Substituted sulphonylamino(thio)carbonyl compounds

Abstract

The invention relates to novel substituted sulphonylamino(thio)carbonyl compounds of the formula (I) in which A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N—, or —N═CH— or —CH═CH—, Q represents oxygen or sulphur, R 1 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, R 2 represents cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and R 3 represents respectively optionally substituted heterocyclyl having 5 ring members of which at least one represents oxygen, sulphur or nitrogen and a further one to three may represent nitrogen (except for certain individual prior art compounds), furthermore to salts of novel compounds of the formula (I), to various processes and novel intermediates for preparing the novel compounds and to their use as herbicides.

1 . Substituted sulphonylamino(thio)carbonyl compounds of the general formula (I),  
       
         
           
           
               
               
           
         
       
       in which 
 A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N—, or —N═CH— or —CH═CH—,  
 Q represents oxygen or sulphur,  
 R 1  represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,  
 R 2  represents cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and  
 R 3  represents respectively optionally substituted heterocyclyl having 5 ring members of which at least one represents oxygen, sulphur or nitrogen and a further one to three may represent nitrogen,  
 and salts of compounds of the formula (I),  
 except for the compounds N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-ethyl-oxazole-4-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide, N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-methyl-isoxazole-4-carboxamide and N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide.  
 
     
     
         2 . Compounds of the formula (I) according to  claim 1 , characterized in that 
 A represents oxygen, sulphur, NH, N-C 1 -C 4 -alkyl, N-phenyl, —CH═N— or —N═CH— or —CH═CH—,    Q represents oxygen or sulphur,    R 1  represents optionally cyano-, nitro-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, represents respectively optionally cyano- or halogen-substituted C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl, represents respectively optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, represents respectively optionally cyano-, nitro-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -halogenoalkoxy-substituted phenyl or phenyl-C 1 -C 4 -alkyl, or represents respectively optionally cyano-, nitro-, halogen-, C 1  -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1  -C 4 -alkoxy- or C 1 -C 4 -halogenoalkoxy-substituted heterocyclyl or heterocyclyl-C 1 -C 4 -alkyl, where in each case the heterocyclyl group is selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl,    R 2  represents cyano, nitro, halogen, represents respectively optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl, or represents respectively optionally cyano- or halogen-substituted C 2 -C 4 -alkenyl, C 2 -C 4 -alkinyl, C 2 -C 4 -alkenyloxy or C 2 -C 4 -alkinyloxy, and    R 3  represents respectively optionally substituted heterocyclyl of the formulae below,                          in which    Q 1 , Q 2  and Q 3  each represent oxygen or sulphur and    R 4  represents hydrogen, hydroxyl, amino, cyano, represents C 2 -C 10 -alkylidene-amino, represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkyl, represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl, represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino or C 1 -C 6 -alkyl-carbonyl-amino, represents C 3 -C 6 -alkenyloxy, represents di-(C 1 -C 4 -alkyl)-amino, represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-amino or C 3 -C 6 -cycloalkyl-CI-C 4 -alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl- and/or C 1 -C 4 -alkoxy-substituted phenyl or phenyl-C 1 -C 4 -alkyl,    R 5  represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkyl, represents espectively optionally fluorine-, chlorine- and/or bromine-substituted C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl, represents respectively optionally fluorine-, chlorine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or C 1 -C 6 -alkyl-carbonylamino, represents C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkinylthio, C 3 -C 6 -alkenylamino or C 3 -C 6 -alkinylamino, represents di-(C 1 -C 4 -alkyl)-amino, represents respectively optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio, C 3 -C 6 -cycloalkylamino, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkylthio or C 3  -C6-cycloalkyl-C 1 -C 4 -alkylamino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl-, C 1 -C 4 -alkoxy- and/or C 1 -C 4 -alkoxy-carbonyl-substituted phenyl, phenyl-C 1 -C 4 -alkyl, phenoxy, phenyl-C 1 -C 4 -alkoxy, phenylthio, phenyl-C 1 -C 4 -alkylthio, phenylamino or phenyl-C 1 -C 4 -alkylamino, or    R 4  and R 5  together represent optionally branched alkanediyl having 3 to 11 carbon atoms, furthermore    R 6 , R 7  and R 8  are identical or different and each represents hydrogen, cyano, fluorine, chlorine, bromine, or represents respectively optionally fluorine-, chlorine-, bromine- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms or represent optionally cyano-, fluorine-, chlorine-, bromine- or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,    and the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkyl-ammonium, di-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C4-alkyl)-ammonium, tetra-(C 1 -C 4 -alkyl)-ammonium, tri-(CI-C4-alkyl)-sulphonium, C 5 - or C 6 -cycloalkyl-ammonium and di-(C 1 -C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I),    except for the individual compounds mentioned in  claim 1 .    
     
     
         3 . Compounds of the formula (I) according to  claim 1 , characterized in that 
 A represents sulphur, N-methyl, —CH═N— or —N═CH— or —CH═CH—,    Q represents oxygen or sulphur,    R 1  represents respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents respectively optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents respectively optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclo-hexylmethyl, represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, methoxy- or ethoxy-substituted heterocyclyl or heterocyclyl-methyl, where in each case the heterocyclyl group is selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,    R 2  represents cyano, fluorine, chlorine, bromine, represents respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represents respectively optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl, butinyl, propenyloxy or propinyloxy, and    R 3  represents respectively optionally substituted heterocyclyl of the formulae below,                          in which    Q 1 , Q 2  and Q 3  each represent oxygen or sulphur and    R 4  represents hydrogen, hydroxyl, amino, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,    R 5  represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, represents dimethylamino, diethylamino or dipropylamino, represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentyl-methylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexyl-methylamino, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl-, methoxy- and/or methoxy-carbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or    R 4  and R 5  together represent optionally branched alkanediyl having 3 to 11 carbon atoms, furthermore    R 6 , R 7  and R 8  are identical or different and each represents hydrogen, cyano, fluorine, chlorine, bromine, or represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represents cyclopropyl, except for the individual compounds mentioned in  claim 1 .    
     
     
         4 . Compounds of the formula (I) according to  claim 1 , characterized in that 
 A represents sulphur or —CH═CH—,    Q represents oxygen or sulphur,    R 1  represents methyl, ethyl, n- or i-propyl, 2-cyano-ethyl, 2-fluoro-ethyl, 2,2-difluoro-ethyl, 2,2,2-trifluoro-ethyl, 2-chloro-ethyl, 2,2-dichloro-ethyl, 2,2,2-trichloro-ethyl, 2-methoxy-ethyl, 2-ethoxy-ethyl or oxetanyl,    R 2  represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy or trifluoroethoxy, and    R 3  represents optionally substituted triazolinyl of the formula below                          in which    Q 1  represents oxygen or sulphur and    R 4  represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, represents respectively optionally fluorine- or chlorine-subsituted propenyl or propinyl, represents methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, represents propenyloxy, represents dimethylamino or represents cyclopropyl,    R 5  represents chlorine or bromine, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-subsituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, represents dimethylamino, diethylamino or dipropylamino, represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentyl-methylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexyl-methylamino, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl-, methoxy- and/or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or    R 4  and R 5  together represent optionally branched alkanediyl having 3 to 11 carbon atoms.    
     
     
         5 . Process for preparing compounds of the formula (I) according to  claim 1 , characterized in that 
 (a) sulphonarnides of the general formula (II)                          in which    A, R 1  and R 2  are each as defined in  claim 1 , are reacted with (thio)carboxylic acid derivatives of the general formula (III)                          in which    Q and R 3  are each as defined in  claim 1  and    Z represents halogen, alkoxy, aryloxy or arylalkoxy,    if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,    or in that    (b) sulphonyl iso(thio)cyanates of the general formula (IV)                          in which    A, Q, R 1  and R 2  are each as defined above,    are reacted with heterocycles of the general formula (V)   H—R 3   (V)   in which    R 3  is as defined above,    if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,    or in that    (c) sulphonyl chlorides of the general formula (VI)                          in which    A, R 1  and R 2  are each as defined above,    are reacted with heterocycles of the general formula (V)   H—R 3   (V)   in which    R 3  is as defined above,    and metal (thio)cyanates of the general formula (VII)   MQCN  (VII)   in which    Q is as defined above,    if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,    or in that    (d) sulphonyl chlorides of the general formula (VI)                          in which    A, R 1  and R 2  are each as defined above,    are reacted with (thio)carboxamides of the general formula (VIII)                          in which    Q and R 3  are each as defined above,    if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,    or in that    (e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)                          in which    A, Q, R 1  and R 2  are each as defined above and    Z represents halogen, alkoxy, aryloXy or arylalkoxy,    are reacted with heterocycles of the general formula (V)   H—R 3   (V)   in which    R 3  is as defined above,    if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,    and the compounds of the formula (I) obtained by processes (a), (b), (c), (d) or (e) are, if desired, converted into salts by customary methods.    
     
     
         6 . Herbicidal composition, characterized in that it contains at least one compound of the formula (I) or a salt thereof according to  claim 1 .  
     
     
         7 . The use of compounds of the general formula (I) or of salts thereof according to claim I for controlling unwanted vegetation.  
     
     
         8 . Process for controlling weeds, characterized in that compounds of the general formula (I) or salts thereof according to  claim 1  are allowed to act on the weeds or their habitat.  
     
     
         9 . Method for preparing herbical compositions, characterized in that compounds of the general formula (I) or salts thereof according to  claim 1  are mixed with extenders and/or surfactants.  
     
     
         10 . Sulphonamides of the formula (IIa) and sulphonyl chlorides of the formula (VIa)  
       
         
           
           
               
               
           
         
       
       in which in each case 
 R 1  represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl and  
 R 2  represents cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy.