U.S. patent application number 10/954396 was filed with the patent office on 2005-04-14 for substituted benzoylisoxazoles and the use thereof as herbicides.
Invention is credited to Drewes, Mark Wilhelm, Feucht, Dieter, Lehr, Stefan, Muller, Klaus-Helmut, Pontzen, Rolf, Schallner, Otto, Schwarz, Hans-Georg, Wetcholowsky, Ingo, Wroblowsky, Heinz-Jurgen.
Application Number | 20050079979 10/954396 |
Document ID | / |
Family ID | 7907127 |
Filed Date | 2005-04-14 |
United States Patent
Application |
20050079979 |
Kind Code |
A1 |
Muller, Klaus-Helmut ; et
al. |
April 14, 2005 |
Substituted benzoylisoxazoles and the use thereof as herbicides
Abstract
The invention relates to novel substituted benzoylisoxazoles of
the general formula (I), 1 in which n, A, R.sup.1, R.sup.2,
R.sup.3, R.sup.4, and Z are defined herein, and to processes for
their preparation and to their use as herbicides.
Inventors: |
Muller, Klaus-Helmut;
(Dusseldorf, DE) ; Lehr, Stefan; (Langenfeld,
DE) ; Schallner, Otto; (Monheim, DE) ;
Schwarz, Hans-Georg; (Langenfeld, DE) ; Wroblowsky,
Heinz-Jurgen; (Langenfeld, DE) ; Drewes, Mark
Wilhelm; (Langenfeld, DE) ; Feucht, Dieter;
(Monheim, DE) ; Pontzen, Rolf; (Leichlingen,
DE) ; Wetcholowsky, Ingo; (Cond. Estancia Marambaia,
BR) |
Correspondence
Address: |
BAYER CROPSCIENCE LP
Patent Department
100 BAYER ROAD
PITTSBURGH
PA
15205-9741
US
|
Family ID: |
7907127 |
Appl. No.: |
10/954396 |
Filed: |
September 30, 2004 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10954396 |
Sep 30, 2004 |
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09980666 |
Nov 2, 2001 |
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6838415 |
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09980666 |
Nov 2, 2001 |
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PCT/EP00/03608 |
Apr 20, 2000 |
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Current U.S.
Class: |
504/225 ;
548/374.1 |
Current CPC
Class: |
A01N 43/80 20130101;
C07D 249/12 20130101; A01N 43/90 20130101; C07D 413/10 20130101;
C07D 261/08 20130101 |
Class at
Publication: |
504/225 ;
548/374.1 |
International
Class: |
A01N 043/84; C07D
231/12 |
Foreign Application Data
Date |
Code |
Application Number |
May 6, 1999 |
DE |
199 20 791.7 |
Claims
1-21. (canceled)
22. A compound of the Formula (IE) 766in which n represents the
number 0, 1 or 2, A represents a single bond or represents
alkanediyl (alkylene) having 1 to 4 carbon atoms, R.sup.1
represents hydrogen, represents optionally cyano-, halogen-,
C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substituted alkyl having 1 to 6
carbon atoms, represents optionally cyano- or halogen-substituted
alkenyl having 2 to 6 carbon atoms, or represents optionally
cyano-, halogen- or C.sub.1-C.sub.4-alkyl-substituted cycloalkyl
having 3 to 6 carbon atoms, R.sup.2 represents hydrogen, cyano,
carbamoyl, halogen, represents in each case optionally cyano-,
halogen-, C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substituted alkyl, alkylcarbonyl,
alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms,
or represents optionally halogen-substituted alkylthio,
alkylsulphinyl or alkylsulphonyl having 1 to 6 carbon atoms,
R.sup.3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl,
thiocarbamoyl, halogen, represents in each case optionally
halogen-, C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substituted alkyl, alkoxy,
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up
to 4 carbon atoms in the alkyl groups, or represents alkylamino,
dialkylamino or dialkylaminosulphonyl having in each case up to 4
carbon atoms in the alkyl groups, R.sup.4 represents nitro, cyano,
carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each
case optionally halogen-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylthio-, C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alkyl, alkoxy,
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up
to 4 carbon atoms in the alkyl groups, or represents alkylamino,
dialkylamino or dialkylaminosulphonyl having in each case up to 4
carbon atoms in the alkyl groups, and Z represents one of the
heterocyclic groupings below 767768in which the dotted bond is in
each case a single bond or a double bond, and each heterocyclic
grouping preferably only carries two substituents of the definition
R.sup.5 and/or R.sup.6, Q represents oxygen or sulphur, R.sup.5
represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents
in each case optionally cyano-, halogen-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylthio-, C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alkyl, alkylcarbonyl,
alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl
having in each case up to 6 carbon atoms in the alkyl groups,
represents in each case optionally halogen-substituted alkylamino
or dialkylamino having in each case up to 6 carbon atoms in the
alkyl groups, represents in each case optionally
halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio or
alkenylamino having in each case up to 6 carbon atoms in the
alkenyl or alkinyl groups, represents in each case optionally
halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio,
cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,
cycloalkylalkylthio or cycloalkylalkylamino having in each case 3
to 6 carbon atoms in the cycloalkyl groups and optionally up to 4
carbon atoms in the alkyl moiety, or represents in each case
optionally halogen-, C.sub.1-C.sub.4-alkyl- or
C.sub.1-C.sub.4-alkoxy-substituted phenyl, phenyloxy, phenylthio,
phenylamino, benzyl, benzyloxy, benzylthio or benzylamino,
represents pyrrolidino, piperidino or morpholino, or--if two
adjacent radicals R.sup.5 and R.sup.5 are located at a double
bond--also together with the adjacent radical R.sup.5 represents a
benzo grouping, and R.sup.6 represents hydrogen, hydroxyl, amino,
alkylidenamino having up to 4 carbon atoms, represents in each case
optionally halogen- or C.sub.1-C.sub.4-alkoxy-substituted alkyl,
alkoxy, alkylamino, dialkylamino or alkanoylamino having in each
case up to 6 carbon atoms in the alkyl groups, represents in each
case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy
having in each case up to 6 carbon atoms in the alkenyl or alkinyl
groups, represents in each case optionally halogen-substituted
cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case
3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3
carbon atoms in the alkyl moiety, or represents in each case
optionally halogen-, C.sub.1-C.sub.4-alkyl- or
C.sub.1-C.sub.4-alkoxy-sub- stituted phenyl or benzyl, or together
with an adjacent radical R.sup.5 or R.sup.6 represents optionally
halogen- or C.sub.1-C.sub.4-alkyl-substitut- ed alkanediyl having 3
to 5 carbon atoms, where the individual radicals R.sup.5 and
R.sup.6--if a plurality of them are attached to the same
heterocyclic grouping--can have identical or different meanings
within the scope of the above said definition of said radicals.
23. A compound of the Formula (II) 769in which n represents the
number 0, 1, 2 or 3, A represents alkanediyl (alkylene), R.sup.1
represents hydrogen or represents in each case optionally
substituted alkyl, alkenyl or cycloalkyl, R.sup.2 represents
hydrogen, cyano, carbamoyl, halogen, or represents in each case
optionally substituted alkyl, alkylcarbonyl, alkoxy,
alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,
R.sup.3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl,
thiocarbamoyl, halogen, or represents in each case optionally
substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,
alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
R.sup.4 represents nitro, cyano, carboxyl, carbamoyl,
thiocarbamoyl, halogen, or represents in each case optionally
substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,
alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
and X represents halogen, excluding ethyl
4-(2-bromo-methyl-benzoyl)-5-cyclopro-
pyl-isoxazole-3-carboxylate.
24. A compound of the Formula (IV) 770in which n represents the
number 0, 1, 2 or 3, A represents alkanediyl (alkylene), R.sup.1
represents hydrogen or represents in each case optionally
substituted alkyl, alkenyl or cycloalkyl, R.sup.3 represents
hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,
halogen, or represents in each case optionally substituted alkyl,
alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,
dialkylamino or dialkylaminosulphonyl, R.sup.4 represents nitro,
cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents
in each case optionally substituted alkyl, alkoxy, alkylthio,
alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or
dialkylaminosulphonyl, and Z represents an optionally substituted
4- to 12-membered, saturated or unsaturated, monocyclic or
bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms
(up to 4 nitrogen atoms and optionally--alternatively or
additionally--one oxygen atom or one sulphur atom, or one SO
grouping or one S0.sub.2 grouping) and which additionally contains
one to three oxo groups (C.dbd.O) and/or thioxo groups (C.dbd.S) as
components of the heterocycle.
Description
[0001] The invention relates to novel substituted
benzoylisoxazoles, to processes for their preparation and to their
use as herbicides.
[0002] It is already known that certain substituted
benzoylisoxazoles have herbicidal properties (cf. EP-A-418 175,
EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609
797, EP-A-609 798, EP-A-636 622, U.S. Pat. No. 5,834,402, U.S. Pat.
No. 5,863,865, WO-A-96/26192, WO-A-97/27187, WO-A-97/43270,
WO-A-99/03856). However, the activity of these compounds is not
entirely satisfactory.
[0003] This invention, accordingly, provides the novel compounds of
the general formula (I), 2
[0004] in which
[0005] n represents the number 0, 1, 2 or 3,
[0006] A represents a single bond or represents alkanediyl
(alkylene),
[0007] R.sup.1 represents hydrogen or represents in each case
optionally substituted alkyl, alkenyl or cycloalkyl,
[0008] R.sup.2 represents hydrogen, cyano, carbamoyl, halogen, or
represents in each case optionally substituted alkyl,
alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or
alkylsulphonyl,
[0009] R.sup.3 represents hydrogen, nitro, cyano, carboxyl,
carbamoyl, thiocarbamoyl, halogen, or represents in each case
optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,
alkylsulphonyl, alkylamino, dialkylamino or
dialkylaminosulphonyl,
[0010] R.sup.4 represents nitro, cyano, carboxyl, carbamoyl,
thiocarbamoyl, halogen, or represents in each case optionally
substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,
alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
and
[0011] Z represents an optionally substituted 4- to 12-membered,
saturated or unsaturated, monocyclic or bicyclic, heterocyclic
grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms
and optionally--alternatively or additionally--one oxygen atom or
one sulphur atom, or one SO grouping or one SO.sub.2 grouping) and
which additionally contains one to three oxo groups (C.dbd.O)
and/or thioxo groups (C.dbd.S) as components of the
heterocycle.
[0012] In the definitions, the hydrocarbon chains, such as alkyl or
alkanediyl--including in combination with hetero atoms, such as
alkoxy--are in each case straight-chain or branched.
[0013] n preferably represents the number 0, 1 or 2.
[0014] A preferably represents a single bond or represents
alkanediyl (alkylene) having 1 to 4 carbon atoms.
[0015] R.sup.1 preferably represents hydrogen, represents
optionally cyano-, halogen-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylthio-, C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkyl-sulphonyl-substi- tuted alkyl having 1 to 6
carbon atoms, represents optionally cyano- or halogen-substituted
alkenyl having 2 to 6 carbon atoms, or represents optionally
cyano-, halogen- or C.sub.1-C.sub.4-alkyl-substituted cycloalkyl
having 3 to 6 carbon atoms.
[0016] R.sup.2 preferably represents hydrogen, cyano, carbamoyl,
halogen, represents in each case optionally cyano-, halogen-,
C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alky, alkylcarbonyl,
alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms,
or represents in each case optionally halogen-substituted
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1
to 6 carbon atoms.
[0017] R.sup.3 preferably represents hydrogen, nitro, cyano,
carboxyl, carbamoyl, thio-carbamoyl, halogen, represents in each
case optionally halogen-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylthio-, C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alkyl, alkoxy,
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up
to 4 carbon atoms in the alkyl groups, or represents alkylamino,
dialkylamino or dialkylaminosulphonyl having in each case up to 4
carbon atoms in the alkyl groups.
[0018] R.sup.4 preferably represents nitro, cyano, carboxyl,
carbamoyl, thiocarbamoyl, halogen, represents in each case
optionally halogen-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylthio-, C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alkyl, alkoxy,
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up
to 4 carbon atoms in the alkyl groups, or represents alkylamino,
dialkylamino or dialkylaminosulphonyl having in each case up to 4
carbon atoms in the alkyl groups, and
[0019] Z preferably represents one of the heterocyclic groupings
below 34
[0020] in which the dotted bond is in each case a single bond or a
double bond, and each heterocyclic grouping preferably only carries
two substituents of the definition R.sup.5 and/or R.sup.6,
[0021] Q represents oxygen or sulphur,
[0022] R.sup.5 represents hydrogen, hydroxyl, mercapto, cyano,
halogen, represents in each case optionally cyano-, halogen-,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl- or
C.sub.1-C.sub.4-alkylsulphonyl-substit- uted alkyl, alkylcarbonyl,
alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl
having in each case up to 6 carbon atoms in the alkyl groups,
represents in each case optionally halogen-substituted alkylamino
or dialkylamino having in each case up to 6 carbon atoms in the
alkyl groups, represents in each case optionally
halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio,
alkinylthio or alkenylamino having in each case up to 6 carbon
atoms in the alkenyl or alkinyl groups, represents in each case
optionally halogen-substituted cycloalkyl, cycloalkyloxy,
cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,
cycloalkylalkylthio or cycloalkylalkylamino having in each case 3
to 6 carbon atoms in the cycloalkyl groups and optionally up to 4
carbon atoms in the alkyl moiety, or represents in each case
optionally halogen-, C.sub.1-C.sub.4-alkyl- or
C.sub.1-C.sub.4-alkoxy-substituted phenyl, phenyloxy, phenylthio,
phenylamino, benzyl, benzyloxy, benzylthio or benzylamino,
represents pyrrolidino, piperidino or morpholino, or--if two
adjacent radicals R.sup.5 and R.sup.5 are located at a double
bond--also together with the adjacent radical R.sup.5 represents a
benzo grouping, and
[0023] R.sup.6 represents hydrogen, hydroxyl, amino, alkylidenamino
having up to 4 carbon atoms, represents in each case optionally
halogen- or C.sub.1-C.sub.4-alkoxy-substituted alkyl, alkoxy,
alkylamino, dialkylamino or alkanoylamino having in each case up to
6 carbon atoms in the alkyl groups, represents in each case
optionally halogen-substituted alkenyl, alkinyl or alkenyloxy
having in each case up to 6 carbon atoms in the alkenyl or alkinyl
groups, represents in each case optionally halogen-substituted
cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case
3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3
carbon atoms in the alkyl moiety, or represents in each case
optionally halogen-, C.sub.1-C.sub.4-alkyl- or
C.sub.1-C.sub.4-alkoxy-sub- stituted phenyl or benzyl, or together
with an adjacent radical R.sup.5 or R.sup.6 represents optionally
halogen- or C.sub.1-C.sub.4-alkyl-substitut- ed alkanediyl having 3
to 5 carbon atoms,
[0024] where the individual radicals R.sup.5 and R.sup.6--if a
plurality of them are attached to the same heterocyclic
grouping--can have identical or different meanings within the scope
of the above definition.
[0025] Q preferably represents oxygen (O).
[0026] R.sup.5 preferably represents hydrogen, hydroxyl, mercapto,
cyano, fluorine, chlorine, bromine, iodine, represents in each case
optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or
i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or
i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-,
ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-,
ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl,
n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or
i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or
i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,
ethylsulphinyl, n- or i-propylsulphihyl, methylsulphonyl,
ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino,
ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,
dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino,
represents in each case optionally fluorine- and/or
chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl,
butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio,
propenylamino or butenylamino, represents in each case optionally
fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,
cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,
cyclopentylamino, cyclohexylamino, cyclopropylmethyl,
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,
cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio,
cyclopentylmethylthio, cyclohexylmethylthio,
cyclopropylmethylamino, cyclobutylmethylamino,
cyclopentylmethylamino or cyclohexylmethylamino, or represents in
each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or
i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or
i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,
benzyl, benzyloxy, benzylthio or benzylamino, represents
pyrrolidino, piperidino or morpholino, or--if two adjacent radicals
R.sup.5 and R.sup.5 are located at a double bond--together with the
adjacent radical R.sup.5 also represents a benzo grouping.
[0027] R.sup.6 preferably represents hydrogen, hydroxyl, amino,
represents in each case optionally fluorine- and/or chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-,
i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino,
ethylamino or dimethylamino, represents in each case optionally
fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl,
propinyl or propenyloxy, represents in each case optionally
fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,
cyclopentylmethyl, cyclohexylmethyl, or represents in each case
optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-,
n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or
i-propoxy-substituted phenyl or benzyl, or together with an
adjacent radical R.sup.5 or R.sup.6 represents in each case
optionally methyl- and/or ethyl-substituted propane-1,3-diyl
(trimethylene) or butane-1,4-diyl (tetramethylene).
[0028] A particularly preferably represents a single bond,
methylene, ethylidene (ethane-1,1-diyl) or dimethylene
(ethane-1,2-diyl).
[0029] R.sup.1 particularly preferably represents hydrogen,
represents in each case optionally fluorine-, chlorine-, methoxy-,
ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or
i-propylthio-, methylsulphinyl-, ethylsulphinyl, n- or
i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or
i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,
i-, s- or t-butyl, represents in each case optionally fluorine-,
chlorine- or bromine-substituted propenyl, butenyl, propinyl or
butinyl, or represents in each case optionally cyano-, fluorine-,
chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl,
cyclobutyl, cyclopentyl or cyclohexyl.
[0030] R.sup.2 particularly preferably represents hydrogen, cyano,
carbamoyl, fluorine, chlorine, bromine, represents in each case
optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl,
propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy,
methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or
represents in each case optionally fluorine- and/or
chlorine-substituted methylthio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,
methylsulphonyl or ethylsulphonyl.
[0031] R.sup.3 particularly preferably represents hydrogen, nitro,
cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,
chlorine,-bromine, iodine, represents in each case optionally
fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,
methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,
ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in
each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-,
n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy,
represents in each case optionally fluorine- and/or
chlorine-substituted methylthio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,
methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or
represents methylamino, ethylamino, n- or i-propylamino,
dimethylamino, diethylamino, dimethylaminosulphonyl or
diethylaminosulphonyl.
[0032] R.sup.4 particularly preferably represents nitro, cyano,
carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,
represents in each case optionally fluorine- and/or chlorine-,
methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or
i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-
or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,
i-, s- or t-butyl, represents in each case optionally fluorine-
and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted
methoxy, ethoxy, n- or i-propoxy, represents in each case
optionally fluorine- and/or chlorine-substituted methylthio,
ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n-
or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or
i-propylsulphonyl, or represents methylamino, ethylamino, n- or
i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl
or diethylaminosulphonyl.
[0033] Z particularly preferably represents the heterocyclic
groupings 5
[0034] R.sup.5 particularly preferably represents hydrogen,
hydroxyl, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-,
s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl,
trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl,
fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,
fluoro-n-propyl, fluoro-i-propyl, chloro-n-propyl, chloro-i-propyl,
methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy,
ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy,
chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy,
trichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy,
fluorodichloroethoxy, methylthio, ethylthio, n- or i-propylthio,
fluoroethylthio, chloroethylthio, difluoroethylthio,
dichloroethylthio, chlorofluoroethylthio, chlorodifluoroethylthio,
fluorodichloroethylthio, methylsulphinyl, ethylsulphinyl, n- or
i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or
i-propylsulphonyl, dimethylamino, propenylthio, butenylthio,
propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl,
cyclopropylmethoxy, phenyl or phenoxy.
[0035] R.sup.6 particularly preferably represents amino, methyl,
ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,
methylamino, dimethylamino, cyclopropyl or cyclopropylmethyl, or
together with R.sup.5 represents propane-1,3-diyl (trimethylene),
butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl
(pentamethylene).
[0036] A very particularly preferably represents a single bond or
represents methylene.
[0037] R.sup.1 very particularly preferably represents hydrogen,
represents in each case optionally fluorine-, chlorine-, methoxy-,
ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,
ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents
optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or
ethyl-substituted cyclopropyl.
[0038] R.sup.2 very particularly preferably represents hydrogen,
cyano, carbamoyl, fluorine, chlorine, bromine, represents in each
case optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or
t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
or represents in each case optionally fluorine- and/or
chlorine-substituted methylthio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl or
ethylsulphonyl.
[0039] R.sup.3 very particularly preferably represents hydrogen,
nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl,
trifluoromethyl, methoxymethyl, methylthiomethyl,
methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,
difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or
dimethylaminosulphonyl.
[0040] R.sup.4 very particularly preferably represents nitro,
cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
methoxymethyl, methylthiomethyl, methylsulphinylmethyl,
methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,
trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,
ethylsulphinyl, methylsulphonyl, ethylsulphonyl or
dimethylaminosulphonyl.
[0041] A most preferably represents methylene.
[0042] R.sup.1 most preferably represents cyclopropyl.
[0043] R.sup.2 most preferably represents hydrogen, methoxycarbonyl
or ethoxycarbonyl.
[0044] R.sup.3 most preferably represents chlorine, bromine, cyano,
trifluoromethyl or methylsulphonyl.
[0045] R.sup.4 most preferably represents hydrogen, cyano,
chlorine, nitro, methyl, trifluoromethyl, methoxy or
methylsulphonyl.
[0046] Preference according to the invention is given to those
compounds of the formula (I) which contain a combination of the
meanings listed above as being preferred.
[0047] Particular preference according to the invention is given to
those compounds of the formula (I) which contain a combination of
the meanings listed above as being particularly preferred.
[0048] Very particular preference according to the invention is
given to those compounds of the formula (I) which contain a
combination of the meanings listed above as being very particularly
preferred.
[0049] Most preference according to the invention is given to those
compounds of the formula (I) which contain a combination of the
meanings listed above as being most preferred.
[0050] Among the meanings given as preferred, particularly
preferred, very particularly preferred or most preferred, still
greater emphasis is given to the compounds of the general formula
(IA) 6
[0051] in which
[0052] n, A, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and
R.sup.6 are each as defined above, with very particular emphasis on
the compounds of the formula (IA) in which A represents
methylene.
[0053] Moreover, among the meanings given as being preferred,
particularly preferred, very particularly preferred or most
particularly preferred, still greater emphasis is given to the
compounds of the general formula (IB) 7
[0054] in which
[0055] n, A, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and
R.sup.6 are each as defined above.
[0056] Furthermore, among the meanings given as being preferred,
particularly preferred, very particularly preferred or most
preferred, still greater emphasis is given to those compounds of
the general formula (IC) 8
[0057] in which
[0058] n, A, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and
R.sup.6 are each as defined above.
[0059] The abovementioned general or preferred radical definitions
apply both to the end products of the formula (I) and,
correspondingly, to the starting materials or intermediates
required in each case for the preparation. These radical
definitions can be combined with one another as desired, i.e.
including combinations between the given preferred ranges.
[0060] Examples of compounds of the general formula (I) according
to the invention are listed in the groups below.
[0061] Group 1 9
[0062] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given in the table below:
1 R.sup.3 (position-) (R.sup.4).sub.n R.sup.5 R.sup.6 H -- CF.sub.3
CH.sub.3 F -- CF.sub.3 CH.sub.3 Cl -- CF.sub.3 CH.sub.3 Br --
CF.sub.3 CH.sub.3 I -- CF.sub.3 CH.sub.3 NO.sub.2 -- CF.sub.3
CH.sub.3 CN -- CF.sub.3 CH.sub.3 CH.sub.3 -- CF.sub.3 CH.sub.3
OCH.sub.3 -- CF.sub.3 CH.sub.3 CF.sub.3 -- CF.sub.3 CH.sub.3
OCHF.sub.2 -- CF.sub.3 CH.sub.3 OCF.sub.3 -- CF.sub.3 CH.sub.3
SO.sub.2CH.sub.3 -- CF.sub.3 CH.sub.3 H -- OCH.sub.3 CH.sub.3 F --
OCH.sub.3 CH.sub.3 Cl -- OCH.sub.3 CH.sub.3 Br -- OCH.sub.3
CH.sub.3 I -- OCH.sub.3 CH.sub.3 NO.sub.2 -- OCH.sub.3 CH.sub.3 CN
-- OCH.sub.3 CH.sub.3 CH.sub.3 -- OCH.sub.3 CH.sub.3 OCH.sub.3 --
OCH.sub.3 CH.sub.3 CF.sub.3 -- OCH.sub.3 CH.sub.3 OCHF.sub.2 --
OCH.sub.3 CH.sub.3 OCF.sub.3 -- OCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3
-- OCH.sub.3 CH.sub.3 H -- SCH.sub.3 CH.sub.3 F -- SCH.sub.3
CH.sub.3 Cl -- SCH.sub.3 CH.sub.3 Br -- SCH.sub.3 CH.sub.3 I --
SCH.sub.3 CH.sub.3 NO.sub.2 -- SCH.sub.3 CH.sub.3 CN -- SCH.sub.3
CH.sub.3 CH.sub.3 -- SCH.sub.3 CH.sub.3 OCH.sub.3 -- SCH.sub.3
CH.sub.3 CF.sub.3 -- SCH.sub.3 CH.sub.3 OCHF.sub.2 -- SCH.sub.3
CH.sub.3 OCF.sub.3 -- SCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 --
SCH.sub.3 CH.sub.3 H -- OC.sub.2H.sub.5 CH.sub.3 F --
OC.sub.2H.sub.5 CH.sub.3 Cl -- OC.sub.2H.sub.5 CH.sub.3 Br --
OC.sub.2H.sub.5 CH.sub.3 I -- OC.sub.2H.sub.5 CH.sub.3 NO.sub.2 --
OC.sub.2H.sub.5 CH.sub.3 CN -- OC.sub.2H.sub.5 CH.sub.3 CH.sub.3 --
OC.sub.2H.sub.5 CH.sub.3 OCH.sub.3 -- OC.sub.2H.sub.5 CH.sub.3
CF.sub.3 -- OC.sub.2H.sub.5 CH.sub.3 OCHF.sub.2 -- OC.sub.2H.sub.5
CH.sub.3 OCF.sub.3 -- OC.sub.2H.sub.5 CH.sub.3 SO.sub.2CH.sub.3 --
OC.sub.2H.sub.5 CH.sub.3 H -- N(CH.sub.3).sub.2 CH.sub.3 F --
N(CH.sub.3).sub.2 CH.sub.3 Cl -- N(CH.sub.3).sub.2 CH.sub.3 Br --
N(CH.sub.3).sub.2 CH.sub.3 I -- N(CH.sub.3).sub.2 CH.sub.3 NO.sub.2
-- N(CH.sub.3).sub.2 CH.sub.3 CN -- N(CH.sub.3).sub.2 CH.sub.3
CH.sub.3 -- N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 --
N(CH.sub.3).sub.2 CH.sub.3 CF.sub.3 -- N(CH.sub.3).sub.2 CH.sub.3
OCHF.sub.2 -- N(CH.sub.3).sub.2 CH.sub.3 OCF.sub.3 --
N(CH.sub.3).sub.2 CH.sub.3 SO.sub.2CH.sub.3 -- N(CH.sub.3).sub.2
CH.sub.3 H -- OCH.sub.3 10 F -- OCH.sub.3 11 Cl -- OCH.sub.3 12 Br
-- OCH.sub.3 13 I -- OCH.sub.3 14 NO.sub.2 -- OCH.sub.3 15 CN --
OCH.sub.3 16 CH.sub.3 -- OCH.sub.3 17 OCH.sub.3 -- OCH.sub.3 18
CF.sub.3 -- OCH.sub.3 19 OCHF.sub.2 -- OCH.sub.3 20 OCF.sub.3 --
OCH.sub.3 21 SO.sub.2CH.sub.3 -- OCH.sub.3 22 H (3-) Cl CF.sub.3
CH.sub.3 F (3-) Cl CH.sub.3 CH.sub.3 Cl (3-) Cl OCH.sub.3 CH.sub.3
Br (3-) Cl Br 23 Cl (3-) Cl CF.sub.3 Cl3 NO.sub.2 (3-) Cl CH.sub.3
CH.sub.3 Cl (3-) Cl SCH.sub.3 CH.sub.3 CH.sub.3 (3-) Cl Cl CH.sub.3
OCH.sub.3 (3-) Cl OCH.sub.3 CH.sub.3 CF.sub.3 (3-) Cl CF.sub.3
CH.sub.3 OCHF.sub.2 (3-) Cl CH.sub.3 CH.sub.3 OCF.sub.3 (3-) Cl
CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (3-) Cl OCH.sub.3 CH.sub.3
[0063] Group 2 24
[0064] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1.
[0065] Group 3 25
[0066] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1.
[0067] Group 4 26
[0068] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1, and m represents
the number 0, 1 or 2.
[0069] Group 5 27
[0070] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1.
[0071] Group 6 28
[0072] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1.
[0073] Group 7 29
[0074] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for Group 1.
[0075] Group 8 30
[0076] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given for group 1, and m represents
the number 0, 1 or 2.
[0077] Group 9 31
[0078] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 each
have, for example, the meanings given in the table below:
2 R.sup.3 (position-) (R.sup.4).sub.n R.sup.5 R.sup.6 Cl (2-) Cl
CF.sub.3 CH.sub.3 Cl (2-) Cl SCH.sub.3 CH.sub.3 Cl (2-) Cl
SC.sub.2H.sub.5 CH.sub.3 Cl (2-) Cl SC.sub.3H.sub.7 CH.sub.3 Cl
(2-) Cl SC.sub.3H.sub.7-i CH.sub.3 Cl (2-) Cl 32 CH.sub.3 Cl (2-)
Cl 33 CH.sub.3 Cl (2-) Cl 34 CH.sub.3 Cl (2-) Cl 35 CH.sub.3 Cl
(2-) Cl 36 CH.sub.3 Cl (2-) Cl SCH.dbd.C.dbd.CH.sub.2 CH.sub.3 Cl
(2-) Cl SCH.sub.2CN CH.sub.3 Cl (2-) Cl SCH.sub.2CH.sub.2CN
CH.sub.3 Cl (2-) Cl OCH.sub.3 CH.sub.3 Cl (2-) Cl OC.sub.2H.sub.5
CH.sub.3 Cl (2-) Cl OC.sub.3H.sub.7 CH.sub.3 Cl (2-) Cl
OC.sub.3H.sub.7-i CH.sub.3 Cl (2-) Cl OC.sub.4H.sub.9 CH.sub.3 Cl
(2-) Cl OCH.sub.2CF.sub.3 CH.sub.3 Cl (2-) Cl 37 CH.sub.3 Cl (2-)
Cl OC.sub.6H.sub.5 CH.sub.3 Cl (2-) Cl H CH.sub.3 Cl (2-) Cl
CH.sub.3 CH.sub.3 Cl (2-) Cl C.sub.2H.sub.5 CH.sub.3 Cl (2-) Cl
C.sub.3H.sub.7 CH.sub.3 Cl (2-) Cl C.sub.3H.sub.7-i CH.sub.3 Cl
(2-) Cl C.sub.4H.sub.9 CH.sub.3 Cl (2-) Cl C.sub.4H.sub.9-i
CH.sub.3 Cl (2-) Cl C.sub.4H.sub.9-s CH.sub.3 Cl (2-) Cl
C.sub.4H.sub.9-t CH.sub.3 Cl (2-) Cl 38 CH.sub.3 Cl (2-) Cl 39
CH.sub.3 Cl (2-) Cl CH.dbd.CHCH.sub.3 CH.sub.3 Cl (2-) Cl 40
CH.sub.3 Cl (2-) Cl 41 CH.sub.3 Cl (2-) Cl 42 CH.sub.3 Cl (2-) Cl
N(CH.sub.3).sub.2 CH.sub.3 Cl (2-) Cl 43 CH.sub.3 Cl (2-) Cl Cl
CH.sub.3 Cl (2-) Cl Br CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl CF.sub.3
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl SCH.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl SC.sub.2H.sub.5 CH.sub.3 SO.sub.2CH.sub.3
(2-) Cl SC.sub.3H.sub.7 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
SC.sub.3H.sub.7-i CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 44 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl 45 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 46
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 47 CH.sub.3 SO.sub.2CH.sub.3 (2-)
Cl 48 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl SCH.dbd.C.dbd.CH.sub.2
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl SCH.sub.2CN CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.2CH.sub.2CN CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl OCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-)
Cl OC.sub.2H.sub.5 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
OC.sub.3H.sub.7 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl OC.sub.3H.sub.7-i
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl OC.sub.4H.sub.9 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl OCH.sub.2CF.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl 49 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
OC.sub.6H.sub.5 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl H CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl CH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
C.sub.2H.sub.5 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7-i CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9 CH.sub.3 SO.sub.2CH.sub.3
(2-) Cl C.sub.4H.sub.9-i CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
C.sub.4H.sub.9-s CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-t
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 50 CH.sub.3 SO.sub.2CH.sub.3 (2-)
Cl 51 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl CH.dbd.CHCH.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl 52 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 53
CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 54 CH.sub.3 SO.sub.2CH.sub.3 (2-)
Cl N(CH.sub.3).sub.2 CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl 55 CH.sub.3
SO.sub.2CH.sub.3 (2-) Cl Cl CH.sub.3 SO.sub.2CH.sub.3 (2-) Cl Br
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
SC.sub.2H.sub.5 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 SC.sub.3H.sub.7
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 SC.sub.3H.sub.7-i CH.sub.3 Cl
(2-) SO.sub.2CH.sub.3 56 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 57
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 58 CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 59 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 60 CH.sub.3
Cl (2-) SO.sub.2CH.sub.3 SCH.dbd.C.dbd.CH.sub.2 CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 SCH.sub.2CN CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
SCH.sub.2CH.sub.2CN CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 OCH.sub.3
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 OC.sub.2H.sub.5 CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 OC.sub.3H.sub.7 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
OC.sub.3H.sub.7-i CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 OC.sub.4H.sub.9
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 OCH.sub.2CF.sub.3 CH.sub.3 Cl
(2-) SO.sub.2CH.sub.3 61 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
OC.sub.6H.sub.5 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 H CH.sub.3 Cl
(2-) SO.sub.2CH.sub.3 CH.sub.3 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
C.sub.2H.sub.5 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 C.sub.3H.sub.7
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 C.sub.3H.sub.7-i CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 C.sub.4H.sub.9 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
C.sub.4H.sub.9-i CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 C.sub.4H.sub.9-s
CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 C.sub.4H.sub.9-t CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 62 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 63 CH.sub.3
Cl (2-) SO.sub.2CH.sub.3 CH.dbd.CHCH.sub.3 CH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 64 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 65 CH.sub.3
Cl (2-) SO.sub.2CH.sub.3 66 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3
N(CH.sub.3).sub.2 CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 67 CH.sub.3 Cl
(2-) SO.sub.2CH.sub.3 Cl CH.sub.3 Cl (2-) SO.sub.2CH.sub.3 Br
CH.sub.3 Cl (2-) Cl CF.sub.3 68 Cl (2-) Cl SCH.sub.3 69 Cl (2-) Cl
SC.sub.2H.sub.5 70 Cl (2-) Cl SC.sub.3H.sub.7 71 Cl (2-) Cl
SC.sub.3H.sub.7-i 72 Cl (2-) Cl 73 74 Cl (2-) Cl 75 76 Cl (2-) Cl
77 78 Cl (2-) Cl 79 80 Cl (2-) Cl 81 82 Cl (2-) Cl
SCH.dbd.C.dbd.CH.sub.2 83 Cl (2-) Cl SCH.sub.2CN 84 Cl (2-) Cl
SCH.sub.2CH.sub.2CN 85 Cl (2-) Cl OCH.sub.3 86 Cl (2-) Cl
OC.sub.2H.sub.5 87 Cl (2-) Cl OC.sub.3H.sub.7 88 Cl (2-) Cl
OC.sub.3H.sub.7-i 89 Cl (2-) Cl OC.sub.4H.sub.9 90 Cl (2-) Cl
OCH.sub.2CF.sub.3 91 Cl (2-) Cl 92 93 Cl (2-) Cl OC.sub.6H.sub.5 94
Cl (2-) Cl H 95 Cl (2-) Cl CH.sub.3 96 Cl (2-) Cl C.sub.2H.sub.5 97
Cl (2-) Cl C.sub.3H.sub.7 98 Cl (2-) Cl C.sub.3H.sub.7-i 99 Cl (2-)
Cl C.sub.4H.sub.9 100 Cl (2-) Cl C.sub.4H.sub.9-i 101 Cl (2-) Cl
C.sub.4H.sub.9-s 102 Cl (2-) Cl C.sub.4H.sub.9-t 103 Cl (2-) Cl 104
105 Cl (2-) Cl 106 107 Cl (2-) Cl CH.dbd.CHCH.sub.3 108 Cl (2-) Cl
109 110 Cl (2-) Cl 111 112 Cl (2-) Cl 113 114 Cl (2-) Cl
N(CH.sub.3).sub.2 115 Cl (2-) Cl 116 117 Cl (2-) Cl Cl 118 Cl (2-)
Cl Br 119 SO.sub.2CH.sub.3 (2-) Cl CF.sub.3 120 SO.sub.2CH.sub.3
(2-) Cl SCH.sub.3 121 SO.sub.2CH.sub.3 (2-) Cl SC.sub.2H.sub.5 122
SO.sub.2CH.sub.3 (2-) Cl SC.sub.3H.sub.7 123 SO.sub.2CH.sub.3 (2-)
Cl SC.sub.3H.sub.7-i 124 SO.sub.2CH.sub.3 (2-) Cl 125 126
SO.sub.2CH.sub.3 (2-) Cl 127 128 SO.sub.2CH.sub.3 (2-) Cl 129 130
SO.sub.2CH.sub.3 (2-) Cl 131 132 SO.sub.2CH.sub.3 (2-) Cl 133 134
SO.sub.2CH.sub.3 (2-) Cl SCH.dbd.C.dbd.CH.sub.2 135
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.2CN 136 SO.sub.2CH.sub.3 (2-) Cl
SCH.sub.2CH.sub.2CN 137 SO.sub.2CH.sub.3 (2-) Cl OCH.sub.3 138
SO.sub.2CH.sub.3 (2-) Cl OC.sub.2H.sub.5 139 SO.sub.2CH.sub.3 (2-)
Cl OC.sub.3H.sub.7 140 SO.sub.2CH.sub.3 (2-) Cl OC.sub.3H.sub.7-i
141 SO.sub.2CH.sub.3 (2-) Cl OC.sub.4H.sub.9 142 SO.sub.2CH.sub.3
(2-) Cl OCH.sub.2CF.sub.3 143 SO.sub.2CH.sub.3 (2-) Cl 144 145
SO.sub.2CH.sub.3 (2-) Cl OC.sub.6H.sub.5 146 SO.sub.2CH.sub.3 (2-)
Cl H 147 SO.sub.2CH.sub.3 (2-) Cl CH.sub.3 148 SO.sub.2CH.sub.3
(2-) Cl C.sub.2H.sub.5 149 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7
150 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.9-i 151 SO.sub.2CH.sub.3
(2-) Cl C.sub.4H.sub.9 152 SO.sub.2CH.sub.3 (2-) Cl
C.sub.4H.sub.9-i 153 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-s 154
SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-t 155 SO.sub.2CH.sub.3 (2-)
Cl 156 157 SO.sub.2CH.sub.3 (2-) Cl 158 159 SO.sub.2CH.sub.3 (2-)
Cl CH.dbd.CHCH.sub.3 160 SO.sub.2CH.sub.3 (2-) Cl 161 162
SO.sub.2CH.sub.3 (2-) Cl 163 164 SO.sub.2CH.sub.3 (2-) Cl 165 166
SO.sub.2CH.sub.3 (2-) Cl N(CH.sub.3).sub.2 167 SO.sub.2CH.sub.3
(2-) Cl 168 169 SO.sub.2CH.sub.3 (2-) Cl Cl 170 SO.sub.2CH.sub.3
(2-) Cl Br 171 Cl (2-) SO.sub.2CH.sub.3 CF.sub.3 172 Cl (2-)
SO.sub.2CH.sub.3 SCH.sub.3 173 Cl (2-) SO.sub.2CH.sub.3
SC.sub.2H.sub.5 174 Cl (2-) SO.sub.2CH.sub.3 SC.sub.3H.sub.7 175 Cl
(2-) SO.sub.2CH.sub.3 SC.sub.3H.sub.7-i 176 Cl (2-)
SO.sub.2CH.sub.3 177 178 Cl (2-) SO.sub.2CH.sub.3 179 180 Cl (2-)
SO.sub.2CH.sub.3 181 182 Cl (2-) SO.sub.2CH.sub.3 183 184 Cl (2-)
SO.sub.2CH.sub.3 185 186 Cl (2-) SO.sub.2CH.sub.3
SCH.dbd.C.dbd.CH.sub.2 187 Cl (2-) SO.sub.2CH.sub.3 SCH.sub.2CN 188
Cl (2-) SO.sub.2CH.sub.3 SCH.sub.2CH.sub.2CN 189 Cl (2-)
SO.sub.2CH.sub.3 OCH.sub.3 190 Cl (2-) SO.sub.2CH.sub.3
OC.sub.2H.sub.5 191 Cl (2-) SO.sub.2CH.sub.3 OC.sub.3H.sub.7 192 Cl
(2-) SO.sub.2CH.sub.3 OC.sub.3H.sub.7-i 193 Cl (2-)
SO.sub.2CH.sub.3 OC.sub.4H.sub.9 194 Cl (2-) SO.sub.2CH.sub.3
OCH.sub.2CF.sub.3 195 Cl (2-) SO.sub.2CH.sub.3 196 197 Cl (2-)
SO.sub.2CH.sub.3 OC.sub.6H.sub.5 198 Cl (2-) SO.sub.2CH.sub.3 H 199
Cl (2-) SO.sub.2CH.sub.3 CH.sub.3 200 Cl (2-) SO.sub.2CH.sub.3
C.sub.2H.sub.5 201 Cl (2-) SO.sub.2CH.sub.3 C.sub.3H.sub.7 202 Cl
(2-) SO.sub.2CH.sub.3 C.sub.3H.sub.7-i 203 Cl (2-) SO.sub.2CH.sub.3
C.sub.4H.sub.9 204 Cl (2-) SO.sub.2CH.sub.3 C.sub.4H.sub.9-i 205 Cl
(2-) SO.sub.2CH.sub.3 C.sub.4H.sub.9-s 206 Cl (2-) SO.sub.2CH.sub.3
C.sub.4H.sub.9-t 207 Cl (2-) SO.sub.2CH.sub.3 208 209 Cl (2-)
SO.sub.2CH.sub.3 210 211 Cl (2-) SO.sub.2CH.sub.3 CH.dbd.CHCH.sub.3
212 Cl (2-) SO.sub.2CH.sub.3 213 214 Cl (2-) SO.sub.2CH.sub.3 215
216 Cl (2-) SO.sub.2CH.sub.3 217 218 Cl (2-) SO.sub.2CH.sub.3
N(CH.sub.3).sub.2 219 Cl (2-) SO.sub.2CH.sub.3 220 221 Cl (2-)
SO.sub.2CH.sub.3 Cl 222 Cl (2-) SO.sub.2CH.sub.3 Br 223 Cl (2-) Cl
CF.sub.3 N(CH.sub.3).sub.2 Cl (2-) Cl SCH.sub.3 N(CH.sub.3).sub.2
Cl (2-) Cl SC.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-) Cl
SC.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl (2-) Cl SC.sub.3H.sub.7-i
N(CH.sub.3).sub.2 Cl (2-) Cl 224 N(CH.sub.3).sub.2 Cl (2-) Cl 225
N(CH.sub.3).sub.2 Cl (2-) Cl 226 N(CH.sub.3).sub.2 Cl (2-) Cl 227
N(CH.sub.3).sub.2 Cl (2-) Cl 228 N(CH.sub.3).sub.2 Cl (2-) Cl
SCH.dbd.C.dbd.CH.sub.2 N(CH.sub.3).sub.2 Cl (2-) Cl SCH.sub.2CN
N(CH.sub.3).sub.2 Cl (2-) Cl SCH.sub.2CH.sub.2CN N(CH.sub.3).sub.2
Cl (2-) Cl OCH.sub.3 N(CH.sub.3).sub.2 Cl (2-) Cl OC.sub.2H.sub.5
N(CH.sub.3).sub.2 Cl (2-) Cl OC.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl
(2-) Cl OC.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-) Cl
OC.sub.4H.sub.9 N(CH.sub.3).sub.2 Cl (2-) Cl OCH.sub.2CF.sub.3
N(CH.sub.3).sub.2 Cl (2-) Cl 229 N(CH.sub.3).sub.2 Cl (2-) Cl
OC.sub.6H.sub.5 N(CH.sub.3).sub.2 Cl (2-) Cl H N(CH.sub.3).sub.2 Cl
(2-) Cl CH.sub.3 N(CH.sub.3).sub.2 Cl (2-) Cl C.sub.2H.sub.5
N(CH.sub.3).sub.2 Cl (2-) Cl C.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl
(2-) Cl C.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-) Cl
C.sub.4H.sub.9 N(CH.sub.3).sub.2 Cl (2-) Cl C.sub.4H.sub.9-i
N(CH.sub.3).sub.2 Cl (2-) Cl C.sub.4H.sub.9-s N(CH.sub.3).sub.2 Cl
(2-) Cl C.sub.4H.sub.9-t N(CH.sub.3).sub.2 Cl (2-) Cl 230
N(CH.sub.3).sub.2 Cl (2-) Cl 231 N(CH.sub.3).sub.2 Cl (2-) Cl
CH.dbd.CHCH.sub.3 N(CH.sub.3).sub.2 Cl (2-) Cl 232
N(CH.sub.3).sub.2 Cl (2-) Cl 233 N(CH.sub.3).sub.2 Cl (2-) Cl 234
N(CH.sub.3).sub.2 Cl (2-) Cl N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 Cl
(2-) Cl 235 N(CH.sub.3).sub.2 Cl (2-) Cl Cl N(CH.sub.3).sub.2 Cl
(2-) Cl Br N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl CF.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl SCH.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl SC.sub.2H.sub.5
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl SC.sub.3H.sub.7
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl SC.sub.3H.sub.7-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 236 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl 237 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3
(2-) Cl 238 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 239
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 240 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl SCH.dbd.C.dbd.CH.sub.2 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.2CN N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.2CH.sub.2CN N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OCH.sub.3 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OC.sub.2H.sub.5 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OC.sub.3H.sub.7 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OC.sub.3H.sub.7-i N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OC.sub.4H.sub.9 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl OCH.sub.2CF.sub.3 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl 241 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3
(2-) Cl OC.sub.6H.sub.5 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl
H N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl CH.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.2H.sub.5
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-s
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl C.sub.4H.sub.9-t
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 242 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl 243 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3
(2-) Cl CH.dbd.CHCH.sub.3 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
Cl 244 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 245
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl 246 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl N(CH.sub.3).sub.2 N(CH.sub.3).sub.2
SO.sub.2CH.sub.3 (2-) Cl 247 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3
(2-) Cl Cl N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) Cl Br
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 CF.sub.3
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 SCH.sub.3
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 SC.sub.2H.sub.5
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 SC.sub.3H.sub.7
N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 SC.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 248 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 249
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 250 N(CH.sub.3).sub.2 Cl
(2-) SO.sub.2CH.sub.3 251 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 252 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
SCH.dbd.C.dbd.CH.sub.2 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
SCH.sub.2CN N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
SCH.sub.2CH.sub.2CN N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OCH.sub.3 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OC.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OC.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OC.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OC.sub.4H.sub.9 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
OCH.sub.2CF.sub.3 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 253
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 OC.sub.6H.sub.5
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 H N(CH.sub.3).sub.2 Cl
(2-) SO.sub.2CH.sub.3 CH.sub.3 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.4H.sub.9 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.4H.sub.9-i N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.4H.sub.9-s N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 C.sub.4H.sub.9-t N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 254 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 255
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 CH.dbd.CHCH.sub.3
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 256 N(CH.sub.3).sub.2 Cl
(2-) SO.sub.2CH.sub.3 257 N(CH.sub.3).sub.2 Cl (2-)
SO.sub.2CH.sub.3 258 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3
N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 259
N(CH.sub.3).sub.2 Cl (2-) SO.sub.2CH.sub.3 Cl N(CH.sub.3).sub.2 Cl
(2-) SO.sub.2CH.sub.3 Br N(CH.sub.3).sub.2 Cl (2-) Cl CH.sub.3
OCH.sub.3 Cl (2-) Cl C.sub.2H.sub.5 OCH.sub.3 Cl (2-) Cl
C.sub.3H.sub.7 OCH.sub.3 Cl (2-) Cl SCH.sub.3 OCH.sub.3 Cl (2-) Cl
SC.sub.2H.sub.5 OCH.sub.3 Cl (2-) Cl OCH.sub.3 OCH.sub.3 Cl (2-) Cl
OC.sub.2H.sub.5 OCH.sub.3 Cl (2-) Cl CH.sub.3 OC.sub.2H.sub.5 Cl
(2-) Cl C.sub.2H.sub.5 OC.sub.2H.sub.5 Cl (2-) Cl C.sub.3H.sub.7
OC.sub.2H.sub.5 Cl (2-) Cl SCH.sub.3 OC.sub.2H.sub.5 Cl (2-) Cl
SC.sub.2H.sub.5 OC.sub.2H.sub.5 Cl (2-) Cl OCH.sub.3
OC.sub.2H.sub.5 Cl (2-) Cl OC.sub.2H.sub.5 OC.sub.2H.sub.5 Cl (2-)
SO.sub.2CH.sub.3 CH.sub.3 OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3
C.sub.2H.sub.5 OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3 C.sub.3H.sub.7
OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3 SCH.sub.3 OCH.sub.3 Cl (2-)
SO.sub.2CH.sub.3 SC.sub.2H.sub.5 OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3
OCH.sub.3 OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3 OC.sub.2H.sub.5
OCH.sub.3 Cl (2-) SO.sub.2CH.sub.3 CH.sub.3 OC.sub.2H.sub.5 Cl (2-)
SO.sub.2CH.sub.3 C.sub.2H.sub.5 OC.sub.2H.sub.5 Cl (2-)
SO.sub.2CH.sub.3 C.sub.3H.sub.7 OC.sub.2H.sub.5 Cl (2-)
SO.sub.2CH.sub.3 SCH.sub.3 OC.sub.2H.sub.5 Cl (2-) SO.sub.2CH.sub.3
SC.sub.2H.sub.5 OC.sub.2H.sub.5 Cl (2-) SO.sub.2CH.sub.3 OCH.sub.3
OC.sub.2H.sub.5 Cl (2-) SO.sub.2CH.sub.3 OC.sub.2H.sub.5
OC.sub.2H.sub.5 SO.sub.2CH.sub.3 (2-) Cl Cl OCH.sub.3
SO.sub.2CH.sub.3 (2-) Cl Br OCH.sub.3 SO.sub.2CH.sub.3 (2-) Cl
CH.sub.3 OCH.sub.3 SO.sub.2CH.sub.3 (2-) Cl C.sub.2H.sub.5
OCH.sub.3 SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7 OCH.sub.3
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.3 OCH.sub.3 SO.sub.2CH.sub.3 (2-)
Cl SC.sub.2H.sub.5 OCH.sub.3 SO.sub.2CH.sub.3 (2-) Cl OCH.sub.3
OC.sub.2H.sub.5 SO.sub.2CH.sub.3 (2-) Cl OC.sub.2H.sub.5
OC.sub.2H.sub.5 SO.sub.2CH.sub.3 (2-) Cl CH.sub.3 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) Cl C.sub.2H.sub.5 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) Cl C.sub.3H.sub.7 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) Cl SCH.sub.3 OC.sub.2H.sub.5 SO.sub.2CH.sub.3
(2-) Cl SC.sub.2H.sub.5 OC.sub.2H.sub.5 SO.sub.2CH.sub.3 (2-) Cl
OCH.sub.3 OC.sub.2H.sub.5 CF.sub.3 (2-) Cl Br CH.sub.3 CF.sub.3
(2-) Cl SCH.sub.3 CH.sub.3 CF.sub.3 (2-) Cl OCH.sub.3 CH.sub.3
CF.sub.3 (2-) Cl N(CH.sub.3).sub.2 CH.sub.3 CF.sub.3 (2-) Cl
CF.sub.3 CH.sub.3 CF.sub.3 (2-) NO.sub.2 Br CH.sub.3 CF.sub.3 (2-)
NO.sub.2 SCH.sub.3 CH.sub.3 CF.sub.3 (2-) NO.sub.2 OCH.sub.3
CH.sub.3 CF.sub.3 (2-) NO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CF.sub.3
(2-) NO.sub.2 CF.sub.3 CH.sub.3 CF.sub.3 (2-) CH.sub.3 Br CH.sub.3
CF.sub.3 (2-) CH.sub.3 SCH.sub.3 CH.sub.3 CF.sub.3 (2-) CH.sub.3
OCH.sub.3 CH.sub.3 CF.sub.3 (2-) CH.sub.3 N(CH.sub.3).sub.2
CH.sub.3 CF.sub.3 (2-) CH.sub.3 CF.sub.3 CH.sub.3 CF.sub.3 (2-)
OCH.sub.3 Br CH.sub.3 CF.sub.3 (2-) OCH.sub.3 SCH.sub.3 CH.sub.3
CF.sub.3 (2-) OCH.sub.3 OCH.sub.3 CH.sub.3 CF.sub.3 (2-) OCH.sub.3
N(CH.sub.3).sub.2 CH.sub.3 CF.sub.3 (2-) OCH.sub.3 CF.sub.3
CH.sub.3 SO.sub.2CH.sub.3 (2-) NO.sub.2 Br CH.sub.3
SO.sub.2CH.sub.3 (2-) NO.sub.2 SCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3
(2-) NO.sub.2 OCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) NO.sub.2
N(CH.sub.3).sub.2 CH.sub.3 SO.sub.2CH.sub.3 (2-) NO.sub.2 CF.sub.3
CH.sub.3 SO.sub.2CH.sub.3 (2-) CF.sub.3 Br CH.sub.3
SO.sub.2CH.sub.3 (2-) CF.sub.3 SCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3
(2-) CF.sub.3 OCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) CF.sub.3
N(CH.sub.3).sub.2 CH.sub.3 SO.sub.2CH.sub.3 (2-) CF.sub.3 CF.sub.3
CH.sub.3 SO.sub.2CH.sub.3 (2-) SO.sub.2CH.sub.3 Br CH.sub.3
SO.sub.2CH.sub.3 (2-) SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) SO.sub.2CH.sub.3 N(CH.sub.3).sub.2 CH.sub.3
SO.sub.2CH.sub.3 (2-) SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 CN (2-) Cl
Br CH.sub.3 CN (2-) Cl SCH.sub.3 CH.sub.3 CN (2-) Cl OCH.sub.3
CH.sub.3 CN (2-) Cl N(CH.sub.3).sub.2 CH.sub.3 CN (2-) Cl CF.sub.3
CH.sub.3 CN (2-) NO.sub.2 Br CH.sub.3 CN (2-) NO.sub.2 SCH.sub.3
CH.sub.3 CN (2-) NO.sub.2 OCH.sub.3 CH.sub.3 CN (2-) NO.sub.2
N(CH.sub.3).sub.2 CH.sub.3 CN (2-) NO.sub.2 CF.sub.3 CH.sub.3 CN
(2-) CF.sub.3 Br CH.sub.3 CN (2-) CF.sub.3 SCH.sub.3 CH.sub.3 CN
(2-) CF.sub.3 OCH.sub.3 CH.sub.3 CN (2-) CF.sub.3 N(CH.sub.3).sub.2
CH.sub.3 CN (2-) CF.sub.3 CF.sub.3 CH.sub.3 CN (2-)
SO.sub.2CH.sub.3 Br CH.sub.3 CN (2-) SO.sub.2CH.sub.3 SCH.sub.3
CH.sub.3 CN (2-) SO.sub.2CH.sub.3 OCH.sub.3 CH.sub.3 CN (2-)
SO.sub.2CH.sub.3 N(CH.sub.3).sub.2 CH.sub.3 CN (2-)
SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 Br (2-) NO.sub.2 Br CH.sub.3 Br
(2-) NO.sub.2 SCH.sub.3 CH.sub.3 Br (2-) NO.sub.2 OCH.sub.3
CH.sub.3 Br (2-) NO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 Br (2-)
NO.sub.2 CF.sub.3 CH.sub.3 Br (2-) CF.sub.3 Br CH.sub.3 Br (2-)
CF.sub.3 SCH.sub.3 CH.sub.3 Br (2-) CF.sub.3 OCH.sub.3 CH.sub.3 Br
(2-) CF.sub.3 N(CH.sub.3).sub.2 CH.sub.3 Br (2-) CF.sub.3 CF.sub.3
CH.sub.3 Br (2-) SO.sub.2CH.sub.3 Br CH.sub.3 Br (2-)
SO.sub.2CH.sub.3 SCH.sub.3 CH.sub.3 Br (2-) SO.sub.2CH.sub.3
OCH.sub.3 CH.sub.3 Br (2-) SO.sub.2CH.sub.3 N(CH.sub.3).sub.2
CH.sub.3 Br (2-) SO.sub.2CH.sub.3 CF.sub.3 CH.sub.3 Br (2-)
CH.sub.3 Br CH.sub.3 Br (2-) CH.sub.3 SCH.sub.3 CH.sub.3 Br (2-)
CH.sub.3 OCH.sub.3 CH.sub.3 Br (2-) CH.sub.3 N(CH.sub.3).sub.2
CH.sub.3 Br (2-) CH.sub.3 CF.sub.3 CH.sub.3 Cl (2-) OCH.sub.3
CF.sub.3 CH.sub.3 Cl (2-) OCH.sub.3 SCH.sub.3 CH.sub.3 Cl (2-)
OCH.sub.3 SC.sub.2H.sub.5 CH.sub.3 Cl (2-) OCH.sub.3
SC.sub.3H.sub.7 CH.sub.3 Cl (2-) OCH.sub.3 SC.sub.3H.sub.7-i
CH.sub.3 Cl (2-) OCH.sub.3 260 CH.sub.3 Cl (2-) OCH.sub.3 261
CH.sub.3 Cl (2-) OCH.sub.3 262 CH.sub.3 Cl (2-) OCH.sub.3 263
CH.sub.3 Cl (2-) OCH.sub.3 264 CH.sub.3 Cl (2-) OCH.sub.3
SCH.dbd.C.dbd.CH.sub.2 CH.sub.3 Cl (2-) OCH.sub.3 SCH.sub.2CN
CH.sub.3 Cl (2-) OCH.sub.3 SCH.sub.2CH.sub.2CN CH.sub.3 Cl (2-)
OCH.sub.3 OCH.sub.3 CH.sub.3 Cl (2-) OCH.sub.3 OC.sub.2H.sub.5
CH.sub.3 Cl (2-) OCH.sub.3 OC.sub.3H.sub.7 CH.sub.3 Cl (2-)
OCH.sub.3 OC.sub.3H.sub.7-i CH.sub.3 Cl (2-) OCH.sub.3
OC.sub.4H.sub.9 CH.sub.3 Cl (2-) OCH.sub.3 OCH.sub.2CF.sub.3
CH.sub.3 Cl (2-) OCH.sub.3 265 CH.sub.3 Cl (2-) OCH.sub.3
OC.sub.6H.sub.5 CH.sub.3 Cl (2-) OCH.sub.3 H CH.sub.3 Cl (2-)
OCH.sub.3 CH.sub.3 CH.sub.3 Cl (2-) OCH.sub.3 C.sub.2H.sub.5
CH.sub.3 Cl (2-) OCH.sub.3 C.sub.3H.sub.7 CH.sub.3 Cl (2-)
OCH.sub.3 C.sub.3H.sub.7-i CH.sub.3 Cl (2-) OCH.sub.3
C.sub.4H.sub.9 CH.sub.3 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-i CH.sub.3
Cl (2-) OCH.sub.3 C.sub.4H.sub.9-s CH.sub.3 Cl (2-) OCH.sub.3
C.sub.4H.sub.9-t CH.sub.3 Cl (2-) OCH.sub.3 266 CH.sub.3 Cl (2-)
OCH.sub.3 267 CH.sub.3 Cl (2-) OCH.sub.3 CH.dbd.CHCH.sub.3 CH.sub.3
Cl (2-) OCH.sub.3 268 CH.sub.3 Cl (2-) OCH.sub.3 269 CH.sub.3 Cl
(2-) OCH.sub.3 270 CH.sub.3 Cl (2-) OCH.sub.3 N(CH.sub.3).sub.2
CH.sub.3 Cl (2-) OCH.sub.3 271 CH.sub.3 Cl (2-) OCH.sub.3 Cl
CH.sub.3 Cl (2-) OCH.sub.3 Br CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 CF.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.2H.sub.5
CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.3H.sub.7 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.3H.sub.7-i CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 272 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 273 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 274 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 275 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 276 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.dbd.C.dbd.CH.sub.2 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.sub.2CN CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.sub.2CH.sub.2CN CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
OCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.2H.sub.5
CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.3H.sub.7 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.3H.sub.7-i CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.4H.sub.9 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OCH.sub.2CF.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 277 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.6H.sub.5 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
H CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.sub.3 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.2H.sub.5 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7-i CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-i CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-s CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-t CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 278 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 279 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
CH.dbd.CHCH.sub.3 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 280
CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 281 CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 282 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 N(CH.sub.3).sub.2 CH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 283 CH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 Cl CH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 Br CH.sub.3 Cl (2-) OCH.sub.3
CF.sub.3 284 Cl (2-) OCH.sub.3 SCH.sub.3 285 Cl (2-) OCH.sub.3
SC.sub.2H.sub.5 286 Cl (2-) OCH.sub.3 SC.sub.3H.sub.7 287 Cl (2-)
OCH.sub.3 SC.sub.3H.sub.7-i 288 Cl (2-) OCH.sub.3 289 290 Cl (2-)
OCH.sub.3 291 292 Cl (2-) OCH.sub.3 293 294 Cl (2-) OCH.sub.3 295
296 Cl (2-) OCH.sub.3 297 298 Cl (2-) OCH.sub.3
SCH.dbd.C.dbd.CH.sub.2 299 Cl (2-) OCH.sub.3 SCH.sub.2CN 300 Cl
(2-) OCH.sub.3 SCH.sub.2CH.sub.2CN 301 Cl (2-) OCH.sub.3 OCH.sub.3
302 Cl (2-) OCH.sub.3 OC.sub.2H.sub.5 303 Cl (2-) OCH.sub.3
OC.sub.3H.sub.7 304 Cl (2-) OCH.sub.3 OC.sub.3H.sub.7-i 305 Cl (2-)
OCH.sub.3 OC.sub.4H.sub.9 306 Cl (2-) OCH.sub.3 OCH.sub.2CF.sub.3
307 Cl (2-) OCH.sub.3 308 309 Cl (2-) OCH.sub.3 OC.sub.6H.sub.5 310
Cl (2-) OCH.sub.3 H 311 Cl (2-) OCH.sub.3 CH.sub.3 312 Cl (2-)
OCH.sub.3 C.sub.2H.sub.5 313 Cl (2-) OCH.sub.3 C.sub.3H.sub.7 314
Cl (2-) OCH.sub.3 C.sub.3H.sub.7-i 315 Cl (2-) OCH.sub.3
C.sub.4H.sub.9 316 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-i 317 Cl (2-)
OCH.sub.3 C.sub.4H.sub.9-s 318 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-t
319 Cl (2-) OCH.sub.3 320 321 Cl (2-) OCH.sub.3 322 323 Cl (2-)
OCH.sub.3 CH.dbd.CHCH.sub.3 324 Cl (2-) OCH.sub.3 325 326 Cl (2-)
OCH.sub.3 327 328 Cl (2-) OCH.sub.3 329 330 Cl (2-) OCH.sub.3
N(CH.sub.3).sub.2 331 Cl (2-) OCH.sub.3 332 333 Cl (2-) OCH.sub.3
Cl 334 Cl (2-) OCH.sub.3 Br 335 SO.sub.2CH.sub.3 (2-) OCH.sub.3
CF.sub.3 336 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SCH.sub.3 337
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.2H.sub.5 338
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC3H.sub.7 339 SO.sub.2CH.sub.3
(2-) OCH.sub.3 SC.sub.3H.sub.7-i 340 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 341 342 SO.sub.2CH.sub.3 (2-) OCH.sub.3 343 344
SO.sub.2CH.sub.3 (2-) OCH.sub.3 345 346 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 347 348 SO.sub.2CH.sub.3 (2-) OCH.sub.3 349 350
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SCH.dbd.C.dbd.CH.sub.2 351
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SCH.sub.2CN 352 SO.sub.2CH.sub.3
(2-) OCH.sub.3 SCH.sub.2CH.sub.2CN 353 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OCH.sub.3 354 SO.sub.2CH.sub.3 (2-) OCH.sub.3
OC.sub.2H.sub.5 355 SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.3H.sub.7
356 SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.3H.sub.7-i 357
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.4H.sub.9 358
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OCH.sub.2CF.sub.3 359
SO.sub.2CH.sub.3 (2-) OCH.sub.3 360 361 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.6H.sub.5 362 SO.sub.2CH.sub.3 (2-) OCH.sub.3 H 363
SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.sub.3 364 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 C.sub.2H.sub.5 365 SO.sub.2CH.sub.3 (2-) OCH.sub.3
C.sub.3H.sub.7 366 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7-i
367 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9 368
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-i 369
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-s 370
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-t 371
SO.sub.2CH.sub.3 (2-) OCH.sub.3 372 373 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 374 375 SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.dbd.CHCH.sub.3
376 SO.sub.2CH.sub.3 (2-) OCH.sub.3 377 378 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 379 380 SO.sub.2CH.sub.3 (2-) OCH.sub.3 381 382
SO.sub.2CH.sub.3 (2-) OCH.sub.3 N(CH.sub.3).sub.2 383
SO.sub.2CH.sub.3 (2-) OCH.sub.3 384 385 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 Cl 386 SO.sub.2CH.sub.3 (2-) OCH.sub.3 Br 387 Cl (2-)
OCH.sub.3 CF.sub.3 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 SCH.sub.3
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
SC.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 SC.sub.3H.sub.7
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 SC.sub.3H.sub.7-i
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 388 N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 389 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 390
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 391 N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 392 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
SCH.dbd.C.dbd.CH.sub.2 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
SCH.sub.2CN N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 SCH.sub.2CH.sub.2CN
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 Cl
(2-) OCH.sub.3 OC.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
OC.sub.3H.sub.7 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
OC.sub.3H.sub.7-i N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
OC.sub.4H.sub.9 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
OCH.sub.2CF.sub.3 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 393
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 OC.sub.6H.sub.5
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 H N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 CH.sub.3 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3
C.sub.2H.sub.5 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.3H.sub.7
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.3H.sub.7-i
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.4H.sub.9
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-i
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-s
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 C.sub.4H.sub.9-t
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 394 N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 395 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 CH.dbd.CHCH.sub.3
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 396 N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 397 N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 398
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 N(CH.sub.3).sub.2
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 399 N(CH.sub.3).sub.2 Cl (2-)
OCH.sub.3 Cl N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 Br
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 CF.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SCH.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.2H.sub.5
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.3H.sub.7
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.3H.sub.7-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 400
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 401
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 402
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 403
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 404
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.dbd.C.dbd.CH.sub.2 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 SCH.sub.2CN N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 SCH.sub.2CH.sub.2CN N(CH.sub.3).sub.2 SO.sub.2CH.sub.3
(2-) OCH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.2H.sub.5 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.3H.sub.7 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.3H.sub.7-i N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OC.sub.4H.sub.9 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 OCH.sub.2CF.sub.3 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 405 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3
OC.sub.6H.sub.5 N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 H
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.2H.sub.5
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-i
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-s
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.4H.sub.9-t
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 406
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 407
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.dbd.CHCH.sub.3
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 408
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 409
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 410
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 N(CH.sub.3).sub.2
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 411
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 Cl
N(CH.sub.3).sub.2 SO.sub.2CH.sub.3 (2-) OCH.sub.3 Br
N(CH.sub.3).sub.2 Cl (2-) OCH.sub.3 CH.sub.3 OCH.sub.3 Cl (2-)
OCH.sub.3 C.sub.2H.sub.5 OCH.sub.3 Cl (2-) OCH.sub.3 C.sub.3H.sub.7
OCH.sub.3 Cl (2-) OCH.sub.3 SCH.sub.3 OCH.sub.3 Cl (2-) OCH.sub.3
SC.sub.2H.sub.5 OCH.sub.3 Cl (2-) OCH.sub.3 OCH.sub.3 OCH.sub.3 Cl
(2-) OCH.sub.3 OC.sub.2H.sub.5 OCH.sub.3 Cl (2-) OCH.sub.3 CH.sub.3
OC.sub.2H.sub.5 Cl (2-) OCH.sub.3 C.sub.2H.sub.5 OC.sub.2H.sub.5 Cl
(2-) OCH.sub.3 C.sub.3H.sub.7 OC.sub.2H.sub.5 Cl (2-) OCH.sub.3
SCH.sub.3 OC.sub.2H.sub.5 Cl (2-) OCH.sub.3 SC.sub.2H.sub.5
OC.sub.2H.sub.5 Cl (2-) OCH.sub.3 OCH.sub.3 OC.sub.2H.sub.5 Cl (2-)
OCH.sub.3 OC.sub.2H.sub.5 OC.sub.2H.sub.5 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 Cl OCH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 Br OCH.sub.3
SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.sub.3 OCH.sub.3 SO.sub.2CH.sub.3
(2-) OCH.sub.3 C.sub.2H.sub.5 OCH.sub.3 SO.sub.2CH.sub.3 (2-)
OCH.sub.3 C.sub.3H.sub.7 OCH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3
SCH.sub.3 OCH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.2H.sub.5
OCH.sub.3 SO.sub.2CH.sub.3 (2-) OCH.sub.3 OCH.sub.3 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OC.sub.2H.sub.5 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 CH.sub.3 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.2H.sub.5 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 C.sub.3H.sub.7 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SCH.sub.3 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 SC.sub.2H.sub.5 OC.sub.2H.sub.5
SO.sub.2CH.sub.3 (2-) OCH.sub.3 OCH.sub.3 OC.sub.2H.sub.5
[0079] Group 10 412
[0080] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9.
[0081] Group 11 413
[0082] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9.
[0083] Group 12 414
[0084] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9, and m represents the
number 0, 1 or 2.
[0085] Group 13 415
[0086] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9.
[0087] Group 14 416
[0088] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9.
[0089] Group 15 417
[0090] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9.
[0091] Group 16 418
[0092] Here, R.sup.3, (R.sup.4).sub.n, R.sup.5 and R.sup.6 have,
for example, the meanings given for Group 9, and m represents the
number 0, 1 or 2.
[0093] The novel substituted benzoylisoxazoles of the general
formula (I) have strong and selective herbicidal activity.
[0094] The novel substituted benzoylisoxazoles of the general
formula (I) are obtained when
[0095] (a) benzoylisoxazoles of the general formula (II) 419
[0096] in which
[0097] n, A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as
defined above and
[0098] X represents halogen
[0099] are reacted with heterocycles of the general formula
(III)
H-Z (III)
[0100] in which
[0101] Z is as defined above,
[0102] if appropriate in the presence of one or more reaction
auxiliaries and if appropriate in the presence of one or more
diluents,
[0103] or when
[0104] if R.sup.2 is hydrogen
[0105] (b) benzoyl ketones of the general formula (IV) 420
[0106] in which
[0107] n, A, R.sup.1, R.sup.3, R.sup.4 and Z are each as defined
above
[0108] are reacted with a trialkyl orthoformate or an
N,N-dimethylformamide dialkyl acetal and subsequently with
hydroxylamine or an acid adduct thereof,
[0109] if appropriate in the presence of one or more reaction
auxiliaries and if appropriate in the presence of one or more
diluents,
[0110] or when
[0111] if R.sup.2 represents optionally substituted
alkoxycarbonyl
[0112] (c) benzoyl ketones of the general formula (IV) 421
[0113] in which
[0114] n, A, R.sup.1, R.sup.3, R.sup.4 and Z are each as defined
above are reacted with an alkyl cyanoformate and then with
hydroxylamine or an acid adduct thereof, or with an alkyl
chloro-hydroximino-acetate, if appropriate in the presence of one
or more reaction auxiliaries and if appropriate in the presence of
one or more diluents,
[0115] or when
[0116] if R.sup.2 represents alkylthio
[0117] (d) benzoyl ketones of the general formula (IV) 422
[0118] in which
[0119] n, A, R.sup.1, R.sup.3, R.sup.4 and Z are each as defined
above
[0120] are reacted with carbon disulphide and with an alkylating
agent and then with hydroxylamine or an acid adduct thereof,
[0121] if appropriate in the presence of one or more reaction
auxiliaries and if appropriate in the presence of one or more
diluents,
[0122] and electrophilic or nucleophilic substitutions and/or
oxidations or reductions within the scope of the definition of the
substituents are, if appropriate, subsequently carried out in a
customary manner on the compounds of the formula (I) obtained
according to processes (a) to (d).
[0123] The compounds of the formula (I) can be converted by
customary methods into other compounds of the formula (I) according
to the above definition, for example by nucleophilic substitution
(for example R.sup.5:Cl.fwdarw.OC.sub.2H.sub.5, SCH.sub.3) or by
oxidation (for example
R.sup.5:CH.sub.2SCH.sub.3.fwdarw.CH.sub.2S(O)CH.sub.3).
[0124] In the preparation of compounds of the general formula (I),
it is also possible that compounds of the general formula (IE)
423
[0125] in which
[0126] n, A, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Z are each as
defined above
[0127] are formed in certain amounts.
[0128] The compounds of the general formula (IE) also form, as
novel substances, part of the subject-matter of the present
application.
[0129] Using, for example,
(3-chloromethyl-4-trifluoromethyl-phenyl)-(3,5--
dimethyl-iso-xazol-4-yl)-methanone and
4-methyl-5-trifluoromethyl-2,4-dihy- dro-3H-1,2,4-triazol-3-one as
starting materials, the course of the reaction in the process (a)
according to the invention can be illustrated by the following
formula scheme: 424
[0130] Using, for example,
1-[2-chloro-3-(3,4-dimethyl-5-oxo-4,5-dihydro-[-
1,2,4-triazol-1-yl-methyl)-phenyl]-pentane-1,3-dione,
N,N-dimethyl-formamide diethyl acetal and hydroxylamine as starting
materials, the course of the reaction in the process (b) according
to the invention can be illustrated by the following formula
scheme: 425
[0131] Using, for example,
1-[2-chloro-3-(4-ethoxy-3-ethyl-5-oxo-4,5-dihyd-
ro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane1,3-dione,
ethyl cyanoformate and hydroxylamine as starting materials, the
course of the reaction in the process (c) according to the
invention can be illustrated by the following formula scheme:
426
[0132] Using, for example,
1-[2-chloro-3-(4-methyl-3-methylthio-5-oxo-4,5--
dihydro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane-1,3-dione-
, carbon disulphide, methyl bromide and hydroxylamine as starting
materials, the course of the reaction in the process (d) according
to the invention can be illustrated by the following formula
scheme: 427
[0133] The formula (II) provides a general definition of the
benzoylisoxazoles to be used as starting materials in the process
(a) according to the invention for preparing compounds of the
general formula (I). In the general formula (II), n, A, R.sup.1,
R.sup.2, R.sup.3 and R.sup.4 each preferably have those meanings
which have already been mentioned above, in connection with the
description of the compounds of the general formula (I) according
to the invention, as being preferred, particularly preferred, very
particularly preferred or most preferred for n, A, R.sup.1,
R.sup.2, R.sup.3 and R.sup.4; X preferably represents fluorine,
chlorine, bromine or iodine, in particular chlorine or bromine.
[0134] Except for ethyl
4-(2-bromo-methyl-benzoyl)-5-cyclopropyl-isoxazole- -3-carboxylate
(cf WO-A-95/31446), the starting materials of the general formula
(II) have hitherto not been disclosed in the literature; except for
ethyl
4-(2-bromomethyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate- ,
they also form, as novel substances, part of the subject-matter of
the present application.
[0135] The novel benzoylisoxazoles of the general formula (II) are
obtained when benzoylisoxazoles of the general formula (V) 428
[0136] in which
[0137] n, A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as
defined above
[0138] are reacted with a side-chain halogenating agent, such as,
for example, N-bromo-succinimide or N-chloro-succinimide, under UV
light or in the presence of a reaction auxiliary, such as, for
example, 2,2'-azo-bis-isobutyonitrile, in the presence of a
diluent, such as, for example, carbon tetrachloride, at
temperatures between 0.degree. C. and 100.degree. C. (cf.
WO-A-95/31446; Preparation Examples).
[0139] The intermediates of the general formula (V) are known
and/or can be prepared by processes known per se (cf.
WO-A-95/31446; Preparation Examples).
[0140] The formula (III) provides a general definition of the
heterocycles further to be used as starting materials in the
process (a) according to the invention for preparing compounds of
the general formula (I). In the general formula (III), Z preferably
has that meaning which has already been mentioned above, in
connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred for
Z.
[0141] The starting materials of the general formula (III) are
known and/or can be prepared by processes known per se.
[0142] The formula (IV) provides a general defintion of the benzoyl
ketones to be used as starting materials in the processes (b), (c)
and (d) according to the invention for preparing compounds of the
general formula (I). In the general formula (IV), n, A, R.sup.1,
R.sup.3, R.sup.4 and Z each preferably have those meanings which
have already been mentioned above, in connection with the
description of the compounds of the general formula (I) according
to the invention, as being preferred, particularly preferred, very
particularly preferred or most preferred for n, A, R.sup.1,
R.sup.3, R.sup.4 and Z.
[0143] The starting materials of the general formula (IV) have
hitherto not been disclosed in the literature; they also, as novel
substances, form part of the subject-matter of the present
application.
[0144] The novel benzoyl ketones of the general formula (IV) are
obtained when ketones of the general formula (VI) 429
[0145] in which
[0146] R.sup.1 is as defined above,
[0147] are reacted with benzoic acid derivatives of the general
formula (VII) 430
[0148] in which
[0149] n, A, R.sup.3, R.sup.4 and Z are each as defined above,
and
[0150] Y represents halogen (in particular fluorine, chlorine or
bromine) or represents optionally substituted alkoxy (in particular
methoxy, ethoxy or ethoxyethoxy),
[0151] if appropriate in the presence of a reaction auxiliary, such
as, for example, sodium hydride, and if appropriate in the presence
of a diluent, such as, for example, tetra-hydrofuran, at
temperatures between 0.degree. C. and 100.degree. C. (cf. the
Preparation Examples).
[0152] The benzoic acid derivatives of the general formula (VII)
required as intermediates are known and/or can be prepared by
processes known per se (cf. DE-A-38 39 480, DE-A-42 39 296,
EP-A-597 360, EP-A-609 734, DE-A-43 03 676, EP-A-617 026, DE-A-44
05 614, U.S. Pat. No. 5,378,681).
[0153] The benzoic acid derivatives of the general formula (VII)
are obtained when halogeno(alkyl)benzoic acid derivatives of the
general formula (VIII) 431
[0154] in which
[0155] n, A, R.sup.3 and R.sup.4 are each as defined above and
[0156] X represents halogen (in particular fluorine, chlorine or
bromine) and
[0157] Y.sup.1 represents optionally substituted alkoxy (in
particular methoxy, ethoxy or ethoxyethoxy),
[0158] are reacted with compounds of the general formula (III),
H-Z (III)
[0159] in which
[0160] Z is as defined above,
[0161] if appropriate in the presence of a reaction auxiliary, such
as, for example, sodium hydride, triethylamine or potassium
carbonate, and if appropriate in the presence of a diluent, such
as, for example, acetone, acetonitrile, N,N-dimethylformamide or
N,N-dimethyl-acetamide, at temperatures between 50.degree. C. and
200.degree. C. (cf. the Preparation Examples).
[0162] The halogeno(alkyl)benzoic acid derivatives of the formula
(VIII) required as intermediates are known and/or can be prepared
by processes known per se (cf. EP-A-90 369, EP-A-93 488, EP-A-399
732, EP-A-480 641, EP-A-609 798, EP-A-763 524, DE-A-21 26 720,
WO-A-93/03722, WO-A-97/38977, U.S. Pat. No. 3,978,127, U.S. Pat.
No. 4,837,333).
[0163] The process (b) according to the invention for preparing the
compounds of the formula (I) is carried out using orthoformic
esters or N,N-dimethylformamide acetals. These compounds preferably
contain alkyl groups having 1 to 4 carbon atoms, in particular
methyl or ethyl. Examples which may be mentioned are trimethyl
orthoformate, triethyl orthoformate, N,N-dimethyl-formamide
dimethyl acetal and N,N-dimethyl-formamide diethyl acetal.
[0164] The process (c) according to the invention for preparing the
compounds of the formula (I) is carried out using alkyl
cyanoformates or alkyl chloro-hydroximino-acetates. These compounds
preferably contain alkyl groups having 1 to 4 carbon atoms, in
particular methyl or ethyl. Examples which may be mentioned are
methyl cyanoformate, ethyl cyanoformate, methyl
chloro-hydroximino-acetate and ethyl
chloro-hydroximino-acetate.
[0165] The process (d) according to the invention for preparing the
compounds of the formula (I) is carried out using (carbon
disulphide and) alkylating agents. These compounds preferably
contain alkyl groups having 1 to 4 carbon atoms, in particular
methyl or ethyl. Examples which may be mentioned are methyl
chloride, methyl bromide, methyl iodide, dimethyl sulphate, ethyl
chloride, ethyl bromide, ethyl iodine and diethyl sulphate.
[0166] The processes (b), (c) and--if appropriate--(d) according to
the invention for preparing the compounds of the formula (I) are
carried out using hydroxylamine or an acid adduct thereof. A
preferred acid adduct which may be mentioned is hydroxylamine
hydrochloride.
[0167] The processes according to the invention for preparing the
compounds of the general formula (I) are preferably carried out
using diluents. Suitable diluents for carrying out the processes
(a), (b), (c) and (d) according to the invention are, in addition
to water, especially inert organic solvents. These include, in
particular, aliphatic, alicyclic or aromatic, optionally
halogenated hydrocarbons, such as, for example, benzine, benzene,
toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,
hexane, cyclohexane, dichloromethane, chloroform, carbon
tetrachloride; ethers, such as diethyl ether, diisopropyl ether,
dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or
ethylene glycol diethyl ether; ketones, such as acetone, butanone
or methyl isobutyl ketone; nitriles, such as acetonitrile,
propionitrile or butyronitrile; amides, such as
N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide,
N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such
as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl
sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol,
ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,
diethylene glycol monomethyl ether, diethylene glycol monoethyl
ether, mixtures thereof with water or pure water.
[0168] Suitable reaction auxiliaries for the processes (a), (b),
(c) and (d) according to the invention are, in general, the
customary inorganic or organic bases or acid acceptors. These
preferably include alkali metal or alkaline earth metal acetates,
amides, carbonates, bicarbonates, hydrides, hydroxides or
alkoxides, such as, for example, sodium acetate, potassium acetate
or calcium acetate, lithium amide, sodium amide, potassium amide or
calcium amide, sodium carbonate, potassium carbonate or calcium
carbonate, sodium bicarbonate, potassium bicarbonate or calcium
bicarbonate, lithium hydride, sodium hyride, potassium hydride or
calcium hydride, lithium hydroxide, sodium hydroxide, potassium
hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or
i-propoxide, n-, i-, s- or -t-butoxide or potassium methoxide,
ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore
also basic organic nitrogen compounds, such as, for example,
trimethylamine, triethylamine, tripropylamine tributylaamine
ethyl-diisopropylamine N,N-dimethyl-cyclohexylamine,
dicyclohexylamine ethyl-dicyclohexylamine, N,N-dimethylaniline,
N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-,
4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and
3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine,
4-di-methylamino-pyridin- e, N-methylpiperidine,
1,4-diazabicyclo[2.2.2]-octane (DABCO),
1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or
1,8-diazabicyclo[5.4.0]-undec- -7-ene (DBU).
[0169] When carrying out the processes (a), (b), (c) and (d)
according to the invention, the reaction temperatures can be varied
within a relatively wide range. In general, the processes are
carried out at temperatures between 0.degree. C. and 150.degree.
C., preferably between 10.degree. C. and 120.degree. C.
[0170] The processes according to the invention are generally
carried out under atmospheric pressure. However, it is also
possible to carry out the processes according to the invention
under elevated or reduced pressure--in general between 0.1 bar and
10 bar.
[0171] For carrying out the processes according to the invention,
the starting materials are generally employed in approximately
equimolar amounts. However, it is also possible for one of the
components to be used in a relatively large excess. The reaction is
generally carried out in a suitable diluent in the presence of a
reaction auxiliary, and the reaction mixture is generally stirred
at the required temperature for several hours. Work-up is carried
out by customary methods (cf. the Preparation Examples).
[0172] The active compounds according to the invention can be used
as defoliants, desiccants, haulm killers and, especially, as weed
killers. By weeds in the broadest sense there are to be understood
all plants which grow in locations where they are undesired.
Whether the substances according to the invention act as total or
selective herbicides depends essentially on the amount used.
[0173] The active compounds according to the invention can be used,
for example, in connection with the following plants:
[0174] Dicotyledonous weeds of the genera: Sinapis, Lepidium,
Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium,
Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus,
Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus,
Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon,
Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Taraxacum.
[0175] Dicotyledonous crops of the genera: Gossypium, Glycine,
Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoca, Vicia,
Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis,
Cucurbita.
[0176] Monocotyledonous weeds of the genera: Echinochloa, Setaria,
Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria,
Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon,
Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus,
Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis,
Alopecurus, Apera.
[0177] Monocotyledonous crops of the genera: Oryza, Zea, Triticum,
Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas,
Asparagus, Allium.
[0178] However, the use of the active compounds according to the
invention is in no way restricted to these genera, but also extends
in the same manner to other plants.
[0179] Depending on the concentration, the compounds according to
the invention are suitable for total weed control, for example on
industrial terrain and rail tracks and on paths and areas with or
without tree growth. Equally, the compounds according to the
invention can be employed for controlling weeds in perennial crops,
for example forests, ornamental tree plantings, orchards,
vineyards, citrus groves, nut orchards, banana plantations, coffee
plantations, tea plantations, rubber plantations, oil palm
plantations, cocoa plantations, soft fruit plantings and hop
fields, on lawns and turf and pastures and for selective weed
control in annual crops.
[0180] The compounds of the formula (I) according to the invention
have strong herbicidal activity and a broad activity spectrum when
used on the soil and on above-ground parts of plants. To a certain
extent they are also suitable for selective control of
monocotyledonous and dicotyledonous weeds in monocotyledonous and
dicotyledonous crops, both by the pre-emergence and by the
post-emergence method.
[0181] The active compounds can be converted into the customary
formulations, such as solutions, emulsions, wettable powders,
suspensions, powders, dusts, pastes, soluble powders, granules,
suspo-emulsion concentrates, natural and synthetic substances
impregnated with active compound, and microencapsulations in
polymeric substances.
[0182] These formulations are produced in a known manner, for
example by mixing the active compounds with extenders, that is to
say liquid solvents and/or solid carriers, optionally with the use
of surfactants, that is to say emulsifiers and/or dispersants
and/or foam formers.
[0183] If the extender used is water, it is also possible to use,
for example, organic solvents as auxiliary solvents. Liquid
solvents which are mainly suitable are: aromatics, such as xylene,
toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated
aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or
methylene chloride, aliphatic hydrocarbons, such as cyclohexane or
paraffins, for example petroleum fractions, mineral and vegetable
oils, alcohols, such as butanol or glycol, and also their ethers
and esters, ketones, such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents, such as
dimethyl-formamide and dimethyl sulphoxide, and water.
[0184] Suitable solid carriers are: for example ammonium salts and
ground natural minerals, such as kaolins, clays, talc, chalk,
quartz, attapulgite, montmorillonite or diatomaceous earth, and
ground synthetic minerals, such as finely divided silica, alumina
and silicates; suitable solid carriers for granules are: for
example crushed and fractionated natural rocks, such as calcite,
marble, pumice, sepiolite, dolomite and synthetic granules of
inorganic and organic meals, and granules of organic material, such
as sawdust, coconut shells, maize cobs and tobacco stalks; suitable
emulsifiers and/or foam formers are: for example nonionic and
anionic emulsifiers, such as polyoxyethylene fatty acid esters,
polyoxyethylene fatty alcohol ethers, for example alkylaryl
polyglycol ethers, alkylsulphonates, alkyl sulphates,
aryl-sulphonates and protein hydrolysates; suitable dispersants
are: for example lignosulphite waste liquors and
methylcellulose.
[0185] Tackifiers, such as carboxymethylcellulose, natural and
synthetic polymers in the form of powders, granules or latices,
such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and
also natural phospholipids, such as cephalins and lecithins, and
synthetic phospholipids can be used in the formulations. Other
possible additives are mineral and vegetable oils.
[0186] It is possible to use dyestuffs, such as inorganic pigments,
for example iron oxide, titanium oxide, Prussian blue, and organic
dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal
phthalocyanine dyestuffs, and trace nutrients, such as salts of
iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0187] The formulations generally comprise between 0.1 and 95 per
cent by weight of active compound, preferably between 0.5 and
90%.
[0188] For controlling weeds, the active compounds according to the
invention, as such or in the form of their formulations, can also
be used as mixtures with known herbicides, finished formulations or
tank mixes being possible.
[0189] Possible components for the mixtures are known herbicides,
for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor,
alloxydim(-sodium), ametryne, amicarbazone, amidochlor,
amidosulfuron, anilofos, asulam, atrazine, azafenidin,
azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl),
bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl),
bialaphos, bifenox, bispyribac-(-sodium), bromobutide,
bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,
cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),
chlomethoxy-fen, chloramben, chloridazon, chlorimuron(-ethyl),
chlornitrofen, chlorosulfuron, chlorotoluron, cinidon(-ethyl),
cinmethylin, cinosulfuron, clethodim, clodinafop-(-propargyl),
clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl),
cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate,
cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB,
2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl),
diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican,
diflufenzopyr, dimefuron, dimepiperate, dimethachlor,
dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid,
diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb,
ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,
ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl),
flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),
flazasulffiron, fluazifop(-P-butyl), fluazolate, flucarbazone,
flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin,
flumipropyn, flumetsulam, fluometuron, fluorochloridone,
fluoroglycofen(-ethyl), flupoxam, flupropacil,
flurpyrsulfuron-(-methyl, -sodium), flurenol(-butyl), fluridone,
fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl),
fluthiamide, fomesafen, glufosinate(-animonium),
glyphosate(-isopropylamm- onium), halosafen,
haloxyfop(-ethoxyethyl), haloxyfop-(-P-methyl), hexazinone,
imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic,
imazapyr, imazaquin, imazethapyr, imazosulfuron,
iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon,
isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop,
lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione,
metamitron, metazachlor, methabenzthiazuron, metobenzuron,
meto-bromuron, (alpha-)metolachlor, metosulam, metoxuron,
metribuzin, metsulfuron-(-methyl), molinate, monolinuron,
naproanilide, napropamide, neburon, nicosulfuron, norflurazon,
orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,
oxazi-clomefone, oxyfluorfen, paraquat, pelargonic acid,
pendimethalin, pentoxazone, phenmedipham, picolinafen, piperophos,
pretilachlor, primisulfuron(-methyl), procarbazone, prometryn,
propachlor, propanil, propaquizafop, propisochlor, propyzamide,
prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,
pyrazo-sulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,
pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac,
quinmerac, quinoclamine, quizalofop(-P-ethyl),
quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine,
simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),
sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,
terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,
thidiazimin, thifensulfuron(-methyl), thiobencarb, tio-carbazil,
tralkoxydim, triallate, triasulfuron, tribenuron(-methyl),
triclopyr, tridiphane, trifluralin, triflusulfuron and
tritosulfuron.
[0190] A mixture with other known active compounds, such as
fungicides, insecticides, acaricides, nematicides, bird repellents,
plant nutrients and agents which improve soil structure, is also
possible.
[0191] The active compounds can be used as such, in the form of
their formulations or in the use forms prepared therefrom by
further dilution, such as ready-to-use solutions, suspensions,
emulsions, powders, pastes and granules. They are used in the
customary manner, for example by watering, spraying, atomizing,
scattering.
[0192] The active compounds according to the invention can be
applied both before and after emergence of the plants. They can
also be incorporated into the soil before sowing.
[0193] The amount of active compound used can vary within a
relatively wide range. It depends essentially on the nature of the
desired effect. In general, the amounts used are between 1 g and 10
kg of active compound per hectare of soil surface, preferably
between 5 g and 5 kg per ha.
[0194] The preparation and the use of the active compounds
according to the invention can be seen from the examples below.
PREPARATION EXAMPLES
Example 1
[0195] 432
[0196] (Process (a))
[0197] At room temperature (about 20.degree. C.), a solution of
1.20 g (33% pure, i.e. 2.8 mMol) of methyl
4-(3-bromomethyl-5-trifluoromethyl-be-
nzoyl)-5-cyclopropyl-isoxazole-3-carboxylate in 10 ml of
N,N-dimethyl-formamide is added dropwise with stirring to a mixture
of 0.44 g (2.8 mMol) of
4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 84 mg (2.8
mMol) of sodium hydride (75% pure) and 20 ml of
N,N-dimethyl-formamide, and the reaction mixture is stirred at room
temperature for 30 minutes. The mixture is then diluted with
saturated aqueous sodium chloride solution to about twice its
original volume and extracted twice with ethyl acetate. The
combined organic extract solutions are dried with sodium sulphate
and filtered. The filtrate is concentrated under water pump vacuum
and the residue is purified by column chromatography (silica gel,
hexane/ethyl acetate, vol.: 7/3).
[0198] This gives 0.45 g (96% of theory based on 33% pure starting
material) of
(5-cyclo-propyl-3-methoxycarbonyl-isoxazol-4-yl)-[2-(4-ethox-
y-3-ethyl-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-trifluoromethyl-
-phenyl]-methanone as an amorphous product.
[0199] logP (determined at pH=2.3): 3.56.
Example 2
[0200] 433
[0201] (process (b))
[0202] A mixture of 1.5 g (36 mMol) of
1-cyclopropyl-3-[2-(4-methyl-3-meth-
ylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)4trifluoromethyl-phen-
yl]-propane-1,3-dione, 0.56 g (46 mMol) of N,N-dimethyl-formamide
dimethyl acetal and 15 ml of toluene is stirred at 90.degree. C.
for 60 minutes. The mixture is then concentrated under water pump
vacuum, the residue is taken up in 15 ml of ethanol and the mixture
is, after addition of 0.25 g (36 mMol) of hydroxylamine
hydrochloride, stirred at room temperature (about. 20.degree. C.)
for two hours. The mixture is concentrated under water pump vacuum,
the residue is shaken with methylene chloride/water and the organic
phase is separated off, washed with saturated aqueous sodium
chloride solution, dried with sodium sulphate and filtered. The
filtrate is concentrated under water pump vacuum and the residue is
purified by column chromatography (silica gel, ethyl
acetate/hexane, vol: 1/1).
[0203] This gives 0.20 g (13% of theory) of
(5-cyclopropyl-isoxazol-4-yl)--
[2-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-
-trifluoromethyl-phenyl]-methanone as an amorphous product.
[0204] logP (determined at pH=2.3): 2.94.
[0205] Analogously to Examples 1 and 2, and in accordance with the
general description of the preparation process according to the
invention, it is also possible to prepare, for example, the
compounds of the general formula (I)--or of the formulae (IA),
(IB), (IC) or (ID)--listed in Tables 1 and 1a below. 434
3TABLE 1a Examples of the compounds of the formula (I) or (ID) Ex.-
(position) (position) (position) No. R.sup.1 R.sup.2 R.sup.3
(R.sup.4).sub.n -A-Z physical data ID-1 435 H (2) Cl (4) Cl 436
logP = 2.48.sup.a) ID-2 437 H (2) OCH.sub.3 (4) Cl 438 logP =
2.46.sup.a) ID-3 439 H (2) Cl (4) 440 ID-4 441 H (2) OCH.sub.3 (4)
Cl 442 ID-5 443 H (2) Cl (4) Cl 444 ID-6 445 H (2) Cl (4) Cl 446
ID-7 447 H (2) Cl (4) Cl 448 ID-8 449 H (2) Cl (4) Cl 450 ID-9 451
H (2) Cl (4) Cl 452 ID-10 453 H (2) OCH.sub.3 (4) Cl 454 ID-11 455
H (2) Cl (4) SO.sub.2CH.sub.3 456 ID-12 457 H (2) Cl (4)
SO.sub.2CH.sub.3 458 ID-13 459 H (2) SO.sub.2CH.sub.3 (4) Cl 460
ID-14 461 H (2) SO.sub.2CH.sub.3 (4) Cl 462 ID-15 463 H (2) Cl (4)
CF.sub.3 464 ID-16 465 H (2) Cl (4) CF.sub.3 466 ID-17 467 H (2)
NO.sub.2 (4) CF.sub.3 468 ID-18 469 H (2) NO.sub.2 (4) CF.sub.3 470
ID-19 471 H (2) OCH.sub.3 (4) CF.sub.3 472 ID-20 473 H (2)
OCH.sub.3 (4) CF.sub.3 474 ID-21 475 H (2) Cl (4) CN 476 ID-22 477
H (2) Cl (4) CN 478 ID-23 479 H (2) OCH.sub.3 (4) CN 480 ID-24 481
H (2) OCH.sub.3 (4) CN 482 ID-25 483 H (2) Cl (4) F 484 ID-26 485 H
(2) Cl (4) F 486 ID-27 487 H H -- 488 ID-28 489 H H -- 490 ID-29
491 H (4) F -- 492 ID-30 493 H (4) F -- 494 ID-31 495 H (4) Cl --
496 ID-32 497 H (4) Cl -- 498 ID-33 499 H (4) F -- 500 ID-34 501 H
(4) Cl -- 502 ID-35 503 H (4) Br -- 504 ID-36 505 H (4) I -- 506
ID-37 507 H (4) NO.sub.2 -- 508 ID-38 509 H (4) CN -- 510 ID-39 511
H (4) CF.sub.3 -- 512 ID-40 513 H (4) SO.sub.2CH.sub.3 -- 514 ID-41
515 H (4) OCH.sub.3 -- 516 ID-42 517 H (4) OCF.sub.3 -- 518 ID-43
519 H (4) OCHF.sub.2 -- 520 ID-44 521 H (4) SCH.sub.3 -- 522 ID-45
523 H (4) SOCH.sub.3 -- 524 ID-46 525 526 (2) Cl (4) Cl 527 ID-47
528 529 (2) OCH.sub.3 (4) Cl 530 ID-48 531 532 (2) Cl (4) Cl 533
ID-49 534 535 (2) OCH.sub.3 (4) Cl 536 ID-50 537 SCH.sub.3 (2) Cl
(4) Cl 538 ID-51 539 SCH.sub.3 (2) OCH.sub.3 (4) Cl 540 ID-52 541
SCH.sub.3 (2) Cl (4) Cl 542 ID-53 543 SCH.sub.3 (2) OCH.sub.3 (4)
Cl 544 ID-54 545 H (2) Cl (4) Cl 546 ID-55 547 H (2) OCH.sub.3 (4)
Cl 548 ID-56 549 H (2) Cl (4) Cl 550 ID-57 551 H (2) OCH.sub.3 (4)
Cl 552 ID-58 553 H (4) CF.sub.3 -- 554 ID-59 555 H (4) CF.sub.3 --
556 ID-60 557 H (4) CF.sub.3 -- 558 ID-61 559 H (2) Cl (4) Cl 560
ID-62 561 H (2) OCH.sub.3 (4) Cl 562 ID-63 563 H (2) Cl (4) Cl 564
ID-64 565 H (2) OCH.sub.3 (4) Cl 566 ID-65 567 H (2) Cl (4) Cl 568
ID-66 569 H (2) OCH.sub.3 (4) Cl 570 ID-67 571 H (2) NO.sub.2 (4)
SO.sub.2CH.sub.3 572 ID-68 573 H (2) NO.sub.2 (4) SO.sub.2CH.sub.3
574 ID-69 575 H (2) Cl (4) SO.sub.2CH.sub.3 576 ID-70 577 H (2)
NO.sub.2 (4) SO.sub.2CH.sub.3 578 ID-71 579 H (2) NO.sub.2 (4)
CF.sub.3 580 ID-72 581 H (2) NO.sub.2 (4) CF.sub.3 582 ID-73 583 H
(2) NO.sub.2 (4) CF.sub.3 584 ID-74 585 H (2) Cl (4)
SO.sub.2CH.sub.3 586 ID-75 587 H (2) NO.sub.2 (4) SO.sub.2CH.sub.3
588 ID-76 589 H (2) NO.sub.2 (4) CF.sub.3 590 ID-77 591 H (2) Cl
(4) SO.sub.2CH.sub.3 592 ID-78 593 H (2) NO.sub.2 (4)
SO.sub.2CH.sub.3 594 ID-79 595 H (2) NO.sub.2 (4) CF.sub.3 596
[0206] The logP values given in Table 1 were determined in
accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High
Performance Liquid Chromatography) using a reverse-phase column (C
18). Temperature: 43.degree. C.
[0207] (a) Mobile phases for the determination in the acidic range:
0.1% aqueous phosphoric acid, acetonitrile; linear gradient from
10% acetonitrile to 90% acetonitrile--the corresponding data in
Table 1 are labelled .sup.a).
[0208] (b) Mobile phases for the determination in the neutral
range: 0.01 molar aqueous phosphate buffer solution, acetonitrile;
linear gradient from 10% acetonitrile to 90% acetonitrile--the
corresponding data in Table 1 are labelled .sup.b).
[0209] Calibration was carried out using unbranched alkan-2-ones
(with from 3 to 16 carbon atoms) whose logP values are known
(determination of the logP values by the retention times using
linear interpolation between two successive alkanones).
[0210] The lambda-max values were determined in the maxima of the
chromatographic signals, using the UV spectra from 200 nm to 400
nm.
[0211] Starting Materials of the Formula (II)
Example (II-1)
[0212] 597
[0213] A mixture of 3.0 g (8.5 Mol) of methyl
5-cyclopropyl-4-(2-methyl-4--
trifluoro-methyl-benzoyl)-isoxazole-4-carboxylate, 1.5 g (8.5 mMol)
of N-bromo-succinimide, 0.15 g of 2,2'-azo-bis-isobutyronitrile and
45 ml of carbon tetrachloride is heated under reflux for two hours
and, after cooling, filtered. The filtrate is diluted with
methylene chloride to about twice its original volume, washed with
20% strength aqueous sodium hydrogen sulphite solution, dried with
sodium sulphate and filtered. From the filtrate, the solvent is
carefully distilled off under water pump vacuum.
[0214] This gives 2.5 g (68% of theory) of methyl
5-cyclopropyl-4-(2-bromo-
methyl-4-trifluoromethyl-benzoyl)-isoxazole-4-carboxylate as an
amorphous product which can be reacted further without any
purification.
[0215] Analogously to Example (II-1), it is also possible to
prepare, for example, the compounds of the formula (II) listed in
Table 2 below.
4TABLE 2 (II) 598 Examples of the compounds of the formula (II)
Ex.- (position) (position) physical No. R.sup.1 R.sup.2 (position)
R.sup.3 (R.sup.4).sub.n A--X data II-2 599 600 (4) Br -- (2)
CH.sub.2Br II-3 601 602 (4) Cl -- (2) CH.sub.2Br II-4 603 604 (4)
CH.sub.3 -- (2) CH.sub.2Br II-5 605 606 (4) CN -- (2) CH.sub.2Br
II-6 607 608 (4) OCH.sub.3 -- (2) CH.sub.2Br II-7 609 610 (4)
SCH.sub.3 -- (2) CH.sub.2Br II-8 611 612 (4) SO.sub.2CH.sub.3 --
(2) CH.sub.2Br II-9 613 614 (4) SO.sub.2N(CH.sub.3).sub.2 -- (2)
CH.sub.2Br II-10 615 SCH.sub.3 (4) CF.sub.3 -- (2) CH.sub.2Br II-11
616 617 (4) OCHF.sub.2 -- (2) CH.sub.2Br II-12 618 619 (4)
OCF.sub.3 -- (2) CH.sub.2Br II-13 620 621 (4) NO.sub.2 -- (2)
CH.sub.2Br II-14 622 623 (4) Cl (2) Cl (3) CH.sub.2Br II-15 624 H
(4) Cl (2) Cl (3) CH.sub.2Br II-16 625 626 (4) Cl (2) Cl (3)
CH.sub.2Br II-17 627 628 H -- (3) CH.sub.2Br II-18 629 H H -- (3)
CH.sub.2Br II-19 630 H (4) Cl (2) OCH.sub.3 (3) CH.sub.2Br II-20
631 H (4) CH.sub.3 (3) OCH.sub.3 (2) CH.sub.2Br II-21 632 H (4) CN
(3) OCH.sub.3 (2) CH.sub.2Br II-22 633 H (4) SO.sub.2CH.sub.3 (3)
CH.sub.2OCH.sub.3 (2) CH.sub.2Br II-23 634 H (4) CF.sub.3 (3)
CH.sub.2OCH.sub.3 (2) CH.sub.2Br II-24 635 H (4) F (2) Cl (3)
CH.sub.2Br
[0216] Starting Materials of the Formula (IV)
Example (IV-1)
[0217] 636
[0218] A mixture of 0.94 g (11 mMol) of cyclopropyl methyl ketone,
0.35 g (11 mMol) of sodium hydride (75% pure) and 15 ml of
tetrahydrofiran is stirred at 20.degree. C. for 30 minutes. A
solution of 2.0 g (5.5 mMol) of
4-methyl-5-methylthio-2-(2-methoxy-carbonyl-5-trifluoromethyl-benzyl)--
2,4-dihydro-3H-1,2,4-triazol-3-one in 8 ml of tetrahydrofuran is
then added dropwise and, after addition of 0.2 g of
dibenzo-18-crone-6, the reaction mixture is heated under reflux for
60 minutes. After cooling to room temperature, the mixture is
diluted with 100 ml of ethyl acetate, shaken with saturated aqueous
ammonium chloride solution, dried with sodium sulphate and filtered
through silica gel. From the filtrate, the solvent is carefully
distilled off under water pump vacuum.
[0219] This gives 1.5 g (66% of theory) of
1-cyclopropyl-3-[4-methyl-3-met-
hylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-phenyl]-propane-1,3-
-dione as an amorphous product which can be reacted further without
purification.
[0220] Starting Materials of the Formula (VII)
Example (VII-1)
[0221] 637
[0222] 10 g (49 mMol) of 2-methyl-4-trifluoromethyl-benzoic acid
are dissolved in 150 ml of ethanol and admixed with 1 ml of conc.
sulphuric acid. The mixture is heated under reflux for 24 hours and
then concentrated, the residue is taken up in methylene chloride
and the mixture is extracted with saturated aqueous sodium
bicarbonate solution. The methylene chloride phase is dried over
sodium sulphate and concentrated under water pump vacuum.
[0223] This gives 9 g (80% of theory) of ethyl
2-methyl-4-trifluoromethyl-- benzoate as an amorphous residue.
638
[0224] 9 g (39 mMol) of ethyl 2-methyl-4-trifluoromethyl-benzoate
are dissolved in 200 ml of carbon tetrachloride and admixed with 7
g (39 nMol) of N-bromo-succinimide and 0.1 g of dibenzoyl peroxide.
After 6 hours of heating under reflux, the succinimide which has
separated off is filtered off, and the filtrate is concentrated
under water pump vacuum.
[0225] This gives 12 g of an amorphous residue which, in addition
to ethyl 2-bromomethyl-4-trifluoromethyl-benzoate, contains 17% of
ethyl 2,2-dibromomethyl-4-trifluoro-methyl-benzoate and 12% of
ethyl 2-methyl-4-trifluoromethyl-benzoate. 639
[0226] 4 g of ethyl 2-bromomethyl-4-trifluoromethyl-benzoate (about
70% pure) and 2.28 g (12.8 mMol) of
5-bromo-4-methyl-2,4-dihydro-3H-1,2,4-tri- azol-3-one are dissolved
in 150 ml of acetonitrile and the solution is admixed with 5.3 g
(38.4 Mol) of potassium carbonate and heated under reflux with
vigorous stirring for 2 hours. The reaction mixture is taken up in
water and repeatedly extracted with methylene chloride. The
combined methylene chloride phases are dried over sodium sulphate,
concentrated under water pump vacuum and chromatographed.
[0227] This gives 2 g (38% of theory) of
5-bromo-4-methyl-2-(2-ethoxycarbo-
nyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as
an amorphous product.
[0228] .sup.1H-NMR (CDCl.sub.3, 8): 5.46 ppm.
Example (VII-2)
[0229] 640
[0230] 6.7 g (40 Mol) of
4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-t- riazol-3-one are
initially charged in 150 ml of acetonitrile and stirred with 11 g
(80 mMol) of potassium carbonate. The mixture is heated to
50.degree. C., and a solution of 13.1 g (44 mMol) of methyl
3-bromomethyl-2,4-dichloro-benzoate in 20 ml of acetonitrile is
then added dropwise with stirring, and the reaction mixture is
heated with stirring and at reflux for another 15 hours. The
mixture is then concentrated under water pump vacuum and the
residue is taken up in methylene chloride, washed with 1N
hydrochloric acid, dried with sodium sulphate and filtered. The
filtrate is concentrated under reduced pressure, the residue is
digested with petroleum ether and the resulting crysalline product
is isolated by filtration with suction.
[0231] This gives 14.9 g (97% of theory) of
4-methyl-5-trifluoromethyl-2-(-
2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
of melting point 109.degree. C.
[0232] Analogously to the Examples (VII-1) and (VII-2), it is also
possible to prepare, for example, the compounds of the general
formula (VII) listed in Table 3 below.
5TABLE 3 (VII) 641 Examples of the compounds of the formula (VII)
Ex. (position) (position) (position) physical No. R.sup.3
(R.sup.4).sub.n --A--Z Y data VII-3 (2-) Cl (4-) Cl 642 OCH.sub.3
m.p.: 229.degree. C. logP = 2.27.sup.a VII-4 (2-) Cl (4-) Cl 643
OCH.sub.3 m.p.: 120.degree. C. logP = 2.38.sup.a VII-5 (2-) Cl (4-)
Cl 644 OCH.sub.3 m.p.: 127.degree. C. logP = 2.55.sup.a VII-6 (2-)
Cl (4-) Cl 645 OCH.sub.3 m.p.: 121.degree. C. logP = 2.04.sup.a
VII-7 (2-) Cl (4-) Cl 646 OCH.sub.3 m.p.: 68.degree. C. logP =
2.73.sup.a VII-8 (2-) Cl (4-) Cl 647 OCH.sub.3 m.p.: 129.degree. C.
logP = 2.72.sup.a VII-9 (2-) Cl (4-) Cl 648 OCH.sub.3 m.p.:
164.degree. C. logP = 2.18.sup.a VII-10 (2-) Cl (4-) Cl 649
OCH.sub.3 m.p.: 158.degree. C. logP = 1.55.sup.a VII-11 (2-) Cl
(4-) Cl 650 OCH.sub.3 m.p.: 106.degree. C. logP = 2.16.sup.a VII-12
(2-) Cl (4-) Cl 651 OCH.sub.3 m.p.: 126.degree. C. logP =
2.11.sup.a VII-13 (2-) Cl (4-) Cl 652 OCH.sub.3 m.p.: 146.degree.
C. logP = 1.65.sup.a VII-14 (2-) Cl (4-) Cl 653 OCH.sub.3 m.p.:
178.degree. C. logP = 1.86.sup.a VII-15 (2-) Cl (4-) Cl 654
OCH.sub.3 m.p.: 97.degree. C. logP = 2.36.sup.a VII-16 (2-) Cl (4-)
Cl 655 OCH.sub.3 m.p.: 99.degree. C. logP = 2.73.sup.a VII-17 (2-)
Cl (4-) Cl 656 OCH.sub.3 m.p.: 56.degree. C. logP = 3.08.sup.a
VII-18 (2-) Cl (4-) Cl 657 OCH.sub.3 m.p.: 102.degree. C. logP =
3.05.sup.a VII-19 (2-) Cl (4-) Cl 658 OCH.sub.3 m.p.: 131.degree.
C. logP = 2.70.sup.a VII-20 (2-) Cl (4-) Cl 659 OCH.sub.3 m.p.:
135.degree. C. logP = 1.97.sup.a VII-21 (2-) Cl (4-) Cl 660
OCH.sub.3 m.p.: 143.degree. C. logP = 2.42.sup.a VII-22 (2-) Cl
(4-) Cl 661 OCH.sub.3 m.p.: 85.degree. C. logP = 2.58.sup.a VII-23
(2-) Cl (4-) Cl 662 OCH.sub.3 logP = 1.98.sup.a VII-24 (2-) Cl (4-)
Cl 663 OCH.sub.3 logP = 2.07.sup.a VII-25 (2-) Cl (4-) Cl 664
OCH.sub.3 m.p.: 157.degree. C. logP = 2.94.sup.a VII-26 (4-)
CF.sub.3 -- 665 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.):
5.53 ppm. VII-27 (4-) NO.sub.2 -- 666 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.48 ppm. VII-28 (4-) NO.sub.2 -- 667
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.30 ppm. VII-29
(4-) SO.sub.2CH.sub.3 -- 668 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.61 ppm. VII-30 (4-) Cl -- 669
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.08 ppm. VII-31
(4-) Cl -- 670 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.):
5.17 ppm. VII-32 (4-) Cl -- 671 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.00 ppm VII-33 (4-) SO.sub.2CH.sub.3 -- 672
OC.sub.2H.sub.5 logP = 1.53.sup.a VII-34 (4-) Br -- 673
OC.sub.2H.sub.5 logP = 3.24.sup.a VII-35 (4-) Br -- 674
OC.sub.2H.sub.5 logP = 3.40.sup.a VH-36 (4-) F -- 675
OC.sub.2H.sub.5 logP = 2.41.sup.a VII-37 (4-) F -- 676
OC.sub.2H.sub.5 logP = 2.45.sup.a VII-38 (4-) Br -- 677
OC.sub.2H.sub.5 logP = 2.06.sup.a VII-39 (4-) Br -- 678
OC.sub.2H.sub.5 logP = 2.64.sup.a VII-40 (4-) Br -- 679
OC.sub.2H.sub.5 logP = 3.23.sup.a VII-41 (4-) Br -- 680
OC.sub.2H.sub.5 logP = 3.02.sup.a VII-42 (4-) Cl -- 681
OC.sub.2H.sub.5 logP = 3.23.sup.a VII-43 (4-) Cl -- 682
OC.sub.2H.sub.5 logP = 3.31.sup.a VII-44 (4-) Cl -- 683
OC.sub.2H.sub.5 logP = 3.14.sup.a VII-45 (4-) NO.sub.2 -- 684
OC.sub.2H.sub.5 logP = 2.42.sup.a VII-46 (4-) NO.sub.2 -- 685
OC.sub.2H.sub.5 logP = 2.82.sup.a VII-47 (4-) CF.sub.3 -- 686
OC.sub.2H.sub.5 logP = 3.48.sup.a VII-48 (4-) CF.sub.3 -- 687
OC.sub.2H.sub.5 logP = 3.38.sup.a VII-49 (4-) CF.sub.3 -- 688
OC.sub.2H.sub.5 logP = 3.02.sup.a VII-50 (4-) CF.sub.3 -- 689
OC.sub.3H.sub.7 logP = 3.91.sup.a VII-51 (4-) OCH.sub.3 -- 690
OC.sub.2H.sub.5 VII-52 (4-) OCH.sub.3 -- 691 OC.sub.2H.sub.5 VII-53
(4-) CF.sub.3 -- 692 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3,
.delta.): 5.37 ppm. VII-54 (4-) CF.sub.3 -- 693 OC.sub.2H.sub.5
.sup.1H-NMR (CDCl.sub.3, .delta.): 5.37 ppm. VII-55 -- -- 694
OC.sub.2H.sub.5 VII-56 -- -- 695 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.37 ppm. VII-57 -- -- 696 OC.sub.2H.sub.5
.sup.1H-NMR (CDCl.sub.3, .delta.): 5.40 ppm. VII-58 (4-) Br -- 697
OC.sub.2H.sub.5 logP = 2.95.sup.a VII-59 (4-) Br -- 698
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.31 ppm. VII-60
(4-) Br -- 699 OC.sub.2H.sub.5 logP = 2.44.sup.a VII-61 (4-) F --
700 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.35 ppm.
VII-62 (4-) F -- 701 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3,
.delta.): 5.53 ppm. VII-63 (4-) F -- 702 OC.sub.2H.sub.5
.sup.1H-NMR (CDCl.sub.3, .delta.): 5.40 ppm. VII-64 (4-) F -- 703
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.36 ppm. VII-65
(4-) Br -- 704 OC.sub.2H.sub.5 logP = 3.34.sup.a VII-66 (4-) Br --
705 OC.sub.2H.sub.5 logP = 3.38.sup.a VII-67 (4-) Br -- 706
OC.sub.2H.sub.5 logP = 3.31.sup.a VII-68 (4-) Br -- 707
OC.sub.2H.sub.5 logP = 2.16.sup.a VII-69 (4-) Br -- 708
OC.sub.2H.sub.5 logP = 2.41.sup.a VII-70 (4-) CF.sub.3 -- 709
OC.sub.2H.sub.5 logP = 3.51.sup.a VII-71 (4-) CF.sub.3 -- 710
OC.sub.2H.sub.5 logP = 3.54.sup.a VII-72 (4-) Br -- 711
OC.sub.2H.sub.5 logP = 2.36.sup.a VII-73 (4-) Br -- 712
OC.sub.2H.sub.5 logP = 2.88.sup.a VII-74 (4-) CF.sub.3 -- 713
OC.sub.2H.sub.5 logP = 2.68.sup.a VII-75 (4-) Br -- 714
OC.sub.2H.sub.5 logP = 2.80.sup.a VII-76 (4-) CF.sub.3 -- 715
OC.sub.2H.sub.5 logP = 3.87.sup.a VII-77 (4-) CF.sub.3 -- 716
OC.sub.2H.sub.5 logP = 2.88.sup.a VII-78 (4-) CF.sub.3 -- 717
OC.sub.2H.sub.5 logP = 2.60.sup.a VII-79 (4-) CF.sub.3 -- 718
OC.sub.2H.sub.5 logP = 3.35.sup.a VII-80 (4-) Br -- 719
OC.sub.2H.sub.5 logP = 2.86.sup.a VII-81 (4-) Cl -- 720
OC.sub.2H.sub.5 logP = 2.83.sup.a VII-82 (4-) Br -- 721
OC.sub.2H.sub.5 logP = 2.60.sup.a VII-83 (4-) CF.sub.3 -- 722
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.36 ppm. VII-84
(4-) CF.sub.3 -- 723 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3,
.delta.): 5.37 ppm. VII-85 (4-) CF.sub.3 -- 724 OC.sub.2H.sub.5
logP = 2.79.sup.2 VII-86 (4-) CF.sub.3 -- 725 OC.sub.2H.sub.5 logP
= 3.67.sup.a VII-87 (4-) CF.sub.3 -- 726 OC.sub.2H.sub.5 logP =
3.80.sup.a VII-88 (3-) CH.sub.3 -- 727 OC.sub.2H.sub.5 logP =
2.54.sup.a VII-89 (4-) -- 728 OC.sub.2H.sub.5 logP = 1.82.sup.a
VII-90 (4-) CF.sub.3 -- 729 OC.sub.2H.sub.5 logP = 2.93.sup.a
VII-91 (4-) CF.sub.3 -- 730 OC.sub.2H.sub.5 logP = 3.08.sup.a
VII-92 (4-) CF.sub.3 -- 731 OC.sub.2H.sub.5 logP = 3.04.sup.a
VII-93 (4-) CF.sub.3 -- 732 OC.sub.2H.sub.5 logP = 3.45.sup.a
VII-94 (4-) F -- 733 OC.sub.2H.sub.5 logP = 2.21.sup.a VII-95 (4-)
F -- 734 OC.sub.2H.sub.5 logP = 2.96.sup.a VII-96 (4-) F -- 735
OC.sub.2H.sub.5 logP = 2.05.sup.a VII-97 (4-) F -- 736
OC.sub.2H.sub.5 logP = 2.50.sup.a VII-98 (4-) F -- 737
OC.sub.2H.sub.5 logP = 2.89.sup.a VII-99 (4-) CF.sub.3 -- 738
OC.sub.2H.sub.5 logP = 2.91.sup.a VII-100 (4-) Cl -- 739
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.39 ppm.
VII-101 (4-) Cl -- 740 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3,
.delta.): 5.50 ppm. VII-102 (4-) Cl -- 741 OC.sub.2H.sub.5
.sup.1H-NMR (CDCl.sub.3, .delta.): 5.49 ppm. VII-103 (4-) CF.sub.3
-- 742 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.29 ppm.
VII-104 (4-) CF.sub.3 -- 743 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.53 ppm. VII-105 (4-) CF.sub.3 -- 744
OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.34 ppm.
VII-106 (4-) SO.sub.2CH.sub.3 -- 745 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.39 ppm. VII-107 (4-) SO.sub.2CH.sub.3 --
746 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.43 ppm.
VH-108 (4-) SO.sub.2CH.sub.3 -- 747 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.40 ppm. VII-109 (4-) SO.sub.2CH.sub.3 --
748 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3, .delta.): 5.38 ppm.
VII-110 (4-) Br -- 749 OC.sub.2H.sub.5 .sup.1H-NMR (CDCl.sub.3,
.delta.): 5.49 ppm. VII-111 -- -- 750 OC.sub.2H.sub.5 .sup.1H-NMR
(CDCl.sub.3, .delta.): 5.3 ppm. VII-112 -- -- 751 OC.sub.2H.sub.5
.sup.1H-NMR (CDCl.sub.3, .delta.): 5.44 ppm. VII-113 (4-) CF.sub.3
-- 752 OC.sub.2H.sub.5 logP = 2.58.sup.a VII-114 (4-)
SO.sub.2CH.sub.3 -- 753 OCH.sub.3 logP = 1.53.sup.a VII-115 (4-)
SO.sub.2CH.sub.3 -- 754 OCH.sub.3 logP = 1.59.sup.a VII-116 (4-) I
-- 755 OCH.sub.3 logP = 2.68.sup.a VII-117 (4-) CF.sub.3 -- 756
OCH.sub.3 logP = 2.74.sup.a VII-118 (4-) CF.sub.3 -- 757 OCH.sub.3
logP = 2.65.sup.a VII-119 (4-) CF.sub.3 -- 758 OC.sub.2H.sub.5 logP
= 2.96.sup.a VII-120 -- -- 759 OCH.sub.3 m.p.: 106.degree. C.
VII-121 (4-) CF.sub.3 -- 760 OCH.sub.3 logP = 3.37.sup.a VII-122
(4-) CF.sub.3 -- 761 OCH.sub.3 logP = 3.29.sup.a VII-123 (4-)
CF.sub.3 -- 762 OCH.sub.3 logP = 3.26.sup.a VII-124 (4-) Cl (2-)
OCH.sub.3 763 OCH.sub.3 .sup.1H-NMR (DMSO-D.sub.6, .delta.): 4.44
ppm. VII-125 (4-) Cl (2-) OCH.sub.3 764 OCH.sub.3 .sup.1H-NMR
(DMSO-D.sub.6, .delta.): 4.66 ppm. VII-126 (4-) Cl (2-) OCH.sub.3
765 OCH.sub.3 .sup.1H-NMR (DMSO-D.sub.6, .delta.): 4.95 ppm.
[0233] The logP values given in Table 3 were determined in
accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High
Performance Liquid Chromatography) using a reverse-phase column (C
18). Temperature: 43.degree. C.
[0234] (a) Mobile phases for the determination in the acidic range:
0.1% aqueous phosphoric acid, acetonitrile; linear gradient from
10% acetonitrile to 90% acetonitrile--the corresponding data in
Table 3 are labelled .sup.a).
[0235] (b) Mobile phases for the determination in the neutral
range: 0.01 molar aqueous phosphate buffer solution, acetonitrile;
linear gradient from 10% acetonitrile to 90% acetonitrile--the
corresponding data in Table 3 are labelled .sup.b).
[0236] Calibration was carried out using unbranched alkan-2-ones
(with from 3 to 16 carbon atoms) whose logP values are known
(determination of the logP values by the retention times using
linear interpolation between two successive alkanones).
[0237] The lambda-max values were determined in the maxima of the
chromatographic signals, using the UV spectra from 200 nm to 400
nm.
Use Examples
Example A
[0238] Pre-Emergence Test
6 Solvent: 5 parts by weight of acetone Emulsifier: 1 part by
weight of alkylaryl polyglycol ether
[0239] To produce a suitable preparation of active compound, 1 part
by weight of active compound is mixed with the stated amount of
solvent, the stated amount of emulsifier is added and the
concentrate is diluted with water to the desired concentration.
[0240] Seeds of the test plants are sown in normal soil. After
about 24 hours, the soil is sprayed with the preparation of active
compound such that the particular amount of active compound desired
is applied per unit area. The concentration of the spray liquor is
chosen so that the particular amount of active compound desired is
applied in 1000 litres of water per hectare.
[0241] After three weeks, the degree of damage to the plants is
rated in % damage in comparison to the development of the untreated
control.
[0242] The figures denote:
7 0% = no effect (like untreated control) 100% = total
destruction
[0243] In this test, for example, the compounds of preparation
examples 3 and 4 exhibit strong action against weeds, whilst being
tolerated well by crop plants, such as, for example, maize.
Example B
[0244] Post-Emergence Test
8 Solvent: 5 parts by weight of acetone Emulsifier: 1 part by
weight of alkylaryl polyglycol ether
[0245] To produce a suitable preparation of active compound, 1 part
by weight of active compound is mixed with the stated amount of
solvent, the stated amount of emulsifier is added and the
concentrate is diluted with water to the desired concentration.
[0246] Test plants which have a height of 5-15 cm are sprayed with
the preparation of active compound such that the particular amounts
of active compound desired are applied per unit area. The
concentration of the spray liquor is chosen so that the particular
amounts of active compound desired are applied in 1000 1 of
water/ha.
[0247] After three weeks, the degree of damage to the plants is
rated in % damage in comparison to the development of the untreated
control.
[0248] The figures denote:
9 0% = no effect (like untreated control) 100% = total
destruction
[0249] In this test, for example, the compounds of Preparation
Examples 3 and 4 exhibit very strong activity against weeds, whilst
being tolerated well by crop plants, such as, for example,
wheat.
* * * * *