C.sub.1-C.sub.4alkyl substituted with one 4- to 10-membered
heterocyclic ring wherein the heterocyclic ring is optionally
substituted with any combination of one to three halogen atoms, one
to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6haloalkoxycarbony- l group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.2-C.sub.6haloalkyl-carbonyl group, one
C.sub.3-C.sub.6alkoxycarbony- lalkyl group, one
C.sub.3-C.sub.6haloalkoxycarbonylalkyl group, one
C.sub.3-C.sub.6alkylcarbonylalkyl group or one
C.sub.3-C.sub.6-haloalkylc- arbonylalkyl group, and
[0097] when R.sub.35, and R.sub.36 or R.sub.37 and R.sub.38 or
R.sub.39 and R.sub.40 are taken together with the atom to which
they are attached, they represent a ring in which R.sub.35R.sub.36
or R.sub.37R.sub.38 or R.sub.39R.sub.40 is a
C.sub.2-C.sub.6alkylene group;
[0098] T is O, S, NR.sub.30, NOR.sub.31 or NNR.sub.32R.sub.33;
[0099] R.sub.41 and R.sub.42 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, C.sub.2-C.sub.6alkylcarbonyl,
C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6-alkoxycarbonyl,
C.sub.2-C.sub.6haloalkoxycarbonyl, hydroxycarbonyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl- ,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylal- kyl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylal- kyl,
[0100] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups, one to three C.sub.1-C.sub.4haloalkoxy groups or one
C.sub.3-C.sub.8alkoxycarbonylalko- xy group,
[0101] benzyl optionally substituted on the phenyl ring 33442-01
with any combination of one to three halogen atoms, one or two
cyano groups, one or two nitro groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0102] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and when
R.sub.41 and R.sub.42 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted with one group
selected from O, S(O).sub.r or NR.sub.31, and optionally
substituted with one to three methyl groups or one or more halogen
atoms;
[0103] m and r are each independently an integer of 0, 1 or 2;
[0104] n, p and q are each independently an integer of 1 or 2;
[0105] s is an integer of 0 or 1;
[0106] Q is selected from 3
[0107] D and D.sub.1 are each independently O or S;
[0108] E is hydroxy, halogen, C.sub.1-C.sub.4alkoxy or
C.sub.1-C.sub.4alkylthio;
[0109] R.sub.43 and R.sub.44 are each independently hydrogen,
halogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.6cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl, cyano, amino,
hydroxy or benzyl, and when R.sub.43 and R.sub.44 are taken
together with the atom to which they are attached, they represent a
three- to seven-membered saturated or unsaturated ring optionally
interrupted by oxygen, sulfur or nitrogen, and optionally
substituted with one to three methyl groups or one or more halogen
atoms;
[0110] R.sub.45 and R.sub.46 are each independently hydrogen,
halogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl, OR.sub.51,
S(O).sub.tR.sub.52 or NR.sub.53R.sub.45, and when R.sub.45 and
R.sub.46 are taken together with the atom to which they are
attached, they represent a three- to seven-membered saturated or
unsaturated ring optionally interrupted by oxygen, sulfur or
nitrogen, and optionally substituted with one to three methyl
groups or one or more halogen atoms;
[0111] R.sub.47, R.sub.49 and R.sub.50 are each independently
hydrogen, halogen or C.sub.1-C.sub.6alkyl;
[0112] R.sub.48 is hydrogen, halogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl,
C.sub.3-C.sub.6alkynyl, OR.sub.51 or SR.sub.52;
[0113] R.sub.51 and R.sub.52 are each independently hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.1-C4cyanoalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6haloalkenyl- ,
C.sub.3-C.sub.6alkynyl, benzyl or
[0114] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0115] R.sub.53 is hydrogen, C.sub.1-C.sub.4alkyl, benzyl or
[0116] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three
[0117] C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0118] R.sub.54 in hydrogen, C.sub.1-C.sub.4alkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.7cycloalkyl, benzyl,
S(O).sub.tR.sub.52 or
[0119] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups; and
[0120] t is an integer of 0, 1 or 2; and
[0121] the agriculturally acceptable salts thereof.
[0122] This invention also relates to compositions containing those
compounds and methods for using those compounds and compositions.
Advantageously, it has been found that the compounds of the present
invention, and compositions containing them, are useful for the
control of undesirable plant species
DETAILED DESCRIPTION OF THE INVENTION
[0123] The present invention provides a method for the control of
undesirable plant species which comprises applying to the foliage
of said plants or to the soil or water containing seeds or other
propagating organs thereof, a herbicidally effective amount of a
formula I, 1-(3-heterocyclylphenyl)isothiourea, -isourea,
-guanidine or -amidine compound.
[0124] The 1-(3-heterocyclylphenyl)isothiourea, -isourea,
-guanidine and -amidine compounds of the present invention have the
structural formula I 4
[0125] wherein A, B, Q, R, X, Y and Z are as defined above for
formula I.
[0126] Preferred formula I compounds of this invention are those
wherein
[0127] X is hydrogen or halogen;
[0128] Y is hydrogen, halogen, nitro or cyano;
[0129] R is hydrogen,
[0130] a C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.8alkenyl, C.sub.5-C.sub.7cycloalkenyl or
C.sub.3-C.sub.8alkynyl group, wherein each group is optionally
substituted with any combination of one to six halogen atoms, one
or two cyano groups, one or two nitro groups, one or two
C(O)R.sub.2 groups, one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups, one or two SR.sub.8 groups, one or two
NR.sub.9R.sub.10 groups, one or two OC(O)R.sub.11 groups, one or
two NR.sub.12S(O).sub.nR.sub.13, groups, one or two
C(O)NR.sub.12S(O).sub.nR.sub.13 groups,
[0131] one 4- to 10-membered heterocyclic ring optionally
substituted with any combination of one or two oxo groups, one or
two thioxo groups, one to three halogen atoms, one to three nitro
groups, one to three cyano groups, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6-haloalkoxya- lkyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonyalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(O)NR.sub.15S(O).sub.pR- .sub.16 groups, or
[0132] one phenyl group optionally substituted with any combination
of one to three halogen atoms, one to three nitro groups, one to
three cyano groups, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.4 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6 alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups, one or two
NR.sub.15S(O).sub.pR.sub.16 groups or one or two
C(O)NR.sub.15S(O).sub.pR- .sub.16 groups,
[0133] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three nitro groups, one to three cyano
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4-haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two
C.sub.2-C.sub.6haloalkoxyal- kyl groups, one or two C(O)OR.sub.14
groups, one or two C(O)R.sub.14 groups, one to three
C.sub.3-C.sub.6alkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkoxycarbonylalkyl groups, one to three
C.sub.3-C.sub.6alkylcarbonylalkyl groups, one to three
C.sub.3-C.sub.6haloalkylcarbonylalkyl groups or one or two
NR.sub.15S(O).sub.pR.sub.16 groups,
[0134] OR.sub.17,
[0135] NR.sub.18R.sub.19,
[0136] NR.sub.20S(O).sub.qR.sub.21,
[0137] NR.sub.22C(O)R.sub.23,
[0138] C(O)NR.sub.20S(O).sub.qR.sub.21,
[0139] S(O).sub.qR.sub.26,
[0140] C(O)R.sub.28 or
[0141] C(O)OR.sub.29;
[0142] Z is 0;
[0143] R.sub.14 is C.sub.1-C.sub.4alkyl or
C.sub.1-C.sub.4haloalkyl;
[0144] R.sub.2 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.7cycloalky- l, C.sub.1-C.sub.6-haloalkyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
or
[0145] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4alkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6haloalkoxy- carbonylalkyl group;
[0146] R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl- , C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
[0147] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0148] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups,
[0149] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0150] an alkali metal, alkaline earth metal, manganese, copper,
zinc, cobalt, silver, nickel, ammonium- or organic ammonium
cation;
[0151] R.sub.4 and R.sub.5 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.1-C.sub.6alkoxy, hydroxy, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, S(O).sub.pR.sub.16,
[0152] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0153] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups,
[0154] provided that only one of R.sub.4 and R.sub.5 can be hydroxy
or C.sub.1-C.sub.6alkoxy, and when R.sub.4 and R.sub.5 are taken
together with the atom to which they are attached, they represent a
three- to seven-membered saturated or unsaturated ring optionally
interrupted by oxygen, sulfur or nitrogen, and optionally
substituted with one to three methyl groups or one or more halogen
atoms;
[0155] R.sub.6 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl- ,
[0156] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0157] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0158] R.sub.7 and R.sub.8 are each independently hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxycarbonylalkyl; R.sub.17 is hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-C.sub.6alkoxyalkyl, C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.2-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl- ,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
[0159] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three
[0160] C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0161] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0162] R.sub.9 and R.sub.10 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, C.sub.2-C.sub.6
hydroxycarbonylalkyl, or
[0163] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and
[0164] when R.sub.9 and R.sub.10 are taken together with the atom
to which they are attached, they represent a three- to
seven-membered saturated or unsaturated ring optionally interrupted
by oxygen, sulfur or nitrogen, and optionally substituted with one
to three methyl groups or one or more halogen atoms;
[0165] R.sub.18 and R.sub.19 are each independently hydrogen,
C.sub.1-C.sub.6salkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl-alkyl,
C.sub.2-C.sub.6hydroxycarbo- nylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl-alkyl, C.sub.2-C.sub.6haloalky-
lsulfonylalkyl,
[0166] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0167] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0168] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and
[0169] when R.sub.18 and R.sub.19 are taken together with the atom
to which they are attached, they represent a three- to
seven-membered saturated or unsaturated ring optionally interrupted
by oxygen, sulfur or nitrogen, and optionally substituted with one
to three methyl groups or one or more halogen atoms;
[0170] R.sub.11 is hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.1-C.sub.6haloalkyl;
[0171] R.sub.12, R.sub.15 and R.sub.20 are each independently
hydrogen or C.sub.1-C.sub.6alkyl;
[0172] R.sub.13, R.sub.16, R.sub.21 and R.sub.26 are each
independently C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7-cycloalky- l, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, or
[0173] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0174] R.sub.22 is hydrogen or C.sub.1-C.sub.6alkyl;
[0175] R.sub.23 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.7cycloalkyl,
C.sub.3-C.sub.6alkylcarbonylalkyl,
C.sub.3-C.sub.6haloalkylcarbonylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl- ,
C.sub.3-C.sub.6haloalkoxycarbonylalkyl,
[0176] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0177] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4 haloalkoxy groups;
[0178] R.sub.28 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.7-cycloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, or
[0179] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0180] R.sub.29 is hydrogen, C.sub.1-C.sub.6alkyl or benzyl;
[0181] A is --O--, --S(O).sub.r-- or --NR.sub.34--;
[0182] B is --CR.sub.37R.sub.38--, --C(O)-- or
--C(.dbd.CR.sub.41R.sub.42)- --;
[0183] R.sub.34 is hydrogen,
[0184] C.sub.1-C.sub.6alkyl optionally substituted with one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one or two C(O)R.sub.2 groups, one or two C(O)OR.sub.3
groups, one or two C(O)NR.sub.4R.sub.5 groups, one or two
P(O)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or two
SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups or one or two
OC(O)R.sub.11 groups,
[0185] C.sub.3-C.sub.7cycloalkyl,
[0186] C.sub.3-C.sub.6alkenyl,
[0187] C.sub.3-C.sub.6alkynyl,
[0188] C(O)NR.sub.12S(O).sub.nR.sub.13,
[0189] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalk- yl group or one
C.sub.3-C.sub.6alkylcarbonylalkyl group, or
[0190] C.sub.1-C.sub.4alkyl substituted with one phenyl group
wherein the phenyl group is optionally substituted with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two C.sub.2-C.sub.6
alkoxyalkyl groups, groups, one C.sub.2-C.sub.6alkoxycarb- onyl
group, one C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6-alkylcarb- onylalkyl group;
[0191] R.sub.37 and R.sub.38 are each independently hydrogen,
halogen
[0192] C.sub.1-C.sub.6alkyl optionally substituted with one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one or two C(O)R.sub.2 groups, one or two C(O)OR.sub.3
groups, one or two C(O)NR.sub.4R.sub.5 groups, one or two
P(O)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or two
SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups or one or two
OC(O)R.sub.11 groups,
[0193] C.sub.3-C.sub.7cycloalkyl,
[0194] C.sub.3-C.sub.6alkenyl,
[0195] C.sub.3-C.sub.6haloalkenyl
[0196] C.sub.3-C.sub.6alkynyl,
[0197] C.sub.3-C.sub.6haloalkynyl,
[0198] C(O)NR.sub.12S(O).sub.nR.sub.13,
[0199] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6 alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalky- l group or one
C.sub.3-C.sub.6alkylcarbonylalkyl group, or
[0200] C.sub.1-C.sub.4alkyl substituted with one phenyl group
wherein the phenyl group is optionally substituted with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalkyl group or one
C.sub.3-C.sub.6-alkylcarb- onylalkyl group, and
[0201] when R.sub.37 and R.sub.38 are taken together with the atom
to which they are attached, they represent a ring in which
R.sub.37R.sub.38 is a C.sub.2-C.sub.6alkylene group;
[0202] R.sub.41 and R.sub.42 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkylcarbonyl,
C.sub.2-C.sub.6alkoxycarbonyl, hydroxycarbonyl,
C.sub.3-C.sub.6alkylcarbo- nylalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl, C.sub.2-C.sub.6hydroxycarbon-
ylalkyl,
[0203] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups,
[0204] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, or
[0205] furfural optionally substituted with any combination of one
to three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and when
R.sub.41 and R.sub.42 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted with one group
selected from O, S(O).sub.r or NR.sub.31, and optionally
substituted with one to three methyl groups or one or more halogen
atoms;
[0206] r is an integer of 0, 1 or 2;
[0207] n, p and q are each independently an integer of 1 or 2;
[0208] Q is selected from 5
[0209] D and D.sub.1 are each independently O or S;
[0210] R.sub.43 and R.sub.44 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl, amino, or
benzyl;
[0211] R.sub.45 and R.sub.46 are each independently hydrogen,
halogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl or C.sub.3-C.sub.6alkynyl, and when
R.sub.45 and R.sub.46 are taken together with the atom to which
they are attached, they represent a three- to seven-membered
saturated or unsaturated ring optionally interrupted by oxygen,
sulfur or nitrogen, and optionally substituted with one to three
methyl groups or one or more halogen atoms; and
[0212] R.sub.47 and R.sub.48 are each independently hydrogen,
halogen or C.sub.1-C.sub.6alkyl.
[0213] More preferred formula I herbicidal agents of the present
invention are those wherein
[0214] X is hydrogen, fluorine or chlorine;
[0215] Y is fluorine, chlorine, nitro or cyano;
[0216] R is hydrogen,
[0217] C.sub.1-C.sub.8alkyl optionally substituted with any
combination of one to six halogen atoms, one or two cyano groups,
one or two nitro groups, one or two C(O)R.sub.2 groups, one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two P(O)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups, one or
two SR.sub.8 groups, one or two NR.sub.9R.sub.10 groups, one or two
C(O)NR.sub.12S(O).sub.nR.sub.13 groups,
[0218] one furyl group optionally substituted with any combination
of one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two C(O)OR.sub.14 groups or
one or two C(O)R.sub.14 groups,
[0219] one pyridyl group optionally substituted with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups, one or two C(O)OR.sub.14 groups
or one or two C(O)R.sub.14 groups, or
[0220] one phenyl group optionally substituted with any combination
of one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two C(O)OR.sub.14 groups or
one or two C(O)R.sub.14 groups,
[0221] phenyl optionally substituted with any combination of one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two C.sub.2-C.sub.6alkoxyalkyl
groups, one or two C(O)OR.sub.14 groups, one or two C(O)R.sub.14
groups, one to three C.sub.3-C.sub.6alkoxycarbonylalkyl groups or
one or two NR.sub.15S(O).sub.pR.sub.16 groups,
[0222] C.sub.3-C.sub.8alkenyl,
[0223] C.sub.3-C.sub.6alkynyl,
[0224] OR.sub.17,
[0225] NR.sub.18SR.sub.19,
[0226] C(O)R.sub.28 or
[0227] C(O)OR.sub.29;
[0228] Z is 0;
[0229] R.sub.14 is C.sub.1-C.sub.4alkyl;
[0230] R.sub.2 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.2-C.sub.6alkoxyalk- yl or
C.sub.3-C.sub.6-alkoxycarbonylalkyl;
[0231] R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.2-C.sub.6alkoxyalk- yl,
C.sub.2-C.sub.6haloalkoxyalkyl,
C.sub.3-C.sub.6alkoxycarbonylalkyl,
[0232] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0233] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4-haloalkoxy groups;
[0234] R.sub.4 and R.sub.5 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
[0235] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0236] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups, and
[0237] when R.sub.4 and R.sub.5 are taken together with the atom to
which they are attached, they represent a ring in which
R.sub.4R.sub.5 is a C.sub.2-C.sub.6alkylene group;
[0238] R.sub.6 is hydrogen, C.sub.1-C.sub.6alkyl or benzyl;
[0239] R.sub.7 and R.sub.8 are each independently hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxycarbonylalkyl;
[0240] R.sub.17 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.2-.sub.6alkoxyalkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6-hydroxycarbonylalkyl,
[0241] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or
[0242] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one or two cyano groups,
one or two nitro groups, one to three C.sub.1-C.sub.4alkyl groups,
one to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0243] R.sub.9 and R.sub.10 are each independently hydrogen,
C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6alkoxycarbonylalkyl, and
[0244] when R.sub.9 and R.sub.10 are taken together with the atom
to which they are attached, they represent a ring in which
R.sub.9R.sub.10 is a C.sub.2-C.sub.6alkylene group;
[0245] R.sub.18 and R.sub.19 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6alkoxycarbonylalkyl,
C.sub.2-C.sub.6hydroxycarbonylalkyl,
C.sub.2-C.sub.6alkylsulfonylalkyl,
C.sub.2-C.sub.6haloalkylsulfonylalkyl, or
[0246] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, and
[0247] when R.sub.18 and R.sub.19 are taken together with the atom
to which they are attached, they represent a ring in which
R.sub.18R.sub.19 is a C.sub.2-C.sub.6alkylene group;
[0248] R.sub.12 and R.sub.15 are each independently hydrogen or
C.sub.1-C.sub.6alkyl;
[0249] R.sub.13 and R.sub.16 are each independently
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl,
C.sub.3-C.sub.7cycloalkyl, C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6haloalkenyl, C.sub.3-C.sub.6alkynyl,
C.sub.3-C.sub.6haloalkynyl, or
[0250] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0251] R.sub.28 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalky- l, C.sub.3-C.sub.6alkenyl
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6alkoxycar- bonylalkyl,
or
[0252] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0253] R.sub.29 is hydrogen, C.sub.1-C.sub.6alkyl or benzyl;
[0254] A is --O--, --S(O).sub.r-- or --NR.sub.34--;
[0255] B is --CR.sub.37R.sub.38-- or
--C(.dbd.CR.sub.41R.sub.42)--;
[0256] R.sub.34 is hydrogen,
[0257] C.sub.1-C.sub.6alkyl optionally substituted with one or two
C(O)OR.sub.3 groups or one or two C(O)NR.sub.4R.sub.5 groups,
[0258] C.sub.3-C.sub.6alkenyl,
[0259] C.sub.3-C.sub.6alkynyl,
[0260] phenyl optionally substituted with any combination of one to
three halogen atoms, one to three C.sub.1-C.sub.4alkyl groups, one
to three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6-alkoxyalkyl groups, one or two nitro groups, one or
two cyano groups, one C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6-alkoxycarbonylalk- yl group or one
C.sub.3-C.sub.6alkylcarbonylalkyl group, or
[0261] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0262] R.sub.37 and R.sub.38 are each independently hydrogen,
halogen, C.sub.1-C.sub.6alkyl optionally substituted with one or
two cyano groups, one or two C(O)R.sub.2 groups, one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two P(O)(OR.sub.6).sub.2 groups, one or two OR.sub.7 groups or one
or two NR.sub.9R.sub.10 groups,
[0263] C.sub.3-C.sub.7cycloalkyl,
[0264] C.sub.3-C.sub.6alkenyl,
[0265] C.sub.3-C.sub.6alkynyl,
[0266] C(O)NR.sub.12S (O).sub.nR.sub.13, or
[0267] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4alkoxy groups, one to three
C.sub.1-C.sub.4haloalkoxy groups, one or two
C.sub.2-C.sub.6alkoxyalkyl groups, one
C.sub.2-C.sub.6alkoxycarbonyl group, one
C.sub.2-C.sub.6alkylcarbonyl group, one
C.sub.3-C.sub.6alkoxycarbonylalky- l group or one
C.sub.3-C.sub.6alkylcarbonylalkyl group, and
[0268] when R.sub.37 and R.sub.38 are taken together with the atom
to which they are attached, they represent a ring in which
R.sub.37R.sub.38 is a C.sub.2-C.sub.6alkylene group;
[0269] R.sub.41 and R.sub.42 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkylcarbonyl,
C.sub.2-C.sub.6alkoxycarbonyl, hydroxycarbonyl, or
[0270] phenyl optionally substituted with any combination of one to
three halogen atoms, one or two cyano groups, one or two nitro
groups, one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups;
[0271] r is an integer of 0, 1 or 2;
[0272] n and p are each independently an integer of 2; and
[0273] Q is selected from 6
[0274] Most preferred formula I herbicidal agents of this invention
are those wherein
[0275] X is fluorine;
[0276] Y is chlorine;
[0277] R is C.sub.1-C.sub.8alkyl optionally substituted with any
combination of one or two C(O)OR.sub.3 groups, one or two
C(O)NR.sub.4R.sub.5 groups, one or two P(O)(OR.sub.6).sub.2 groups,
one or two OR.sub.7 groups, one or two SR.sub.8 groups, one or two
NR.sub.9R.sub.10 groups, one or two C(O)NR.sub.12S(O)R.sub.13
groups or
[0278] one phenyl group optionally substituted with any combination
of one to three C.sub.1-C.sub.4alkyl groups or one to three
C.sub.1-C.sub.4alkoxy groups,
[0279] phenyl optionally substituted with any combination of one to
three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups, one or two
C.sub.2-C.sub.6oalkoxyalkyl groups, one or two
C.sub.3-C.sub.6alkoxycarbonylalkyl groups or one or two
NR.sub.15S(O).sub.pR.sub.16 groups,
[0280] C.sub.3-C.sub.8alkenyl or
[0281] C.sub.3-C.sub.8alkynyl;
[0282] Z is 0;
[0283] R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl,
C.sub.1-C.sub.6haloalkyl- , C.sub.3-C.sub.6alkenyl,
C.sub.3-C.sub.6alkynyl, C.sub.3-C.sub.6alkoxycar- bonylalkyl,
phenyl optionally substituted with any combination of one to three
halogen atoms, one or two cyano groups, one or two nitro groups,
one to three C.sub.1-C.sub.4alkyl groups, one to three
C.sub.1-C.sub.4haloalkyl groups, one to three C.sub.1-C.sub.4alkoxy
groups or one to three C.sub.1-C.sub.4haloalkoxy groups, or benzyl
optionally substituted on the phenyl ring with any combination of
one to three halogen atoms, one or two cyano groups, one or two
nitro groups, one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4haloalkyl groups, one to three
C.sub.1-C.sub.4alkoxy groups or one to three
C.sub.1-C.sub.4-haloalkoxy groups;
[0284] R.sub.4 and R.sub.5 are each independently hydrogen or
C.sub.1-C.sub.6alkyl, and when R.sub.4 and R.sub.5 are taken
together with the atom to which they are attached, they represent a
ring in which R.sub.4R.sub.5 is a C.sub.2-C.sub.6alkylene
group;
[0285] R.sub.6 is hydrogen or C.sub.1-C.sub.6alkyl;
[0286] R.sub.7 and R.sub.8 are each independently hydrogen,
C.sub.1-C.sub.6alkyl C.sub.2-C.sub.6alkoxycarbonylalkyl or
C.sub.2-C.sub.6hydroxycarbonylalkyl;
[0287] R.sub.9 and R.sub.10 are each independently hydrogen,
C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6alkoxycarbonylalkyl, and
[0288] when R.sub.9 and R.sub.10 are taken together with the atom
to which they are attached, they represent a ring in which
R.sub.9R.sub.10 is a C.sub.2-C.sub.6alkylene group;
[0289] R.sub.12 and R.sub.15 are hydrogen;
[0290] R.sub.13 and R.sub.16 are each independently
C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, or
[0291] benzyl optionally substituted on the phenyl ring with any
combination of one to three halogen atoms, one to three
C.sub.1-C.sub.4alkyl groups, one to three C.sub.1-C.sub.4haloalkyl
groups, one to three C.sub.1-C.sub.4-alkoxy groups or one to three
C.sub.1-C.sub.4haloalkoxy groups;
[0292] A is --O-- or --S(O).sub.r--;
[0293] B is --CR.sub.37R.sub.38-- or
--C(.dbd.CR.sub.41R.sub.42)--;
[0294] R.sub.37 and R.sub.38 are each independently hydrogen,
halogen,
[0295] C.sub.1-C alkyl optionally substituted with one or two
C(O)OR.sub.3 groups, one or two C(O)NR.sub.4R.sub.5 groups, one or
two OR.sub.7 groups or one or two NR.sub.9R.sub.10 groups, or
[0296] benzyl optionally substituted on the phenyl ring with any
combination of one to three C.sub.1-C.sub.4alkyl groups, one to
three C.sub.1-C.sub.4alkoxy groups or one
C.sub.3-C.sub.6alkoxycarbonylalkyl group, and when R.sub.37 and
R.sub.38 are taken together with the atom to which they are
attached, they represent a ring in which R.sub.37R.sub.38 is a
C.sub.2-C.sub.6alkylene group;
[0297] R.sub.41 and R.sub.42 are each independently hydrogen,
C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6
alkoxycarbonyl or hydroxycarbonyl;
[0298] r is an integer of 0, 1 or 2;
[0299] n and p are each independently an integer of 2; and
[0300] Q is selected from 7
[0301] Formula I compounds of the present invention which are
particularly effective herbicidal agents include
[0302]
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]-
phenyl}-1-cyclohexene-1,2-dicarboximide;
[0303]
3-{4-chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amino]p-
henyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione;
[0304] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetat-
e;
[0305]
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-delta5,al-
pha-thiazolidineacetic acid, diethyl ester;
[0306] ethyl
5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-7-oxo-4-thia-6-azaspiro[2.-
4]heptane-6-acetate;
[0307]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-
-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester;
[0308] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-oxazolidineacetate-
;
[0309]
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolid-
ineacetic acid, L-;
[0310]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl methyl ester;
[0311]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl isopropyl ester;
[0312] ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
-thiazolidineacetate;
[0313] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-[(methylcarbamoyl)methyl-
]-4-oxo-3-thiazolidineacetate;
[0314]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl (2-propynyl) ester;
[0315] methyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidi-
neacetate;
[0316] isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazol-
idineacetate;
[0317] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, L-;
[0318]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl3-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl 2-fluoroethyl ester;
[0319] 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thi-
azolidineacetate;
[0320]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester;
[0321] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(hydroxyethyl)-4-oxo-3-t-
hiazolidineacetate;
[0322] allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetat-
e;
[0323] isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineac-
etate;
[0324]
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene)amin-
o]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
[0325] cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazol-
idineacetate;
[0326] ethyl
5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate;
[0327]
3-{4-chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinylidene)amino]-2-f-
luorophenyl}-l-methyl-6-(trifluoromethyl)-2,4(1H,3H)1-pyrimidinedione;
[0328]
3-{4-chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidinylid-
ene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
[0329]
3-{4-chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione;
[0330] ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate;
[0331]
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluoro-
phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
[0332] methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropi-
onate;
[0333] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, D-;
[0334] methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-.alpha.-(p-nitroben-
zyl)-3-thiazolidineacetate, L-;
[0335] ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-
-4-(trifluoromethyl)-1(2H)1-pyrimidinyl]-4-(fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate, L-; and
[0336] methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methy-
l-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-
-oxo-3-thiazolidineacetate, DL-, among others.
[0337] Exemplary of halogen hereinabove are fluorine, chlorine,
bromine and iodine. The terms haloalkyl, halocycloalkyl,
haloalkoxy, haloalkenyl, halocycloalkenyl and haloalkynyl as used
in the specification and claims designate an alkyl group, a
cycloalkyl group, an alkoxy group, an alkenyl group, a cycloalkenyl
group and an alkynyl group substituted with one or more halogen
atoms, respectively. In formula I above, alkali metals include:
sodium, potassium and lithium. Alkaline earth metals of formula I
include magnesium and calcium. Further, the term organic ammonium
is defined as a group consisting of a positively charged nitrogen
atom joined to from one to four aliphatic groups, each containing
from one to sixteen carbon atoms.
[0338] In formula I above, 4- to 10-membered heterocyclic rings
include, but are not limited to, 1,2,4-triazole, 1,3,4-thiadiazole,
1,3,5-triazine, 2-thiazoline, benzimidazole, benzofuran,
benzothiophene, coumarin, furan, imidazole, imidazoline-2-thione,
indole, isatoic anhydride, isoquinoline, isoxazole, morpholine,
oxazole, piperazine, piperidine, purine, pyrazine, pyrazole,
pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidine, quinoline,
tetrahydrofuran, tetrahydrothiophene, thiazole and thiophene rings,
wherein each ring is optionally substituted as described
hereinabove for formula I.
[0339] The formula I compounds of the present invention are
effective herbicidal agents useful for the control of a wide
variety of undesirable plant species. Those compounds are effective
for controlling weeds native to both dry land and wet land areas.
The compounds are effective in controlling the above-said plants
when applied to the foliage thereof or to the soil or water
containing seeds or other propagating organs thereof such as
stolons, tubers or rhizomes, at rates of from about 0.01 kg/ha to 4
kg/ha and preferably from about 0.01 kg/ha to 1 kg/ha.
[0340] The compounds of this invention are best suited for use as
broad spectrum herbicides. However, certain compounds of this
invention are selective in soybeans and/or cereal crops such as
corn, wheat and rice when applied as preemergence and/or
postemergence treatments.
[0341] In addition, it has been found that the formula I compounds
of this invention may be used for the selective control of
undesirable plant species in transplanted rice culture by applying
a herbicidally effective amount of a formula I compound to the soil
or water containing seeds or other propagating organs of said
undesirable plant species after the rice has been transplanted.
[0342] Formula I compounds of this invention which are especially
useful for the selective control of undesirable plant species in
the presence of corn include
[0343]
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)amino]-
phenyl}-1-cyclohexene-1,2-dicarboximide;
[0344] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetat-
e;
[0345]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester;
[0346]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl methyl ester;
[0347]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl isopropyl ester;
[0348] ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
-thiazolidineacetate;
[0349]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl (2-propynyl) ester;
[0350] isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazol-
idineacetate;
[0351] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, L-;
[0352]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl 2-fluoroethyl ester;
[0353] 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thi-
azolidine-acetate; and
[0354]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester, among others.
[0355] Formula I compounds of the present invention which are
particularly useful for the selective control of undesirable plant
species in the presence of wheat include
[0356]
3-(carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-deltas,al-
pha-thiazolidineacetic acid, diethyl ester;
[0357]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl methyl ester;
[0358]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl isopropyl ester;
[0359] ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
-thiazolidineacetate; ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-
-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-[(methylc-
arbamoyl)methyl]-4-oxo-3-thiazolidineacetate;
[0360]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl (2-propynyl) ester;
[0361] isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazol-
idineacetate;
[0362] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, L-;
[0363]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl 2-fluoroethyl ester;
[0364] 2-fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimi-dinyl]-4-fluorophenyl}imino}-4-oxo-5-th-
iazolidineacetate;
[0365]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester;
[0366] ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(hydroxyethyl)-4-oxo-3-t-
hiazolidineacetate; and
[0367] cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazol-
idineacetate, among others.
[0368] Formula I compounds of this invention which are particularly
useful for the selective control of undesirable plant species in
the presence of transplanted rice include
[0369] ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate;
[0370]
3-{5-[(3-benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluoro-
phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
[0371] methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropi-
onate;
[0372] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, L-;
[0373] methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate, D-;
[0374] methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorom-
ethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-.alpha.-(p-nitroben-
zyl)-3-thiazolidineacetate, L-;
[0375] ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-
-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thia-
zolidineacetate, L- and
[0376] methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-methy-
l-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-
-oxo-3-thiazolidineacetate, DL-, among others.
[0377] Formula I compounds of this invention which are particularly
useful for the selective control of undesirable plant species in
the presence of soybeans include
[0378] ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
-thiazolidineacetate;
[0379]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl 2-fluoroethyl ester;
[0380]
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)--
1(2H)-pyrimidinyl]-4-fluorophenyl}-imino}-4-oxo-3,5-oxazolidinediacetic
acid, 3-ethyl ester;
[0381] allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]
-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineaceta- te; and
[0382]
3-{4-chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thia-zolidinylidene)ami-
no]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione,
among others.
[0383] While the compounds of this invention are effective for
controlling undesirable plant species when employed alone, they may
also be used in combination with or in conjunction with one or more
other biological chemicals, including herbicides.
[0384] The compounds of this invention may be applied to the
foliage of undesirable plant species or to the soil or water
containing seeds or other propagating organs thereof in the form of
a solid or liquid herbicidal composition, comprising a herbicidally
effective amount of the desired compound dispersed or dissolved in
an agronomically acceptable, inert solid or liquid carrier. The
compositions may be applied as preemergence or postemergence
treatments.
[0385] The formula I compounds of the present invention may be
formulated as emulsifiable concentrates, wettable powders, granular
formulations, suspension concentrates, flowable concentrates and
the like.
[0386] Formula I compounds wherein Q is Q1, Q2, Q3, Q5, Q6, Q7, Q9,
Q10, Q11, Q12, Q13, Q14, Q16, Q17, Q18, Q19, Q20, Q22, Q24 and Q25
may be prepared from 1-(3-aminophenyl)-isothiourea, -isourea,
-guanidine and -amidine compounds of formula II 8
[0387] wherein A, B, R, X, Y and Z are as described hereinabove,
using essentially the same procedures as described in U.S. Pat. No.
5,523,278.
[0388] Formula I compounds wherein Q is Q8 may be prepared by
reacting an amine of formula II with a substituted tetrahydrofuran
of formula III as shown below in Flow Diagram I. 9
[0389] Formula I compounds wherein Q is Q4 may be prepared from
formula I compounds wherein Q is Q8 using essentially the same
procedures used to prepare formula I compounds wherein Q is Q3 from
formula I compounds wherein Q is Q7.
[0390] Compounds of formula I wherein Q is Q15 may be prepared by
reacting an amine of formula II with a substituted tetrahydrofuran
of formula III to form an acid-amide of formula IV, and dehydrating
the acid-amide with a dehydrating agent such as
1,3-dicyclohexyl-carbodiimide. The reaction scheme is shown below
in Flow Diagram II. 10
[0391] Formula I compounds wherein Q is Q21 may be prepared from
formula I compounds wherein Q is Q8 using essentially the same
procedure used to prepare formula I compounds wherein Q is Q20 from
formula I compounds wherein Q is Q7.
[0392] Compounds of formula I wherein Q is Q23 may be prepared by
converting an amine of formula II to its corresponding isocyanate
of formula V using standard methods such as phosgene in an inert
solvent or palladium chloride and carbon monoxide, reacting the
formula V compound with a substituted hydrazine of formula VI to
form an intermediate compound of formula VII, and reacting the
formula VII compound with an ester of formula VIII. The reaction
scheme is shown in Flow Diagram III. 11
[0393] Formula I compounds wherein Q is Q26 may be prepared by
reacting an amine of formula II with a .beta.-aminoacrylic acid
chloride of formula IX to form an intermediate compound of formula
X, and reacting the intermediate compound with an acid chloride of
formula XI. The reaction scheme is shown in Flow Diagram IV. 12
[0394] Compounds of formula I wherein Q is Q27 may be prepared by
reacting an amine of formula II with an acid chloride of formula
XII to form an intermediate compound of formula XIII, and reacting
the intermediate compound (after deprotection) with an acid
chloride of formula XI. The reaction sequence is shown below in
Flow Diagram V. 13
[0395] Formula I compounds wherein Q is Q28 may be prepared by
reacting an amine of formula II with an unsaturated lactone of
formula XIV as shown below in Flow Diagram VI. 14
[0396] Similarly, formula I compounds wherein Q is Q29 may be
prepared by reacting an amine of formula II with a lactone of
formula XV. The reaction scheme is shown in Flow Diagram VII.
15
[0397] Compounds of formula I wherein Q is Q30 may be prepared, as
shown in Flow Diagram VIII, by reacting an isocyanate or
isothiocyanate of formula XVI with an unsaturated lactone of
formula XVII at an elevated temperature. 16
[0398] Similarly, formula I compounds wherein Q is Q31 may be
prepared by reacting an isocyanate or isothiocyanate of formula XVI
with a lactone of formula XVIII at an elevated temperature. The
reaction scheme is shown in Flow Diagram IX. 17
[0399] Formula I compounds wherein Q is Q32 may be prepared, as
shown in Flow Diagram X, by reacting an amine of formula II with
sodium isocyanate or sodium isothiocyanate to form a urea of
formula XIX, reacting the urea with a malonic acid diester of
formula XX to form an intermediate compound of formula XXI, and
reacting the intermediate compound with a phosphorus oxyhalide to
form a formula I compound wherein Q is Q32 and E is halogen, and
optionally reacting the formula I compound wherein Q is Q32 and E
is halogen with a C.sub.1-C.sub.4-alkyl sulfide or a
C.sub.1-C.sub.4alkoxide to form a formula I compound wherein Q is
Q32 and E is C.sub.1-C.sub.4alkylthio or C.sub.1-C.sub.4alkoxy,
respectively. 18
[0400] Compounds of formula I wherein Q is Q33 may be prepared, as
shown in Flow Diagram XI, by acylating a compound of formula XXII
with acetyl chloride and aluminum chloride to form an acetophenone
of formula XXIII, reacting the acetophenone compound with an ester
of formula XXIV in the presence of a base to form a diketone
compound of formula XXV, reacting the formula XXV compound with a
substituted hydrazine of formula XXVI to form an intermediate
compound of formula XXVII, and halogenating the formula XXVII
compound with a halogenating agent such as phosphorus oxychloride
to form a formula I compound wherein Q is Q33 and E is halogen, and
optionally reacting the formula I compound wherein Q is Q33 and E
is halogen with a C.sub.1-C.sub.4alkyl sulfide or a
C.sub.1-C.sub.4-alkoxide to form a formula I compound wherein Q is
Q33 and E is C.sub.1-C.sub.4alkylthio or C.sub.1-C.sub.4alkoxy,
respectively. 19
[0401] Formula I compounds wherein Q is Q34 may be prepared, as
shown in Flow Diagram XII, by reacting an isocyanate or
isothiocyanate of formula XVI with a substituted hydrazine of
formula XXVIII to form an intermediate compound of formula XXIX,
and reacting the formula XXIX compound with an acetal of formula
XXX at an elevated temperature. 20
[0402] Compounds of formula I wherein Q is Q35 may be prepared by
reacting a cyano compound of formula XXXI with a substituted
hydrazine of formula XXVI to form an intermediate compound of
formula XXXII, and reacting the intermediate compound with an acid
chloride of formula XXXIII. The reaction scheme is show in Flow
Diagram XIII. 21
[0403] Formula I compounds wherein Q is Q36 may be prepared, as
shown in Flow Diagram XIV, by reacting an isothiocyanate of formula
XXXIV with an amine of formula XXXV to form a thiourea of formula
XXXVI, and reacting the thiourea with an .alpha.-haloketone of
formula XXXVII. 22
[0404] Compounds of formula II wherein Q is Q37 may be prepared, as
shown below in Flow Diagram XV, by reacting a urea or thiourea of
formula XXXVIII with an acid chloride of formula XXXIX. 23
[0405] Formula I compounds wherein Q is Q38 may be prepared by
reacting an amine of formula II with a chloride compound of formula
XL to form an intermediate compound of formula XLI, and reacting
the intermediate compound with hydrogen sulfide, hydrogen chloride
and sodium periodate. The reaction scheme is shown in Flow Diagram
XVI. 24
[0406] Compounds of formula I wherein Q is Q39 may be prepared by
diazotizing an amine of formula II using conventional methods to
form an intermediate compound, reducing the intermediate compound
with sodium sulfite to form a hydrazine of formula XLII,
sequentially reacting the hydrazine with an acid chloride of
formula XLIII and phosphorous pentasulfide to form a substituted
hydrazine of formula XLIV, and reacting the formula XLIV compound
with phosgene or thiophosgene. The reaction scheme is shown in Flow
Diagram XVII. 25
[0407] Certain formula II compounds wherein A is S, Z is O, and B
is CR.sub.17R.sub.38 may be prepared by reacting an aniline of
formula XLV with nitric acid and sulfuric acid to form a
3-nitroaniline of formula XLVI, reacting the 3-nitroaniline with
thiophosgene to form an isothiocyanate of formula XLVII, reacting
the isothiocyanate with an amine of formula XLVIII to form a
thiourea of formula XLIX, reacting the thiourea with an
.alpha.-halo ester of formula L optionally in the presence of a
base to form an intermediate compound of formula LI, and reducing
the formula LI compound using conventional procedures. The reaction
scheme is shown below in Flow Diagram XVIII. 26
[0408] Certain formula II compounds wherein A is S, Z is O, B is
--C(.dbd.T)--, and T is O may be prepared, as shown in Flow Diagram
XIX, by reacting a thiourea of formula XLIX with oxalyl chloride to
form an intermediate compound of formula LII, and reducing the
formula LII compound using conventional procedures. 27
[0409] Certain compounds of formula II wherein A is S, B is
--C(.dbd.CR.sub.41R.sub.42)--, and Z is O may be prepared, as show
in Flow Diagram XX, by reacting a thiourea of formula XLIX with an
.alpha.-halo ester of formula LIII to form a compound of formula
LIV, reacting the formula LIV compound with a ketone or aldehyde of
formula LV in the presence of a base to form a compound of formula
LVI, and reducing the formula LVI compound using conventional
procedures. 28
[0410] Certain formula II compounds wherein A is O, S or NR.sub.34,
B is CR.sub.37R.sub.38 and Z is O may be prepared by reacting a
thiourea of formula XLIX with triethylamine, methanesulfonyl
chloride and 4-dimethylaminopyridine to form a compound of formula
LVII, cyclizing the formula LVII compound with an ester compound of
formula-LVIII in the presence of copper(I)chloride when A is O to
form a compound of formula LIX, and reducing the formula LIX
compound using conventional procedures. The reaction scheme is
shown below in Flow Diagram XXI. 29
[0411] Formula II compounds wherein B is
--C(.dbd.CR.sub.42R.sub.43)-- and Z is O may be prepared, as shown
in Flow Diagram XXII, by reacting a formula LIX compound wherein
R.sub.37 and R.sub.38 are hydrogen with a ketone or aldehyde of
formula LV in the presence of a base to form an intermediate
compound of formula LX, and reducing the intermediate compound
using conventional procedures. 30
[0412] Alternatively, compounds of formula XLIX may be prepared as
shown below in Flow Diagram XXIII. 31
[0413] Intermediate compounds of formula LIX may also be prepared
as shown below in Flow Diagram XXIV. 32
[0414] Formula I compounds wherein Q is Q24, A is S, and B is
CR.sub.37R.sub.38 may also be prepared as shown below in Flow
Diagram XXV. 33
[0415] Alternatively, one of the intermediates used in the reaction
scheme described in Flow Diagram XXV may be prepared as shown below
in Flow Diagram XXVI. 34
[0416] Formula I compounds wherein A is S, B is CR.sub.37R.sub.38,
Z is C, and Q is Q1-Q32, Q34 and Q36-Q39 may also be prepared by
substituting an aniline of formula LXI or a 3-nitroaniline of
formula LXII for the formula II amines used hereinabove to obtain
compounds of formula LXIII, and converting the formula LXIII
compounds to the desired formula I compounds as shown below in Flow
Diagram XXVII. 35
[0417] Alternatively, certain formula I compounds wherein Q is
Q1-Q32, Q34 and Q36-Q39, B is CR.sub.37R.sub.38, and Z is O may be
prepared, as shown below in Flow Diagram XXVIII, by reacting a
thiourea of formula LXIV with methanesulfonyl chloride,
triethylamine and 4-dimethylaminopyridine to form an intermediate
compound of formula LXV, and reacting the intermediate compound
with an ester of formula LVIII and copper(I)chloride when A is O.
36
[0418] Compounds of formula I wherein A is S, B is --C(.dbd.T)--,
and T and Z are O may be prepared, as shown in Flow Diagram XXIX,
by reacting a thiourea of formula LXIV with oxalyl chloride. 37
[0419] Formula I compounds wherein A is S, B is
--C(.dbd.CR.sub.41R.sub.42- )--, and Z is O may be prepared as
shown below in Flow Diagram XXX. 38
[0420] Compounds of formula I wherein R is NR.sub.18R.sub.19, A is
S, B is CR.sub.37R.sub.38, and Z is O may be prepared, as shown in
Flow Diagram XXXI, by reacting an isothiocyanate of formula LXVI
with a hydrazine of formula LXVII to form a thiourea of formula
LXVIII and reacting the thiourea with an .alpha.-halo ester of
formula L optionally in the presence of a base. 39
[0421] Alternatively, formula I compounds wherein R is
NR.sub.18R.sub.19 may be prepared as shown below in Flow Diagram
XXXII. 40
[0422] Formula I compounds wherein R is OR.sub.17, may be prepared,
as shown in Flow Diagram XXXIII, by reacting an isocyanate of
formula LXVI with an amine of formula LXIX to form a thiourea of
formula LXX, and reacting the thiourea with an .alpha.-halo ester
of formula L. 41
[0423] Formula I compounds wherein Q is Q24 and R.sub.46 is
hydrogen may be prepared as shown below in Flow Diagram XXXIV.
42
[0424] Other methods for the preparation of formula I compounds
will become apparent from the examples set forth below. In
addition, certain compounds of formula I may be converted into
other compounds of formula I by using conventional procedures known
to those skilled in the art.
[0425] The present invention also relates to intermediate compounds
having the structural formula LXXI 43
[0426] wherein
[0427] U is --N.dbd.C.dbd.NR, --N.dbd.C.dbd.S 44
[0428] Q is Q5, Q7, Q24 or Q29 as described hereinabove; and
[0429] R, X and Y are as described hereinabove.
[0430] Preferred formula LXXI compounds are those wherein
[0431] U is --N.dbd.C.dbd.NR, --N.dbd.C.dbd.S 45
[0432] Q is 46
[0433] X is hydrogen, fluorine or chlorine;
[0434] Y is fluorine, chlorine, nitro or cyano; and
[0435] R is hydrogen,
[0436] C.sub.1-C.sub.6alkyl optionally substituted with one to
three halogen atoms, one or two C(O)OR.sub.3 groups, one cyano
group, one OR.sub.7 group, one SR.sub.8 group, one
P(O)(OR.sub.6).sub.2 group, or
[0437] a C.sub.3-C.sub.6alkenyl, C.sub.3-C.sub.6alkynyl, phenyl,
benzyl or furfural group, wherein each group is optionally
substituted with one to three halogen atoms, one
C.sub.1-C.sub.3alkoxy group or one C(O)OR.sub.3 group;
[0438] R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl or
C.sub.1-C.sub.6haloalkyl;
[0439] R.sub.6 is hydrogen or C.sub.1-C.sub.6alkyl;
[0440] R.sub.7 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonylalkyl; and
[0441] R.sub.8 is hydrogen, C.sub.1-C.sub.3alkyl or
C.sub.3-C.sub.6alkoxycarbonyl.
[0442] In order to facilitate a further understanding of the
invention, following examples are presented to illustrate more
specific details thereof. This invention is not to be limited
thereby except as defined in the claims.
EXAMPLE 1
Preparation of 4-Chloro-2-fluoro-5-nitroaniline
[0443] 47
[0444] A solution of 4-chloro-2-fluoroaniline (10.0 g, 69 mmol) in
concentrated sulfuric acid is cooled to -20.degree. C., treated
dropwise with 90% nitric acid (5.0 mL, 107 mmol) over ten minutes,
stirred at -15.degree. C. for 90 minutes, and poured onto ice. The
resultant aqueous mixture is extracted with diethyl ether,
neutralized with 50% sodium hydroxide solution, and extracted again
with diethyl ether. The organic extracts are combined, washed
sequentially with dilute sodium hydroxide solution and brine, dried
over anhydrous magnesium sulfate, and concentrated in vacuo to give
the title product as a brown solid (11.3 g, 86% yield, mp
82-83.5.degree. C.) which is identified by .sup.1H, .sup.19F and
.sup.13C NMR spectral analyses.
[0445] Using essentially the same procedure, but substituting
2,4-dichloroaniline for 4-chloro-2-fluoroaniline,
2,4-dichloro-5-nitroani- line is obtained.
EXAMPLE 2
Preparation of
3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-2,4-
(1H,3H)-pyrimidinedione
[0446] 48
[0447] A solution of 4-chloro-2-fluoro-5-nitroaniline (5.0 g, 26.3
mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one
(5.73 g, 27.6 mmol) in acetic acid is refluxed for 4 hours and
poured onto ice. The resultant aqueous mixture is filtered to
obtain a solid. The solid is washed with water and air-dried to
give the title product as a beige solid (7.5 g, 81% yield, mp
230-232.degree. C.) which is identified by .sup.1H, 13C and
.sup.19F NMR spectral analyses.
[0448] Using essentially the same procedure, but substituting
2,4-dichloro-5-nitroaniline for 4-chloro-2-fluoro-5-nitroaniline,
3-(2,4-dichloro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione, mp 188.5-190.degree. C., is obtained.
EXAMPLE 3
Preparation of
3-(4-Chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluorome-
thyl)-2,4(1H,3H)-pyrimidinedione
[0449] 49
[0450] A solution of
3-(4-chloro-2-fluoro-5-nitrophenyl)-6-trifluoromethyl- )-2,4
(1H,3H)-pyrimidinedione (5.66 g, 16 mmol) in N,N-dimethylformamide
is treated sequentially with potassium carbonate (2.43 g, 17.6
mmol) and iodomethane (1.1 mL, 17.6 mmol), stirred overnight at
room temperature, and poured into water. After acidifying the
resultant aqueous mixture to pH 5, the solids are collected, washed
with water and dried to obtain a dark, brown solid. The solid is
dissolved in methylene chloride and the resultant solution is
washed sequentially with water and brine, passed through a silica
gel plug, and concentrated in vacuo to give the title product as a
light, brown solid (4.7 g, 80% yield, mp 124-126.5.degree. C.)
which is identified by .sup.1H and .sup.13C NMR spectral
analyses.
[0451] Using essentially the same procedure, but substituting
3-(2,4-dichloro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione for
3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H-
)-pyrimidinedione,
3-(2,4-dichloro-5-nitrophenyl)-1-methyl-6-(trifluoromet-
hyl)-2,4(1H,3H)-pyrimidinedione, mp 127-128.5.degree. C., is
obtained.
EXAMPLE 4
Preparation of
3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluorome-
thyl)-2,4(1H,3H)-pyrimidinedione
[0452] 50
[0453] A solution of
3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifl-
uoromethyl)-2,4(1H,3H)-pyrimidinedione (3.00 g, 8.16 mmol) in
acetic acid is heated to 50-60.degree. C., treated portionwise with
iron powder (2.28 g, 40.8 mmol) over 10 minutes, stirred at
50-60.degree. C. for 90 minutes, cooled to room temperature, and
diluted with water. The resultant aqueous mixture is filtered to
remove solids and extracted with diethyl ether. The organic
extracts are combined, washed sequentially with 1 M sodium
hydroxide solution and brine, dried over anhydrous magnesium
sulfate, and concentrated in vacuo to give the title product as a
brown solid (2.37 g, 86% yield, mp 132-135.degree. C.) which is
identified by .sup.1H and 13C NMR spectral analyses.
[0454] Using essentially the same procedure, but substituting
3-(2,4-dichloro-5-nitrophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-py-
rimidinedione for
3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluor-
omethyl)-2,4(1H,3H)-pyrimidinedione,
3-(5-amino-2,4-dichlorophenyl)-1-meth-
yl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione, mp
163-165.degree. C., is obtained.
EXAMPLE 5
Preparation of
N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide
[0455] 51
[0456] A solution of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol)
and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in
acetic acid is refluxed for 2 hours, treated with additional
4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred
at room temperature overnight and poured into water. The resultant
aqueous mixture is extracted with ethyl acetate. The organic
extract is washed sequentially with water, saturated sodium
hydrogen carbonate solution and brine, dried over anhydrous
magnesium sulfate, and concentrated in vacuo to obtain a purple
oil. Flash column chromatography of the oil using silica gel and 15
to 20% ethyl acetate in hexanes solutions gives the title product
as an off-white solid (25.3 g, 69% yield, mp 81-82.degree. C.)
which is identified by .sup.1H, 13C and .sup.19F NMR spectral
analyses.
EXAMPLE 6
Preparation of
N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicar-
boximide
[0457] 52
[0458] A mixture of
N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarbox- imide (24.4
g, 86.7 mmol) in sulfuric acid is cooled to -3.degree. C., treated
dropwise with 70% nitric acid (6.7 mL, 104.0 mmol) while
maintaining the temperature from 0.degree. to 2.degree. C., warmed
to and stirred at room temperature for 90 minutes, and poured onto
ice. The resultant aqueous mixture is filtered to obtain a solid.
The solid is washed with water and air-dried overnight to give the
title product as a white powder (28.68 g, mp 152-155.degree. C.)
which is identified by .sup.1H, .sup.13C and .sup.19F NMR spectral
analyses.
EXAMPLE 7
Preparation of
N-(5-amino-4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicar-
boximide
[0459] 53
[0460] A mixture of
N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2--
dicarboximide (10.6 g, 32.7 mmol) in acetic acid is heated to
65.degree. C., treated portionwise with iron powder (7.30 g, 130.7
mmol) over 40 minutes, stirred for 10 minutes, and filtered through
diatomaceous earth. The resultant filtrate is washed with ethyl
acetate, concentrated in vacuo, diluted with ethyl acetate and
saturated sodium hydrogen carbonate solution, and filtered through
a filter pad. The phases are separated and the organic phase is
washed sequentially with saturated sodium hydrogen carbonate
solution and brine, dried over anhydrous magnesium sulfate, and
concentrated in vacuo to give the title product as a yellow solid
(8.94 g, 94% yield, mp 164-165.degree. C.).
EXAMPLE 8
Preparation of
N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}(thiocarbamoyl)}glycine,
ethyl ester
[0461] 54
[0462] A solution of
3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifl-
uoromethyl)-2,4(1H,3H)-pyrimidinedione (3.0 g, 8.89 mmol) in a
tetrahydrofuran/ethanol solution (1:1) is treated with ethyl
isothiocyanatoacetate (1.93 g, 13.34 mmol), refluxed for 9 hours,
stirred at room temperature overnight, and concentrated in vacuo to
obtain an orange-brown gum. Flash column chromatography of the gum
using silica gel and 25% to 30% ethyl acetate in hexanes solutions
gives the title product as a white foam (2.24 g, 52% yield, mp
95-103.degree. C.) which is identified by .sup.1H, .sup.13C and
.sup.19F NMR spectral analyses.
[0463] Using essentially the same procedure, the following
compounds are obtained:
1 55 Q X R mp .degree. C. 56 F CH.sub.3 110-116 57 Cl
CH.sub.2CO.sub.2C.sub.2H.sub.5 218-219.5 58 F CH.sub.3 177-179
(dec) 59 F CH.sub.2CO.sub.2C.sub.2H.sub.5 87-94 60 F
CH.sub.2CH.dbd.CH.sub.2 83-91 61 F CH.sub.2CO.sub.2C.sub.2H.sub.5
160-162 62 F CH.sub.2CO.sub.2C.sub.2H.sub.5 foam 63 F 64 192-195 65
F 66 67 F (CH.sub.2).sub.3OCH.sub.3 171-172
EXAMPLE 9
Preparation of
2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanate
[0464] 68
[0465] A mixture of
3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(triflu-
oromethyl)-2,4(1H, 3H)-pyrimidinedione (1.0 g, 2.96 mmol) in
toluene is cooled to 0.degree. C., treated sequentially with
triethylamine (0.91 mL, 6.52 mmol) and thiophosgene (0.25 mL, 3.26
mmol), warmed to and stirred at room temperature for 5 hours, and
filtered to remove solids. The resultant filtrate is concentrated
in vacuo to give the title product as an orange solid (1.1 g, 98%
yield) which is identified by .sup.1H NMR spectral analysis.
EXAMPLE 10
Preparation of
N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1 (2H)-pyrimidinyl]
-4-fluoro-phenyl}(thiocarbamoyl)}-.beta.-alani- ne, methyl
ester
[0466] 69
[0467] A solution of
2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanate (6.0 g,
15.8 mmol) and .beta.-alanine, methyl ester, hydrochloride salt
(2.65 g, 19.0 mmol) in acetone is cooled to 0.degree. C., treated
dropwise with a solution of triethylamine (1.92 g, 19.0 mmol) in
methylene chloride, stirred overnight at room temperature, and
poured into water. The resultant aqueous mixture is extracted with
ethyl acetate. The organic extracts are combined, washed
sequentially with 5% hydrochloric acid and brine, dried over
anhydrous magnesium sulfate, and concentrated in vacuo to obtain a
brown foam. Flash column chromatography of the foam using silica
gel and a (9:1) methylene chloride/diethyl ether solution gives the
title product as an off-white foam (5.68 g, 74.4% yield, mp
110.degree. C.) which is identified by .sup.1H NMR spectral
analysis.
[0468] Using essentially the same procedure, but substituting the
appropriate amine for .beta.-alanine, methyl ester, hydrochloride
salt, the following compounds are obtained:
2 70 R mp .degree. C. CH.sub.2CO.sub.2CH.sub.3 173-174
(CH.sub.2).sub.3CO.sub.2CH.sub.3 182-185 71 100-106
CH.sub.2CO.sub.2C(CH.sub.3).sub.2 100-106 CH.sub.2C.dbd.CH.sub.2
196-199 (CH.sub.2).sub.2OCH.sub.3 153-155 C.sub.2H.sub.5 207-208
CH(CH.sub.3)C.ident.CH 163-165 (CH.sub.2).sub.2SCH.sub.3 glass
(CH.sub.2).sub.2SCH.sub.2CO.s- ub.2CH.sub.3 glass CH.sub.2CF.sub.3
glass CH(CH.sub.3).sub.2 235-238 72 223-225 73 225-228
(CH.sub.2).sub.2CH.sub.3 214-215 (CH.sub.2).sub.2F 159-160
EXAMPLE 11
Preparation of
3-{4-Chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene-
)amino]phenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione
[0469] 74
[0470] A solution of
1-{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-3-methyl-2-thiourea
(0.92 g, 2.24 mmol) in N,N-dimethylformamide is treated
sequentially with potassium carbonate (0.34 g, 2.47 mmol) and
methyl bromoacetate (3.2 mL, 3.36 mmol), stirred at room
temperature for 5.5 hours, and poured into water. The resultant
aqueous mixture is extracted with diethyl ether and ethyl acetate.
The organic extracts are combined, washed sequentially with water
and brine, dried over anhydrous magnesium sulfate, and concentrated
in vacuo to obtain a yellow oil. Flash column chromatography of the
oil using silica gel and a (1:2) ethyl acetate/hexanes solution
gives the title product as a pale, yellow solid (0.6 g, 59% yield,
mp 96-105.degree. C.) which is identified by .sup.1H, .sup.13C and
.sup.19F NMR spectral analyses.
[0471] Using essentially the same procedure, or alternatively
heating the reaction mixture in the absence of base, the following
compounds are obtained:
3 75 R R.sub.37 mp .degree. C. CH.sub.3 H 83-103
CH.sub.2CH.dbd.CH.sub.2 H 165-165 C.sub.6H.sub.5 H 175-180 CH.sub.3
CH.sub.3 91-97 CH.sub.3 F 80-95 CH.sub.3 C.sub.2H.sub.5 80-88
CH.sub.2CO.sub.2C.sub.2H.sub.5 H 92-100 76 X R J mp .degree. C. F
77 H 125-126 F 78 H 99-101 F (CH.sub.2).sub.2OCH.sub.3 H glass F
C.sub.2H.sub.5 H glass F CH(CH.sub.3)C.ident.CH H 118-121 F
(CH.sub.2).sub.3OCH.sub.3 H glass F CH.sub.2CO.sub.2C.sub.2H.sub.5
Br 82-84 F CH.sub.2CO.sub.2C.sub.2H.sub.5 CH.sub.2OCH.sub.3 158-159
F CH.sub.2CO.sub.2C.sub.2H.sub.5 SCH.sub.3 67-70 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 Cl 55-57 F CH.sub.2CO.sub.2C.sub.2H-
.sub.5 CO.sub.2C.sub.2H.sub.5 60-62 F
CH.sub.2CO.sub.2C.sub.2H.sub.- 5 CO.sub.2CH.sub.3 46-48 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 .dbd.CH.sub.2 207-208 F
(CH.sub.2).sub.2SCH.sub.3 H glass F
(CH.sub.2).sub.2SCH.sub.2CO.sub.2CH.sub.3 H glass F
CH.sub.2CO.sub.2C.sub.2H.sub.5 OCH.sub.3 84-86 F CH.sub.2CF.sub.3 H
135-138 F CH(CH.sub.3).sub.2 H 108-109 F 79 H 150-152 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 CO.sub.2CH(CH.sub.3).sub.2 75-77 F
80 H glass F (CH.sub.2).sub.2CH.sub.3 H glass F
(CH.sub.2).sub.2OCH.sub.3 H glass F (CH.sub.2).sub.2F H 156-158 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 H 85-95 F CH.sub.3 CH.sub.3 93-99 F
CH.sub.3 C.sub.2H.sub.5 78-84 F CH.sub.2CO.sub.2C.sub.2H.su- b.5 F
glass F CH.sub.2CO.sub.2C.sub.2H.sub.5 CH.sub.3 glass F
CH.sub.2CO.sub.2C.sub.2H.sub.5 C.sub.2H.sub.5 glass F
CH.sub.2CO.sub.2C.sub.2H.sub.5 spirocyc- glass lopropyl F
CH.sub.2CO.sub.2CH.sub.3 H glass F N(CH.sub.3).sub.2 H 192-193 F
CH.sub.2C.sub.6H.sub.5 H oil F CH.sub.2CH.dbd.CH.sub.2 H 64-68 F
CH.sub.2CH.sub.2CO.sub.2CH.sub.3 H oil F
(CH.sub.2).sub.3CO.sub.2CH.sub.3 H 65-70 Cl
CH.sub.2CO.sub.2C.sub.2H.sub.5 H 90-105 F 81 H foam F
CH.sub.2CO.sub.2C(CH.sub.3).sub.3 H 114-115 82 mp 60-70.degree. C.
and 83
EXAMPLE 12
Preparation of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester
[0472] 84
[0473] A solution of
N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}(thiocarbamoyl)}glycine,
ethyl ester (2.94 g, 6.2 mmol) and maleic anhydride (0.67 g, 6.8
mmol) in N,N-dimethylformamide is stirred at 80.degree. C. for 2
days, treated with additional maleic anhydride (0.67 g), stirred
overnight at 84.degree. C., and poured into an ice-water mixture.
The resultant aqueous mixture is filtered to obtain a solid. Column
chromatography of the solid using silica gel and a diethyl
ether/methylene chloride/hexanes acetic acid solution (33:33:33:1)
gives the title product as a pale, yellow glass (1.14 g) which is
identified by .sup.1H, .sup.13C and .sup.19F NMR spectral
analyses.
[0474] Using essentially the same procedure, the following
compounds are obtained:
4 85 Q X R mp .degree. C. 86 F CH.sub.2CH.dbd.CH.sub.2 87 F
CH.sub.3 88 Cl CH.sub.2CO.sub.2C.sub.2H.sub.5 104-120 89 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 170-174 90 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 170-174 91 F
CH.sub.2CO.sub.2C.sub.2H.sub.5 oil
EXAMPLE 13
Preparation of
3-(Carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-d-
elta5,alpha-thiazolidineacetic acid, diethyl ester
[0475] 92
[0476] A solution of
N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}(thiocarbamoyl)}glycine,
ethyl ester (3.0 g, 6.2 mmol) and diethyl acetylenedicarboxylate
(1.06 g, 6.2 mmol) in methanol is refluxed for 3 hours, cooled, and
concentrated in vacuo to obtain a glass. Column chromatography of
the glass using silica gel and a 3% ethyl acetate in methylene
chloride solution gives the title product as a yellow glass (2.49
g) which is identified by .sup.1H, .sup.13C and .sup.19F NMR
spectral analyses.
EXAMPLE 14
Preparation of
N-{{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}methylene}glycine,
ethyl ester
[0477] 93
[0478] A solution of
N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}(thiocarbamoyl)}glycine,
ethyl ester (5.0 g, 10.4 mmol) in methylene chloride is treated
sequentially with triethylamine (4.3 mL, 31.1 mmol),
4-dimethylamino-pyridine (0.05 g) and methanesulfonyl chloride (1.6
mL, 20.7 mmol) stirred at room temperature for 10 minutes, and
partially concentrated in vacuo to obtain a heterogeneous mixture.
The heterogeneous mixture is placed onto silica gel and eluted with
methylene chloride. The resultant solution is concentrated in vacuo
to give the title product as an amber syrup (4.68 g) which is
identified by .sup.1H and .sup.13C NMR spectral analyses.
EXAMPLE 15
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidin-
eacetate
[0479] 94
[0480] A solution of
N-{{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}methylene}glycine,
ethyl ester (0.63 g, 1.41 mmol)in methylene chloride is treated
with methyl glycolate (0.14 g), stirred for 90 minutes, treated
with copper(I) chloride (0.05 g), stirred at room temperature for
16 hours, refluxed for 5 hours, and filtered to remove solids. The
resultant filtrate is concentrated in vacuo to obtain an amber gum.
Flash column chromatography of the gum using silica gel and 20% to
25% ethyl acetate in hexanes solutions gives the title product as
an off-white foam (0.37 g, mp 67-87.degree. C.) which is identified
by .sup.1H and 13C NMR spectral analyses.
[0481] Using essentially the same procedure, the following
compounds are obtained:
5 95 A R.sub.37 mp .degree. C. NCH.sub.3 H 83-90
NCH.sub.2CO.sub.2C.sub.2H.sub.5 H 144-146 O
CH.sub.2CO.sub.2CH.sub.2C.sub.6H.sub.5 foam
EXAMPLE 16
Preparation of Methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl--
2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-o-
xo-3-thiazolidineacetate, L-
[0482] 96
[0483] A solution of
2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanate (0.38
g, 1.0 mmol) and N,N-diisopropylethylamine (1.0 mL) in
tetrahydrofuran is treated with L-phenylalanine, methyl ester,
hydrochloride (0.18 g, 1.0 mmol), shaken at 40.degree. C. for 1
hour, treated with methyl bromoacetate (0.46 g, 3.0 mmol), shaken
at 40.degree. C. for 16 hours, and concentrated in vacuo to obtain
a residue. Column chromatography of the residue using silica gel
and 0% to 10% diethyl ether in methylene chloride solutions gives
the title product (0.37 g) which is identified by .sup.1H and
.sup.13C NMR spectral analyses.
[0484] Using essentially the same procedure, the following
compounds are obtained:
6 97 R 98 CH(CH.sub.2C.sub.6H.sub.5)CO.sub.2CH.sub.3
CH(CH.sub.3)CO.sub.2C(CH.sub.3).sub.3 CH(CH.sub.3)CO.sub.2C.sub.2-
H.sub.5 CH(CH.sub.2C.sub.6H.sub.4-p-Cl)CO.sub.2CH.sub.3
CH(CH.sub.2C.sub.6H.sub.4-p-NO.sub.2)CO.sub.2CH.sub.3
CH(C.sub.6H.sub.4-p-Cl)CO.sub.2C.sub.2H.sub.5
CH(CH.sub.2C.sub.6H.sub.5)CO.sub.2C.sub.2H.sub.5 99
CH.sub.2C.sub.6H.sub.4-o-CH.sub.3 CH.sub.2C.sub.6H.sub.4-m-CH.sub.3
CH.sub.2C.sub.6H.sub.4-m-Cl CH.sub.2C.sub.6H.sub.4-m-OCH.sub.3
CH.sub.2C.sub.6H.sub.4-o-C- l CH.sub.2C.sub.6H.sub.4-m-CF.sub.3
CH.sub.2C.sub.6H.sub.4-p-CF.sub.3 CH.sub.2C.sub.6H.sub.4-p-Cl
CH.sub.2C.sub.6H.sub.4-p-Br CH.sub.2C.sub.6H.sub.4-p-F
CH.sub.2C.sub.6H.sub.4-p-SO.sub.2NH.sub.2
CH.sub.2C.sub.6H.sub.4-p-N(CH.sub.3).sub.2
CH.sub.2C.sub.6H.sub.3-3,4-di-Cl CH.sub.2C.sub.6H.sub.3-3,5-di-Cl
CH.sub.2C.sub.6H.sub.3-3,4-di-OCH.sub.3
CH.sub.2C.sub.6H.sub.3-2,4-di-OCH.sub.3 CH.sub.2C.sub.6H.sub.3-3,-
5-di-CH.sub.3 CH.sub.2C.sub.6H.sub.3-3,4-di-CH.sub.3
CH.sub.2C.sub.6H.sub.3-3-Cl-4-CH.sub.3 CH.sub.2C.sub.6H.sub.2-3,4-
,5-tri-OCH.sub.3 CH.sub.2-2-pyridyl CH.sub.2-3-pyridyl
CH.sub.2-4-pyridyl
EXAMPLE 17
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-.alpha.-methyl-4-oxo-3-t-
hiazolidineacetic acid, L-
[0485] 100
[0486] An alanine substituted resin (1.0 mmol) which is N-protected
with Fmoc and supported on polystyrene (commercially available as
Fmoc-gly-Wang resin from Midwest Bio-tech Inc., Fishers, Ind.) is
treated with a 20% piperdine in N,N-dimethylformamide solution to
remove the Fmoc protecting group. The solvents are removed and the
resin is washed with N,N-dimethylformamide, methanol and methylene
chloride, treated with a solution of
2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4-fluorophenyl isothiocyanate (0.57 g, 1.5
mmol) in methylene chloride, and stirred at room temperature for 6
hours. The solvents are removed and the resin is washed with
N,N-dimethylformamide, methanol and methylene chloride, diluted
with N,N-dimethylformamide, treated with methyl bromoacetate (0.46
g, 3 mmol) and N,N-diisopropylethylamine (1 ml), and stirred
overnight at room temperature. The solvents are removed and the
resultant resin is washed sequentially with N,N-dimethylformamide,
methanol and methylene chloride, air-dried, and cleaved with
trifluoroacetic acid. Column chromatography of the resultant
reaction mixture using silica gel and a 15% methanol in methylene
chloride solution gives the title product (0.55 g) which is
identified by .sup.1H and 13C NMR spectral analyses.
[0487] Using essentially the same procedure, the following
compounds are obtained:
7 101 R Stereochemistry CH.sub.2CO.sub.2H
CH(CH.sub.2C.sub.6H.sub.5)CO.su- b.2H L--
CH(CH.sub.2C.sub.6H.sub.5)CO.sub.2H D-- CH(CH.sub.3)CO.sub.2H D--
CH[CH.sub.2CH(CH.sub.3).sub.2]CO.sub.2H L--
EXAMPLE 18
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinedi-
acetic acid
[0488] 102
[0489] A solution of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
flurormethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinedia-
cetic acid, 3-ethyl ester (0.5 g, 0.9 mmol) in 10% hydrochloric
acid (1.4 mL) and acetic acid (5.6 mL) is stirred at 55.degree. C.
for 5 days, and concentrated in vacuo to obtain a yellow glass.
Column chromatography of the glass using silica gel and a 5%
methanol in methylene chloride solution gives the title product as
a white solid which is identified by .sup.1H NMR spectral
analysis.
[0490] Using essentially the same procedure, the following
compounds are obtained:
8 103 R mp .degree. C. CH.sub.2CH.sub.2CH.sub.2CO.sub.2H 140 (dec)
CH.sub.2CH.sub.2CO.sub.2H 135 (dec)
EXAMPLE 19
Preparation of Ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-met-
hyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-
-4-oxo-3-thiazolidineacetate
[0491] 104
[0492] A solution of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinedia-
cetic acid, 3-ethyl ester (0.5 g, 0.9 mmol) in methylene chloride
is treated with oxalyl chloride (0.5 mL), stirred at room
temperature for 2 hours, concentrated in vacuo, treated with a 0.5
M ammonia solution in dioxane (2 mL), stirred overnight at room
temperature, and concentrated in vacuo to obtain a residue.
Chromatography of the residue gives the title product which is
identified by .sup.1H NMR spectral analysis.
[0493] Using essentially the same procedure, the following
compounds are obtained:
9 105 R R.sub.37 CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.2C(O)NHCH.sub.3 CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.2C(O)NHCH(CH.sub.3).sub.2 CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.2C(O)NHC.sub.6H.sub.5 CH.sub.3 CH.sub.2C(O)NHC.sub.6H.sub.5
CH.sub.3 CH.sub.2C(O)NH.sub.2 CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.2C(O)OCH.sub.2C.ident.CH CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.2C(O)OCH.sub.2CH.sub.2F CH.sub.2CH.dbd.CH.sub.2
CH.sub.2C(O)NHCH.sub.3 CH.sub.2CH.dbd.CH.sub.2
CH.sub.2C(O)OCH.sub.2CH.sub.2F CH.sub.3 CH.sub.2C(O)OCH.sub.3
CH.sub.3 CH.sub.2C(O)OCH(CH.sub.3).sub.2 CH.sub.3
CH.sub.2C(O)OCH.sub.2C.ident.CH CH.sub.3 CH.sub.2C(O)OCH.sub.2CH.-
sub.2F CH.sub.2CH.dbd.CH.sub.2 CH.sub.2C(O)NHC.sub.6H.sub.5
CH.sub.2CH.dbd.CH.sub.2 CH.sub.2C(O)NH.sub.2
EXAMPLE 20
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-{[(methylsulfonyl-
)carbamoyl]-methyl}-4-oxo-3-thiazolidineacetate
[0494] 106
[0495] A solution of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinedia-
cetic acid, 3-ethyl ester (0.5 g, 0.9 mmol) and
1,1-carbonyldiimidazole (0.23 g, 1.3 mmol) in tetrahydrofuran is
refluxed for 2 hours, cooled to room temperature, treated
portionwise with a solution of ethanesulfonamide (0.22 g, 1.1 mmol)
and 1,8-diazabicyclo[5.4.0]undec-7-e- ne (0.21 g, 1.3 mmol) in
tetrahydrofuran, stirred overnight at room temperature, and poured
into dilute hydrochloric acid. The resultant aqueous mixture -s
extracted with methylene chloride. The organic extracts are
combined, washed with water, dried over anhydrous sodium sulfate,
and concentrated in vacuo to obtain a tan liquid. Column
chromatography of the liquid using silica gel and a 7.5% methanol
in methylene chloride solution gives the title product which is
identified by .sup.1H NMR spectral analyses.
[0496] Using essentially the same procedure, the following
compounds are obtained:
10 107 R R.sub.16 CH.sub.2CH.dbd.CH.sub.2 CH.sub.3 CH.sub.3
CH.sub.3 CH.sub.2CO.sub.2C.sub.2H.sub.5 C.sub.6H.sub.5
CH.sub.2CH.dbd.CH.sub.2 C.sub.6H.sub.5 CH.sub.3 C.sub.6H.sub.5
CH.sub.2CO.sub.2C.sub.2H.sub.5 C.sub.2H.sub.5
CH.sub.2CH.dbd.CH.sub.2 C.sub.2H.sub.5 CH.sub.3 C.sub.2H.sub.5
CH.sub.2CO.sub.2C.sub.2H.sub.5 CH(CH.sub.3).sub.2
CH.sub.2CH.dbd.CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3
CH(CH.sub.3).sub.2 and 108
EXAMPLE 21
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-1(2H)-pyrimi-
dinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid.
3-ethyl ester, 5-ester with ethyl lactate
[0497] 109
[0498] A mixture of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl ester (0.5 g, 0.9 mmol) and cesium carbonate
(0.28 g, 0.9 mmol) in N,N-dimethylformamide is heated to 40.degree.
C., treated with ethyl 2-bromopropionate (0.16 g, 0.9 mmol),
stirred at 40.degree. C. for 45 minutes, concentrated in vacuo, and
diluted with methylene chloride. The resultant organic solution is
washed with water, dried over anhydrous sodium sulfate, and
concentrated in vacuo to obtain a brown oil. Column chromatography
of the oil using silica gel and a methylene chloride/diethyl
ether/hexanes/acetic acid solution (33:33:33:1) gives the title
product as a clear, yellow oil which is identified by .sup.1H NMR
spectral analyses.
[0499] Using essentially the same procedure, the following
compounds are obtained:
11 110 R R.sub.37 mp .degree. C. CH.sub.2CH.dbd.CH.sub.2
CH.sub.2CO.sub.2CH(CH.sub.3- )CO.sub.2C.sub.2H.sub.5
CH.sub.2CO.sub.2CH.sub.2CH.dbd.CH.sub.2 H glass
CH.sub.2CO.sub.2CH.sub.2CO.sub.2CH.sub.3 H glass
CH.sub.2CO.sub.2CH.sub.2CN H glass CH.sub.2CO.sub.2CH(CH.sub.3).su-
b.2 H glass CH.sub.2CO.sub.2CH.sub.2C.ident.CH H glass 111 H glass
CH.sub.2CO.sub.2(CH.sub.2).sub.2OCH.sub.3 H glass
CH.sub.2CO.sub.2(CH.sub.2).sub.3CH.sub.3 H glass
CH.sub.2CO.sub.2CH(CH.sub.3)CO.sub.2CH.sub.3 H 198-200 112 H glass
CH.sub.2CO.sub.2CH.sub.2CH(CH.sub.3).sub.2 H glass 113 H glass
EXAMPLE 22
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyll-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinedi-
acetic acid, 3-ethyl methyl ester
[0500] 114
[0501] A mixture of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl ester (0.5 g, 0.9 mmol), methanol (1 mL) and a
catalytic amount of p-toluenesulfonic acid in methylene chloride is
stirred overnight at 40.degree. C., and concentrated in vacuo to
obtain a residue. Column chromatography of the residue using silica
gel and a methylene chloride/diethyl ether/hexanes/acetic acid
solution (33:33:33:1) gives the title product which is identified
by .sup.1H NMR spectral analyses.
[0502] Using essentially the same procedure, the following
compounds are obtained:
12 115 R.sub.3 R CH(CH.sub.3).sub.2 CH.sub.2CO.sub.2C.sub.2H.sub.5
CH.sub.3 CH.sub.2CH.dbd.CH.sub.2 CH.sub.2CH.dbd.CH.sub.2
CH.sub.2CH.dbd.CH.sub.2 CH(CH.sub.3).sub.2 CH.sub.2CH.dbd.CH.sub.2
CH.sub.2C.ident.CH CH.sub.2CH.dbd.CH.sub.2
EXAMPLE 23
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-{[(tritylox-
y)carbamoyl]-methyl}-3-thiazolidineacetate
[0503] 116
[0504] A mixture of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl ester (0.1 g, 0.17 mmol), 0-tritylhydroxylamine
(0.047 g, 0.17 mmol) and
(1H-benzotriazol-1-yloxy)bis-(dimethylamino)methylium
hexafluorophosphate (0.065 g, 0.17 mmol) is treated with a solution
of N,N-diisopropylethylamine (0.04 mL, 0.17 mmol) in
N,N-dimethylformamide, stirred at room temperature overnight, and
concentrated in vacuo to obtain a residue. Column chromatography of
the residue using silica gel and a 5% methanol in methylene
chloride solution gives the title product which is identified by
.sup.1H NMR spectral analysis.
[0505] Using essentially the same procedure, but substituting
methoxylamine hydrochloride for O-tritylhy-droxylamine, the
following compounds are obtained:
13 117 R CH.sub.2CO.sub.2C.sub.2H.sub.5 CH.sub.2CH.dbd.CH.sub.2
EXAMPLE 24
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(hydroxycarbamoy-
l)methyl]-4-oxo-3-thiazolidineacetate
[0506] 118
[0507] A solution of ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-methyl}-3-thiazolidineacetate
(entire sample from Example 23) and triisopropylsilane (1 mL) in
trifluoroacetic acid (19 mL) is stirred at room temperature for 4
hours, cooled with an ice-water bath, and filtered. The resultant
filtrate is concentrated in vacuo and chased three times with
toluene to obtain a solid. Column chromatography of the solid using
silica gel and a 7.5% methanol in methylene chloride solution gives
the title product as a yellow solid which is identified by .sup.1H
NMR spectral analysis.
[0508] Using essentially the same Procedure, the following
compounds are obtained:
14 119 R CH.sub.2CH.dbd.CH.sub.2 CH.sub.3
EXAMPLE 25
Preparation of 2'-Chloro-4'-fluoro-5'-nitroacetanilide
[0509] 120
[0510] A solution of 2'-chloro-4'-fluoroacetanilide (85.5 g, 456
mmol; in concentrated sulfuric acid is cooled to 0.degree. C.,
treated slowly with 70% nitric acid (32 mL, 502 mmol) while
maintaining the temperature from 5-8.degree. C., stirred at room
temperature overnight and poured into water. The resultant aqueous
mixture is filtered to obtain a solid which is recrystallized from
ethanol to give the title product as pale, yellow plates (27.0 g,
mp 158-160.degree. C.
EXAMPLE 26
Preparation of 5'-Amino-2'-chloro-4'-fluoroacetanilide
[0511] 121
[0512] A mixture of 2'-chloro-4'-fluoro-5'-nitroacetanilide (26.1
g, 112 mmol) and 5% platinum on carbon (7.8 g, 30 wt %) in a
tetrahydrofuran/ethyl acetate/ethanol solution (1:1:1) is
hydrogenated at 50 psi for 22 hours and filtered. The resultant
filtrate is concentrated in vacuo to obtain a solid which is
recrystallized from an ethanol/water solution to give the title
product as off-white plates (14.5 g, mp 176-178.degree. C.)
EXAMPLE 27
Preparation of
2'-Chloro-5'-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2-
H)-pyrimidinyl]-4'-fluoroacetanilide
[0513] 122
[0514] A mixture of 5'-amino-2'-chloro-4'-fluoroacetanilide (1.0 g,
4.9 mmol) and
2-diemethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (1.0 g,
4.9 mmol) in acetic acid is refluxed for 90 minutes and dilutedwith
water. The resultant aquaous mixturee is filtered to obtain the
title product as an off-white solid (1.4 g, mp 264-266.degree. C.)
which is identified by .sup.1H, .sup.13C and .sup.19F NMR spectral
analyses.
EXAMPLE 28
Preparation of
2'-Chloro-5'-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome-
thyl)-1(2H)-pyrimidinyl]-4'-fluoroacetanilide
[0515] 123
[0516] A mixture of
2'-chloro-5'-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl-
)-1(2H)-pyrimidinyl]-4'-fluoroacetanilide (0.85 g, 2.3 mmol),
potassium carbonate (0.32 g, 2.3 mmol) and dimethylsulfate (0.22
mL, 2.3 mmol) in tetrahydrofuran is refluxed for 90 minutes, cooled
to room temperature, and diluted with water and chloroform. The
resultant mixture is concentrated in vacuo to obtain an aqueous
suspension which is filtered to give the title product as an
off-white solid (0.75 g, mp 257-258.5.degree. C.).
EXAMPLE 29
Preparation of
3-(5-Amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluorome-
thyl)-2,4(1H,3H)-pyrimidinedione
[0517] 124
[0518] A mixture of
2'-chloro-5'-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4'-fluoro-acetanilide (24.42 g, 64.3
mmol) in ethanol is treated with 2N hydrochloric acid (200 ml),
diluted with tetrahydrofuran, refluxed overnight, cooled to room
temperature, partially concentrated in vacuo to remove ethanol and
tetrahydrofuran, neutralized with 3N sodium hyaroxide solution, an
a extracted with ethyl acetate. The organic extracts are combined,
washed sequentially with saturated sodium hydrogen carbonate
solution and brine, dried over anhydrous magnesium sulfate, and
concentrated in vacuo to give the title product as a light, brown
solid (20.3 g, mp 132-135.degree. C.).
EXAMPLE 30
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-isopropylidene-4--
oxo-3-thiazol-idineacetate
[0519] 125
[0520] A mixture of ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetate (2.0 g, 3.83 mmol), acetone (0.562 mL, 7.65 mmol),
piperidine (0.20 mL, 2.02 mmol) and acetic acid (20 .mu.L) in
ethanol is refluxed for 90 minutes, treated with additional acetone
(0.562 mL) , refluxed for 3.5 hours, stirred at room temperature
overnight, concentrated in vacuo, and chased with ethyl acetate to
obtain a residue. Column chromatography of the residue using silica
gel and an ethyl acetate/hexanes solution (1:3) gives the title
product as a white solid (1.5 g, mp 67-80.degree. C.).
[0521] Using essentially the same procedure, the following
compounds are obtained:
15 126 R.sub.41 R.sub.42 mp .degree. C.
--CH.sub.2CH.sub.2CH.sub.2CH.sub.2-- 84-92 127 H 189-191 128 H
207-210 129 H 130 H 131 H 132 H 133 H
EXAMPLE 31
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(o-hydroxvbenzvl)-4-ox-
o-3-thiazolidine-acetic acid, ethyl ester, ester with ethyl
glycolate
[0522] 134
[0523] A mixture of
5-[o-(carboxymethoxy)benzylidene]-2-{{2-chloro-5-[3,6--
dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-
phenyl}imino}-4-oxo-3-thiazolidineacetic acid, diethyl ester (2.1
g, 2.95 mmol) and 10% palladium on carbon (2.0 g) in ethyl acetate
is hydrogenated at 50 psi for 72 hours at room temperature, and
filtered to remove solids. The resultant filtrate is concentrated
in vacuo to give a residue. Column chromatography of the residue
using silica gel and an ethyl acetate/hexanes solution (1:2) gives
the title product as a white solid (0.79 g, mp 47-60.degree. C.)
which is identified by .sup.1H NMR spectral analysis.
[0524] Using essentially the same procedure, the following
compounds are obtained:
16 135 J mp .degree. C. 136 68-73 OCH.sub.2CO.sub.2C(CH.sub.3).-
sub.3 137 H 70-72 OCH.sub.3 66-76
EXAMPLE 32
Preparation of
5-[o-(Carboxvmethoxy)benzyl]-2-{{2-chloro-5-[3,6-dihvdro-3--
methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imi-
no}-4-oxo-3-thiazolidineacetic acid, 3-ethyl ester
[0525] 138
[0526] A solution of
5-[o-(carboxymethoxy)benzyl]-2-{{2-chloro-5-[3,6-dihy-
dro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophen-
yl}imino}-4-oxo-3-thiazolidineacetic acid, 5-tert-butyl ethyl ester
(2.2 g, 2.96 mmol) in methylene chloride is treated with
trifluoroacetic acid (5.5 mL, 71.4 mmol), stirred at room
temperature for 7.5 hours, concentrated in vacuo, and chased with
toluene and hexanes to obtain a residue. The residue is disolved in
diethyl ether, diluted with hexanes, held overnight at 0.degree.
C., and filtered to give the title product as a white solid (2.0 g,
mp 93-98.degree. C.).
[0527] Using essentially the same procedure, the following compound
is obtained: 139
EXAMPLE 33
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineaceti-
c acid, ethyl ester, 1-oxide
[0528] 140
[0529] A solution of ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
olidineacetate (3.00 g, 5.74 mmol) in methylene chloride is treated
with 3-chloroperoxybenzoic acid (1.23 g, 57%-86% real), stirred at
room temperature for 3 hours, and poured into saturated sodium
hydrogen carbonate solution. After separating the phases, the
organic phase is washed with saturated sodium hydrogen carbonate
solution, dried over anhydrous magnesium sulfate, and concentrated
in vacuo to obtain a residue. Column chromatography of the residue
using silica gel and an ethyl acetate/hexanes solution (2:3) gives
the title product as a yellow solid (1.0 g, mp 105-115.degree. C.)
which is identified by .sup.1H and .sup.13C NMR spectral
analyses.
[0530] Following essentially the same procedure, but using at least
2 equivalents of 3-chloroperoxybenzoic acid,
2-{{2-chloro-5-[3,6-dihydro-3--
methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imi-
no}-4-oxo-3-thiazolidineacetic acid, ethyl ester, 1,1-dioxide is
obtained as a white solid (mp 75-88.degree. C.)
EXAMPLE 34
Preparation of Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyll-4-fluorophenyl}imino}-5-(hydroxyethyl)-4--
oxo-3-thiazolidineacetate
[0531] 141
[0532] A mixture of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediac-
etic acid, 3-ethyl ester (2.0 g, 3.44 mmol) and borane-methyl
sulfide complex (0.36 g, 3.8 mmol) in tetrahydrofuran is stirred at
40-45.degree. C. for 2 days with additional borane-methyl sulfide
complex (2.times.0.36 g) being added at equal intervals. The
reaction mixture is then cooled to room temperature, treated with
methanol (5 mL), stirred overnight at room temperature, and
concentrated in vacuo to obtain a glass. Column chromatography of
the glass using silica gel and 2% to 10% ethyl acetate in methylene
chloride solutions gives the title product (0.46 g, mp
137-139.degree. C.)
EXAMPLE 35
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-oxazolidinedia-
cetic acid, 3-ethyl ester
[0533] 142
[0534] A solution of
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,
5-oxazolidinediacetic acid, 5-benzyl ethyl ester (0.65 g, 1.0 mmol)
in methylene chloride is cooled to 0.degree. C., treated with boron
trichloride (1 mL of a 1M solution in methylene chloride), stirred
at 0.degree. C. for 30 minutes, treated with additional boron
trichloride (1 mL of a 1M solution in methylene chloride) , stirred
at room temperature for 90 minutes, and poured into an ice-water
mixture. The resultant aqueous mixture is extracted with methylene
chloride. The organic extracts are combined, washed with brine,
dried over anhydrous magnesium sulfate, and concentrated in vacuo
to give the title product (0.2 g) which is identified by .sup.1H
and .sup.13C NMR spectral analyses.
EXAMPLE 36
Preparation of
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineaceti-
c acid
[0535] 143
[0536] A solution of tert-butyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-d-
ioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3--
thiazolidineacetate (41.93 g, 76.1 mmol) in trifluoroacetic acid is
stirred at room temperature for 3 hours, stirred at 35.degree. C.
for 1 hour, and concentrated in vacuo to obtain a yellow liquid. A
solution of the yellow liquid in diethyl ether is cooled and
filtered to obtain a solid. The solid is washed with diethyl ether
and air-dried to give the title product as a white solid (31.6 g)
which is identified by .sup.1H and .sup.13C NMR spectral
analyses.
EXAMPLE 37
Postemergence Herbicidal Evaluation of Test Compounds
[0537] The postemergence herbicidal activity of the compounds of
the present invention is demonstrated by the following tests
wherein a variety of dicotyledonous and monocotyledonous plants are
treated with test compounds. In the tests, seedling plants are
grown in jiffy flats for about two weeks. The test compounds are
dispersed in 50/50 acetone/water mixtures containing 0.5%
TWEEN.RTM.20, a polyoxyethylene sorbitan monolaurate surfactant of
Atlas Chemical Industries, in sufficient quantities to provide the
equivalent of about 0.0156 kg to 0.500 kg per hectare of active
compound when applied to the plants through a spray nozzle
operating at 40 psi for a predetermined time. After spraying, the
plants are placed on greenhouse benches and are cared for in
accordance with conventional greenhouse procedures. From four to
five weeks after treatment, the seedling plants are examined and
rated according to the rating system set forth below. Data obtained
are reported in Table I below. Where more than one test is involved
for a given compound, the data are averaged.
[0538] Plant species employed in these evaluations are reported by
header abbreviation, common name and scientific name.
[0539] Compounds employed in this postemergence herbicidal
evaluation are given a compound number and identified by name. Data
in Table I are reported by compound number.
[0540] Herbicide Rating Scale
[0541] Results of herbicide evaluation are expressed on a rating
scale (0-9). The scale is based upon a visual observation of plant
stand, vigor, malformation, size, chlorosis and overall plant
appearance as compared with a control.
17 % Control Rating Meaning Compared to Check 9 Complete kill 100 8
Approaching Complete Kill 91-99 7 Good Herbicidal Effect 80-90 6
Herbicidal Effect 65-79 5 Definite Injury 45-64 4 Injury 30-44 3
Moderate Effect 16-29 2 Slight Effect 6-15 1 Trace Effect 1-5 0 No
Effect 0 A blank space indicates that no evaluation was
conducted.
[0542] Plant Species Employed in Herbicidal Evaluations
18 Header Abbr. Common Name Scientific Name ABUTH Velvetleaf
Abutilon theophrasti, Medic. AMBEL Ragweed, Common Ambrosia
artemisifolia, L. CASOB Sicklepod Cassia obtusifolia, L. CHEAL
Lambsquarters, Common Chenopodium album, L. GALAP Galium Galium
aparine IPOHE Morningglory, Ivyleaf Ipomoea hederacea, (L.) Jacq.
IPOSS Morningglory Spp. Ipomoea Spp. ECHCG Barnyardgrass
Echinochloa crus-galli, (L.) Beau SETVI Foxtail, Green Setaria
viridis, (L.) Beau GLXMAW Soybean, Williams Glycine max, (L.) Merr.
cv Williams GLXMA Soybean Glycine max, (L.) Merr. ORYSAT Rice,
Tebonnet Oryza sativa, (L.) Tebonnet TRZAWR Wheat, Winter, Triticum
aestivum, cv Riband cv Riband ZEAMX Corn, Field Zea mays, L.
COMPOUNDS EVALUATED AS HERBICIDAL AGENTS
[0543] Compound
[0544] Number
[0545] 1.
N-{4-chloro-2-fluoro-5-[(3-methyl-4-oxo-2-thiazolidinylidene)ami-
no]phenyl}-1-cyclohexene-1,2-dicarboximide
[0546] 2.
N-{5-[(3-allyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluo-
rophenyl}-1-cyclohexene-1,2-dicarboximide
[0547] 3.
N-{4-chloro-2-fluoro-5-[(4-oxo-3-phenyl-2-thiazolidinylidene)ami-
no]phenyl}-1-cyclohexene-1,2-dicarboximide
[0548] 4.
N-{4-chloro-2-fluoro-5-(3,5-dimethyl-4-oxo-2-thiazolidinylidene)-
amino]phenyl}-1-cyclohexene-1,2-dicarboximide
[0549] 5.
N-{4-chloro-2-fluoro-5-[(5-fluoro-3-methyl-4-oxo-2-thiazolidinyl-
idene)amino]phenyl}-1-cyclohexene-1,2-dicarboximide
[0550] 6.
N-{4-chloro-5-[(5-ethyl-3-methyl-4-oxo-2-thiazolidinylidene)amin-
o]-2-fluorophenyl}-1-cyclohexene-1,2-dicarboximide
[0551] 7.
3-{4-Chloro-2-fluoro-5-[3-methyl-4-oxo-2-thiazolidinylidene)amin-
o]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0552] 8. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor-
omethyl)-1(2H)pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineaceta-
te
[0553] 9.
3-{4-Chloro-5-[(3,5-dimethyl-4-oxo-2-thiazolidinyl-idene)amino]--
2-fluorophenyl}-1-methyl-6-trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0554] 10.
3-{4-Chloro-5-[(5-ethyl-3-methyl-4-oxo-2-thiazolidinylidene)ami-
no]-2-fluorophenyl}-1-methyl-6-trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0555] 11. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-fluoro-4-oxo-3-thiazo-
lidineacetate
[0556] 12. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino-5-methyl -4-oxo
-3-thiazolidineacetate
[0557] 13. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-ethyl
-4-oxo-3-thiazolidineacetate
[0558] 14.
3-(Carboxymethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H
)-pyrimidinyl-4-fluorophenylimino}-4-oxo-delta5-
,alpha-thiazolidineacetic acid, diethyl ester
[0559] 15. Ethyl
5-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-7-oxo-4-thia-6-azaspiro-
[2.4]-heptane-6-acetate
[0560] 16.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester
[0561] 17. Methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineac-
etate
[0562] 18. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-cyclopentylidene-4-ox-
o-3-thiazolidineacetate
[0563] 19. Ethyl
5-benzylidene-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-t-
hiazolidineacetate
[0564] 20. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-isopropylidene-4-oxo--
3-thiazolidineacetate
[0565] 21. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(p-fluorobenzylidene)-
-4-oxo-3-thiazolidineacetate
[0566] 22. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-oxazolidineacet-
ate
[0567] 23.
3-{4-Chloro-5-{[3-(dimethylamino)-4-oxo-2-thiazolidinylidine]am-
ino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedio-
ne
[0568] 24. Ethyl
5-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetate
[0569] 25. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-5-oxo-1-imidaz-
olidineacetate
[0570] 26.
3-(5-[(3-Benzyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fl-
uorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione3-{
[0571] 27.
5-[(3-Allyl-4-oxo-2-thiazolidinylidene)amino]-4-chloro-2-fluoro-
phenyl}-1-methyl-6-(trifluoro-methyl)-2,4(1H,3H)-pyrimidinedione
[0572] 28. Methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepr-
opionate
[0573] 29. Methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinebu-
tyrate
[0574] 30.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinepropionic
acid
[0575] 31.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidinepropioni-
c acid
[0576] 32. Ethyl
2-{{2,4-dichloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-phenyl}imino}-4-oxo-3-thiazolidinepropion-
ate
[0577] 33.
2-{{2,4-Dichloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro-
methyl)-1(2H)-pyrimidinyl]phenyl}-imino}-4-oxo-3,5-thiazolidinediacetic
acid, 3-ethyl ester
[0578] 34.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-1,3-imidazolidinediace-
tic acid, diethyl ester
[0579] 35. Diethyl
{{2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidin-
yl}methyl}phosphonate
[0580] 36. Ethyl
2-{{2-chloro-5-[4-(difluoromethyl-4,5-dihydro-3-methyl-5--
oxo-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}imino}-3-thiazolidineacetate
[0581] 37. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(o-methoxybenzyl)-4-o-
xo-3-thiazolidineacetate
[0582] 38.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-N-(methylsulfonyl)-4-oxo-3-t-
hiazolidineacetamide
[0583] 39.
3-{4-Chloro-2-fluoro-5-[(4-oxo-2-thiazolidinylidene)amino]pheny-
l}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0584] 40.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-oxazolidinediacetic
acid, 5-benzyl ethyl ester
[0585] 41.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-oxazolidinediaceti-
c acid, 3-ethyl ester
[0586] 42.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(o-hydroxybenzyl)-4-oxo-3--
thiazolidineacetic acid, ethyl ester, ester with ethyl
glycolate
[0587] 43. tert-Butyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetate
[0588] 44.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetanilide
[0589] 45.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetic
acid, ethyl ester, 1-oxide
[0590] 46.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetic
acid, ethyl ester, 1,1-dioxide
[0591] 47. Ethyl
2-{[2-chloro-5-(1-cyclohexene-1,2-dicarboximido)-4-fluoro-
phenyl]imino}-4-oxo-3-thiazolidineacetate
[0592] 48.
2-{[2-Chloro-5-(1-cyclohexene-1,2-dicarboximido)-4-fluorophenyl-
]imino}-4-oxo-3,5-thiazolidinediacetic acid
[0593] 49. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(hydroxyethyl)-4-oxo--
3-thiazolidineacetate
[0594] 50.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-5-(o-hydroxybenzyl)-4-oxo-3--
thiazolidineacetic acid, ethyl ester, ester with methyl lactate
[0595] 51.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-.alpha.-methyl-4-oxo-3-thiaz-
olidineacetic acid, L-
[0596] 52.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3-thiazolidineacetic
acid
[0597] 53.
.alpha.-Benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetic acid, L-
[0598] 54.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,
5-thiazolidinediacetic acid, 3-ethyl methyl ester
[0599] 55.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacet-
ic acid, 3-ethyl isopropyl ester
[0600] 56. Ethyl
5-(carbamoylmethyl)-2-{{2-chloro-5-[3,6-dihydro-3-methyl--
2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-o-
xo-3-thiazolidineacetate
[0601] 57. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methylcarbamoyl)met-
hyl]-4-oxo-3-thiazolidineacetate
[0602] 58.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidenediacet-
ic acid, 3-ethyl (2-propynyl) ester, (2:1) mixture with
di-2-propynyl ester
[0603] 59.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediaceti-
c acid, 3-ethyl (2-propynyl) ester
[0604] 60.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacet-
ic acid, 3-ethyl isopropyl ester
[0605] 61.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediaceti-
c acid
[0606] 62.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetic acid
[0607] 63.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-3-methyl-4-oxo-5-thiazolidin-
eacetic acid
[0608] 64. Methyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazo-
lidineacetate
[0609] 65. Allyl
3-allyl-2-{(2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazol-
idineacetate
[0610] 66. Isopropyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thi-
azolidineacetate
[0611] 67. 2-Propynyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-th-
iazolidineacetate
[0612] 68. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-[(phenylcarbamo-
yl)-methyl]-3-thiazolidineacetate
[0613] 69.
.alpha.-Benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetic acid, D-
[0614] 70.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-.alpha.-methyl-4-oxo-3-thiaz-
olidineacetic acid, D-
[0615] 71.
.alpha.-Isobutyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-
-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thia-
zolidineacetic acid, L-
[0616] 72. Methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]imino}-4-oxo-3-
-thiazolidineacetate, L-
[0617] 73.
3-{4-Chloro-2-fluoro-5-{[4-oxo-3-(tetrahydro-2-oxo-3-furyl)-2-t-
hiazolidinylidene]amino}phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyr-
imidinedione
[0618] 74. Methyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-
-thiazolidineacetate, D-
[0619] 75. tert-Butyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-.alpha.-methyl-4-o-
xo-3-thiazolidineacetate, L-
[0620] 76. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-.alpha.-methyl-4-oxo-3--
thiazolidineacetate, L-
[0621] 77. Methyl
.alpha.-(p-chlorobenzyl)-2-{{2-chloro-5-[3,6-dihydro-3-m-
ethyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imin-
o}-4-oxo-3-thiazolidineacetate, DL-
[0622] 78. Methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-.alpha.-(p-nitro-
benzyl)-3-thiazolidineacetate, L-
[0623] 79. Ethyl
.alpha.-(p-chlorophenyl)-2-{{2-chloro-5-[3,6-dihydro-3-me-
thyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino-
}-4-oxo-3-thiazolidineacetate, DL-
[0624] 80. Ethyl
.alpha.-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-d-
ioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3--
thiazolidineacetate, L-
[0625] 81. Methyl
1-{2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidin-
yl}-cyclohexanecarboxylate
[0626] 82.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}imino}-4-oxo-3,5-thiazolidinediacet-
ic acid, 3-ethyl 2-fluoroethyl ester
[0627] 83. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(methoxycarbamoyl)me-
thyl]-4-oxo-3-thiazolidineacetate
[0628] 84.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-N-methyl-4-oxo-5-thia-
zolidineacetamide
[0629] 85.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}iminol-N-methoxy-4-oxo-5-thi-
azolidineacetamide
[0630] 86. 2-Fluoroethyl
3-allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6--
dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-
-thiazolidineacetate
[0631] 87.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-1(2H)-pyrimidiny-
l]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid,
3-ethyl ester, 5-ester with ethyl lactate
[0632] 88. Methyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-thiaz-
olidineacetate
[0633] 89. Isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-th-
iazolidineacetate
[0634] 90. 2-Propynyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-t-
hiazolidineacetate
[0635] 91.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-thiazolidine-
acetanilide
[0636] 92.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-thiazolidine-
acetamide
[0637] 93. 2-Fluoroethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4--
(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo--
5-thiazolidineacetate
[0638] 94.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-1(2H)-py-
rimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidineacetic acid,
ester with ethyl lactate, (R,S)-
[0639] 95. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-{[(methylsulfonyl)car-
bamoyl]-methyl}-4-oxo-3-thiazolidineacetate
[0640] 96.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pryimidinyl]-4-fluorophenyl}imino}-N-(methylsulfonyl)-4--
oxo-5-thiazolidineacetamide
[0641] 97.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorometh-
yl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-N-(methylsulfonyl)-4-
-oxo-5-thiazolidineacetamide
[0642] 98. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo-
romethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-[(hydroxycarbamoyl)me-
thyl]-4-oxo-3-thiazolidineacetate
[0643] 99.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidinea-
cetamide
[0644] 100. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-{[(phenylsulfo-
nyl)-carbamoyl]methyl]-3-thiazolidineacetate
[0645] 101.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-N-(phenylsulfo-
nyl)-5-thiazolidineacetamide
[0646] 102.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-N-(phenylsulf-
onyl)-5-thiazolidineacetamide
[0647] 103. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-{[(ethylsulfonyl)car-
bamoyl]-methyl}-4-oxo-3-thiazolidineacetate
[0648] 104.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-N-(ethylsulfonyl)-4--
oxo-5-thiazolidineacetamide
[0649] 105.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-N-(ethylsulfonyl)-3-methyl-4-
-oxo-5-thiazolidineacetamide
[0650] 106. Allyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineac-
etate
[0651] 107. 2-Methoxyethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
olidineacetate
[0652] 108.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetic
acid, ester with methyl glycolate
[0653] 109.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetic
acid, ester with glycolonitrile
[0654] 110. Isopropyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino.ident.-4-oxo-3-thia-
zolidineacetate
[0655] 111. Butyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu- oromethyl
)-1(2H)-pyrimidinyl]-4-fluorophenyl imino}-4-oxo-3-thiazolidinea-
cetate
[0656] 112.
2-{{2-Chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo--
1H-1,2,4-triazol-1-yl]-4-fluorophenyl}imino}-4-oxo-3,5-thiazolidinediaceti-
c acid, 3-ethyl ester
[0657] 113.
5-[o-(Carboxymethoxy)benzyl]-2-{{2-chloro-5-[3,6-dihydro-3-met-
hyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-
-4-oxo-3-thiazolidineacetic acid, 3-ethyl ester
[0658] 114.
5-[o-(1-Carboxyethoxy)benzyl]-2-{{2-chloro-5-[3,6-dihydro-3-me-
thyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino-
}-4-oxo-3-thiazolidineacetic acid, 3-ethyl ester
[0659] 115. 2-Propynyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(t-
rifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolid-
ineacetate
[0660] 116.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetic
acid, ester with methyl lactate
[0661] 117. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-{[(isopropylsulfonyl-
)-carbamoyl]methyl}-4-oxo-3-thiazolidineacetate
[0662] 118.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-N-(isopropylsulfonyl-
)-4-oxo-5-thiazolidineacetamide
[0663] 119.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-N-(isopropylsulfonyl)-3-meth-
yl-4-oxo-5-thiazolidineacetamide
[0664] 120. Cyclopentyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(-
trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-
dineacetate
[0665] 121. Isobutyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tri-
fluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidin-
eacetate
[0666] 122.
3-{4-Chloro-2-fluoro-5-[(3-furfuryl-4-oxo-2-thiazolidinylidene-
)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0667] 123. Cyclohexylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-diox-
o-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thi-
azolidineacetate
[0668] 124. Cyclopropylmethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dio-
xo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-th-
iazolidineacetate
[0669] 125. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(methylthio)-4-oxo-3-
-thiazolidineacetate
[0670] 126. Ethyl
5-chloro-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo--
4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiaz-
olidineacetate
[0671] 127.
5-Carboxy-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetic acid, diethyl ester
[0672] 128.
5-Carboxy-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetic acid, 3-ethyl methyl ester
[0673] 129.
3-{4-Chloro-2-fluoro-5-{[3-(o-methylbenzyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4
(1H,3H)-pyrimidinedione
[0674] 130.
3-{4-Chloro-2-fluoro-5-{[3-(m-methylbenzyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4 (1H,
3H)-pyrimidinedione
[0675] 131.
3-{4-Chloro-2-fluoro-5-{[4-oxo-3-(2-pyridylmethyl)-2-thiazolid-
inylidene]aminophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0676] 132.
3-{4-Chloro-2-fluoro-5-{[4-oxo-3-(3-pyridylmethyl)-2-thiazolid-
inylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4
(1H,3H)-pyrimidinedione
[0677] 133.
3-{4-Chloro-2-fluoro-5-{[4-oxo-3-(4-pyridylmethyl)-2-thiazolid-
inylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidine-
dione
[0678] 134.
3-{4-Chloro-5-{[3-(3,4-dimethoxybenzyl)-4-oxo-2-thiazolidinyli-
dene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimi-
dinedione
[0679] 135.
Alpha-{2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifl-
uoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidinyl-
}-p-toluenesulfonamide
[0680] 136.
3-{4-Chloro-5-{[3-(m-chlorobenzyl)-4-oxo-2-thiazolidinylidene]-
amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0681] 137.
3-{4-Chloro-2-fluoro-5-{[3-(m-methoxybenzyl)-4-oxo-2-thiazolid-
inylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidine-
dione
[0682] 138.
3-{4-Chloro-5-{{3-[p-(dimethylamino)benzyl]-4-oxo-2-thiazolidi-
nylidene}amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-py-
rimidinedione
[0683] 139.
3-{4-Chloro-5-{[3-(2,4-dimethoxybenzyl)-4-oxo-2-thiazolidinyli-
dene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimi-
dinedione
[0684] 140.
3-{4-Chloro-2-fluoro-5-{[3-(3,4,5-trimethoxybenzyl)-4-oxo-2-th-
iazolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyr-
imidinedione
[0685] 141.
3-{4-Chloro-2-fluoro-5-{{3-[p-(trifluoromethyl)benzyl]-4-oxo-2-
-thiazolidinylidene}-amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4
(1H, 3H)-pyrimidinedione
[0686] 142.
3-{4-Chloro-2-fluoro-5-{{3-[m-(trifluoromethyl)benzyl]-4-oxo-2-
-thiazolidinylidene}-amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-
-pyrimidinedione
[0687] 143.
3-{4-Chloro-5-t[3-(o-chlorobenzyl)-4-oxo-2-thiazolidinylidene]-
amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0688] 144.
3-{4-Chloro-5-{[3-(3,4-dichlorobenzyl)-4-oxo-2-thiazolidinylid-
ene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione
[0689] 145.
3-{4-Chloro-5-{[3-(p-chlorobenzyl)-4-oxo-2-thiazolidinylidene]-
amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0690] 146.
3-{4-Chloro-5-{[3-(3,5-dimethylbenzyl)-4-oxo-2-thiazolidinylid-
ene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione
[0691] 147.
3-{4-Chloro-5-{[3-(3,4-dimethylbenzyl)-4-oxo-2-thiazolidinylid-
ene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione
[0692] 148.
3-{5-{[3-(p-Bromobenzyl)-4-oxo-2-thiazolidinyl-idene]amino}-4--
chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0693] 149.
3-{4-Chloro-5-{[3-(3-chloro-4-methylbenzyl)-4-oxo-2-thiazolidi-
nylidene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-py-
rimidinedione
[0694] 150.
3-{4-Chloro-5-{[3-(3,5-dichlorobenzyl)-4-oxo-2-thiazolidinylid-
ene]amino}-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione
[0695] 151.
3-{4-Chloro-2-fluoro-5-{[3-(p-fluorobenzyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0696] 152.
3-{4-Chloro-5-[(3-cyclopropyl-4-oxo-2-thiazolidinylidene)amino-
]-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0697] 153. Ethyl
5-bromo-2-[{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazo-
lidineacetate
[0698] 154. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl3imino}-5-methylene-4-oxo-3-th-
iazolidineacetate
[0699] 155.
3-{4-Chloro-2-fluoro-5-{[3-(2-methoxyethyl)-4-oxo-2-thiazolidi-
nylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidined-
ione
[0700] 156. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-(methoxymethyl)-4-ox-
o-3-thiazolidine-acetate
[0701] 157.
3-{4-Chloro-2-fluoro-5-{{3-[2-(methylthio)ethyl]-4-oxo-2-thiaz-
olidinylidene}amino}phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimid-
inedione
[0702] 158. Methyl
{{2-{2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(-
trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazoli-
dinyl}ethyl}-thio}acetate
[0703] 159.
3-{4-Chloro-5-[(3-ethyl-4-oxo-2-thiazolidinyl-idene)amino]-2-f-
luorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0704] 160. Ethyl
2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(triflu-
oromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-5-methoxy-4-oxo-3-thia-
zolidineacetate
[0705] 161.
3-Allyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trif-
luoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-thiazolidine-
acetohydroxamic acid
[0706] 162.
2-{{2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromet-
hyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-3-methyl-4-oxo-5-thiazolidin-
eacetohydroxamic acid
[0707] 163.
3-{4-Chloro-2-fluoro-5-{[4-oxo-3-(2,2,2-trifluoroethyl)-2-thia-
zolidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrim-
idinedione
[0708] 164.
3-{4-Chloro-2-fluoro-5-[(3-isopropyl-4-oxo-2-thiazolidinyliden-
e)amino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0709] 165.
3-{4-Chloro-2-fluoro-5-{[3-(1-methyl-2-propynyl)-4-oxo-2-thiaz-
olidinylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimi-
dinedione
[0710] 166.
3-{4-Chloro-5-[(3-cyclopentyl-4-oxo-2-thiazolidinylidene)amino-
]-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0711] 167.
5-Carboxy-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(tr-
ifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidi-
neacetic acid, 5-tert-butyl ethyl ester
[0712] 168.
3-{4-Chloro-5-[(3-cyclobutyl-4-oxo-2-thiazolidinylidene)amino]-
-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
[0713] 169. Ethyl
2-{{2-chloro-5-[2,6-dioxo-4-(trifluoromethyl)piperidino]-
-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate
[0714] 170.
2-{{2-Chloro-5-[2,6-dioxo-4-(trifluoromethyl)-piperidino]-4-fl-
uorophenyl}imino}-4-oxo-3,5-thiazolidinediacetic acid, 3-ethyl
ester
[0715] 171.
3-{4-Chloro-2-fluoro-5-[(4-oxo-3-propyl-2-thiazolidinylidene)a-
mino]phenyl}-1-methyl-6-(trifluoromethyl)-2,4 (1H,
3H)-pyrimidinedione
[0716] 172.
3-{4-Chloro-2-fluoro-5-{[3-(3-methoxypropyl)-4-oxo-2-thiazolid-
inylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,
3H)-pyrimidinedione
[0717] 173.
3-{4-Chloro-2-fluoro-5-{[3-(2-fluoroethyl)-4-oxo-2-thiazolidin-
ylidene]amino}phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,
3H)-pyrimidinedione
19TABLE I Postemergence Herbicidal Evaluations of Test Compounds
Compound Rate Number (kg/ha) ABUTH AMBEL CASOB CHEAL GALAP IPOHE
IPOSS ECHCG SETVI GLXMAW GLXMA ORYSAT TRZAWR ZEAMX 1 0.5000 9.0 8.0
7.0 9.0 9.0 9.0 7.0 9.0 6.0 5.5 6.0 6.5 0.2500 9.0 7.0 6.0 9.0 9.0
9.0 5.0 7.0 5.5 5.5 5.5 5.5 0.1250 9.0 5.0 4.0 9.0 8.0 9.0 2.0 7.0
5.0 3.5 5.0 5.0 0.0625 8.0 3.0 4.0 7.0 6.0 9.0 2.0 4.0 4.5 3.0 4.0
4.0 0.0313 8.0 3.0 2.0 7.0 6.0 9.0 0.0 3.0 4.5 1.5 3.5 3.5 0.0157
5.0 2.0 0.0 6.0 4.0 6.0 0.0 1.0 4.0 1.0 2.5 2.5 2 0.5000 9.0 9.0
7.0 9.0 4.0 9.0 0.0 0.0 3.0 3.0 3.0 4.0 0.2500 9.0 6.0 4.0 7.0 4.0
9.0 0.0 0.0 3.0 3.5 2.5 3.5 0.1250 9.0 2.0 2.0 9.0 4.0 6.0 0.0 0.0
3.0 3.5 2.5 3.5 0.0625 9.0 6.0 2.0 8.0 4.0 4.0 0.0 3.5 3.0 3.0 3.0
0.0313 4.0 2.0 4.0 6.0 8.0 4.0 0.0 0.0 3.5 3.0 2.5 3.0 0.0157 0.0
4.0 4.0 7.0 4.0 4.0 0.0 0.0 3.5 3.0 1.5 3.0 3 0.5000 9.0 9.0 4.0
9.0 9.0 9.0 0.0 0.0 4.5 3.5 4.0 3.5 0.2500 6.0 6.0 6.0 9.0 6.0 8.0
0.0 0.0 4.0 2.0 3.0 3.5 0.1250 9.0 6.0 0.0 9.0 4.0 9.0 0.0 0.0 4.0
3.0 2.5 3.0 0.0625 6.0 0.0 0.0 6.0 4.0 4.0 0.0 0.0 3.0 3.0 3.0 3.0
0.0313 6.0 2.0 0.0 7.0 2.0 2.0 0.0 0.0 3.5 2.5 2.5 3.0 0.0157 6.0
0.0 9.0 0.0 0.0 2.5 2.0 2.5 3.0 4 0.5000 9.0 6.0 2.0 4.0 6.0 4.0
2.0 8.0 4.5 3.0 4.5 4.0 0.2500 9.0 6.0 0.0 4.0 1.0 4.0 2.0 4.5 1.5
4.5 4.0 0.1250 9.0 2.0 0.0 8.0 2.0 0.0 0.0 0.0 4.5 2.5 4.0 4.0
0.0625 4.0 0.0 0.0 6.0 2.0 0.0 0.0 2.0 2.5 1.0 3.5 3.5 0.0313 2.0
0.0 0.0 2.0 0.0 0.0 0.0 0.0 2.0 1.0 3.0 3.0 5 0.5000 9.0 9.0 9.0
9.0 9.0 9.0 2.0 4.0 4.5 2.5 4.5 3.5 0.2500 9.0 2.0 0.0 8.0 9.0 9.0
4.0 8.0 4.0 2.5 5.0 4.0 0.1250 9.0 0.0 0.0 9.0 9.0 4.0 3.0 4.0 4.0
2.5 4.5 3.5 0.0625 9.0 0.0 0.0 6.0 8.0 2.0 0.0 2.0 3.0 2.5 3.5 4.0
0.0313 2.0 0.0 0.0 2.0 2.0 1.0 0.0 0.0 3.0 1.5 3.0 3.5 0.0157 1.0
0.0 0.0 2.0 0.0 0.0 0.0 0.0 3.0 1.5 3.0 3.5 6 0.5000 9.0 4.0 6.0
9.0 9.0 9.0 2.0 2.0 4.0 2.5 3.5 4.0 0.2500 9.0 4.0 2.0 6.0 7.0 4.0
1.0 2.0 4.0 2.5 3.5 3.5 0.1250 9.0 4.0 0.0 2.0 2.0 0.0 2.0 3.5 2.5
3.0 3.5 0.0625 8.0 2.0 0.0 2.0 0.0 0.0 0.0 0.0 3.0 2.5 3.0 3.5
0.0313 8.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 2.5 2.5 3.5 0.0157 7.0
2.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 2.5 2.5 3.0 7 0.1250 9.0 9.0 7.0
9.0 9.0 4.0 9.0 7.5 6.5 6.0 7.0 0.0625 9.0 7.0 5.0 6.0 5.0 9.0 3.0
9.0 7.5 4.5 5.0 7.0 0.0313 9.0 5.0 5.0 5.0 4.0 7.0 0.0 4.0 6.5 4.0
3.0 6.0 0.0157 9.0 5.0 4.0 0.0 3.0 6.0 2.0 5.0 5.0 4.5 4.5 5.0 8
0.1250 9.0 8.6 3.0 9.0 6.8 9.0 8.2 9.0 8.4 5.3 6.4 7.6 0.0625 9.0
8.3 3.0 8.4 6.3 9.0 5.3 7.6 7.9 4.1 6.4 7.4 0.0313 9.0 7.8 1.8 7.5
4.5 9.0 2.1 5.3 7.6 2.7 5.1 7.3 0.0157 9.0 9.0 0.0 5.0 3.0 9.0 3.0
7.5 2.0 3.5 7.5 9 0.1250 9.0 7.0 4.5 9.0 7.5 9.0 4.5 9.0 7.3 3.5
5.0 7.0 0.0625 9.0 7.5 2.0 9.0 4.5 9.0 2.0 6.5 6.8 3.0 4.3 5.5
0.0313 9.0 3.5 1.0 6.0 2.5 7.0 0.0 2.0 5.8 2.3 3.5 5.0 0.0156 9.0
2.0 0.0 6.5 1.5 4.0 0.0 1.0 4.5 2.0 3.3 4.8 10 0.1250 9.0 4.5 3.0
9.0 4.5 8.0 1.0 3.0 5.8 3.0 3.5 5.3 0.0625 7.0 2.0 0.5 9.0 3.5 9.0
0.0 1.0 5.3 2.5 3.3 5.3 0.0313 6.5 1.0 0.0 7.0 2.0 7.0 0.0 0.0 4.5
2.5 3.3 5.3 0.0156 9.0 0.5 0.0 7.0 1.0 3.0 0.0 0.0 4.0 1.8 2.5 4.3
11 0.1250 9.0 9.0 3.0 9.0 6.0 9.0 7.0 9.0 9.0 3.0 6.0 7.5 0.0625
9.0 9.0 0.0 9.0 6.0 9.0 6.0 6.0 9.0 3.0 5.5 7.5 0.0313 9.0 9.0 0.0
9.0 5.0 9.0 0.0 0.0 7.5 2.0 4.5 6.5 0.0156 9.0 1.0 0.0 7.0 3.0 9.0
0.0 0.0 5.0 2.0 4.5 6.5 12 0.1250 9.0 9.0 9.0 9.0 8.0 9.0 9.0 9.0
8.0 5.0 7.5 8.0 0.0625 9.0 7.0 7.0 9.0 7.0 9.0 4.0 9.0 8.5 3.0 7.5
7.5 0.0313 9.0 9.0 3.0 9.0 5.0 9.0 1.0 4.0 7.0 3.0 7.0 7.0 0.0156
9.0 7.0 0.0 9.0 3.0 9.0 0.0 0.0 5.0 2.5 5.5 6.5 13 0.1250 9.0 9.0
3.0 9.0 5.0 9.0 7.0 9.0 7.5 3.0 6.0 8.0 0.0625 9.0 9.0 3.0 9.0 5.0
9.0 3.0 4.0 5.5 2.5 6.0 7.5 0.0313 9.0 9.0 0.0 8.0 3.0 9.0 2.0 4.0
5.5 2.5 4.5 7.0 0.0156 9.0 7.0 0.0 9.0 3.0 9.0 2.0 0.0 5.0 1.5 4.5
7.0 14 0.1250 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0 8.5 8.5 9.0 7.5
0.0625 9.0 9.0 2.0 9.0 5.0 9.0 9.0 9.0 9.0 6.0 7.5 7.5 0.0313 9.0
9.0 2.0 9.0 4.0 9.0 9.0 8.0 8.0 5.5 6.0 7.0 0.0156 9.0 9.0 0.0 9.0
2.0 9.0 9.0 7.0 6.0 3.5 5.5 7.0 15 0.1250 9.0 9.0 4.0 9.0 6.0 9.0
9.0 7.0 5.5 6.5 7.0 7.5 0.0625 9.0 4.0 0.0 9.0 3.0 9.0 3.0 2.0 4.5
6.5 6.5 7.0 0.0313 9.0 0.0 0.0 3.0 0.0 9.0 0.0 0.0 4.0 5.0 6.0 6.0
0.0156 9.0 0.0 0.0 3.0 0.0 6.0 0.0 0.0 3.5 4.5 5.0 5.0 16 0.2500
9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.5 8.5 9.0 0.1250 9.0 9.0 9.0
9.0 8.4 9.0 9.0 9.0 9.0 7.3 7.9 8.7 0.0625 9.0 9.0 8.0 9.0 6.8 9.0
9.0 9.0 8.9 5.7 7.5 8.4 0.0313 9.0 8.0 6.2 8.2 5.3 9.0 8.8 7.8 8.6
4.2 6.5 8.1 0.0157 9.0 9.0 9.0 9.0 5.0 9.0 3.0 9.0 9.0 3.0 7.5 8.0
17 0.1250 9.0 9.0 5.5 8.0 6.0 9.0 8.0 5.5 7.5 5.0 7.3 7.8 0.0625
9.0 6.0 1.0 4.0 5.5 9.0 2.5 4.0 5.8 3.5 5.5 7.8 0.0313 9.0 6.0 1.0
3.0 3.5 8.5 0.0 2.5 5.5 3.0 4.5 7.3 0.0156 9.0 3.0 0.0 2.5 1.5 7.0
0.0 2.0 4.3 1.8 3.3 7.0 18 0.0630 9.0 7.0 1.0 9.0 6.0 9.0 2.0 6.0
3.5 1.5 3.0 4.0 0.0315 9.0 9.0 1.0 9.0 5.0 6.0 1.0 1.0 3.5 1.5 3.0
4.5 0.0158 9.0 4.0 0.0 6.0 2.0 2.0 1.0 0.0 3.5 2.0 2.5 4.0 19
0.0630 9.0 7.0 1.0 9.0 3.0 5.0 2.0 2.0 4.5 2.5 4.5 5.0 0.0315 9.0
3.0 1.0 7.0 3.0 9.0 2.0 2.0 4.5 2.0 4.0 4.5 0.0158 9.0 3.0 0.0 3.0
2.0 2.0 1.0 1.0 3.0 1.5 3.0 4.0 20 0.0630 9.0 6.0 2.0 7.0 6.0 9.0
2.0 4.0 5.5 3.0 4.0 5.5 0.0315 9.0 5.0 0.0 6.0 2.0 3.0 1.0 1.0 4.0
2.0 4.0 5.0 0.0158 9.0 4.0 0.0 4.0 1.0 9.0 1.0 1.0 3.5 2.0 3.5 4.5
21 0.0630 9.0 6.0 0.0 7.0 4.0 9.0 2.0 2.0 4.5 2.5 3.5 4.5 0.0315
7.0 4.0 0.0 5.0 2.0 2.0 2.0 2.0 2.5 2.5 3.5 4.0 0.0158 4.0 4.0 0.0
2.0 2.0 1.0 1.0 0.0 2.0 2.0 2.5 4.0 22 0.0630 9.0 7.0 1.0 3.0 3.0
9.0 1.0 7.0 5.5 4.5 5.0 7.5 0.0315 9.0 6.0 2.0 6.0 4.0 9.0 2.0 5.0
6.5 3.0 3.5 7.5 0.0158 9.0 6.0 1.0 4.0 4.0 9.0 2.0 3.0 5.5 2.5 4.0
7.0 23 0.0630 5.0 7.0 3.0 9.0 9.0 9.0 2.0 4.0 5.0 4.5 5.0 5.0
0.0315 4.0 4.0 1.0 7.0 7.0 9.0 2.0 4.0 3.5 2.5 4.0 3.5 0.0158 3.0
2.0 0.0 2.0 3.0 4.0 0.0 2.0 3.0 2.0 2.5 3.0 24 0.0630 9.0 9.0 0.0
9.0 6.0 0.0 0.0 5.5 3.0 3.5 5.5 0.0315 9.0 3.0 0.0 4.0 4.0 9.0 0.0
0.0 5.0 3.0 3.5 4.5 0.0158 9.0 2.0 0.0 2.0 1.0 2.0 0.0 0.0 4.0 2.5
3.5 4.0 25 0.0625 9.0 9.0 0.0 9.0 7.0 9.0 0.0 0.0 8.0 2.0 3.0 7.0
0.0313 9.0 4.0 0.0 5.0 5.0 9.0 0.0 0.0 7.5 2.0 3.0 5.5 0.0156 9.0
3.0 0.0 2.0 2.0 9.0 0.0 0.0 7.0 0.5 2.0 3.5 26 0.0625 9.0 9.0 0.0
9.0 5.0 9.0 0.0 0.0 6.0 1.5 3.5 5.5 0.0313 9.0 8.0 0.0 9.0 5.0 9.0
0.0 0.0 5.5 1.0 2.5 4.5 0.0156 9.0 9.0 0.0 9.0 3.0 9.0 0.0 0.0 5.5
0.5 1.5 3.5 27 0.0630 9.0 7.0 1.0 9.0 4.0 9.0 1.0 9.0 7.5 4.5 4.5
6.5 0.0315 9.0 5.0 1.0 6.0 4.0 9.0 2.0 4.0 6.5 2.5 4.0 5.5 0.0158
9.0 4.0 1.0 6.0 1.0 9.0 2.0 2.0 6.0 2.0 3.0 5.0 28 0.0630 9.0 9.0
4.0 4.0 8.0 9.0 9.0 9.0 8.5 6.0 6.5 9.0 0.0315 9.0 4.0 1.0 4.0 7.0
9.0 5.0 9.0 8.0 3.5 5.0 7.5 0.0158 9.0 4.0 1.0 2.0 3.0 9.0 0.0 0.0
6.5 2.5 5.0 7.5 29 0.0630 9.0 9.0 0.0 5.0 7.0 9.0 4.0 4.0 8.0 3.5
5.5 7.5 0.0315 7.0 4.0 0.0 1.0 1.0 9.0 1.0 1.0 7.5 3.0 5.0 5.5
0.0158 9.0 1.0 0.0 1.0 1.0 3.0 0.0 0.0 6.5 1.0 4.5 5.5 30 0.0630
9.0 1.0 0.0 3.0 0.0 9.0 0.0 0.0 6.5 3.5 5.5 6.0 0.0315 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 6.5 2.5 4.5 4.5 0.0158 3.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 6.5 2.0 4.0 3.0 31 0.0630 9.0 7.0 0.0 7.0 3.0 9.0 5.0 7.0
7.0 5.5 6.5 8.0 0.0315 9.0 2.0 0.0 2.0 1.0 9.0 0.0 0.0 6.5 4.0 5.5
7.5 0.0158 9.0 0.0 0.0 0.0 0.0 9.0 0.0 0.0 6.5 3.5 5.0 7.0 32
0.1250 9.0 9.0 3.0 6.0 2.0 9.0 2.0 7.0 6.0 3.5 4.0 7.0 0.0625 9.0
3.0 0.0 2.0 0.0 9.0 0.0 0.0 6.0 3.0 4.0 7.0 0.0313 9.0 0.0 0.0 0.0
0.0 9.0 0.0 0.0 5.5 2.0 3.5 6.0 0.0158 5.0 3.0 0.0 3.0 0.0 9.0 0.0
0.0 3.5 1.0 2.0 4.0 33 0.0630 9.0 9.0 5.0 9.0 5.0 9.0 9.0 8.0 8.5
2.0 6.0 8.5 0.0315 9.0 9.0 1.0 9.0 4.0 9.0 9.0 7.0 8.5 2.0 5.5 8.0
0.0158 9.0 9.0 0.0 9.0 3.0 9.0 2.0 4.0 7.0 0.5 3.5 7.5 34 0.0630
9.0 9.0 0.0 9.0 6.0 9.0 1.0 9.0 7.0 3.5 5.0 7.0 0.0315 9.0 9.0 0.0
9.0 9.0 9.0 0.0 4.0 7.0 2.0 4.0 6.5 0.0158 9.0 9.0 0.0 7.0 4.0 9.0
0.0 0.0 7.0 1.0 4.0 5.5 35 0.0630 9.0 9.0 9.0 9.0 5.0 9.0 1.0 4.0
9.0 3.5 3.5 4.5 0.0315 9.0 9.0 3.0 9.0 5.0 9.0 0.0 2.0 7.5 3.0 3.0
3.5 0.0158 9.0 9.0 0.0 7.0 4.0 9.0 0.0 0.0 7.0 2.0 2.5 3.5 36
0.0630 9.0 9.0 0.0 4.0 4.0 9.0 9.0 9.0 8.0 6.0 3.5 7.5 0.0315 9.0
3.0 0.0 3.0 1.0 9.0 2.0 9.0 5.5 1.0 2.5 6.0 0.0158 9.0 2.0 0.0 2.0
0.0 9.0 0.0 3.0 5.0 0.5 1.5 4.5 37 0.0630 9.0 9.0 0.0 3.0 4.0 9.0
0.0 0.0 5.0 1.5 2.0 4.0 0.0315 9.0 9.0 0.0 3.0 3.0 9.0 0.0 0.0 5.0
1.0 2.0 4.0 0.0158 9.0 3.0 0.0 3.0 1.0 9.0 0.0 0.0 4.5 0.5 2.0 3.5
38 0.2500 9.0 9.0 3.0 9.0 8.0 9.0 9.0 9.0 8.5 7.5 8.0 7.5 0.1250
9.0 9.0 3.0 6.0 3.0 9.0 5.0 9.0 8.5 6.0 8.0 7.5 0.0625 9.0 5.0 2.0
4.0 3.0 9.0 2.0 5.0 8.0 2.5 6.5 7.5 0.0313 9.0 5.0 1.0 3.0 1.0 9.0
2.0 3.0 6.5 0.5 5.5 7.5 0.0156 9.0 3.0 0.0 1.0 0.0 9.0 0.0 0.0 6.5
0.5 5.0 7.5 39 0.0630 9.0 7.0 0.0 1.0 0.0 7.0 0.0 0.0 5.0 2.0 2.5
3.0 0.0315 9.0 3.0 0.0 1.0 0.0 7.0 0.0 0.0 5.0 1.5 1.5 3.0 0.0158
0.0 0.0 0.0 1.0 0.0 2.0 0.0 0.0 4.5 1.5 2.0 3.0 40 0.0630 9.0 9.0
5.0 9.0 4.0 9.0 9.0 9.0 8.0 3.0 4.5 8.5 0.0315 9.0 9.0 2.0 7.0 2.0
9.0 7.0 7.0 9.0 3.0 4.0 7.5 0.0158 9.0 9.0 0.0 2.0 1.0 9.0 1.0 1.0
7.0 2.5 4.0 7.0 41 0.0630 9.0 9.0 5.0 9.0 5.0 9.0 9.0 9.0 9.0 3.5
5.0 7.5 0.0315 9.0 9.0 1.0 7.0 2.0 9.0 7.0 3.0 8.0 3.5 4.0 8.0
0.0158 9.0 9.0 1.0 3.0 1.0 9.0 2.0 1.0 8.0 2.5 4.0 7.0 42 0.0630
9.0 9.0 7.0 6.0 3.0 9.0 4.0 1.0 6.5 3.0 3.5 4.5 0.0315 9.0 9.0 3.0
9.0 3.0 9.0 2.0 1.0 6.0 2.5 3.5 4.5 0.0158 9.0 9.0 4.0 3.0 1.0 9.0
1.0 0.0 5.5 2.5 3.5 4.5 43 0.0630 9.0 9.0 9.0 9.0 4.0 9.0 0.0 8.0
7.0 3.0 4.0 5.5 0.0315 9.0 9.0 9.0 9.0 4.0 9.0 0.0 3.0 7.0 2.0 3.5
5.0 0.0158 9.0 9.0 9.0 5.0 0.0 9.0 0.0 3.0 7.5 1.0 3.0 4.5 44
0.1250 9.0 9.0 2.0 9.0 1.0 9.0 1.0 2.0 6.0 4.0 4.0 5.0 0.0625 9.0
7.0 2.0 5.0 1.0 9.0 2.0 2.0 5.5 4.0 4.0 5.0 0.0313 7.0 4.0 0.0 4.0
1.0 9.0 1.0 0.0 5.0 4.0 4.0 5.0 0.0156 9.0 4.0 0.0 1.0 0.0 9.0 0.0
0.0 4.5 3.0 3.0 5.0 45 0.0625 9.0 9.0 0.0 9.0 0.0 9.0 0.0 2.0 7.0
2.0 4.5 5.5 0.0313 9.0 4.0 0.0 5.0 0.0 9.0 0.0 0.0 6.5 1.5 4.0 5.0
0.0156 9.0 0.0 0.0 0.0 9.0 0.0 0.0 5.5 1.5 4.0 4.5 46 0.0625 9.0
5.0 0.0 0.0 0.0 9.0 0.0 0.0 5.5 1.5 3.0 5.0 0.0313 4.0 0.0 0.0 0.0
0.0 3.0 0.0 0.0 5.0 1.0 2.0 4.5 47 0.0625 9.0 9.0 2.0 3.0 9.0 0.0
0.0 7.5 3.0 4.5 7.5 0.0313 9.0 9.0 2.0 4.0 3.0 9.0 0.0 0.0 7.0 1.5
3.5 7.0 0.0156 9.0 3.0 0.0 3.0 0.0 9.0 0.0 0.0 5.5 0.5 2.5 5.0 48
0.0625 9.0 9.0 3.0 4.0 0.0 9.0 2.0 2.0 7.5 2.0 5.0 6.5 0.0313 9.0
5.0 2.0 4.0 0.0 9.0 2.0 0.0 6.0 0.5 5.0 5.5 0.0156 9.0 3.0 0.0 3.0
0.0 9.0 0.0 0.0 5.5 0.5 5.0 5.5 49 0.0625 9.0 9.0 3.0 9.0 4.0 9.0
0.0 7.0 8.0 3.0 4.5 6.0 0.0313 9.0 9.0 3.0 9.0 4.0 9.0 0.0 4.0 7.5
2.5 4.5 5.5 0.0156 9.0 9.0 2.0 9.0 2.0 9.0 0.0 3.0 7.5 1.0 4.0 5.0
50 0.0625 9.0 9.0 2.0 5.0 4.0 9.0 2.0 2.0 5.5 2.0 4.5 5.5 0.0313
9.0 9.0 1.0 3.0 2.0 9.0 0.0 0.0 5.5 1.0 3.5 5.0 0.0156 6.0 9.0 0.0
0.0 0.0 9.0 0.0 0.0 5.5 1.0 3.0 5.0 51 0.0630 9.0 9.0 7.0 9.0 9.0
9.0 9.0 9.0 8.0 4.0 7.0 7.5 0.0315 9.0 6.0 2.0 9.0 9.0 9.0 5.0 9.0
8.0 3.5 5.5 7.5 0.0158 9.0 6.0 2.0 9.0 4.0 9.0 4.0 7.0 6.0 2.0 4.0
7.0 52 0.0630 9.0 5.0 2.0 6.0 5.0 9.0 4.0 7.0 6.0 2.0 4.5 7.0
0.0315 9.0 3.0 1.0 4.0 4.0 9.0 1.0 3.0 6.0 1.0 3.0 7.5 0.0158 1.0
1.0 1.0 4.0 1.0 4.0 1.0 1.0 5.0 1.0 2.5 5.0 53 0.0630 9.0 9.0 9.0
9.0 9.0 9.0 9.0 7.0 9.0 3.5 4.0 8.0 0.0315 9.0 9.0 7.0 9.0 7.0 9.0
3.0 6.0 9.0 2.5 3.0 7.5 0.0158 9.0 9.0 4.0 7.0 3.0 9.0 2.0 6.0 9.0
2.0 2.5 5.5 54 0.0630 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 6.5 9.0
9.0 0.0315 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 7.0 8.0 0.0158
9.0 9.0 5.0 9.0 6.0 9.0 9.0 9.0 9.0 3.0 5.0 7.5 55 0.2500 9.0 9.0
9.0 9.0 9.0 9.0 9.0 9.0 8.0 6.5 7.5 9.0 0.1250 9.0 9.0 8.0 9.0 9.0
9.0 9.0 9.0 8.3 5.5 7.5 8.8 0.0625 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0
8.0 4.2 7.5 8.7 0.0313 9.0 9.0 7.7 9.0 3.3 9.0 9.0 9.0 8.2 3.5 6.8
8.3 0.0158 8.0 9.0 1.0 9.0 6.0 9.0 9.0 9.0 8.0 2.5 5.5 7.5 56
0.0630 9.0 9.0 9.0 9.0 9.0 9.0 3.0 7.0 8.0 2.5 5.0 6.5 0.0315 9.0
9.0 4.0 9.0 6.0 9.0 2.0 6.0 7.5 2.0 4.5 5.5 0.0158 9.0 9.0 4.0 9.0
3.0 9.0 2.0 6.0 7.0 1.5 4.0 5.0 57 0.0630 9.0 9.0 6.0 9.0 5.0 9.0
1.0 5.0 9.0 3.0 4.0 5.0 0.0315 9.0 9.0 2.0 9.0 6.0 9.0 1.0 4.0 6.5
2.5 4.0 5.0 0.0158 9.0 9.0 2.0 9.0 4.0 9.0 1.0 2.0 6.5 1.5 3.0 4.5
58 0.0630 9.0 9.0 3.0 9.0 9.0 9.0 9.0 9.0 8.5 6.0 7.5 8.0 0.0315
9.0 9.0 2.0 9.0 3.0 9.0 7.0 9.0 7.0 5.5 5.0 7.0 0.0158 9.0 9.0 0.0
9.0 1.0 9.0 7.0 9.0 7.0 5.5 5.0 7.0 59 0.0630 9.0 9.0 9.0 9.0 9.0
9.0 9.0 9.0 9.0 5.5 9.0 8.5 0.0315 9.0 9.0 9.0 9.0 6.0 9.0 9.0 9.0
9.0 6.0 8.0 8.0 0.0158 9.0 9.0 3.0 9.0 6.0 9.0 9.0 9.0 8.0 4.5 8.0
7.5 60 0.0630 9.0 9.0 3.0 9.0 5.0 9.0 0.0 5.0 7.0 5.0 4.5 5.5
0.0315 9.0 9.0 0.0 4.0 2.0 9.0 0.0 4.0 6.5 3.0 4.5 5.0 0.0158 9.0
7.0 0.0 4.0 0.0 9.0 0.0 0.0 6.5 3.0 4.5 5.0 61 0.0630 0.0 0.0 0.0
0.0 0.0 1.0 0.0 2.0 4.0 1.5 1.5 3.0 0.0315 0.0 0.0 0.0 0.0 0.0 2.0
0.0 0.0 3.0 0.5 0.5 2.0 0.0158 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 2.0
0.5 0.5 2.0 62 0.0630 9.0 9.0 6.0 9.0 5.0 9.0 7.0 8.0 8.5 7.0 7.0
8.0 0.0315 9.0 7.0 2.0 9.0 5.0 9.0 6.0 9.0 7.5 5.0 5.5 8.0 0.0158
9.0 9.0 1.0 9.0 1.0 9.0 4.0 9.0 7.5 4.5 5.0 7.5 63 0.0630 9.0 9.0
5.0 7.0 7.0 9.0 6.0 9.0 7.5 6.0 7.0 7.5 0.0315 6.0 6.0 3.0 9.0 6.0
9.0 2.0 9.0 8.5 5.0 6.0 7.5 0.0158 9.0 6.0 0.0 9.0 1.0 9.0 2.0 9.0
6.5 5.0 5.5 7.0 64 0.0630 9.0 9.0 3.0 9.0 7.0 9.0 7.0 9.0 7.5 6.0
7.0 8.0 0.0315 9.0 9.0 2.0 9.0 7.0 9.0 5.0 7.0 7.5 6.0 6.0 8.0
0.0158 9.0 9.0 2.0 9.0 5.0 9.0 3.0 6.0 7.0 6.0 6.0 7.0 65 0.0630
9.0 9.0 3.0 9.0 9.0 9.0 7.0 9.0 7.5 6.0 7.0 7.5 0.0315 9.0 7.0 2.0
9.0 5.0 9.0 7.0 7.0 8.0 6.0 7.0 8.0 0.0158 9.0 9.0 0.0 9.0 2.0 9.0
3.0 7.0 7.5 4.0 4.0 8.0 66 0.1250 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0
9.0 5.5 7.5 9.0 0.0625 9.0 9.0 3.0 9.0 4.0 9.0 9.0 9.0 8.5 5.5 8.0
9.0 0.0313 9.0 9.0 0.0 9.0 3.0 9.0 9.0 9.0 8.5 5.0 7.0 8.5 0.0158
9.0 6.0 0.0 5.0 2.0 9.0 2.0 2.0 7.0 3.5 3.5 7.0 67 0.0630 9.0 7.0
3.0 9.0 5.0 9.0 7.0 9.0 7.5 5.0 6.5 8.0 0.0315 9.0 7.0 2.0 6.0 6.0
9.0 6.0 9.0 7.5 4.5 6.0 8.0 0.0158 5.0 6.0 0.0 4.0 2.9 9.0 3.0 9.0
8.5 4.0 5.0 7.5 68 0.0630 7.0 9.0 7.0 7.0 4.0 9.0 5.0 6.0 7.0 4.0
4.0 5.5 0.0315 9.0 9.0 4.0 7.0 3.0 9.0 2.0 6.0 5.5 3.5 3.5 5.0
0.0158 7.0 9.0 1.0 4.0 2.0 9.0 2.0 2.0 6.0 3.0 3.0 5.0 69 0.0630
9.0 9.0 2.0 5.0 9.0 4.0 1.0 6.0 4.5 4.5 5.5 0.0315 9.0 9.0 2.0 9.0
1.0 9.0 1.0 1.0 6.0 3.0 3.0 4.5 0.0158 9.0 9.0 1.0 7.0 0.0 9.0 2.0
3.0 5.5 2.5 3.0 4.5 70 0.0630 9.0 7.0 3.0 3.0 9.0 9.0 9.0 7.0 5.0
5.5 7.0 0.0315 6.0 6.0 0.0 9.0 0.0 9.0 2.0 2.0 5.5 3.5 4.0 5.5
0.0158 1.0 6.0 0.0 4.0 0.0 9.0 0.0 1.0 4.5 2.5 2.5 4.0 71 0.0630
9.0 9.0 4.0 7.0 9.0 4.0 9.0 7.5 4.5 4.5 7.0 0.0315 9.0 9.0 3.0 7.0
6.0 9.0 4.0 7.0 7.5 3.5 3.5 5.0 0.0158 9.0 9.0 2.0 6.0 4.0 9.0 4.0
4.0 6.5 3.0 2.5 5.0 72 0.0630 9.0 6.0 7.0 9.0 9.0 3.0 2.0 7.0 4.5
4.5 6.5 0.0315 9.0 9.0 6.0 9.0 7.0 7.0 3.0 4.0 5.5 3.5 4.0 4.5
0.0158 9.0 5.0 8.0 7.0 6.0 9.0 1.0 2.0 5.5 3.5 3.5 4.0 73 0.0630
9.0 9.0 7.0 9.0 6.0 9.0 3.0 7.0 7.5 4.0 5.0 5.0 0.0315 9.0 9.0 7.0
9.0 7.0 9.0 2.0 2.0 5.5 3.0 4.0 4.5 0.0158 9.0 9.0 1.0 4.0 3.0 9.0
2.0 1.0 6.0 2.5 3.5 4.5 74 0.0630 9.0 9.0 9.0 9.0 9.0 1.0 2.0 6.5
5.5 6.0 5.5 0.0315 9.0 9.0 4.0 9.0 4.0 9.0 1.0 1.0 5.0 4.5 4.5 5.0
0.0158 9.0 9.0 3.0 9.0 1.0 9.0 1.0 1.0 5.5 3.5 3.5 4.5 75 0.0630
9.0 9.0 3.0 7.0 5.0 9.0 1.0 3.0 5.0 2.5 2.5 5.0 0.0315 9.0 5.0 1.0
7.0 2.0 7.0 1.0 5.0 4.5 2.5 2.5 4.5 0.0158 9.0 7.0 1.0 7.0 1.0 7.0
1.0 1.0 4.0 2.0 2.5 4.0 76 0.0630 9.0 9.0 5.0 7.0 7.0 9.0 2.0 9.0
6.0 5.0 5.5 7.0 0.0315 9.0 9.0 4.0 7.0 6.0 9.0 1.0 2.0 5.5 4.0 5.0
6.0 0.0158 9.0 9.0 1.0 3.0 1.0 9.0 1.0 1.0 4.0 3.0 3.5 4.5 77
0.0630 9.0 9.0 1.0 9.0 7.0 9.0 1.0 7.0 5.0 3.0 3.0 4.5 0.0315 9.0
9.0 1.0 9.0 1.0 9.0 1.0 6.0 5.0 2.0 2.5 3.5 0.0158 9.0 9.0 1.0 6.0
1.0 9.0 1.0 1.0 3.5 2.0 3.0 4.0 78 0.0630 9.0 9.0 3.0 9.0 2.0 9.0
1.0 1.0 5.5 4.0 3.5 5.0 0.0315 9.0 7.0 1.0 9.0 1.0 9.0 1.0 1.0 4.5
3.5 3.5 5.0 0.0158 7.0 7.0 1.0 9.0 1.0 9.0 1.0 1.0 4.0 3.0 3.0 4.5
79 0.0630 9.0 9.0 1.0 7.0 1.0 9.0 1.0 1.0 5.0 4.0 5.0 5.0 0.0315
9.0 7.0 1.0 7.0 2.0 9.0 1.0 1.0 5.0 2.5 2.5 4.5 0.0158 9.0 6.0 1.0
1.0 1.0 9.0 1.0 4.0 4.5 2.5 3.0 5.0 80 0.0630 9.0 7.0 9.0 9.0 5.0
9.0 3.0 4.0 6.5 4.0 4.0 5.5 0.0315 9.0 9.0 5.0 9.0 4.0 9.0 2.0 2.0
5.5 3.5 3.5 5.0 0.0158 9.0 9.0 1.0 9.0 2.0 9.0 1.0 1.0 4.5 3.5 3.5
5.0
81 0.0630 9.0 9.0 5.0 4.0 9.0 6.0 9.0 6.5 5.5 6.0 7.0 0.0315 7.0
9.0 2.0 3.0 5.0 9.0 2.0 1.0 6.5 4.5 5.0 7.0 0.0158 7.0 9.0 1.0 4.0
1.0 9.0 1.0 1.0 6.5 4.5 4.5 6.5 82 0.0630 9.0 9.0 9.0 9.0 9.0 9.0
9.0 9.0 9.0 8.5 8.5 9.0 0.0315 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
3.0 7.5 8.5 0.0158 9.0 9.0 9.0 7.0 4.0 9.0 9.0 9.0 8.5 3.0 7.5 8.5
83 0.1250 9.0 9.0 9.0 9.0 5.0 9.0 9.0 8.0 8.5 3.0 6.5 7.5 0.0625
9.0 9.0 7.0 9.0 3.0 9.0 4.0 8.0 8.0 3.0 4.5 7.5 0.0313 9.0 9.0 9.0
7.0 0.0 9.0 2.0 2.0 6.5 2.5 4.0 7.5 0.0156 9.0 9.0 0.0 5.0 0.0 9.0
0.0 0.0 4.5 1.5 3.5 4.5 84 0.1250 9.0 9.0 3.0 9.0 7.0 9.0 0.0 2.0
8.5 3.0 5.0 5.0 0.0625 9.0 9.0 0.0 9.0 4.0 9.0 0.0 0.0 4.5 1.5 4.5
4.5 0.0313 9.0 9.0 0.0 7.0 2.0 9.0 0.0 0.0 4.5 1.0 3.5 4.0 0.0156
9.0 4.0 0.0 6.0 1.0 9.0 0.0 0.0 4.0 0.5 3.0 4.0 85 0.1250 9.0 9.0
2.0 9.0 5.0 9.0 9.0 9.0 7.5 2.5 5.0 8.5 0.0625 9.0 9.0 0.0 4.0 3.0
9.0 0.0 9.0 6.0 1.5 4.5 7.5 0.0313 9.0 9.0 0.0 4.0 1.0 9.0 0.0 0.0
6.0 1.0 3.5 6.5 0.0156 9.0 9.0 0.0 2.0 0.0 9.0 0.0 0.0 4.5 1.0 3.0
4.0 86 0.1250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.5 8.5 9.0
0.0625 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 9.0 7.5 7.5 8.5 0.0313 9.0
9.0 2.0 9.0 5.0 9.0 9.0 9.0 9.0 7.5 7.0 8.0 0.0156 9.0 9.0 1.0 9.0
2.0 9.0 3.0 8.0 8.5 3.0 6.0 7.5 87 0.2500 9.0 9.0 9.0 9.0 3.0 9.0
9.0 7.0 9.0 4.0 6.0 8.0 0.1250 9.0 9.0 2.0 4.0 1.0 9.0 9.0 7.0 8.0
1.5 4.5 7.5 0.0625 9.0 7.0 0.0 3.0 1.0 9.0 2.0 2.0 7.5 1.0 4.5 5.5
0.0313 4.0 4.0 0.0 0.0 0.0 9.0 0.0 0.0 5.5 0.5 3.0 4.5 0.0156 2.0
0.0 0.0 0.0 0.0 9.0 0.0 0.0 4.5 0.0 2.5 4.0 88 0.0630 9.0 9.0 3.0
9.0 4.0 9.0 7.0 9.0 9.0 6.0 7.5 9.0 0.0315 9.0 9.0 3.0 9.0 4.0 9.0
7.0 9.0 8.5 5.5 7.0 8.5 0.0158 9.0 9.0 0.0 9.0 4.0 9.0 1.0 9.0 8.5
2.0 5.5 7.5 89 0.1250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0
9.0 0.0625 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 9.0 6.5 7.0 8.5 0.0313
9.0 9.0 6.0 9.0 4.0 9.0 9.0 9.0 9.0 4.0 7.0 7.5 0.0158 9.0 4.0 0.0
4.0 3.0 9.0 2.0 7.0 7.5 1.0 5.5 7.5 90 0.0630 9.0 9.0 4.0 9.0 7.0
9.0 9.0 9.0 9.0 6.5 7.5 9.0 0.0315 9.0 9.0 3.0 7.0 7.0 9.0 5.0 9.0
9.0 6.5 7.0 8.5 0.0158 9.0 9.0 2.0 5.0 5.0 9.0 3.0 9.0 9.0 4.0 5.5
8.0 91 0.0630 9.0 4.0 4.0 3.0 0.0 9.0 0.0 0.0 5.5 2.0 4.0 5.0
0.0315 9.0 0.0 0.0 3.0 0.0 9.0 0.0 0.0 4.5 1.0 3.0 4.0 0.0158 7.0
0.0 0.0 0.0 0.0 7.0 0.0 0.0 4.5 1.0 2.5 4.0 92 0.0630 9.0 9.0 9.0
9.0 4.0 9.0 1.0 9.0 9.0 3.5 6.5 8.0 0.0315 9.0 9.0 5.0 9.0 3.0 9.0
1.0 9.0 9.0 2.0 6.0 7.5 0.0158 9.0 0.0 3.0 2.0 0.0 9.0 0.0 0.0 7.5
1.5 5.0 6.0 93 0.0630 9.0 9.0 2.0 9.0 6.0 9.0 7.0 9.0 9.0 6.0 7.5
8.0 0.0315 9.0 9.0 1.0 4.0 5.0 9.0 2.0 9.0 9.0 4.0 6.0 7.5 0.0158
9.0 9.0 0.0 4.0 0.0 9.0 0.0 9.0 8.5 1.0 5.0 7.5 94 0.0630 9.0 9.0
9.0 9.0 4.0 9.0 9.0 9.0 9.0 5.0 8.0 9.0 0.0315 9.0 9.0 3.0 9.0 4.0
9.0 7.0 9.0 9.0 4.5 9.0 8.5 0.0158 9.0 7.0 0.0 9.0 3.0 9.0 1.0 9.0
9.0 2.0 6.0 8.5 95 0.1250 9.0 9.0 3.0 6.0 3.0 9.0 2.0 3.0 9.0 4.0
4.0 5.5 0.0625 9.0 6.0 3.0 7.0 0.0 9.0 1.0 9.0 7.0 2.5 3.5 5.5
0.0313 9.0 6.0 0.0 4.0 1.0 9.0 1.0 2.0 6.5 2.5 3.0 4.0 0.0156 5.0
1.0 0.0 1.0 0.0 6.0 0.0 0.0 4.5 1.5 2.5 4.5 96 0.1250 9.0 7.0 0.0
0.0 9.0 2.0 4.0 3.0 2.0 3.0 5.0 0.0625 9.0 7.0 1.0 1.0 9.0 2.0 7.0
4.0 1.5 2.5 4.5 0.0313 7.0 4.0 0.0 2.0 0.0 9.0 0.0 1.0 4.5 2.0 2.5
4.5 0.0156 1.0 3.0 0.0 2.0 0.0 6.0 0.0 0.0 4.0 2.0 2.0 4.5 97
0.1250 9.0 7.0 1.0 7.0 1.0 9.0 6.0 9.0 6.5 3.0 4.0 5.0 0.0625 7.0
4.0 0.0 4.0 1.0 9.0 3.0 9.0 5.5 2.5 2.5 4.0 0.0313 4.0 1.0 0.0 1.0
0.0 9.0 1.0 6.0 4.0 0.5 1.5 4.0 0.0156 4.0 0.0 0.0 0.0 0.0 7.0 1.0
1.0 4.5 0.5 1.0 3.5 98 0.1250 9.0 9.0 1.0 9.0 1.0 9.0 1.0 2.0 5.5
2.0 3.0 5.0 0.0625 9.0 4.0 0.0 3.0 0.0 9.0 1.0 1.0 5.5 2.5 3.0 4.0
0.0313 7.0 3.0 0.0 1.0 0.0 3.0 0.0 0.0 4.5 2.5 2.5 4.0 0.0156 2.0
3.0 0.0 0.0 0.0 3.0 0.0 1.0 4.5 1.5 2.5 3.0 99 0.1250 9.0 9.0 9.0
9.0 9.0 9.0 6.0 8.0 8.0 6.5 6.5 8.0 0.0625 9.0 9.0 8.0 9.0 7.0 9.0
7.0 9.0 8.0 5.5 5.5 7.5 0.0313 9.0 9.0 7.0 7.0 6.0 9.0 4.0 7.0 7.5
4.5 4.5 6.0 0.0156 9.0 9.0 4.0 7.0 3.0 9.0 4.0 6.0 6.5 4.0 4.0 5.0
100 0.1250 9.0 7.0 9.0 9.0 3.0 9.0 7.0 7.0 7.0 3.5 4.0 5.0 0.0625
9.0 9.0 6.0 7.0 3.0 9.0 4.0 6.0 6.5 3.5 3.5 5.0 0.0313 9.0 9.0 7.0
7.0 2.0 9.0 3.0 9.0 6.0 3.5 4.0 5.0 0.0156 9.0 9.0 2.0 5.0 1.0 5.0
1.0 2.0 5.5 3.0 3.0 4.5 101 0.1250 9.0 9.0 3.0 7.0 2.0 9.0 5.0 5.0
6.5 4.0 5.0 5.0 0.0625 9.0 9.0 2.0 4.0 1.0 9.0 3.0 5.0 6.0 4.0 4.0
5.0 0.0313 7.0 7.0 0.0 4.0 1.0 9.0 2.0 1.0 5.5 3.0 3.5 4.5 0.0156
3.0 9.0 0.0 4.0 0.0 4.0 1.0 2.0 5.5 2.5 3.0 4.5 102 0.1250 9.0 9.0
3.0 7.0 4.0 9.0 6.0 4.0 7.5 3.0 4.5 6.5 0.0625 9.0 7.0 1.0 6.0 1.0
9.0 2.0 2.0 6.0 3.0 4.5 5.5 0.0313 9.0 9.0 1.0 4.0 1.0 9.0 1.0 1.0
5.0 3.0 3.0 5.0 0.0156 7.0 7.0 0.0 3.0 1.0 9.0 0.0 0.0 5.0 2.5 3.0
4.5 103 0.1250 9.0 9.0 3.0 9.0 7.0 9.0 9.0 9.0 9.0 3.5 7.5 8.5
0.0625 9.0 9.0 3.0 5.0 5.0 9.0 9.0 9.0 9.0 2.5 7.5 8.5 0.0313 9.0
9.0 3.0 3.0 3.0 9.0 9.0 5.0 7.0 2.0 6.0 7.5 0.0156 9.0 9.0 0.0 3.0
0.0 9.0 3.0 4.0 8.0 1.5 3.5 5.5 104 0.1250 9.0 9.0 1.0 5.0 2.0 9.0
3.0 4.0 8.5 2.0 4.0 8.0 0.0625 9.0 9.0 0.0 4.0 1.0 9.0 0.0 3.0 7.0
1.0 4.0 6.0 0.0313 7.0 9.0 0.0 2.0 0.0 9.0 0.0 0.0 5.5 0.5 3.0 4.5
0.0156 7.0 3.0 0.0 0.0 0.0 9.0 0.0 0.0 4.5 0.0 3.0 4.5 105 0.1250
9.0 9.0 1.0 2.0 2.0 9.0 3.0 5.0 7.5 2.0 3.5 7.0 0.0625 4.0 3.0 0.0
2.0 1.0 9.0 0.0 2.0 6.5 0.0 3.5 6.0 0.0313 4.0 0.0 0.0 0.0 0.0 9.0
0.0 0.0 4.5 0.0 3.0 5.0 0.0156 4.0 0.0 0.0 0.0 0.0 5.0 0.0 0.0 3.0
0.0 3.5 3.5 106 0.0630 9.0 9.0 3.0 7.0 1.0 9.0 7.0 9.0 6.0 4.0 4.5
7.0 0.0315 9.0 7.0 1.0 7.0 1.0 9.0 2.0 3.0 5.5 2.5 3.0 6.5 0.0158
9.0 7.0 1.0 7.0 1.0 9.0 2.0 4.0 4.5 2.0 2.5 5.0 107 0.0630 9.0 2.0
0.0 1.0 0.0 9.0 3.0 9.0 5.5 4.5 5.0 7.0 0.0315 7.0 2.0 0.0 2.0 0.0
7.0 1.0 9.0 5.0 2.0 3.0 6.0 0.0158 9.0 2.0 0.0 2.0 0.0 9.0 1.0 1.0
4.5 2.0 2.0 4.0 108 0.0630 9.0 5.0 1.0 9.0 3.0 9.0 4.0 7.0 6.0 3.5
4.5 6.5 0.0315 9.0 5.0 1.0 7.0 1.0 9.0 4.0 6.0 5.5 3.0 3.5 6.0
0.0158 9.0 4.0 1.0 4.0 1.0 9.0 3.0 4.0 5.0 3.0 3.0 5.0 109 0.0630
9.0 9.0 9.0 9.0 5.0 9.0 3.0 9.0 8.0 5.0 4.5 7.0 0.0315 9.0 9.0 7.0
9.0 3.0 9.0 3.0 7.0 8.0 4.5 4.0 6.5 0.0158 9.0 9.0 1.0 9.0 1.0 9.0
0.0 6.0 7.0 3.0 3.0 6.5 110 0.0630 9.0 9.0 1.0 9.0 4.0 9.0 4.0 9.0
6.5 3.5 4.0 7.0 0.0315 9.0 4.0 1.0 9.0 3.0 9.0 5.0 9.0 6.5 3.5 3.5
6.5 0.0158 9.0 5.0 1.0 9.0 1.0 9.0 1.0 1.0 5.0 2.5 2.5 5.0 111
0.0630 9.0 9.0 1.0 7.0 1.0 9.0 9.0 9.0 6.0 4.5 5.5 7.0 0.0315 9.0
6.0 1.0 6.0 0.0 9.0 4.0 9.0 6.0 4.5 4.5 6.5 0.0158 7.0 4.0 0.0 2.0
0.0 4.0 3.0 1.0 6.0 2.5 2.5 6.5 112 0.0630 9.0 9.0 2.0 9.0 2.0 9.0
4.0 6.0 6.0 2.5 3.0 5.0 0.0315 9.0 9.0 1.0 9.0 2.0 9.0 4.0 9.0 5.0
2.0 2.0 4.5 0.0158 9.0 5.0 1.0 4.0 0.0 9.0 2.0 3.0 5.5 2.0 2.0 4.5
113 0.0630 9.0 9.0 4.0 7.0 2.0 9.0 1.0 3.0 5.5 2.5 3.0 4.5 0.0315
9.0 9.0 0.0 4.0 0.0 9.0 1.0 5.5 2.0 2.0 4.5 0.0158 9.0 5.0 0.0 5.0
1.0 7.0 0.0 3.0 4.5 2.0 2.0 4.0 114 0.0630 9.0 7.0 1.0 9.0 3.0 9.0
4.0 9.0 6.5 3.0 4.0 7.0 0.0315 9.0 9.0 1.0 6.0 1.0 9.0 1.0 3.0 5.5
2.0 3.0 7.0 0.0158 9.0 4.0 1.0 7.0 1.0 9.0 0.0 4.0 6.0 1.5 2.0 6.5
115 0.0630 9.0 7.0 1.0 4.0 2.0 9.0 3.0 9.0 5.0 2.5 3.0 7.0 0.0315
9.0 6.0 1.0 1.0 0.0 9.0 2.0 4.0 5.0 2.0 2.5 6.5 0.0158 3.0 1.0 0.0
0.0 0.0 9.0 0.0 0.0 5.0 1.5 1.5 5.0 116 0.0630 9.0 7.0 1.0 9.0 0.0
9.0 2.0 3.0 5.5 2.0 2.5 4.5 0.0315 9.0 9.0 1.0 5.0 0.0 9.0 1.0 3.0
5.5 2.0 2.5 4.5 0.0158 9.0 9.0 1.0 4.0 0.0 9.0 3.0 1.0 5.5 1.5 1.5
4.5 117 0.0630 9.0 7.0 1.0 9.0 1.0 9.0 1.0 2.0 6.0 3.0 3.5 5.0
0.0315 9.0 5.0 1.0 4.0 1.0 9.0 2.0 2.0 5.0 2.0 3.5 5.0 0.0158 9.0
4.0 0.0 0.0 1.0 9.0 1.0 1.0 5.0 2.0 3.0 4.5 118 0.0630 9.0 2.0 0.0
5.0 1.0 9.0 1.0 4.0 6.0 2.0 2.0 4.5 0.0315 4.0 2.0 0.0 0.0 0.0 7.0
1.0 0.0 5.0 2.0 2.0 4.0 0.0158 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 4.5
2.0 2.0 3.5 119 0.0625 9.0 9.0 7.0 9.0 3.0 9.0 1.0 9.0 8.5 3.0 3.5
6.0 0.0313 9.0 9.0 5.0 9.0 1.0 9.0 0.0 9.0 8.5 2.0 3.5 5.5 0.0156
9.0 9.0 3.0 9.0 1.0 9.0 0.0 3.0 7.0 1.5 2.5 4.5 120 0.0625 9.0 9.0
8.0 9.0 3.0 9.0 5.0 9.0 9.0 2.5 5.0 8.0 0.0313 9.0 9.0 5.0 9.0 3.0
9.0 2.0 9.0 9.0 2.5 4.5 7.0 0.0156 9.0 9.0 3.0 9.0 2.0 9.0 1.0 4.0
7.5 2.0 3.5 6.0 121 0.0625 9.0 9.0 7.0 9.0 3.0 9.0 0.0 9.0 8.0 3.0
5.0 6.0 0.0313 9.0 9.0 1.0 7.0 0.0 9.0 0.0 8.0 8.0 2.5 4.0 5.0
0.0156 9.0 9.0 0.0 4.0 0.0 9.0 0.0 8.0 6.0 2.0 3.0 5.0 122 0.1250
9.0 9.0 4.0 9.0 6.0 9.0 5.0 9.0 6.5 5.0 5.0 7.0 0.0625 9.0 9.0 3.0
9.0 4.0 9.0 4.0 9.0 6.5 3.5 4.5 7.0 0.0313 9.0 9.0 3.0 9.0 2.0 9.0
3.0 7.0 6.5 3.5 3.5 7.0 0.0156 9.0 7.0 1.0 6.0 2.0 9.0 2.0 6.0 5.5
3.5 3.0 4.5 123 0.1250 9.0 9.0 8.0 9.0 7.0 9.0 9.0 9.0 9.0 5.5 6.5
7.5 0.0625 9.0 9.0 9.0 9.0 6.0 9.0 7.0 9.0 8.0 5.5 6.0 7.5 0.0313
9.0 9.0 3.0 9.0 4.0 9.0 5.0 9.0 6.5 4.0 4.5 7.0 0.0156 9.0 9.0 3.0
9.0 2.0 9.0 5.0 9.0 6.5 4.0 4.0 6.5 124 0.0625 9.0 9.0 3.0 9.0 6.0
9.0 5.0 5.0 7.0 3.0 5.0 8.0 0.0313 9.0 9.0 2.0 9.0 1.0 9.0 3.0 5.0
7.3 3.0 4.3 7.3 0.0156 7.0 9.0 2.0 9.0 0.0 9.0 3.0 3.0 6.7 3.3 3.7
6.3 125 0.0625 9.0 8.0 2.0 9.0 5.0 9.0 3.0 5.0 8.7 3.7 5.0 8.0
0.0313 9.0 8.0 2.0 9.0 2.0 9.0 2.0 5.0 8.0 4.0 5.0 7.3 0.0156 9.0
3.0 1.0 3.0 1.0 9.0 1.0 2.0 7.3 3.3 4.3 6.7 126 0.1250 9.0 9.0 4.0
9.0 3.0 9.0 0.0 9.0 7.0 1.0 3.5 6.5 0.0625 9.0 9.0 2.0 4.0 0.0 9.0
0.0 3.0 6.0 0.5 3.0 4.5 0.0313 9.0 9.0 0.0 4.0 0.0 9.0 0.0 3.0 5.5
0.5 2.5 4.0 0.0156 5.0 5.0 0.0 4.0 0.0 9.0 0.0 0.0 5.0 0.0 2.0 4.0
127 0.1250 9.0 9.0 1.0 9.0 3.0 9.0 3.0 9.0 9.0 2.5 6.0 8.0 0.0625
9.0 9.0 1.0 9.0 2.0 9.0 1.0 7.0 7.5 0.5 3.5 7.0 0.0313 9.0 9.0 0.0
4.0 0.0 9.0 0.0 1.0 5.5 0.5 2.5 4.5 0.0156 9.0 9.0 0.0 4.0 0.0 9.0
0.0 0.0 5.0 0.5 2.5 4.5 128 0.0625 9.0 9.0 7.0 9.0 3.0 9.0 1.0 4.0
6.0 2.5 3.5 6.0 0.0313 9.0 9.0 1.0 9.0 1.0 9.0 2.0 1.0 4.5 2.0 3.0
4.0 0.0156 6.0 7.0 1.0 4.0 1.0 9.0 1.0 1.0 4.5 1.5 2.0 3.5 129
0.0625 9.0 9.0 4.0 9.0 4.0 9.0 3.0 5.0 6.0 3.0 3.5 4.5 0.0313 9.0
9.0 4.0 9.0 4.0 9.0 2.0 3.0 5.0 3.5 3.5 4.5 0.0156 9.0 9.0 3.0 5.0
2.0 9.0 1.0 2.0 5.0 2.5 3.0 4.0 130 0.0625 9.0 9.0 5.0 9.0 5.0 9.0
3.0 7.0 8.0 3.5 4.0 5.0 0.0313 9.0 9.0 4.0 9.0 3.0 9.0 2.0 6.0 7.0
3.0 3.5 4.5 0.0156 9.0 9.0 2.0 7.0 2.0 9.0 2.0 4.0 5.5 3.0 3.5 4.5
131 0.0625 9.0 9.0 3.0 9.0 3.0 9.0 2.0 5.0 5.5 3.0 3.0 4.5 0.0313
9.0 9.0 1.0 5.0 3.0 9.0 2.0 4.0 5.0 2.5 3.0 4.5 0.0156 7.0 7.0 1.0
3.0 1.0 7.0 2.0 3.0 4.5 2.0 3.0 4.5 132 0.0625 9.0 9.0 6.0 9.0 3.0
9.0 2.0 3.0 6.0 3.5 4.0 4.5 0.0313 9.0 9.0 1.0 4.0 2.0 9.0 2.0 4.0
5.0 3.0 3.5 4.0 0.0156 9.0 5.0 1.0 4.0 2.0 6.0 1.0 1.0 5.0 2.0 3.0
3.5 133 0.0625 9.0 9.0 3.0 9.0 3.0 9.0 1.0 2.0 5.0 3.0 3.5 4.0
0.0313 9.0 6.0 1.0 6.0 2.0 9.0 1.0 1.0 5.0 2.5 3.0 4.0 0.0156 9.0
9.0 0.0 9.0 0.0 9.0 1.0 1.0 5.0 2.5 2.5 4.0 134 0.0625 9.0 7.0 0.0
4.0 2.0 9.0 1.0 1.0 5.0 2.0 4.0 4.5 0.0313 7.0 4.0 0.0 3.0 1.0 9.0
2.0 0.0 4.0 1.5 3.5 4.5 0.0156 5.0 3.0 0.0 1.0 0.0 3.0 0.0 0.0 3.5
1.0 2.5 3.5 135 0.0625 9.0 9.0 4.0 9.0 4.0 9.0 2.0 6.0 5.0 2.5 3.0
4.0 0.0313 9.0 9.0 4.0 7.0 3.0 9.0 2.0 4.0 5.0 2.0 2.5 4.0 0.0156
4.0 9.0 2.0 4.0 1.0 9.0 1.0 2.0 5.0 2.0 2.5 3.5 136 0.0625 9.0 9.0
7.0 9.0 3.0 9.0 3.0 6.0 5.5 2.5 3.0 4.0 0.0313 9.0 9.0 4.0 9.0 2.0
9.0 3.0 6.0 5.5 3.0 3.0 4.0 0.0156 9.0 9.0 1.0 9.0 1.0 9.0 2.0 4.0
4.5 2.5 2.5 4.0 137 0.0625 9.0 9.0 4.0 9.0 3.0 9.0 3.0 3.0 5.5 3.5
4.5 4.0 0.0313 9.0 9.0 1.0 9.0 1.0 9.0 1.0 1.0 5.5 3.0 3.0 4.0
0.0156 9.0 9.0 1.0 6.0 1.0 9.0 2.0 1.0 6.0 3.0 3.5 4.0 138 0.0625
9.0 9.0 6.0 9.0 2.0 9.0 2.0 9.0 6.5 3.0 3.0 5.0 0.0313 9.0 9.0 1.0
9.0 2.0 9.0 1.0 4.0 6.0 2.5 3.0 4.5 0.0156 9.0 9.0 0.0 9.0 0.0 9.0
1.0 3.0 5.0 1.5 2.5 4.0 139 0.0625 9.0 7.0 9.0 9.0 4.0 5.0 3.0 5.0
7.0 3.5 3.5 5.0 0.0313 9.0 9.0 5.0 9.0 3.0 9.0 2.0 2.0 6.5 3.0 3.0
4.5 0.0156 9.0 9.0 4.0 9.0 1.0 9.0 3.0 2.0 5.5 2.0 2.5 4.5 140
0.0625 9.0 4.0 0.0 3.0 2.0 9.0 0.0 0.0 5.5 1.5 4.0 4.0 0.0313 4.0
2.0 0.0 0.0 9.0 0.0 0.0 4.5 0.5 3.5 4.0 0.0156 4.0 2.0 0.0 3.0 0.0
9.0 0.0 0.0 3.5 0.5 2.5 3.5 141 0.0625 8.0 9.0 0.0 9.0 2.0 9.0 0.0
0.0 4.5 2.0 4.5 5.0 0.0313 7.0 7.0 0.0 5.0 2.0 9.0 0.0 0.0 4.0 1.5
3.5 4.5 0.0156 7.0 7.0 0.0 3.0 0.0 9.0 0.0 0.0 4.0 0.5 3.0 4.0 142
0.0625 9.0 9.0 3.0 9.0 1.0 9.0 2.0 3.0 5.5 2.0 2.5 4.5 0.0313 9.0
9.0 1.0 9.0 1.0 7.0 1.0 1.0 5.0 1.5 2.5 4.0 0.0156 3.0 9.0 0.0 4.0
0.0 7.0 1.0 2.0 5.0 2.0 2.5 4.0 143 0.0625 9.0 9.0 3.0 6.0 3.0 9.0
1.0 3.0 5.0 2.0 3.5 4.0 0.0313 9.0 9.0 1.0 6.0 1.0 9.0 2.0 1.0 4.5
1.5 2.0 4.0 0.0156 9.0 9.0 0.0 2.0 0.0 9.0 1.0 2.0 4.0 1.5 1.5 4.0
144 0.0625 9.0 9.0 7.0 9.0 4.0 9.0 4.0 6.0 6.5 3.0 4.0 4.5 0.0313
9.0 9.0 5.0 9.0 3.0 9.0 3.0 3.0 5.5 2.5 3.5 4.0 0.0156 9.0 7.0 3.0
7.0 3.0 9.0 2.0 3.0 5.0 2.5 3.5 4.0 145 0.0625 9.0 9.0 5.0 9.0 7.0
9.0 3.0 5.0 5.5 3.5 4.0 5.0 0.0313 9.0 9.0 2.0 9.0 4.0 9.0 3.0 3.0
5.0 2.5 3.0 4.0 0.0156 9.0 9.0 1.0 5.0 1.0 9.0 2.0 1.0 4.5 2.5 3.0
4.0 146 0.0625 9.0 9.0 4.0 9.0 4.0 9.0 2.0 3.0 6.0 4.0 4.5 4.5
0.0313 9.0 9.0 2.0 9.0 2.0 9.0 1.0 2.0 6.0 3.5 3.5 4.5 0.0156 9.0
9.0 1.0 9.0 2.0 9.0 1.0 1.0 5.0 2.0 2.0 4.0 147 0.0625 9.0 7.0 2.0
9.0 3.0 9.0 1.0 2.0 6.0 3.5 4.0 4.5 0.0313 9.0 9.0 1.0 6.0 1.0 9.0
2.0 1.0 5.5 2.5 3.5 4.5 0.0156 9.0 6.0 1.0 5.0 0.0 9.0 1.0 1.0 5.5
1.5 2.5 4.0 148 0.0625 9.0 9.0 3.0 7.0 2.0 9.0 3.0 4.0 6.5 3.0 4.0
5.0 0.0313 9.0 7.0 3.0 7.0 2.0 9.0 3.0 2.0 5.0 3.0 3.0 4.0 0.0156
9.0 9.0 3.0 4.0 2.0 9.0 2.0 2.0 4.5 2.0 2.5 4.0 149 0.0625 9.0 9.0
0.0 4.0 2.0 9.0 0.0 0.0 4.5 1.0 3.5 4.5 0.0313 8.0 9.0 0.0 3.0 0.0
9.0 0.0 0.0 4.5 1.0 3.5 4.5 0.0156 4.0 4.0 0.0 3.0 0.0 9.0 0.0 0.0
4.0 0.5 3.0 4.0 150 0.0625 9.0 9.0 3.0 9.0 4.0 9.0 2.0 5.0 6.0 3.0
3.5 4.0 0.0313 9.0 9.0 3.0 9.0 2.0 9.0 1.0 1.0 5.5 2.5 3.5 4.0
0.0156 9.0 7.0 1.0 9.0 1.0 9.0 2.0 1.0 5.0 2.0 3.5 4.0 151 0.0625
9.0 9.0 4.0 9.0 6.0 9.0 4.0 9.0 5.5 3.5 4.0 5.0 0.0313 9.0 7.0 4.0
7.0 4.0 9.0 3.0 5.0 4.5 2.5 2.5 4.5 0.0156 9.0 7.0 2.0 9.0 4.0 9.0
3.0 5.0 4.0 2.0 2.5 4.0 152 0.0625 9.0 9.0 3.0 9.0 2.0 9.0 2.0 3.0
6.0 3.0 4.0 6.5 0.0313 4.0 4.0 0.0 4.0 0.0 9.0 2.0 3.0 4.5 2.0 3.5
5.0 0.0156 6.0 2.0 0.0 0.0 0.0 7.0 1.0 0.0 4.0 1.5 3.0 4.0 153
0.0625 5.0 1.0 1.0 1.0 0.0 9.0 1.0 0.0 4.0 1.5 3.0 4.5 0.0313 1.0
1.0 0.0 1.0 0.0 6.0 0.0 0.0 4.0 1.5 2.0 3.5 0.0156 1.0 0.0 0.0 0.0
0.0 4.0 0.0 0.0 3.5 1.5 2.0 3.0 154 0.0625 9.0 9.0 1.0 9.0 4.0 9.0
0.0 5.0 7.5 2.0 4.0 5.0 0.0313 9.0 9.0 0.0 9.0 3.0 9.0 0.0 0.0 6.0
1.5 3.5 4.0 0.0156 9.0 3.0 0.0 9.0 3.0 9.0 0.0 0.0 5.5 0.5 3.5 4.0
155 0.0625 9.0 0.0 0.0 0.0 0.0 9.0 0.0 0.0 5.0 0.0 3.0 4.0 0.0313
9.0 0.0 0.0 0.0 0.0 4.0 0.0 0.0 5.0 0.0 2.0 4.0 0.0156 3.0 0.0 0.0
0.0 0.0 2.0 0.0 0.0 4.0 0.0 1.0 4.0 156 0.0625 9.0 9.0 1.0 9.0 3.0
9.0 0.0 5.0 5.5 2.0 4.0 4.5 0.0313 9.0 7.0 0.0 9.0 0.0 9.0 0.0 0.0
4.0 0.5 3.5 4.5 0.0156 9.0 7.0 0.0 9.0 0.0 9.0 0.0 0.0 5.5 0.5 3.0
4.5 157 0.0625 9.0 5.0 3.0 9.0 2.0 6.0 2.0 7.0 7.5 3.0 4.0 7.0
0.0313 9.0 2.0 0.0 4.0 0.0 7.0 1.0 1.0 5.0 2.5 3.5 7.0 0.0156 7.0
2.0 0.0 2.0 0.0 3.0 0.0 0.0 4.5 2.0 2.5 7.0 158 0.0625 9.0 9.0 9.0
9.0 3.0 9.0 3.0 9.0 7.0 3.5 3.5 5.5 0.0313 9.0 7.0 4.0 7.0 2.0 9.0
2.0 3.0 5.0 2.5 4.0 4.5 0.0156 9.0 6.0 4.0 6.0 0.0 9.0 2.0 2.0 5.0
2.0 3.5 4.0 159 0.0625 9.0 7.0 7.0 5.0 4.0 9.0 3.0 7.0 7.0 2.0 3.5
7.0 0.0313 9.0 7.0 1.0 4.0 1.0 9.0 3.0 2.0 5.5 2.0 3.5 6.5 0.0156
9.0 4.0 0.0 3.0 0.0 9.0 2.0 1.0 5.0 1.5 2.5 5.0 160 0.1250 9.0 9.0
4.0 9.0 4.0 9.0 7.0 9.0 7.0 4.5 6.0 7.5 0.0625 9.0 9.0 1.0 9.0 2.0
9.0 4.0 9.0 7.0 4.5 5.0 7.0 0.0313 9.0 7.0 0.0 6.0 0.0 9.0 5.0 6.0
6.0 3.5 4.0 7.0 0.0156 9.0 7.0 0.0 2.0 0.0 9.0 3.0 0.0 5.0 2.0 3.0
6.5 161 0.1250 9.0 9.0 3.0 9.0 4.0 9.0 4.0 7.0 8.5 3.5 4.5 7.5
0.0625 7.0 9.0 1.0 7.0 2.0 9.0 4.0 7.0 7.0 3.5 4.0 7.0 0.0313 5.0
4.0 1.0 5.0 1.0 3.0 0.0 1.0 6.5 3.0 3.5 6.5 0.0156 0.0 1.0 0.0 1.0
0.0 1.0 0.0 0.0 5.0 2.5 2.5 4.5 162 0.0625 9.0 9.0 2.0 9.0 6.0 9.0
0.0 4.0 8.5 1.5 3.5 5.5 0.0313 9.0 9.0 0.0 9.0 3.0 9.0 0.0 3.0 6.5
1.5 3.5 5.0 0.0156 9.0 9.0 0.0 9.0 0.0 9.0 0.0 0.0 6.0 0.5 3.5 4.5
163 0.0625 9.0 9.0 3.0 9.0 5.0 9.0 1.0 3.0 8.0 2.0 4.5 5.5 0.0313
9.0 9.0 0.0 9.0 3.0 9.0 0.0 7.0 1.5 4.0 5.5 0.0156 9.0 9.0 0.0 9.0
0.0 9.0 0.0 0.0 6.0 1.0 3.5 5.0 164 0.1250 9.0 9.0 6.0 9.0 6.0 9.0
3.0 6.0 7.5 5.0 5.5 6.5 0.0625 9.0 9.0 5.0 9.0 7.0 9.0 3.0 9.0 7.0
5.0 5.5 5.5 0.0313 9.0 9.0 2.0 9.0 4.0 9.0 3.0 7.0 6.0 4.0 4.5 5.0
0.0156 9.0 7.0 2.0 9.0 3.0 9.0 2.0 4.0 6.0 2.5 4.0 5.0 165 0.1250
9.0 9.0 3.0 9.0 5.0
9.0 5.0 7.0 7.0 4.0 5.0 5.5 0.0625 9.0 7.0 3.0 7.0 4.0 9.0 3.0 9.0
6.5 3.0 4.0 5.0 0.0313 9.0 6.0 2.0 6.0 1.0 9.0 4.0 6.0 5.0 1.5 3.0
5.0 0.0156 9.0 2.0 0.0 5.0 0.0 9.0 2.0 2.0 5.0 2.0 3.0 40 166
0.1250 9.0 7.0 1.0 7.0 2.0 7.0 2.0 2.0 5.0 2.0 3.0 4.5 0.0625 3.0
6.0 0.0 4.0 0.0 2.0 1.0 1.0 4.0 1.5 2.5 3.5 0.0313 1.0 3.0 0.0 1.0
0.0 2.0 0.0 0.0 3.5 0.5 1.5 3.0 0.0156 2.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 4.0 1.0 1.5 3.0 167 0.1250 9.0 7.0 4.0 9.0 4.0 9.0 3.0 9.0 6.5
4.0 4.5 5.5 0.0625 9.0 9.0 1.0 9.0 4.0 9.0 3.0 9.0 6.5 3.5 4.0 5.5
0.0313 9.0 7.0 2.0 7.0 3.0 9.0 3.0 4.0 6.0 3.5 4.0 5.5 0.0156 9.0
4.0 1.0 4.0 2.0 9.0 3.0 2.0 5.0 3.0 4.0 4.5 168 0.0625 9.0 9.0 2.0
4.0 3.0 9.0 4.0 3.0 7.0 2.5 4.0 7.0 0.0313 9.0 9.0 0.0 3.0 1.0 9.0
0.0 0.0 6.5 1.5 3.5 4.5 0.0156 9.0 3.0 0.0 2.0 0.0 5.0 0.0 0.0 5.5
1.0 3.5 4.5 169 0.0625 9.0 9.0 3.0 4.0 0.0 9.0 7.0 9.0 7.5 2.0 7.0
8.5 0.0313 9.0 9.0 1.0 3.0 0.0 9.0 4.0 5.0 6.5 1.0 6.0 7.5 0.0156
9.0 9.0 0.0 0.0 0.0 9.0 2.0 0.0 5.0 0.5 4.5 6.0 170 0.0625 9.0 9.0
1.0 9.0 4.0 9.0 1.0 9.0 7.5 2.5 5.0 6.0 0.0313 9.0 9.0 0.0 9.0 3.0
9.0 1.0 9.0 7.5 2.0 4.0 6.0 0.0156 9.0 9.0 0.0 4.0 0.0 9.0 1.0 6.0
7.5 2.0 3.5 5.0 171 0.0625 9.0 9.0 4.0 9.0 7.0 9.0 3.0 9.0 7.0 5.0
6.0 7.0 0.0313 9.0 9.0 3.0 9.0 6.0 9.0 4.0 7.0 6.5 4.0 5.0 6.5
0.0156 9.0 6.0 2.0 7.0 3.0 9.0 4.0 7.0 5.5 3.5 4.0 5.0 172 0.0625
9.0 9.0 2.0 9.0 7.0 9.0 3.0 2.0 7.0 4.0 4.0 5.0 0.0313 9.0 9.0 2.0
9.0 4.0 9.0 3.0 3.0 6.5 3.5 4.5 5.0 0.0156 9.0 6.0 1.0 6.0 3.0 9.0
2.0 2.0 6.0 3.5 4.0 5.0
EXAMPLE 38
Preemergence Herbicidal Evaluation of Test Compounds
[0718] The preemergence herbicidal activity of the test compounds
of the present invention is exemplified by the following tests in
which the seeds of a variety of monocotyledonous and dicotyledonous
plants are separately mixed with potting soil and planted on top of
approximately one inch of soil in separate pint cups. After
planting, the cups are sprayed with the selected aqueous acetone
solution containing test compound in sufficient quantity to provide
the equivalent of about 0.0156 to 0.500 kg per hectare of test
compound per cup. The treated cups are then placed on greenhouse
benches, watered and cared for in accordance with conventional
greenhouse procedures. From four to five weeks after treatment, the
tests are terminated and each cup is examined and rated according
to the rating system provided in Example 37.
[0719] The data obtained are reported in Table II below. The
compounds evaluated are reported by compound number given in
Example 37.
20TABLE II Preemergence Herbicidal Evaluations of Test Compounds G
O T A A C C G I I E S L G R R Z B M A H A P P C E X L Y Z E U B S E
L O O H T M X S A A Compound Rate T E O A A H S C V A M A W M
Number (kg/ha) H L B L P E S G I W A T R X 1 0.5000 9.0 6.7 6.7 9.0
8.0 8.0 7.7 8.0 3.0 6.0 6.0 2.0 0.2500 9.0 5.0 6.0 9.0 9.0 6.0 5.0
9.0 4.0 3.0 6.0 0.0 0.1250 9.0 5.0 2.0 9.0 9.0 7.0 6.0 8.0 2.0 2.0
3.0 0.0 0.0625 9.0 2.0 3.0 9.0 7.0 6.0 5.0 9.0 2.0 0.0 4.0 0.0
0.0313 5.0 0.0 0.0 9.0 9.0 1.0 2.0 5.0 0.0 0.0 2.0 0.0 2 0.5000 4.0
0.0 2.0 9.0 0.0 8.0 9.0 1.0 3.0 0.0 0.0 0.2500 0.0 9.0 0.0 0.0 6.0
0.0 2.0 0.0 0.0 0.1250 0.0 0.0 4.0 6.0 0.0 2.0 0.0 0.0 0.0625 0.0
0.0 2.0 0.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0313 0.0 0.0 2.0 7.0 0.0 0.0
0.0 0.0 2.0 0.0 0.0 3 0.5000 6.0 7.0 2.0 9.0 4.0 6.0 9.0 2.0 1.0
2.0 4.0 0.2500 0.0 2.0 0.0 9.0 2.0 4.0 4.0 0.0 0.0 2.0 2.0 0.1250
2.0 2.0 0.0 9.0 0.0 2.0 4.0 0.0 0.0 0.0 1.0 0.0625 2.0 0.0 0.0 9.0
0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 6.0 4.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 4 0.5000 8.0 4.0 7.0 9.0 9.0 6.0 9.0 4.0 4.0 3.0 4.0
0.2500 2.0 1.0 2.0 2.0 2.0 2.0 4.0 2.0 2.0 3.0 2.0 0.1250 0.0 0.0
0.0 0.0 0.0 0.0 2.0 0.0 0.0 2.0 2.0 5 0.5000 0.0 0.0 0.0 9.0 0.0
7.0 9.0 2.0 2.0 2.0 2.0 0.2500 0.0 0.0 0.0 9.0 0.0 6.0 6.0 2.0 2.0
1.0 2.0 0.1250 0.0 0.0 0.0 5.0 0.0 2.0 2.0 1.0 0.0 0.0 1.0 0.0625
0.0 0.0 0.0 4.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 6 0.5000 0.0 0.0 0.0
9.0 0.0 2.0 0.0 0.0 0.0 0.0 0.2500 0.0 0.0 0.0 4.0 0.0 0.0 2.0 0.0
0.0 0.0 0.0 0.1250 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 7
0.2500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.5 9.0 8.5 9.0 0.1250
9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 8.5 8.5 8.5 0.0625 9.0 9.0
9.0 9.0 9.0 4.0 9.0 9.0 9.0 7.5 8.0 7.5 8.5 0.0313 9.0 8.5 9.0 9.0
7.5 4.0 9.0 9.0 9.0 6.5 7.5 6.5 8.0 0.0157 9.0 5.0 9.0 9.0 4.0 9.0
5.0 9.0 5.0 5.0 5.0 7.0 8 0.5000 9.0 9.0 3.8 9.0 9.0 9.0 9.0 9.0
8.8 8.5 7.8 8.3 0.2500 9.0 8.9 3.3 9.0 9.0 8.6 8.9 9.0 7.9 7.1 7.2
7.9 0.1250 9.0 8.5 1.7 9.0 7.5 8.6 7.4 9.0 5.9 5.4 5.5 7.4 0.0625
8.7 5.7 1.2 9.0 5.5 6.4 4.4 8.2 3.2 2.8 2.8 6.4 0.0313 8.4 4.5 0.1
9.0 1.3 4.4 2.2 6.1 1.1 0.8 0.8 4.9 0.0156 7.3 1.6 0.0 9.0 0.0 1.1
0.4 2.8 0.2 0.6 0.2 2.2 9 0.2500 9.0 9.0 8.0 9.0 9.0 9.0 9.0 9.0
9.0 9.0 9.0 8.7 0.1250 9.0 9.0 5.3 9.0 9.0 9.0 9.0 9.0 8.7 9.0 9.0
8.7 0.0625 9.0 7.3 3.0 9.0 9.0 7.0 8.7 9.0 6.3 7.5 7.5 8.3 0.0313
9.0 6.3 1.0 9.0 4.5 7.7 8.3 9.0 6.0 8.5 7.0 7.0 0.0156 9.0 3.0 1.0
9.0 1.0 5.0 5.7 8.3 4.0 5.5 4.0 6.7 10 0.2500 9.0 6.3 3.3 9.0 9.0
9.0 9.0 9.0 7.0 7.5 7.5 8.0 0.1250 9.0 4.7 1.3 9.0 9.0 8.3 9.0 9.0
6.7 6.5 6.5 7.3 0.0625 9.0 3.3 0.7 9.0 4.5 5.3 7.0 9.0 3.7 4.5 5.5
7.0 0.0313 8.0 0.3 0.7 9.0 2.0 3.0 4.0 5.7 2.3 3.0 3.5 6.7 0.0156
5.5 0.3 0.0 9.0 0.5 2.0 2.0 2.3 2.0 1.0 1.0 4.7 11 0.2500 9.0 9.0
5.5 9.0 9.0 9.0 7.0 9.0 8.0 4.0 5.0 5.5 0.1250 9.0 6.5 0.0 9.0 0.0
9.0 3.5 7.5 6.0 2.0 2.0 4.5 0.0625 8.5 5.5 0.0 9.0 0.0 8.0 0.0 7.0
3.5 0.0 0.0 3.5 0.0313 8.5 1.0 0.0 9.0 0.0 8.0 0.0 1.0 1.5 0.0 0.0
0.5 0.0156 7.5 0.0 0.0 7.5 0.0 2.0 0.0 0.0 1.5 0.0 0.0 0.0 12
0.2500 9.0 9.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 8.5 0.1250 9.0
9.0 4.5 9.0 9.0 9.0 9.0 9.0 6.5 7.0 8.0 6.5 0.0625 9.0 9.0 4.5 9.0
9.0 9.0 6.0 9.0 3.5 4.0 5.0 5.5 0.0313 9.0 4.5 0.0 9.0 0.0 9.0 5.0
9.0 2.0 1.0 1.0 5.0 0.0156 7.5 0.0 0.0 9.0 0.0 4.5 2.0 8.5 1.5 0.0
0.0 4.0 13 0.2500 9.0 9.0 3.0 9.0 0.0 9.0 8.0 9.0 4.0 4.0 6.0 7.0
0.1250 9.0 9.0 1.0 9.0 0.0 8.0 7.0 9.0 2.0 3.0 4.0 5.0 0.0625 9.0
6.0 0.0 9.0 0.0 9.0 1.0 9.0 1.0 0.0 1.0 4.0 0.0313 9.0 2.0 0.0 9.0
0.0 3.5 0.0 4.5 0.0 0.0 1.0 2.0 0.0156 6.0 0.0 0.0 9.0 0.0 2.5 0.0
2.5 0.0 0.0 0.0 14 0.5000 9.0 9.0 5.0 9.0 9.0 6.0 9.0 6.0 3.0 3.0
0.2500 9.0 9.0 2.0 9.0 9.0 9.0 3.0 9.0 3.0 1.0 0.0 2.0 0.1250 9.0
6.5 1.5 9.0 9.0 7.5 1.0 6.5 2.0 0.5 0.0 1.5 0.0625 2.0 1.0 1.0 9.0
0.0 1.5 0.0 0.5 0.0 0.0 0.0 0.0 0.0313 1.0 0.0 0.0 9.0 0.0 0.0 0.0
0.5 0.0 0.0 0.0 0.0 15 0.2500 9.0 9.0 6.5 9.0 9.0 9.0 4.5 9.0 5.5
1.5 5.0 5.0 0.1250 9.0 3.0 2.0 9.0 9.0 7.0 2.0 4.0 2.5 1.0 5.0 3.0
0.0625 9.0 1.5 0.5 9.0 9.0 1.5 1.0 0.5 1.0 0.5 0.0 2.5 0.0313 3.0
1.0 0.5 9.0 0.0 1.5 0.5 0.5 0.5 0.0 0.0 1.0 0.0156 1.5 0.5 0.0 6.5
0.0 1.0 0.0 0.5 0.5 0.0 0.0 1.0 16 0.5000 9.0 9.0 9.0 9.0 9.0 9.0
7.1 8.9 9.0 7.0 6.4 5.8 6.0 0.2500 9.0 8.9 8.3 9.0 8.2 9.0 4.4 8.5
7.7 3.5 4.3 2.6 3.7 0.1250 8.9 8.5 5.3 9.0 6.4 8.7 1.8 7.5 4.5 2.0
2.2 0.8 1.8 0.0625 8.8 7.8 2.7 8.8 4.8 7.6 0.6 3.7 1.5 2.0 1.0 0.5
1.4 0.0313 8.1 4.5 0.6 8.4 2.0 3.5 0.3 1.0 0.7 0.0 0.3 0.5 0.6
0.0156 5.6 2.3 0.3 5.7 1.2 0.9 0.0 0.2 0.5 0.0 0.1 0.1 0.1 17
0.5000 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 6.5 6.5 7.0 5.5 0.2500 9.0
6.7 3.7 9.0 9.0 9.0 4.3 9.0 3.3 3.3 7.0 3.3 0.1250 9.0 4.3 0.0 9.0
1.0 5.7 0.7 6.7 0.3 1.0 2.0 1.0 0.0625 9.0 1.7 0.7 9.0 0.0 4.0 1.0
2.3 0.3 1.0 0.0 1.0 0.0313 4.0 0.7 0.7 6.0 0.0 0.7 0.7 1.3 0.0 0.0
0.0 0.3 0.0156 0.0 0.0 0.0 4.5 0.0 0.5 0.5 0.5 0.0 0.0 0.0 0.0 18
0.2500 9.0 4.0 0.0 9.0 9.0 1.0 0.0 2.0 3.0 0.0 0.0 0.0 0.1250 2.0
1.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 19 0.2500 9.0 1.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.1250 9.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 20 0.2500 9.0 3.0 9.0 9.0 0.0 2.0 0.0 7.0
4.0 0.0 0.0 0.0 0.1250 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 21
0.2500 2.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 22 0.2500
9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 0.1250 9.0 9.0 3.0
9.0 0.0 9.0 3.0 9.0 7.0 5.0 5.0 8.0 0.0625 9.0 7.0 0.0 9.0 0.0 9.0
0.0 9.0 3.0 0.0 1.0 7.0 0.0313 9.0 5.0 0.0 9.0 0.0 2.0 0.0 7.0 0.0
0.0 0.0 5.0 0.0156 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0
23 0.2500 9.0 7.0 5.0 9.0 2.0 9.0 6.0 6.0 7.0 7.0 7.0 7.0 0.1250
9.0 6.0 2.0 9.0 0.0 5.0 4.0 5.0 6.0 1.0 5.0 5.0 0.0625 9.0 3.0 1.0
7.0 1.0 1.0 2.0 5.0 2.0 1.0 1.0 2.0 0.0313 1.0 0.0 0.0 1.0 1.0 0.0
1.0 1.0 0.0 0.0 0.0 1.0 0.0156 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0
0.0 0.0 0.0 24 0.2500 9.0 2.0 0.0 9.0 4.0 0.0 0.0 1.0 0.0 0.0 0.0
1.0 0.1250 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625
4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 25 0.2500 9.0 9.0
3.0 9.0 0.0 5.0 7.0 9.0 6.0 5.0 6.0 9.0 0.1250 9.0 9.0 2.0 9.0 0.0
2.0 0.0 9.0 3.0 2.0 3.0 8.0 0.0625 9.0 9.0 0.0 9.0 0.0 0.0 0.0 7.0
2.0 0.0 2.0 6.0 0.0313 9.0 2.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0
0.0 0.0156 9.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 26
0.2500 9.0 5.0 0.0 9.0 9.0 3.0 2.0 9.0 1.0 0.0 1.0 5.0 0.1250 6.0
5.0 0.0 9.0 9.0 2.0 1.0 5.0 0.0 0.0 0.0 4.0 0.0625 0.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 2.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 27 0.2500 9.0 7.0 0.0 9.0 9.0 9.0 9.0 9.0 7.0 8.0 9.0 9.0
0.1250 9.0 9.0 0.0 9.0 9.0 9.0 9.0 9.0 9.0 3.0 7.0 9.0 0.0625 9.0
2.0 0.0 9.0 9.0 8.0 9.0 9.0 9.0 3.0 3.0 8.0 0.0313 9.0 2.0 0.0 9.0
9.0 0.0 8.0 9.0 0.0 0.0 7.0 0.0156 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 28 0.2500 9.0 7.0 0.0 9.0 9.0 9.0 9.0 9.0 9.0 8.0
8.0 8.0 0.1250 3.0 0.0 0.0 9.0 0.0 2.0 9.0 9.0 5.0 2.0 9.0 0.0625
0.0 0.0 0.0 0.0 0.0 0.0 7.0 3.0 0.0 0.0 5.0 29 0.2500 9.0 0.0 0.0
0.0 0.0 4.0 0.0 9.0 2.0 3.0 4.0 6.0 0.1250 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 30 0.2500 9.0 6.0 1.0 9.0 9.0 2.0 0.0 9.0 4.0 4.0 6.0
6.0 0.1250 9.0 5.0 1.0 9.0 1.0 1.0 0.0 7.0 1.0 1.0 2.0 3.0 0.0625
9.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 1.0 1.0 3.0 0.0313 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 2.0 1.0 0.0 1.0 31 0.2500 9.0 9.0 1.0 9.0 6.0
9.0 9.0 9.0 6.0 6.0 7.0 9.0 0.1250 9.0 4.0 2.0 9.0 5.0 9.0 9.0 5.0
2.0 3.0 7.0 0.0625 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 3.0 0.0 0.0 3.0
32 0.5000 9.0 9.0 0.0 9.0 7.0 1.0 1.0 9.0 3.0 4.0 3.0 6.0 0.2500
9.0 5.5 0.0 9.0 3.5 0.0 0.0 9.0 1.0 1.5 1.0 4.5 0.1250 9.0 0.5 0.0
9.0 0.5 0.5 0.5 3.5 0.5 0.0 0.0 0.5 0.0625 1.5 0.5 0.0 9.0 0.0 0.5
0.0 0.5 0.5 0.0 0.0 0.0 0.0313 2.5 0.5 0.0 4.5 0.0 0.0 0.0 0.0 0.5
0.0 0.0 0.0 0.0156 0.0 0.0 0.5 4.5 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
33 0.2500 9.0 9.0 9.0 9.0 9.0 0.0 9.0 0.0 0.0 0.0 0.0 0.1250 9.0
9.0 4.0 9.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0625 9.0 9.0 0.0 7.0 0.0
0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0156 0.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
34 0.2500 9.0 7.0 0.0 9.0 9.0 9.0 5.0 9.0 0.0 5.0 5.0 9.0 0.1250
9.0 4.0 0.0 9.0 7.0 3.0 2.0 9.0 0.0 2.0 1.0 7.0 0.0625 9.0 4.0 0.0
9.0 7.0 3.0 0.0 9.0 0.0 0.0 0.0 3.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0
0.0 3.0 0.0 0.0 0.0 0.0 35 0.2500 9.0 9.0 3.0 9.0 9.0 9.0 0.0 9.0
2.0 0.0 3.0 0.0 0.1250 9.0 3.0 0.0 9.0 0.0 3.0 0.0 0.0 0.0 0.0 1.0
0.0 0.0625 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 36
0.2500 9.0 9.0 0.0 9.0 9.0 0.0 6.0 9.0 0.0 4.0 0.0 6.0 0.1250 9.0
0.0 9.0 9.0 0.0 2.0 9.0 0.0 0.0 1.0 3.0 0.0625 9.0 0.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 37 0.2500 3.0 0.0 0.0 9.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.1250 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 38 0.2500 9.0 5.0 3.0 9.0 9.0 9.0 1.0 9.0 6.0 2.0 7.0 4.0
0.1250 9.0 0.0 0.0 9.0 8.0 5.0 0.0 7.0 2.0 0.0 2.0 0.0 0.0625 9.0
0.0 0.0 9.0 5.0 4.0 0.0 3.0 2.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 39 0.2500 9.0 7.0 1.0 9.0 9.0 9.0
0.0 2.0 7.0 2.0 2.0 5.0 0.1250 9.0 6.0 2.0 7.0 6.0 1.0 0.0 0.0 5.0
1.0 1.0 2.0 0.0625 1.0 0.0 0.0 7.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0
0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 40 0.2500 9.0 6.0 1.0 9.0
0.0 9.0 1.0 6.0 3.0 1.0 1.0 1.0 0.1250 9.0 6.0 0.0 9.0 0.0 9.0 1.0
6.0 1.0 0.0 0.0 0.0 0.0625 6.0 2.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 41
0.2500 9.0 8.0 9.0 9.0 0.0 9.0 2.0 9.0 6.0 0.0 0.0 2.0 0.1250 9.0
9.0 9.0 9.0 0.0 9.0 0.0 1.0 2.0 0.0 0.0 0.0 0.0625 9.0 2.0 0.0 9.0
0.0 7.0 0.0 1.0 3.0 0.0 0.0 1.0 0.0313 9.0 1.0 0.0 4.0 0.0 0.0 0.0
1.0 0.0 0.0 0.0 0.0156 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 42 0.2500 9.0 6.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0
0.1250 9.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0625 1.0
0.0 1.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 1.0 0.0313 1.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 43 0.2500 9.0 4.0 9.0 9.0 9.0 9.0
5.0 9.0 2.0 0.0 4.0 6.0 0.1250 9.0 3.0 8.0 9.0 9.0 2.0 0.0 5.0 0.0
0.0 1.0 3.0 0.0625 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 9.0
0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 44 0.5000 9.0 4.0 1.0
9.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.2500 9.0 2.0 0.0 9.0 9.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.1250 9.0 0.0 1.0 9.0 9.0 1.0 0.0 0.0 0.0
0.0 0.0 1.0 0.0625 0.0 0.0 0.0 4.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 0.0 5.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0
0.0 0.0 3.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 45 0.2500 9.0 2.0 0.0
9.0 7.0 1.0 0.0 0.0 3.0 0.0 5.0 4.0 0.1250 9.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 2.0 2.0 0.0625 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 46 0.2500
9.0 1.0 0.0 9.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 0.1250 9.0 1.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 47 0.2500 9.0 0.0 0.0 9.0 9.0
9.0 0.0 4.0 0.0 0.0 0.0 2.0 0.1250 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0313 4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156
4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 48 0.2500 9.0 4.0
3.0 9.0 0.0 0.0 0.0 0.0 2.0 3.0 2.0 2.0 0.1250 9.0 0.0 0.0 9.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0625 4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 49 0.2500
9.0 9.0 9.0 9.0 9.0 9.0 3.0 5.0 2.0 5.0 2.0 3.0 0.1250 9.0 9.0 3.0
9.0 7.0 9.0 0.0 2.0 5.0 0.0 3.0 0.0625 9.0 9.0 9.0 7.0 2.0 0.0 5.0
2.0 0.0 0.0 0.0 0.0313 9.0 0.0 3.0 9.0 0.0 0.0 0.0 4.0 0.0 0.0 0.0
0.0 0.0156 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 50
0.2500 9.0 0.0 9.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.1250 9.0
0.0 9.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 51 0.2500 9.0 9.0 1.0 9.0 9.0 9.0
1.0 9.0 7.0 7.0 6.0 6.0 0.1250 7.0 9.0 1.0 9.0 7.0 9.0 1.0 6.0 1.0
1.0 2.0 2.0 0.0625 9.0 4.0 0.0 9.0 5.0 9.0 1.0 3.0 1.0 1.0 0.0 1.0
0.0313 9.0 0.0 0.0 9.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 1.0 0.0156 9.0
0.0 0.0 3.0 0.0 2.0 0.0 1.0 0.0 0.0 0.0 1.0 52 0.2500 9.0 3.0 1.0
9.0 7.0 9.0 1.0 9.0 2.0 4.0 5.0 3.0 0.1250 9.0 2.0 1.0 9.0 0.0 2.0
0.0 1.0 1.0 0.0 2.0 1.0 0.0625 9.0 0.0 0.0 6.0 0.0 1.0 0.0 0.0 1.0
0.0 0.0 0.0 0.0313 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
53 0.2500 9.0 9.0 1.0 9.0 7.0 9.0 9.0 9.0 4.0 7.0 7.0 6.0 0.1250
9.0 9.0 1.0 9.0 0.0 9.0 7.0 7.0 2.0 5.0 2.0 5.0 0.0625 9.0 9.0 0.0
9.0 0.0 9.0 4.0 4.0 0.0 1.0 1.0 1.0 0.0313 7.0 0.0 0.0 9.0 0.0 0.0
1.0 1.0 0.0 0.0 0.0 1.0 54 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
6.0 3.0 0.2500 9.0 9.0 6.0 9.0 9.0 9.0 5.0 9.0 7.5 4.5 3.0 4.0
0.1250 9.0 9.0 4.5 9.0 9.0 7.5 2.0 7.0 3.0 2.0 1.0 2.0 0.0625 9.0
8.0 0.0 9.0 0.0 9.0 0.0 3.5 1.5 1.0 0.0 1.0 0.0313 7.5 0.5 0.0 9.0
0.0 6.0 0.0 2.0 0.5 0.0 0.0 1.0 0.0156 4.5 0.0 0.0 4.5 0.0 1.5 0.0
1.0 0.0 0.0 0.0 0.0 59 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0
6.0 0.2500 9.0 9.0 7.5 9.0 9.0 9.0 6.0 9.0 7.0 3.5 2.0 3.5 0.1250
9.0 9.0 7.0 9.0 7.0 9.0 2.0 8.0 4.0 2.5 2.0 3.0 0.0625 8.5 6.5 2.0
9.0 6.0 8.5 0.5 1.5 1.0 0.5 0.0 1.5 0.0313 6.0 3.5 0.0 9.0 0.0 4.0
0.0 0.0 0.5 0.0 0.0 0.5 0.0156 2.0 2.0 0.0 9.0 0.0 1.0 0.0 0.0 1.0
0.0 0.0 1.0 60 0.5000 9.0 9.0 4.0 9.0 9.0 2.0 8.0 6.0 7.0 8.0
0.2500 9.0 7.0 5.5 9.0 0.0 5.0 0.5 4.5 3.5 2.0 1.0 3.0 0.1250 9.0
7.0 1.0 9.0 0.0 2.0 0.0 4.5 3.0 0.5 1.0 1.5 0.0625 7.0 2.0 0.0 9.0
0.0 0.0 0.0 0.5 1.5 0.0 0.0 0.5 0.0313 9.0 0.0 0.0 8.0 0.0 0.0 0.0
0.5 0.5 0.0 0.0 0.0 0.0156 2.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 0.0
0.0 0.0 61 0.2500 1.0 0.0 1.0 9.0 0.0 0.0 0.0 1.0 1.0 1.0 1.0 1.0
0.1250 0.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 62 0.2500
9.0 7.0 1.0 9.0 9.0 9.0 7.0 9.0 7.0 6.0 2.0 7.0 0.1250 9.0 9.0 1.0
9.0 6.0 7.0 3.0 9.0 2.0 4.0 1.0 3.0 0.0625 9.0 7.0 1.0 9.0 0.0 5.0
1.0 6.0 1.0 1.0 1.0 1.0 0.0313 7.0 5.0 0.0 9.0 0.0 3.0 0.0 0.0 0.0
0.0 1.0 0.0156 4.0 2.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 63
0.2500 9.0 9.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 7.0 7.0 7.0 0.1250 9.0
9.0 2.0 9.0 9.0 7.0 4.0 9.0 6.0 7.0 6.0 6.0 0.0625 9.0 6.0 2.0 9.0
0.0 6.0 1.0 1.0 4.0 5.0 1.0 2.0 0.0313 6.0 0.0 2.0 7.0 0.0 1.0 0.0
0.0 1.0 0.0 0.0 1.0 0.0156 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 64 0.2500 9.0 9.0 4.0 9.0 7.0 9.0 6.0 9.0 5.0 5.0 3.0 7.0
0.1250 9.0 9.0 5.0 9.0 9.0 3.0 7.0 3.0 1.0 1.0 3.0 0.0625 9.0 7.0
1.0 9.0 1.0 9.0 1.0 9.0 2.0 1.0 1.0 1.0 0.0313 9.0 6.0 0.0 9.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 1.0 2.0 0.0 9.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 65 0.2500 9.0 9.0 2.0 9.0 9.0 7.0 5.0 9.0 5.0 6.0
3.0 4.0 0.1250 9.0 9.0 1.0 9.0 1.0 9.0 2.0 7.0 2.0 1.0 1.0 2.0
0.0625 9.0 4.0 1.0 9.0 0.0 1.0 0.0 2.0 1.0 1.0 1.0 1.0 0.0313 9.0
2.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156 2.0 1.0 0.0 9.0
0.0 0.0 0.0 0.0 1.0 0.0 0.0 66 0.5000 9.0 9.0 3.0 9.0 9.0 9.0 9.0
9.0 9.0 8.0 4.0 7.0 0.2500 9.0 9.0 0.5 9.0 8.0 6.0 3.0 7.5 4.5 2.5
1.0 2.5 0.1250 9.0 9.0 0.5 9.0 3.5 3.0 0.5 6.0 0.5 0.5 0.5 1.0
0.0625 9.0 3.0 0.0 9.0 0.0 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.0313 8.0
1.0 0.0 9.0 0.0 0.0 0.0 0.5 0.0 0.0 0.0 0.0 0.0156 5.0 0.5 0.0 4.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.5 67 0.2500 9.0 7.0 2.0 9.0 0.0 6.0
1.0 7.0 2.0 1.0 1.0 1.0 0.1250 7.0 7.0 2.0 9.0 1.0 3.0 1.0 6.0 2.0
1.0 1.0 1.0 0.0625 9.0 3.0 0.0 9.0 0.0 2.0 0.0 0.0 2.0 0.0 0.0
1.0
0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0156 1.0
0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 68 0.2500 9.0 7.0 1.0
9.0 0.0 6.0 1.0 2.0 1.0 1.0 1.0 1.0 0.1250 5.0 1.0 0.0 9.0 0.0 0.0
0.0 0.0 1.0 0.0 0.0 1.0 0.0625 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0313 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0156 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 69 0.2500
9.0 7.0 5.0 9.0 1.0 4.0 3.0 7.0 2.0 1.0 1.0 3.0 0.1250 9.0 9.0 1.0
9.0 1.0 1.0 1.0 4.0 1.0 1.0 1.0 3.0 0.0625 9.0 5.0 0.0 9.0 0.0 2.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 4.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 70
0.2500 9.0 9.0 0.0 9.0 0.0 5.0 1.0 9.0 2.0 3.0 5.0 3.0 0.1250 6.0
3.0 1.0 9.0 0.0 1.0 1.0 9.0 0.0 1.0 1.0 1.0 0.0625 0.0 0.0 9.0 0.0
0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 71 0.2500 9.0 9.0 9.0 9.0 6.0 9.0 4.0 9.0 3.0 3.0 3.0 0.1250
9.0 9.0 7.0 9.0 9.0 9.0 2.0 4.0 3.0 1.0 1.0 3.0 0.0625 9.0 7.0 0.0
9.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0313 9.0 2.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 1.0 1.0 0.0 3.0 0.0 0.0 0.0 0.0 1.0
0.0 0.0 0.0 72 0.2500 9.0 9.0 1.0 9.0 9.0 7.0 3.0 9.0 3.0 1.0 2.0
1.0 0.1250 9.0 9.0 1.0 9.0 0.0 2.0 0.0 9.0 1.0 1.0 1.0 1.0 0.0625
9.0 2.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 9.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 2.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 73 0.2500 9.0 9.0 2.0 9.0 9.0 7.0 4.0 9.0 9.0
4.0 4.0 7.0 0.1250 9.0 9.0 1.0 9.0 4.0 1.0 0.0 9.0 1.0 2.0 3.0 4.0
0.0625 9.0 4.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 2.0 1.0 1.0 0.0313 9.0
0.0 0.0 9.0 0.0 1.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0156 9.0 1.0 9.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 74 0.2500 9.0 9.0 0.0 9.0 9.0 1.0 1.0
9.0 1.0 1.0 1.0 1.0 0.1250 9.0 9.0 0.0 9.0 0.0 0.0 0.0 4.0 1.0 1.0
1.0 1.0 0.0625 9.0 3.0 0.0 9.0 0.0 1.0 1.0 1.0 0.0 1.0 1.0 0.0
0.0313 4.0 1.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0156 0.0 0.0
0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 75 0.2500 9.0 7.0 1.0 9.0
0.0 2.0 2.0 9.0 2.0 2.0 2.0 3.0 0.1250 9.0 6.0 1.0 9.0 0.0 0.0 0.0
9.0 2.0 1.0 1.0 1.0 0.0625 9.0 1.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 76 0.2500
9.0 9.0 1.0 9.0 9.0 9.0 9.0 9.0 9.0 5.0 9.0 7.0 0.1250 9.0 9.0 0.0
9.0 1.0 9.0 7.0 9.0 6.0 4.0 7.0 7.0 0.0625 9.0 7.0 0.0 9.0 0.0 0.0
1.0 7.0 3.0 3.0 3.0 5.0 0.0313 1.0 0.0 0.0 9.0 0.0 0.0 0.0 6.0 0.0
0.0 0.0 1.0 0.0156 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
77 0.2500 9.0 7.0 0.0 9.0 1.0 2.0 0.0 9.0 1.0 0.0 0.0 1.0 0.1250
9.0 2.0 0.0 9.0 1.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0625 9.0 1.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 2.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 1.0 0.0 0.0 2.0 0.0 1.0 0.0 0.0 0.0
0.0 0.0 2.0 78 0.2500 9.0 1.0 1.0 9.0 2.0 3.0 1.0 6.0 1.0 0.0 0.0
1.0 0.1250 2.0 1.0 0.0 9.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625
0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 9.0 0.0 0.0 0.0
0.0 1.0 0.0 0.0 0.0 79 0.2500 9.0 8.0 1.0 9.0 0.0 1.0 0.0 4.0 2.0
1.0 1.0 2.0 0.1250 6.0 1.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 1.0
0.0625 2.0 3.0 0.0 9.0 0.0 0.0 0.0 1.0 1.0 1.0 1.0 1.0 0.0313 0.0
1.0 1.0 9.0 0.0 0.0 0.0 1.0 1.0 0.0 0.0 1.0 80 0.2500 9.0 7.0 9.0
9.0 4.0 9.0 0.0 7.0 1.0 1.0 1.0 3.0 0.1250 9.0 9.0 9.0 9.0 4.0 4.0
1.0 7.0 1.0 1.0 2.0 3.0 0.0625 9.0 2.0 0.0 9.0 0.0 0.0 0.0 1.0 1.0
0.0 0.0 1.0 0.0313 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0156 0.0 1.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 81 0.2500 9.0
9.0 0.0 9.0 1.0 9.0 1.0 3.0 3.0 1.0 1.0 2.0 0.1250 9.0 9.0 0.0 9.0
0.0 1.0 0.0 0.0 1.0 1.0 1.0 2.0 0.0625 9.0 6.0 9.0 0.0 0.0 1.0 2.0
0.0 0.0 2.0 0.0313 9.0 6.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
82 0.2500 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 5.0 0.0 0.0 3.0 0.1250
9.0 9.0 9.0 9.0 9.0 9.0 3.0 9.0 0.0 0.0 0.0 0.0 0.0625 9.0 3.0 3.0
9.0 0.0 4.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0313 9.0 2.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 3.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 83 0.5000 9.0 9.0 3.0 9.0 9.0 9.0 4.0 9.0 7.0 5.0 5.0
7.0 0.2500 9.0 9.0 3.0 9.0 9.0 9.0 0.0 9.0 5.0 0.0 0.0 0.0 0.1250
9.0 9.0 0.0 9.0 0.0 3.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 6.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 84 0.5000 9.0 9.0 9.0 9.0 5.0 9.0 9.0 9.0 7.0 9.0 9.0
9.0 0.2500 9.0 9.0 0.0 9.0 5.0 9.0 2.0 9.0 5.0 3.0 6.0 8.0 0.1250
9.0 9.0 0.0 9.0 0.0 1.0 0.0 3.0 3.0 0.0 4.0 5.0 0.0625 7.0 4.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 2.0 3.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 2.0 0.0 0.0 5.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 85 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 4.0 9.0 9.0 3.0 8.0
9.0 0.2500 9.0 9.0 0.0 9.0 6.0 7.0 0.0 9.0 2.0 2.0 5.0 5.0 0.1250
9.0 7.0 0.0 9.0 4.0 5.0 0.0 0.0 2.0 0.0 3.0 2.0 0.0625 9.0 3.0 0.0
9.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 86 0.5000 9.0 9.0 3.0 9.0 9.0 9.0 4.0 9.0 8.0 6.0 6.0
9.0 0.2500 9.0 9.0 0.0 9.0 9.0 9.0 0.0 9.0 4.0 2.0 2.0 4.0 0.1250
9.0 9.0 0.0 9.0 0.0 9.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0625 9.0 6.0 0.0
9.0 0.0 8.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 4.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0156 9.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 87 0.5000 9.0 9.0 2.0 9.0 7.0 6.0 0.0 9.0 5.0 0.0 1.0
1.0 0.2500 9.0 0.0 0.0 9.0 0.0 5.0 0.0 0.0 4.0 0.0 0.0 0.0 0.1250
3.0 0.0 0.0 4.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 88 0.2500 9.0 9.0
9.0 9.0 9.0 9.0 2.0 9.0 9.0 7.0 9.0 8.0 0.1250 9.0 9.0 3.0 9.0 3.0
9.0 0.0 7.0 4.0 2.0 3.0 6.0 0.0625 9.0 7.0 0.0 9.0 3.0 0.0 0.0 3.0
0.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0156 9.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 89
0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 0.2500 9.0
6.5 6.0 9.0 8.5 9.0 5.5 9.0 8.5 8.0 6.5 7.5 0.1250 9.0 6.5 3.0 9.0
4.5 1.5 2.0 9.0 2.0 4.5 2.0 6.5 0.0625 9.0 2.0 0.0 9.0 0.0 0.5 0.0
1.5 1.0 2.0 0.5 1.0 0.0313 6.5 0.5 0.0 9.0 0.0 0.0 0.0 1.5 0.0 0.5
0.0 0.0 0.0156 1.5 0.0 0.0 8.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 90
0.2500 9.0 9.0 9.0 9.0 7.0 9.0 3.0 9.0 9.0 9.0 7.0 8.0 0.1250 9.0
9.0 9.0 9.0 3.0 9.0 0.0 9.0 7.0 2.0 2.0 7.0 0.0625 9.0 3.0 9.0 9.0
0.0 4.0 0.0 3.0 2.0 0.0 0.0 0.0 0.0313 9.0 0.0 3.0 7.0 0.0 1.0 0.0
0.0 0.0 0.0 0.0 0.0 91 0.2500 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.1250 4.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
92 0.2500 9.0 9.0 3.0 9.0 9.0 9.0 0.0 9.0 5.0 5.0 2.0 6.0 0.1250
9.0 5.0 9.0 9.0 9.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 3.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 93 0.2500 9.0 9.0 9.0 9.0 9.0 9.0 0.0 9.0 8.0 4.0 7.0 6.0
0.1250 9.0 9.0 0.0 9.0 9.0 9.0 0.0 0.0 4.0 2.0 2.0 1.0 0.0625 9.0
0.0 0.0 9.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 5.0 0.0 0.0 3.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 94 0.2500 9.0 9.0 0.0 9.0 9.0 9.0
0.0 9.0 4.0 3.0 0.0 6.0 0.1250 9.0 9.0 0.0 9.0 3.0 9.0 0.0 4.0 0.0
0.0 0.0 0.0 0.0625 9.0 4.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0
0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 95 0.5000 9.0 9.0 9.0
9.0 9.0 9.0 0.0 7.0 3.0 1.0 1.0 5.0 0.2500 9.0 6.0 7.0 9.0 7.0 2.0
0.0 4.0 2.0 1.0 0.0 1.0 0.1250 9.0 4.0 0.0 6.0 6.0 0.0 0.0 0.0 2.0
0.0 0.0 0.0 0.0625 9.0 1.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 96
0.5000 9.0 6.0 9.0 9.0 7.0 9.0 1.0 4.0 4.0 2.0 1.0 4.0 0.2500 9.0
4.0 4.0 9.0 6.0 9.0 1.0 1.0 3.0 1.0 1.0 2.0 0.1250 9.0 1.0 0.0 3.0
2.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 2.0 2.0 0.0 0.0
1.0 0.0 0.0 0.0 1.0 0.0313 1.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 0.0 0.0
0.0 0.0 97 0.5000 9.0 4.0 3.0 9.0 5.0 9.0 0.0 7.0 3.0 1.0 2.0 4.0
0.2500 9.0 4.0 1.0 9.0 0.0 9.0 0.0 1.0 0.0 1.0 1.0 0.0 0.1250 4.0
0.0 0.0 7.0 1.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 98 0.5000 9.0 7.0 7.0
9.0 7.0 9.0 2.0 7.0 5.0 4.0 3.0 6.0 0.2500 6.0 5.0 2.0 9.0 7.0 4.0
1.0 3.0 4.0 1.0 1.0 4.0 0.1250 6.0 3.0 1.0 7.0 3.0 1.0 4.0 1.0 0.0
0.0 0.0 0.0625 2.0 2.0 0.0 5.0 6.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0
0.0313 0.0 0.0 0.0 2.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156 0.0
0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 99 0.5000 9.0 9.0 7.0
9.0 7.0 9.0 7.0 9.0 7.0 4.0 5.0 7.0 0.2500 9.0 9.0 3.0 9.0 9.0 9.0
1.0 7.0 7.0 4.0 4.0 6.0 0.1250 9.0 9.0 2.0 9.0 7.0 9.0 1.0 6.0 4.0
1.0 1.0 2.0 0.0625 9.0 4.0 1.0 9.0 1.0 9.0 0.0 1.0 3.0 1.0 1.0 1.0
0.0313 9.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156 9.0 0.0
0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 100 0.5000 9.0 7.0 8.0 9.0
6.0 5.0 1.0 1.0 2.0 1.0 1.0 1.0 0.2500 9.0 1.0 0.0 9.0 6.0 2.0 1.0
1.0 0.0 0.0 0.0 0.0 0.1250 2.0 1.0 0.0 9.0 0.0 0.0 0.0 1.0 0.0 1.0
0.0 0.0625 0.0 0.0 0.0 9.0 1.0 0.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0313
0.0 0.0 0.0 9.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 102 0.5000 9.0 7.0
4.0 9.0 4.0 9.0 0.0 1.0 4.0 1.0 1.0 1.0 0.2500 6.0 4.0 0.0 1.0 1.0
1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 5.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 6.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0
0.0 0.0156 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 103 0.5000
9.0 9.0 3.0 9.0 7.0 9.0 2.0 9.0 3.0 2.0 1.0 1.0 0.2500 9.0 4.0 3.0
9.0 0.0 5.0 0.0 3.0 0.0 0.0 0.0 0.0 0.1250 9.0 0.0 0.0 9.0 0.0 3.0
0.0 3.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0313 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
104 0.5000 9.0 9.0 0.0 9.0 6.0 9.0 1.0 6.0 3.0 0.0 1.0 2.0 0.2500
9.0 3.0 0.0 9.0 0.0 3.0 1.0 0.0 0.0 0.0 0.0 0.0 0.1250 8.0 0.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 3.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 105 0.5000 9.0 4.0 0.0 9.0 7.0 4.0 1.0 3.0
0.0 0.0 0.0 2.0 0.2500 9.0 3.0 0.0 9.0 3.0 3.0 0.0 3.0 0.0 0.0 0.0
1.0 0.1250 7.0 1.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 106 0.2500
9.0 9.0 6.0 9.0 7.0 9.0 7.0 9.0 5.0 5.0 5.0 5.0 0.1250 9.0 7.0 4.0
9.0 6.0 7.5 2.0 9.0 3.5 2.5 3.0 4.0 0.0625 8.0 5.0 2.0 9.0 3.0 7.0
1.5 4.5 2.0 2.0 2.0 2.5 0.0313 6.5 1.5 1.5 9.0 2.0 2.5 1.0 0.5 1.5
1.0 0.0 1.0 0.0156 5.0 1.5 0.0 8.0 1.0 2.0 0.0 0.0 1.0 1.5 0.0 0.0
107 0.2500 9.0 2.0 1.0 9.0 7.0 7.0 1.0 7.0 3.0 2.0 4.0 4.0 0.1250
9.0 0.0 0.0 9.0 7.0 1.0 0.0 0.0 2.0 0.0 0.0 1.0 0.0625 1.0 0.0 0.0
6.0 1.0 0.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 1.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 108 0.2500 9.0 1.0 9.0 9.0 9.0 9.0 1.0 9.0 2.0
5.0 5.0 2.0 0.1250 8.0 0.0 0.0 9.0 7.0 4.0 0.0 7.0 2.0 1.0 2.0 1.0
0.0625 4.0 0.0 0.0 9.0 6.0 0.0 0.0 1.0 2.0 0.0 0.0 0.0 0.0313 0.0
0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 1.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 109 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
6.0 7.0 0.2500 9.0 9.0 9.0 9.0 4.0 8.0 8.5 9.0 9.0 5.0 4.0 6.5
0.1250 9.0 9.0 6.5 9.0 4.0 8.0 7.0 9.0 7.5 4.0 6.0 6.0 0.0625 9.0
8.0 5.5 9.0 3.0 5.0 4.0 9.0 5.0 2.0 1.0 4.0 0.0313 9.0 3.0 4.0 9.0
3.0 2.0 2.5 6.0 2.0 1.0 1.0 3.5 0.0156 6.5 3.0 6.5 9.0 3.0 2.0 1.5
5.5 1.5 0.0 0.0 3.0 110 0.5000 9.0 9.0 9.0 9.0 9.0 4.0 9.0 7.0 3.0
4.0 0.2500 9.0 6.5 5.0 9.0 2.0 9.0 3.0 9.0 5.5 5.0 1.0 3.5 0.1250
9.0 4.5 2.0 9.0 0.0 9.0 2.0 8.0 4.0 1.5 1.0 2.5 0.0625 9.0 3.5 0.0
9.0 0.0 5.5 0.5 5.0 2.5 0.5 1.0 1.0 0.0313 9.0 2.5 0.0 9.0 0.0 4.5
0.0 2.5 0.5 0.5 1.0 0.5 0.0156 5.5 1.0 0.0 8.0 0.0 3.5 0.0 1.5 0.5
0.0 0.0 0.0 111 0.2500 9.0 7.0 9.0 9.0 7.0 7.0 4.0 7.0 4.0 5.0 4.0
4.0 0.1250 9.0 6.0 1.0 9.0 6.0 9.0 0.0 7.0 3.0 1.0 1.0 4.0 0.0625
2.0 0.0 1.0 9.0 0.0 0.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0156 1.0 0.0 0.0 0.0 0.0 0.0
0.0 1.0 0.0 0.0 0.0 112 0.2500 1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 3.0
2.0 1.0 4.0 0.1250 0.0 0.0 0.0 0.0 0.0 0.0 3.0 0.0 0.0 1.0 0.0625
0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 0.0
0.0 0.0 1.0 0.0 0.0 0.0 0.0 113 0.2500 9.0 2.0 0.0 9.0 3.0 1.0 0.0
1.0 2.0 0.0 0.0 1.0 0.1250 9.0 0.0 0.0 9.0 1.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0625 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 1.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 0.0156 0.0
0.0 0.0 6.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 114 0.2500 9.0 7.0 9.0
9.0 9.0 7.0 4.0 9.0 3.0 2.0 3.0 2.0 0.1250 9.0 5.0 3.0 9.0 7.0 9.0
2.0 7.0 2.0 2.0 1.0 1.0 0.0625 6.0 0.0 1.0 7.0 3.0 0.0 0.0 2.0 0.0
0.0 0.0 1.0 0.0313 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0
0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 115 0.2500
9.0 1.0 2.0 9.0 9.0 7.0 0.0 4.0 4.0 3.0 4.0 2.0 0.1250 9.0 0.0 4.0
9.0 7.0 2.0 0.0 0.0 3.0 1.0 0.0 1.0 0.0625 0.0 0.0 0.0 7.0 3.0 0.0
0.0 0.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 5.0 3.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0156 0.0 0.0 2.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 116
0.2500 9.0 1.0 2.0 9.0 7.0 3.0 0.0 3.0 2.0 1.0 1.0 0.0 0.1250 9.0
2.0 0.0 7.0 0.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0625 4.0 2.0 0.0 4.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 1.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 1.0 0.0
0.0 0.0 117 0.2500 9.0 7.0 1.0 9.0 7.0 9.0 0.0 0.0 1.0 0.0 0.0 0.0
0.1250 1.0 0.0 1.0 6.0 3.0 0.0 0.0 0.0 1.0 0.0 0.0 1.0 0.0625 0.0
0.0 0.0 9.0 0.0 0.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0
1.0 0.0 0.0 0.0 0.0 118 0.2500 7.0 6.0 4.0 9.0 7.0 6.0 0.0 2.0 3.0
0.0 0.0 0.0 0.1250 9.0 0.0 9.0 6.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0625 9.0 0.0 0.0 6.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 119 0.2500
9.0 4.0 3.0 9.0 4.0 9.0 2.0 7.0 2.0 0.0 0.0 1.0 0.1250 9.0 4.0 9.0
0.0 9.0 2.0 7.0 1.0 0.0 0.0 0.0 0.0625 4.0 0.0 0.0 9.0 0.0 0.0 0.0
2.0 0.0 0.0 0.0 0.0 0.0313 3.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 120
0.2500 9.0 4.0 4.0 9.0 0.0 9.0 2.0 9.0 3.0 0.0 4.0 3.0 0.1250 9.0
4.0 4.0 9.0 0.0 4.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0625 9.0 3.0 3.0 9.0
0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 121 0.2500 9.0 8.0 9.0 9.0 9.0 9.0 9.0 9.0 2.0 5.0 8.0 8.0
0.1250 9.0 4.0 9.0 9.0 5.0 4.0 7.0 9.0 1.0 4.0 7.0 7.0 0.0625 9.0
3.0 0.0 9.0 0.0 3.0 4.0 7.0 0.0 0.0 3.0 6.0 0.0313 9.0 2.0 0.0 9.0
0.0 0.0 0.0 3.0 0.0 0.0 2.0 4.0 0.0156 9.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 122 0.5000 9.0 3.0 3.0 9.0 6.0 1.0 1.0 9.0 0.0
1.0 1.0 1.0 0.2500 9.0 2.0 0.0 9.0 4.0 1.0 0.0 1.0 0.0 0.0 0.0 0.0
0.1250 9.0 2.0 0.0 9.0 4.0 2.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0625 4.0
0.0 0.0 7.0 3.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0
2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 3.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 123 0.5000 9.0 9.0 3.0 9.0 9.0 9.0 7.0 9.0 6.0
5.0 1.0 7.0 0.2500 9.0 9.0 9.0 6.0 9.0 4.0 9.0 9.0 3.0 1.0 7.0
0.1250 9.0 4.0 0.0 9.0 7.0 7.0 1.0 9.0 4.0 1.0 1.0 5.0 0.0625 9.0
3.0 0.0 9.0 3.0 0.0 0.0 7.0 1.0 0.0 0.0 1.0 0.0313 9.0 1.0 0.0 9.0
3.0 0.0 0.0 7.0 0.0 0.0 0.0 1.0 0.0156 9.0 2.0 0.0 9.0 2.0 0.0 0.0
7.0 0.0 0.0 0.0 0.0 124 0.5000 7.0 9.0 0.0 9.0 7.0 6.0 1.0 9.0 3.0
2.0 0.0 1.0 0.2500 4.0 9.0 3.0 9.0 6.0 1.0 0.0 4.0 0.0 0.0 0.0 0.0
0.1250 2.0 9.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 0.0
4.0 1.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 125 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0
4.0 5.0 7.0 0.2500 9.0 9.0 9.0 9.0 7.0 9.0 7.0 9.0 4.0 4.0 4.0 7.0
0.1250 6.0 9.0 2.0 9.0 1.0 4.0 3.0 9.0 3.0 1.0 1.0 6.0 0.0625 4.0
9.0 3.0 9.0 0.0 4.0 0.0 5.0 0.0 1.0 1.0 3.0 0.0313 2.0 6.0 1.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156
0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 126 0.5000 9.0 5.0
3.0 9.0 9.0 9.0 2.0 9.0 7.0 3.0 0.0 8.0 0.2500 9.0 4.0 0.0 9.0 9.0
1.0 0.0 3.0 3.0 0.0 0.0 4.0 0.1250 5.0 0.0 0.0 9.0 0.0 1.0 0.0 0.0
2.0 0.0 0.0 2.0 0.0625 5.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 127 0.5000 9.0 9.0 6.0 9.0 9.0 9.0 0.0 9.0 4.0 3.0 7.0 8.0
0.2500 9.0 5.0 2.0 9.0 7.0 9.0 0.0 9.0 4.0 0.0 0.0 4.0 0.1250 9.0
0.0 9.0 3.0 1.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0625 7.0 0.0 0.0 9.0 3.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 7.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 128 0.2500 9.0 3.0 0.0 9.0 1.0 7.0 2.0 7.0 0.0 0.0
0.0 0.0 0.1250 3.0 2.0 9.0 1.0 9.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0625
1.0 0.0 1.0 9.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 1.0 7.0
0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 129 0.2500 9.0 7.0 8.0 9.0 0.0 9.0 0.0 7.0 4.0
3.0 1.0 1.0 0.1250 9.0 7.0 7.0 9.0 0.0 9.0 1.0 6.0 2.0 1.0 1.0 1.0
0.0625 9.0 0.0 1.0 9.0 1.0 0.0 0.0 1.0 2.0 1.0 0.0 0.0 0.0313 1.0
0.0 1.0 3.0 1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 1.0 4.0
1.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 130 0.2500 9.0 9.0 3.0 9.0 2.0 7.0
7.0 9.0 5.0 6.0 6.0 9.0 0.1250 9.0 9.0 9.0 2.0 9.0 4.0 7.0 3.0 3.0
3.0 7.0 0.0625 9.0 7.0 2.0 9.0 0.0 2.0 1.0 7.0 2.0 1.0 1.0 4.0
0.0313 9.0 1.0 1.0 9.0 0.0 0.0 6.0 0.0 0.0 0.0 1.0 0.0156 1.0 0.0
0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 131 0.2500 9.0 0.0 2.0 9.0
9.0 0.0 2.0 3.0 1.0 0.0 0.0 0.0 0.1250 2.0 0.0 0.0 9.0 2.0 0.0 0.0
0.0 1.0 0.0 0.0 0.0 0.0625 0.0 0.0 0.0 9.0 3.0 0.0 0.0 0.0 1.0 0.0
0.0 0.0 0.0313 0.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 132
0.2500 9.0 7.0 0.0 9.0 5.0 2.0 7.0 9.0 2.0 1.0 1.0 2.0 0.1250 9.0
4.0 9.0 4.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0625 9.0 0.0 0.0 9.0 4.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 133 0.2500 5.0 1.0 9.0 9.0 0.0 1.0 0.0
0.0 0.0 0.0 0.0 0.0 0.1250 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 134 0.2500
7.0 3.0 1.0 9.0 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.1250 0.0 0.0 0.0
9.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 135 0.2500 8.0 7.0 5.0 9.0 1.0
9.0 1.0 7.0 3.0 7.0 1.0 1.0 0.1250 6.0 4.0 1.0 9.0 0.0 9.0 0.0 4.0
1.0 1.0 0.0 2.0 0.0625 3.0 0.0 1.0 9.0 0.0 1.0 0.0 2.0 0.0 1.0 0.0
0.0 0.0313 0.0 0.0 1.0 7.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 0.0156
0.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 136 0.2500 9.0 5.0
0.0 9.0 3.0 0.0 0.0 7.0 2.0 1.0 1.0 3.0 0.1250 9.0 2.0 0.0 9.0 2.0
0.0 0.0 4.0 1.0 1.0 1.0 1.0 0.0625 9.0 1.0 0.0 9.0 1.0 0.0 0.0 2.0
0.0 0.0 0.0 0.0 0.0313 9.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0156 4.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 137
0.2500 9.0 7.0 0.0 9.0 0.0 1.0 0.0 2.0 1.0 0.0 0.0 0.0 0.1250 0.0
0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 0.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 138 0.2500 9.0 2.0 0.0 9.0 4.0 0.0
0.0 2.0 1.0 0.0 0.0 0.0 0.1250 9.0 1.0 0.0 9.0 0.0 0.0 0.0 3.0 0.0
0.0 0.0 0.0 0.0625 0.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0
0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 139 0.2500 9.0 4.0 1.0
9.0 0.0 2.0 1.0 7.0 1.0 2.0 1.0 1.0 0.1250 9.0 3.0 2.0 9.0 0.0 1.0
1.0 0.0 1.0 0.0 0.0 0.0625 0.0 0.0 1.0 9.0 0.0 2.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0313 0.0 1.0 0.0 7.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0
0.0156 0.0 0.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 140 0.2500
7.0 0.0 0.0 9.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.1250 3.0 0.0 0.0
9.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 141 0.2500 9.0 4.0 3.0 9.0 0.0 3.0 2.0 4.0
3.0 0.0 0.0 2.0 0.1250 4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313
0.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0
3.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 142 0.2500 9.0 1.0 0.0 9.0 9.0
2.0 0.0 7.0 1.0 0.0 0.0 2.0 0.1250 4.0 2.0 1.0 9.0 0.0 1.0 0.0 2.0
0.0 1.0 0.0 2.0 0.0625 1.0 4.0 2.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0313 1.0 0.0 0.0 3.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0156
0.0 0.0 1.0 4.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 143 0.2500 9.0 3.0
1.0 9.0 0.0 3.0 1.0 3.0 1.0 1.0 1.0 0.0 0.1250 6.0 2.0 0.0 9.0 1.0
1.0 1.0 3.0 0.0 0.0 0.0 0.0 0.0625 1.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0313 1.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 144 0.2500 9.0 7.0 2.0 9.0 2.0 1.0 1.0 9.0 0.0 0.0 0.0 0.0
0.1250 9.0 4.0 1.0 9.0 2.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0625 0.0
0.0 0.0 9.0 1.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 7.0
1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 6.0 1.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 145 0.2500 6.0 7.0 7.0 9.0 3.0 5.0 1.0 7.0 2.0
1.0 1.0 2.0 0.1250 9.0 5.0 1.0 9.0 1.0 7.0 1.0 3.0 1.0 3.0 0.0 1.0
0.0625 3.0 2.0 6.0 7.0 0.0 0.0 1.0 7.0 0.0 2.0 1.0 0.0 0.0313 2.0
0.0 1.0 9.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 0.0156 0.0 0.0 1.0 7.0
0.0 0.0 0.0 1.0 0.0 1.0 0.0 0.0 146 0.2500 9.0 3.0 1.0 9.0 2.0 0.0
0.0 5.0 1.0 1.0 1.0 0.0 0.1250 9.0 0.0 1.0 9.0 2.0 0.0 0.0 3.0 0.0
0.0 0.0 0.0 0.0625 1.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0
0.0 0.0 1.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 147 0.2500 7.0 4.0 5.0 9.0
1.0 0.0 0.0 4.0 1.0 0.0 0.0 2.0 0.1250 4.0 1.0 0.0 9.0 1.0 0.0 0.0
1.0 0.0 0.0 0.0 1.0 0.0625 0.0 0.0 0.0 6.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0313 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0
0.0156 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 1.0 0.0 0.0 1.0 148 0.2500
4.0 4.0 0.0 9.0 0.0 0.0 0.0 5.0 0.0 0.0 0.0 1.0 0.1250 4.0 0.0 0.0
9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0625 1.0 0.0 0.0 9.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0 0.0 0.0 6.0 0.0 0.0 0.0 1.0 0.0
0.0 0.0 0.0 149 0.2500 7.0 0.0 0.0 9.0 0.0 2.0 0.0 0.0 7.0 2.0 2.0
2.0 0.1250 3.0 0.0 0.0 3.0 0.0 0.0 0.0 0.0 3.0 2.0 0.0 0.0 150
0.2500 9.0 7.0 2.0 9.0 2.0 9.0 4.0 9.0 2.0 1.0 1.0 1.0 0.1250 9.0
3.0 1.0 9.0 0.0 9.0 2.0 4.0 0.0 2.0 1.0 2.0 0.0625 4.0 0.0 2.0 9.0
0.0 0.0 0.0 0.0 0.0 1.0 0.0 1.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 151 0.2500 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0
9.0 9.0 9.0 0.1250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 7.0 9.0 8.0 9.0
0.0625 9.0 9.0 2.0 9.0 4.0 9.0 7.0 9.0 4.0 5.0 5.0 7.0 0.0313 9.0
7.0 2.0 9.0 4.0 9.0 9.0 9.0 5.0 5.0 6.0 7.0 0.0156 9.0 1.0 0.0 9.0
2.0 4.0 2.0 9.0 2.0 2.0 2.0 7.0 152 0.2500 9.0 6.0 3.0 9.0 6.0 7.0
1.0 9.0 2.0 1.0 1.0 2.0 0.1250 9.0 2.0 0.0 9.0 1.0 4.0 1.0 1.0 2.0
1.0 1.0 1.0 0.0625 0.0 0.0 1.0 9.0 0.0 1.0 0.0 1.0 2.0 1.0 1.0 1.0
0.0313 0.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 153 0.2500
2.0 1.0 0.0 7.0 1.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 0.1250 0.0 0.0 0.0
1.0 0.0 1.0 0.0 1.0 0.0 0.0 0.0 0.0 154 0.2500 9.0 9.0 9.0 9.0 9.0
9.0 9.0 9.0 8.0 9.0 9.0 9.0 0.1250 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
9.0 8.0 9.0 0.0625 9.0 9.0 9.0 9.0 4.0 9.0 9.0 9.0 5.0 8.0 8.0 8.0
0.0313 9.0 5.0 0.0 9.0 0.0 9.0 4.0 7.0 2.0 4.0 2.0 7.0 0.0156 9.0
3.0 0.0 9.0 0.0 0.0 0.0 2.0 0.0 3.0 0.0 5.0 155 0.2500 7.0 4.0 0.0
9.0 4.0 2.0 0.0 0.0 4.0 2.0 0.0 2.0 0.1250 4.0 2.0 0.0 9.0 4.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0625 2.0 0.0 0.0 0.0 4.0 0.0 0.0 0.0 0.0
0.0 0.0 0.0 156 0.2500 9.0 9.0 0.0 9.0 9.0 9.0 0.0 9.0 7.0 3.0 3.0
5.0 0.1250 9.0 5.0 9.0 4.0 9.0 0.0 2.0 0.0 0.0 0.0 2.0 0.0625 9.0
0.0 0.0 9.0 4.0 3.0 0.0 2.0 0.0 0.0 0.0 1.0 0.0313 4.0 0.0 0.0 9.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 157 0.2500 6.0 1.0 5.0 9.0 4.0 2.0
0.0 1.0 4.0 0.0 0.0 1.0 0.1250 4.0 0.0 1.0 9.0 0.0 1.0 1.0 2.0 2.0
0.0 0.0 1.0 0.0625 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0313 0.0 0.0 1.0 1.0 0.0 0.0 0.0 0.0 1.0 0.0 0.0 0.0 158 0.2500
9.0 9.0 5.0 9.0 6.0 9.0 9.0 9.0 9.0 8.0 7.0 9.0 0.1250 9.0 9.0 9.0
9.0 7.0 9.0 9.0 9.0 7.0 7.0 7.0 9.0 0.0625 9.0 7.0 4.0 9.0 5.0 7.0
9.0 9.0 6.0 7.0 5.0 8.0 0.0313 9.0 3.0 3.0 9.0 0.0 4.0 7.0 9.0 4.0
4.0 4.0 7.0 0.0156 9.0 1.0 1.0 9.0 0.0 1.0 2.0 7.0 1.0 3.0 1.0 5.0
159 0.2500 9.0 8.0 7.0 9.0 5.0 9.0 3.0 7.0 3.0 2.0 3.0 7.0 0.1250
9.0 6.0 3.0 9.0 5.0 7.0 2.0 9.0 2.0 1.0 1.0 2.0 0.0625 9.0 4.0 3.0
8.0 1.0 9.0 0.0 7.0 1.0 0.0 0.0 1.0 0.0313 9.0 3.0 1.0 9.0 0.0 2.0
1.0 8.0 0.0 0.0 0.0 0.0 0.0156 2.0 1.0 0.0 7.0 0.0 0.0 0.0 1.0 1.0
0.0 0.0 0.0 160 0.5000 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 9.0 8.0 7.0
8.0 0.2500 9.0 9.0 7.0 9.0 7.0 8.0 9.0 7.0 9.0 7.0 4.0 5.0 0.1250
9.0 9.0 1.0 9.0 0.0 9.0 2.0 7.0 2.0 1.0 1.0 2.0 0.0625 9.0 9.0 2.0
9.0 0.0 9.0 1.0 7.0 1.0 1.0 1.0 1.0 0.0313 9.0 6.0 0.0 9.0 0.0 6.0
0.0 1.0 1.0 0.0 0.0 0.0 0.0156 5.0 7.0 0.0 2.0 0.0 3.0 0.0 0.0 1.0
0.0 0.0 0.0 161 0.5000 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0
9.0 0.2500 9.0 9.0 9.0 9.0 7.0 9.0 7.0 9.0 9.0 9.0 7.0 6.0 0.1250
9.0 9.0 9.0 9.0 7.0 9.0 4.0 9.0 7.0 7.0 4.0 5.0 0.0625 2.0 5.0 1.0
9.0 3.0 7.0 0.0 7.0 1.0 7.0 1.0 1.0 0.0313 1.0 3.0 0.0 7.0 0.0 2.0
0.0 0.0 1.0 1.0 0.0 0.0 0.0156 0.0 0.0 0.0 6.0 0.0 0.0 0.0 0.0 0.0
0.0 0.0 162 0.2500 9.0 9.0 4.0 9.0 3.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0
0.1250 9.0 9.0 0.0 9.0 3.0 9.0 9.0 9.0 5.0 6.0 7.0 9.0 0.0625 9.0
5.0 0.0 9.0 0.0 4.0 8.0 9.0 2.0 5.0 7.0 9.0 0.0313 9.0 3.0 9.0 0.0
0.0 4.0 9.0 2.0 3.0 3.0 7.0 0.0156 9.0 0.0 0.0 9.0 0.0 0.0 1.0 9.0
2.0 2.0 0.0 6.0 163 0.2500 9.0 9.0 5.0 9.0 3.0 9.0 9.0 9.0 5.0 8.0
7.0 8.0 0.1250 9.0 9.0 0.0 9.0 0.0 9.0 8.0 9.0 3.0 7.0 7.0 7.0
0.0625 9.0 9.0 0.0 9.0 0.0 3.0 7.0 9.0 3.0 5.0 3.0 7.0 0.0313 9.0
3.0 0.0 9.0 0.0 0.0 4.0 9.0 2.0 3.0 0.0 5.0 0.0156 9.0 0.0 0.0 9.0
0.0 0.0 2.0 9.0 0.0 1.0 0.0 5.0 164 0.5000 9.0 9.0 5.0 9.0 9.0 9.0
9.0 9.0 7.0 9.0 9.0 9.0 0.2500 9.0 9.0 9.0 9.0 7.0 9.0 9.0 9.0 7.0
7.0 7.0 8.0 0.1250 9.0 7.0 7.0 9.0 9.0 9.0 9.0 9.0 7.0 5.0 6.0 7.0
0.0625 9.0 7.0 7.0 9.0 4.0 9.0 7.0 9.0 5.0 3.0 4.0 6.0 0.0313 9.0
7.0 0.0 9.0 4.0 9.0 7.0 9.0 2.0 1.0 1.0 3.0 0.0156 6.0 6.0 1.0 9.0
3.0 4.0 0.0 4.0 1.0 1.0 1.0 2.0 165 0.5000 9.0 9.0 7.0 9.0 8.0 9.0
7.0 9.0 6.0 5.0 4.0 7.0 0.2500 9.0 7.0 7.0 9.0 7.0 9.0 6.0 9.0 5.0
3.0 2.0 4.0 0.1250 9.0 7.0 1.0 9.0 4.0 2.0 3.0 9.0 4.0 1.0 1.0 1.0
0.0625 0.0 0.0 0.0 9.0 0.0 0.0 6.0 4.0 0.0 0.0 1.0 0.0313 0.0 1.0
0.0 9.0 0.0 0.0 0.0 6.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 4.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 0.0 166 0.5000 9.0 7.0 6.0 9.0 8.0 8.0 4.0 9.0
6.0 5.0 3.0 6.0 0.2500 9.0 7.0 4.0 9.0 7.0 6.0 0.0 6.0 6.0 1.0 1.0
3.0 0.1250 7.0 6.0 0.0 9.0 5.0 2.0 0.0 6.0 2.0 1.0 1.0 1.0 0.0625
1.0 3.0 2.0 3.0 2.0 1.0 1.0 2.0 1.0 1.0 1.0 0.0313 2.0 0.0 0.0 0.0
0.0 3.0 0.0 0.0 2.0 0.0 0.0 0.0 0.0156 0.0 1.0 0.0 1.0 0.0 0.0 0.0
0.0 0.0 0.0 0.0 0.0 167 0.5000 9.0 8.0 9.0 9.0 7.0 9.0 8.0 9.0 7.0
6.0 5.0 7.0 0.2500 9.0 7.0 4.0 9.0 6.0 9.0 9.0 9.0 4.0 5.0 4.0 6.0
0.1250 9.0 6.0 1.0 9.0 9.0 3.0 9.0 9.0 4.0 4.0 3.0 3.0 0.0625 9.0
7.0 1.0 9.0 7.0 2.0 6.0 9.0 0.0 1.0 1.0 3.0 0.0313 0.0 0.0 0.0 7.0
5.0 0.0 0.0 7.0 0.0 0.0 0.0 0.0 0.0156 1.0 0.0 7.0 1.0 0.0 0.0 5.0
1.0 0.0 0.0 0.0 168 0.2500 9.0 5.0 0.0 9.0 3.0 4.0 0.0 5.0 0.0 0.0
0.0 0.0 0.1250 9.0 0.0 0.0 9.0 0.0 3.0 0.0 0.0 0.0 0.0 0.0 0.0
0.0625 4.0 0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0313 0.0
0.0 0.0 9.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0156 0.0 0.0 0.0 3.0
0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 169 0.2500 5.0 3.0 0.0 4.0 0.0 3.0
0.0 0.0 3.0 0.0 0.0 0.0 170 0.2500 9.0 9.0 3.0 9.0 3.0 9.0 9.0 9.0
8.0 9.0 9.0 9.0 0.1250 9.0 9.0 3.0 9.0 0.0 7.0 9.0 9.0 5.0 7.0 8.0
9.0 0.0625 9.0 4.0 0.0 9.0 0.0 9.0 9.0 4.0 6.0 7.0 8.0 0.0313 6.0
0.0 0.0 9.0 0.0 7.0 9.0 9.0 4.0 0.0 6.0 7.0 0.0156 0.0 0.0 0.0 9.0
0.0 3.0 3.0 9.0 1.0 0.0 0.0 5.0 171 0.2500 9.0 9.0 9.0 9.0 6.0 9.0
9.0 9.0 8.0 8.0 8.0 9.0 0.1250 9.0 9.0 4.0 9.0 5.0 9.0 9.0 9.0 7.0
6.0 6.0 8.0 0.0625 9.0 9.0 2.0 9.0 9.0 8.0 9.0 6.0 5.0 6.0 8.0
0.0313 9.0 4.0 5.0 9.0 0.0 3.0 4.0 9.0 2.0 4.0 3.0 6.0 0.0156 9.0
3.0 4.0 9.0 0.0 2.0 0.0 7.0 1.0 2.0 2.0 2.0 172 0.2500 9.0 9.0 9.0
9.0 9.0 9.0 9.0 9.0 9.0 8.0 9.0 9.0 0.1250 9.0 9.0 9.0 9.0 7.0 9.0
8.0 9.0 9.0 7.0 7.0 9.0 0.0625 9.0 9.0 7.0 9.0 5.0 7.0 8.0 9.0 7.0
7.0 7.0 8.0 0.0313 9.0 7.0 3.0 9.0 0.0 7.0 6.0 7.0 2.0 5.0 3.0 7.0
0.0156 9.0 5.0 1.0 9.0 0.0 2.0 4.0 5.0 1.0 2.0 2.0 4.0
EXAMPLE 39
Rice Tolerance to Post-Transplant Applications and Preemergence
Weed Control Under Flooded Paddy Conditions
[0720] The tolerance of transplanted rice to post-transplanted
herbicide applications is determined as follows: two ten-day-old
rice seedlings (cv. Tebonnet) are transplanted into silt loam soil
in 32 oz. plastic containers with a diameter of 10.5 cm and no
drainage holes. After transplanting, the containers are flooded and
the water level is maintained at 1.5 to 3 cm above the soil
surface. Three days after transplanting, the flooded soil surface
of the containers is treated with the selected aqueous/acetone
50/50 v/v mixture containing the test compounds to provide the
equivalent of about 0.0313 to 0.500 kg/ha of active ingredient. The
treated containers are placed on greenhouse benches, watered such
that the water level is maintained as stated above, and cared for
in accordance with conventional greenhouse procedures. Three to
four weeks after treatment, the test is terminated and each
container is examined and herbicidal effect rated according to the
rating system provided in Example 37. The data obtained are
reported in Table III. The compounds evaluated are reported by
compound number given in Example 37.
[0721] Preemergence herbicidal activity under flooded paddy
conditions is determined as follows: plant seeds or propagating
organs are planted in the top 0.5 cm of silt loam soil in 32 oz.
plastic containers with a diameter of 10.5 cm and no drainage
holes. Water is added to these containers and maintained at 1.5 to
3 cm above the soil surface for the duration of the experiment. The
test compounds are applied as aqueous/acetone mixtures 50/50 v/v
pipetted directly into the flood water to give the equivalent of
about 0.0313 to 0.500 kg/ha of active ingredient. The treated
containers are placed on greenhouse benches and cared for in
accordance with conventional greenhouse procedures. Three to four
weeks after treatment, the test is terminated and each container is
examined and herbicidal effect rated according to the rating system
provided in Example 37. The data obtained are reported in Table
III. The compounds evaluated are reported by compound number given
in Example 37.
[0722] Plant species employed in this example are reported by
header abbreviation, common name and scientific name.
PLANT SPECIES EMPLOYED IN RICE TOLERANCE/PREEMERGENCE WEED CONTROL
EVALUATIONS
[0723]
21 Header Abbr. Common Name Scientific Name ECHORC Watergrass
(Calif.) Echinochloa oryzoides (Ard.) Fritsch. CYPIR Rice Flatsedge
Cyperus iria CYPSE Flatsedge Cyperus serotinus, Rottb. MOOVA
Monochoria Monochoria vaginalis, Presl. SAGPY Arrowhead (Pygmaea)
Sagittaria pygmaea, L. ORYSAT Rice, Tebonnet Oryza sativa, (L.)
Tebonnet
[0724]
22TABLE III Paddy Conditions - Post-Transplant Rice Preemergence
Weeds E O C C C M S R H Y Y O A Y O P P O G S Compound Rate R I S V
P A Number (kg/ha) C R E A Y T 1 0.5000 9.0 9.0 8.0 9.0 0.0 4.0
0.2500 7.0 9.0 2.0 9.0 0.0 3.0 0.1250 6.0 9.0 0.0 9.0 0.0 2.0
0.0625 4.0 7.0 0.0 9.0 0.0 2.0 0.0313 2.0 2.0 0.0 8.0 0.0 1.0 2
0.5000 9.0 1.0 0.0 9.0 0.0 3.0 0.2500 8.0 0.0 0.0 9.0 0.0 2.0
0.1250 7.0 0.0 0.0 9.0 0.0 1.0 0.0625 2.0 0.0 0.0 9.0 0.0 0.0
0.0313 2.0 0.0 0.0 4.0 0.0 0.0 3 0.5000 4.0 0.0 0.0 9.0 0.0 3.0
0.2500 2.0 0.0 0.0 9.0 0.0 2.0 0.1250 0.0 0.0 0.0 9.0 0.0 2.0
0.0625 0.0 0.0 0.0 2.0 0.0 0.0 4 0.5000 9.0 9.0 0.0 9.0 0.0 3.0
0.2500 8.0 9.0 0.0 9.0 0.0 3.0 0.1250 7.0 8.0 0.0 8.0 0.0 2.0
0.0625 4.0 4.0 0.0 7.0 0.0 2.0 0.0313 2.0 0.0 0.0 2.0 0.0 0.0 5
0.5000 4.0 0.0 1.0 8.0 0.0 2.0 0.2500 2.0 0.0 0.0 4.0 0.0 1.0
0.1250 1.0 0.0 0.0 2.0 0.0 1.0 6 0.5000 7.0 7.0 0.0 9.0 0.0 0.0
0.2500 7.0 6.0 0.0 9.0 0.0 0.0 0.1250 2.0 4.0 0.0 8.0 0.0 0.0
0.0625 0.0 2.0 0.0 8.0 0.0 0.0 0.0313 0.0 0.0 0.0 2.0 0.0 0.0 7
0.2500 9.0 9.0 9.0 9.0 9.0 9.0 0.1250 9.0 9.0 7.0 9.0 8.0 8.0
0.0625 9.0 9.0 7.0 9.0 4.0 7.0 0.0313 8.0 8.0 4.0 9.0 2.0 7.0 8
0.2500 8.5 4.0 0.0 9.0 0.0 6.0 0.1250 7.5 0.0 0.0 9.0 0.0 5.0
0.0625 6.5 0.0 0.0 9.0 0.0 3.5 0.0313 6.5 0.0 0.0 9.0 0.0 2.5 9
0.2500 7.0 6.0 7.0 9.0 2.0 9.0 0.1250 4.0 4.0 2.0 9.0 1.0 9.0
0.0625 2.0 2.0 0.0 9.0 0.0 8.0 0.0313 0.0 0.0 0.0 9.0 0.0 7.0 10
0.2500 2.0 4.0 0.0 9.0 0.0 7.0 0.1250 2.0 2.0 0.0 9.0 0.0 6.0
0.0625 1.0 0.0 0.0 9.0 0.0 4.0 0.0313 0.0 0.0 0.0 9.0 0.0 3.0 11
0.2500 3.0 0.0 0.0 7.0 0.0 3.0 0.1250 2.0 0.0 0.0 4.0 0.0 3.0
0.0625 2.0 0.0 0.0 1.0 0.0 2.0 0.0313 1.0 0.0 0.0 0.0 0.0 2.0 12
0.2500 9.0 0.0 6.0 9.0 0.0 7.0 0.1250 8.5 1.0 1.0 9.0 4.0 5.5
0.0625 9.0 0.0 3.0 9.0 1.0 3.5 0.0313 5.0 0.0 1.0 9.0 0.0 3.0 13
0.2500 9.0 1.0 0.0 9.0 0.0 5.0 0.1250 8.0 0.5 0.0 9.0 0.0 3.0
0.0625 7.0 0.0 0.0 9.0 0.0 2.5 0.0313 5.5 0.0 0.0 9.0 0.0 1.5
0.0156 3.5 0.0 0.0 7.5 0.0 1.0 14 0.2500 9.0 0.0 0.0 0.0 0.0 0.0
0.1250 7.5 4.5 3.0 4.5 0.0 1.0 0.0625 4.5 2.5 0.0 4.5 0.0 0.5
0.0313 1.5 2.0 0.0 4.5 0.0 0.0 15 0.2500 9.0 7.0 0.0 9.0 0.0 3.0
0.1250 9.0 6.0 0.0 9.0 0.0 3.0 0.0625 9.0 2.0 0.0 9.0 0.0 2.0
0.0313 6.0 2.0 0.0 9.0 0.0 0.0 16 0.2500 0.0 9.0 0.0 3.0 0.0 0.0
0.1250 0.0 4.0 0.0 9.0 0.0 0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 17 0.2500 9.0 9.0 9.0 9.0 4.0 9.0
0.1250 9.0 6.0 9.0 9.0 4.0 9.0 0.0625 9.0 0.0 9.0 9.0 0.0 6.0
0.0313 4.0 0.0 9.0 9.0 0.0 4.0 18 0.4630 7.0 0.0 4.0 9.0 6.0 3.0
0.2310 7.0 0.0 0.0 9.0 0.0 3.0 0.1160 7.0 0.0 0.0 9.0 0.0 3.0 19
0.4630 9.0 0.0 4.0 9.0 3.0 3.0 0.2310 7.0 0.0 4.0 9.0 3.0 3.0
0.1160 7.0 0.0 4.0 9.0 0.0 3.0 20 0.4630 7.0 0.0 5.0 9.0 3.0 2.0
0.2310 7.0 0.0 5.0 9.0 0.0 2.0 0.1160 7.0 0.0 5.0 9.0 0.0 2.0 21
0.4630 5.0 0.0 0.0 0.0 0.0 0.0 0.2310 4.0 0.0 0.0 0.0 0.0 0.0
0.1160 2.0 0.0 0.0 0.0 0.0 0.0 22 0.4630 9.0 5.0 4.0 9.0 5.0 7.0
0.2310 9.0 0.0 4.0 9.0 4.0 6.0 0.1160 6.0 0.0 4.0 9.0 4.0 3.0 23
0.4630 4.0 0.0 0.0 9.0 3.0 5.0 0.2310 4.0 0.0 0.0 9.0 0.0 4.0
0.1160 4.0 0.0 0.0 9.0 0.0 4.0 24 0.2500 9.0 0.0 9.0 0.0 0.0 0.1250
9.0 0.0 9.0 0.0 0.0 0.0625 9.0 0.0 9.0 0.0 0.0 0.0313 4.0 0.0 0.0
0.0 0.0 25 0.2500 9.0 0.0 9.0 5.0 5.0 0.1250 7.0 0.0 9.0 5.0 4.0
0.0625 6.0 0.0 9.0 0.0 4.0 0.0313 4.0 0.0 9.0 0.0 3.0 26 0.2500 9.0
9.0 9.0 7.0 2.0 0.1250 9.0 7.0 9.0 5.0 1.0 0.0625 9.0 4.0 9.0 4.0
0.0 0.0313 7.0 2.0 9.0 0.0 0.0 27 0.2500 9.0 9.0 9.0 9.0 4.0 4.0
0.1250 9.0 6.0 0.0 9.0 4.0 4.0 0.0625 7.0 4.0 0.0 9.0 0.0 2.0
0.0313 6.0 3.0 0.0 9.0 0.0 1.0 28 0.2500 9.0 9.0 0.0 9.0 0.0 1.0
0.1250 7.0 9.0 0.0 9.0 0.0 0.0 0.0625 4.0 9.0 0.0 9.0 0.0 0.0
0.0313 0.0 9.0 0.0 9.0 0.0 0.0 29 0.2500 7.0 0.0 0.0 0.0 0.0 3.0
0.1250 7.0 0.0 0.0 0.0 0.0 2.0 0.0625 7.0 0.0 0.0 0.0 0.0 1.0
0.0313 4.0 0.0 0.0 0.0 0.0 0.0 30 0.2500 0.0 4.5 0.0 4.5 2.0 0.0
0.1250 0.0 2.0 0.0 1.5 0.0 0.0 31 0.2500 5.0 2.5 0.0 2.5 0.0 0.0
0.1250 2.0 0.0 0.0 0.0 0.0 0.0 0.0625 1.0 0.0 0.0 0.0 0.0 0.0 32
0.2500 6.0 0.0 0.0 0.0 0.0 0.1250 3.0 0.0 0.0 0.0 0.0 33 0.2500 0.0
0.0 0.0 0.0 0.0 34 0.2500 9.0 0.0 0.0 0.0 6.0 0.1250 4.0 0.0 0.0
0.0 4.0 0.0625 4.0 0.0 0.0 0.0 3.0 0.0313 3.0 0.0 0.0 0.0 3.0 35
0.2500 6.0 0.0 0.0 3.0 3.0 0.1250 3.0 0.0 0.0 0.0 2.0 36 0.2500 9.0
9.0 4.0 9.0 5.0 0.1250 7.0 5.0 2.0 3.0 3.0 0.0625 6.0 5.0 0.0 0.0
3.0 0.0313 4.0 0.0 0.0 0.0 3.0 37 0.2500 7.0 0.0 0.0 3.0 3.0 0.1250
7.0 0.0 0.0 0.0 0.0 0.0625 6.0 0.0 0.0 0.0 0.0 0.0313 4.0 0.0 0.0
0.0 0.0 38 0.2500 7.0 5.0 3.0 9.0 9.0 7.0 0.1250 4.0 5.0 0.0 9.0
4.0 5.0 0.0625 2.0 3.0 0.0 9.0 3.0 5.0 0.0313 0.0 3.0 0.0 9.0 0.0
2.0 39 0.2500 3.0 0.0 0.0 9.0 4.0 3.0 0.1250 2.0 0.0 0.0 9.0 0.0
2.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0
40 0.2500 9.0 0.0 6.0 9.0 0.0 3.0 0.1250 5.0 0.0 0.0 9.0 0.0 3.0
0.0625 5.0 0.0 0.0 9.0 0.0 3.0 0.0313 5.0 0.0 0.0 9.0 0.0 2.0 41
0.2500 7.0 4.0 7.0 9.0 6.0 5.0 0.1250 6.0 0.0 2.0 9.0 0.0 5.0
0.0625 4.0 0.0 0.0 9.0 0.0 5.0 0.0313 3.0 0.0 0.0 6.0 0.0 4.0 42
0.2500 6.0 0.0 0.0 9.0 3.0 0.0 0.1250 5.0 0.0 0.0 9.0 0.0 0.0
0.0625 5.0 0.0 0.0 9.0 0.0 0.0 0.0313 5.0 0.0 0.0 7.0 0.0 0.0 43
0.2500 9.0 5.0 9.0 9.0 9.0 6.0 0.1250 7.0 4.0 8.0 9.0 7.0 4.0
0.0625 6.0 2.0 5.0 9.0 7.0 3.0 0.0313 5.0 0.0 5.0 9.0 7.0 2.0 44
0.2500 8.0 9.0 0.0 9.0 5.0 0.1250 7.0 6.0 0.0 7.0 3.0 0.0625 6.0
6.0 0.0 4.0 3.0 0.0313 6.0 5.0 0.0 4.0 0.0 45 0.2500 7.0 7.0 0.0
9.0 4.0 3.0 0.1250 7.0 7.0 9.0 0.0 2.0 0.0625 4.0 3.0 0.0 7.0 0.0
2.0 0.0313 3.0 0.0 0.0 7.0 0.0 3.0 46 0.2500 4.0 0.0 6.0 7.0 3.0
3.0 0.1250 0.0 0.0 0.0 6.0 0.0 2.0 0.0625 0.0 0.0 0.0 4.0 0.0 2.0
0.0313 0.0 0.0 0.0 3.0 0.0 0.0 47 0.2500 7.0 6.0 0.0 9.0 7.0 3.0
0.1250 4.0 4.0 0.0 9.0 4.0 0.0 0.0625 2.0 0.0 0.0 6.0 0.0 0.0
0.0313 0.0 0.0 0.0 5.0 0.0 0.0 48 0.2500 6.0 5.0 0.0 6.0 6.0 6.0
0.1250 3.0 2.0 0.0 3.0 3.0 4.0 49 0.2500 7.0 7.0 4.0 9.0 7.0 7.0
0.1250 5.0 2.0 9.0 6.0 7.0 0.0625 2.0 0.0 3.0 9.0 4.0 5.0 0.0313
0.0 0.0 2.0 9.0 2.0 5.0 50 0.2500 7.0 0.0 0.0 7.0 3.0 1.0 0.1250
7.0 0.0 0.0 3.0 3.0 0.0 0.0625 7.0 0.0 0.0 0.0 2.0 0.0 0.0313 4.0
0.0 0.0 0.0 2.0 0.0 51 0.2500 0.0 6.0 0.0 4.0 0.0 0.0 0.1250 0.0
3.0 0.0 4.0 0.0 0.0 0.0625 0.0 2.0 0.0 3.0 0.0 0.0 52 0.2500 0.0
2.0 0.0 4.0 0.0 0.0 53 0.2500 3.0 9.0 0.0 9.0 0.0 3.0 0.1250 2.0
9.0 0.0 9.0 0.0 2.0 0.0625 0.0 2.0 0.0 2.0 0.0 0.0 0.0313 0.0 2.0
0.0 2.0 0.0 0.0 54 0.2500 9.0 4.0 4.0 6.0 2.0 4.0 0.1250 7.0 4.0
0.0 6.0 0.0 3.0 0.0625 5.0 4.0 0.0 0.0 0.0 2.0 0.0313 5.0 0.0 0.0
0.0 0.0 0.0 55 0.2500 7.0 9.0 0.0 9.0 0.0 4.0 0.1250 7.0 9.0 0.0
9.0 0.0 1.0 0.0625 7.0 9.0 0.0 9.0 0.0 1.0 0.0313 7.0 9.0 0.0 9.0
0.0 0.0 56 0.2500 5.0 0.0 0.0 9.0 0.0 2.0 0.1250 3.0 0.0 0.0 9.0
0.0 0.0 0.0625 0.0 0.0 0.0 6.0 0.0 0.0 0.0313 0.0 0.0 0.0 6.0 0.0
0.0 57 0.2500 5.0 9.0 3.0 9.0 6.0 4.0 0.1250 2.0 9.0 0.0 9.0 0.0
0.0 0.0625 2.0 9.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0
58 0.2500 9.0 3.0 5.0 9.0 4.0 5.0 0.1250 7.0 2.0 5.0 3.0 0.0 4.0
0.0625 7.0 0.0 5.0 0.0 0.0 4.0 0.0313 7.0 0.0 5.0 0.0 0.0 4.0 59
0.2500 7.0 9.0 7.0 9.0 3.0 2.0 0.1250 5.0 0.0 0.0 0.0 0.0 2.0
0.0625 4.0 0.0 0.0 0.0 0.0 0.0 60 0.2500 9.0 6.0 4.0 9.0 9.0 5.0
0.1250 9.0 6.0 4.0 9.0 9.0 5.0 0.0625 9.0 3.0 2.0 9.0 4.0 4.0
0.0313 7.0 3.0 2.0 9.0 3.0 4.0 61 0.2500 0.0 0.0 0.0 0.0 0.0 0.0 62
0.2500 5.0 9.0 0.0 9.0 6.0 4.0 0.1250 2.0 9.0 0.0 9.0 3.0 3.0
0.0625 0.0 2.0 0.0 9.0 0.0 3.0 0.0313 0.0 0.0 0.0 4.0 0.0 2.0 63
0.2500 5.0 7.0 0.0 9.0 9.0 3.0 0.1250 5.0 7.0 0.0 9.0 9.0 3.0
0.0625 0.0 6.0 0.0 9.0 7.0 3.0 0.0313 0.0 2.0 0.0 9.0 4.0 3.0 64
0.2500 9.0 7.0 0.0 9.0 8.0 6.0 0.1250 6.0 2.0 0.0 9.0 5.0 5.0
0.0625 6.0 2.0 0.0 9.0 3.0 4.0 0.0313 5.0 0.0 0.0 7.0 0.0 3.0 65
0.2500 7.0 8.0 0.0 9.0 7.0 6.0 0.1250 6.0 7.0 0.0 9.0 5.0 6.0
0.0625 5.0 7.0 0.0 9.0 4.0 3.0 0.0313 5.0 6.0 0.0 9.0 2.0 2.0 66
0.2500 9.0 7.0 4.0 9.0 4.0 3.0 0.1250 9.0 7.0 4.0 9.0 4.0 3.0
0.0625 7.0 6.0 0.0 9.0 4.0 2.0 0.0313 7.0 6.0 0.0 9.0 3.0 2.0 67
0.2500 5.0 8.0 3.0 9.0 6.0 6.0 0.1250 5.0 5.0 3.0 9.0 4.0 4.0
0.0625 4.0 5.0 3.0 9.0 4.0 3.0 0.0313 0.0 5.0 0.0 9.0 0.0 2.0 68
0.2500 7.0 8.0 0.0 9.0 3.0 4.0 0.1250 7.0 5.0 0.0 9.0 0.0 2.0
0.0625 5.0 0.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 3.0 0.0 0.0 69
0.2500 7.0 3.0 9.0 3.0 3.0 0.1250 5.0 3.0 9.0 3.0 2.0 0.0625 4.0
3.0 3.0 0.0 2.0 0.0313 0.0 3.0 3.0 0.0 0.0 70 0.2500 0.0 2.0 3.0
4.0 2.0 0.1250 0.0 2.0 0.0 4.0 2.0 0.0625 0.0 2.0 0.0 4.0 0.0
0.0313 0.0 0.0 0.0 4.0 0.0 71 0.2500 7.0 7.0 3.0 0.0 4.0 0.1250 0.0
3.0 3.0 0.0 4.0 72 0.2500 9.0 9.0 9.0 4.0 3.0 0.1250 9.0 7.0 9.0
4.0 3.0 0.0625 9.0 6.0 0.0 4.0 2.0 0.0313 9.0 6.0 0.0 4.0 1.0 73
0.2500 7.0 6.0 4.0 4.0 6.0 0.1250 3.0 0.0 2.0 3.0 5.0 74 0.2500 9.0
0.0 9.0 9.0 3.0 0.1250 9.0 0.0 5.0 3.0 2.0 0.0625 9.0 0.0 5.0 3.0
0.0 0.0313 7.0 0.0 0.0 3.0 0.0 75 0.2500 9.0 6.0 3.0 3.0 2.0 0.1250
9.0 6.0 3.0 0.0 1.0 0.0625 6.0 0.0 3.0 0.0 0.0 0.0313 6.0 0.0 2.0
0.0 0.0 76 0.2500 9.0 6.0 3.0 4.0 4.0 0.1250 9.0 0.0 2.0 4.0 3.0
0.0625 7.0 0.0 2.0 0.0 2.0 0.0313 4.0 0.0 2.0 0.0 2.0 77 0.2500 9.0
0.0 4.0 0.0 3.0 0.1250 9.0 0.0 0.0 0.0 3.0 0.0625 9.0 0.0 0.0 0.0
2.0 0.0313 9.0 0.0 0.0 0.0 2.0 78 0.2500 9.0 9.0 9.0 4.0 1.0 0.1250
9.0 6.0 7.0 2.0 0.0 0.0625 7.0 5.0 6.0 0.0 0.0 0.0313 7.0 5.0 6.0
0.0 0.0 79 0.2500 8.0 6.0 9.0 4.0 3.0 0.1250 7.0 2.0 0.0 4.0 3.0
0.0625 6.0 0.0 0.0 0.0 2.0 0.0313 5.0 0.0 0.0 0.0 0.0 80 0.2500 9.0
7.0 4.0 0.0 2.0 0.1250 9.0 7.0 3.0 0.0 0.0 0.0625 9.0 7.0 3.0 0.0
0.0 0.0313 9.0 5.0 3.0 0.0 0.0 81 0.2500 3.0 5.0 0.0 0.0 0.0 0.1250
3.0 5.0 0.0 0.0 0.0 0.0625 0.0 4.0 0.0 0.0 0.0 82 0.2500 9.0 3.0
4.0 7.0 3.0 0.1250 6.0 3.0 2.0 4.0 3.0 0.0625 4.0 0.0 0.0 4.0 0.0
0.0313 4.0 0.0 0.0 4.0 0.0 83 0.2500 7.0 7.0 5.0 9.0 9.0 6.0 0.1250
7.0 6.0 3.0 9.0 7.0 5.0 0.0625 6.0 6.0 9.0 7.0 3.0 0.0313 5.0 5.0
0.0 9.0 7.0 3.0 84 0.2500 9.0 9.0 9.0 9.0 9.0 7.0 0.1250 7.0 9.0
9.0 9.0 7.0 6.0 0.0625 5.0 7.0 3.0 9.0 6.0 4.0 0.0313 4.0 3.0 0.0
9.0 2.0 3.0 85 0.2500 9.0 9.0 9.0 9.0 9.0 5.0 0.1250 7.0 9.0 2.0
9.0 9.0 4.0 0.0625 5.0 7.0 2.0 9.0 3.0 4.0 0.0313 4.0 3.0 0.0 9.0
3.0 3.0 86 0.2500 9.0 9.0 9.0 9.0 9.0 5.0 0.1250 9.0 8.0 3.0 9.0
9.0 4.0 0.0625 6.0 7.0 0.0 9.0 9.0 4.0 0.0313 5.0 3.0 0.0 9.0 5.0
3.0 87 0.5000 3.0 7.0 5.0 9.0 7.0 6.0 0.2500 3.0 5.0 5.0 9.0 5.0
4.0 0.1250 2.0 5.0 5.0 9.0 4.0 3.0 0.0625 0.0 5.0 0.0 9.0 4.0 3.0
0.0313 0.0 5.0 0.0 9.0 0.0 2.0 88 0.2500 7.0 0.0 7.0 9.0 9.0 4.0
0.1250 6.0 0.0 7.0 9.0 9.0 4.0 0.0625 6.0 0.0 5.0 9.0 9.0 3.0
0.0313 6.0 0.0 3.0 9.0 6.0 2.0 89 0.2500 6.0 4.0 6.0 9.0 9.0 6.0
0.1250 5.0 2.0 4.0 9.0 9.0 5.0 0.0625 4.0 0.0 0.0 9.0 5.0 4.0
0.0313 3.0 0.0 0.0 9.0 4.0 2.0 90 0.2500 3.0 3.0 3.0 9.0 9.0 3.0
0.1250 0.0 1.0 0.0 9.0 9.0 1.0 0.0625 0.0 0.0 0.0 9.0 6.0 0.0
0.0313 0.0 0.0 0.0 9.0 4.0 0.0 91 0.2500 4.0 0.0 0.0 9.0 0.0 2.0
0.1250 2.0 0.0 0.0 9.0 0.0 0.0 0.0625 0.0 0.0 0.0 9.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 92 0.2500 3.0 7.0 9.0 9.0 9.0 3.0
0.1250 2.0 5.0 9.0 9.0 4.0 3.0 0.0625 0.0 3.0 9.0 9.0 0.0 2.0
0.0313 0.0 3.0 9.0 9.0 0.0 1.0 93 0.2500 7.0 0.0 9.0 9.0 9.0 3.0
0.1250 4.0 0.0 5.0 9.0 3.0 0.0 0.0625 3.0 0.0 0.0 9.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 94 0.2500 7.0 4.0 9.0 9.0 9.0 3.0
0.1250 2.0 4.0 6.0 9.0 5.0 3.0 0.0625 0.0 3.0 9.0 0.0 2.0 0.0313
0.0 0.0 9.0 0.0 0.0 95 0.2500 3.0 7.0 3.0 9.0 8.0 0.1250 3.0 7.0
0.0 9.0 8.0 0.0625 0.0 4.0 0.0 5.0 4.0 0.0313 0.0 4.0 0.0 5.0 3.0
96 0.2500 3.0 6.0 0.0 3.0 5.0 0.1250 0.0 6.0 0.0 3.0 4.0 0.0625 0.0
5.0 0.0 2.0 4.0 0.0313 0.0 0.0 0.0 2.0 3.0 97 0.2500 3.0 4.0 3.0
9.0 5.0 0.1250 2.0 3.0 0.0 9.0 5.0 0.0625 0.0 0.0 0.0 9.0 4.0
0.0313 0.0 0.0 0.0 9.0 1.0 98 0.2500 3.0 9.0 4.0 9.0 7.0 0.1250 1.0
9.0 4.0 9.0 7.0 0.0625 0.0 9.0 3.0 9.0 6.0 0.0313 0.0 9.0 2.0 9.0
2.0 99 0.5000 4.0 0.0 0.0 9.0 4.0 4.0 0.2500 0.0 0.0 0.0 9.0 4.0
4.0 0.1250 0.0 0.0 0.0 9.0 3.0 4.0 0.0625 0.0 0.0 0.0 9.0 0.0 2.0
0.0313 0.0 0.0 0.0 9.0 0.0 2.0 100 0.5000 4.0 9.0 9.0 6.0 4.0
0.2500 3.0 4.0 0.0 9.0 4.0 3.0 0.1250 0.0 0.0 0.0 9.0 0.0 3.0
0.0625 0.0 0.0 0.0 9.0 0.0 3.0 0.0313 0.0 0.0 0.0 9.0 0.0 3.0 101
0.5000 0.0 4.0 0.0 9.0 4.0 3.0 0.2500 0.0 3.0 0.0 9.0 2.0 0.0
0.1250 0.0 0.0 0.0 7.0 0.0 0.0 0.0625 0.0 0.0 0.0 5.0 0.0 0.0
0.0313 0.0 0.0 0.0 5.0 0.0 0.0 102 0.5000 2.0 6.0 0.0 4.0 0.0 4.0
0.2500 0.0 2.0 0.0 0.0 0.0 2.0 103 0.2500 6.0 9.0 6.0 9.0 9.0 6.0
0.1250 5.0 9.0 6.0 9.0 9.0 5.0 0.0625 4.0 6.0 5.0 7.0 9.0 5.0
0.0313 4.0 4.0 5.0 5.0 7.0 4.0 104 0.2500 6.0 9.0 0.0 9.0 9.0 6.0
0.1250 6.0 9.0 0.0 9.0 9.0 7.0 0.0625 5.0 9.0 9.0 9.0 5.0 0.0313
4.0 5.0 0.0 7.0 6.0 3.0 105 0.2500 5.0 9.0 9.0 9.0 7.0 6.0 0.1250
4.0 7.0 7.0 7.0 5.0 3.0 0.0625 3.0 7.0 5.0 7.0 5.0 5.0 0.0313 0.0
5.0 2.0 6.0 3.0 5.0 106 0.2500 7.0 9.0 6.0 9.0 7.0 5.0 0.1250 5.0
6.0 2.0 9.0 5.0 3.0 0.0625 4.0 6.0 0.0 9.0 4.0 2.0 0.0313 2.0 5.0
0.0 9.0 3.0 2.0 107 0.2500 4.0 7.0 9.0 3.0 3.0 0.1250 4.0 4.0 0.0
7.0 0.0 0.0 0.0625 4.0 0.0 0.0 6.0 0.0 0.0 0.0313 0.0 0.0 0.0 4.0
0.0 0.0 108 0.2500 0.0 7.0 9.0 6.0 3.0 0.1250 0.0 7.0 0.0 9.0 3.0
2.0 0.0625 0.0 6.0 0.0 9.0 0.0 2.0 0.0313 0.0 4.0 0.0 9.0 0.0 0.0
109 0.2500 9.0 9.0 6.5 9.0 9.0 7.5 0.1250 9.0 9.0 9.0 9.0 9.0 7.0
0.0625 9.0 7.0 5.5 9.0 7.5 8.0 0.0313 9.0 5.0 4.5 7.0 4.5 5.0 110
0.2500 9.0 8.0 0.0 9.0 8.0 4.0 0.1250 7.0 7.0 0.0 9.0 7.0 2.0
0.0625 7.0 4.0 0.0 9.0 7.0 0.0 0.0313 7.0 3.0 0.0 9.0 6.0 0.0 111
0.2500 7.0 5.0 9.0 4.0 6.0 3.0 0.1250 6.0 4.0 9.0 4.0 5.0 4.0
0.0625 3.0 3.0 4.0 4.0 4.0 3.0 0.0313 0.0 0.0 3.0 3.0 0.0 112
0.2500 3.0 7.0 9.0 7.0 5.0 0.1250 3.0 6.0 9.0 7.0 3.0 0.0625 3.0
3.0 9.0 7.0 0.0 0.0313 0.0 0.0 0.0 9.0 6.0 0.0 113 0.2500 7.0 6.0
0.0 9.0 9.0 0.0 0.1250 5.0 5.0 0.0 9.0 9.0 0.0 0.0625 4.0 5.0 0.0
9.0 6.0 0.0 0.0313 4.0 3.0 0.0 9.0 4.0 0.0 114 0.2500 8.0 9.0 4.5
9.0 4.5 4.5 0.1250 7.0 8.5 3.5 9.0 3.5 4.5 0.0625 7.0 6.5 4.5 9.0
3.5 4.5 0.0313 6.0 4.5 3.5 9.0 3.5 2.0 115 0.2500 5.0 9.0 6.0 9.0
6.0 4.0 0.1250 5.0 9.0 9.0 5.0 4.0 0.0625 4.0 6.0 0.0 9.0 3.0 3.0
0.0313 4.0 5.0 0.0 7.0 2.0 3.0 116 0.2500 5.0 7.0 8.0 9.0 6.0 4.0
0.1250 6.0 7.0 7.0 9.0 5.0 4.0 0.0625 5.0 6.0 6.0 9.0 3.0 2.0
0.0313 0.0 3.0 6.0 7.0 2.0 2.0 117 0.2500 0.0 6.0 9.0 9.0 0.0 3.0
0.1250 0.0 5.0 9.0 9.0 0.0 3.0 0.0625 0.0 2.0 7.0 7.0 0.0 0.0
0.0313 0.0 0.0 6.0 0.0 2.0 118 0.2500 6.0 0.0 0.0 7.0 3.0 3.0
0.1250 4.0 0.0 0.0 6.0 3.0 3.0 0.0625 0.0 0.0 0.0 4.0 0.0 1.0
0.0313 0.0 0.0 0.0 4.0 0.0 0.0 119 0.2500 9.0 8.0 1.0 9.0 4.5 5.5
0.1250 9.0 8.5 0.0 9.0 3.5 3.0 0.0625 9.0 7.0 0.0 8.0 3.0 2.0
0.0313 8.0 4.5 0.0 7.5 2.5 1.0 120 0.2500 9.0 9.0 3.5 9.0 7.5 4.0
0.1250 9.0 3.5 0.0 9.0 2.0 3.0 0.0625 8.0 2.5 0.0 9.0 0.0 1.0
0.0313 7.0 2.0 0.0 8.5 0.0 2.0 121 0.2500 6.0 8.0 5.0 9.0 6.0 7.0
0.1250 6.0 8.0 5.0 9.0 4.0 6.0 0.0625 5.0 4.0 9.0 4.0 4.0 0.0313
4.0 4.0 2.0 9.0 0.0 3.0 122 0.2500 7.0 8.0 3.0 9.0 6.0 3.0 0.1250
7.0 7.0 9.0 5.0 3.0 0.0625 7.0 7.0 9.0 3.0 2.0 0.0313 6.0 4.0 8.0
2.0 2.0 123 0.2500 9.0 9.0 9.0 9.0 8.0 3.0 0.1250 9.0 9.0 9.0
9.0 6.0 3.0 0.0625 9.0 5.0 9.0 7.0 6.0 2.0 0.0313 7.0 6.0 5.0 6.0
5.0 2.0 124 0.2500 8.0 6.0 3.0 7.0 5.0 5.0 0.1250 9.0 0.0 2.0 0.0
4.0 2.0 0.0625 5.0 0.0 0.0 0.0 0.0 0.0 0.0313 5.0 0.0 0.0 0.0 0.0
0.0 125 0.2500 7.0 9.0 9.0 9.0 9.0 7.0 0.1250 7.0 7.0 9.0 7.0 4.0
3.0 0.0625 4.0 6.0 4.0 7.0 4.0 2.0 0.0313 2.0 3.0 2.0 5.0 3.0 0.0
126 0.2500 7.0 2.0 0.0 7.0 3.0 4.0 0.1250 6.0 0.0 0.0 6.0 3.0 3.0
0.0625 3.0 0.0 0.0 4.0 0.0 3.0 0.0313 0.0 0.0 0.0 3.0 0.0 0.0 127
0.2500 9.0 4.0 0.0 7.0 3.0 4.0 0.1250 9.0 4.0 0.0 5.0 0.0 4.0
0.0625 7.0 2.0 0.0 3.0 0.0 2.0 0.0313 4.0 2.0 0.0 3.0 0.0 0.0 128
0.2500 9.0 4.0 3.0 9.0 6.0 3.0 0.1250 7.0 4.0 9.0 4.0 0.0 0.0625
7.0 4.0 0.0 7.0 3.0 0.0 0.0313 5.0 0.0 6.0 0.0 0.0 129 0.2500 9.0
9.0 9.0 9.0 7.0 2.0 0.1250 9.0 7.0 7.0 9.0 2.0 0.0 0.0625 9.0 5.0
7.0 0.0 0.0 0.0313 9.0 4.0 6.0 0.0 0.0 130 0.2500 4.0 6.0 7.0 6.0
3.0 6.0 0.1250 3.0 4.0 0.0 6.0 0.0 4.0 0.0625 2.0 2.0 5.0 0.0 4.0
0.0313 0.0 0.0 5.0 0.0 4.0 131 0.2500 4.0 4.0 0.0 2.0 2.0 5.0
0.1250 2.0 0.0 0.0 0.0 0.0 2.0 132 0.2500 6.0 3.0 0.0 9.0 0.0 4.0
0.1250 4.0 0.0 0.0 9.0 0.0 4.0 0.0625 4.0 0.0 0.0 9.0 0.0 2.0
0.0313 3.0 0.0 0.0 6.0 0.0 0.0 133 0.2500 9.0 3.0 1.0 6.0 3.0 4.0
0.1250 9.0 2.0 0.0 4.0 3.0 4.0 0.0625 6.0 0.0 0.0 4.0 3.0 2.0
0.0313 6.0 0.0 0.0 3.0 0.0 2.0 134 0.2500 2.0 3.0 2.0 0.0 2.0 135
0.2500 9.0 7.0 0.0 8.0 6.0 0.0 0.1250 7.0 7.0 0.0 9.0 5.0 0.0
0.0625 7.0 6.0 9.0 3.0 0.0 0.0313 7.0 5.0 6.0 0.0 0.0 136 0.2500
9.0 7.0 0.0 9.0 3.0 3.0 0.1250 7.0 6.0 0.0 9.0 3.0 3.0 0.0625 7.0
5.0 0.0 4.0 0.0 3.0 0.0313 7.0 0.0 0.0 3.0 0.0 2.0 137 0.2500 5.0
4.0 0.0 8.0 3.0 4.0 0.1250 3.0 2.0 0.0 5.0 0.0 1.0 0.0625 3.0 2.0
0.0 5.0 0.0 0.0 0.0313 3.0 3.0 0.0 4.0 0.0 0.0 138 0.2500 9.0 5.0
0.0 7.0 3.0 3.0 0.1250 9.0 3.0 0.0 6.0 0.0 3.0 0.0625 9.0 2.0 0.0
6.0 0.0 3.0 0.0313 7.0 2.0 0.0 5.0 0.0 3.0 139 0.2500 7.0 6.0 0.0
7.0 0.0 2.0 0.1250 7.0 5.0 0.0 7.0 0.0 0.0 0.0625 7.0 4.0 5.0 0.0
0.0 0.0313 6.0 2.0 4.0 0.0 0.0 140 0.2500 7.0 7.0 0.0 9.0 4.0 2.0
0.1250 7.0 9.0 0.0 9.0 4.0 0.0 0.0625 5.0 7.0 0.0 7.0 3.0 0.0
0.0313 5.0 4.0 0.0 4.0 2.0 0.0 141 0.2500 7.0 6.0 0.0 9.0 6.0 0.0
0.1250 7.0 6.0 0.0 8.0 5.0 0.0 0.0625 5.0 5.0 0.0 8.0 5.0 0.0
0.0313 5.0 4.0 0.0 7.0 4.0 0.0 142 0.2500 7.0 7.0 0.0 8.0 2.0 1.0
0.1250 7.0 6.0 0.0 9.0 0.0 0.0 0.0625 5.0 2.0 7.0 0.0 0.0 0.0313
4.0 0.0 6.0 0.0 0.0 143 0.2500 9.0 4.0 0.0 6.0 5.0 3.0 0.1250 9.0
4.0 0.0 6.0 0.0 3.0 0.0625 7.0 3.0 0.0 6.0 0.0 3.0 0.0313 5.0 0.0
0.0 5.0 0.0 1.0 144 0.2500 3.0 9.0 9.0 9.0 4.0 3.0 0.1250 1.0 9.0
9.0 9.0 2.0 3.0 0.0625 0.0 3.0 7.0 9.0 0.0 0.0 0.0313 0.0 3.0 7.0
6.0 0.0 0.0 145 0.2500 7.0 9.0 9.0 9.0 5.0 2.0 0.1250 7.0 7.0 9.0
9.0 5.0 0.0 0.0625 6.0 5.0 6.0 2.0 0.0 0.0313 6.0 4.0 4.0 0.0 0.0
146 0.2500 9.0 7.0 0.0 9.0 4.0 2.0 0.1250 9.0 6.0 0.0 6.0 3.0 0.0
0.0625 9.0 6.0 0.0 6.0 0.0 0.0 0.0313 9.0 4.0 0.0 4.0 0.0 0.0 147
0.2500 9.0 7.0 0.0 9.0 2.0 5.0 0.1250 9.0 7.0 9.0 0.0 4.0 0.0625
7.0 4.0 9.0 0.0 3.0 0.0313 5.0 4.0 7.0 0.0 2.0 148 0.2500 9.0 7.0
5.0 9.0 4.0 0.0 0.1250 9.0 6.0 0.0 9.0 4.0 0.0 0.0625 7.0 4.0 7.0
3.0 0.0 0.0313 6.0 4.0 0.0 7.0 0.0 0.0 149 0.2500 7.0 4.0 0.0 7.0
3.0 0.0 0.1250 6.0 7.0 0.0 7.0 3.0 0.0 0.0625 3.0 4.0 0.0 7.0 2.0
0.0 0.0313 2.0 3.0 0.0 5.0 0.0 0.0 150 0.2500 9.0 9.0 9.0 9.0 2.0
5.0 0.1250 9.0 9.0 9.0 9.0 2.0 3.0 0.0625 7.0 9.0 9.0 2.0 2.0
0.0313 6.0 9.0 6.0 0.0 0.0 151 0.2500 9.0 8.0 7.0 9.0 6.0 9.0
0.1250 9.0 6.0 9.0 8.0 8.0 0.0625 5.0 2.0 7.0 9.0 2.0 9.0 0.0313
3.0 0.0 6.0 0.0 6.0 152 0.2500 0.0 0.0 0.0 3.0 0.0 3.0 0.1250 0.0
0.0 0.0 3.0 0.0 2.0 0.0625 0.0 0.0 0.0 3.0 0.0 0.0 153 0.2500 0.0
3.0 0.0 5.0 0.0 4.0 0.1250 0.0 0.0 0.0 4.0 0.0 2.0 0.0625 0.0 0.0
0.0 3.0 0.0 2.0 154 0.2500 7.0 6.0 9.0 9.0 6.0 8.0 0.1250 7.0 4.0
9.0 8.0 5.0 9.0 0.0625 4.0 3.0 6.0 7.0 4.0 8.0 0.0313 3.0 2.0 4.0
6.0 2.0 9.0 155 0.2500 4.0 0.0 0.0 0.0 3.0 0.1250 4.0 0.0 0.0 0.0
0.0 1.0 0.0625 4.0 0.0 0.0 0.0 0.0 0.0 0.0313 4.0 0.0 0.0 0.0 0.0
0.0 156 0.2500 0.0 0.0 0.0 0.0 0.0 3.0 157 0.2500 0.0 0.0 0.0 0.0
0.0 158 0.2500 9.0 9.0 9.0 9.0 9.0 7.0 0.1250 9.0 9.0 9.0 9.0 6.0
9.0 0.0625 9.0 9.0 9.0 9.0 5.0 6.0 0.0313 9.0 9.0 5.0 9.0 4.0 6.0
159 0.2500 7.0 4.0 9.0 6.0 8.0 0.1250 5.0 3.0 0.0 6.0 3.0 2.0
0.0625 4.0 0.0 0.0 3.0 3.0 0.0 0.0313 2.0 0.0 0.0 0.0 0.0 160
0.2500 4.0 9.0 3.0 7.0 8.0 6.0 0.1250 2.0 6.0 3.0 6.0 5.0 5.0
0.0625 0.0 3.0 3.0 6.0 2.0 3.0 0.0313 0.0 0.0 3.0 5.0 0.0 3.0 161
0.2500 4.0 6.0 3.0 9.0 9.0 4.0 0.1250 2.0 5.0 0.0 7.0 6.0 3.0
0.0625 0.0 4.0 0.0 7.0 2.0 0.0313 0.0 3.0 0.0 7.0 2.0 0.0 162
0.2500 8.0 9.0 9.0 9.0 3.0 7.0 0.1250 8.0 6.0 9.0 7.0 3.0 6.0
0.0625 7.0 6.0 7.0 3.0 3.0 0.0313 6.0 5.0 7.0 0.0 2.0 163 0.2500
9.0 9.0 9.0 9.0 7.0 7.0 0.1250 9.0 9.0 9.0 9.0 6.0 6.0 0.0625 9.0
7.0 9.0 3.0 3.0 0.0313 9.0 6.0 9.0 2.0 2.0 164 0.2500 9.0 9.0 7.0
9.0 6.0 6.0 0.1250 9.0 6.0 3.0 9.0 5.0 3.0 0.0625 7.0 5.0 0.0 9.0
4.0 2.0 0.0313 6.0 3.0 0.0 8.0 4.0 2.0 165 0.2500 9.0 9.0 3.0 9.0
7.0 3.0 0.1250 9.0 9.0 0.0 9.0 4.0 1.0 0.0625 9.0 7.0 9.0 5.0 1.0
0.0313 9.0 6.0 0.0 9.0 4.0 0.0 166 0.2500 4.0 9.0 0.0 9.0 6.0 3.0
0.1250 2.0 6.0 0.0 9.0 5.0 3.0 0.0625 2.0 2.0 0.0 9.0 4.0 0.0
0.0313 2.0 2.0 0.0 9.0 2.0 0.0 167 0.2500 9.0 9.0 5.0 9.0 7.0 4.0
0.1250 9.0 9.0 3.0 9.0 6.0 4.0 0.0625 9.0 9.0 0.0 9.0 5.0 4.0
0.0313 9.0 7.0 0.0 9.0 4.0 4.0 168 0.2500 0.0 0.0 7.0 2.0 2.0
0.1250 0.0 0.0 0.0 6.0 0.0 0.0 0.0625 0.0 0.0 0.0 6.0 0.0 0.0
0.0313 0.0 0.0 0.0 6.0 0.0 0.0 169 0.2500 2.0 2.0 7.0 3.0 2.0
0.1250 0.0 0.0 0.0 6.0 0.0 0.0 0.0625 0.0 0.0 6.0 0.0 0.0 0.0313
0.0 0.0 0.0 5.0 0.0 0.0 170 0.2500 9.0 9.0 9.0 9.0 9.0 0.1250 9.0
9.0 9.0 8.0 6.0 0.0625 9.0 9.0 9.0 9.0 8.0 0.0313 9.0 9.0 9.0 5.0
4.0 171 0.2500 9.0 9.0 9.0 9.0 9.0 7.0 0.1250 9.0 9.0 9.0 9.0 8.0
6.0 0.0625 9.0 9.0 9.0 9.0 7.0 6.0 0.0313 8.0 3.0 9.0 9.0 6.0 5.0
172 0.2500 9.0 9.0 9.0 9.0 9.0 9.0 0.1250 9.0 8.0 9.0 9.0 9.0 9.0
0.0625 9.0 7.0 6.0 9.0 6.0 7.0 0.0313 6.0 5.0 9.0 6.0 6.0
EXAMPLE 40
[0725] Rice Tolerance to Post-Transplant Applications and
Postemergence Weed Control Under Flooded Paddy Conditions
[0726] Plastic containers containing weeds which are 3 to 5 cm tall
and rice seedlings at the 1.5 to 2.5 leaf stage are flooded with
water. The water is maintained at 1.5 to 3 cm above the soil
surface for the duration of the experiment. Test compounds are
applied as aqueous/ acetone mixtures 50/50 v/v directly into the
flood water to provide the equivalent of about 0.0313 to 0.500
kg/ha of active ingredient. The treated containers are placed on
greenhouse benches and cared for in accordance with conventional
greenhouse procedures. Three to four weeks after treatment, the
test is terminated and each container is examined and herbicidal
effect rated according to the rating system provided in Example 37.
The results are summarized in Table IV. The compounds evaluated are
reported by compound number given in Example 37.
23TABLE IV Paddy Conditions - Post Transplant Rice Postemergence
Weeds E O C C C M S R H Y Y O A Y O P P O G S Compound Rate R I S V
P A Number (kg/ha) C R E A Y T 1 0.5000 5.5 8.5 4.0 5.5 0.0 4.0
0.2500 3.5 6.5 1.0 5.0 0.0 3.0 0.1250 3.0 5.5 0.0 4.5 0.0 2.5
0.0625 2.0 3.5 0.0 4.5 0.0 2.5 0.0313 1.0 1.0 0.0 4.0 0.0 1.5 2
0.5000 4.5 4.0 0.0 9.0 1.0 2.5 0.2500 4.0 1.0 0.0 9.0 0.0 1.5
0.1250 3.5 0.0 0.0 5.5 0.0 0.5 0.0625 1.0 0.0 0.0 4.5 0.0 0.0
0.0313 1.0 0.0 0.0 2.0 0.0 0.0 3 0.5000 2.0 0.5 0.0 5.5 0.0 2.0
0.2500 1.0 0.0 0.0 4.5 0.0 1.0 0.1250 0.0 0.0 0.0 4.5 0.0 1.0
0.0625 0.0 0.0 0.0 1.0 0.0 0.0 4 0.5000 5.0 9.0 0.0 8.0 0.0 3.0
0.2500 4.0 6.5 0.0 5.5 0.0 2.5 0.1250 3.5 4.5 0.0 4.0 0.0 2.0
0.0625 2.0 2.0 0.0 3.5 0.0 1.5 0.0313 1.0 0.0 0.0 1.0 0.0 0.0 5
0.5000 2.0 0.0 0.5 4.0 0.0 1.0 0.2500 1.0 0.0 0.0 2.0 0.0 0.5
0.1250 0.5 0.0 0.0 1.0 0.0 0.5 6 0.5000 3.5 3.5 0.0 4.5 0.0 0.0
0.2500 3.5 3.0 0.0 4.5 0.0 0.0 0.1250 1.0 2.0 0.0 4.0 0.0 0.0
0.0625 0.0 1.0 0.0 4.0 0.0 0.0 0.0313 0.0 0.0 0.0 1.0 0.0 0.0 7
0.2500 9.0 9.0 8.0 9.0 8.5 9.0 0.1250 9.0 9.0 7.5 9.0 7.5 7.0
0.0625 8.5 9.0 7.0 9.0 5.5 6.5 0.0313 7.0 8.5 3.0 9.0 3.0 5.0 8
0.2500 8.5 4.0 0.0 9.0 0.0 6.0 0.1250 7.5 0.0 0.0 9.0 0.0 5.0
0.0625 6.5 0.0 0.0 9.0 0.0 3.5 0.0313 6.5 0.0 0.0 9.0 0.0 2.5 9
0.2500 7.0 6.0 7.0 9.0 2.0 9.0 0.1250 4.0 4.0 2.0 9.0 1.0 9.0
0.0625 2.0 2.0 0.0 9.0 0.0 8.0 0.0313 0.0 0.0 0.0 9.0 0.0 7.0 10
0.2500 2.0 4.0 0.0 9.0 0.0 7.0 0.1250 2.0 2.0 0.0 9.0 0.0 6.0
0.0625 1.0 0.0 0.0 9.0 0.0 4.0 0.0313 0.0 0.0 0.0 9.0 0.0 3.0 11
0.2500 3.0 0.0 0.0 7.0 0.0 3.0 0.1250 2.0 0.0 0.0 4.0 0.0 3.0
0.0625 2.0 0.0 0.0 1.0 0.0 2.0 0.0313 1.0 0.0 0.0 0.0 0.0 2.0 12
0.2500 9.0 0.0 6.0 9.0 0.0 7.0 0.1250 8.5 1.0 1.0 9.0 4.0 5.5
0.0625 9.0 0.0 3.0 9.0 1.0 3.5 0.0313 5.0 0.0 1.0 9.0 0.0 3.0 13
0.2500 9.0 1.0 0.0 9.0 0.0 5.0 0.1250 8.0 0.5 0.0 9.0 0.0 3.0
0.0625 7.0 0.0 0.0 9.0 0.0 2.5 0.0313 5.5 0.0 0.0 9.0 0.0 1.5 14
0.2500 7.0 4.5 0.0 4.5 0.0 0.0 0.1250 3.8 6.8 1.5 6.8 0.0 0.5
0.0625 2.3 5.8 0.0 6.8 0.0 0.3 0.0313 0.8 4.0 0.0 6.8 0.0 0.0 15
0.2500 9.0 7.0 0.0 9.0 0.0 3.0 0.1250 9.0 6.0 0.0 9.0 0.0 3.0
0.0625 9.0 2.0 0.0 9.0 0.0 2.0 0.0313 6.0 2.0 0.0 9.0 0.0 0.0 16
0.2500 0.0 9.0 0.0 3.0 0.0 0.0 0.1250 0.0 4.0 0.0 9.0 0.0 0.0
0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 17
0.2500 9.0 9.0 9.0 9.0 4.0 9.0 0.1250 9.0 6.0 9.0 9.0 4.0 9.0
0.0625 9.0 0.0 9.0 9.0 0.0 6.0 0.0313 4.0 0.0 9.0 9.0 0.0 4.0 18
0.4630 7.0 0.0 4.0 9.0 6.0 3.0 0.2310 7.0 0.0 0.0 9.0 0.0 3.0
0.1160 7.0 0.0 0.0 9.0 0.0 3.0 19 0.4630 9.0 0.0 4.0 9.0 3.0 3.0
0.2310 7.0 0.0 4.0 9.0 3.0 3.0 0.1160 7.0 0.0 4.0 9.0 0.0 3.0 20
0.4630 7.0 0.0 5.0 9.0 3.0 2.0 0.2310 7.0 0.0 5.0 9.0 0.0 2.0
0.1160 7.0 0.0 5.0 9.0 0.0 2.0 21 0.4630 5.0 0.0 0.0 0.0 0.0 0.0
0.2310 4.0 0.0 0.0 0.0 0.0 0.0 0.1160 2.0 0.0 0.0 0.0 0.0 0.0 22
0.4630 9.0 5.0 4.0 9.0 5.0 7.0 0.2310 9.0 0.0 4.0 9.0 4.0 6.0
0.1160 6.0 0.0 4.0 9.0 4.0 3.0 23 0.4630 4.0 0.0 0.0 9.0 3.0 5.0
0.2310 4.0 0.0 0.0 9.0 0.0 4.0 0.1160 4.0 0.0 0.0 9.0 0.0 4.0 24
0.2500 9.0 0.0 9.0 0.0 0.0 0.1250 9.0 0.0 9.0 0.0 0.0 0.0625 9.0
0.0 9.0 0.0 0.0 0.0313 4.0 0.0 0.0 0.0 0.0 25 0.2500 9.0 0.0 9.0
5.0 5.0 0.1250 7.0 0.0 9.0 5.0 4.0 0.0625 6.0 0.0 9.0 0.0 4.0
0.0313 4.0 0.0 9.0 0.0 3.0 26 0.2500 9.0 9.0 9.0 7.0 2.0 0.1250 9.0
7.0 9.0 5.0 1.0 0.0625 9.0 4.0 9.0 4.0 0.0 0.0313 7.0 2.0 9.0 0.0
0.0 27 0.2500 9.0 9.0 9.0 9.0 4.0 4.0 0.1250 9.0 6.0 0.0 9.0 4.0
4.0 0.0625 7.0 4.0 0.0 9.0 0.0 2.0 0.0313 6.0 3.0 0.0 9.0 0.0 1.0
28 0.2500 9.0 9.0 0.0 9.0 0.0 1.0 0.1250 7.0 9.0 0.0 9.0 0.0 0.0
0.0625 4.0 9.0 0.0 9.0 0.0 0.0 0.0313 0.0 9.0 0.0 9.0 0.0 0.0 29
0.2500 7.0 0.0 0.0 0.0 0.0 3.0 0.1250 7.0 0.0 0.0 0.0 0.0 2.0
0.0625 7.0 0.0 0.0 0.0 0.0 1.0 0.0313 4.0 0.0 0.0 0.0 0.0 0.0 30
0.2500 0.0 4.5 0.0 4.5 2.0 0.0 0.1250 0.0 2.0 0.0 1.5 0.0 0.0 31
0.2500 5.0 2.5 0.0 2.5 0.0 0.0 0.1250 2.0 0.0 0.0 0.0 0.0 0.0
0.0625 1.0 0.0 0.0 0.0 0.0 0.0 32 0.2500 6.0 0.0 0.0 0.0 0.0 0.1250
3.0 0.0 0.0 0.0 0.0 33 0.2500 0.0 0.0 0.0 0.0 0.0 34 0.2500 9.0 0.0
0.0 0.0 6.0 0.1250 4.0 0.0 0.0 0.0 4.0 0.0625 4.0 0.0 0.0 0.0 3.0
0.0313 3.0 0.0 0.0 0.0 3.0 35 0.2500 6.0 0.0 0.0 3.0 3.0 0.1250 3.0
0.0 0.0 0.0 2.0 36 0.2500 9.0 9.0 4.0 9.0 5.0 0.1250 7.0 5.0 2.0
3.0 3.0 0.0625 6.0 5.0 0.0 0.0 3.0 0.0313 4.0 0.0 0.0 0.0 3.0 37
0.2500 7.0 0.0 0.0 3.0 3.0 0.1250 7.0 0.0 0.0 0.0 0.0 0.0625 6.0
0.0 0.0 0.0 0.0 0.0313 4.0 0.0 0.0 0.0 0.0 38 0.2500 7.0 5.0 3.0
9.0 9.0 7.0 0.1250 4.0 5.0 0.0 9.0 4.0 5.0 0.0625 2.0 3.0 0.0 9.0
3.0 5.0 0.0313 0.0 3.0 0.0 9.0 0.0 2.0 39 0.2500 3.0 0.0 0.0 9.0
4.0 3.0 0.1250 2.0 0.0 0.0 9.0 0.0 2.0 0.0625 0.0 0.0 0.0 9.0 0.0
0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 40 0.2500 9.0 0.0 6.0 9.0 0.0
3.0 0.1250 5.0 0.0 0.0 9.0 0.0 3.0 0.0625 5.0 0.0 0.0 9.0 0.0 3.0
0.0313 5.0 0.0 0.0 9.0 0.0 2.0 41 0.2500 7.0 4.0 7.0 9.0 6.0 5.0
0.1250 6.0 0.0 2.0 9.0 0.0 5.0 0.0625 4.0 0.0 0.0 9.0 0.0 5.0
0.0313 3.0 0.0 0.0 6.0 0.0 4.0 42 0.2500 6.0 0.0 0.0 9.0 3.0 0.0
0.1250 5.0 0.0 0.0 9.0 0.0 0.0 0.0625 5.0 0.0 0.0 9.0 0.0 0.0
0.0313 5.0 0.0 0.0 7.0 0.0 0.0 43 0.2500 9.0 5.0 9.0 9.0 9.0 6.0
0.1250 7.0 4.0 8.0 9.0 7.0 4.0 0.0825 6.0 2.0 5.0 9.0 7.0 3.0
0.0313 5.0 0.0 5.0 9.0 7.0 2.0 44 0.2500 8.0 9.0 0.0 9.0 5.0 0.1250
7.0 6.0 0.0 7.0 3.0 0.0625 6.0 6.0 0.0 4.0 3.0 0.0313 6.0 5.0 0.0
4.0 0.0 45 0.2500 7.0 7.0 0.0 9.0 4.0 3.0 0.1250 7.0 7.0 9.0 0.0
2.0 0.0625 4.0 3.0 0.0 7.0 0.0 2.0 0.0313 3.0 0.0 0.0 7.0 0.0 3.0
46 0.2500 4.0 0.0 6.0 7.0 3.0 3.0 0.1250 0.0 0.0 0.0 6.0 0.0 2.0
0.0625 0.0 0.0 0.0 4.0 0.0 2.0 0.0313 0.0 0.0 0.0 3.0 0.0 0.0 47
0.2500 7.0 6.0 0.0 9.0 7.0 3.0 0.1250 4.0 4.0 0.0 9.0 4.0 0.0
0.0625 2.0 0.0 0.0 6.0 0.0 0.0 0.0313 0.0 0.0 0.0 5.0 0.0 0.0 48
0.2500 6.0 5.0 0.0 6.0 6.0 6.0 0.1250 3.0 2.0 0.0 3.0 3.0 4.0 49
0.2500 7.0 7.0 4.0 9.0 7.0 7.0 0.1250 5.0 2.0 9.0 6.0 7.0 0.0625
2.0 0.0 3.0 9.0 4.0 5.0 0.0313 0.0 0.0 2.0 9.0 2.0 5.0 50 0.2500
7.0 0.0 0.0 7.0 3.0 1.0 0.1250 7.0 0.0 0.0 3.0 3.0 0.0 0.0625 7.0
0.0 0.0 0.0 2.0 0.0 0.0313 4.0 0.0 0.0 0.0 2.0 0.0 51 0.2500 0.0
6.0 0.0 4.0 0.0 0.0 0.1250 0.0 3.0 0.0 4.0 0.0 0.0 0.0625 0.0 2.0
0.0 3.0 0.0 0.0 52 0.2500 0.0 2.0 0.0 4.0 0.0 0.0 53 0.2500 3.0 9.0
0.0 9.0 0.0 3.0 0.1250 2.0 9.0 0.0 9.0 0.0 2.0 0.0625 0.0 2.0 0.0
2.0 0.0 0.0 0.0313 0.0 2.0 0.0 2.0 0.0 0.0 54 0.2500 9.0 4.0 4.0
6.0 2.0 4.0 0.1250 7.0 4.0 0.0 6.0 0.0 3.0 0.0625 5.0 4.0 0.0 0.0
0.0 2.0 0.0313 5.0 0.0 0.0 0.0 0.0 0.0 55 0.2500 7.0 9.0 0.0 9.0
0.0 4.0 0.1250 7.0 9.0 0.0 9.0 0.0 1.0 0.0625 7.0 9.0 0.0 9.0 0.0
1.0 0.0313 7.0 9.0 0.0 9.0 0.0 0.0 56 0.2500 5.0 0.0 0.0 9.0 0.0
2.0 0.1250 3.0 0.0 0.0 9.0 0.0 0.0 0.0625 0.0 0.0 0.0 6.0 0.0 0.0
0.0313 0.0 0.0 0.0 6.0 0.0 0.0 57 0.2500 5.0 9.0 3.0 9.0 6.0 4.0
0.1250 2.0 9.0 0.0 9.0 0.0 0.0 0.0625 2.0 9.0 0.0 9.0 0.0 0.0
0.0313 0.0 0.0 0.0 9.0 0.0 0.0 58 0.2500 9.0 3.0 5.0 9.0 4.0 5.0
0.1250 7.0 2.0 5.0 3.0 0.0 4.0 0.0625 7.0 0.0 5.0 0.0 0.0 4.0
0.0313 7.0 0.0 5.0 0.0 0.0 4.0 59 0.2500 7.0 9.0 7.0 9.0 3.0 2.0
0.1250 5.0 0.0 0.0 0.0 0.0 2.0 0.0625 4.0 0.0 0.0 0.0 0.0 0.0 60
0.2500 9.0 6.0 4.0 9.0 9.0 5.0 0.1250 9.0 6.0 4.0 9.0 9.0 5.0
0.0625 9.0 3.0 2.0 9.0 4.0 4.0 0.0313 7.0 3.0 2.0 9.0 3.0 4.0 61
0.2500 0.0 0.0 0.0 0.0 0.0 0.0 62 0.2500 5.0 9.0 0.0 9.0 6.0 4.0
0.1250 2.0 9.0 0.0 9.0 3.0 3.0 0.0625 0.0 2.0 0.0 9.0 0.0 3.0
0.0313 0.0 0.0 0.0 4.0 0.0 2.0 63 0.2500 5.0 7.0 0.0 9.0 9.0 3.0
0.1250 5.0 7.0 0.0 9.0 9.0 3.0 0.0625 0.0 6.0 0.0 9.0 7.0 3.0
0.0313 0.0 2.0 0.0 9.0 4.0 3.0 64 0.2500 9.0 7.0 0.0 9.0 8.0 6.0
0.1250 6.0 2.0 0.0 9.0 5.0 5.0 0.0625 6.0 2.0 0.0 9.0 3.0 4.0
0.0313 5.0 0.0 0.0 7.0 0.0 3.0 65 0.2500 7.0 8.0 0.0 9.0 7.0 6.0
0.1250 6.0 7.0 0.0 9.0 5.0 6.0 0.0625 5.0 7.0 0.0 9.0 4.0 3.0
0.0313 5.0 6.0 0.0 9.0 2.0 2.0 66 0.2500 9.0 7.0 4.0 9.0 4.0 3.0
0.1250 9.0 7.0 4.0 9.0 4.0 3.0 0.0625 7.0 6.0 0.0 9.0 4.0 2.0
0.0313 7.0 6.0 0.0 9.0 3.0 2.0 67 0.2500 5.0 8.0 3.0 9.0 6.0 6.0
0.1250 5.0 5.0 3.0 9.0 4.0 4.0 0.0625 4.0 5.0 3.0 9.0 4.0 3.0
0.0313 0.0 5.0 0.0 9.0 0.0 2.0 68 0.2500 7.0 8.0 0.0 9.0 3.0 4.0
0.1250 7.0 5.0 0.0 9.0 0.0 2.0 0.0625 5.0 0.0 0.0 9.0 0.0 0.0
0.0313 0.0 0.0 0.0 3.0 0.0 0.0 69 0.2500 7.0 3.0 9.0 3.0 3.0 0.1250
5.0 3.0 9.0 3.0 2.0 0.0625 4.0 3.0 3.0 0.0 2.0 0.0313 0.0 3.0 3.0
0.0 0.0 70 0.2500 0.0 2.0 3.0 4.0 2.0 0.1250 0.0 2.0 0.0 4.0 2.0
0.0625 0.0 2.0 0.0 4.0 0.0 0.0313 0.0 0.0 0.0 4.0 0.0 71 0.2500 7.0
7.0 3.0 0.0 4.0 0.1250 0.0 3.0 3.0 0.0 4.0 72 0.2500 9.0 9.0 9.0
4.0 3.0 0.1250 9.0 7.0 9.0 4.0 3.0 0.0625 9.0 6.0 0.0 4.0 2.0
0.0313 9.0 6.0 0.0 4.0 1.0 73 0.2500 7.0 6.0 4.0 4.0 6.0 0.1250 3.0
0.0 2.0 3.0 5.0 74 0.2500 9.0 0.0 9.0 9.0 3.0 0.1250 9.0 0.0 5.0
3.0 2.0 0.0625 9.0 0.0 5.0 3.0 0.0 0.0313 7.0 0.0 0.0 3.0 0.0 75
0.2500 9.0 6.0 3.0 3.0 2.0 0.1250 9.0 6.0 3.0 0.0 1.0 0.0625 6.0
0.0 3.0 0.0 0.0 0.0313 6.0 0.0 2.0 0.0 0.0 76 0.2500 9.0 6.0 3.0
4.0 4.0 0.1250 9.0 0.0 2.0 4.0 3.0 0.0625 7.0 0.0 2.0 0.0 2.0
0.0313 4.0 0.0 2.0 0.0 2.0 77 0.2500 9.0 0.0 4.0 0.0 3.0 0.1250 9.0
0.0 0.0 0.0 3.0 0.0625 9.0 0.0 0.0 0.0 2.0 0.0313 9.0 0.0 0.0 0.0
2.0 78 0.2500 9.0 9.0 9.0 4.0 1.0 0.1250 9.0 6.0 7.0 2.0 0.0 0.0625
7.0 5.0 6.0 0.0 0.0 0.0313 7.0 5.0 6.0 0.0 0.0 79 0.2500 8.0 6.0
9.0 4.0 3.0 0.1250 7.0 2.0 0.0 4.0 3.0 0.0625 6.0 0.0 0.0 0.0 2.0
0.0313 5.0 0.0 0.0 0.0 0.0 80 0.2500 9.0 7.0 4.0 0.0 2.0 0.1250 9.0
7.0 3.0 0.0 0.0 0.0625 9.0 7.0 3.0 0.0 0.0 0.0313 9.0 5.0 3.0 0.0
0.0 81 0.2500 3.0 5.0 0.0 0.0 0.0 0.1250 3.0 5.0 0.0 0.0 0.0 0.0625
0.0 4.0 0.0 0.0 0.0 82 0.2500 9.0 3.0 4.0 7.0 3.0 0.1250 6.0 3.0
2.0 4.0 3.0 0.0625 4.0 0.0 0.0 4.0 0.0 0.0313 4.0 0.0 0.0 4.0 0.0
83 0.2500 7.0 7.0 5.0 9.0 9.0 6.0 0.1250 7.0 6.0 3.0 9.0 7.0 5.0
0.0625 6.0 6.0 9.0 7.0 3.0 0.0313 5.0 5.0 0.0 9.0 7.0 3.0 84 0.2500
9.0 9.0 9.0 9.0 9.0 7.0 0.1250 7.0 9.0 9.0 9.0 7.0 6.0 0.0625 5.0
7.0 3.0 9.0 6.0 4.0 0.0313 4.0 3.0 0.0 9.0 2.0 3.0 85 0.2500 9.0
9.0 9.0 9.0 9.0 5.0 0.1250 7.0 9.0 2.0 9.0 9.0 4.0 0.0625 5.0 7.0
2.0 9.0 3.0 4.0 0.0313 4.0 3.0 0.0 9.0 3.0 3.0 86 0.2500 9.0 9.0
9.0 9.0 9.0 5.0 0.1250 9.0 8.0 3.0 9.0 9.0 4.0 0.0625 6.0 7.0 0.0
9.0 9.0 4.0 0.0313 5.0 3.0 0.0 9.0 5.0 3.0 87 0.5000 3.0 7.0 5.0
9.0 7.0 6.0 0.2500 3.0 5.0 5.0 9.0 5.0 4.0 0.1250 2.0 5.0 5.0 9.0
4.0 3.0 0.0625 0.0 5.0 0.0 9.0 4.0 3.0 0.0313 0.0 5.0 0.0 9.0 0.0
2.0 88 0.2500 7.0 0.0 7.0 9.0 9.0 4.0 0.1250 6.0 0.0 7.0 9.0 9.0
4.0 0.0625 6.0 0.0 5.0 9.0 9.0 3.0 0.0313 6.0 0.0 3.0 9.0 6.0 2.0
89 0.2500 6.0 4.0 6.0 9.0 9.0 6.0 0.1250 5.0 2.0 4.0 9.0 9.0 5.0
0.0625 4.0 0.0 0.0 9.0 5.0 4.0 0.0313 3.0 0.0 0.0 9.0 4.0 2.0 90
0.2500 3.0 3.0 3.0 9.0 9.0 3.0 0.1250 0.0 1.0 0.0 9.0 9.0 1.0
0.0625 0.0 0.0 0.0 9.0 6.0 0.0 0.0313 0.0 0.0 0.0 9.0 4.0 0.0 91
0.2500 4.0 0.0 0.0 9.0 0.0 2.0 0.1250 2.0 0.0 0.0 9.0 0.0 0.0
0.0625 0.0 0.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 92
0.2500 3.0 7.0 9.0 9.0 9.0 3.0 0.1250 2.0 5.0 9.0 9.0 4.0 3.0
0.0625 0.0 3.0 9.0 9.0 0.0 2.0 0.0313 0.0 3.0 9.0 9.0 0.0 1.0 93
0.2500 7.0 0.0 9.0 9.0 9.0 3.0 0.1250 4.0 0.0 5.0 9.0 3.0 0.0
0.0625 3.0 0.0 0.0 9.0 0.0 0.0 0.0313 0.0 0.0 0.0 9.0 0.0 0.0 94
0.2500 7.0 4.0 9.0 9.0 9.0 3.0 0.1250 2.0 4.0 6.0 9.0 5.0 3.0
0.0625 0.0 3.0 9.0 0.0 2.0 0.0313 0.0 0.0 9.0 0.0 0.0 95 0.2500 3.0
7.0 3.0 9.0 8.0 0.1250 3.0 7.0 0.0 9.0 8.0 0.0625 0.0 4.0 0.0 5.0
4.0 0.0313 0.0 4.0 0.0 5.0 3.0 96 0.2500 3.0 6.0 0.0 3.0 5.0 0.1250
0.0 6.0 0.0 3.0 4.0 0.0625 0.0 5.0 0.0 2.0 4.0 0.0313 0.0 0.0 0.0
2.0 3.0 97 0.2500 3.0 4.0 3.0 9.0 5.0 0.1250 2.0 3.0 0.0 9.0 5.0
0.0625 0.0 0.0 0.0 9.0 4.0 0.0313 0.0 0.0 0.0 9.0 1.0 98 0.2500 3.0
9.0 4.0 9.0 7.0 0.1250 1.0 9.0 4.0 9.0 7.0 0.0625 0.0 9.0 3.0 9.0
6.0 0.0313 0.0 9.0 2.0 9.0 2.0 99 0.5000 4.0 0.0 0.0 9.0 4.0 4.0
0.2500 0.0 0.0 0.0 9.0 4.0 4.0 0.1250 0.0 0.0 0.0 9.0 3.0 4.0
0.0625 0.0 0.0 0.0 9.0 0.0 2.0 0.0313 0.0 0.0 0.0 9.0 0.0 2.0 100
0.5000 4.0 9.0 9.0 6.0 4.0 0.2500 3.0 4.0 0.0 9.0 4.0 3.0 0.1250
0.0 0.0 0.0 9.0 0.0 3.0 0.0625 0.0 0.0 0.0 9.0 0.0 3.0 0.0313 0.0
0.0 0.0 9.0 0.0 3.0 101 0.5000 0.0 4.0 0.0 9.0 4.0 3.0 0.2500 0.0
3.0 0.0 9.0 2.0 0.0 0.1250 0.0 0.0 0.0 7.0 0.0 0.0 0.0625 0.0 0.0
0.0 5.0 0.0 0.0 0.0313 0.0 0.0 0.0 5.0 0.0 0.0 102 0.5000 2.0 6.0
0.0 4.0 0.0 4.0 0.2500 0.0 2.0 0.0 0.0 0.0 2.0 103 0.2500 6.0 9.0
6.0 9.0 9.0 6.0 0.1250 5.0 9.0 6.0 9.0 9.0 5.0 0.0625 4.0 6.0 5.0
7.0 9.0 5.0 0.0313 4.0 4.0 5.0 5.0 7.0 4.0 104 0.2500 6.0 9.0 0.0
9.0 9.0 6.0 0.1250 6.0 9.0 0.0 9.0 9.0 7.0 0.0625 5.0 9.0 9.0 9.0
5.0 0.0313 4.0 5.0 0.0 7.0 6.0 3.0 105 0.2500 5.0 9.0 9.0 9.0 7.0
6.0 0.1250 4.0 7.0 7.0 7.0 5.0 3.0 0.0625 3.0 7.0 5.0 7.0 5.0 5.0
0.0313 0.0 5.0 2.0 6.0 3.0 5.0 109 0.2500 9.0 7.0 7.0 9.0 0.0 8.0
0.1250 7.0 4.0 9.0 0.0 4.0 0.0625 2.0 2.0 0.0 4.0 0.0 2.0 0.0313
2.0 0.0 0.0 2.0 0.0 2.0 114 0.2500 0.0 7.0 0.0 9.0 0.0 4.0 0.1250
0.0 4.0 0.0 9.0 0.0 4.0 0.0625 0.0 0.0 0.0 8.0 0.0 1.0 0.0313 0.0
0.0 0.0 6.0 0.0 1.0 119 0.2500 4.0 9.0 9.0 0.0 3.0 0.1250 4.0 6.0
0.0 8.0 0.0 2.0 0.0625 2.0 0.0 7.0 0.0 2.0 0.0313 0.0 2.0 0.0 4.0
0.0 2.0
* * * * *