Substituted aromatic thiocarboxylic acid amides and their use as herbicides

There is disclosed substituted thiocarboxamides of the general formula (I) ##STR1## , wherein Z, R.sup.1, R.sup.2 and R.sup.3 are as defined by the specification, which are useful herbicidal agents.

This application is a 371 of PCT/EP95/01507 filed Apr. 21, 1995. 
The invention relates to novel substituted aromatic thiocarboxamides, to 
processes for their preparation and to their use as herbicides. 
It is already known that certain aromatic carbothioamides, for example 
2,6-dichlorobenzothioamide ("chlorthiamid"), possess herbicidal properties 
(cf. GB-B 987253). However, the activity of this previously known 
compound, especially at low application rates and concentrations, is not 
entirely satisfactory in all areas of application. 
The novel substituted aromatic thiocarboxamides have now been found of the 
general formula (I) 
##STR2## 
in which 
R.sup.1 represents hydrogen or halogen, 
R.sup.2 represents the following group 
EQU --A.sup.1 --A.sup.2 --A.sup.3 
in which 
A.sup.1 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, 
alkylsulphonyl or arylsulphonyl, 
A.sup.1 additionally represents in each case optionally substituted 
alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or 
arenediyl, 
A.sup.2 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, aryl, alkoxy, 
alkylsulphonyl or arylsulphonyl, 
A.sup.2 additionally represents in each case optionally substituted 
alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or 
arenediyl, 
A.sup.3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, 
nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, 
halogen or represents in each case optionally substituted alkyl, alkoxy, 
alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, 
alkoxycarbonyl, dialkoxy(thio)phosphoryl, alkenyl, alkenyloxy, 
alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, 
alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, 
cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, 
cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, 
arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, 
heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl, 
R.sup.3 represents hydrogen or halogen or together with R.sup.2 represents 
an alkanediyl or an alkenediyl group which optionally contains at the 
beginning (or end) or within the hydrocarbon chain an oxygen atom, a 
sulphur atom, an SO.sub.2 group, an NH group, an N-alkyl group, a carbonyl 
group and/or a thiocarbonyl group, and 
Z represents in each case optionally substituted monocyclic or bicyclic, 
saturated or unsaturated heterocyclyl, heterocyclylamino or 
heterocyclylimino. 
The novel substituted aromatic thiocarboxamides of the general formula (I) 
are obtained if substituted aromatic nitrites of the general formula (II) 
##STR3## 
in which 
R.sup.1, R.sup.2, R.sup.3 and Z have the meanings given above are reacted 
with hydrogen sulphide (H.sub.2 S) or with thioacetamide, optionally in 
the presence of a reaction auxiliary and optionally in the presence of a 
diluent 
The novel substituted aromatic thiocarboxamides of the general formula (1) 
are notable for strong and selective herbicidal activity. 
In the definitions, the saturated or unsaturated hydrocarbon chains, such 
as alkyl, alkanediyl, alkenyl or alkinyl--alone or in conjunction with 
heteroatoms, such as in alkoxy, alkylthio or alkylamino--are each 
straight-chain or branched. 
Halogen generally represents fluorine, chlorine, bromine or iodine, 
preferably fluorine, chlorine or bromine, especially fluorine or chlorine. 
The invention preferably relates to compounds of the formula (I) in which 
R.sup.1 represents hydrogen, fluorine, chlorine or bromine, 
R.sup.2 represents the following group 
EQU --A.sup.1 --A.sup.2 --A.sup.3 
in which 
A.sup.1 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 
-alkenyl, C.sub.3 -C.sub.4 -alkinyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, 
C.sub.1 -C.sub.4 -alkylsulphonyl or phenylsulphonyl, 
A.sup.1 additionally represents in each case optionally fluorine- or 
chlorine-substituted C.sub.1 -C.sub.6 -alkanediyl, C.sub.2 -C.sub.6 
-alkenediyl, C.sub.2 -C.sub.6 -alkinediyl, C.sub.3 -C.sub.6 
-cycloalkanediyl, C.sub.3 -C.sub.6 -cycloalkenediyl or phenylene, 
A.sup.2 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 
-alkenyl, C.sub.3 -C.sub.4 -alkinyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, 
C.sub.1 -C.sub.4 -alkylsulphonyl or phenylsulphonyl, 
A.sup.2 additionally represents in each case optionally fluorine- or 
chlorine-substituted C.sub.1 -C.sub.6 -alkanediyl, C.sub.2 -C.sub.6 
-alkenediyl, C.sub.2 -C.sub.6 -alkinediyl, C.sub.3 -C.sub.6 
-cycloalkanediyl, C.sub.3 -C.sub.6 -cycloalkenediyl or phenylene, 
A.sup.3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, 
nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, 
halogen, or represents in each case optionally halogen- or C.sub.1 
-C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, 
alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or 
dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the 
alkyl groups, or represents in each case optionally halogen-substituted 
alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, 
alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each 
case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, or 
represents in each case optionally halogen-, cyano-, carboxyl-, C.sub.1 
-C.sub.4 -alkyl- and/or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted 
cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, 
cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl 
having in each case 3 to 6 carbon atoms in the cycloalkyl groups and 
optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each 
case optionally nitro-, cyano-, carboxyl-, halogen-, C.sub.1 -C.sub.4 
-alkyl-, C.sub.1 -C.sub.4 -halogenoalkyl-, C.sub.1 -C.sub.4 -alkyloxy-, 
C.sub.1 -C.sub.4 -halogenoalkyloxy- and/or C.sub.1 -C.sub.4 
-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C.sub.1 -C.sub.4 
-alkyl, phenyl-C.sub.1 -C.sub.4 -alkoxy, phenyloxycarbonyl or 
phenyl-C.sub.1 -C.sub.4 -alkoxycarbonyl, (in each case optionally totally 
or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, 
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 
oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, 
pyrazolyl-C.sub.1 -C.sub.4 -alkyl, furyl-C.sub.1 -C.sub.4 -alkyl, 
thienyl-C.sub.1 -C.sub.4 -alkyl, oxazolyl-C.sub.1 --C.sub.4 -alkyl, 
isoxazole-C.sub.1 -C.sub.4 -alkyl, thiazole-C.sub.1 -C.sub.4 -alkyl, 
pyridinyl-C.sub.1 -C.sub.4 -alkyl, pyrimidinyl-C.sub.1 -C.sub.4 -alkyl, 
pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or 
pyridylmethoxy, 
R.sup.3 represents hydrogen, fluorine, chlorine or bromine or together with 
R.sup.2 represents an alkanediyl or alkenediyl group having in each case 
up to 4 carbon atoms which optionally contains at the beginning (or end) 
or within the hydrocarbon chain an oxygen atom, a sulphur atom, an 
SO.sub.2 group, an NH group, an N--C.sub.1 --C.sub.4 -alkyl group, a 
carbonyl group and/or a thiocarbonyl group, and 
Z represents in each case monocyclic or bicyclic, saturated or unsaturated 
heterocyclyl, heterocyclylamino or heterocyclylimino having in each case 2 
to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring 
system, which optionally additionally contains an oxygen atom or sulphur 
atom and/or optionally up to three groups from the series --CO--, --CS--, 
--SO-- and/or SO.sub.2 --, and which is optionally substituted by one or 
more groups from the series nitro, hydroxyl, amino, cyano, carboxyl, 
carbamoyl, thiocarbamoyl, halogen, C.sub.1 -C.sub.6 -alkyl (which is 
optionally substituted by halogen or C.sub.1 -C.sub.4 -alkoxy), C.sub.2 
-C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkinyl (which are in each case 
optionally substituted by halogen), C.sub.1 -C.sub.6 -alkoxy or C.sub.1 
-C.sub.6 -alkoxy-carbonyl (which are in each case optionally substituted 
by halogen or C.sub.1 -C.sub.4 -alkoxy), C.sub.2 -C.sub.6 -alkenyloxy or 
C.sub.2 -C.sub.6 -alkinyloxy (which are in each case optionally 
substituted by halogen), C.sub.2 -C.sub.6 -alkylthio, C.sub.2 -C.sub.6 
-alkenylthio or C.sub.2 -C.sub.6 -alkinylthio (which are in each case 
optionally substituted by halogen), C.sub.1 -C.sub.6 -alkylamino or 
di-(C.sub.1 -C.sub.4 -alkyl)-amino, C.sub.3 -C.sub.6 -cycloalkyl or 
C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl (which are in each 
case optionally substituted by halogen and/or C.sub.1 -C.sub.4 -alkyl), 
phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl or 
phenylamino (which are in each case optionally substituted by nitro, 
cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, 
C.sub.1 -C.sub.4 -alkyloxy, C.sub.1 -C.sub.4 -halogenoalkyloxy and/or 
C.sub.1 -C.sub.4 -alkoxy-carbonyl). 
The invention particularly relates to compounds of the formula (I) in which 
R.sup.1 represents hydrogen, fluorine or chlorine, 
R.sup.2 represents the following group 
EQU --A.sup.1 --A.sup.2 --A.sup.3 
in which 
A.sup.1 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, 
ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, 
A.sup.1 additionally represents methylene, ethane-1,1-diyl, 
ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, 
ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, 
propine-1,2-diyl or propine-1,3-diyl, 
A.sup.2 represents a single bond, or represents oxygen, sulphur, --SO--, 
--SO.sub.2 --, --CO-- or the group --N--A.sup.4 --, in which A.sup.4 
represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, 
ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or 
i-propylsulphonyl or phenylsulphonyl, 
A.sup.2 additionally represents methylene, ethane-1,1-diyl, 
ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, 
ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, 
propine-1,2-diyl or propine-1,3-diyl, 
A.sup.3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, 
carbamoyl, sulpho, fluorine, chlorine, bromine, or represents in each case 
optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, 
ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, 
methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or 
t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or 
t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, 
methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, 
ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, 
dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or 
i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, 
dipropoxyphosphoryl or diisopropoxyphosphoryl, or represents in each case 
optionally fluorine- or chlorine-substituted propenyl, butenyl, 
propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, 
butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, 
butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, 
propinyloxycarbonyl or butinyloxycarbonyl, or represents in each case 
optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or 
i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, 
cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, 
cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, 
cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, 
cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 
cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, 
cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or 
cyclohexylmethoxycarbonyl, or represents in each case optionally nitro-, 
cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or 
i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, 
difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or 
ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, 
benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally 
completely or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, 
triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 
oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, 
pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, 
isoxazolemethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, 
pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, 
R.sup.3 represents hydrogen, fluorine or chlorine or together with R.sup.2 
represents an alkanediyl or alkenediyl group having in each case 1 to 3 
carbon atoms which optionally contains at the beginning (or end) or within 
the hydrocarbon chain an oxygen atom, a sulphur atom, an NH group, an 
N-methyl group, a carbonyl group and/or a thiocarbonyl group, and 
Z represents in each case monocyclic or bicyclic, saturated or unsaturated 
heterocyclyl, heterocyclylamino or heterocyclylimino having in each case 2 
to 5 carbon atoms and 1 to 3 nitrogen atoms in the heterocyclic ring 
system, which optionally additionally contains an oxygen atom or sulphur 
atom and/or optionally up to two groups from the series --CO--, --CS--, 
--SO-- and/or SO.sub.2 --, and which is optionally substituted by one or 
more groups from the series nitro, hydroxyl, amino, cyano, carboxyl, 
carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine; methyl, ethyl, n- 
or i-propyl, n-, i-, s- or t-butyl, (which are optionally substituted by 
fluorine, chlorine, methoxy or ethoxy); propenyl, butenyl, propinyl or 
butinyl (which are in each case optionally substituted by fluorine or 
chlorine); methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 
methoxycarbonyl or ethoxycarbonyl (which are in each case optionally 
substituted by fluorine, chlorine, methoxy or ethoxy); propenyloxy, 
butenyloxy, propinyloxy or butinyloxy (which are optionally substituted by 
fluorine or chlorine); methylthio, ethylthio, n- or i-propylthio, n-, i-, 
s- or t-butylthio, propenylthio, butenylthio, propinylthio or butinylthio 
(which are in each case optionally substituted by fluorine or chlorine); 
methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, 
dimethylamino or diethylamino; cyclopropyl, cyclobutyl, cyclopentyl, 
cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or 
cyclohexylmethyl (which are in each case optionally substituted by 
fluorine, chlorine, methyl, ethyl, n- or i-propyl), phenyl, phenoxy, 
phenylthio, phenylsulphinyl, phenylsulphonyl, or phenylamino (which are in 
each case optionally substituted by nitro, cyano, fluorine, chlorine, 
bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, 
n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or 
ethoxycarbonyl). 
Very particularly preferred groups of compounds of the formula (I) are the 
compounds of the formulae (Ia), (Ib) and (Ic) drawn below 
##STR4## 
where 
R.sup.1, R.sup.2 and Z have the meanings indicated above as particularly 
preferred, 
R.sup.4 and R.sup.5 are identical or different and independently of one 
another in each case individually represent hydrogen, fluorine, chlorine, 
methyl or ethyl--or in the formula (Ib) can also together represent oxygen 
or sulphur--and 
Q represents oxygen, sulphur, N-methyl or N-ethyl. 
Z in the general formulae (I) and ((Ia), (Ib) and (Ic) represents in 
particular the heterocyclic groups listed below 
##STR5## 
where in each case 
Q.sup.1 represents a group from the series --CO--, --CS--, --CH.sub.2 --, 
--CH(OH)--, --CHCl--, --CHBr--, --C(.dbd.CH.sub.2)--, --C(.dbd.CHF)--, 
--C(.dbd.CF.sub.2)--, --C(.dbd.CHCl)--, --C(.dbd.CHBr)--, 
--C(.dbd.CHOCHF.sub.2)--, --C(.dbd.CHOCF.sub.3)--, --C(.dbd.CHOCH.sub.2 
CF.sub.3)--, 
Q.sup.2 represents oxygen, sulphur or a group from the series --CO--, 
--CS--, --CH.sub.2 --, --CHF--, --CF.sub.2 --, --CHCl--, --CHBr--, 
--CHOCHF.sub.2 --, --CHOCF.sub.3 --, --CHOCH.sub.2 CF.sub.3 --, 
R.sup.6 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, 
fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, 
difluoromethyl, trifluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- 
or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 
methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, 
trifluoromethylthio, chlorodifluoromethylthio, methylamino, ethylamino, n- 
or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl or 
ethoxycarbonyl, and 
R.sup.7 represents hydrogen, hydroxyl, amino, cyano, methyl, ethyl, n- or 
i-propyl, difluoromethyl, methoxy, ethoxy, n- or i-propoxy, 
or where optionally two adjacent groups--R.sup.6 and R.sup.6 or R.sup.7 and 
R.sup.7 or R.sup.6 and R.sup.7 -- together represent in each case 
optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or 
i-propyl-substituted alkanediyl or alkenediyl having in each case up to 4 
carbon atoms which is optionally interrupted by oxygen, sulphur or a group 
from the series --SO--, SO.sub.2 --, --N(CH.sub.3)-- or N(C.sub.2 
H.sub.5)-- at the beginning (or at the end) or within the hydrocarbon 
chain. 
The definitions of radicals listed above, indicated in general or in ranges 
of preference, apply both to the end products of the formula (I) and, 
correspondingly, to the respective starting materials and intermediates 
required for preparation. These radical definitions can be combined as 
desired with one another, which therefore includes any desired 
combinations between the indicated ranges of preferred compounds. 
Examples of the compounds of the formula (I) according to the invention are 
listed in the groups below. 
Group 1 
##STR6## 
In this formula R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated in 
the following list: 
______________________________________ 
Synthesis 
Ex. No. 
R.sup.1 
R.sup.2 R.sup.3 
______________________________________ 
1 H F H 
2 H Cl H 
3 H Cl Cl 
4 Cl F H 
5 F F H 
6 F F Cl 
7 F CH.sub.3 H 
8 F C.sub.2 H.sub.5 H 
9 F --CH.sub.2 Cl H 
10 F F F 
11 F --NHC.sub.2 H.sub.5 H 
12 F --CH.sub.2 CN H 
13 F N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
H 
14 Cl --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
H 
15 Cl --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
Cl 
16 F --NH--COCF.sub.3 H 
17 F --OH H 
18 Cl --OH H 
19 F --CH(CH.sub.3).sub.2 H 
20 F --NH--SO.sub.2 --CH.sub.3 
H 
21 F --SO.sub.2 --CH.sub.3 H 
22 F --SO.sub.2 --O--CH.sub.3 
H 
23 F --SO.sub.2 --NH--CH.sub.3 
H 
24 F --COOCH.sub.3 H 
25 F --CO--NH--CH.sub.3 H 
26 Cl --COOCH.sub.3 Cl 
27 Cl --COOC.sub.2 H.sub.5 H 
28 F --O--C.sub.2 H.sub.5 H 
29 F --N(C.sub.2 H.sub.5)SO.sub.2 C.sub.2 H.sub.5 
H 
30 F --N(SO.sub.2 CH.sub.3).sub.2 
H 
31 F --CO--N(CH.sub.3).sub.2 H 
32 F --S--CH.sub.2 --C.tbd.C--H 
H 
33 Cl --S--CH.sub.2 --C.tbd.CH 
F 
34 F --S--CH.sub.2 --C.tbd.CH 
Cl 
35 F --O--CH(CH.sub.3)--C.tbd.CH 
H 
36 F --S--CH.sub.2 --COOCH.sub.3 
H 
37 F --O--CH.sub.2 CH.sub.2 --OCH.sub.3 
H 
38 F --O(CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3 
H 
39 F --O--CH.sub.2 --CH.tbd.CH.sub.2 
H 
40 F --O--CH.sub.2 --C.tbd.CH 
H 
41 F --SH H 
42 F --S--CH.sub.3 H 
43 F --S--C.sub.2 H.sub.5 H 
44 F --S--CH(CH.sub.3).sub.2 H 
45 F --O--CH.sub.2 --CF.sub.3 
H 
46 F --O--CH(CH.sub.2 F).sub.2 
H 
47 F 
##STR7## H 
48 F 
##STR8## H 
49 F --NH--SO.sub.2 C.sub.2 H.sub.5 
H 
50 Cl --NH--SO.sub.2 C.sub.2 H.sub.5 
H 
51 F --NH--SO.sub.2 C.sub.2 H.sub.5 
Cl 
52 F --NH--SO.sub.2 CH(CH.sub.3).sub.2 
H 
53 F --NH--SO.sub.2 C.sub.4 H.sub.9 
H 
54 F --N.dbd.CH--OC.sub.2 H.sub.5 
H 
55 F --N.dbd.C(CH.sub.3)OC.sub.2 H.sub.5 
H 
56 F --N.dbd.C(OCH.sub.3).sub.2 
H 
57 F --N.dbd.CH--N(CH.sub.3).sub.2 
H 
58 F --SCN H 
59 F --SO.sub.2 Cl H 
60 F --O--CS--N(CH.sub.3).sub.2 
H 
61 F --S--CO--N(CH.sub.3).sub.2 
H 
62 F --NH--P(O)(CH.sub.3)OC.sub.2 H.sub.5 
H 
63 F --NH--P(O)(OC.sub.2 H.sub.5).sub.2 
H 
64 F --NH--COC.sub.2 H.sub.5 H 
65 F --N(CH.sub.3)COCF.sub.3 H 
66 F --NH--COCH(CH.sub.3).sub.2 
H 
67 F --NH--CO--CO--C(CH.sub.3).sub.3 
H 
68 F --NH--CO--NH.sub.2 H 
69 F NH--CO--NHCH.sub.3 H 
70 F --NH--CO--N(CH.sub.3).sub.2 
H 
71 F --N(COCH.sub.3).sub.2 H 
72 F --NH--COCH(CH.sub.3)Cl H 
73 F S--CH.sub.2 --CH.dbd.CH.sub.2 
H 
74 Cl S--CH.sub.2 --CH.dbd.CH.sub.2 
H 
75 F S--CH(CH.sub.3)C.tbd.CH H 
76 F S--CH(CH.sub.3)COOC.sub.2 H.sub.5 
H 
77 F S(O)--CH.sub.3 H 
78 F 
##STR9## H 
79 F 
##STR10## H 
80 F 
##STR11## H 
81 F 
##STR12## H 
82 F 
##STR13## H 
83 F 
##STR14## H 
84 F --O--CH.sub.2 --CN H 
85 F --O--SO.sub.2 CH.sub.3 H 
86 F --OCH.sub.2 --CH(Cl).dbd.CH.sub.2 
H 
87 F --O--CH.sub.2 --COOCH.sub.3 
H 
88 F --O--CHF.sub.2 H 
89 F --OCOOCH.sub.2 CH.sub.2 Cl 
H 
90 F --OCH.sub.2 P(O)(OC.sub.2 H.sub.5).sub.2 
H 
91 Cl --O--CH(CH.sub.3)P(O)(OC.sub.2 H.sub.5).sub.2 
H 
92 F 
##STR15## H 
93 F 
##STR16## H 
94 F --O--N(C.sub.2 H.sub.5).sub.2 
H 
95 F 
##STR17## H 
96 F 
##STR18## H 
97 F 
##STR19## Cl 
98 Cl 
##STR20## H 
99 F 
##STR21## F 
100 F 
##STR22## H 
101 F 
##STR23## H 
102 F 
##STR24## H 
103 F --NCH(CH.sub.3).sub.2 SO.sub.2 C.sub.2 H.sub.5 
H 
104 F --N(CH.sub.3)SO.sub.2 CH(CH.sub.3).sub.2 
H 
105 H --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
Cl 
106 Cl --N(CH.sub.3)SO.sub.2 C.sub.4 H.sub.9 
H 
107 F --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
H 
108 F --N(CH.sub.3)SO.sub.2 CH.sub.3 
H 
109 F --N(SO.sub.2 C.sub.2 H.sub.5).sub.2 
H 
110 F --N(SO.sub.2 CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 
H 
111 F 
##STR25## H 
112 F --N(CH.sub.3).sub.2 H 
113 F --NH.sub.2 H 
114 Cl --NH.sub.2 H 
115 Cl --O--CH(CH.sub.3).sub.2 H 
116 F --O--CH(CH.sub.3).sub.2 H 
117 F 
##STR26## H 
118 Cl 
##STR27## H 
119 F --O--CH.sub.2 --COOC.sub.2 H.sub.5 
H 
120 F --S--CH.sub.2 --COOCH.sub.3 
H 
121 F --S--CH.sub.2 --COOC.sub.2 H.sub.5 
H 
122 Cl --S--CH.sub.2 --COOC.sub.2 H.sub.5 
H 
123 F --CH.sub.2 --CH(Cl)COOCH.sub.3 
H 
124 F --CH.sub.2 --CH(Cl)COOC.sub.2 H.sub.5 
H 
125 F --CH.sub.2 --CH(Cl)CONHC.sub.2 H.sub.5 
H 
126 Cl --CH.sub.2 --CH(Cl)CONHC.sub.2 H.sub.5 
H 
127 Cl 
##STR28## H 
128 F 
##STR29## H 
129 F --COOC.sub.3 H.sub.7 -i H 
Group 2 
(IA-2) 
##STR30## 
______________________________________ 
In this formula R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 3 
##STR31## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 4 
##STR32## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 5 
##STR33## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 6 
##STR34## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 7 
##STR35## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 8 
##STR36## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 9 
##STR37## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 10 
##STR38## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 11 
##STR39## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 12 
##STR40## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 13 
##STR41## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 14 
##STR42## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 15 
##STR43## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 16 
##STR44## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 17 
##STR45## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 18 
##STR46## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 19 
##STR47## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 20 
##STR48## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 21 
##STR49## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 22 
##STR50## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 23 
##STR51## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 24 
##STR52## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 25 
##STR53## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 26 
##STR54## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 27 
##STR55## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 28 
##STR56## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 29 
##STR57## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 30 
##STR58## 
In this formula, Rx, R.sup.2 and R.sup.3 have, for example, the meanings 
indicated above in Group 1. 
Group 31 
##STR59## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 32 
##STR60## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 33 
##STR61## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 34 
##STR62## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 35 
##STR63## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 36 
##STR64## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 37 
##STR65## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 38 
##STR66## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 39 
##STR67## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 40 
##STR68## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 41 
##STR69## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 42 
##STR70## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 43 
##STR71## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 44 
##STR72## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 45 
##STR73## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in. Group 1. 
Group 46 
##STR74## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 47 
##STR75## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 48 
##STR76## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 49 
##STR77## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 50 
##STR78## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 51 
##STR79## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 52 
##STR80## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 53 
##STR81## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 54 
##STR82## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 55 
##STR83## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 56 
##STR84## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 57 
##STR85## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 58 
##STR86## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 59 
##STR87## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 60 
##STR88## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 61 
##STR89## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 62 
##STR90## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 63 
##STR91## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 64 
##STR92## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 65 
##STR93## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 66 
##STR94## 
Group 67 
##STR95## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 68 
##STR96## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 69 
##STR97## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 70 
##STR98## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 71 
##STR99## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 72 
##STR100## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 73 
##STR101## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 74 
##STR102## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 75 
##STR103## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 76 
##STR104## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 77 
##STR105## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 78 
##STR106## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 79 
##STR107## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Table 80 
##STR108## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 81 
##STR109## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 82 
##STR110## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 83 
##STR111## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 84 
##STR112## 
In this formula, R.sup.1, R.sup.2 and R.sup.3 have, for example, the 
meanings indicated above in Group 1. 
Group 85 
##STR113## 
In this formula, R.sup.1, R.sup.4 and R.sup.5 have the meanings indicated 
in the following list: 
______________________________________ 
Ex. No. R.sup.1 R.sup.4 R.sup.5 
______________________________________ 
1 F CH.sub.3 CH.sub.3 
2 Cl CH.sub.3 CH.sub.3 
3 H CH.sub.3 CH.sub.3 
4 F Cl CH.sub.3 
5 F Cl Cl 
6 F C.sub.2 H.sub.5 
CH.sub.3 
______________________________________ 
Group 86 
##STR114## 
In this formula R.sup.1, R.sup.4 and R.sup.5 have, for example, the 
meanings indicated above in Group 85. 
Group 87 
##STR115## 
In this formula, R.sup.1, R.sup.4 and R.sup.5 have, for example, the 
meanings indicated above in Group 85. 
Group 88 
##STR116## 
In this formula, R.sup.1, R.sup.4 and R.sup.5 have, for example, the 
meanings indicated above in Group 85. 
Group 89 
##STR117## 
In this formula, R.sup.1, R.sup.4 and R.sup.5 have, for example, the 
meanings indicated above in Group 85. 
Using, for example, 
2-(2-fluoro-4-cyano-5-methoxy-phenyl)4-methyl-5-difluoromethyl-2,4-dihydro 
-3H-1,2,4-triazol-3-one and hydrogen sulphide as starting materials, the 
course of reaction of the process according to the invention can be 
illustrated by the following equation: 
##STR118## 
A general definition of the substituted aromatic nitriles to be used as 
starting materials in the process according to the invention for the 
preparation of the compounds of the general formula (I) is given by the 
formula (II). In the formula (II), R.sup.1, R.sup.2, R.sup.3 and Z 
preferably or in particular have those meanings which have already been 
indicated above, in connection with the description of the compounds of 
the formula (1), as preferred or, respectively, as particularly preferred 
for R.sup.1, R.sup.2, R.sup.3 and Z. 
The starting materials of the formula (II) are known and/or can be prepared 
by known processes (cf. EP-A 370332; DE-A 4238125; DE-A 4303376; U.S. Pat. 
No. 5,084,084; Preparation Examples). 
Suitable diluents for carrying out the process according to the invention 
are the customary organic solvents. These include, in particular, 
aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, for 
example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, 
petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, 
tetrachloromethane; ethers, such as diethyl ether, diisopropyl ether, 
dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; 
ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, 
such as acetonitrile, propionitrile or benzonitrile; amides, such as 
N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, 
N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as 
methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, 
azines, such as pyridine, 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. 
The process according to the invention is preferably carried out in the 
presence of a suitable reaction auxiliary. Suitable such auxiliaries are 
all customary inorganic or organic bases. These include, for example, 
alkaline earth metal or alkali metal hydrides, hydroxides, amides, 
alcoholates, acetates, carbonates or hydrogen carbonates, for example 
sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium 
tert-butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, 
sodium acetate, potassium acetate, calcium acetate, ammonium acetate, 
sodium carbonate, potassium carbonate, potassium hydrogen carbonate, 
sodium hydrogen carbonate or ammonium carbonate and also basic organic 
nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, 
N,N-dimethylaniline, pyridine, N-methylpiperidine, 
N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene 
(DBN) or diazabicycloundecene (DBU). 
The reaction temperatures when carrying out the process according to the 
invention can be varied within a relatively large range. It is generally 
carried out at temperatures between 0.degree. C. and 100.degree. C., 
preferably at temperatures between 10.degree. C. and 80.degree. C. 
The process according to the invention is generally carried out under 
atmospheric pressure. However, it is also possible to operate under 
elevated or reduced pressure, generally between 0.1 bar and 10 bar. 
To carry out the process according to the invention the starting materials 
of the formula (II) are introduced, generally in a suitable diluent in the 
presence of a reaction auxiliary, and the hydrogen sulphide or the 
thioacetamide is slowly metered in. The hydrogen sulphide or the 
thioacetamide are preferably employed in a relatively large excess. The 
reaction mixture is stirred for a number of hours at the particular 
temperature required. Working up in the process according to the invention 
is effected in each case in accordance with customary methods (cf. the 
Preparation Examples). 
The active compounds according to the invention can be used as defoliants, 
desiccants, haulm killers and, especially, as weedkillers. By weeds, in 
the broadest sense, there are to be understood all plants which grow in 
locations where they are not wanted. Whether the substances according to 
the invention act as total or selective herbicides depends essentially on 
the amount used. 
The active compounds according to the invention can be used, for example, 
in connection with the following plants: 
Dicotyledon 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, Lindemia, Lamium, 
Veronica, Abutilon, Emex, Datum, Viola, Galeopsis, Papaver, Centaurea, 
Trifolium, Ranunculus and Taraxacum. 
Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus, 
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, 
Arachis, Brassica, Lactuca, Cucumis and Cucurbita. 
Monocotyledon 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 and Apera. 
Monocotyledon cross of the genera: Oryza, Zea, Triticum, Hordeum, Avena, 
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. 
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. 
Depending on the concentration, the compounds are suitable for total weed 
control, for example on industrial terrain and rail tracks, and on paths 
and areas with or without tree stands. Equally, the compounds 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 hopfields, in lawns, turf and pastures, and for selective weed control 
in annual crops. 
The compounds of the formula (I) according to the invention are 
particularly suitable for selective control of monocotyledon and 
dicotyledon weeds in monocotyledon and dicotyledon crops, both pre- and 
post-emergence. 
To a certain extent, the compounds of the formula (1) also show a 
fungicidal action, for example against Pyricularia oryzae in rice. 
The active compounds can be converted into the customary formulations, such 
as solutions, emulsions, wettable powders, suspensions, powders, dusts, 
pastes, soluble powders, granules, suspoemulsion concentrates, natural and 
synthetic materials impregnated with active compound, and 
microencapsulations in polymeric substances. 
These formulations are produced in a known manner, for example by mixing 
the active compounds with extenders, that is liquid solvents and/or solid 
carriers, optionally with the use of surfactants, that is emulsifiers 
and/or dispersants and/or foam-formers. 
If water is used as an extender, organic solvents can, for example, also be 
used 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 as well as their ethers 
and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl 
ketone or cyclohexanone, strongly polar solvents such as dimethylformamide 
and dimethyl sulphoxide, and water. 
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 highly disperse silica, alumina and silicates; suitable solid carriers 
for granules are: for example crushed and fractionated natural rocks such 
as calcite, marble, pumice, sepiolite and dolomite, or else 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 non-ionic and anionic 
emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene 
fatty alcohol ethers, for example alkylaryl polyglycol ethers, 
alkylsulphonates, alkyl sulphates, arylsulphonates and protein 
hydrolysates; suitable dispersants are: for example lignin-sulphite waste 
liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latexes such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, or else natural phospholipids such as 
cephalins and lecithins, and synthetic phospholipids can be used in the 
formulations. Further additives can be mineral and vegetable oils. 
It is possible to use colourants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyes such as 
alizarin dyes, axo dyes and metal phthalocyanine dyes, and trace nutrients 
such as salts of iron, manganese, boron, copper, cobalt, molybdenum and 
zinc. 
The formulations generally comprise between 0.1 and 95 per cent by weight 
of active compound, preferably between 0.5 and 90%. 
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. 
Possible components for the mixtures are known herbicides, examples being 
anilides, for example, diflufenican and propanil; arylcarboxylic acids, 
for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic 
acids, for example 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and 
triclopyr, aryloxy-phenoxy-alkanoic esters, for example diclofop(-methyl), 
fenoxaprop(-ethyl), fluazifop(-butyl), haloxyfop(-methyl) and 
quizalofop(-ethyl); azinones, for example chloridazon and norflurazon; 
carabamates, for example chlorpropham, desmedipham, phenmaedipham and 
propham; chloroacetanilides, for example alachlor, acetochlor, butachlor, 
metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, 
for example oryzalin, pendimethalin and trifluralin; diphenyl ethers, for 
example acifluorfen, bifenox, chlormethoxynil (X-52), chlornitrofen, 
fluoroglycofen, fomesafen, halosafen, lactofen, nitrofen and oxyfluorfen; 
ureas, for example chlortoluron, cumyluron (JC-940), diuron, dymron 
(daimuron), fluormeturon, isoproturon, linuron and methabenzthiazuron; 
hyroxylamines, for example alloxydim, clethodim, cycloxydim, sethoxydim 
and tralkoxydim; imidazolinones, for example imazethapyr, imazamethabenz, 
imazapyr and imazaquin; nitriles, for example bromoxynil, dichlobenil and 
ioxynil; oxyacetamides, for example mefenacet; sulphonylureas, for example 
AC-014 (AC-322140), amidosulfuron, bensulfuron(-methyl), 
chlorimuron(-ethyl), chlorsulfuron, cinosulfuron, DPX-47, HOE-404, 
imazosulfuron, metsulfuron(-methyl), nicosulfuron, primisulfuron, 
pyrazosulfuron(-ethyl), thifensulfuron(-methyl), triasulfuron and 
tribenuron(-methyl); thiocarbamates, for example butylate, cycloate, dial 
late, dimepiperate, EPTC, esprocarb, molinate, prosulphocarb, thiobencarb 
(benthiocarb) and triallate; triazines, for example atrazine, cyanazine, 
dimethametryn, prometryne, simazin, simetryne, terbutryne and 
terbutylazin; triazinones, for example hexazinon, metamitron and 
metribuzin; others, for example aminotriazole, benfuresate, bensulide, 
bentazone, benzofenap, bromobutide, butamifos, cafenstrole (CH-900), 
cinmethylin, clomazone, clomeprop, clopyralid, DEH-112, difenzoquat, 
dimethenamid, dithiopyr, ethofumesate, flumetsulam, fluorochloridone, 
glufosinate, glyphosate, amiprophos(-methyl), anilofos, etobenzanid 
(HW-52), isoxaben, KPP-314, KUH-833, KUH-911, KUH-920, MK-243, 
naproanilide, NSK-850, oxadiazon, piperophos, propanil, pyrazolate, 
pyrazoxyfen, pyributicarb, pyridate, quinchlorac, quinmerac, sulphosate 
and tridiphane. 
Mixtures with other known active compounds, such as fungicides, 
insecticides, caricides, nematicides, bird repellants, plant nutrients and 
soil conditioners, are also possible. 
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 or spreading. 
The active compounds according to the invention can be applied either 
before or after emergence of the plants. They can also be incorporated 
into the soil before sowing. 
The amount of active compound used can vary within a substantial range. It 
depends essentially on the nature of the desired effect. In general, the 
amounts used are between 10 g and 10 kg of active compound per hectare of 
soil surface, preferably between 50 g and 5 kg per ha. 
The preparation and use of the active compounds according to the invention 
can be seen from the examples which follow.