U.S. patent application number 11/461491 was filed with the patent office on 2007-08-23 for tricyclic benzoylpyrazole derivatives.
Invention is credited to Ernst Baumann, Steffen Kudis, Klaus Langemann, Guido Mayer, Ulf Misslitz, Ulf Neidlein, Martina Otten, Wolfgang von Deyn, Helmut Walter, Karl-Otto Westphalen, Matthias Witschel.
Application Number | 20070197393 11/461491 |
Document ID | / |
Family ID | 7900849 |
Filed Date | 2007-08-23 |
United States Patent
Application |
20070197393 |
Kind Code |
A1 |
Witschel; Matthias ; et
al. |
August 23, 2007 |
TRICYCLIC BENZOYLPYRAZOLE DERIVATIVES
Abstract
Tricyclic benzoylpyrazole derivatives of the formula I ##STR1##
where: X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2,
CR.sup.6R.sup.7, NR.sup.8 or a bond; Y together with the two
carbons to which it is attached forms a saturated, partially
saturated or unsaturated 5- or 6-membered heterocycle; R.sup.1,
R.sup.2, R.sup.6, R.sup.7 are hydrogen, alkyl, haloalkyl, alkoxy or
haloalkoxy; R.sup.3 is halogen, alkyl, haloalkyl, alkoxy or
haloalkoxy; R.sup.4 is hydrogen, nitro, halogen, cyano, alkyl,
haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio,
alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
unsubstituted or substituted aminosulfonyl or unsubstituted or
substituted sulfonylamino; R.sup.5 is hydrogen, alkyl or halogen; l
is 0, 1 or 2; R.sup.8 is hydrogen, alkyl, haloalkyl, alkylcarbonyl,
formyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylsulfonyl or
haloalkylsulfonyl; R.sup.9 is substituted pyrazol-4-ylcarbonyl or
substituted 5-oxopyrazolin-4-ylmethylidene; and their
agriculturally useful salts; processes and intermediates for
preparing the tricyclic benzoylpyrazole derivatives; compositions
comprising them and the use of these derivatives or of the
compositions comprising them for controlling undesirable plants are
described.
Inventors: |
Witschel; Matthias;
(Ludwigshafen, DE) ; Kudis; Steffen; (Mannheim,
DE) ; Langemann; Klaus; (Worms, DE) ; Baumann;
Ernst; (Dudenhofen, DE) ; von Deyn; Wolfgang;
(Neustadt, DE) ; Mayer; Guido; (Neustadt, DE)
; Misslitz; Ulf; (Neustadt, DE) ; Neidlein;
Ulf; (Mannheim, DE) ; Otten; Martina;
(Ludwigshafen, DE) ; Westphalen; Karl-Otto;
(Speyer, DE) ; Walter; Helmut; (Obrigheim,
DE) |
Correspondence
Address: |
NOVAK DRUCE DELUCA & QUIGG, LLP
1300 EYE STREET NW
SUITE 1000 WEST TOWER
WASHINGTON
DC
20005
US
|
Family ID: |
7900849 |
Appl. No.: |
11/461491 |
Filed: |
August 1, 2006 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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09936356 |
Sep 11, 2001 |
7115545 |
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PCT/EP00/02010 |
Mar 8, 2000 |
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11461491 |
Aug 1, 2006 |
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Current U.S.
Class: |
504/288 ;
504/235; 504/238; 504/292; 514/248; 514/454; 548/356.1; 548/373.1;
548/376.1; 549/228; 549/23 |
Current CPC
Class: |
C07D 413/06 20130101;
A01N 43/90 20130101; C07D 495/04 20130101; C07D 491/04 20130101;
A01N 43/80 20130101 |
Class at
Publication: |
504/288 ;
504/235; 504/238; 504/292; 514/248; 514/454; 548/356.1; 548/373.1;
548/376.1; 549/228; 549/023 |
International
Class: |
A01N 43/02 20060101
A01N043/02; A01N 43/08 20060101 A01N043/08; A01N 43/16 20060101
A01N043/16; A01N 43/18 20060101 A01N043/18; A01N 43/58 20060101
A01N043/58 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 12, 1999 |
DE |
19911219.3 |
Claims
1.-20. (canceled)
21. A tricyclic benzoylpyrazole compound of formula I ##STR64##
where: X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2,
CR.sup.6R.sup.7, or NR.sup.8; Y together with the two carbons to
which it is attached forms a saturated, partially saturated or
unsaturated 5- or 6-membered heterocycle which contains one to
three identical or different heteroatoms selected from the
following group: oxygen, sulfur and nitrogen; R.sup.1, R.sup.2,
R.sup.6, R.sup.7 are hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; R.sup.3 is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; R.sup.4 is
hydrogen, nitro, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, aminosulfonyl,
N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
R.sup.5 is hydrogen, C.sub.1-C.sub.6-alkyl or halogen; R.sup.8 is
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylcarbonyl, formyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
l is 0, 1 or 2; R.sup.9 is a radical IIa or IIb ##STR65## where
R.sup.10 is hydroxyl, mercapto, halogen, OR.sup.13, SR.sup.13,
SO.sub.2R.sup.14, NR.sup.15R.sup.16 or N-bonded heterocyclyl, where
the heterocyclyl radical may be partially or fully halogenated
and/or may carry one to three of the following radicals: nitro,
cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; R.sup.11 is
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.3-C.sub.6-cycloalkyl, hydroxyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; R.sup.12 is hydrogen, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, hydroxyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio or C.sub.1-C.sub.6-haloalkylthio;
R.sup.13 is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.20-alkylcarbonyl, C.sub.2-C.sub.20-alkenylcarbonyl,
C.sub.2-C.sub.6-alkynylcarbonyl,
C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl,
C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl,
C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl or
N,N-di(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl,
where the abovementioned alkyl, cycloalkyl and alkoxy radicals may
be partially or fully halogenated and/or may carry one to three of
the following groups: cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl; is
phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl,
heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,
phenylaminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-(phenyl)aminocarbonyl,
heterocyclylaminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-(heterocyclyl)aminocarbonyl,
phenyl-C.sub.2-C.sub.6-alkenylcarbonyl or
heterocyclyl-C.sub.2-C.sub.6-alkenylcarbonyl, where the phenyl and
the heterocyclyl radical of the 18 lastmentioned substitutents may
be partially or fully halogenated and/or may carry one to three of
the following radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl,
where the two lastmentioned substitutents for their part may be
partially or fully halogenated and/or may carry one to three of the
following radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; R.sup.14 is C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl,
C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy,
di(C.sub.1-C.sub.6-alkyl)amino or
di(C.sub.1-C.sub.6-haloalkyl)amino, where the abovementioned alkyl,
cycloalkyl and alkoxy radicals may be partially or fully
halogenated and/or may carry one to three of the following groups:
cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl; is
phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl, phenoxy, heterocyclyloxy, where
the phenyl and the heterocyclyl radical of the lastmentioned
substitutents may be partially or fully halogenated and/or may
carry one to three of the following radicals: nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; R.sup.15 is
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy, di(C.sub.1-C.sub.6-alkyl)amino or
C.sub.1-C.sub.6-alkylcarbonylamino, where the abovementioned alkyl,
cycloalkyl and alkoxy radicals may be partially or fully
halogenated and/or may carry one to three radicals of the following
group: cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl; is
phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl or
heterocyclyl-C.sub.1-C.sub.6-alkyl, where the phenyl or
heterocyclyl radical of the four lastmentioned substitutents may be
partially or fully halogenated and/or may carry one to three of the
following radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; R.sup.16 is C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl or
C.sub.1-C.sub.6-alkylcarbonyl; or an agriculturally useful salt
thereof.
22. The tricyclic benzoylpyrazole compound of formula I defined in
claim 21 where R.sup.9 is IIa.
23. The tricyclic benzoylpyrazole compound of formula I defined in
claim 21 where X is oxygen, sulfur or CR.sup.6R.sup.7.
24. The tricyclic benzoylpyrazole compound of formula I defined in
claim 21 where Y together with the two carbons to which it is
attached forms a heterocycle selected from the following group:
dihydroisoxazolediyl, isoxazolediyl or tetrahydroisoxazolediyl.
25. The tricyclic benzoylpyrazole compound of formula I defined in
claim 21 where R.sup.1, R.sup.2 are hydrogen; R.sup.3 is
C.sub.1-C.sub.6-alkyl; R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; R.sup.5 is hydrogen; l is 0 oder
1.
26. The tricyclic benzoylpyrazole compound of formula I defined in
claim 21 where R.sup.10 is hydroxyl; R.sup.11 is
C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl; R.sup.12 is
hydrogen or C.sub.1-C.sub.6-alkyl.
27. A process for preparing the compound of formula I where
R.sup.10=halogen as claimed in claim 21, which comprises reacting a
tricyclic benzoylpyrazole compound of formula I.alpha. (=I where
R.sup.10=hydroxyl), ##STR66## where the variables R.sup.1 to
R.sup.5, R.sup.11 and R.sup.12, X, Y and l are as defined in claim
21, with a halogenating agent.
28. A process for preparing the compound of formula I where
R.sup.10=OR.sup.13 as claimed in claim 21, which comprises reacting
a tricyclic benzoylpyrazole compound of formula I.alpha. (=I where
R.sup.10=hydroxyl), ##STR67## where the variables R.sup.1 to
R.sup.5, R.sup.11 and R.sup.12, X, Y and l are as defined in claim
21, with a compound of formula III L.sup.1R.sup.13 III where the
variable R.sup.13 is as defined in claim 21 and L.sup.1 is a
nucleophilically replaceable leaving group.
29. A process for preparing the compound of formula I where
R.sup.10=OR.sup.13, SR.sup.13, NR.sup.15R.sup.16 or N-bonded
heterocyclyl as claimed in claim 21, which comprises reacting a
compound of formula I.beta. (.ident.I where R.sup.10=halogen),
##STR68## where the variables R.sup.1 to R.sup.5, R.sup.11 and
R.sup.12, X, Y and l are as defined in claim 21, with a compound of
formula IV.alpha., IV.beta., IV.gamma. or IV.delta. ##STR69##
HOR.sup.13HSR.sup.13NHR.sup.15R.sup.16H(N-bonded heterocyclyl) Ivo.
IVp ivy IV8 where the variables R.sup.13 to R.sup.16 are as defined
in claim 21, optionally in the presence of a base.
30. A process for preparing the compound of formula I where
R.sup.10=SO.sub.2R.sup.14 as claimed in claim 21, which comprises
reacting a compound of formula I.gamma. (.ident.I where
R.sup.10=SR.sup.14), ##STR70## where the variables R.sup.1 to
R.sup.5, R.sup.11 and R.sup.12, X, Y and l are as defined in claim
21, with an oxidizing agent.
31. A process for preparing the compound of formula I where
R.sup.9=IIa as claimed in claim 21, which comprises reacting a
metalated pyrazole compound of formula V where M is a metal and
R.sup.10 to R.sup.12 are as defined in claim 21, except for
R.sup.10=hydroxyl and mercapto, with a tricyclic benzoic acid
compound of formula VI.alpha. where R.sup.1 to R.sup.5, X, Y and l
are as defined in claim 21 and L.sup.2 is a nucleophilically
replaceable leaving group. ##STR71##
32. A process for preparing the compound of formula I.alpha. (=I
where R.sup.10=hydroxyl) as claimed in claim 21, which comprises
acylating a pyrazole of formula VII in which the variables R.sup.11
and R.sup.12 are as defined in claim 21 ##STR72## with an activated
tricyclic benzoic acid of formula VI.beta. or with a tricyclic
benzoic acid of formula VI.gamma., ##STR73## where the variables
R.sup.1 to R.sup.5, X, Y and l are as defined in claim 21 and
L.sup.3 is a nucleophilically replaceable leaving group, and
rearranging the acylation product, optionally in the presence of a
catalyst.
33. A process for preparing the compound of formula I.alpha.
(.ident.I where R.sup.10=hydroxyl) as claimed in claim 21, which
comprises reacting a pyrazole of formula VII in which the variables
R.sup.11 and R.sup.12 are as defined in claim 21, or an alkali
metal salt thereof, ##STR74## with a tricyclic benzene compound of
formula IX where L.sup.4 is a leaving group and the variables X, Y,
R.sup.1 to R.sup.5 and l are as defined in claim 21 ##STR75## in
the presence of carbon monoxide, a catalyst and a base.
34. A composition, comprising a herbicidally effective amount of at
least one compound of formula I or an agriculturally useful salt
thereof as claimed in claim 21 and auxiliaries which are customary
for formulating crop protection agents.
35. A process for preparing the composition defined in claim 34,
which comprises mixing a herbicidally effective amount of at least
one compound of formula I or an agriculturally useful salt thereof
and auxiliaries which are customary for formulating crop protection
agents.
36. A method for controlling undesirable vegetation, which
comprises allowing a herbicidally effective amount of at least one
compound of formula I or an agriculturally useful salt thereof as
claimed in claim 21 to act on plants, their habitat or on seed.
37. A tricyclic benzoic acid compound of formula VI ##STR76## in
which the variables X, Y, R.sup.1 to R.sup.3 and R.sup.5 and l are
as defined in claim 21 and R.sup.4 is nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
R.sup.17 is hydroxyl or a radical which can be removed by
hydrolysis.
38. A tricyclic benzene compound of formula IX ##STR77## in which
the variables X, Y, R.sup.1 to R.sup.3 and R.sup.5 and l are as
defined in claim 21 and R.sup.4 is nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
R.sup.5 is hydrogen or C.sub.1-C.sub.6-alkyl; L.sup.4 is halogen,
C.sub.1-C.sub.6-alkylsulfonyloxy,
C.sub.1-C.sub.6-haloalkylsulfonyloxy or phenylsulfonyloxy, where
the phenyl ring of the lastmentioned radical may be unsubstituted
or partially or fully halogenated and/or may carry one to three of
the following radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy.
39. An aniline compound of formula XV ##STR78## in which the
variables X, Y, R.sup.1 to R.sup.3 and R.sup.5 and 1 are in each
case as defined in claim 21 and R.sup.4 is nitro, halogen, cyano,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, aminosulfonyl,
N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino.
40. A nitrile compound of formula XVI ##STR79## in which the
variables X, Y, R.sup.1 to R.sup.3 and l are in each case as
defined in claim 21 and R.sup.4 is nitro, halogen, cyano,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkinylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, aminosulfonyl,
N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di-(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
R.sup.5 is hydrogen or C.sub.1-C.sub.6-alkyl.
41. The compound of formula I defined in claim 21, wherein X is O
or S; Y together with the two carbons to which it is attached forms
an isoxazole ring which is saturated, partially saturated or
unsaturated; and R.sup.9 is a radical IIa.
42. The compound of formula I defined in claim 41, wherein R.sup.10
is hydroxyl, mercapto, halogen, OR.sup.13, SR.sup.13,
SO.sub.2R.sup.14 or NR.sup.15R.sup.16.
Description
[0001] The present invention relates to novel tricyclic
benzoylpyrazole derivatives of the formula I ##STR2## where: [0002]
X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2, CR.sup.6R.sup.7,
NR.sup.8 or a bond; [0003] Y together with the two carbons to which
it is attached forms a saturated, partially saturated or
unsaturated 5- or 6-membered heterocycle which contains one to
three identical or different heteroatoms selected from the
following group: oxygen, sulfur or nitrogen; [0004] R.sup.1,
R.sup.2, R.sup.6, R.sup.7 are hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0005] R.sup.3 is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0006]
R.sup.4 is hydrogen, nitro, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, aminosulfonyl,
N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl) amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
[0007] R.sup.5 is hydrogen, C.sub.1-C.sub.6-alkyl or halogen;
[0008] R.sup.8 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, formyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
[0009] l is 0, 1 or 2; [0010] R.sup.9 is a radical IIa or IIb
##STR3## where [0011] R.sup.10 is hydroxyl, mercapto, halogen,
OR.sup.13, SR.sup.13, SO.sub.2R.sup.14, NR.sup.15R.sup.16 or
N-bonded heterocyclyl, where the heterocyclyl radical may be
partially or fully halogenated and/or may carry one to three of the
following radicals: [0012] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0013] R.sup.11 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.3-C.sub.6-cycloalkyl, hydroxyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0014] R.sup.12 is hydrogen, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, hydroxyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio or C.sub.1-C.sub.6-haloalkylthio; [0015]
R.sup.13 is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.20-alkylcarbonyl, C.sub.2-C.sub.20-alkenylcarbonyl,
C.sub.2-C.sub.6-alkynylcarbonyl,
C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl,
C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)
aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl,
C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl or
N,N-di(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl,
where the abovementioned alkyl, cycloalkyl and alkoxy radicals may
be partially or fully halogenated and/or may carry one to three of
the following groups: [0016] cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl;
[0017] is phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl,
heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,
phenylaminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-(phenyl)aminocarbonyl,
heterocyclylaminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-(heterocyclyl)aminocarbonyl,
phenyl-C.sub.2-C.sub.6-alkenylcarbonyl or
heterocyclyl-C.sub.2-C.sub.6-alkenylcarbonyl, where the phenyl and
the heterocyclyl radical of the 18 lastmentioned substitutents may
be partially or fully halogenated and/or may carry one to three of
the following radicals: [0018] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl,
where the two lastmentioned substitutents for their part may be
partially or fully halogenated and/or may carry one to three of the
following radicals: [0019] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0020] R.sup.14 is
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, di(C.sub.1-C.sub.6-alkyl)amino or
di(C.sub.1-C.sub.6-haloalkyl)amino, where the above-mentioned
alkyl, cycloalkyl and alkoxy radicals may be partially or fully
halogenated and/or may carry one to three of the following groups:
[0021] cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl;
[0022] is phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl, phenoxy, heterocyclyloxy, where
the phenyl and the heterocyclyl radical of the lastmentioned
substitutents may be partially or fully halogenated and/or may
carry one to three of the following radicals: [0023] nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; [0024]
R.sup.15 is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy, di(C.sub.1-C.sub.6-alkyl)amino or
C.sub.1-C.sub.6-alkylcarbonylamino, where the abovementioned alkyl,
cycloalkyl and alkoxy radicals may be partially or fully
halogenated and/or may carry one to three radicals of the following
group: [0025] cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl,
hydroxycarbonyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl, aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl;
[0026] is phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl or
heterocyclyl-C.sub.1-C.sub.6-alkyl, where the phenyl or
heterocyclyl radical of the four lastmentioned substitutents may be
partially or fully halogenated and/or may carry one to three of the
following radicals: [0027] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0028] R.sup.16 is
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl or C.sub.1-C.sub.6-alkylcarbonyl; and their
agriculturally useful salts.
[0029] Moreover, the invention relates to processes and
intermediates for preparing compounds of the formula I, to
compositions comprising them, and to the use of these derivatives
or of the compositions comprising them for controlling harmful
plants.
[0030] WO 97/19087 and EP-A 860 441 disclose tricyclic compounds
which are characterized in that the respective benzoyl unit that
they contain is fused via positions 3 and 4 with a bicycle.
However, the herbicidal properties of the prior-art compounds and
their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel,
biologically, in particular herbicidally, active compounds having
improved properties.
[0031] We have found that this object is achieved by the tricyclic
benzoylpyrazole derivatives of the formula I and their herbicidal
action.
[0032] Furthermore, we have found processes and intermediates for
synthesizing the compounds of the formula I. Likewise, we have
found herbicidal compositions which comprise the compounds I and
have very good herbicidal action. Moreover, we have found processes
for preparing these compositions and methods for controlling
undesirable vegetation using the compounds I.
[0033] Depending on the substitution pattern, the compounds of the
formula I can contain one or more chiral centers, in which case
they are present as enantiomers or diastereomer mixtures. The
invention provides both the pure enantiomers or diastereomers and
their mixtures.
[0034] The compounds of the formula I can also be present in the
form of their agriculturally useful salts, the type of salt
generally being immaterial. Generally suitable are the salts of
those cations or the acid addition salts of those acids whose
cations and anions, respectively, do not negatively affect the
herbicidal action of the compounds I.
[0035] Suitable cations are, in particular, ions of the alkali
metals, preferably lithium, sodium and potassium, of the alkaline
earth metals, preferably calcium and magnesium, and of the
transition metals, preferably manganese, copper, zinc and iron, and
also ammonium, where, if desired, one to four hydrogen atoms may be
replaced by C.sub.1-C.sub.4-alkyl, hydroxy-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
hydroxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, phenyl or
benzyl, preferably ammonium, dimethylammonium, diisopropylammonium,
tetramethylammonium, tetrabutylammonium,
2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,
di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore
phosphonium ions, sulfonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfonium, and sulfoxonium ions,
preferably tri(C.sub.1-C.sub.4-alkyl)sulfoxonium.
[0036] Anions of useful acid addition salts are primarily chloride,
bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate,
hydrogen phosphate, nitrate, hydrogen carbonate, carbonate,
hexafluorosilicate, hexafluorophosphate, benzoate and the anions of
C.sub.1-C.sub.4-alkanoic acids, preferably formate, acetate,
propionate and butyrate.
[0037] In the case of R.sup.10=hydroxyl or mercapto, IIa also
represents the tautomeric forms IIa' and IIa'' ##STR4##
[0038] Likewise, in the case of R.sup.10=hydroxyl or mercapto, IIb
also represents the tautomeric forms IIb' and IIb'' ##STR5##
[0039] The organic molecular moieties mentioned for the
substitutents R.sup.1-R.sup.17 or as radicals on phenyl and
heterocyclyl radicals are collective terms for individual
enumerations of the individual group members. All hydrocarbon
chains, i.e. all alkyl, haloalkyl, hydroxyalkyl, alkoxy,
haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,
haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, N-alkylamino,
N,N-dialkylamino, N-haloalkylamino, N,N-dihaloalkylamino,
N-alkylsulfonylamino, N-haloalkylsulfonylamino,
N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino,
alkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl,
alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl,
dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl,
hydroxyalkoxyalkyl, alkylcarbonylalkyl, alkoxyiminoalkyl,
N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl,
phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl,
N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl,
N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl,
heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl,
dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl,
alkenyloxycarbonyl, alkenylaminocarbonyl,
N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl,
alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl,
N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl,
alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy and
alkynyloxy moieties, may be straight-chain or branched. Unless
indicated otherwise, halogenated substitutents preferably carry one
to five identical or different halogen atoms. The term halogen
denotes in each case fluorine, chlorine, bromine or iodine.
[0040] Examples of other meanings are: [0041] C.sub.1-C.sub.4-alkyl
and the alkyl moieties of hydroxy-C.sub.1-C.sub.4-alkyl: for
example methyl, ethyl, propyl, 1-methylethyl, butyl,
1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; [0042]
C.sub.1-C.sub.6-alkyl, and the alkyl moieties of
C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl,
N-(di-C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-phenylaminocarbonyl,
N--(C.sub.1-C.sub.6-alkyl)-N-heterocyclylaminocarbonyl,
phenyl-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)
amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl: C.sub.1-C.sub.4-alkyl
as mentioned above, and also, for example, pentyl, 1-methylbutyl,
2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,
hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,
2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,
1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,
2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or
1-ethyl-3-methylpropyl; [0043] C.sub.1-C.sub.4-haloalkyl: a
C.sub.1-C.sub.4-alkyl radical as mentioned above which is partially
or fully substituted by fluorine, chlorine, bromine and/or iodine,
i.e., for example, chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,
dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,
2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,
3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,
2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,
3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,
2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,
1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,
1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl,
4-bromobutyl or nonafluorobutyl; [0044] C.sub.1-C.sub.6-haloalkyl,
and the haloalkyl moieties of N--C.sub.1-C.sub.6-haloalkylamino and
N,N-(di-C.sub.1-C.sub.6-haloalkyl)amino: C.sub.1-C.sub.4-haloalkyl
as mentioned above, and also, for example, 5-fluoropentyl,
5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl,
6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or
dodecafluorohexyl; [0045] C.sub.1-C.sub.4-alkoxy: for example
methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,
2-methylpropoxy or 1,1-dimethylethoxy; [0046]
C.sub.1-C.sub.6-alkoxy, and the alkoxy moieties of
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl
and
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl:
C.sub.1-C.sub.4-alkoxy as mentioned above, and also, for example,
pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,
1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,
1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,
3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,
1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,
2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,
2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,
1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy; [0047]
C.sub.1-C.sub.4-haloalkoxy: a C.sub.1-C.sub.4-alkoxy radical as
mentioned above which is partially or fully substituted by
fluorine, chlorine, bromine and/or iodine, i.e., for example,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy,
2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,
3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,
3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2,3-dichloropropoxy, 3,3,3-trifluoropropoxy,
3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy,
heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy,
1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,
4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
[0048] C.sub.1-C.sub.6-haloalkoxy: C.sub.1-C.sub.4-haloalkoxy as
mentioned above, and also, for example, 5-fluoropentoxy,
5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,
undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,
6-iodohexoxy or dodecafluorohexoxy; [0049]
C.sub.1-C.sub.4-alkylthio: for example methylthio, ethylthio,
propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,
2-methylpropylthio or 1,1-dimethylethylthio; [0050]
C.sub.1-C.sub.6-alkylthio, and the alkylthio moieties of
C.sub.1-C.sub.6-alkylthiocarbonyl: C.sub.1-C.sub.4-alkylthio as
mentioned above and also, for example, pentylthio,
1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,
2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,
1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,
2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
1,1-dimethylbutylthio, 1,2-dimethylbutylthio,
1,3-dimethylbutylthio, 2,2-dimethylbutylthio,
2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,
2-ethylbutylthio, 1,1,2-trimethylpropylthio,
1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or
1-ethyl-2-methylpropylthio; [0051] C.sub.1-C.sub.6-haloalkylthio: a
C.sub.1-C.sub.6-alkylthio radical as mentioned above which is
partially or fully substituted by fluorine, chlorine, bromine
and/or iodine, i.e., for example, fluoromethylthio,
difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio,
bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio,
2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,
2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,
2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,
2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,
3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,
2,2-difluoropropylthio, 2,3-difluoropropylthio,
2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,
3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,
heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,
1-(chloromethyl)-2-chloroethylthio,
1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,
4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio,
5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,
5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,
6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or
dodecafluorohexylthio; [0052] C.sub.1-C.sub.6-alkylsulfinyl
(C.sub.1-C.sub.6-alkyl-S(.dbd.O)--): for example methylsulfinyl,
ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl,
butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,
2-methylbutylsulfinyl, 3-methylbutylsulfinyl,
2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl,
1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,
hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl,
3-methylpentylsulfinyl, 4-methylpentylsulfinyl,
1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,
1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,
2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,
1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,
1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,
1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
[0053] C.sub.1-C.sub.6-haloalkylsulfinyl: a
C.sub.1-C.sub.6-alkylsulfinyl radical as mentioned above which is
partially or fully substituted by fluorine, chlorine, bromine
and/or iodine, i.e., for example, fluoromethylsulfinyl,
difluoromethylsulfinyl, trifluoromethylsulfinyl,
chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,
2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,
2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,
2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,
2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,
2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,
2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,
2-chloropropylsulfinyl, 3-chloropropylsulfinyl,
2-bromopropylsulfinyl, 3-bromopropylsulfinyl,
2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,
2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,
3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl,
heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl,
1-(chloromethyl)-2-chloroethylsulfinyl,
1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,
4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,
nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,
5-chloropentylsulfinyl, 5-bromopentylsulfinyl,
5-iodopentylsulfinyl, undecafluoropentylsulfinyl,
6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,
6-iodohexylsulfinyl or dodecafluorohexylsulfinyl; [0054]
C.sub.1-C.sub.6-alkylsulfonyl
(C.sub.1-C.sub.6-alkyl-S(.dbd.O).sub.2--), and the alkylsulfonyl
radicals of N--(C.sub.1-C.sub.6-alkylsulfonyl)amino and
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino:
for example methylsulfonyl, ethylsulfonyl, propylsulfonyl,
1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,
2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl,
1-methylbutylsulfonyl, 2-methylbutylsulfonyl,
3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,
1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,
1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,
2-methylpentylsulfonyl, 3-methylpentylsulfonyl,
4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,
1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,
2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,
3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,
2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,
1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or
1-ethyl-2-methylpropylsulfonyl; [0055]
C.sub.1-C.sub.6-haloalkylsulfonyl, and the haloalkylsulfonyl
radicals of N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino and
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino:
a C.sub.1-C.sub.6-alkylsulfonyl radical as mentioned above which is
partially or fully substituted by fluorine, chlorine, bromine
and/or iodine, i.e., for example, fluoromethylsulfonyl,
difluoromethylsulfonyl, trifluoromethylsulfonyl,
chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,
2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,
2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,
2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,
2-chloro-2,2-difluoroethylsulfonyl,
2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl,
pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl,
3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,
3-chloropropylsulfonyl, 2-bromopropylsulfonyl,
3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl,
2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl,
3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl,
2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,
1-(fluoromethyl)-2-fluoroethylsulfonyl,
1-(chloromethyl)-2-chloroethylsulfonyl,
1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,
4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,
nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,
5-chloropentylsulfonyl, 5-bromopentylsulfonyl,
5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl,
6-iodohexylsulfonyl or dodecafluorohexylsulfonyl; [0056]
C.sub.1-C.sub.6-alkylamino, and the alkylamino radicals of
N--(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl: for
example methylamino, ethylamino, propylamino, 1-methylethylamino,
butylamino, 1-methylpropylamino, 2-methylpropylamino,
1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,
2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,
1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,
1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino,
3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino,
1,2-dimethylbutylamino, 1,3-dimethylbutylamino,
2,2-dimethylbutylamino, 2,3-dimethylbutylamino,
3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino,
1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,
1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino; [0057]
(C.sub.1-C.sub.6-alkylamino)sulfonyl: for example
methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl,
1-methylethylaminosulfonyl, butylaminosulfonyl,
1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl,
1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl,
1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl,
3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl,
1-ethylpropylaminosulfonyl, hexylaminosulfonyl,
1,1-dimethylpropylaminosulfonyl, 1,2-dimethylpropylaminosulfonyl,
1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl,
3-methylpentylaminosulfonyl, 4-methylpentylaminosulfonyl,
1,1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl,
1,3-dimethylbutylaminosulfonyl, 2,2-dimethylbutylaminosulfonyl,
2,3-dimethylbutylaminosulfonyl, 3,3-dimethylbutylaminosulfonyl,
1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl,
1,1,2-trimethylpropylaminosulfonyl,
1,2,2-trimethylpropylaminosulfonyl,
1-ethyl-1-methylpropylaminosulfonyl or
1-ethyl-2-methylpropylaminosulfonyl; [0058]
di(C.sub.1-C.sub.6-alkyl)aminosulfonyl: for example
N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl,
N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl,
N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl,
N,N-di(2-methylpropyl)aminosulfonyl,
N,N-di(1,1-dimethylethyl)aminosulfonyl,
N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl,
N-methyl-N-(1-methylethyl)aminosulfonyl,
N-butyl-N-methylaminosulfonyl,
N-methyl-N-(1-methylpropyl)aminosulfonyl,
N-methyl-N-(2-methylpropyl)aminosulfonyl,
N-(1,1-dimethylethyl)-N-methylaminosulfonyl,
N-ethyl-N-propylaminosulfonyl,
N-ethyl-N-(1-methylethyl)aminosulfonyl,
N-butyl-N-ethylaminosulfonyl,
N-ethyl-N-(1-methylpropyl)aminosulfonyl,
N-ethyl-N-(2-methylpropyl)aminosulfonyl,
N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl,
N-(1-methylethyl)-N-propylaminosulfonyl,
N-butyl-N-propylaminosulfonyl,
N-(1-methylpropyl)-N-propylaminosulfonyl,
N-(2-methylpropyl)-N-propylaminosulfonyl,
N-(1,1-dimethylethyl)-N-propylaminosulfonyl,
N-butyl-N-(1-methylethyl)aminosulfonyl,
N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl,
N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl,
N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl,
N-butyl-N-(1-methylpropyl)aminosulfonyl,
N-butyl-N-(2-methylpropyl)aminosulfonyl,
N-butyl-N-(1,1-dimethylethyl)aminosulfonyl,
N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl,
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl,
N-methyl-N-pentylaminosulfonyl,
N-methyl-N-(1-methylbutyl)aminosulfonyl,
N-methyl-N-(2-methylbutyl)aminosulfonyl,
N-methyl-N-(3-methylbutyl)aminosulfonyl,
N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl,
N-methyl-N-(1-ethylpropyl)aminosulfonyl,
N-methyl-N-hexylaminosulfonyl,
N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl,
N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl,
N-methyl-N-(1-methylpentyl)aminosulfonyl,
N-methyl-N-(2-methylpentyl)aminosulfonyl,
N-methyl-N-(3-methylpentyl)aminosulfonyl,
N-methyl-N-(4-methylpentyl)aminosulfonyl,
N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl,
N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl,
N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl,
N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl,
N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl,
N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl,
N-methyl-N-(1-ethylbutyl)aminosulfonyl,
N-methyl-N-(2-ethylbutyl)aminosulfonyl,
N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,
N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,
N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,
N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,
N-ethyl-N-pentylaminosulfonyl,
N-ethyl-N-(1-methylbutyl)aminosulfonyl,
N-ethyl-N-(2-methylbutyl)aminosulfonyl,
N-ethyl-N-(3-methylbutyl)aminosulfonyl,
N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl,
N-ethyl-N-(1-ethylpropyl)aminosulfonyl,
N-ethyl-N-hexylaminosulfonyl,
N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl,
N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl,
N-ethyl-N-(1-methylpentyl)aminosulfonyl,
N-ethyl-N-(2-methylpentyl)aminosulfonyl,
N-ethyl-N-(3-methylpentyl)aminosulfonyl,
N-ethyl-N-(4-methylpentyl)aminosulfonyl,
N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl,
N-ethyl-N-(1-ethylbutyl)aminosulfonyl,
N-ethyl-N-(2-ethylbutyl)aminosulfonyl,
N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,
N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,
N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,
N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,
N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl,
N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl,
N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or
N,N-dihexylaminosulfonyl;
[0059] di(C.sub.1-C.sub.4-alkyl)amino, and the dialkylamino
radicals of
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl and
N-(di-C.sub.1-C.sub.4-alkylamino)imino-C.sub.1-C.sub.6-alkyl: for
example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,
N,N-di(1-methylethyl)amino, N,N-dibutylamino,
N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,
N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,
N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,
N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,
N-methyl-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,
N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,
N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino,
N-ethyl-N-(1,1-dimethylethyl)amino,
N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,
N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,
N-(1,1-dimethylethyl)-N-propylamino,
N-butyl-N-(1-methylethyl)amino,
N-(1-methylethyl)-N-(1-methylpropyl)amino,
N-(1-methylethyl)-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,
N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,
N-butyl-N-(1,1-dimethylethyl)amino,
N-(1-methylpropyl)-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or
N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino; [0060]
di(C.sub.1-C.sub.6-alkyl)amino, and the dialkylamino radicals of
di(C.sub.1-C.sub.6-alkyl)aminoimino-C.sub.1-C.sub.6-alkyl:
di(C.sub.1-C.sub.4-alkyl)amino as mentioned above, and also
N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,
N-ethyl-N-pentylamino, N-methyl-N-hexylamino or
N-ethyl-N-hexylamino; [0061] C.sub.1-C.sub.4-alkylcarbonyl: for
example methylcarbonyl, ethylcarbonyl, propylcarbonyl,
1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl,
2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl; [0062]
C.sub.1-C.sub.6-alkylcarbonyl, and the alkylcarbonyl radicals of
C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl:
C.sub.1-C.sub.4-alkylcarbonyl as mentioned above, and also, for
example, pentylcarbonyl, 1-methylbutylcarbonyl,
2-methylbutylcarbonyl, 3-methylbutylcarbonyl,
2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,
1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,
1-methylpentylcarbonyl, 2-methylpentylcarbonyl,
3-methylpentylcarbonyl, 4-methylpentylcarbonyl,
1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,
1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,
2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl,
1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,
1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,
1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
[0063] C.sub.1-C.sub.20-alkylcarbonyl:
C.sub.1-C.sub.6-alkylcarbonyl as mentioned above, and also
heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or
heptadecylcarbonyl; [0064] C.sub.1-C.sub.4-alkoxycarbonyl, and the
alkoxycarbonyl moieties of
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkoxycarbonyl: for
example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,
1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,
2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl; [0065]
(C.sub.1-C.sub.6-alkoxy)carbonyl: (C.sub.1-C.sub.4-alkoxy)carbonyl
as mentioned above, and also, for example, pentoxycarbonyl,
1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,
3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,
1-ethylpropoxycarbonyl, hexoxycarbonyl,
1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,
1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,
3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,
1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,
1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,
2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,
1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,
1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,
1-ethyl-1-methyl-propoxycarbonyl or
1-ethyl-2-methyl-propoxycarbonyl; [0066]
C.sub.1-C.sub.6-haloalkoxycarbonyl: a
C.sub.1-C.sub.6-alkoxycarbonyl radical as mentioned above which is
partially or fully substituted by fluorine, chlorine, bromine
and/or iodine, i.e., for example, fluoromethoxycarbonyl,
difluoromethoxycarbonyl, trifluoromethoxycarbonyl,
chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl,
2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl,
2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl,
2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl,
2-chloro-2-fluoroethoxycarbonyl,
2-chloro-2,2-difluoroethoxycarbonyl,
2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl,
pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl,
3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl,
3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl,
3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl,
2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl,
3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl,
2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl,
1-(fluoromethyl)-2-fluoroethoxycarbonyl,
1-(chloromethyl)-2-chloroethoxycarbonyl,
1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,
4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl,
nonafluorobutoxycarbonyl, 5-fluoropentoxycarbonyl,
5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl,
5-iodopentoxycarbonyl, 6-fluorohexoxycarbonyl,
6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl or
dodecafluorohexoxycarbonyl; [0067]
(C.sub.1-C.sub.4-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,
propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,
1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or
1,1-dimethylethylcarbonyloxy; [0068]
(C.sub.1-C.sub.4-alkylamino)carbonyl: for example
methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,
1-methylethylaminocarbonyl, butylaminocarbonyl,
1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or
1,1-dimethylethylaminocarbonyl; [0069]
(C.sub.1-C.sub.6-alkylamino)carbonyl:
(C.sub.1-C.sub.4-alkylamino)carbonyl as mentioned above, and also,
for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl,
2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,
2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl,
hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,
1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,
2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,
4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,
1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,
2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,
3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,
2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,
1,2,2-trimethylpropylaminocarbonyl,
1-ethyl-1-methylpropylaminocarbonyl or
1-ethyl-2-methylpropylaminocarbonyl; [0070]
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl: for example
N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,
N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl,
N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl,
N,N-di(2-methylpropyl)aminocarbonyl,
N,N-di(1,1-dimethylethyl)aminocarbonyl,
N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,
N-methyl-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-methylaminocarbonyl,
N-methyl-N-(1-methylpropyl)aminocarbonyl,
N-methyl-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-methylaminocarbonyl,
N-ethyl-N-propylaminocarbonyl,
N-ethyl-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-ethylaminocarbonyl,
N-ethyl-N-(1-methylpropyl)aminocarbonyl,
N-ethyl-N-(2-methylpropyl)aminocarbonyl,
N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,
N-(1-methylethyl)-N-propylaminocarbonyl,
N-butyl-N-propylaminocarbonyl,
N-(1-methylpropyl)-N-propylaminocarbonyl,
N-(2-methylpropyl)-N-propylaminocarbonyl,
N-(1,1-dimethylethyl)-N-propylaminocarbonyl,
N-butyl-N-(1-methylethyl)aminocarbonyl,
N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,
N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-(1-methylpropyl)aminocarbonyl,
N-butyl-N-(2-methylpropyl)aminocarbonyl,
N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,
N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl; [0071]
di(C.sub.1-C.sub.6-alkyl)aminocarbonyl:
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl as mentioned above, and
also, for example, N-methyl-N-pentylaminocarbonyl,
N-methyl-N-(1-methylbutyl)aminocarbonyl,
N-Methyl-N-(2-methylbutyl)aminocarbonyl,
N-methyl-N-(3-methylbutyl)aminocarbonyl,
N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,
N-methyl-N-(1-ethylpropyl)aminocarbonyl,
N-methyl-N-hexylaminocarbonyl,
N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,
N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,
N-methyl-N-(1-methylpentyl)aminocarbonyl,
N-methyl-N-(2-methylpentyl)aminocarbonyl,
N-methyl-N-(3-methylpentyl)aminocarbonyl,
N-methyl-N-(4-methylpentyl)aminocarbonyl,
N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,
N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,
N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,
N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,
N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,
N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,
N-methyl-N-(1-ethylbutyl)aminocarbonyl,
N-methyl-N-(2-ethylbutyl)aminocarbonyl,
N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,
N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,
N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,
N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,
N-ethyl-N-pentylaminocarbonyl,
N-ethyl-N-(1-methylbutyl)aminocarbonyl,
N-ethyl-N-(2-methylbutyl)aminocarbonyl,
N-ethyl-N-(3-methylbutyl)aminocarbonyl,
N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,
N-ethyl-N-(1-ethylpropyl)aminocarbonyl,
N-ethyl-N-hexylaminocarbonyl,
N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,
N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,
N-ethyl-N-(1-methylpentyl)aminocarbonyl,
N-ethyl-N-(2-methylpentyl)aminocarbonyl,
N-ethyl-N-(3-methylpentyl)aminocarbonyl,
N-ethyl-N-(4-methylpentyl)aminocarbonyl,
N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(1-ethylbutyl)aminocarbonyl,
N-ethyl-N-(2-ethylbutyl)aminocarbonyl,
N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,
N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,
N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,
N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,
N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,
N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,
N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or
N,N-dihexylaminocarbonyl; [0072]
di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl: for example
N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,
N,N-di(1-methylethyl)aminothiocarbonyl,
N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl,
N,N-di(1-methylpropyl)aminothiocarbonyl,
N,N-di(2-methylpropyl)aminothiocarbonyl,
N,N-di(1,1-dimethylethyl)aminothiocarbonyl,
N-ethyl-N-methylaminothiocarbonyl,
N-methyl-N-propylaminothiocarbonyl,
N-methyl-N-(1-methylethyl)aminothiocarbonyl,
N-butyl-N-methylaminothiocarbonyl,
N-methyl-N-(1-methylpropyl)aminothiocarbonyl,
N-methyl-N-(2-methylpropyl)aminothiocarbonyl,
N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,
N-ethyl-N-propylaminothiocarbonyl,
N-ethyl-N-(1-methylethyl)aminothiocarbonyl,
N-butyl-N-ethylaminothiocarbonyl,
N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,
N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,
N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,
N-(1-methylethyl)-N-propylaminothiocarbonyl,
N-butyl-N-propylaminothiocarbonyl,
N-(1-methylpropyl)-N-propylaminothiocarbonyl,
N-(2-methylpropyl)-N-propylaminothiocarbonyl,
N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,
N-butyl-N-(1-methylethyl)aminothiocarbonyl,
N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,
N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,
N-butyl-N-(1-methylpropyl)aminothiocarbonyl,
N-butyl-N-(2-methylpropyl)aminothiocarbonyl,
N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,
N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,
N-methyl-N-pentylaminothiocarbonyl,
N-methyl-N-(1-methylbutyl)aminothiocarbonyl,
N-methyl-N-(2-methylbutyl)aminothiocarbonyl,
N-methyl-N-(3-methylbutyl)aminothiocarbonyl,
N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,
N-methyl-N-hexylaminothiocarbonyl,
N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1-methylpentyl)aminothiocarbonyl,
N-methyl-N-(2-methylpentyl)aminothiocarbonyl,
N-methyl-N-(3-methylpentyl)aminothiocarbonyl,
N-methyl-N-(4-methylpentyl)aminothiocarbonyl,
N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,
N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,
N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,
N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,
N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,
N-ethyl-N-pentylaminothiocarbonyl,
N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,
N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,
N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,
N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,
N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,
N-ethyl-N-hexylaminothiocarbonyl,
N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,
N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,
N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,
N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,
N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,
N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,
N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,
N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,
N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,
N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,
N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,
N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,
N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,
N-propyl-N-pentylaminothiocarbonyl,
N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl,
N-propyl-N-hexylaminothiocarbonyl,
N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl
or N,N-dihexylaminothiocarbonyl;
[0073] C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and the
alkoxyalkyl moieties of
hydroxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl:
C.sub.1-C.sub.4-alkyl which is substituted by
C.sub.1-C.sub.4-alkoxy as mentioned above, i.e., for example,
methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl,
butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl,
(1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,
2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,
2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,
2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl,
2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,
2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,
2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl,
3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl,
3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,
3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,
2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,
2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,
2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,
3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,
3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,
3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,
4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,
4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or
4-(1,1-dimethylethoxy)butyl; [0074]
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy as alkoxyalkoxy
moieties of C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl:
C.sub.1-C.sub.4-alkoxy which is substituted by
C.sub.1-C.sub.4-alkoxy as mentioned above, i.e., for example,
methoxymethoxy, ethoxymethoxy, propoxymethoxy,
(1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy,
(2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy,
2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy,
2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy,
2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,
2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy,
2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy,
2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy,
2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy,
3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy,
3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,
3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,
3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,
2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy,
2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,
2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy,
3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,
3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,
3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,
4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy,
4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or
4-(1,1-dimethylethoxy)butoxy; [0075] C.sub.3-C.sub.6-alkenyl, and
the alkenyl moieties of C.sub.3-C.sub.6-alkenylcarbonyl,
C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl:
for example prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl,
2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl,
2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,
3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl,
2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,
1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl,
1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,
1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,
3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,
1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,
3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,
1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,
1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,
1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,
2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,
2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,
1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl,
2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,
1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
[0076] C.sub.2-C.sub.6-alkenyl, and the alkenyl moieties of
C.sub.2-C.sub.6-alkenylcarbonyl,
phenyl-C.sub.2-C.sub.6-alkenylcarbonyl and
heterocyclyl-C.sub.2-C.sub.6-alkenylcarbonyl:
C.sub.3-C.sub.6-alkenyl as mentioned above, and also ethenyl;
[0077] C.sub.2-C.sub.20-alkenyl as alkenyl moiety of
C.sub.2-C.sub.20-alkenylcarbonyl: C.sub.2-C.sub.6-alkenyl as
mentioned above, and also pentadecenyl or heptadecenyl; [0078]
C.sub.3-C.sub.6-haloalkenyl: a C.sub.3-C.sub.6-alkenyl radical as
mentioned above which is partially or fully substituted by
fluorine, chlorine, bromine and/or iodine, i.e., for example,
2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,
2,3,3-trichloroallyl, 2,3-dichlorobut-2-phenyl, 2-bromoallyl,
3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,
2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl; [0079]
C.sub.3-C.sub.6-alkynyl, and the alkynyl moieties of
C.sub.3-C.sub.6-alkynylcarbonyl, C.sub.3-C.sub.6-alkynyloxy,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkoxyamino)carbonyl:
for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl,
pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,
pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,
3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl,
hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl,
hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,
3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,
3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or
4-methylpent-2-yn-5-yl; [0080] C.sub.2-C.sub.6-alkynyl, and the
alkynyl moieties of C.sub.2-C.sub.6-alkynylcarbonyl:
C.sub.3-C.sub.6-alkynyl as mentioned above, and also ethynyl;
[0081] C.sub.3-C.sub.6-haloalkynyl: a C.sub.3-C.sub.6-alkynyl
radical as mentioned above which is partially or fully substituted
by fluorine, chlorine, bromine and/or iodine, i.e., for example,
1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl,
4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,
1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl,
5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl
or 6-iodohex-5-yn-1-yl; [0082] C.sub.3-C.sub.6-cycloalkyl, and the
cycloalkyl moieties of C.sub.3-C.sub.6-cycloalkylcarbonyl: for
example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; [0083]
heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy,
heterocyclylcarbonyl, heterocyclyl-C.sub.1-C.sub.6-alkyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,
heterocyclyl-C.sub.2-C.sub.6-alkenylcarbonyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkyl)-N-(heterocyclyl)aminocarbonyl,
heterocyclylaminocarbonyl: a saturated, partially saturated or
unsaturated 5- or 6-membered heterocyclic ring which is attached
via carbon and contains one to four identical or different
heteroatoms selected from the following group: oxygen, sulfur and
nitrogen, i.e., for example, 5-membered rings having, for example,
one heteroatom, having two heteroatoms, having three heteroatoms or
having four heteroatoms or, for example, 6-membered rings having,
for example, one heteroatom, having two heteroatoms, having three
heteroatoms or having four heteroatoms, i.e. 5-membered rings
having one heteroatom, such as: [0084] tetrahydrofuran-2-yl,
tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl,
tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl,
2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl,
2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl,
4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl,
2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,
2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl,
4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl,
2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl,
2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl,
4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl,
3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,
3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl,
3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl; [0085]
5-membered rings having two heteroatoms such as:
tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl,
tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl,
tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl,
1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl,
tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl,
1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl,
tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl,
tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl,
tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,
tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl,
1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl,
1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,
4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl,
4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl,
2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl,
4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,
4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl,
2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,
2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl,
2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl,
4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,
2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl,
2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl,
2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,
.DELTA..sup.3-1,2-dithiol-3-yl, .DELTA..sup.3-1,2-dithiol-4-yl,
.DELTA..sup.3-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl,
4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl,
2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl,
2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl,
2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl,
4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl,
2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl,
2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl,
2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,
4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl,
4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl,
2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl,
2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl,
2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl,
1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl,
1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl,
isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,
isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl,
oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl
or thiazol-5-yl; [0086] 5-membered rings having three heteroatoms
such as: 1,2,3-.DELTA..sup.2-oxadiazolin-4-yl,
1,2,3-.DELTA..sup.2-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.4-oxadiazolin-3-yl,
1,2,4-.DELTA..sup.4-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.2-oxadiazolin-3-yl,
1,2,4-.DELTA..sup.2-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.3-oxadiazolin-3-yl,
1,2,4-.DELTA..sup.3-oxadiazolin-5-yl,
1,3,4-.DELTA..sup.2-oxadiazolin-2-yl,
1,3,4-.DELTA..sup.2-oxadiazolin-5-yl,
1,3,4-.DELTA..sup.3-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,
1,2,3-.DELTA..sup.2-thiadiazolin-4-yl,
1,2,3-.DELTA..sup.2-thiadiazolin-5-yl,
1,2,4-.DELTA..sup.4-thiadiazolin-3-yl,
1,2,4-.DELTA..sup.4-thiadiazolin-5-yl,
1,2,4-.DELTA..sup.3-thiadiazolin-3-yl,
1,2,4-.DELTA..sup.3-thiadiazolin-5-yl,
1,2,4-.DELTA..sup.2-thiadiazolin-3-yl,
1,2,4-.DELTA..sup.2-thiadiazolin-5-yl,
1,3,4-.DELTA..sup.2-thiadiazolin-2-yl,
1,3,4-.DELTA..sup.2-thiadiazolin-5-yl,
1,3,4-.DELTA..sup.3-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,
1,3,2-dioxathiolan-4-yl, 1,2,3-.DELTA..sup.2-triazolin-4-yl,
1,2,3-.DELTA..sup.2-triazolin-5-yl,
1,2,4-.DELTA..sup.2-triazolin-3-yl,
1,2,4-.DELTA..sup.2-triazolin-5-yl,
1,2,4-.DELTA..sup.3-triazolin-3-yl,
1,2,4-.DELTA..sup.3-triazolin-5-yl,
1,2,4-.DELTA..sup.1-triazolin-2-yl, 1,2,4-triazolin-3-yl,
3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl,
2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl,
1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl,
1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,
1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,
1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;
[0087] 5-membered rings having four heteroatoms such as:
tetrazol-5-yl; [0088] 6-membered rings having one heteroatom such
as: tetrahydropyran-2-yl, tetrahydropyran-3-yl,
tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl,
piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,
tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl,
2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl,
2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,
2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl,
2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl,
2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl,
1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl,
1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl,
2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl,
2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl,
2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl,
2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl,
2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl,
1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl,
1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl,
1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl,
2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl,
2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl,
4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl,
4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl,
1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl,
2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,
2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,
2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl,
1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl,
1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl,
3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl,
3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl,
3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl,
2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,
2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl,
2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl,
2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl,
2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or
pyridin-4-yl; [0089] 6-membered rings having two heteroatoms such
as: 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl,
1,4-dioxan-2-yl, 1,3-dithian-2-yl,
1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl,
1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,
1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl,
1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl,
hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl,
hexahydropyrazin-2-yl, hexahydropyridazin-3-yl,
hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl,
tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl,
tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl,
tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl,
tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl,
tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl,
tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl,
tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl,
tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl,
2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl,
2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl,
2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl,
2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl,
4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl,
4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl,
4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl,
4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl,
2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl,
2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl,
2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl,
2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl,
2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl,
2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl,
2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl,
2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl,
2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl,
2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl,
3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl,
1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl,
1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl,
1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl,
4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl,
4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl,
4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl,
4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl,
3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl,
3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl,
1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl,
1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl,
1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl,
2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl,
2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl,
2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl,
2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl,
2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl,
4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl,
4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl,
6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl,
6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl,
6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl,
2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl,
2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl,
2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl,
4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl,
4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl,
6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl,
6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl,
6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl,
2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl,
2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl,
2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl,
4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,
1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,
1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,
1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,
1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,
1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,
1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,
1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,
3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or
3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,
pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;
[0090] 6-membered rings having three heteroatoms such as:
1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,
1,2,4-triazin-6-yl; [0091] 6-membered rings having four heteroatoms
such as: 1,2,4,5-tetrazin-3-yl; [0092] where, if appropriate, the
sulfur of the above-mentioned heterocycles may be oxidized to
S.dbd.O or S(.dbd.O).sub.2 [0093] and where a bicyclic ring system
may be formed with a fused-on phenyl ring or with a
C.sub.3-C.sub.6-carbocycle or with a further 5- to 6-membered
heterocycle. [0094] N-bonded heterocyclyl: a saturated, partially
saturated or unsaturated 5- or 6-membered heterocyclic ring which
is attached via nitrogen and contains at least one nitrogen and, if
appropriate, one to three identical or different heteroatoms
selected from the following group: oxygen, sulfur and nitrogen,
i.e., for example, [0095] N-bonded 5-membered rings such as:
tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,
2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl,
tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl,
tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl,
tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl,
2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl,
2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl,
2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl,
4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl,
2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl,
2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl,
1,2,4-.DELTA..sup.4-oxadiazolin-2-yl,
1,2,4-.DELTA..sup.2-oxadiazolin-4-yl,
1,2,4-.DELTA..sup.3-oxadiazolin-2-yl,
1,3,4-.DELTA..sup.2-oxadiazolin-4-yl,
1,2,4-.DELTA..sup.5-thiadiazolin-2-yl,
1,2,4-.DELTA..sup.3-thiadiazolin-2-yl,
1,2,4-.DELTA..sup.2-thiadiazolin-4-yl,
1,3,4-.DELTA..sup.2-thiadiazolin-4-yl,
1,2,3-.DELTA..sup.2-triazolin-1-yl,
1,2,4-.DELTA..sup.2-triazolin-1-yl,
1,2,4-.DELTA..sup.2-triazolin-4-yl,
1,2,4-.DELTA..sup.3-triazolin-1-yl,
1,2,4-.DELTA..sup.1-triazolin-4-yl, 1,2,3-triazol-1-yl,
1,2,4-triazol-1-yl, tetrazol-1-yl; [0096] and also N-bonded
6-membered rings such as: piperidin-1-yl,
1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl,
1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl,
hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl,
hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl,
tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl,
tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl,
2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl,
2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl,
2H-3,4-dihydro-1,2-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl,
2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl,
1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl,
3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl,
1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl,
2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl,
2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl,
1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl,
1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or
3,4-dihydropyrimidin-3-yl; [0097] and also N-bonded cyclic imides
such as: [0098] phthalimide, tetrahydrophthalimide, succinimide,
maleimide, glutarimide, 5-oxotriazolin-1-yl,
5-oxo-1,3,4-oxadiazolin-4-yl or 2,4-dioxo-(1H,3H)-pyrimidin-3-yl;
[0099] where a bicyclic ring system may be formed with a fused-on
phenyl ring or with a C.sub.3-C.sub.6-carbocycle or a further 5- to
6-membered heterocycle.
[0100] All phenyl rings, heterocyclyl or N-heterocyclyl radicals
and all phenyl components in phenoxy, phenyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl,
phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,
phenylaminocarbonyl and
N--(C.sub.1-C.sub.6-alkyl)-N-phenylaminocarbonyl or heterocyclyl
components in heterocyclyloxy, heterocyclyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl, heterocyclylcarbonyl,
heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl,
heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and
N--(C.sub.1-C.sub.6-alkyl)-N-heterocyclylaminocarbonyl are, unless
stated otherwise, preferably unsubstituted, or they carry one to
three halogen atoms and/or one nitro group, one cyano radical
and/or one or two methyl, trifluoromethyl, methoxy or
trifluoromethoxy substitutents.
[0101] Furthermore, the expression "Y together with the two carbons
to which it is attached forms a saturated, partially saturated or
unsaturated heterocycle which contains one to three identical or
different heteroatoms selected from the following group: oxygen,
sulfur and nitrogen" denotes, for example, 5-membered rings having
one heteroatom such as:
tetrahydrofurandiyl, tetrahydrothienediyl, tetrahydropyrrolediyl,
dihydrofurandiyl, dihydrothienediyl, dihydropyrrolediyl, furandiyl,
thienediyl or pyrrolediyl;
or 5-membered rings having two heteroatoms such as:
[0102] tetrahydropyrazolediyl, tetrahydroisoxazolediyl,
1,2-oxathiolanediyl, tetrahydroisothiazolediyl, 1,2-dithiolanediyl,
tetrahydroimidazolediyl, tetrahydrooxazolediyl,
tetrahydrothiazolediyl, 1,3-dioxolanediyl, 1,3-oxathiolanediyl,
dihydropyrazolediyl, dihydroisoxazolediyl, dihydroisothiazolediyl,
1,2-dithiolediyl, dihydroimidazolediyl, dihydrooxazolediyl,
dihydrothiazolediyl, dioxolediyl, oxathiolediyl, pyrazolediyl,
isoxazolediyl, isothiazolediyl, imidazolediyl, oxazolediyl or
thiazolediyl;
or 5-membered rings having three heteroatoms such as:
1,2,3-oxadiazolinediyl, 1,2,3-thiadiazolinediyl,
1,2,3-triazolinediyl, 1,2,3-oxadiazolediyl, 1,2,3-thiadiazolediyl
or 1,2,3-triazolediyl;
or 6-membered rings having one heteroatom such as:
tetrahydropyrandiyl, piperidinediyl, tetrahydrothiopyrandiyl,
dihydropyrandiyl, dihydrothiopyrandiyl, tetrahydropyridinediyl,
pyrandiyl, thiopyrandiyl, dihydropyrinediyl or pyridinediyl;
or 6-membered rings having two heteroatoms such as:
[0103] 1,3-dioxanediyl, 1,4-dioxanediyl, 1,3-dithianediyl,
1,4-dithianediyl, 1,3-oxathianediyl, 1,4-oxathianediyl,
1,2-dithianediyl, hexahydropyrimidinediyl, hexahydropyrazinediyl,
hexahydropyridazinediyl, tetrahydro-1,3-oxazinediyl,
tetrahydro-1,3-thiazinediyl, tetrahydro-1,4-oxazinediyl,
tetrahydro-1,2-oxazinediyl, dihydro-1,2-oxazinediyl,
dihydro-1,2-thiazinediyl, tetrahydropyridazinediyl,
dihydro-1,3-oxazinediyl, dihydro-1,3-oxazinediyl,
dihydro-1,3-thiazinediyl, tetrahydropyrimidinediyl,
tetrahydropyrazinediyl, dihydro-1,4-thiazinediyl,
dihydro-1,4-oxazinediyl, dihydro-1,4-dioxinediyl,
dihydro-1,4-dithiinediyl, 1,2-oxazinediyl, 1,2-thiazinediyl,
1,3-oxazinediyl, 1,3-thiazinediyl, 1,4-oxazinediyl,
1,4-thiazinediyl, dihydropyridazinediyl, dihydropyrazinediyl,
dihydropyrimidinediyl, pyridazinediyl, pyrimidinediyl or
pyrazinediyl;
or 6-membered rings having 3 heteroatoms such as:
1,2,4-triazinediyl;
where, if appropriate, the sulfur of the abovementioned
heterocycles may be oxidized to S.dbd.O or S(.dbd.O).sub.2;
and where the moiety is fused to the skeleton via two adjacent
carbon atoms.
[0104] The compounds of the formula I according to the invention
where R.sup.9=IIa are referred to as compounds of the formula Ia,
and compounds of the formula I where R.sup.9=IIb are referred to as
Ib.
[0105] Preference is given to the compounds of the formula I, where
[0106] R.sup.11 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, hydroxyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy;
[0107] Preference is likewise given to the compounds of the formula
Ia.
[0108] With respect to the use of the compounds of the formula I
according to the invention as herbicides, the variables preferably
have the following meanings, in each case alone or in combination:
[0109] X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2,
CR.sup.6R.sup.7, NR.sup.8 or a bond; [0110] Y together with the two
carbons to which it is attached forms a saturated, partially
saturated or unsaturated 5- or 6-membered heterocycle which
contains one or two identical or different heteroatoms selected
from the following group: oxygen, sulfur or nitrogen; [0111]
R.sup.1, R.sup.2 are hydrogen or C.sub.1-C.sub.6-alkyl; [0112]
R.sup.3 is halogen, C.sub.1-C.sub.6-alkyl or
C.sub.1-C.sub.6-alkoxy; [0113] R.sup.4 is nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
[0114] in particular nitro, halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl; [0115] R.sup.5 is hydrogen;
[0116] R.sup.6, R.sup.7 are hydrogen or C.sub.1-C.sub.6-alkyl;
[0117] R.sup.8 is C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkylcarbonyl or C.sub.1-C.sub.6-alkylsulfonyl;
[0118] l is 0, 1 or 2; [0119] R.sup.9 is a radical IIa ##STR6##
where [0120] R.sup.10 is hydroxyl, mercapto, halogen, OR.sup.13,
SR.sup.13, SO.sub.2R.sup.14 or N-bonded heterocyclyl, where the
heterocyclyl radical may be partially or fully halogenated and/or
may carry one to three of the following radicals: [0121] nitro,
cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; [0122]
R.sup.11 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl or C.sub.3-C.sub.6-cycloalkyl; [0123]
R.sup.12 is hydrogen, C.sub.1-C.sub.6-alkyl or
C.sub.1-C.sub.6-haloalkyl; [0124] R.sup.13 is
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl,
C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl,
C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)
aminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkoxy)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl,
C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl or
N,N-di(C.sub.1-C.sub.6-alkylamino)imino-C.sub.1-C.sub.6-alkyl,
where the abovementioned alkyl, cycloalkyl and alkoxy radicals may
be partially or fully halogenated and/or may carry one to three of
the following groups: [0125] cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl, hydroxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl;
[0126] is phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl,
heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,
phenyl-C.sub.2-C.sub.6-alkenylcarbonyl or
heterocyclyl-C.sub.2-C.sub.6-alkenylcarbonyl, where the phenyl and
the heterocyclyl radical of the 14 lastmentioned substitutents may
be partially or fully halogenated and/or may carry one to three of
the following radicals: [0127] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl,
where the two lastmentioned substitutents for their part may be
partially or fully halogenated and/or may carry one to three of the
following radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0128] R.sup.14 is
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy or di(C.sub.1-C.sub.6-haloalkyl)amino, where
the abovementioned alkyl, cycloalkyl and alkoxy radicals may be
partially or fully halogenated and/or may carry one to three of the
following groups: [0129] cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl, hydroxycarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl,
C.sub.1-C.sub.4-alkylcarbonyloxy or C.sub.3-C.sub.6-cycloalkyl;
[0130] is phenyl, heterocyclyl, phenyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl, phenoxy, heterocyclyloxy, where
the phenyl and the heterocyclyl radical of the lastmentioned
substitutents may be partially or fully halogenated and/or may
carry one to three of the following radicals: [0131] nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy.
[0132] Particular preference is given to compounds of the formula I
where the variables have the following meanings, either alone or in
combination: [0133] X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2,
CR.sup.6R.sup.7 or a bond; [0134] Y together with the two carbons
to which it is attached forms the following heterocycles: [0135]
(in the embodiments of the heterocycles below, the upper undulating
line represents in each case the link to the hydrocarbon which
carries the radicals R.sup.1 and R.sup.2, and the lower undulating
line represents the link to the meta-carbon of the benzoyl moiety).
##STR7## ##STR8## where the sulfur of the abovementioned
heterocycles may be oxidized to S.dbd.O or S(.dbd.O).sub.2; in
particular, Y together with the two carbons to which it is attached
forms the following heterocycles: ##STR9## ##STR10## [0136]
R.sup.1, R.sup.2 are hydrogen; [0137] R.sup.3 is
C.sub.1-C.sub.6-alkyl, such as methyl, ethyl or n-propyl; in
particular methyl; [0138] R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; in particular nitro, halogen, such
as fluorine, chlorine or bromine, C.sub.1-C.sub.6-haloalkyl such as
trifluoromethyl, C.sub.1-C.sub.6-alkylthio, such as methylthio or
ethylthio, or C.sub.1-C.sub.6-alkylsulfonyl, such as methylsulfonyl
or ethylsulfonyl; [0139] particularly preferably nitro, chlorine,
trifluoromethyl, methylthio or methylsulfonyl; [0140] R.sup.5 is
hydrogen; [0141] R.sup.6, R.sup.7 are hydrogen or
C.sub.1-C.sub.6-alkyl, such as methyl or ethyl; [0142] in
particular hydrogen or methyl; [0143] l is 0, 1 or 2; [0144] in
particular 0 or 1; [0145] R.sup.9 is a radical IIa ##STR11## where
[0146] R.sup.10 is hydroxyl; [0147] R.sup.11 is
C.sub.1-C.sub.6-alkyl, such as methyl, ethyl, n-propyl,
1-methylethyl, n-butyl, 2-methylpropyl or 1,1-dimethylethyl or
cyclopropyl; [0148] in particular methyl or ethyl; [0149] likewise
particularly preferred cyclopropyl; [0150] R.sup.12 is hydrogen or
C.sub.1-C.sub.6-alkyl, such as methyl, ethyl, n-propyl or
1-methylethyl; [0151] in particular hydrogen or methyl.
[0152] Very particular preference is given to the compounds 1a
where [0153] X is oxygen, sulfur, S(.dbd.O).sub.2, CH.sub.2 or a
bond; [0154] Y together with the two carbons to which it is
attached forms the following heterocycles: ##STR12## [0155]
R.sup.1, R.sup.2 are hydrogen; [0156] R.sup.3 is
C.sub.1-C.sub.4-alkyl; [0157] R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; [0158] R.sup.5 is hydrogen or
C.sub.1-C.sub.6-alkyl; [0159] l is 0, 1 or 2; [0160] R.sup.9 is a
radical IIa; [0161] R.sup.10 is hydroxyl; [0162] R.sup.11 is
hydrogen, C.sub.1-C.sub.6-alkyl or cyclopropyl; [0163] in
particular C.sub.1-C.sub.6-alkyl; [0164] R.sup.12 is hydrogen,
C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl.
[0165] Very particular preference is also given to the compounds Ia
where X is oxygen, sulfur or a bond.
[0166] Very particular preference is also given to the compounds 1a
where [0167] Y together with the two carbons to which it is
attached forms a heterocycle selected from the following group:
dihydropyrazolediyl, dihydroisoxazolediyl, pyrazolediyl,
isoxazolediyl or pyrimidinediyl.
[0168] Most preferably, Y together with the two carbons to which it
is attached forms the following heterocycles: ##STR13##
[0169] Very particular preference is also given to the compounds of
the formula I where [0170] R.sup.1, R.sup.2 are hydrogen; [0171]
R.sup.3 is C.sub.1-C.sub.6-alkyl; [0172] R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; [0173] in particular halogen,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; [0174] R.sup.5 is hydrogen; [0175] l
is 0 oder 1.
[0176] Very particular preference is also given to the compounds of
the formula I where [0177] R.sup.10 is hydroxyl or
phenylcarbonyloxy which may be unsubstituted or partially or fully
halogenated and/or may carry one to three of the following
radicals: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0178] in particular hydroxyl; [0179]
R.sup.11 is C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl;
[0180] in particular C.sub.1-C.sub.6-alkyl or [0181] also in
particular cyclopropyl; [0182] R.sup.12 is hydrogen or
C.sub.1-C.sub.6-alkyl; [0183] in particular hydrogen.
[0184] Very particular preference is also given to the compounds of
the formula Ia1 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0, meaning of the heterocycle according to structural
formula), most particularly to compounds Ia1.n where the variables
X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table 1.
[0185] The radical definitions of R.sup.1 to R.sup.12, X, Y and l
given above and the meaning of the fused heterocycle are of
particular importance for the compounds according to the invention,
not only in combination with one another, but also taken on their
own. (For reasons of clarity, in the formulae Ia1, Ia2 . . . , the
meaning of the fused heterocycle is in each case as given in the
corresponding structural formula.) TABLE-US-00001 TABLE 1 Ia1
##STR14## n X R.sup.4 R.sup.10 R.sup.11 1 bond F OH CH.sub.3 2 bond
Cl OH CH.sub.3 3 bond Br OH CH.sub.3 4 bond NO.sub.2 OH CH.sub.3 5
bond SCH.sub.3 OH CH.sub.3 6 bond SO.sub.2CH.sub.3 OH CH.sub.3 7
bond SO.sub.2CH.sub.2CH.sub.3 OH CH.sub.3 8 bond CH.sub.3 OH
CH.sub.3 9 bond CF.sub.3 OH CH.sub.3 10 bond OCHF.sub.2 OH CH.sub.3
11 CH.sub.2 F OH CH.sub.3 12 CH.sub.2 Cl OH CH.sub.3 13 CH.sub.2 Br
OH CH.sub.3 14 CH.sub.2 NO.sub.2 OH CH.sub.3 15 CH.sub.2 SCH.sub.3
OH CH.sub.3 16 CH.sub.2 SO.sub.2CH.sub.3 OH CH.sub.3 17 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH CH.sub.3 18 CH.sub.2 CH.sub.3 OH
CH.sub.3 19 CH.sub.2 CF.sub.3 OH CH.sub.3 20 CH.sub.2 OCHF.sub.2 OH
CH.sub.3 21 O F OH CH.sub.3 22 O Cl OH CH.sub.3 23 O Br OH CH.sub.3
24 O NO.sub.2 OH CH.sub.3 25 O SCH.sub.3 OH CH.sub.3 26 O
SO.sub.2CH.sub.3 OH CH.sub.3 27 O SO.sub.2CH.sub.2CH.sub.3 OH
CH.sub.3 28 O CH.sub.3 OH CH.sub.3 29 O CF.sub.3 OH CH.sub.3 30 O
OCHF.sub.2 OH CH.sub.3 31 S F OH CH.sub.3 32 S Cl OH CH.sub.3 33 S
Br OH CH.sub.3 34 S NO.sub.2 OH CH.sub.3 35 S SCH.sub.3 OH CH.sub.3
36 S SO.sub.2CH.sub.3 OH CH.sub.3 37 S SO.sub.2CH.sub.2CH.sub.3 OH
CH.sub.3 38 S CH.sub.3 OH CH.sub.3 39 S CF.sub.3 OH CH.sub.3 40 S
OCHF.sub.2 OH CH.sub.3 41 SO.sub.2 F OH CH.sub.3 42 SO.sub.2 Cl OH
CH.sub.3 43 SO.sub.2 Br OH CH.sub.3 44 SO.sub.2 NO.sub.2 OH
CH.sub.3 45 SO.sub.2 SCH.sub.3 OH CH.sub.3 46 SO.sub.2
SO.sub.2CH.sub.3 OH CH.sub.3 47 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OH CH.sub.3 48 SO.sub.2 CH.sub.3 OH CH.sub.3 49 SO.sub.2 CF.sub.3
OH CH.sub.3 50 SO.sub.2 OCHF.sub.2 OH CH.sub.3 51 bond F OH
CH.sub.2CH.sub.3 52 bond Cl OH CH.sub.2CH.sub.3 53 bond Br OH
CH.sub.2CH.sub.3 54 bond NO.sub.2 OH CH.sub.2CH.sub.3 55 bond
SCH.sub.3 OH CH.sub.2CH.sub.3 56 bond SO.sub.2CH.sub.3 OH
CH.sub.2CH.sub.3 57 bond SO.sub.2CH.sub.2CH.sub.3 OH
CH.sub.2CH.sub.3 58 bond CH.sub.3 OH CH.sub.2CH.sub.3 59 bond
CF.sub.3 OH CH.sub.2CH.sub.3 60 bond OCHF.sub.2 OH CH.sub.2CH.sub.3
61 CH.sub.2 F OH CH.sub.2CH.sub.3 62 CH.sub.2 Cl OH
CH.sub.2CH.sub.3 63 CH.sub.2 Br OH CH.sub.2CH.sub.3 64 CH.sub.2
NO.sub.2 OH CH.sub.2CH.sub.3 65 CH.sub.2 SCH.sub.3 OH
CH.sub.2CH.sub.3 66 CH.sub.2 SO.sub.2CH.sub.3 OH CH.sub.2CH.sub.3
67 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 68
CH.sub.2 CH.sub.3 OH CH.sub.2CH.sub.3 69 CH.sub.2 CF.sub.3 OH
CH.sub.2CH.sub.3 70 CH.sub.2 OCHF.sub.2 OH CH.sub.2CH.sub.3 71 O F
OH CH.sub.2CH.sub.3 72 O Cl OH CH.sub.2CH.sub.3 73 O Br OH
CH.sub.2CH.sub.3 74 O NO.sub.2 OH CH.sub.2CH.sub.3 75 O SCH.sub.3
OH CH.sub.2CH.sub.3 76 O SO.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 77 O
SO.sub.2CH.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 78 O CH.sub.3 OH
CH.sub.2CH.sub.3 79 O CF.sub.3 OH CH.sub.2CH.sub.3 80 O OCHF.sub.2
OH CH.sub.2CH.sub.3 81 S F OH CH.sub.2CH.sub.3 82 S Cl OH
CH.sub.2CH.sub.3 83 S Br OH CH.sub.2CH.sub.3 84 S NO.sub.2 OH
CH.sub.2CH.sub.3 85 S SCH.sub.3 OH CH.sub.2CH.sub.3 86 S
SO.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 87 S SO.sub.2CH.sub.2CH.sub.3
OH CH.sub.2CH.sub.3 88 S CH.sub.3 OH CH.sub.2CH.sub.3 89 S CF.sub.3
OH CH.sub.2CH.sub.3 90 S OCHF.sub.2 OH CH.sub.2CH.sub.3 91 SO.sub.2
F OH CH.sub.2CH.sub.3 92 SO.sub.2 Cl OH CH.sub.2CH.sub.3 93
SO.sub.2 Br OH CH.sub.2CH.sub.3 94 SO.sub.2 NO.sub.2 OH
CH.sub.2CH.sub.3 95 SO.sub.2 SCH.sub.3 OH CH.sub.2CH.sub.3 96
SO.sub.2 SO.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 97 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH CH.sub.2CH.sub.3 98 SO.sub.2 CH.sub.3
OH CH.sub.2CH.sub.3 99 SO.sub.2 CF.sub.3 OH CH.sub.2CH.sub.3 100
SO.sub.2 OCHF.sub.2 OH CH.sub.2CH.sub.3 101 bond F
OCOC.sub.6H.sub.5 CH.sub.3 102 bond Cl OCOC.sub.6H.sub.5 CH.sub.3
103 bond Br OCOC.sub.6H.sub.5 CH.sub.3 104 bond NO.sub.2
OCOC.sub.6H.sub.5 CH.sub.3 105 bond SCH.sub.3 OCOC.sub.6H.sub.5
CH.sub.3 106 bond SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 107
bond SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 108 bond
CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 109 bond CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 110 bond OCHF.sub.2 OCOC.sub.6H.sub.5
CH.sub.3 111 CH.sub.2 F OCOC.sub.6H.sub.5 CH.sub.3 112 CH.sub.2 Cl
OCOC.sub.6H.sub.5 CH.sub.3 113 CH.sub.2 Br OCOC.sub.6H.sub.5
CH.sub.3 114 CH.sub.2 NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.3 115
CH.sub.2 SCH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 116 CH.sub.2
SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 117 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 118 CH.sub.2
CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 119 CH.sub.2 CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 120 CH.sub.2 OCHF.sub.2
OCOC.sub.6H.sub.5 CH.sub.3 121 O F OCOC.sub.6H.sub.5 CH.sub.3 122 O
Cl OCOC.sub.6H.sub.5 CH.sub.3 123 O Br OCOC.sub.6H.sub.5 CH.sub.3
124 O NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.3 125 O SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 126 O SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5
CH.sub.3 127 O SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3
128 O CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 129 O CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 130 O OCHF.sub.2 OCOC.sub.6H.sub.5
CH.sub.3 131 S F OCOC.sub.6H.sub.5 CH.sub.3 132 S Cl
OCOC.sub.6H.sub.5 CH.sub.3 133 S Br OCOC.sub.6H.sub.5 CH.sub.3 134
S NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.3 135 S SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 136 S SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5
CH.sub.3 137 S SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3
138 S CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 139 S CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 140 S OCHF.sub.2 OCOC.sub.6H.sub.5
CH.sub.3 141 SO.sub.2 F OCOC.sub.6H.sub.5 CH.sub.3 142 SO.sub.2 Cl
OCOC.sub.6H.sub.5 CH.sub.3 143 SO.sub.2 Br OCOC.sub.6H.sub.5
CH.sub.3 144 SO.sub.2 NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.3 145
SO.sub.2 SCH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 146 SO.sub.2
SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 147 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 148 SO.sub.2
CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.3 149 SO.sub.2 CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.3 150 SO.sub.2 OCHF.sub.2
OCOC.sub.6H.sub.5 CH.sub.3 151 bond F OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 152 bond Cl OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 153
bond Br OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 154 bond NO.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 155 bond SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 156 bond SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 157 bond
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 158
bond CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 159 bond CF.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 160 bond OCHF.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 161 CH.sub.2 F OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 162 CH.sub.2 Cl OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3
163 CH.sub.2 Br OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 164 CH.sub.2
NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 165 CH.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 166 CH.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 167 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 168
CH.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 169 CH.sub.2
CF.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 170 CH.sub.2 OCHF.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 171 O F OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 172 O Cl OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 173 O
Br OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 174 O NO.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 175 O SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 176 O SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 177 O SO.sub.2CH.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 178 O CH.sub.3 OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 179 O CF.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3
180 O OCHF.sub.2 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 181 S F
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 182 S Cl OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 183 S Br OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 184 S
NO.sub.2 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 185 S SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 186 S SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 187 S SO.sub.2CH.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 188 S CH.sub.3 OCOC.sub.6H.sub.5
CH.sub.2CH.sub.3 189 S CF.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3
190 S OCHF.sub.2 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 191 SO.sub.2 F
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 192 SO.sub.2 Cl
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 193 SO.sub.2 Br
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 194 SO.sub.2 NO.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 195 SO.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 196 SO.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 197 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 198
SO.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 199 SO.sub.2
CF.sub.3 OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 200 SO.sub.2 OCHF.sub.2
OCOC.sub.6H.sub.5 CH.sub.2CH.sub.3 201 bond F OCOC(CH.sub.3).sub.3
CH.sub.3 202 bond Cl OCOC(CH.sub.3).sub.3 CH.sub.3 203 bond Br
OCOC(CH.sub.3).sub.3 CH.sub.3 204 bond NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 205 bond SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 206 bond SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 207 bond SO.sub.2CH.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 208 bond CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 209 bond CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 210 bond OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 211 CH.sub.2 F OCOC(CH.sub.3).sub.3
CH.sub.3 212 CH.sub.2 Cl OCOC(CH.sub.3).sub.3 CH.sub.3 213 CH.sub.2
Br OCOC(CH.sub.3).sub.3 CH.sub.3 214 CH.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 215 CH.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 216 CH.sub.2 SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 217 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 218 CH.sub.2 CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 219 CH.sub.2 CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 220 CH.sub.2 OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 221 O F OCOC(CH.sub.3).sub.3 CH.sub.3
222 O Cl OCOC(CH.sub.3).sub.3 CH.sub.3 223 O Br
OCOC(CH.sub.3).sub.3 CH.sub.3 224 O NO.sub.2 OCOC(CH.sub.3).sub.3
CH.sub.3 225 O SCH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 226 O
SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 227 O
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 228 O
CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 229 O CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 230 O OCHF.sub.2 OCOC(CH.sub.3).sub.3
CH.sub.3 231 S F OCOC(CH.sub.3).sub.3 CH.sub.3 232 S Cl
OCOC(CH.sub.3).sub.3 CH.sub.3 233 S Br OCOC(CH.sub.3).sub.3
CH.sub.3 234 S NO.sub.2 OCOC(CH.sub.3).sub.3 CH.sub.3 235 S
SCH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 236 S SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3
237 S SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 238 S
CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.3 239 S CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 240 S OCHF.sub.2 OCOC(CH.sub.3).sub.3
CH.sub.3 241 SO.sub.2 F OCOC(CH.sub.3).sub.3 CH.sub.3 242 SO.sub.2
Cl OCOC(CH.sub.3).sub.3 CH.sub.3 243 SO.sub.2 Br
OCOC(CH.sub.3).sub.3 CH.sub.3 244 SO.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 245 SO.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 246 SO.sub.2 SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 247 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 248 SO.sub.2 CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 249 SO.sub.2 CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.3 250 SO.sub.2 OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.3 251 bond F OCOC(CH.sub.3).sub.3
CH.sub.2CH.sub.3 252 bond Cl OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3
253 bond Br OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 254 bond NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 255 bond SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 256 bond SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 257 bond
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 258
bond CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 259 bond
CF.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 260 bond OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 261 CH.sub.2 F
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 262 CH.sub.2 Cl
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 263 CH.sub.2 Br
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 264 CH.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 265 CH.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 266 CH.sub.2 SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 267 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 268
CH.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 269
CH.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 270
CH.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 271 O F
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 272 O Cl OCOC(CH.sub.3).sub.3
CH.sub.2CH.sub.3 273 O Br OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 274
O NO.sub.2 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 275 O SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 276 O SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 277 O
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 278
O CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 279 O CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 280 O OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 281 S F OCOC(CH.sub.3).sub.3
CH.sub.2CH.sub.3 282 S Cl OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 283
S Br OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 284 S NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 285 S SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 286 S SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 287 S
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 288
S CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 289 S CF.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 290 S OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 291 SO.sub.2 F
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 292 SO.sub.2 Cl
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 293 SO.sub.2 Br
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 294 SO.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 295 SO.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 296 SO.sub.2 SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 297 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 298
SO.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 299
SO.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 300
SO.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3 CH.sub.2CH.sub.3 301 bond
F OCOSCH.sub.3 CH.sub.3 302 bond Cl OCOSCH.sub.3 CH.sub.3 303 bond
Br OCOSCH.sub.3 CH.sub.3 304 bond NO.sub.2 OCOSCH.sub.3 CH.sub.3
305 bond SCH.sub.3 OCOSCH.sub.3 CH.sub.3 306 bond SO.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.3 307 bond SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.3 308 bond CH.sub.3 OCOSCH.sub.3 CH.sub.3 309
bond CF.sub.3 OCOSCH.sub.3 CH.sub.3 310 bond OCHF.sub.2
OCOSCH.sub.3 CH.sub.3 311 CH.sub.2 F OCOSCH.sub.3 CH.sub.3 312
CH.sub.2 Cl OCOSCH.sub.3 CH.sub.3 313 CH.sub.2 Br OCOSCH.sub.3
CH.sub.3 314 CH.sub.2 NO.sub.2 OCOSCH.sub.3 CH.sub.3 315 CH.sub.2
SCH.sub.3 OCOSCH.sub.3 CH.sub.3 316 CH.sub.2 SO.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.3 317 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.3 318 CH.sub.2 CH.sub.3 OCOSCH.sub.3 CH.sub.3
319 CH.sub.2 CF.sub.3 OCOSCH.sub.3 CH.sub.3 320 CH.sub.2 OCHF.sub.2
OCOSCH.sub.3 CH.sub.3 321 O F OCOSCH.sub.3 CH.sub.3 322 O Cl
OCOSCH.sub.3 CH.sub.3 323 O Br OCOSCH.sub.3 CH.sub.3 324 O NO.sub.2
OCOSCH.sub.3 CH.sub.3 325 O SCH.sub.3 OCOSCH.sub.3 CH.sub.3 326 O
SO.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 327 O
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 328 O CH.sub.3
OCOSCH.sub.3 CH.sub.3 329 O CF.sub.3 OCOSCH.sub.3 CH.sub.3 330 O
OCHF.sub.2 OCOSCH.sub.3 CH.sub.3 331 S F OCOSCH.sub.3 CH.sub.3 332
S Cl OCOSCH.sub.3 CH.sub.3 333 S Br OCOSCH.sub.3 CH.sub.3 334 S
NO.sub.2 OCOSCH.sub.3 CH.sub.3 335 S SCH.sub.3 OCOSCH.sub.3
CH.sub.3 336 S SO.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 337 S
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 338 S CH.sub.3
OCOSCH.sub.3 CH.sub.3 339 S CF.sub.3 OCOSCH.sub.3 CH.sub.3 340 S
OCHF.sub.2 OCOSCH.sub.3 CH.sub.3 341 SO.sub.2 F OCOSCH.sub.3
CH.sub.3 342 SO.sub.2 Cl OCOSCH.sub.3 CH.sub.3 343 SO.sub.2 Br
OCOSCH.sub.3 CH.sub.3 344 SO.sub.2 NO.sub.2 OCOSCH.sub.3 CH.sub.3
345 SO.sub.2 SCH.sub.3 OCOSCH.sub.3 CH.sub.3 346 SO.sub.2
SO.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 347 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.3 348 SO.sub.2
CH.sub.3 OCOSCH.sub.3 CH.sub.3 349 SO.sub.2 CF.sub.3 OCOSCH.sub.3
CH.sub.3 350 SO.sub.2 OCHF.sub.2 OCOSCH.sub.3 CH.sub.3 351 bond F
OCOSCH.sub.3 CH.sub.2CH.sub.3 352 bond Cl OCOSCH.sub.3
CH.sub.2CH.sub.3 353 bond Br OCOSCH.sub.3 CH.sub.2CH.sub.3 354 bond
NO.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 355 bond SCH.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 356 bond SO.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 357 bond SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 358 bond CH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 359 bond CF.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3
360 bond OCHF.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 361 CH.sub.2 F
OCOSCH.sub.3 CH.sub.2CH.sub.3 362 CH.sub.2 Cl OCOSCH.sub.3
CH.sub.2CH.sub.3 363 CH.sub.2 Br OCOSCH.sub.3 CH.sub.2CH.sub.3 364
CH.sub.2 NO.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 365 CH.sub.2
SCH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 366 CH.sub.2
SO.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 367 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 368 CH.sub.2
CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 369 CH.sub.2 CF.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 370 CH.sub.2 OCHF.sub.2 OCOSCH.sub.3
CH.sub.2CH.sub.3 371 O F OCOSCH.sub.3 CH.sub.2CH.sub.3 372 O Cl
OCOSCH.sub.3 CH.sub.2CH.sub.3 373 O Br OCOSCH.sub.3
CH.sub.2CH.sub.3 374 O NO.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 375 O
SCH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 376 O SO.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 377 O SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH.sub.2CH.sub.3 378 O CH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 379 O CF.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 380 O
OCHF.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 381 S F OCOSCH.sub.3
CH.sub.2CH.sub.3 382 S Cl OCOSCH.sub.3 CH.sub.2CH.sub.3 383 S Br
OCOSCH.sub.3 CH.sub.2CH.sub.3 384 S NO.sub.2 OCOSCH.sub.3
CH.sub.2CH.sub.3 385 S SCH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 386
S SO.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 387 S
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 388 S
CH.sub.3 OCOSCH.sub.3 CH.sub.2CH.sub.3 389 S CF.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 390 S OCHF.sub.2 OCOSCH.sub.3 CH.sub.2CH.sub.3 391
SO.sub.2 F OCOSCH.sub.3 CH.sub.2CH.sub.3 392 SO.sub.2 Cl
OCOSCH.sub.3 CH.sub.2CH.sub.3 393 SO.sub.2 Br OCOSCH.sub.3
CH.sub.2CH.sub.3 394 SO.sub.2 NO.sub.2 OCOSCH.sub.3
CH.sub.2CH.sub.3 395 SO.sub.2 SCH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 396 SO.sub.2 SO.sub.2CH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 397 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 398 SO.sub.2 CH.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 399 SO.sub.2 CF.sub.3 OCOSCH.sub.3
CH.sub.2CH.sub.3 400 SO.sub.2 OCHF.sub.2 OCOSCH.sub.3
CH.sub.2CH.sub.3 401 bond F OCH.sub.3 CH.sub.3 402 bond Cl
OCH.sub.3 CH.sub.3 403 bond Br OCH.sub.3 CH.sub.3 404 bond NO.sub.2
OCH.sub.3 CH.sub.3 405 bond SCH.sub.3 OCH.sub.3 CH.sub.3 406 bond
SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 407 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 408 bond CH.sub.3
OCH.sub.3 CH.sub.3 409 bond CF.sub.3 OCH.sub.3 CH.sub.3 410 bond
OCHF.sub.2 OCH.sub.3 CH.sub.3 411 CH.sub.2 F OCH.sub.3 CH.sub.3 412
CH.sub.2 Cl OCH.sub.3 CH.sub.3 413 CH.sub.2 Br OCH.sub.3 CH.sub.3
414 CH.sub.2 NO.sub.2 OCH.sub.3 CH.sub.3 415 CH.sub.2 SCH.sub.3
OCH.sub.3 CH.sub.3 416 CH.sub.2 SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3
417 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 418
CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 419 CH.sub.2 CF.sub.3
OCH.sub.3 CH.sub.3 420 CH.sub.2 OCHF.sub.2 OCH.sub.3 CH.sub.3 421 O
F OCH.sub.3 CH.sub.3 422 O Cl OCH.sub.3 CH.sub.3 423 O Br OCH.sub.3
CH.sub.3 424 O NO.sub.2 OCH.sub.3 CH.sub.3 425 O SCH.sub.3
OCH.sub.3 CH.sub.3 426 O SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 427 O
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 428 O CH.sub.3
OCH.sub.3 CH.sub.3 429 O CF.sub.3 OCH.sub.3 CH.sub.3 430 O
OCHF.sub.2 OCH.sub.3 CH.sub.3 431 S F OCH.sub.3 CH.sub.3 432 S Cl
OCH.sub.3 CH.sub.3 433 S Br OCH.sub.3 CH.sub.3 434 S NO.sub.2
OCH.sub.3 CH.sub.3 435 S SCH.sub.3 OCH.sub.3 CH.sub.3 436 S
SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 437 S SO.sub.2CH.sub.2CH.sub.3
OCH.sub.3 CH.sub.3 438 S CH.sub.3 OCH.sub.3 CH.sub.3 439 S CF.sub.3
OCH.sub.3 CH.sub.3 440 S OCHF.sub.2 OCH.sub.3 CH.sub.3 441 SO.sub.2
F OCH.sub.3 CH.sub.3 442 SO.sub.2 Cl OCH.sub.3 CH.sub.3 443
SO.sub.2 Br OCH.sub.3 CH.sub.3 444 SO.sub.2 NO.sub.2 OCH.sub.3
CH.sub.3 445 SO.sub.2 SCH.sub.3 OCH.sub.3 CH.sub.3 446 SO.sub.2
SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 447 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 448 SO.sub.2 CH.sub.3
OCH.sub.3 CH.sub.3 449 SO.sub.2 CF.sub.3 OCH.sub.3 CH.sub.3 450
SO.sub.2 OCHF.sub.2 OCH.sub.3 CH.sub.3 451 bond F OCH.sub.3
CH.sub.2CH.sub.3 452 bond Cl OCH.sub.3 CH.sub.2CH.sub.3 453 bond Br
OCH.sub.3 CH.sub.2CH.sub.3 454 bond NO.sub.2 OCH.sub.3
CH.sub.2CH.sub.3 455 bond SCH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 456
bond SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 457 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 458 bond
CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 459 bond CF.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 460 bond OCHF.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 461
CH.sub.2 F OCH.sub.3 CH.sub.2CH.sub.3 462 CH.sub.2 Cl OCH.sub.3
CH.sub.2CH.sub.3 463 CH.sub.2 Br OCH.sub.3 CH.sub.2CH.sub.3 464
CH.sub.2 NO.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 465 CH.sub.2 SCH.sub.3
OCH.sub.3 CH.sub.2CH.sub.3 466 CH.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 467 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 468 CH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3
469 CH.sub.2 CF.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 470 CH.sub.2
OCHF.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 471 O F OCH.sub.3
CH.sub.2CH.sub.3 472 O Cl OCH.sub.3 CH.sub.2CH.sub.3 473 O Br
OCH.sub.3 CH.sub.2CH.sub.3 474 O NO.sub.2 OCH.sub.3
CH.sub.2CH.sub.3 475 O SCH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 476 O
SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 477 O
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 478 O CH.sub.3
OCH.sub.3 CH.sub.2CH.sub.3 479 O CF.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 480 O OCHF.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 481 S
F OCH.sub.3 CH.sub.2CH.sub.3 482 S Cl OCH.sub.3 CH.sub.2CH.sub.3
483 S Br OCH.sub.3 CH.sub.2CH.sub.3 484 S NO.sub.2 OCH.sub.3
CH.sub.2CH.sub.3 485 S SCH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3
486 S SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 487 S
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 488 S CH.sub.3
OCH.sub.3 CH.sub.2CH.sub.3 489 S CF.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 490 S OCHF.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 491
SO.sub.2 F OCH.sub.3 CH.sub.2CH.sub.3 492 SO.sub.2 Cl OCH.sub.3
CH.sub.2CH.sub.3 493 SO.sub.2 Br OCH.sub.3 CH.sub.2CH.sub.3 494
SO.sub.2 NO.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 495 SO.sub.2 SCH.sub.3
OCH.sub.3 CH.sub.2CH.sub.3 496 SO.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 497 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
CH.sub.2CH.sub.3 498 SO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.2CH.sub.3
499 SO.sub.2 CF.sub.3 OCH.sub.3 CH.sub.2CH.sub.3 500 SO.sub.2
OCHF.sub.2 OCH.sub.3 CH.sub.2CH.sub.3 501 bond F
OCH(CH.sub.3).sub.2 CH.sub.3 502 bond Cl OCH(CH.sub.3).sub.2
CH.sub.3 503 bond Br OCH(CH.sub.3).sub.2 CH.sub.3 504 bond NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.3 505 bond SCH.sub.3 OCH(CH.sub.3).sub.2
CH.sub.3 506 bond SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 507
bond SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 508 bond
CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 509 bond CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 510 bond OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.3 511 CH.sub.2 F OCH(CH.sub.3).sub.2
CH.sub.3 512 CH.sub.2 Cl OCH(CH.sub.3).sub.2 CH.sub.3 513 CH.sub.2
Br OCH(CH.sub.3).sub.2 CH.sub.3 514 CH.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.3 515 CH.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 516 CH.sub.2 SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 517 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 518 CH.sub.2 CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 519 CH.sub.2 CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 520 CH.sub.2 OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.3 521 O F OCH(CH.sub.3).sub.2 CH.sub.3
522 O Cl OCH(CH.sub.3).sub.2 CH.sub.3 523 O Br OCH(CH.sub.3).sub.2
CH.sub.3 524 O NO.sub.2 OCH(CH.sub.3).sub.2 CH.sub.3 525 O
SCH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 526 O SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 527 O SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 528 O CH.sub.3 OCH(CH.sub.3).sub.2
CH.sub.3 529 O CF.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 530 O
OCHF.sub.2 OCH(CH.sub.3).sub.2 CH.sub.3 531 S F OCH(CH.sub.3).sub.2
CH.sub.3 532 S Cl OCH(CH.sub.3).sub.2 CH.sub.3 533 S Br
OCH(CH.sub.3).sub.2 CH.sub.3 534 S NO.sub.2 OCH(CH.sub.3).sub.2
CH.sub.3 535 S SCH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 536 S
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 537 S
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 538 S
CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 539 S CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 540 S OCHF.sub.2 OCH(CH.sub.3).sub.2
CH.sub.3 541 SO.sub.2 F OCH(CH.sub.3).sub.2 CH.sub.3 542 SO.sub.2
Cl OCH(CH.sub.3).sub.2 CH.sub.3 543 SO.sub.2 Br OCH(CH.sub.3).sub.2
CH.sub.3 544 SO.sub.2 NO.sub.2 OCH(CH.sub.3).sub.2 CH.sub.3 545
SO.sub.2 SCH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 546 SO.sub.2
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 547 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 548 SO.sub.2
CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 549 SO.sub.2 CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.3 550 SO.sub.2 OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.3 551 bond F OCH(CH.sub.3).sub.2
CH.sub.2CH.sub.3 552 bond Cl OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3
553 bond Br OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 554 bond NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 555 bond SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 556 bond SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 557 bond
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 558
bond CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 559 bond
CF.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 560 bond OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 561 CH.sub.2 F
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 562 CH.sub.2 Cl
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 563 CH.sub.2 Br
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 564 CH.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 565 CH.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 566 CH.sub.2 SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 567 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 568
CH.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 569 CH.sub.2
CF.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 570 CH.sub.2
OCHF.sub.2 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 571 O F
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 572 O Cl OCH(CH.sub.3).sub.2
CH.sub.2CH.sub.3 573 O Br OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 574
O NO.sub.2 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 575 O SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 576 O SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 577 O SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 578 O CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 579 O CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 580 O OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 581 S F OCH(CH.sub.3).sub.2
CH.sub.2CH.sub.3 582 S Cl OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 583
S Br OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 584 S NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 585 S SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 586 S SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 587 S SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 588 S CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 589 S CF.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 590 S OCHF.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 591 SO.sub.2 F
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 592 SO.sub.2 Cl
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 593 SO.sub.2 Br
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 594 SO.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 595 SO.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 596 SO.sub.2 SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 597 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 598
SO.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 599 SO.sub.2
CF.sub.3 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 600 SO.sub.2
OCHF.sub.2 OCH(CH.sub.3).sub.2 CH.sub.2CH.sub.3 601 bond F
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 602 bond Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 603 bond Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 604 bond NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 605 bond SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 606 bond SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 607 bond SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 608 bond CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 609 bond CF.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 610 bond OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 611 CH.sub.2 F
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 612 CH.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 613 CH.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 614 CH.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 615 CH.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 616 CH.sub.2 SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 617 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 618
CH.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 619 CH.sub.2
CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 620 CH.sub.2 OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 621 O F OCH.sub.2C.sub.6H.sub.5
CH.sub.3 622 O Cl OCH.sub.2C.sub.6H.sub.5 CH.sub.3 623 O Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 624 O NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 625 O SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 626 O SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 627 O SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 628 O CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 629 O CF.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 630 O OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 631 S F OCH.sub.2C.sub.6H.sub.5
CH.sub.3 632 S Cl OCH.sub.2C.sub.6H.sub.5 CH.sub.3 633 S Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 634 S NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 635 S SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 636 S SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 637 S SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 638 S CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 639 S CF.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 640 S OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 641 SO.sub.2 F
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 642 SO.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 643 SO.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 644 SO.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 645 SO.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 646 SO.sub.2 SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 647 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 648
SO.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 649 SO.sub.2
CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.3 650 SO.sub.2 OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.3 651 bond F OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 652 bond Cl OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 653 bond Br OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 654 bond NO.sub.2 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 655 bond SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 656 bond SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 657 bond SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 658 bond CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 659 bond CF.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 660 bond OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 661 CH.sub.2 F
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 662 CH.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 663 CH.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 664 CH.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 665 CH.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 666 CH.sub.2
SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 667
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 668 CH.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 669 CH.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 670 CH.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 671 O F OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3
672 O Cl OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 673 O Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 674 O NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 675 O SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 676 O SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 677 O
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3
678 O CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 679 O
CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 680 O OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 681 S F
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 682 S Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 683 S Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 684 S NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 685 S SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 686 S SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 687 S
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3
688 S CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 689 S
CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 690 S OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 691 SO.sub.2 F
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 692 SO.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 693 SO.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 694 SO.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 695 SO.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 696 SO.sub.2
SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH.sub.2CH.sub.3 697
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 698 SO.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 699 SO.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 700 SO.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
CH.sub.2CH.sub.3 701 bond F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 702 bond Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3
703 bond Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 704 bond
NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 705 bond
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 706 bond
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 707
bond SO.sub.2CH.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 708 bond CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 709 bond CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 710 bond OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 711 CH.sub.2 F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 712 CH.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 713 CH.sub.2 Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 714 CH.sub.2 NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 715 CH.sub.2
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 716
CH.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 717 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 718 CH.sub.2
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 719
CH.sub.2 CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3
720 CH.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 721 O F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 722
O Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 723 O Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 724 O NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 725 O SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 726 O
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 727
O SO.sub.2CH.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3
728 O CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 729 O
CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 730 O
OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 731 S F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 732 S Cl
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 733 S Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 734 S NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 735 S SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 736 S
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 737
S SO.sub.2CH.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 738 S CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 739 S CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 740 S OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 741 SO.sub.2 F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 742 SO.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 743 SO.sub.2 Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 744 SO.sub.2 NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 745 SO.sub.2
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 746
SO.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 747 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 748 SO.sub.2
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3 749
SO.sub.2 CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.3
750 SO.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.3 751 bond F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 752 bond Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 753 bond Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 754 bond NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 755 bond
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
756 bond SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 757 bond SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 758 bond
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 759
bond CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 760 bond OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 761 CH.sub.2
F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 762
CH.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
763 CH.sub.2 Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 764 CH.sub.2 NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 765 CH.sub.2
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
766 CH.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 767 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 768 CH.sub.2
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 769
CH.sub.2 CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 770 CH.sub.2 OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 771 O F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 772 O Cl
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 773 O Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 774 O
NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 775
O SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
776 O SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 777 O SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 778 O
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 779
O CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
780 O OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 781 S F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 782 S Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 783 S Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 784 S NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 785 S
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
786 S SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 787 S SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 788 S
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 789
S CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
790 S OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 791 SO.sub.2 F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 792 SO.sub.2
Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 793
SO.sub.2 Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3
794 SO.sub.2 NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 795 SO.sub.2 SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 796 SO.sub.2
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 797 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 798 SO.sub.2
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 799
SO.sub.2 CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH.sub.2CH.sub.3 800 SO.sub.2 OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH.sub.2CH.sub.3 801 bond F
SCH.sub.3 CH.sub.3 802 bond Cl SCH.sub.3 CH.sub.3 803 bond Br
SCH.sub.3 CH.sub.3 804 bond NO.sub.2 SCH.sub.3 CH.sub.3 805 bond
SCH.sub.3 SCH.sub.3 CH.sub.3 806 bond SO.sub.2CH.sub.3 SCH.sub.3
CH.sub.3 807 bond SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 808
bond CH.sub.3 SCH.sub.3 CH.sub.3 809 bond CF.sub.3 SCH.sub.3
CH.sub.3 810 bond OCHF.sub.2 SCH.sub.3 CH.sub.3 811 CH.sub.2 F
SCH.sub.3 CH.sub.3 812 CH.sub.2 Cl SCH.sub.3 CH.sub.3 813 CH.sub.2
Br SCH.sub.3 CH.sub.3 814 CH.sub.2 NO.sub.2 SCH.sub.3 CH.sub.3 815
CH.sub.2 SCH.sub.3 SCH.sub.3 CH.sub.3 816 CH.sub.2 SO.sub.2CH.sub.3
SCH.sub.3 CH.sub.3 817 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH.sub.3 818 CH.sub.2 CH.sub.3 SCH.sub.3 CH.sub.3 819 CH.sub.2
CF.sub.3 SCH.sub.3 CH.sub.3 820 CH.sub.2 OCHF.sub.2 SCH.sub.3
CH.sub.3 821 O F SCH.sub.3 CH.sub.3 822 O Cl SCH.sub.3 CH.sub.3 823
O Br SCH.sub.3 CH.sub.3 824 O NO.sub.2 SCH.sub.3 CH.sub.3 825 O
SCH.sub.3 SCH.sub.3 CH.sub.3 826 O SO.sub.2CH.sub.3 SCH.sub.3
CH.sub.3 827 O SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 828 O
CH.sub.3 SCH.sub.3 CH.sub.3 829 O CF.sub.3 SCH.sub.3 CH.sub.3 830 O
OCHF.sub.2 SCH.sub.3 CH.sub.3 831 S F SCH.sub.3 CH.sub.3 832 S Cl
SCH.sub.3 CH.sub.3 833 S Br SCH.sub.3 CH.sub.3 834 S NO.sub.2
SCH.sub.3 CH.sub.3 835 S SCH.sub.3 SCH.sub.3 CH.sub.3 836 S
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 837 S SO.sub.2CH.sub.2CH.sub.3
SCH.sub.3 CH.sub.3 838 S CH.sub.3 SCH.sub.3 CH.sub.3 839 S CF.sub.3
SCH.sub.3 CH.sub.3 840 S OCHF.sub.2 SCH.sub.3 CH.sub.3 841 SO.sub.2
F SCH.sub.3 CH.sub.3 842 SO.sub.2 Cl SCH.sub.3 CH.sub.3 843
SO.sub.2 Br SCH.sub.3 CH.sub.3 844 SO.sub.2 NO.sub.2 SCH.sub.3
CH.sub.3 845 SO.sub.2 SCH.sub.3 SCH.sub.3 CH.sub.3 846 SO.sub.2
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 847 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 848 SO.sub.2 CH.sub.3
SCH.sub.3 CH.sub.3 849 SO.sub.2 CF.sub.3 SCH.sub.3 CH.sub.3 850
SO.sub.2 OCHF.sub.2 SCH.sub.3 CH.sub.3 851 bond F SCH.sub.3
CH.sub.2CH.sub.3 852 bond Cl SCH.sub.3 CH.sub.2CH.sub.3 853 bond Br
SCH.sub.3 CH.sub.2CH.sub.3 854 bond NO.sub.2 SCH.sub.3
CH.sub.2CH.sub.3 855 bond SCH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 856
bond SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 857 bond
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 858 bond
CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 859 bond CF.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 860 bond OCHF.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 861
CH.sub.2 F SCH.sub.3 CH.sub.2CH.sub.3 862 CH.sub.2 Cl SCH.sub.3
CH.sub.2CH.sub.3 863 CH.sub.2 Br SCH.sub.3 CH.sub.2CH.sub.3 864
CH.sub.2 NO.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 865 CH.sub.2 SCH.sub.3
SCH.sub.3 CH.sub.2CH.sub.3 866 CH.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 867 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 868 CH.sub.2 CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3
869 CH.sub.2 CF.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 870 CH.sub.2
OCHF.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 871 O F SCH.sub.3
CH.sub.2CH.sub.3 872 O Cl SCH.sub.3 CH.sub.2CH.sub.3 873 O Br
SCH.sub.3 CH.sub.2CH.sub.3 874 O NO.sub.2 SCH.sub.3
CH.sub.2CH.sub.3 875 O SCH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 876 O
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 877 O
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 878 O CH.sub.3
SCH.sub.3 CH.sub.2CH.sub.3 879 O CF.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 880 O OCHF.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 881 S
F SCH.sub.3 CH.sub.2CH.sub.3 882 S Cl SCH.sub.3 CH.sub.2CH.sub.3
883 S Br SCH.sub.3 CH.sub.2CH.sub.3 884 S NO.sub.2 SCH.sub.3
CH.sub.2CH.sub.3 885 S SCH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 886 S
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 887 S
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 888 S CH.sub.3
SCH.sub.3 CH.sub.2CH.sub.3 889 S CF.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 890 S OCHF.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 891
SO.sub.2 F SCH.sub.3 CH.sub.2CH.sub.3 892 SO.sub.2 Cl SCH.sub.3
CH.sub.2CH.sub.3 893 SO.sub.2 Br SCH.sub.3 CH.sub.2CH.sub.3 894
SO.sub.2 NO.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 895 SO.sub.2 SCH.sub.3
SCH.sub.3 CH.sub.2CH.sub.3 896 SO.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 897 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH.sub.2CH.sub.3 898 SO.sub.2 CH.sub.3 SCH.sub.3 CH.sub.2CH.sub.3
899 SO.sub.2 CF.sub.3 SCH.sub.3 CH.sub.2CH.sub.3 900 SO.sub.2
OCHF.sub.2 SCH.sub.3 CH.sub.2CH.sub.3 901 bond F Cl CH.sub.3 902
bond Cl Cl CH.sub.3 903 bond Br Cl CH.sub.3 904 bond NO.sub.2 Cl
CH.sub.3 905 bond SCH.sub.3 Cl CH.sub.3 906 bond SO.sub.2CH.sub.3
Cl CH.sub.3 907 bond SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.3 908 bond
CH.sub.3 Cl CH.sub.3 909 bond CF.sub.3 Cl CH.sub.3 910 bond
OCHF.sub.2 Cl CH.sub.3 911 CH.sub.2 F Cl CH.sub.3 912 CH.sub.2 Cl
Cl CH.sub.3 913 CH.sub.2 Br Cl CH.sub.3 914 CH.sub.2 NO.sub.2 Cl
CH.sub.3 915 CH.sub.2 SCH.sub.3 Cl CH.sub.3 916 CH.sub.2
SO.sub.2CH.sub.3 Cl CH.sub.3 917 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
Cl CH.sub.3 918 CH.sub.2 CH.sub.3 Cl CH.sub.3 919 CH.sub.2 CF.sub.3
Cl CH.sub.3 920 CH.sub.2 OCHF.sub.2 Cl CH.sub.3 921 O F Cl CH.sub.3
922 O Cl Cl CH.sub.3 923 O Br Cl CH.sub.3 924 O NO.sub.2 Cl
CH.sub.3 925 O SCH.sub.3 Cl CH.sub.3 926 O SO.sub.2CH.sub.3 Cl
CH.sub.3 927 O SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.3 928 O CH.sub.3
Cl CH.sub.3 929 O CF.sub.3 Cl CH.sub.3 930 O OCHF.sub.2 Cl CH.sub.3
931 S F Cl CH.sub.3 932 S Cl Cl CH.sub.3 933 S Br Cl CH.sub.3 934 S
NO.sub.2 Cl CH.sub.3 935 S SCH.sub.3 Cl CH.sub.3 936 S
SO.sub.2CH.sub.3 Cl CH.sub.3 937 S SO.sub.2CH.sub.2CH.sub.3 Cl
CH.sub.3 938 S CH.sub.3 Cl CH.sub.3 939 S CF.sub.3 Cl CH.sub.3 940
S OCHF.sub.2 Cl CH.sub.3 941 SO.sub.2 F Cl CH.sub.3 942 SO.sub.2 Cl
Cl CH.sub.3 943 SO.sub.2 Br Cl CH.sub.3 944 SO.sub.2 NO.sub.2 Cl
CH.sub.3 945 SO.sub.2 SCH.sub.3 Cl CH.sub.3 946 SO.sub.2
SO.sub.2CH.sub.3 Cl CH.sub.3 947 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
Cl CH.sub.3 948 SO.sub.2 CH.sub.3 Cl CH.sub.3 949 SO.sub.2 CF.sub.3
Cl CH.sub.3 950 SO.sub.2 OCHF.sub.2 Cl CH.sub.3 951 bond F Cl
CH.sub.2CH.sub.3 952 bond Cl Cl CH.sub.2CH.sub.3 953 bond Br Cl
CH.sub.2CH.sub.3
954 bond NO.sub.2 Cl CH.sub.2CH.sub.3 955 bond SCH.sub.3 Cl
CH.sub.2CH.sub.3 956 bond SO.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 957
bond SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 958 bond CH.sub.3
Cl CH.sub.2CH.sub.3 959 bond CF.sub.3 Cl CH.sub.2CH.sub.3 960 bond
OCHF.sub.2 Cl CH.sub.2CH.sub.3 961 CH.sub.2 F Cl CH.sub.2CH.sub.3
962 CH.sub.2 Cl Cl CH.sub.2CH.sub.3 963 CH.sub.2 Br Cl
CH.sub.2CH.sub.3 964 CH.sub.2 NO.sub.2 Cl CH.sub.2CH.sub.3 965
CH.sub.2 SCH.sub.3 Cl CH.sub.2CH.sub.3 966 CH.sub.2
SO.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 967 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 968 CH.sub.2 CH.sub.3
Cl CH.sub.2CH.sub.3 969 CH.sub.2 CF.sub.3 Cl CH.sub.2CH.sub.3 970
CH.sub.2 OCHF.sub.2 Cl CH.sub.2CH.sub.3 971 O F Cl CH.sub.2CH.sub.3
972 O Cl Cl CH.sub.2CH.sub.3 973 O Br Cl CH.sub.2CH.sub.3 974 O
NO.sub.2 Cl CH.sub.2CH.sub.3 975 O SCH.sub.3 Cl CH.sub.2CH.sub.3
976 O SO.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 977 O
SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 978 O CH.sub.3 Cl
CH.sub.2CH.sub.3 979 O CF.sub.3 Cl CH.sub.2CH.sub.3 980 O
OCHF.sub.2 Cl CH.sub.2CH.sub.3 981 S F Cl CH.sub.2CH.sub.3 982 S Cl
Cl CH.sub.2CH.sub.3 983 S Br Cl CH.sub.2CH.sub.3 984 S NO.sub.2 Cl
CH.sub.2CH.sub.3 985 S SCH.sub.3 Cl CH.sub.2CH.sub.3 986 S
SO.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 987 S SO.sub.2CH.sub.2CH.sub.3
Cl CH.sub.2CH.sub.3 988 S CH.sub.3 Cl CH.sub.2CH.sub.3 989 S
CF.sub.3 Cl CH.sub.2CH.sub.3 990 S OCHF.sub.2 Cl CH.sub.2CH.sub.3
991 SO.sub.2 F Cl CH.sub.2CH.sub.3 992 SO.sub.2 Cl Cl
CH.sub.2CH.sub.3 993 SO.sub.2 Br Cl CH.sub.2CH.sub.3 994 SO.sub.2
NO.sub.2 Cl CH.sub.2CH.sub.3 995 SO.sub.2 SCH.sub.3 Cl
CH.sub.2CH.sub.3 996 SO.sub.2 SO.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3
997 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 Cl CH.sub.2CH.sub.3 998
SO.sub.2 CH.sub.3 Cl CH.sub.2CH.sub.3 999 SO.sub.2 CF.sub.3 Cl
CH.sub.2CH.sub.3 1000 SO.sub.2 OCHF.sub.2 Cl CH.sub.2CH.sub.3 1001
bond F OH CH(CH.sub.3).sub.2 1002 bond Cl OH CH(CH.sub.3).sub.2
1003 bond Br OH CH(CH.sub.3).sub.2 1004 bond NO.sub.2 OH
CH(CH.sub.3).sub.2 1005 bond SCH.sub.3 OH CH(CH.sub.3).sub.2 1006
bond SO.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1007 bond
SO.sub.2CH.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1008 bond CH.sub.3
OH CH(CH.sub.3).sub.2 1009 bond CF.sub.3 OH CH(CH.sub.3).sub.2 1010
bond OCHF.sub.2 OH CH(CH.sub.3).sub.2 1011 CH.sub.2 F OH
CH(CH.sub.3).sub.2 1012 CH.sub.2 Cl OH CH(CH.sub.3).sub.2 1013
CH.sub.2 Br OH CH(CH.sub.3).sub.2 1014 CH.sub.2 NO.sub.2 OH
CH(CH.sub.3).sub.2 1015 CH.sub.2 SCH.sub.3 OH CH(CH.sub.3).sub.2
1016 CH.sub.2 SO.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1017 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1018 CH.sub.2
CH.sub.3 OH CH(CH.sub.3).sub.2 1019 CH.sub.2 CF.sub.3 OH
CH(CH.sub.3).sub.2 1020 CH.sub.2 OCHF.sub.2 OH CH(CH.sub.3).sub.2
1021 O F OH CH(CH.sub.3).sub.2 1022 O Cl OH CH(CH.sub.3).sub.2 1023
O Br OH CH(CH.sub.3).sub.2 1024 O NO.sub.2 OH CH(CH.sub.3).sub.2
1025 O SCH.sub.3 OH CH(CH.sub.3).sub.2 1026 O SO.sub.2CH.sub.3 OH
CH(CH.sub.3).sub.2 1027 O SO.sub.2CH.sub.2CH.sub.3 OH
CH(CH.sub.3).sub.2 1028 O CH.sub.3 OH CH(CH.sub.3).sub.2 1029 O
CF.sub.3 OH CH(CH.sub.3).sub.2 1030 O OCHF.sub.2 OH
CH(CH.sub.3).sub.2 1031 S F OH CH(CH.sub.3).sub.2 1032 S Cl OH
CH(CH.sub.3).sub.2 1033 S Br OH CH(CH.sub.3).sub.2 1034 S NO.sub.2
OH CH(CH.sub.3).sub.2 1035 S SCH.sub.3 OH CH(CH.sub.3).sub.2 1036 S
SO.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1037 S
SO.sub.2CH.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1038 S CH.sub.3 OH
CH(CH.sub.3).sub.2 1039 S CF.sub.3 OH CH(CH.sub.3).sub.2 1040 S
OCHF.sub.2 OH CH(CH.sub.3).sub.2 1041 SO.sub.2 F OH
CH(CH.sub.3).sub.2 1042 SO.sub.2 Cl OH CH(CH.sub.3).sub.2 1043
SO.sub.2 Br OH CH(CH.sub.3).sub.2 1044 SO.sub.2 NO.sub.2 OH
CH(CH.sub.3).sub.2 1045 SO.sub.2 SCH.sub.3 OH CH(CH.sub.3).sub.2
1046 SO.sub.2 SO.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1047 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH CH(CH.sub.3).sub.2 1048 SO.sub.2
CH.sub.3 OH CH(CH.sub.3).sub.2 1049 SO.sub.2 CF.sub.3 OH
CH(CH.sub.3).sub.2 1050 SO.sub.2 OCHF.sub.2 OH CH(CH.sub.3).sub.2
1051 bond F OH C(CH.sub.3).sub.3 1052 bond Cl OH C(CH.sub.3).sub.3
1053 bond Br OH C(CH.sub.3).sub.3 1054 bond NO.sub.2 OH
C(CH.sub.3).sub.3 1055 bond SCH.sub.3 OH C(CH.sub.3).sub.3 1056
bond SO.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1057 bond
SO.sub.2CH.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1058 bond CH.sub.3 OH
C(CH.sub.3).sub.3 1059 bond CF.sub.3 OH C(CH.sub.3).sub.3 1060 bond
OCHF.sub.2 OH C(CH.sub.3).sub.3 1061 CH.sub.2 F OH
C(CH.sub.3).sub.3 1062 CH.sub.2 Cl OH C(CH.sub.3).sub.3 1063
CH.sub.2 Br OH C(CH.sub.3).sub.3 1064 CH.sub.2 NO.sub.2 OH
C(CH.sub.3).sub.3 1065 CH.sub.2 SCH.sub.3 OH C(CH.sub.3).sub.3 1066
CH.sub.2 SO.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1067 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1068 CH.sub.2
CH.sub.3 OH C(CH.sub.3).sub.3 1069 CH.sub.2 CF.sub.3 OH
C(CH.sub.3).sub.3 1070 CH.sub.2 OCHF.sub.2 OH C(CH.sub.3).sub.3
1071 O F OH C(CH.sub.3).sub.3 1072 O Cl OH C(CH.sub.3).sub.3 1073 O
Br OH C(CH.sub.3).sub.3 1074 O NO.sub.2 OH C(CH.sub.3).sub.3 1075 O
SCH.sub.3 OH C(CH.sub.3).sub.3 1076 O SO.sub.2CH.sub.3 OH
C(CH.sub.3).sub.3 1077 O SO.sub.2CH.sub.2CH.sub.3 OH
C(CH.sub.3).sub.3 1078 O CH.sub.3 OH C(CH.sub.3).sub.3 1079 O
CF.sub.3 OH C(CH.sub.3).sub.3 1080 O OCHF.sub.2 OH
C(CH.sub.3).sub.3 1081 S F OH C(CH.sub.3).sub.3 1082 S Cl OH
C(CH.sub.3).sub.3 1083 S Br OH C(CH.sub.3).sub.3 1084 S NO.sub.2 OH
C(CH.sub.3).sub.3 1085 S SCH.sub.3 OH C(CH.sub.3).sub.3 1086 S
SO.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1087 S
SO.sub.2CH.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1088 S CH.sub.3 OH
C(CH.sub.3).sub.3 1089 S CF.sub.3 OH C(CH.sub.3).sub.3 1090 S
OCHF.sub.2 OH C(CH.sub.3).sub.3 1091 SO.sub.2 F OH
C(CH.sub.3).sub.3 1092 SO.sub.2 Cl OH C(CH.sub.3).sub.3 1093
SO.sub.2 Br OH C(CH.sub.3).sub.3 1094 SO.sub.2 NO.sub.2 OH
C(CH.sub.3).sub.3 1095 SO.sub.2 SCH.sub.3 OH C(CH.sub.3).sub.3 1096
SO.sub.2 SO.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1097 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OH C(CH.sub.3).sub.3 1098 SO.sub.2
CH.sub.3 OH C(CH.sub.3).sub.3 1099 SO.sub.2 CF.sub.3 OH
C(CH.sub.3).sub.3 1100 SO.sub.2 OCHF.sub.2 OH C(CH.sub.3).sub.3
1101 bond F OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1102 bond Cl
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1103 bond Br OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1104 bond NO.sub.2 OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1105 bond SCH.sub.3 OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1106 bond SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1107 bond SO.sub.2CH.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1108 bond CH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1109 bond CF.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1110 bond OCHF.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1111 CH.sub.2 F
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1112 CH.sub.2 Cl
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1113 CH.sub.2 Br
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1114 CH.sub.2 NO.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1115 CH.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1116 CH.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1117 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1118
CH.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1119
CH.sub.2 CF.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1120
CH.sub.2 OCHF.sub.2 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1121 O F
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1122 O Cl OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1123 O Br OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2
1124 O NO.sub.2 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1125 O
SCH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1126 O
SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1127 O
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1128
O CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1129 O CF.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1130 O OCHF.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1131 S F OCOC.sub.6H.sub.5
CH(CH.sub.3).sub.2 1132 S Cl OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2
1133 S Br OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1134 S NO.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1135 S SCH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1136 S SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1137 S
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1138
S CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1139 S CF.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1140 S OCHF.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1141 SO.sub.2 F
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1142 SO.sub.2 Cl
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1143 SO.sub.2 Br
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1144 SO.sub.2 NO.sub.2
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1145 SO.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1146 SO.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1147 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1148
SO.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1149
SO.sub.2 CF.sub.3 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1150
SO.sub.2 OCHF.sub.2 OCOC.sub.6H.sub.5 CH(CH.sub.3).sub.2 1151 bond
F OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1152 bond Cl
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1153 bond Br OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1154 bond NO.sub.2 OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1155 bond SCH.sub.3 OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1156 bond SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1157 bond SO.sub.2CH.sub.2CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1158 bond CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1159 bond CF.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1160 bond OCHF.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1161 CH.sub.2 F
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1162 CH.sub.2 Cl
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1163 CH.sub.2 Br
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1164 CH.sub.2 NO.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1165 CH.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1166 CH.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1167 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1168
CH.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1169 CH.sub.2
CF.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1170 CH.sub.2
OCHF.sub.2 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1171 O F
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1172 O Cl OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1173 O Br OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3
1174 O NO.sub.2 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1175 O
SCH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1176 O
SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1177 O
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1178 O
CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1179 O CF.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1180 O OCHF.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1181 S F OCOC.sub.6H.sub.5
C(CH.sub.3).sub.3 1182 S Cl OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3
1183 S Br OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1184 S NO.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1185 S SCH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1186 S SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1187 S SO.sub.2CH.sub.2CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1188 S CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1189 S CF.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1190 S OCHF.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1191 SO.sub.2 F
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1192 SO.sub.2 Cl
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1193 SO.sub.2 Br
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1194 SO.sub.2 NO.sub.2
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1195 SO.sub.2 SCH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1196 SO.sub.2 SO.sub.2CH.sub.3
OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1197 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1198
SO.sub.2 CH.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1199 SO.sub.2
CF.sub.3 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3 1200 SO.sub.2
OCHF.sub.2 OCOC.sub.6H.sub.5 C(CH.sub.3).sub.3
1201 bond F OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1202 bond Cl
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1203 bond Br
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1204 bond NO.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1205 bond SCH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1206 bond SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1207 bond
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2
1208 bond CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1209
bond CF.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1210 bond
OCHF.sub.2 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1211 CH.sub.2 F
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1212 CH.sub.2 Cl
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1213 CH.sub.2 Br
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1214 CH.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1215 CH.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1216 CH.sub.2
SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1217
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1218 CH.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1219 CH.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1220 CH.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1221 O F OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2
1222 O Cl OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1223 O Br
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1224 O NO.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1225 O SCH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1226 O SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1227 O
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2
1228 O CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1229 O
CF.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1230 O OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1231 S F
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1232 S Cl
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1233 S Br
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1234 S NO.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1235 S SCH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1236 S SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1237 S
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2
1238 S CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1239 S
CF.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1240 S OCHF.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1241 SO.sub.2 F
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1242 SO.sub.2 Cl
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1243 SO.sub.2 Br
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1244 SO.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1245 SO.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1246 SO.sub.2
SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 CH(CH.sub.3).sub.2 1247
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1248 SO.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1249 SO.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1250 SO.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3
CH(CH.sub.3).sub.2 1251 bond F OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1252 bond Cl OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1253 bond Br OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1254 bond NO.sub.2 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1255 bond SCH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1256 bond SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1257 bond SO.sub.2CH.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1258 bond CH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1259 bond CF.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1260 bond OCHF.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1261 CH.sub.2 F
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1262 CH.sub.2 Cl
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1263 CH.sub.2 Br
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1264 CH.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1265 CH.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1266 CH.sub.2
SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1267
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1268 CH.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1269 CH.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1270 CH.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1271 O F OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3
1272 O Cl OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1273 O Br
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1274 O NO.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1275 O SCH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1276 O SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1277 O
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3
1278 O CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1279 O
CF.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1280 O OCHF.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1281 S F
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1282 S Cl
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1283 S Br
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1284 S NO.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1285 S SCH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1286 S SO.sub.2CH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1287 S
SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3
1288 S CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1289 S
CF.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1290 S OCHF.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1291 SO.sub.2 F
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1292 SO.sub.2 Cl
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1293 SO.sub.2 Br
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1294 SO.sub.2 NO.sub.2
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1295 SO.sub.2 SCH.sub.3
OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1296 SO.sub.2
SO.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3 C(CH.sub.3).sub.3 1297
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1298 SO.sub.2 CH.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1299 SO.sub.2 CF.sub.3 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1300 SO.sub.2 OCHF.sub.2 OCOC(CH.sub.3).sub.3
C(CH.sub.3).sub.3 1301 bond F OCOSCH.sub.3 CH(CH.sub.3).sub.2 1302
bond Cl OCOSCH.sub.3 CH(CH.sub.3).sub.2 1303 bond Br OCOSCH.sub.3
CH(CH.sub.3).sub.2 1304 bond NO.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1305 bond SCH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1306 bond SO.sub.2CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1307 bond SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1308 bond CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1309 bond CF.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1310 bond OCHF.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1311 CH.sub.2 F OCOSCH.sub.3 CH(CH.sub.3).sub.2
1312 CH.sub.2 Cl OCOSCH.sub.3 CH(CH.sub.3).sub.2 1313 CH.sub.2 Br
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1314 CH.sub.2 NO.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1315 CH.sub.2 SCH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1316 CH.sub.2 SO.sub.2CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1317 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1318 CH.sub.2 CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1319 CH.sub.2 CF.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1320 CH.sub.2 OCHF.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1321 O F OCOSCH.sub.3 CH(CH.sub.3).sub.2 1322 O
Cl OCOSCH.sub.3 CH(CH.sub.3).sub.2 1323 O Br OCOSCH.sub.3
CH(CH.sub.3).sub.2 1324 O NO.sub.2 OCOSCH.sub.3 CH(CH.sub.3).sub.2
1325 O SCH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1326 O
SO.sub.2CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1327 O
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1328 O
CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1329 O CF.sub.3
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1330 O OCHF.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1331 S F OCOSCH.sub.3 CH(CH.sub.3).sub.2 1332 S
Cl OCOSCH.sub.3 CH(CH.sub.3).sub.2 1333 S Br OCOSCH.sub.3
CH(CH.sub.3).sub.2 1334 S NO.sub.2 OCOSCH.sub.3 CH(CH.sub.3).sub.2
1335 S SCH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1336 S
SO.sub.2CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1337 S
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1338 S
CH.sub.3 OCOSCH.sub.3 CH(CH.sub.3).sub.2 1339 S CF.sub.3
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1340 S OCHF.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1341 SO.sub.2 F OCOSCH.sub.3 CH(CH.sub.3).sub.2
1342 SO.sub.2 Cl OCOSCH.sub.3 CH(CH.sub.3).sub.2 1343 SO.sub.2 Br
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1344 SO.sub.2 NO.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1345 SO.sub.2 SCH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1346 SO.sub.2 SO.sub.2CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1347 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 CH(CH.sub.3).sub.2 1348 SO.sub.2 CH.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1349 SO.sub.2 CF.sub.3 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1350 SO.sub.2 OCHF.sub.2 OCOSCH.sub.3
CH(CH.sub.3).sub.2 1351 bond F OCOSCH.sub.3 C(CH.sub.3).sub.3 1352
bond Cl OCOSCH.sub.3 C(CH.sub.3).sub.3 1353 bond Br OCOSCH.sub.3
C(CH.sub.3).sub.3 1354 bond NO.sub.2 OCOSCH.sub.3 C(CH.sub.3).sub.3
1355 bond SCH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1356 bond
SO.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1357 bond
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1358 bond
CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1359 bond CF.sub.3
OCOSCH.sub.3 C(CH.sub.3).sub.3 1360 bond OCHF.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1361 CH.sub.2 F OCOSCH.sub.3 C(CH.sub.3).sub.3
1362 CH.sub.2 Cl OCOSCH.sub.3 C(CH.sub.3).sub.3 1363 CH.sub.2 Br
OCOSCH.sub.3 C(CH.sub.3).sub.3 1364 CH.sub.2 NO.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1365 CH.sub.2 SCH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1366 CH.sub.2 SO.sub.2CH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1367 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 C(CH.sub.3).sub.3 1368 CH.sub.2 CH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1369 CH.sub.2 CF.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1370 CH.sub.2 OCHF.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1371 O F OCOSCH.sub.3 C(CH.sub.3).sub.3 1372 O Cl
OCOSCH.sub.3 C(CH.sub.3).sub.3 1373 O Br OCOSCH.sub.3
C(CH.sub.3).sub.3 1374 O NO.sub.2 OCOSCH.sub.3 C(CH.sub.3).sub.3
1375 O SCH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1376 O
SO.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1377 O
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1378 O
CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1379 O CF.sub.3
OCOSCH.sub.3 C(CH.sub.3).sub.3 1380 O OCHF.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1381 S F OCOSCH.sub.3 C(CH.sub.3).sub.3 1382 S Cl
OCOSCH.sub.3 C(CH.sub.3).sub.3 1383 S Br OCOSCH.sub.3
C(CH.sub.3).sub.3 1384 S NO.sub.2 OCOSCH.sub.3 C(CH.sub.3).sub.3
1385 S SCH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1386 S
SO.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1387 S
SO.sub.2CH.sub.2CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1388 S
CH.sub.3 OCOSCH.sub.3 C(CH.sub.3).sub.3 1389 S CF.sub.3
OCOSCH.sub.3 C(CH.sub.3).sub.3 1390 S OCHF.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1391 SO.sub.2 F OCOSCH.sub.3 C(CH.sub.3).sub.3
1392 SO.sub.2 Cl OCOSCH.sub.3 C(CH.sub.3).sub.3 1393 SO.sub.2 Br
OCOSCH.sub.3 C(CH.sub.3).sub.3 1394 SO.sub.2 NO.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1395 SO.sub.2 SCH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1396 SO.sub.2 SO.sub.2CH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1397 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OCOSCH.sub.3 C(CH.sub.3).sub.3 1398 SO.sub.2 CH.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1399 SO.sub.2 CF.sub.3 OCOSCH.sub.3
C(CH.sub.3).sub.3 1400 SO.sub.2 OCHF.sub.2 OCOSCH.sub.3
C(CH.sub.3).sub.3 1401 bond F OCH.sub.3 CH(CH.sub.3).sub.2 1402
bond Cl OCH.sub.3 CH(CH.sub.3).sub.2 1403 bond Br OCH.sub.3
CH(CH.sub.3).sub.2 1404 bond NO.sub.2 OCH.sub.3 CH(CH.sub.3).sub.2
1405 bond SCH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1406 bond
SO.sub.2CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1407 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1408 bond
CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1409 bond CF.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1410 bond OCHF.sub.2 OCH.sub.3
CH(CH.sub.3).sub.2 1411 CH.sub.2 F OCH.sub.3 CH(CH.sub.3).sub.2
1412 CH.sub.2 Cl OCH.sub.3 CH(CH.sub.3).sub.2 1413 CH.sub.2 Br
OCH.sub.3 CH(CH.sub.3).sub.2 1414 CH.sub.2 NO.sub.2 OCH.sub.3
CH(CH.sub.3).sub.2 1415 CH.sub.2 SCH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1416 CH.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1417 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1418 CH.sub.2 CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1419 CH.sub.2 CF.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1420 CH.sub.2 OCHF.sub.2 OCH.sub.3
CH(CH.sub.3).sub.2 1421 O F OCH.sub.3 CH(CH.sub.3).sub.2 1422 O Cl
OCH.sub.3 CH(CH.sub.3).sub.2 1423 O Br OCH.sub.3 CH(CH.sub.3).sub.2
1424 O NO.sub.2 OCH.sub.3 CH(CH.sub.3).sub.2 1425 O SCH.sub.3
OCH.sub.3 CH(CH.sub.3).sub.2 1426 O SO.sub.2CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1427 O SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1428 O CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2
1429 O CF.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1430 O OCHF.sub.2
OCH.sub.3 CH(CH.sub.3).sub.2 1431 S F OCH.sub.3 CH(CH.sub.3).sub.2
1432 S Cl OCH.sub.3 CH(CH.sub.3).sub.2 1433 S Br OCH.sub.3
CH(CH.sub.3).sub.2 1434 S NO.sub.2 OCH.sub.3 CH(CH.sub.3).sub.2
1435 S SCH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1436 S
SO.sub.2CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1437 S
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1438 S
CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1439 S CF.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1440 S OCHF.sub.2 OCH.sub.3 CH(CH.sub.3).sub.2
1441 SO.sub.2 F OCH.sub.3 CH(CH.sub.3).sub.2 1442 SO.sub.2 Cl
OCH.sub.3 CH(CH.sub.3).sub.2 1443 SO.sub.2 Br OCH.sub.3
CH(CH.sub.3).sub.2 1444 SO.sub.2 NO.sub.2 OCH.sub.3
CH(CH.sub.3).sub.2 1445 SO.sub.2 SCH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2 1446 SO.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
CH(CH.sub.3).sub.2
1447 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2
1448 SO.sub.2 CH.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1449 SO.sub.2
CF.sub.3 OCH.sub.3 CH(CH.sub.3).sub.2 1450 SO.sub.2 OCHF.sub.2
OCH.sub.3 CH(CH.sub.3).sub.2 1451 bond F OCH.sub.3
C(CH.sub.3).sub.3 1452 bond Cl OCH.sub.3 C(CH.sub.3).sub.3 1453
bond Br OCH.sub.3 C(CH.sub.3).sub.3 1454 bond NO.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1455 bond SCH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3
1456 bond SO.sub.2CH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1457 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1458 bond
CH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1459 bond CF.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1460 bond OCHF.sub.2 OCH.sub.3 C(CH.sub.3).sub.3
1461 CH.sub.2 F OCH.sub.3 C(CH.sub.3).sub.3 1462 CH.sub.2 Cl
OCH.sub.3 C(CH.sub.3).sub.3 1463 CH.sub.2 Br OCH.sub.3
C(CH.sub.3).sub.3 1464 CH.sub.2 NO.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1465 CH.sub.2 SCH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1466 CH.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1467 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1468 CH.sub.2 CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1469 CH.sub.2 CF.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1470 CH.sub.2 OCHF.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1471 O F OCH.sub.3 C(CH.sub.3).sub.3 1472 O Cl
OCH.sub.3 C(CH.sub.3).sub.3 1473 O Br OCH.sub.3 C(CH.sub.3).sub.3
1474 O NO.sub.2 OCH.sub.3 C(CH.sub.3).sub.3 1475 O SCH.sub.3
OCH.sub.3 C(CH.sub.3).sub.3 1476 O SO.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1477 O SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1478 O CH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1479
O CF.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1480 O OCHF.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1481 S F OCH.sub.3 C(CH.sub.3).sub.3 1482 S Cl
OCH.sub.3 C(CH.sub.3).sub.3 1483 S Br OCH.sub.3 C(CH.sub.3).sub.3
1484 S NO.sub.2 OCH.sub.3 C(CH.sub.3).sub.3 1485 S SCH.sub.3
OCH.sub.3 C(CH.sub.3).sub.3 1486 S SO.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1487 S SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1488 S CH.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1489
S CF.sub.3 OCH.sub.3 C(CH.sub.3).sub.3 1490 S OCHF.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1491 SO.sub.2 F OCH.sub.3 C(CH.sub.3).sub.3 1492
SO.sub.2 Cl OCH.sub.3 C(CH.sub.3).sub.3 1493 SO.sub.2 Br OCH.sub.3
C(CH.sub.3).sub.3 1494 SO.sub.2 NO.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1495 SO.sub.2 SCH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1496 SO.sub.2 SO.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1497 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1498 SO.sub.2 CH.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1499 SO.sub.2 CF.sub.3 OCH.sub.3
C(CH.sub.3).sub.3 1500 SO.sub.2 OCHF.sub.2 OCH.sub.3
C(CH.sub.3).sub.3 1501 bond F OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1502 bond Cl OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1503 bond Br OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1504 bond NO.sub.2 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1505 bond SCH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1506 bond SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1507 bond SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1508 bond CH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1509 bond CF.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1510 bond OCHF.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1511 CH.sub.2 F
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1512 CH.sub.2 Cl
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1513 CH.sub.2 Br
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1514 CH.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1515 CH.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1516 CH.sub.2
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1517
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1518 CH.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1519 CH.sub.2 CF.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1520 CH.sub.2 OCHF.sub.2 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1521 O F OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2
1522 O Cl OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1523 O Br
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1524 O NO.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1525 O SCH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1526 O SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1527 O
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2
1528 O CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1529 O
CF.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1530 O OCHF.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1531 S F OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1532 S Cl OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2
1533 S Br OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1534 S NO.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1535 S SCH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1536 S SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1537 S
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2
1538 S CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1539 S
CF.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1540 S OCHF.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1541 SO.sub.2 F
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1542 SO.sub.2 Cl
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1543 SO.sub.2 Br
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1544 SO.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1545 SO.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1546 SO.sub.2
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 CH(CH.sub.3).sub.2 1547
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1548 SO.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1549 SO.sub.2 CF.sub.3 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1550 SO.sub.2 OCHF.sub.2 OCH(CH.sub.3).sub.2
CH(CH.sub.3).sub.2 1551 bond F OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1552 bond Cl OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1553 bond Br OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1554 bond NO.sub.2 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1555 bond SCH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1556 bond SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1557 bond SO.sub.2CH.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1558 bond CH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1559 bond CF.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1560 bond OCHF.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1561 CH.sub.2 F
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1562 CH.sub.2 Cl
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1563 CH.sub.2 Br
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1564 CH.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1565 CH.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1566 CH.sub.2
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1567
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1568 CH.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1569 CH.sub.2 CF.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1570 CH.sub.2 OCHF.sub.2 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1571 O F OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3
1572 O Cl OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1573 O Br
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1574 O NO.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1575 O SCH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1576 O SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1577 O
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1578
O CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1579 O CF.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1580 O OCHF.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1581 S F OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1582 S Cl OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3
1583 S Br OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1584 S NO.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1585 S SCH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1586 S SO.sub.2CH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1587 S
SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1588
S CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1589 S CF.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1590 S OCHF.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1591 SO.sub.2 F
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1592 SO.sub.2 Cl
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1593 SO.sub.2 Br
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1594 SO.sub.2 NO.sub.2
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1595 SO.sub.2 SCH.sub.3
OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1596 SO.sub.2
SO.sub.2CH.sub.3 OCH(CH.sub.3).sub.2 C(CH.sub.3).sub.3 1597
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1598 SO.sub.2 CH.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1599 SO.sub.2 CF.sub.3 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1600 SO.sub.2 OCHF.sub.2 OCH(CH.sub.3).sub.2
C(CH.sub.3).sub.3 1601 bond F OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1602 bond Cl OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1603 bond Br OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1604 bond NO.sub.2 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1605 bond SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1606 bond SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1607 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2
1608 bond CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1609
bond CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1610 bond
OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1611 CH.sub.2
F OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1612 CH.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1613 CH.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1614 CH.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1615 CH.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1616 CH.sub.2
SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1617
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1618 CH.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1619 CH.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1620 CH.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1621 O F OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1622 O Cl OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1623 O Br OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1624 O NO.sub.2 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1625 O SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1626 O SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1627 O SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1628 O CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1629 O CF.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1630 O OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1631 S F
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1632 S Cl
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1633 S Br
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1634 S NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1635 S SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1636 S SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1637 S
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2
1638 S CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1639 S
CF.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1640 S
OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1641 SO.sub.2
F OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1642 SO.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1643 SO.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1644 SO.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1645 SO.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1646 SO.sub.2
SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 CH(CH.sub.3).sub.2 1647
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1648 SO.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1649 SO.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1650 SO.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
CH(CH.sub.3).sub.2 1651 bond F OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1652 bond Cl OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1653 bond Br OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1654 bond NO.sub.2 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1655 bond SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1656 bond SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1657 bond
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1658 bond CH.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1659
bond CF.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1660 bond
OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1661 CH.sub.2
F OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1662 CH.sub.2 Cl
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1663 CH.sub.2 Br
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1664 CH.sub.2 NO.sub.2
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1665 CH.sub.2 SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1666 CH.sub.2
SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1667
CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1668 CH.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1669 CH.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1670 CH.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1671 O F OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1672 O Cl OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1673 O Br OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1674 O NO.sub.2 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1675 O SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1676 O SO.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1677 O SO.sub.2CH.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1678 O CH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1679 O CF.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1680 O OCHF.sub.2
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1681 S F
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1682 S Cl
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1683 S Br
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1684 S NO.sub.2
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1685 S SCH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1686 S SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1687 S SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1688 S CH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1689 S CF.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1690 S OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1691 SO.sub.2 F OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1692 SO.sub.2 Cl OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1693 SO.sub.2 Br OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1694 SO.sub.2 NO.sub.2 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1695 SO.sub.2 SCH.sub.3 OCH.sub.2C.sub.6H.sub.5
C(CH.sub.3).sub.3 1696 SO.sub.2 SO.sub.2CH.sub.3
OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3 1697 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1698 SO.sub.2 CH.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1699 SO.sub.2 CF.sub.3 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1700 SO.sub.2 OCHF.sub.2 OCH.sub.2C.sub.6H.sub.5 C(CH.sub.3).sub.3
1701 bond F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1702 bond Cl
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1703 bond
Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1704
bond NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1705 bond SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1706 bond
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1707 bond SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1708 bond
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1709 bond CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1710 bond OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1711
CH.sub.2 F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1712 CH.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1713 CH.sub.2 Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1714
CH.sub.2 NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1715 CH.sub.2 SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1716
CH.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1717 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1718
CH.sub.2 CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1719 CH.sub.2 CF.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1720
CH.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1721 O F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1722 O Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1723 O Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1724 O NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1725 O
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1726 O SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1727 O SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1728 O
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1729 O CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1730 O OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1731 S F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1732 S Cl
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1733 S Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1734 S
NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1735 S SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1736 S SO.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1737 S
SO.sub.2CH.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1738 S CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1739 S
CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2
1740 S OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1741 SO.sub.2 F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1742
SO.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1743 SO.sub.2 Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1744
SO.sub.2 NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1745 SO.sub.2 SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1746
SO.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1747 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1748
SO.sub.2 CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1749 SO.sub.2 CF.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) CH(CH.sub.3).sub.2 1750
SO.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
CH(CH.sub.3).sub.2 1751 bond F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1752 bond
Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1753
bond Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1754 bond NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1755 bond SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1756 bond
SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1757 bond SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1758 bond
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1759 bond CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1760 bond OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1761
CH.sub.2 F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1762 CH.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1763 CH.sub.2 Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1764
CH.sub.2 NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1765 CH.sub.2 SCH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1766
CH.sub.2 SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1767 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1768
CH.sub.2 CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1769 CH.sub.2 CF.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1770
CH.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1771 O F OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1772 O Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1773 O Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1774 O NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1775 O
SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1776 O SO.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1777 O SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1778 O
CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1779 O CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1780 O OCHF.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1781 S F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1782 S Cl
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1783 S Br
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1784 S
NO.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1785 S SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1786 S SO.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1787 S
SO.sub.2CH.sub.2CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1788 S CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1789 S
CF.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1790 S OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1791 SO.sub.2 F
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1792
SO.sub.2 Cl OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3
1793 SO.sub.2 Br OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1794 SO.sub.2 NO.sub.2
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1795
SO.sub.2 SCH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1796 SO.sub.2 SO.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1797
SO.sub.2 SO.sub.2CH.sub.2CH.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1798
SO.sub.2 CH.sub.3 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1799 SO.sub.2 CF.sub.3
OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4) C(CH.sub.3).sub.3 1800
SO.sub.2 OCHF.sub.2 OSO.sub.2(4-CH.sub.3--C.sub.6H.sub.4)
C(CH.sub.3).sub.3 1801 bond F SCH.sub.3 CH(CH.sub.3).sub.2 1802
bond Cl SCH.sub.3 CH(CH.sub.3).sub.2 1803 bond Br SCH.sub.3
CH(CH.sub.3).sub.2 1804 bond NO.sub.2 SCH.sub.3 CH(CH.sub.3).sub.2
1805 bond SCH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1806 bond
SO.sub.2CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1807 bond
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1808 bond
CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1809 bond CF.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1810 bond OCHF.sub.2 SCH.sub.3
CH(CH.sub.3).sub.2 1811 CH.sub.2 F SCH.sub.3 CH(CH.sub.3).sub.2
1812 CH.sub.2 Cl SCH.sub.3 CH(CH.sub.3).sub.2 1813 CH.sub.2 Br
SCH.sub.3 CH(CH.sub.3).sub.2 1814 CH.sub.2 NO.sub.2 SCH.sub.3
CH(CH.sub.3).sub.2 1815 CH.sub.2 SCH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1816 CH.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1817 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1818 CH.sub.2 CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1819 CH.sub.2 CF.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1820 CH.sub.2 OCHF.sub.2 SCH.sub.3
CH(CH.sub.3).sub.2 1821 O F SCH.sub.3 CH(CH.sub.3).sub.2 1822 O Cl
SCH.sub.3 CH(CH.sub.3).sub.2 1823 O Br SCH.sub.3 CH(CH.sub.3).sub.2
1824 O NO.sub.2 SCH.sub.3 CH(CH.sub.3).sub.2 1825 O SCH.sub.3
SCH.sub.3 CH(CH.sub.3).sub.2 1826 O SO.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1827 O SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1828 O CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2
1829 O CF.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1830 O OCHF.sub.2
SCH.sub.3 CH(CH.sub.3).sub.2 1831 S F SCH.sub.3 CH(CH.sub.3).sub.2
1832 S Cl SCH.sub.3 CH(CH.sub.3).sub.2 1833 S Br SCH.sub.3
CH(CH.sub.3).sub.2 1834 S NO.sub.2 SCH.sub.3 CH(CH.sub.3).sub.2
1835 S SCH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1836 S
SO.sub.2CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1837 S
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1838 S
CH.sub.3 SCH.sub.3 CH(CH.sub.3).sub.2 1839 S CF.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1840 S OCHF.sub.2 SCH.sub.3 CH(CH.sub.3).sub.2
1841 SO.sub.2 F SCH.sub.3 CH(CH.sub.3).sub.2 1842 SO.sub.2 Cl
SCH.sub.3 CH(CH.sub.3).sub.2 1843 SO.sub.2 Br SCH.sub.3
CH(CH.sub.3).sub.2 1844 SO.sub.2 NO.sub.2 SCH.sub.3
CH(CH.sub.3).sub.2 1845 SO.sub.2 SCH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1846 SO.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1847 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1848 SO.sub.2 CH.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1849 SO.sub.2 CF.sub.3 SCH.sub.3
CH(CH.sub.3).sub.2 1850 SO.sub.2 OCHF.sub.2 SCH.sub.3
CH(CH.sub.3).sub.2 1851 bond F SCH.sub.3 C(CH.sub.3).sub.3 1852
bond Cl SCH.sub.3 C(CH.sub.3).sub.3 1853 bond Br SCH.sub.3
C(CH.sub.3).sub.3 1854 bond NO.sub.2 SCH.sub.3 C(CH.sub.3).sub.3
1855 bond SCH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1856 bond
SO.sub.2CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1857 bond
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1858 bond
CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1859 bond CF.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1860 bond OCHF.sub.2 SCH.sub.3 C(CH.sub.3).sub.3
1861 CH.sub.2 F SCH.sub.3 C(CH.sub.3).sub.3 1862 CH.sub.2 Cl
SCH.sub.3 C(CH.sub.3).sub.3 1863 CH.sub.2 Br SCH.sub.3
C(CH.sub.3).sub.3 1864 CH.sub.2 NO.sub.2 SCH.sub.3
C(CH.sub.3).sub.3 1865 CH.sub.2 SCH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1866 CH.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1867 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1868 CH.sub.2 CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1869 CH.sub.2 CF.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1870 CH.sub.2 OCHF.sub.2 SCH.sub.3
C(CH.sub.3).sub.3 1871 O F SCH.sub.3 C(CH.sub.3).sub.3 1872 O Cl
SCH.sub.3 C(CH.sub.3).sub.3 1873 O Br SCH.sub.3 C(CH.sub.3).sub.3
1874 O NO.sub.2 SCH.sub.3 C(CH.sub.3).sub.3 1875 O SCH.sub.3
SCH.sub.3 C(CH.sub.3).sub.3 1876 O SO.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1877 O SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1878 O CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1879
O CF.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1880 O OCHF.sub.2 SCH.sub.3
C(CH.sub.3).sub.3 1881 S F SCH.sub.3 C(CH.sub.3).sub.3 1882 S Cl
SCH.sub.3 C(CH.sub.3).sub.3 1883 S Br SCH.sub.3 C(CH.sub.3).sub.3
1884 S NO.sub.2 SCH.sub.3 C(CH.sub.3).sub.3
1885 S SCH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1886 S
SO.sub.2CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1887 S
SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1888 S
CH.sub.3 SCH.sub.3 C(CH.sub.3).sub.3 1889 S CF.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1890 S OCHF.sub.2 SCH.sub.3 C(CH.sub.3).sub.3
1891 SO.sub.2 F SCH.sub.3 C(CH.sub.3).sub.3 1892 SO.sub.2 Cl
SCH.sub.3 C(CH.sub.3).sub.3 1893 SO.sub.2 Br SCH.sub.3
C(CH.sub.3).sub.3 1894 SO.sub.2 NO.sub.2 SCH.sub.3
C(CH.sub.3).sub.3 1895 SO.sub.2 SCH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1896 SO.sub.2 SO.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1897 SO.sub.2 SO.sub.2CH.sub.2CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1898 SO.sub.2 CH.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1899 SO.sub.2 CF.sub.3 SCH.sub.3
C(CH.sub.3).sub.3 1900 SO.sub.2 OCHF.sub.2 SCH.sub.3
C(CH.sub.3).sub.3 1901 bond F Cl CH(CH.sub.3).sub.2 1902 bond Cl Cl
CH(CH.sub.3).sub.2 1903 bond Br Cl CH(CH.sub.3).sub.2 1904 bond
NO.sub.2 Cl CH(CH.sub.3).sub.2 1905 bond SCH.sub.3 Cl
CH(CH.sub.3).sub.2 1906 bond SO.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2
1907 bond SO.sub.2CH.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2 1908 bond
CH.sub.3 Cl CH(CH.sub.3).sub.2 1909 bond CF.sub.3 Cl
CH(CH.sub.3).sub.2 1910 bond OCHF.sub.2 Cl CH(CH.sub.3).sub.2 1911
CH.sub.2 F Cl CH(CH.sub.3).sub.2 1912 CH.sub.2 Cl Cl
CH(CH.sub.3).sub.2 1913 CH.sub.2 Br Cl CH(CH.sub.3).sub.2 1914
CH.sub.2 NO.sub.2 Cl CH(CH.sub.3).sub.2 1915 CH.sub.2 SCH.sub.3 Cl
CH(CH.sub.3).sub.2 1916 CH.sub.2 SO.sub.2CH.sub.3 Cl
CH(CH.sub.3).sub.2 1917 CH.sub.2 SO.sub.2CH.sub.2CH.sub.3 Cl
CH(CH.sub.3).sub.2 1918 CH.sub.2 CH.sub.3 Cl CH(CH.sub.3).sub.2
1919 CH.sub.2 CF.sub.3 Cl CH(CH.sub.3).sub.2 1920 CH.sub.2
OCHF.sub.2 Cl CH(CH.sub.3).sub.2 1921 O F Cl CH(CH.sub.3).sub.2
1922 O Cl Cl CH(CH.sub.3).sub.2 1923 O Br Cl CH(CH.sub.3).sub.2
1924 O NO.sub.2 Cl CH(CH.sub.3).sub.2 1925 O SCH.sub.3 Cl
CH(CH.sub.3).sub.2 1926 O SO.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2
1927 O SO.sub.2CH.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2 1928 O
CH.sub.3 Cl CH(CH.sub.3).sub.2 1929 O CF.sub.3 Cl
CH(CH.sub.3).sub.2 1930 O OCHF.sub.2 Cl CH(CH.sub.3).sub.2 1931 S F
Cl CH(CH.sub.3).sub.2 1932 S Cl Cl CH(CH.sub.3).sub.2 1933 S Br Cl
CH(CH.sub.3).sub.2 1934 S NO.sub.2 Cl CH(CH.sub.3).sub.2 1935 S
SCH.sub.3 Cl CH(CH.sub.3).sub.2 1936 S SO.sub.2CH.sub.3 Cl
CH(CH.sub.3).sub.2 1937 S SO.sub.2CH.sub.2CH.sub.3 Cl
CH(CH.sub.3).sub.2 1938 S CH.sub.3 Cl CH(CH.sub.3).sub.2 1939 S
CF.sub.3 Cl CH(CH.sub.3).sub.2 1940 S OCHF.sub.2 Cl
CH(CH.sub.3).sub.2 1941 SO.sub.2 F Cl CH(CH.sub.3).sub.2 1942
SO.sub.2 Cl Cl CH(CH.sub.3).sub.2 1943 SO.sub.2 Br Cl
CH(CH.sub.3).sub.2 1944 SO.sub.2 NO.sub.2 Cl CH(CH.sub.3).sub.2
1945 SO.sub.2 SCH.sub.3 Cl CH(CH.sub.3).sub.2 1946 SO.sub.2
SO.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2 1947 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 Cl CH(CH.sub.3).sub.2 1948 SO.sub.2
CH.sub.3 Cl CH(CH.sub.3).sub.2 1949 SO.sub.2 CF.sub.3 Cl
CH(CH.sub.3).sub.2 1950 SO.sub.2 OCHF.sub.2 Cl CH(CH.sub.3).sub.2
1951 bond F Cl C(CH.sub.3).sub.3 1952 bond Cl Cl C(CH.sub.3).sub.3
1953 bond Br Cl C(CH.sub.3).sub.3 1954 bond NO.sub.2 Cl
C(CH.sub.3).sub.3 1955 bond SCH.sub.3 Cl C(CH.sub.3).sub.3 1956
bond SO.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1957 bond
SO.sub.2CH.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1958 bond CH.sub.3 Cl
C(CH.sub.3).sub.3 1959 bond CF.sub.3 Cl C(CH.sub.3).sub.3 1960 bond
OCHF.sub.2 Cl C(CH.sub.3).sub.3 1961 CH.sub.2 F Cl
C(CH.sub.3).sub.3 1962 CH.sub.2 Cl Cl C(CH.sub.3).sub.3 1963
CH.sub.2 Br Cl C(CH.sub.3).sub.3 1964 CH.sub.2 NO.sub.2 Cl
C(CH.sub.3).sub.3 1965 CH.sub.2 SCH.sub.3 Cl C(CH.sub.3).sub.3 1966
CH.sub.2 SO.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1967 CH.sub.2
SO.sub.2CH.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1968 CH.sub.2
CH.sub.3 Cl C(CH.sub.3).sub.3 1969 CH.sub.2 CF.sub.3 Cl
C(CH.sub.3).sub.3 1970 CH.sub.2 OCHF.sub.2 Cl C(CH.sub.3).sub.3
1971 O F Cl C(CH.sub.3).sub.3 1972 O Cl Cl C(CH.sub.3).sub.3 1973 O
Br Cl C(CH.sub.3).sub.3 1974 O NO.sub.2 Cl C(CH.sub.3).sub.3 1975 O
SCH.sub.3 Cl C(CH.sub.3).sub.3 1976 O SO.sub.2CH.sub.3 Cl
C(CH.sub.3).sub.3 1977 O SO.sub.2CH.sub.2CH.sub.3 Cl
C(CH.sub.3).sub.3 1978 O CH.sub.3 Cl C(CH.sub.3).sub.3 1979 O
CF.sub.3 Cl C(CH.sub.3).sub.3 1980 O OCHF.sub.2 Cl
C(CH.sub.3).sub.3 1981 S F Cl C(CH.sub.3).sub.3 1982 S Cl Cl
C(CH.sub.3).sub.3 1983 S Br Cl C(CH.sub.3).sub.3 1984 S NO.sub.2 Cl
C(CH.sub.3).sub.3 1985 S SCH.sub.3 Cl C(CH.sub.3).sub.3 1986 S
SO.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1987 S
SO.sub.2CH.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1988 S CH.sub.3 Cl
C(CH.sub.3).sub.3 1989 S CF.sub.3 Cl C(CH.sub.3).sub.3 1990 S
OCHF.sub.2 Cl C(CH.sub.3).sub.3 1991 SO.sub.2 F Cl
C(CH.sub.3).sub.3 1992 SO.sub.2 Cl Cl C(CH.sub.3).sub.3 1993
SO.sub.2 Br Cl C(CH.sub.3).sub.3 1994 SO.sub.2 NO.sub.2 Cl
C(CH.sub.3).sub.3 1995 SO.sub.2 SCH.sub.3 Cl C(CH.sub.3).sub.3 1996
SO.sub.2 SO.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1997 SO.sub.2
SO.sub.2CH.sub.2CH.sub.3 Cl C(CH.sub.3).sub.3 1998 SO.sub.2
CH.sub.3 Cl C(CH.sub.3).sub.3 1999 SO.sub.2 CF.sub.3 Cl
C(CH.sub.3).sub.3 2000 SO.sub.2 OCHF.sub.2 Cl C(CH.sub.3).sub.3
[0186] Very particular preference is also given to the compounds of
the formula Ia2 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=1), in particular to the compounds
Ia2.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are as
defined in Table 1. ##STR15##
[0187] Very particular preference is also given to the compounds of
the formula Ia3 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3.dbd.CH.sub.3, l=1), in particular to the
compounds Ia3.n, where the variables X, R.sup.4, R.sup.10 and
R.sup.11 are as defined in Table 1. ##STR16##
[0188] Very particular preference is also given to the compounds of
the formula Ia4 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=2), in particular to the compounds
Ia4.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are as
defined in Table 1. ##STR17##
[0189] Very particular preference is also given to the compounds of
the formula Ia5 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=1), in particular to the compounds
Ia5.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are as
defined in Table 1. ##STR18##
[0190] Very particular preference is also given to the compounds of
the formula Ia6 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=2), in particular to the compounds
Ia6.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are as
defined in Table 1. ##STR19##
[0191] Very particular preference is also given to the compounds of
the formula Ia7 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia7.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR20##
[0192] Very particular preference is also given to the compounds of
the formula Ia8 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sup.3, l=1), in particular to the compounds
Ia8.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are as
defined in Table 1. ##STR21##
[0193] Very particular preference is also given to the compounds of
the formula Ia9 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia9.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR22##
[0194] Very particular preference is also given to the compounds of
the formula Ia10 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia10.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR23##
[0195] Very particular preference is also given to the compounds of
the formula Ia11 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia11.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR24##
[0196] Very particular preference is also given to the compounds of
the formula Ia12 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia12.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR25##
[0197] Very particular preference is also given to the compounds of
the formula Ia13 (=Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia13.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR26##
[0198] Very particular preference is also given to the compounds of
the formula Ia14 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=1), in particular to the compounds
Ia14.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are
as defined in Table 1. ##STR27##
[0199] Very particular preference is also given to the compounds of
the formula Ia15 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=1), in particular to the compounds
Ia15.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are
as defined in Table 1. ##STR28##
[0200] Very particular preference is also given to the compounds of
the formula Ia16 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia16.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR29##
[0201] Very particular preference is also given to the compounds of
the formula Ia17 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia17.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR30##
[0202] Very particular preference is also given to the compounds of
the formula Ia18 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.13=CH.sub.3, l=1), in particular to the compounds
Ia18.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are
as defined in Table 1. ##STR31##
[0203] Very particular preference is also given to the compounds of
the formula Ia19 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia19.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR32##
[0204] Very particular preference is also given to the compounds of
the formula Ia20 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia20.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR33##
[0205] Very particular preference is also given to the compounds of
the formula Ia21 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, l=0), in particular to the compounds Ia21.n, where the
variables X, R.sup.4, R.sup.10 and R.sup.11 are as defined in Table
1. ##STR34##
[0206] Very particular preference is also given to the compounds of
the formula Ia22 (.ident.Ia where R.sup.1, R.sup.2, R.sup.5 and
R.sup.12=H, R.sup.3=CH.sub.3, l=1), in particular to the compounds
Ia22.n, where the variables X, R.sup.4, R.sup.10 and R.sup.11 are
as defined in Table 1. ##STR35##
[0207] The tricyclic benzoylpyrazole derivatives of the formula I
can be obtained by various routes, for example by one of the
following processes: [0208] A. Preparation of compounds of the
formula I where R.sup.10=halogen by reacting a tricyclic
benzoylpyrazole derivative of the formula I.alpha. (.ident.I where
R.sup.10=hydroxyl) with a halogenating agent: ##STR36## [0209]
Suitable halogenating agents are, for example, phosgene,
diphosgene, triphosgene, thionyl chloride, oxalyl chloride,
phosphorus oxychloride, phosphorus pentachloride, mesyl chloride,
chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide,
phosphorus oxybromide, etc. [0210] The starting materials are
generally employed in equimolar amounts. However, it may also be
advantageous to employ an excess of one or the other component.
[0211] Suitable solvents are, for example, chlorinated
hydrocarbons, such as methylene chloride or 1,2-dichloroethane,
aromatic hydrocarbons, for example toluene, xylene or
chlorobenzene, polar aprotic solvents, such as acetonitrile,
dimethylformamide or dimethyl sulfoxide, or mixtures of these.
However, it is also possible to carry out the reaction in the
absence of solvent. [0212] The reaction temperature is generally in
the range from 0.degree. C. to the boiling point of the reaction
mixture. [0213] Work-up can be carried out in a manner known per se
to afford the product. [0214] B. Preparation of compounds of the
formula I where R.sup.10=OR.sup.13, by reacting a tricyclic
benzoylpyrazole derivative of the formula I.alpha. (.ident.I where
R.sup.10=hydroxyl) with an alkylating agent III. ##STR37## [0215]
L.sup.1 is a nucleophilically replaceable leaving group, such as
halogen, for example chlorine or bromine, hetaryl, for example
imidazolyl, carboxylate, for example acetate, or sulfonate, for
example mesylate or triflate, etc. [0216] The compounds of the
formula III can be employed directly, such as, for example, in the
case of the carbonyl halides, or be generated in situ, for example
activated carboxylic acids (using carboxylic acid and
dicyclohexylcarbodiimide etc.). [0217] The starting materials are
generally employed in equimolar amounts. However, it may also be
advantageous to employ an excess of one or the other component.
[0218] If appropriate, it may also be advantageous to carry out the
reaction in the presence of a base. Here, the reactants and the
base are advantageously employed in equimolar amounts. In certain
cases, an excess of base, for example from 1.5 to 3 molar
equivalents, may be advantageous. [0219] Suitable bases are
tertiary alkylamines, such as triethylamine, aromatic amines, such
as pyridine, alkali metal carbonates, for example sodium carbonate
or potassium carbonate, alkali metal bicarbonates, for example
sodium bicarbonate and potassium bicarbonate, alkali metal
alkoxides, such as sodium methoxide, sodium ethoxide, potassium
tert-butoxide, or alkali metal hydrides, for example sodium
hydride. Preference is given to using triethylamine or pyridine.
[0220] Suitable solvents are, for example, chlorinated
hydrocarbons, such as methylene chloride or 1,2-dichloroethane,
aromatic hydrocarbons, for example toluene, xylene or
chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl
ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as
acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters,
such as ethyl acetate, or mixtures of these. [0221] The reaction
temperature is generally in the range from 0.degree. C. to the
boiling point of the reaction mixture. [0222] Work-up can be
carried out in a manner known per se to afford the product. [0223]
C. Preparation of compounds of the formula I where
R.sup.10=OR.sup.13, SR.sup.13, NR.sup.15R.sup.16 or N-bonded
heterocyclyl by reacting compounds of the formula I.beta. (.ident.I
where R.sup.10=halogen) with a compound of the formula IV.alpha.,
IV.beta., IV.gamma. or IV.delta., if appropriate in the presence of
a base or with prior formation of salt. ##STR38## [0224] The
starting materials are generally employed in equimolar amounts.
However, it may also be advantageous to employ an excess of one or
the other component. [0225] If appropriate, it may also be
advantageous to carry out the reaction in the presence of a base.
Here, the reactants and the base are advantageously employed in
equimolar amounts. An excess of base, for example from 1.5 to 3
molar equivalents, based on I.beta. (where R.sup.10=halogen), may
be advantageous in certain cases. [0226] Suitable bases are
tertiary alkylamines, such as triethylamine, aromatic amines, such
as pyridine, alkali metal carbonates, for example sodium carbonate
or potassium carbonate, alkali metal bicarbonates, for example
sodium bicarbonate and potassium bicarbonate, alkali metal
alkoxides, such as sodium methoxide, sodium ethoxide, potassium
tert-butoxide, or alkali metal hydrides, for example sodium
hydride. Preference is given to using sodium hydride or potassium
tert-butoxide. [0227] Suitable solvents are, for example,
chlorinated hydrocarbons, such as methylene chloride or
1,2-dichloroethane, aromatic hydrocarbons, for example toluene,
xylene or chlorobenzene, ethers, such as diethyl ether, methyl
tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic
solvents, such as acetonitrile, dimethylformamide or dimethyl
sulfoxide, or mixtures of these. [0228] The reaction temperature is
generally in the range from 0.degree. C. to the boiling point of
the reaction mixture. [0229] Work-up can be carried out in a manner
known per se to afford the product. [0230] D. Preparation of
compounds of the formula I where R.sup.10=SO.sub.2R.sup.14 by
reacting compounds of the formula I where R.sup.10=SR.sup.10
(I.gamma.) with an oxidizing agent. ##STR39## [0231] Suitable
oxidizing agents are, for example, m-chloroperbenzoic acid,
peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide,
if appropriate in the presence of a catalyst, such as tungstate.
[0232] The starting materials are generally employed in equimolar
amounts. However, it may also be advantageous to employ an excess
of one or the other component. [0233] Suitable solvents are, for
example, chlorinated hydrocarbons, such as methylene chloride or
1,2-dichloroethane, aromatic hydrocarbons, for example, toluene,
xylene or chlorobenzene, ethers, such as diethyl ether,
methyltert-butyl ether, tetrahydrofuran or dioxane, polar aprotic
solvents, such as acetonitrile or dimethylformamide, or esters,
such as ethyl acetate, or mixtures of these. [0234] The reaction
temperature is generally in the range from 0.degree. C. to the
boiling point of the reaction mixture. [0235] Work-up can be
carried out in a manner known per se to afford the product. [0236]
E. Preparation of compounds of the formula I where R.sup.9=IIa
(where R.sup.10+ hydroxyl or mercapto) by reacting a metalated
pyrazole derivative of the formula V with a tricyclic benzoic acid
derivative of the formula VI.alpha.: ##STR40## [0237] Here, M is a
metal, in particular an alkali metal, such as lithium or sodium, an
alkaline earth metal, such as, for example, magnesium, or a
transition metal, such as palladium, nickel, etc. and L.sup.2 is a
nucleophilically replaceable leaving group, such as halogen, for
example chlorine or bromine, alkylsulfonate, such as mesylate,
haloalkylsulfonate, such as triflate, or cyanide. [0238] The
reaction is generally carried out at temperatures of from
-100.degree. C. to the reflux temperature of the reaction mixture.
Suitable solvents are inert aprotic solvents, such as ethers, for
example diethyl ether, tetrahydrofuran. The compounds of the
formula VI.alpha. are generally employed in excess, but it may also
be advantageous to employ them in equimolar amounts or in
substoichiometric amounts. Work-up is carried out to afford the
product. [0239] The metalated pyrazole derivatives of the formula V
can be formed in a manner known per se by reacting pyrazoles which
are halogenated in the 4-position with metals, such as lithium,
sodium, magnesium, etc., or with organometallic compounds, such as,
for example, butyllithium. However, it is also possible to metalate
pyrazoles which are linked in the 4 position to hydrogen directly,
for example with the abovementioned metals or organometallic
compounds. The reactions are generally carried out in an inert
aprotic solvent, preferably in ether, such as diethyl ether,
tetrahydrofuran, etc. The reaction temperature is in the range from
-100.degree. C. to the boiling point of the reaction mixture. The
compounds of the formula V are generally directly reacted further
or generated in situ. [0240] F. Preparation of compounds of the
formula I.alpha. (.ident.I where R.sup.10=hydroxyl) by reacting an
activated tricyclic benzoic acid of the formula VI.beta. or a
tricyclic benzoic acid VI.gamma., preferably activated in situ,
with a pyrazole of the formula VII to give the acylation product,
followed by rearrangement. ##STR41##
[0241] L.sup.3 is a nucleophilically replaceable leaving group,
such as halogen, for example bromine or chlorine, hetaryl, for
example imidazolyl or pyridyl, carboxylate, for example acetate or
trifluoroacetate, etc.
[0242] The activated tricyclic benzoic acid VI.beta. can be
employed directly, such as in the case of the tricyclic benzoyl
halides, or be generated in situ, for example using
dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester,
2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole,
etc.
[0243] If appropriate, it may be advantageous to carry out the
acylation reaction in the presence of a base. Here, the reactants
and the auxiliary base are advantageously employed in equimolar
amounts. A slight excess of auxiliary base, for example from 1.2 to
1.5 molar equivalents, based on VI, may be advantageous in certain
cases.
[0244] Suitable auxiliary bases are tertiary alkylamines, pyridine,
or alkali metal carbonates. Suitable solvents are, for example,
chlorinated hydrocarbons, such as methylene chloride or
1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene
or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl
ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as
acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters,
such as ethyl acetate, or mixtures of these.
[0245] If tricyclic benzoyl halides are employed as activated
carboxylic acid components, it may be advantageous to cool the
reaction mixture to 0-10.degree. C. when adding this reaction
partner. The mixture is subsequently stirred at 20-100.degree. C.,
preferably at 25-50.degree. C., until the reaction has gone to
completion. Work-up is carried out in a customary manner, for
example by pouring the reaction mixture into water and extracting
the product of value. Solvents which are suitable for this purpose
are, in particular, methylene chloride, diethyl ether and ethyl
acetate. The organic phase is dried and the solvent removed, and
the crude ester can then be employed for the rearrangement without
further purification.
[0246] The rearrangement of the esters VIII to give the compounds
of the formula I.alpha. is advantageously carried out at from 20 to
100.degree. C. in a solvent and in the presence of a base and, if
appropriate, using a cyano compound as catalyst.
[0247] Solvents which may be used are, for example, acetonitrile,
methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate,
toluene or mixtures of these. Preferred solvents are acetonitrile
and dioxane.
[0248] Suitable bases are tertiary amines, such as triethylamine,
aromatic amines, such as pyridine, or alkali metal carbonates, such
as sodium carbonate or potassium carbonate, which are preferably
employed in equimolar amounts or in an up to four-fold excess,
based on the ester. Preference is given to using triethylamine or
alkali metal carbonate, preferably in double the equimolar ratio,
based on the ester.
[0249] Suitable cyano compounds are inorganic cyanides, such as
sodium cyanide or potassium cyanide, and organic cyano compounds,
such as acetone cyanohydrin or trimethylsilyl cyanide. They are
employed in an amount of from 1 to 50 mol percent, based on the
ester. Preference is given to using acetone cyanohydrin or
trimethylsilyl cyanide, for example in an amount of from 5 to 15,
preferably 10, mol percent, based on the ester.
[0250] Work-up may be carried out in a manner known per se. The
reaction mixture is, for example, acidified using dilute mineral
acid, such as 5% strength hydrochloric acid or sulfuric acid, and
extracted with an organic solvent, for example methylene chloride
or ethyl acetate. The organic extract can be extracted with 5-10%
strength alkali metal carbonate solution, for example sodium
carbonate or potassium carbonate solution. The aqueous phase is
acidified and the resulting precipitate is filtered off with
suction and/or extracted with methylene chloride or ethyl acetate,
the extract being dried and concentrated.
[0251] However, it is also possible to generate the ester VIII in
situ by reacting a pyrazole of the formula VII, or an alkali metal
salt thereof, with a tricyclic benzene derivative of the formula IX
in the presence of carbon monoxide, a catalyst and a base.
##STR42##
[0252] L.sup.4 is a leaving group, such as halogen, for example
chlorine, bromine or iodine, or sulfonate such as mesylate or
triflate; preference is given to bromine or triflate.
[0253] If appropriate, the ester VIII reacts directly to give the
tricyclic benzoylpyrazole derivative of the formula I.alpha..
[0254] Suitable catalysts are palladium ligand complexes in which
the palladium is present in oxidation state 0, metallic palladium,
if appropriate applied to a support, and preferably palladium(II)
salts. The reaction with palladium(II) salts and metallic palladium
is preferably carried out in the presence of complex ligands.
[0255] A suitable palladium(0) ligand complex is, for example,
tetrakis(triphenylphosphane)palladium.
[0256] Metallic palladium is preferably applied to an inert
carrier, such as, for example, activated carbon, silica, alumina,
barium sulfate or calcium carbonate. The reaction is preferably
carried out in the presence of complex ligands, such as, for
example, triphenylphosphane.
[0257] Suitable palladium(II) salts are, for example, palladium
acetate and palladium chloride. Preference is given to carrying out
the reaction in the presence of complex ligands such as, for
example, triphenylphosphane.
[0258] Suitable complex ligands for the palladium ligand complexes,
or complex ligands in whose presence the reaction with metallic
palladium or palladium(II) salts is preferably carried out are
tertiary phosphanes whose structure is represented by the following
formulae: ##STR43## where n is a number from 1 to 4 and the
radicals R.sup.a to R.sup.g are C.sub.1-C.sub.6-alkyl,
aryl-C.sub.1-C.sub.2-alkyl or preferably aryl. Aryl is, for
example, naphthyl and unsubstituted or substituted phenyl such as,
for example, 2-tolyl and in particular unsubstituted phenyl.
[0259] The complex palladium salts can be prepared in a manner
known per se starting from commercially available palladium salts,
such as palladium chloride or palladium acetate, and the
corresponding phosphanes, such as, for example, triphenylphosphane
or 1,2-bis(diphenylphosphano)ethane. A large number of complexed
palladium salts is also commercially available. Preferred palladium
salts are
[(R)-(+)-2,2'-bis(diphenylphosphano)-1,1'-binaphthyl]palladium(II)
chloride, bis(triphenylphosphane)palladium(II) acetate and in
particular bis(triphenylphosphane)palladium(II) chloride.
[0260] The palladium catalyst is generally employed in a
concentration of from 0.05 to 5 mol %, and preferably of 1-3 mol
%.
[0261] Suitable bases are tertiary amines, such as, for example,
N-methylpiperidine, ethyldiisopropylamine,
1,8-bisdimethylaminonaphthalene and in particular triethylamine.
Also suitable are alkali metal carbonates, such as sodium carbonate
or potassium carbonate. However, mixtures of potassium carbonate
and triethylamine are also suitable.
[0262] In general, from 2 to 4 molar equivalents, in particular 2
molar equivalents, of the alkali metal carbonate, and from 1 to 4
molar equivalents, in particular 2 molar equivalents, of the
tertiary amine are employed, based on the tricyclic benzene
derivative of the formula IX.
[0263] Suitable solvents are nitrites, such as benzonitrile and
acetonitrile, amides, such as dimethylformamide, dimethylacetamide,
tetra-C.sub.1-C.sub.4-alkylureas or N-methylpyrrolidone, and
preferably ethers, such as tetrahydrofuran, methyl tert-butyl
ether. Particular preference is given to using, as solvents, ethers
such as 1,4-dioxane and dimethoxyethane.
[0264] The tricyclic benzoyl halides of the formula VI.beta. where
L.sup.3=Cl, Br can be prepared in a manner known per se by reacting
the tricyclic benzoic acids of the formula VI.gamma. (.ident.VIb)
with halogenating agents such as thionyl chloride, thionyl bromide,
phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl
bromide.
[0265] In a known manner, the tricyclic benzoic acids of the
formula VI.gamma. (.ident.VIb) can be prepared by acidic or basic
hydrolysis from the corresponding esters VIc.
[0266] Tricyclic benzoic acid derivatives of the formula VI
##STR44## where: [0267] X is oxygen, sulfur, S.dbd.O,
S(.dbd.O).sub.2, CR.sup.6R.sup.7, NR.sup.8 or a bond; [0268] Y
together with the two carbons to which it is attached forms a
saturated, partially saturated or unsaturated 5- or 6-membered
heterocycle which contains one to three identical or different
heteroatoms selected from the following group: oxygen, sulfur or
nitrogen; [0269] R.sup.1, R.sup.2, R.sup.6, R.sup.7 are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0270]
R.sup.3 is halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0271] R.sup.4 is nitro, halogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)-aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl) amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
[0272] R.sup.5 is hydrogen, C.sub.1-C.sub.6-alkyl or halogen;
[0273] R.sup.8 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, formyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
[0274] l is 0, 1 or 2; [0275] R.sup.17 is hydroxyl or a radical
which can be removed by hydrolysis; are novel.
[0276] Examples of radicals which can be removed by hydrolysis are
alkoxy, phenoxy, alkylthio and phenylthio radicals which can be
unsubstituted or substituted, halides, heteroaryl radicals which
are attached via nitrogen, amino and imino radicals which may be
unsubstituted or substituted, etc.
[0277] Preference is given to tricyclic benzoyl halides VIa (VI
where R.sup.17=halogen) ##STR45## where the variables X, Y, R.sup.1
to R.sup.5 and l are as defined under formula VI and [0278] Hal is
halogen, in particular chloride or bromide.
[0279] Preference is also given to tricyclic benzoic acids of the
formula VIb (VI where R.sup.17=hydroxyl; .ident.VI.gamma.),
##STR46## where the variables X, Y, R.sup.1 to R.sup.5 and l are as
defined under formula VI.
[0280] Preference is also given to tricyclic benzoic esters of the
formula VIc (VI where R.sup.17=T=C.sub.1-C.sub.6-alkoxy), ##STR47##
where the variables X, Y, R.sup.1 to R.sup.5 and l are as defined
under formula VI and [0281] T is C.sub.1-C.sub.6-alkoxy.
[0282] With respect to the variables X, Y, R.sup.1 to R.sup.5 and
l, the particularly preferred embodiments of the tricyclic benzoic
acid derivatives of the formulae VI, VIa, VIb and VIc correspond to
those of the tricyclic benzoylpyrazole derivatives of the formula
I.
[0283] Particular preference is given to the compounds VI, VIa, VIb
and VIc where Y together with the two carbons to which it is
attached forms the following heterocycles: ##STR48##
[0284] Here, extraordinary preference is given to the compounds VI,
VIa, VIb and VIc where [0285] R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; in particular
C.sub.1-C.sub.6-alkylsulfonyl.
[0286] The tricyclic benzoic esters VIc can be obtained in
different ways.
[0287] For example, benzoic esters of the formula X, which are
prepared in a manner known per se (cf., for example, Chem. Pharm.
Bull. 1985, 33 (8), 3336; Helv. Chim. Acta 1987, 70, 1326; J. Chem.
Soc. Perkin Trans. 1972, 2019; J. Chem. Soc. Perkin Trans. 1991,
2763; Tetrahydron Asymmetry 1998, 9, 1137), can be cyclized to
cyclic ketones of the formula XI (cf., for example, Chem. Ber.
1923, 56, 1819; J. Chem. Soc. Perkin 11991, 2763; J. Med. Chem.
1988, 31, 230; Tetrahedron 1987, 43, 4549; Synlett 1991, 6, 443;
Chem. Pharm. Bull. 1985, 33 (8), 3336). Analogously to known
processes (cf., for example, J. Heterocyclic Chem. 1976, 13, 545;
J. Heterocyclic Chem. 1972, 9, 1341; J. Org. Chem. 1978, 43, 3015;
J. Chem. Soc. Perkin Trans. I 1978, 86; J. Org. Chem. 1986, 51,
2021), these can be converted into the tricyclic benzoic esters of
the formula VIc. ##STR49##
[0288] Furthermore, it may be suitable to cyclize the cyclic ketone
of the formula XI in a manner known per se (XII), for example using
an anhydride or acid anhydride, if appropriate in the presence of
catalytic amounts of a Lewis acid, such as boron trifluoride (cf.,
for example, Can. J. Chem. 1979, 57, 3292; J. Am. Chem. Soc. 1953,
75, 626), followed by reaction with a hydrazine (cf. A. R.
Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 5, p.
121, 277-280 (1984), Pergamon Press; J. Org. Chem. 1961, 26, 451;
Org. Synth. 1949, 29, 54), where the resulting pyrazole radical can
be modified further by customary processes.
[0289] Furthermore, the diketone XII can be reacted with
hydroxylamine or equivalents thereof (cf. A. R. Katritzky et al.,
Comprehensive Heterocyclic Chemistry, Vol. 6, p. 61-64, 118 (1984),
Pergamon Press; Chem. Ber. 1967, 100, 3326). This gives the
corresponding isoxazole derivatives which can be modified further
by customary processes.
[0290] It is also possible to react the diketone XII with amidines
(cf., for example, A. R. Katritzky et al., Comprehensive
Heterocyclic Chemistry, Vol. 3, p. 112-114 (1924), Pergamon Press;
J. Chem. Soc. C 1967, 1922; Org. Synth. 1963, IV, 182). If
required, the resulting pyrimidine derivatives can be modified
further by customary processes. ##STR50##
[0291] In the reactA123ions mentioned above, it is also possible to
employ, instead of the diketone XII, equivalents thereof, such as
enol ethers or enamines, which can be prepared analogously to known
processes.
[0292] It may also be possible to react the cyclic ketone of the
formula XI analogously to known processes with an aldehyde or
ketone to give (XIII) (cf., for example, Tetrahedron Lett. 1978,
2111; Tetrahedron Lett. 1981, 5251; Chem. Ber. 1960, 2294; J. Chem.
Soc. Perkin Trans. 1, 1991, 1467; Tetrahedron Lett. 1992, 8091).
The resulting unsaturated cyclic ketone of the formula XIII can be
reacted with a hydrazine in a manner known per se (cf., for
example, A. R. Katritzky et al. Comprehensive Heterocyclic
Chemistry, Vol. 2, 6 (1984), Pergamon Press; J. Heterocyclic Chem.
1969, 533; J. Heterocyclic Chem. 1968, 853), where the resulting
pyrazoline can be modified further by customary processes.
[0293] It is furthermore possible to react the unsaturated cyclic
ketone of the formula XIII with hydroxylamine or equivalents
thereof (Z. Chem. 1980, 20, 19). This gives the corresponding
isoxazoline derivatives, which can be modified further by customary
processes. ##STR51##
[0294] Furthermore, it is possible to convert aldehydes of the
formula XIV, which can be prepared in a manner known per se,
analogously to processes known from the literature by reaction with
a hydrazine or hydroxylamine (or equivalents of these) into the
corresponding hydrazones or oximes (cf., for example, Synth.
Commun. 1990, 20, 1373; J. Org. Chem. 1980, 45, 3756). These in
turn can be converted in a manner known per se into the
corresponding 1,3-dipoles, which then react in a
[3+2]-cycloaddition to give the compounds VIc (cf., for example,
Synth. Commun. 1990, 20, 1373; EP-A 386 892; J. Org. Chem. 1980,
45, 3756; Tetrahedron Lett. 1981, 22, 1333.)
[0295] The resulting pyrazoles or pyrazolines and isoxazoles or
isoxazolines can be modified further by customary processes.
##STR52##
[0296] It is also possible to react the cyclic ketone of the
formula XI with a dithiol or a "mixed alcohol" analogously to
processes known from the literature (cf., for example, T. W. Greene
et al., Protective Groups in Organic Synthesis, John Wiley &
Sons, 133-140), and to subject it subsequently to a rearrangement
in the presence of bromine or a suitable Lewis acid, such as, for
example, tellurium tetrachloride (cf. Tetrahedron 1991, 47, 4187;
Synthesis 1991, 223; J. Chem. Soc. Chem. Commun. 1985, 1645).
##STR53##
[0297] The resulting heterocycles can, if desired, be modified
further by processes known per se.
[0298] The abovementioned substitutents R.sup.3a are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, hydroxyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; furthermore,
the abovementioned radicals R.sup.3b are hydrogen,
C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl.
[0299] The tricyclic benzoic esters of the formula VIc or the
tricyclic benzoic acids of the formula VIb can be obtained by
reacting a tricyclic benzene derivative of the formula IX with a
C.sub.1-C.sub.6-alcohol or water in the presence of carbon
monoxide, a catalyst and a base. In general, the conditions
mentioned under process F apply. ##STR54##
[0300] L.sup.4 is a leaving group, such as halogen, for example
chlorine, bromine or iodine, or sulfate, such as mesylate or
triflate; preference is given to bromine or triflate.
[0301] Furthermore, the tricyclic benzoic acids of the formula VIb
can be obtained by converting a tricyclic benzene derivative of the
formula IX where L.sup.4 is halogen, such as chlorine or bromine,
in particular bromine, by reaction with, for example,
n-butyllithium or magnesium into the metalated derivative, followed
by quenching with carbon dioxide (cf., for example, J. Org. Chem.
1990, 55, 773; Angew. Chem. Int. Ed. 1969, 8, 68). ##STR55##
[0302] It is also possible to obtain the tricyclic benzoic acids
VIb by hydrolyzing the corresponding nitrites, analogously to
processes known from the literature. The nitriles for their part
can be obtained by halogen/nitrile exchange or by Sandmeyer
reaction from the corresponding anilines XV. ##STR56##
[0303] The compounds of the formula IX,
where:
[0304] X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2,
CR.sup.6R.sup.7, NR.sup.8 or a bond; [0305] Y together with the two
carbons to which it is attached forms a saturated, partially
saturated or unsaturated 5- or 6-membered heterocycle which
contains one to three identical or different heteroatoms selected
from the following group: oxygen, sulfur or nitrogen; [0306]
R.sup.1, R.sup.2, R.sup.6, R.sup.7 are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0307]
R.sup.3 is halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0308] R.sup.4 is nitro, halogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)
amino; [0309] R.sup.5 is hydrogen, C.sub.1-C.sub.6-alkyl or
halogen; [0310] R.sup.8 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, formyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
[0311] l is 0, 1 or 2; [0312] L.sup.4 is halogen,
C.sub.1-C.sub.6-alkylsulfonyloxy,
C.sub.1-C.sub.6-haloalkylsulfonyloxy or phenylsulfonyloxy, where
the phenyl ring of the lastmentioned radical may be unsubstituted
or partially or fully halogenated and/or may carry one to three of
the following radicals: nitro, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; are novel.
[0313] Preference is given to compounds of the formula IX where
L.sup.4 is halogen, in particular bromine.
[0314] The particularly preferred embodiments of the compounds of
the formula IX with respect to the variables X, Y, R.sup.1 to
R.sup.5 and l correspond to those of the tricyclic benzoylpyrazole
derivatives of the formula I.
[0315] Particular preference is given to the compounds of the
formula IX where [0316] Y together with the two carbons to which it
is attached forms the following heterocycles: ##STR57##
[0317] Here, extraordinary preference is given to the compounds IX
where [0318] R.sup.4 is nitro, halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio or C.sub.1-C.sub.6-alkylsulfonyl; in
particular C.sub.1-C.sub.6-alkylsulfonyl.
[0319] The compounds of the formula IX can be obtained in different
ways, the fused system, for example, can be constructed analogously
to the processes described for the compounds of the formula
VIc.
[0320] However, it is also possible to construct the fused system
from a suitable parent compound (analogously to the processes
described for compounds of the formula VIc) and to introduce
L.sup.4=halogen subsequently by customary halogenating
reactions.
[0321] The anilines of the formula XV and the nitriles of the
formula XVI ##STR58## where: [0322] X is oxygen, sulfur, S.dbd.O,
S(.dbd.O).sub.2, CR.sup.6R.sup.7, NR.sup.8 or a bond; [0323] Y
together with the two carbons to which it is attached forms a
saturated, partially saturated or unsaturated 5- or 6-membered
heterocycle which contains one to three identical or different
heteroatoms selected from the following group: oxygen, sulfur or
nitrogen; [0324] R.sup.1, R.sup.2, R.sup.6, R.sup.7 are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0325]
R.sup.3 is halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0326] R.sup.4 is nitro, halogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
aminosulfonyl, N--(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminosulfonyl,
N--(C.sub.1-C.sub.6-alkylsulfonyl) amino,
N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino,
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-alkylsulfonyl)amino
or
N--(C.sub.1-C.sub.6-alkyl)-N--(C.sub.1-C.sub.6-haloalkylsulfonyl)amino;
[0327] R.sup.5 is hydrogen, C.sub.1-C.sub.6-alkyl or halogen;
[0328] R.sup.8 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, formyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkoxycarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
[0329] l is 0, 1 or 2; are also novel.
[0330] The particularly preferred embodiments of the compounds of
the formulae XV and XVI with respect to the variables X, Y, R.sup.1
to R.sup.5 and l correspond to those of the tricyclic
benzoylpyrazole derivatives of the formula I.
[0331] Particular preference is given to the compounds of the
formula XV or XVI where [0332] Y together with the two carbons to
which it is attached forms the following heterocycles:
##STR59##
[0333] Here, extraordinary preference is given to the compounds XV
or XVI where [0334] R.sup.4 is nitro, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
C.sub.1-C.sub.6-alkylsulfonyl; in particular
C.sub.1-C.sub.6-alkylsulfonyl.
[0335] The compounds of the formula XV can be obtained in different
ways; for example, the fused system can be constructed analogously
to the processes described for the compounds of the formula
VIc.
[0336] However, it is also possible to construct the fused system
from a suitable parent compound (analogously to the processes
described for the compounds of the formula VIc) and to introduce a
nitro group subsequently by nitration para to R.sup.4, analogously
to processes known from the literature, and to convert this group
in a manner known per se by reduction into the amino group.
[0337] If appropriate, it may be advantageous in the synthesis
variants described above to introduce protective groups for certain
functionalities if the functionalities are not compatible with the
reaction conditions required.
[0338] The selection of the protective groups depends both on the
reaction conditions and on the structure of the molecule. The
protective groups, their introduction and their removal are
generally known from the literature (cf., for example, T. W. Greene
et al., "Protective Groups in Organic Synthesis", 2.sup.nd edition,
Wiley, New York, 1991), and they can be employed analogously to
processes known from the literature.
[0339] Furthermore, it may be necessary to carry out a combination
of the synthesis variants described above.
[0340] It is also possible to introduce further substitutents or to
modify the substitutents present by electrophilic, nucleophilic,
free-radical or organometallic reactions and by oxidation or
reduction reactions.
PREPARATION EXAMPLES
1.
(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4--
dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2)
2-Allyl-6-chlorobenzaldehyde
[0341] Under an atmosphere of protective gas, a solution of 10.89 g
(0.107 mol) of trimethylethylenediamine in 50 ml of anhydrous
tetrahydrofuran was cooled to -10.degree. C. and admixed dropwise
with 66.6 ml of a 1.6 molar solution of n-butyllithium in hexane
(0.107 mol). After 10 minutes, 15 g (0.107 mol) of
6-chlorobenzaldehyde in 70 ml of tetrahydrofuran were added
dropwise, and the mixture was admixed with a further 0.214 mol of
n-butyllithium in hexane (146.8 ml) and stirred at 0.degree. C. for
2.5 hours. The mixture was cooled to -20.degree. C., 12.42 g (0.139
mol) of copper(I) cyanide were added, the mixture was stirred at
-10.degree. C. for 30 minutes, and 28.42 g of allyl bromide in 100
ml of tetrahydrofuran were then added dropwise. The mixture was
stirred at 0.degree. C. for another 2.5 hours, and 230 ml of
saturated ammonium chloride solution were then added dropwise. The
resulting solid was separated off and the aqueous phase was
extracted with diethyl ether. The combined organic phases were then
washed with saturated ammonium chloride solution and dried, and the
solvent was removed under reduced pressure. This gave 17.0 g of
2-allyl-6-chlorobenzaldehyde (89%) in the form of a dark oil.
[0342] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.73 (d, 2H); 5.05
(dd, 2H); 5.96 (m, 1H); 7.05-7.48 (m, 3H); 10.58 (s, 1H).
2-Allyl-6-chlorobenzaldehyde oxime
[0343] 5.58 g of sodium bicarbonate were added to a solution of
4.62 g of hydroxylamine hydrochloride in 50 ml of water, and the
mixture was cooled to 0.degree. C. A solution of 9.7 g (44.32 mmol)
of 2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was then added
dropwise, and the mixture was stirred at room temperature
overnight. The methanol was subsequently removed under reduced
pressure and the residue was stirred into 300 ml of water. The
aqueous phase was extracted with diethyl ether and the combined
organic phases were washed with saturated ammonium chloride
solution and dried, and the solvent was removed. This gave 8.7 g
(quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in the form of
a viscous oil.
[0344] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.58 (d, 2H); 5.02
(2d, 2H); 5.95 (m, 1H); 7.08-7.36 (m, 3H); 8.49 (s, 1H).
8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazole
[0345] At room temperature, 37.0 ml of a sodium hypochlorite
solution (12.5% of active chlorine) were added dropwise to a
solution of 8.4 g (42.9 mmol) of 2-allyl-6-chlorobenzaldehyde oxime
in 100 ml of methylene chloride, and a spatula tip of sodium
acetate was added. The mixture was stirred at room temperature for
2 hours, the organic phase was separated off, the aqueous phase was
extracted with methylene chloride and the combined organic phases
were washed with saturated ammonium chloride solution. The organic
phase was dried and the solvent was removed. This gave 7.0 g (94%)
of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in the form of
a viscous oil.
[0346] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 2.81 (dd, 1H);
3.24 (dd, 1H); 3.78-4.03 (s, 2H); 4.78 (t, 1H); 7.23-7.41 (m,
3H).
8-Methylthio-3a,4-dihydro-3H-indeno[1,2c]isoxazole
[0347] At room temperature, 3.6 g (52.0 mmol) of sodium
thiomethoxide were added to a solution of 5.0 g (25.8 mmol) of
8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in 60 ml of
N-methylpyrrolidone, and the mixture was stirred overnight. The
mixture was subsequently stirred into 800 ml of water, the aqueous
phase was extracted with diethyl ether, the combined organic phases
were washed with saturated ammonium chloride solution and dried,
and the solvent was removed. This gave 4.6 g (87%) of
8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole in the form of
a dark brown solid.
[0348] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 2.54 (s, 3H); 2.78
(dd, 1H); 3.21 (dd, 1H); 3.72-3.93 (s, 2H); 4.64 (t, 1H); 7.09-7.38
(m, 3H).
5-Bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole
[0349] 120 ml of sulfuric acid (98 percent strength) were cooled to
0.degree. C., and 11.2 g (54.8 mmol) of
8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole were added a
little at a time. 9.2 g (57.5 mmol) of bromine were then added
dropwise, and stirring was continued at 0.degree. C. for another 2
hours. The resulting solution was poured into 2 l of a mixture of
water and ice, this mixture was stirred for 1.5 hours and the
precipitated solid was filtered off with suction and then washed
and dried. This gave 11.4 g (73%) of
5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole of a
brown solid having a m.p. of 127-135.degree. C.
[0350] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 2.53 (s, 3H); 2.71
(dd, 1H); 3.24 (dd, 1H); 3.81-4.02 (s, 2H); 4.71 (t, 1H); 7.01 (d,
1H); 7.47 (d, 1H).
5-Bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole
[0351] A solution of 11.2 g (39.4 mmol) of
5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole and
1.55 g of sodium tungstate in 250 ml of toluene and 50 ml of
glacial acetic acid was heated to 70.degree. C. and mixed dropwise
with 10.73 g (39 percent strength, 86.8 mmol) of hydrogen peroxide.
Stirring was continued at 70.degree. C. for another 3 hours, and a
solid precipitated out. The mixture was allowed to cool to room
temperature and stirred into 1 l of water, and the white solid was
filtered off with suction. The organic phase of the filtrate was
separated off and the aqueous phase was extracted with ethyl
acetate. The combined organic phases were washed with water and
dried, and the solvent was removed. This gave a viscous brown oil
which was stirred with hexane/ethyl acetate (4:1). The resulting
precipitate was filtered off with suction and combined with the
solid obtained above. This gave 7.3 g (59%) of
5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole.
[0352] .sup.1H-NMR (d.sup.6-DMSO, .delta. in ppm): 2.93 (dd, 1H);
3.23 (dd, 1H); 3.41 (s, 3H); 3.94 (dd, 1H); 4.16 (m, 1H); 4.81 (t,
1H); 7.82 (d, 1H); 8.03 (d, 1H).
(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-ind-
eno[1,2-c]isoxazol-5-yl)methanone (compound 2.1)
[0353] 0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g
(12.66 mmol) of dry potassium carbonate, 1.28 g (12.67 mmol) of
triethylamine and 0.22 g (0.30 mmol) of
bis-(triphenylphosphane)palladium dichloride were added to a
suspension of 2.0 g (6.33 mmol) of
5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in
100 ml of dioxane. In a miniautoclave, a carbon monoxide pressure
of 20 bar was applied, the mixture was stirred for 5 minutes and
the autoclave was vented. This procedure was repeated 3 times. The
autoclave was subsequently heated to 130.degree. C., a carbon
monoxide pressure of 20 bar was applied once more and the mixture
was stirred for 24 hours. After cooling and venting, the solvent
was removed, and the residue was taken up in water, adjusted to pH
11 and washed with methylene chloride. The mixture was subsequently
acidified to pH 4 using 10 percent strength hydrochloric acid and
extracted with methylene chloride. The combined organic phases were
washed with saturated ammonium chloride solution and dried, and the
solvent was removed. This gave 0.58 g (25%) of
(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-in-
deno[1,2-c]isoxazole)-methanone in the form of a dark oil.
[0354] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.03 (dd, 1H);
3.42 (s, 3H); 3.40 (m, 1H); 3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t,
1H); 7.57 (s, 1H); 7.92 (d, 1H); 8.22 (d, 1H).
(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihy-
dro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2)
[0355] Under an atmosphere of protective gas, 0.18 g of
triethylamine and 0.26 g (1.82 mmol) of benzoyl chloride in 10 ml
of tetrahydrofuran were added at 0.degree. C. to a suspension of
0.55 g (1.52 mmol) of
(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-in-
deno[1,2-c]-isoxazol-5-yl)methanone in 10 ml of tetrahydrofuran.
The mixture was stirred overnight at room temperature, the solvent
was removed, the residue was taken up in ethyl acetate, washed with
water and dried, and the solvent was removed. The crude product was
purified by silica gel chromatography (mobile phase: ethyl
acetate:hexane=1:1). This gave 0.22 g (31%) of
(5-phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dih-
ydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone in the form of a
yellow solid having a m.p. of 86-93.degree. C.
[0356] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.22 (s, 3H); 3.34
(m, 2H); 3.81 (s, 3H); 3.98 (m, 2H); 4.81 (t, 1H); 7.20-8.21 (m,
8H).
2.
4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)carbonyl-5-hyd-
roxy-1-methyl-1H-pyrazole (compound 3.1)
Methyl 2-chlorosulfonyl-4-chlorobenzoate
[0357] At from 0 to 5.degree. C., a solution of 60.9 g (0.88 mol)
of sodium nitrite in 100 ml of water was added dropwise to a
solution of 139 g (0.75 mol) of methyl 2-amino-4-chlorobenzoate in
400 ml of concentrated hydrochloric acid and the mixture was
stirred at 0.degree. C. for another hour.
[0358] In a second apparatus, 3 g of copper(II) chloride, 3 g of
benzyltriethylammonium chloride, 10 ml of water and 400 ml of
1,2-dichloroethane were combined and 64 g (1 mol) of sulfur dioxide
were introduced.
[0359] The diazonium salt described above was subsequently added at
from 10 to 15.degree. C., and the mixture was slowly heated to
50.degree. C. A further 54 g (0.84 mol) of sulfur dioxide were then
introduced, and stirring was continued at 50.degree. C. for another
30 minutes. After cooling, 7.4 g (0.1 mol) of chlorine gas were
then introduced at room temperature, stirring was continued for 15
minutes and the phases which had formed were then separated. The
organic phase was dried and the solvent was removed. This gave 207
g of methyl 2-chlorosulfonyl-4-chlorobenzoate.
[0360] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 4.00 (s, 3H); 7.75
(m, 2H); 8.18 (m, 1H)
Methyl 2-mercapto-4-chlorobenzoate
[0361] Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder
were added a little at a time to a suspension of 205 g (0.75 mol)
of methyl 2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated
hydrochloric acid and 375 g of ice. The mixture was stirred for
another 3 hours and slowly heated to 70.degree. C. After 2 hours at
this temperature, the mixture was cooled. The reaction mixture was
allowed to stand at room temperature for 12 hours and then
extracted with ethyl acetate, the combined organic phases were
dried and the solvent was removed. This gave 125.4 g (83%) of
methyl 2-mercapto-4-chlorobenzoate.
[0362] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.95 (s, 3H); 4.88
(s, 1H); 7.10 (m, 1H); 7.30 (m, 1H); 7.96 (d, 1H).
Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate
[0363] 179.5 g (1.3 mol) of potassium carbonate and, a little at a
time, 94.5 g (0.62 mol) of 3-bromopropionic acid were added to a
solution of 125.4 g (0.62 mol) of methyl
2-mercapto-4-chlorobenzoate in 1.5 l of acetone, and the reaction
mixture was stirred at room temperature for 12 hours. The solvent
was distilled off, the residue was taken up in water and the
mixture was extracted with diethyl ether. The aqueous phase was
then made acidic using concentrated hydrochloric acid, and the
resulting precipitate was filtered off with suction and dried. This
gave 150 g (88%) of methyl
2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate.
[0364] M.p.: 133 to 136.degree. C.
Methyl 5-chloro-4-oxothiochromane-8-carboxylate
[0365] At 70.degree. C., 50 g (0.18 mol) of methyl
2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate were added to
500 g of polyphosphoric acid, and the mixture was stirred for a
further 30 minutes. The reaction mixture was then stirred into
water and the resulting precipitate was filtered off with suction
and dried. This gave 41.1 g (88%) of methyl
5-chloro-4-oxothiochromane-8-carboxylate.
[0366] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.08 (m, 4H); 3.96
(s, 3H); 7.14 (d, 1H); 7.95 (d, 1H).
Methyl
5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carbo-
xylate
[0367] 30 g (0.078 mol) of methyl
5-chloro-4-oxothiochromane-8-carboxylate in 300 ml of
N,N-dimethylformamide dimethyl acetal were refluxed for 6 hours.
Volatile components were then distilled off, the residue was taken
up in methylene chloride and the organic phase washed with water.
Drying and removal of the solvent gave 35.3 g (97%) of methyl
5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate-
.
[0368] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.18 (s, 6H); 3.80
(s, 2H); 3.95 (s, 3H); 7.24 (d, 1H); 7.64 (s, 1H); 7.82 (d,
1H).
2-Methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole
[0369] 1.3 g (29.2 mmol) of methylhydrazine were added dropwise to
a solution of 7.0 g (22.5 mmol) of methyl
5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate
in 700 ml of ethanol, and the mixture was refluxed for 2 hours. The
solvent was removed and the residue was chromatographed over silica
gel using ethyl acetate/cyclohexane (2:3) as mobile phase. This
gave 4.0 g (60%) of
2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyraz-
ole.
[0370] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.76 (s, 2H); 3.95
(s, 3H); 4.00 (s, 3H); 7.24 (s, 1H); 7.36 (d, 1H); 7.70 (d,
1H).
2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole
[0371] 4.0 g (13.6 mmol) of
2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole
in 100 ml of methanol/water (1:1) were refluxed with 0.8 g (20
mmol) of sodium hydroxide for 1 hour. The organic solvent was
removed under reduced pressure and the residue was extracted with
ethyl acetate. The aqueous phase was acidified using concentrated
hydrochloric acid and the resulting precipitate was filtered off
with suction and dried. This gave 3.5 g (92%) of
2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole
[0372] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.80 (s, 2H); 3.96
(s, 3H); 7.40 (d, 1H); 7.65 (m, 2H).
4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydro-
xy-1-methyl-1H-pyrazole (compound 3.1)
[0373] A mixture of 0.60 g (2.1 mmol) of
2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole
and 0.21 g (2.1 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of
acetonitrile was stirred at room temperature overnight. The mixture
was admixed with in each case 500 ml of ethyl acetate and 2%
strength sodium carbonate solution, the resulting precipitate was
filtered off, the organic phase was dried and the solvent was
removed. The residue was then refluxed with 0.59 g (4.3 mmol) of
potassium carbonate in 5 ml of 1,4-dioxane for 3 hours. After
cooling, the mixture was extracted with diethyl ether and the
aqueous phase was acidified to pH 3. The resulting precipitate was
filtered off with suction and dried. This gave 0.14 g of
4-(2-methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydr-
oxy-1-methyl-1H-pyrazole.
[0374] M.p.: 168-171.degree. C.
3.
(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromen-
o[4,3-c]isoxazolin-9-yl)methanone (compound 2.3)
Methyl 2-hydroxy-3-formyl-4-methoxybenzoate
[0375] At from 0 to 5.degree. C., a solution of 209.0 g (1.1 mol)
of titanium tetrachloride in 150 ml of methylene chloride was added
dropwise to a solution of 50.1 g (0.275 mol) of methyl
2-hydroxy-4-methoxybenzoate and 88 g (0.725 mol) of
dichloromethoxymethane in 400 ml of methylene chloride, and the
mixture was stirred at room temperature overnight. The mixture was
then stirred into ice-water and extracted with methylene chloride.
The combined organic phases were washed with sodium bicarbonate
solution, water and sodium chloride solution and dried, and the
solvent was then removed. Silica gel chromatography using
cyclohexane/ethyl acetate=1:1 gave 24.5 g (42%) of methyl
2-hydroxy-3-formyl-4-methoxybenzoate in the form of a colorless
solid of m.p.: 123-124.degree. C.
[0376] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.92 (s, 3H); 3.98
(s, 3H); 6.49 (d, 1H); 8.19 (d, 1H); 10.39 (s, 1H).
Methyl 2-allyloxy-3-formyl-4-methoxybenzoate
[0377] At room temperature, 23.2 g (0.192 mol) of allyl bromide
were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium
hydroxide and 20.2 g (0.096 mol) of methyl
2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl
sulfoxide, and the mixture was stirred at room temperature for 4
hours. The mixture was subsequently stirred into 1.5 l of 3%
strength aqueous hydrochloric acid and extracted with ethyl
acetate. The combined organic phases were washed with water and
dried, and the solvent was removed. Silica gel chromatography using
cyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl
2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish
oil.
[0378] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.86 (s, 3H); 3.93
(s, 3H); 4.58 (d, 2H); 5.32 (d, 1H); 5.39 (d, 1H); 6.15 (m, 1H);
6.79 (d, 1H); 8.04 (d, 1H); 10.41 (s, 1H).
6-Methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
[0379] Step a)
[0380] At room temperature, 4.6 g (18.4 mmol) of methyl
2-allyloxy-3-formyl-4-methoxybenzoate in 70 ml of methanol were
added dropwise to a solution of 2.25 g (32.3 mmol) of
hydroxylammonium chloride and 2.7 g of pyridine in 70 ml of water.
The mixture was stirred at room temperature overnight, 150 ml of
water were added, the mixture was extracted with methylene
chloride, the combined organic phases were washed with 3% strength
aqueous hydrochloric acid and dried, and the solvent was removed.
The resulting oxime has a melting point of 126-129.degree. C.
[0381] Step b)
[0382] This oxime was reacted further without any further
purification by dissolving it in 40 ml of methylene chloride,
followed by dropwise addition of 15.0 ml (25.0 mmol) of sodium
hypochlorite solution (12.5% of active chlorine). A spatula tip of
sodium acetate was added and the mixture was stirred at room
temperature for 12 hours. The organic phase was separated off, the
aqueous phase was extracted with methylene chloride, the combined
organic phases were washed with water and dried, and the solvent
was removed. Silica gel chromatography using cyclohexane/ethyl
acetate=1:1 gave 2.2 g (49%) of
6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline
in the form of a colorless solid of m.p: 199-203.degree. C.
[0383] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.84 (s, 3H); 3.98
(s, 3H); 3.8-4.0 (m, 2H); 4.16 (dt, 1H); 4.63 (t, 1H); 4.84 (dd,
1H); 6.61 (d, 1H); 7.93 (d, 1H).
6-Methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
[0384] At room temperature, a solution of 0.8 g (20.0 mmol) of
sodium hydroxide in 7 ml of water was added dropwise to a solution
of 2.1 g (8.0 mmol) of
6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxa-
zoline in 40 ml of methanol, and the mixture was refluxed for 6
hours. After cooling, the solvent was removed and the residue was
taken up in about 50 ml of water and washed with methylene
chloride. The aqueous phase was subsequently acidified using 10%
strength hydrochloric acid (pH=1-2), and the precipitate was
filtered off with suction, washed with water and dried at
60.degree. C. This gave 1.7 g (86%) of
6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline
in the form of colorless crystals.
[0385] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.73 (dd, 1H);
3.89 (s, 3H); 3.84-3.95 (m, 1H); 4.11 (dd, 1H); 4.54 (dd, 1H); 4.79
(dd, 1H); 6.61 (d, 1H); 7.81 (d, 1H).
(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4-
,3-c]isoxazolin-9-yl)methanone (compound 2.3)
[0386] Step a)
[0387] At room temperature, 0.26 g (2.2 mmol) of thionyl chloride
and a drop of dimethylformamide were added to a solution of 0.50 g
(2.0 mmol) of
6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[(4,3-c)]isoxazoli-
ne in 30 ml of carbon tetrachloride, and the mixture was stirred at
40-50.degree. C. for 3 hours. The solvent was subsequently removed
under reduced pressure. This gave, in quantitative yield,
6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
(0.54 g) as a brownish oil.
[0388] Step b)
[0389] 0.54 g (2 mmol) of
6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
was dissolved in 30 ml of acetonitrile and, at 0.degree. C., added
dropwise to a solution of 0.2 g (2.0 mmol) of
1-methyl-5-hydroxypyrazole and 0.6 g (6.0 mmol) of triethylamine in
20 ml of acetonitrile. The mixture was stirred at room temperature
overnight, the solvent was removed, and the residue was taken up in
methylene chloride and washed with water. The solution was dried
and the solvent was distilled off. The residue was dissolved in 30
ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassium
carbonate, and the mixture was refluxed for 7 hours. After cooling,
the solvent was distilled off under reduced pressure, the residue
was taken up in water and the solution was adjusted to pH=1 using
10% strength hydrochloric acid. The solution was extracted with
methylene chloride, the combined organic phases were dried and the
solvent was subsequently removed. This gave 0.45 g (68%) of
(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[-
4,3-c]isoxazolin-9-yl)methanone of m.p. 236-238.degree. C.
[0390] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 3.66 (s, 3H);
3.84-4.2 (m, 2H); 4.02 (s, 3H); 4.12 (dd, 1H); 4.63-4.77 (m, 2H);
6.68 (d, 1H); 7.24 (s, 1H); 7.61 (d, 1H).
4.
[5-Hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-di-
hydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone (compound
2.4)
[0391] 0.54 g (2 mmol) of
6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline
was dissolved in 30 ml of acetonitrile and, at 0.degree. C., added
dropwise to a solution of 0.28 g (2.0 mmol) of
1-(1,1-dimethyleth-1-yl)-5-hydroxy-1H-pyrazole and 0.6 g (6.0 mmol)
of triethylamine in 20 ml of acetonitrile. The mixture was stirred
at room temperature overnight, the solvent was removed, and the
residue was taken up in methylene chloride and washed with water.
The solution was dried, and the solvent was distilled off. The
residue was dissolved in 30 ml of dioxane and admixed with 0.42 g
(3.0 mmol) of potassium carbonate, and the mixture was refluxed for
7 hours. After cooling, the solvent was distilled off under reduced
pressure, the residue was taken up in water and the solution was
adjusted to pH=1 using 10% strength hydrochloric acid. The solution
was extracted with methylene chloride, the combined organic phases
were dried, and the solvent was subsequently removed. This gave 0.3
g (40%) of
[5-hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihy-
dro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone having a melting
point of 223.degree. C.-225.degree. C.
[0392] .sup.1H NMR (CDCl.sub.3, .delta. in ppm): 1.64 (s, 9H);
3.8-4.2 (m, 6H); 4.6-4.8 (m, 2H); 6.68 (d, 1H); 7.44 (s, 1H); 7.62
(d, 1H).
[0393] In addition to the compounds above, other tricyclic
benzoylpyrazole derivatives of the formula I which were prepared or
are preparable in a similar manner are listed in Tables 2 to 5:
TABLE-US-00002 TABLE 2 ##STR60## physical data (m.p. [.degree. C.];
No. X R.sup.4 R.sup.10 R.sup.11 R.sup.12 .sup.1H NMR [ppm]) 2.1
Bond SO.sub.2CH.sub.3 OH CH.sub.3 H 3.03 (dd, 1H); 3.42 (s, 3H);
3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t, 1H); 7.57 (s, 1H); 7.92 (d,
1H); 8.22 (d, 1H) 2.2 Bond SO.sub.2CH.sub.3 OCOC.sub.6H.sub.5
CH.sub.3 H 3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98 (m, 2H);
4.81 (t, 1H); 7.20-8.21 (m, 8H); 2.3 O OCH.sub.3 OH CH.sub.3 H
236-238 2.4 O OCH.sub.3 OH C(CH.sub.3).sub.3 H 223-225 2.5 O
OCH.sub.3 OCO (3-F--C.sub.6H.sub.4) CH.sub.3 H oil
[0394] TABLE-US-00003 TABLE 3 ##STR61## No. X R.sup.4 R.sup.10
R.sup.11 R.sup.12 physical data (m.p.[.degree. C]) 3.1 S Cl OH
CH.sub.3 H 168-171 3.2 S Cl OH CH.sub.2CH.sub.3 H 115 3.3 S
SCH.sub.3 OH CH.sub.3 H 245 3.4 S SCH.sub.3 OH CH.sub.2CH.sub.3 H
222
[0395] TABLE-US-00004 TABLE 4 ##STR62## physical data (m.p.
[.degree. C.]; No. X R.sup.4 R.sup.10 R.sup.11 R.sup.12 .sup.1H NMR
[ppm]) 4.1 S Cl OH CH.sub.3 H 180.degree. C. 4.2 S Cl OH
CH.sub.2CH.sub.3 H 112.degree. C.
[0396] TABLE-US-00005 TABLE 5 ##STR63## physical data (m.p.
[.degree. C.]; Nr. X R.sup.4 R.sup.10 R.sup.11 R.sup.12 .sup.1H NMR
[ppm]) 5.1 O SCH.sub.3 OH CH.sub.3 H 201
[0397] The compounds of the formula I and their agriculturally
useful salts are suitable, both in the form of isomer mixtures and
in the form of the pure isomers, as herbicides. The herbicidal
compositions comprising compounds of the formula I control
vegetation on non-crop areas very efficiently, especially at high
rates of application. They act against broad-leaved weeds and grass
weeds in crops such as wheat, rice, maize, soya and cotton without
causing any significant damage to the crop plants. This effect is
mainly observed at low rates of application.
[0398] Depending on the application method in question, the
compounds of the formula I, or herbicidal compositions comprising
them, can additionally be employed in a further number of crop
plants for eliminating undesirable plants. Examples of suitable
crops are the following:
[0399] Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus
officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec.
rapa, Brassica napus var. napus, Brassica napus var. napobrassica,
Brassica rapa var. silvestris, Camellia sinensis, Carthamus
tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis,
Coffea arabica (Coffea canephora, Coffea liberica), Cucumis
sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,
Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium
arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus
annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus,
Ipomoea batatas, Juglans regia, Lens culinaris, Linum
usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot
esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.
rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus
vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium,
Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis,
Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum
bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum
aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea
mays.
[0400] In addition, the compounds of the formula I may also be used
in crops which tolerate the action of herbicides owing to breeding,
including genetic engineering methods.
[0401] The compounds of the formula I, or the herbicidal
compositions comprising them, can be used for example in the form
of ready-to-spray aqueous solutions, powders, suspensions, also
highly-concentrated aqueous, oily or other suspensions or
dispersions, emulsions, oil dispersions, pastes, dusts, materials
for broadcasting, or granules, by means of spraying, atomizing,
dusting, spreading or watering. The use forms depend on the
intended purpose; in any case, they should guarantee the finest
possible distribution of the active compounds according to the
invention.
[0402] The herbicidal compositions comprise a herbicidally
effective amount of at least one compound of the formula I or an
agriculturally useful salt of I and auxiliaries which are
customarily used for formulating crop protection agents.
[0403] Suitable for use as inert auxiliaries are essentially the
following:
[0404] mineral oil fractions of medium to high boiling point, such
as kerosene and diesel oil, furthermore coal-tar oils and oils of
vegetable or animal origin, aliphatic, cyclic and aromatic
hydrocarbons, for example paraffin, tetrahydronaphthalene,
alkylated naphthalenes and their derivatives, alkylated benzenes or
their derivatives, alcohols such as methanol, ethanol, propanol,
butanol and cyclohexanol, ketones such as cyclohexanone, strongly
polar solvents, for example amines such as N-methylpyrrolidone, and
water.
[0405] Aqueous use forms can be prepared from emulsion
concentrates, suspensions, pastes, wettable powders or
water-dispersible granules by adding water. To prepare emulsions,
pastes or oil dispersions, the tricyclic benzoylpyrazole
derivatives of the formula I, either as such or dissolved in an oil
or solvent, can be homogenized in water by means of a wetting
agent, tackifier, dispersant or emulsifier. Alternatively, it is
possible to prepare concentrates comprising active compound,
wetting agent, tackifier, dispersant or emulsifier and, if desired,
solvent or oil, which are suitable for dilution with water.
[0406] Suitable surfactants are the alkali metal salts, alkaline
earth metal salts and ammonium salts of aromatic sulfonic acids,
e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic
acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl
sulfates, lauryl ether sulfates and fatty alcohol sulfates, and
salts of sulfated hexa-, hepta- and octadecanols, and also of fatty
alcohol glycol ethers, condensates of sulfonated naphthalene and
its derivatives with formaldehyde, condensates of naphthalene or of
the naphthalenesulfonic acids with phenol and formaldehyde,
polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or
nonylphenol, alkylphenyl or tributylphenyl polyglycol ether,
alkylaryl polyether alcohols, isotridecyl alcohol, fatty
alcohol/ethylene oxide condensates, ethoxylated castor oil,
polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers,
lauryl alcohol polyglycol ether acetate, sorbitol esters,
lignin-sulfite waste liquors or methylcellulose.
[0407] Powders, materials for broadcasting and dusts can be
prepared by mixing or grinding the active compounds together with a
solid carrier.
[0408] Granules, e.g. coated granules, impregnated granules and
homogeneous granules, can be prepared by binding the active
compounds to solid carriers. Solid carriers are mineral earths such
as silicas, silica gels, silicates, talc, kaolin, limestone, lime,
chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium
sulfate, magnesium sulfate and magnesium oxide, ground synthetic
materials, fertilizers such as ammonium sulfate, ammonium
phosphate, ammonium nitrate and ureas, and products of vegetable
origin, such as cereal meal, tree bark meal, wood meal and nutshell
meal, cellulose powders, or other solid carriers.
[0409] The concentrations of the compounds of the formula I in the
ready-to-use preparations can be varied within wide ranges. In
general, the formulations comprise approximately from 0.001 to 98%
by weight, preferably 0.01 to 95% by weight, of at least one active
compound. The active compounds are employed in a purity of from 90%
to 100%, preferably 95% to 100% (according to NMR spectrum).
[0410] The following formulation examples illustrate the
preparation of such formulations: [0411] I. 20 parts by weight of
the compound No. 2.2 are dissolved in a mixture composed of 80
parts by weight of alkylated benzene, parts by weight of the adduct
of from 8 to 10 mol of ethylene oxide to 1 mol of oleic acid
N-monoethanolamide, 5 parts by weight of calcium salt of
dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of
40 mol of ethylene oxide to 1 mol of castor oil. Pouring the
solution into 100,000 parts by weight of water and finely
distributing it therein gives an aqueous dispersion which comprises
0.02% by weight of the active compound. [0412] II. 20 parts by
weight of the compound No. 3.1 are dissolved in a mixture composed
of 40 parts by weight of cyclohexanone, 30 parts by weight of
isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene
oxide to 1 mol of isooctylphenol and 10 parts by weight of the
adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring
the solution into 100,000 parts by weight of water and finely
distributing it therein gives an aqueous dispersion which comprises
0.02% by weight of the active compound. [0413] III. 20 parts by
weight of the compound No. 2.3 are dissolved in a mixture composed
of 25 parts by weight of cyclohexanone, 65 parts by weight of a
mineral oil fraction of boiling point 210 to 280.degree. C. and 10
parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol
of castor oil. Pouring the solution into 100,000 parts by weight of
water and finely distributing it therein gives an aqueous
dispersion which comprises 0.02% by weight of the active compound.
[0414] IV. 20 parts by weight of the compound No. 2.4 are mixed
thoroughly with 3 parts by weight of the sodium salt of
diisobutylnaphthalenesulfonic acid, 17 parts by weight of the
sodium salt of a lignosulfonic acid from a sulfite waste liquor and
60 parts by weight of pulverulent silica gel, and the mixture is
ground in a hammer mill. Finely distributing the mixture in 20,000
parts by weight of water gives a spray mixture which comprises 0.1%
by weight of the active compound. [0415] V. 3 parts by weight of
the compound No. 2.3 are mixed with 97 parts by weight of finely
divided kaolin. This gives a dust which comprises 3% by weight of
the active compound. [0416] VI. 20 parts by weight of the compound
No. 2.4 are mixed intimately with 2 parts by weight of calcium salt
of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol
polyglycol ether, 2 parts by weight of sodium salt of a
phenol/urea/formaldehyde condensate and 68 parts by weight of a
paraffinic mineral oil. This gives a stable oily dispersion. [0417]
VII. 1 part by weight of the compound No. 2.2 is dissolved in a
mixture composed of 70 parts by weight of cyclohexanone, 20 parts
by weight of ethoxylated isooctylphenol and 10 parts by weight of
ethoxylated castor oil. This gives a stable emulsion concentrate.
[0418] VIII. 1 part by weight of the compound No. 3.1 is dissolved
in a mixture composed of 80 parts by weight of cyclohexanone and 20
parts by weight of Wettol.RTM. EM 31 (=nonionic emulsifier based on
ethoxylated castor oil). This gives a stable emulsion
concentrate.
[0419] The compounds of the formula I or the herbicidal
compositions can be applied pre- or post-emergence. If the active
compounds are less well tolerated by certain crop plants,
application techniques may be used in which the herbicidal
compositions are sprayed, with the aid of the spraying equipment,
in such a way that as far as possible they do not come into contact
with the leaves of the sensitive crop plants, while the active
compounds reach the leaves of undesirable plants growing
underneath, or the bare soil surface (post-directed, lay-by).
[0420] The rates of application of the compound of the formula I
are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active
substance (a.s.), depending on the control target, the season, the
target plants and the growth stage.
[0421] To widen the spectrum of action and to achieve synergistic
effects, the tricyclic benzylpyrazole derivatives of the formula I
may be mixed with a large number of representatives of other
herbicidal or growth-regulating active compound groups and applied
concomitantly. Suitable components for mixtures are, for example,
1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric
acid and its derivatives, aminotriazoles, anilides,
aryloxy-/heteroaryloxyalkanoic acids and their derivatives, benzoic
acid and its derivatives, benzothiadiazinones,
2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones,
benzylisoxazolidinones, meta-CF.sub.3-phenyl derivatives,
carbamates, quinoline carboxylic acid and its derivatives,
chloroacetanilides, cyclohexenone oxime ether derivatives,
diazines, dichloropropionic acid and its derivatives,
dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines,
dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids
and their derivatives, ureas, 3-phenyluracils, imidazoles,
imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,
oxadiazoles, oxiranes, phenols, aryloxy- and
hetaryloxyphenoxypropionic esters, phenylactic acid and its
derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,
phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its
derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas,
triazines, triazinones, triazolinones, triazolecarboxamides and
uracils.
[0422] It may furthermore be advantageous to apply the compounds of
the formula I, alone or in combination with other herbicides, in
the form of a mixture with other crop protection agents, for
example together with agents for controlling pests or
phytopathogenic fungi or bacteria. Also of interest is the
miscibility with mineral salt solutions, which are employed for
treating nutritional and trace element deficiencies. Non-phytotoxic
oils and oil concentrates may also be added.
USE EXAMPLES
[0423] The herbicidal activity of the tricyclic benzylpyrazole
derivatives of the formula I was demonstrated by the following
greenhouse experiments:
[0424] The culture containers used were plastic pots containing
loamy sand with approximately 3.0% of humus as the substrate. The
seeds of the test plants were sown separately for each species.
[0425] For the pre-emergence treatment, the active compounds, which
had been suspended or emulsified in water, were applied directly
after sowing by means of finely distributing nozzles. The
containers were irrigated gently to promote germination and growth
and subsequently covered with transparent plastic hoods until the
plants had rooted. This cover causes uniform germination of the
test plants, unless this was adversely affected by the active
compounds.
[0426] For post-emergence treatment, the test plants were first
grown to a plant height of from 3 to 15 cm, depending on the plant
habit, and only then treated with the active compounds which had
been suspended or emulsified in water. For this purpose, the test
plants were either sown directly and grown in the same containers,
or they were first grown separately as seedlings and transplanted
into the test containers a few days prior to the treatment. The
application rate for the post-emergence treatment was 0.5 or 0.25
kg of a.s./ha.
[0427] Depending on the species, the plants were kept at
10-25.degree. C. or 20-35.degree. C. The test period extended over
2 to 4 weeks. During this time, the plants were tended, and their
response to the individual treatments was evaluated.
[0428] Evaluation was carried out using a scale from 0 to 100. 100
means no emergence of the plants, or complete destruction of at
least the above-ground parts, and 0 means no damage, or normal
course of growth.
[0429] The plants used in the greenhouse trials were of the
following species: TABLE-US-00006 Scientific Name Common Name
Chenopodium album lambsquarters (goosefoot) Echinochloa crusgalli
barnyardgrass Setaria viridis green foxtail Solanum nigrum black
nightshade Veronica ssp. speadwell
[0430] At application rates of 0.5 or 0.25 kg/ha, the compound 2.2
shows very good activity against the abovementioned undesired
broad-leaved weeds and weed grasses when applied by the
post-emergence method.
* * * * *