Herbicidal sulphonylamino(thio) carbonyl compounds

Abstract

The invention relates to novel sulphonylamino(thio) carbonyl compounds of the formula (I), in which A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl, Q represents oxygen or sulphur, R 1 represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl, R 2 represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and R 3 represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen, and salts of compounds of the formula (I), the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer; and also to processes and novel intermediates for the preparation of the novel substances and to their use as herbicides.

1. A compound of the formula (I), 
                 
 
       wherein
 A represents a single bond,  
 Q represents oxygen or sulphur,  
 R 1  represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-carbonyl or C 3 -C 6 -cycloalkyl-sulphonyl,  
 R 2  represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C 1 -C 4 -alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and  
 R 3  represents in each case optionally substituted heterocyclyl of the formula below, 
                 
 
  in which 
 Q 1  represents oxygen or sulphur, and  
 R 4  represents hydrogen, or amino, or represents C 2 -C 10 -alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted C 1 -C 6   C 6  alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C 2 - 6   C 2   -C   6 -alkenyl or C 2 - 6   C 2   -C   6 -alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, 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-carbonylamino, or represents C 3 -C 6 -alkenyloxy, or represents di-(C 1 -C 6 -alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylamino or C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl,  
 R 5  represents hydrogen, or represents optionally fluoro-, chloro-, bromo-, 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, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl, or represents in each case optionally fluoro-, chloro-, 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, or 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, or represents di-(C 1 -C 6 -alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, 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 -C 6 -cycloalkyl-C 1 -C 4 -alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl-, C 1 -C 4 -alkoxy- and/or C 1 -C 4 -alkoxy-carbonyl-substituted phenyl, phenoxy, phenyl-C 1 -C 4 -alkoxy, phenylthio, phenyl-C 1 -C 4 -alkylthio, or  
 R 4  and R 5  together represent optionally branched alkanediyl having 3 to 11 carbon atoms,  
 
 
       or a salt of the compound of formula ( I ),  
       and with the proviso that if R 1  represents methyl then R 2  does not represent 5-methoxy and if R 1  represents ethyl then R 2  does not represent 5-ethoxy. 
     
     
       2. A compound of the formula (I), according to  claim 1 , wherein
 A represents a single bond,  
 Q represents oxygen or sulphur,  
 R 1  represents methyl, ethyl, n- or i-propyl,  
 R 2  represents chloro or methyl- , in each case in position 5 or 6- , and  
 R 3  represents optionally substituted triazolinyl of the formula below, 
                 
 
  in which 
 Q 1  represents oxygen or sulphur, and  
 R 4  represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and  
 R 5  represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl,  
 
 
       and with the proviso that if R 1  represents methyl then R 2  does not represent 5-methoxy and if R 1  represents ethyl then R 2  does not represent 5-ethoxy. 
     
     
       3. A compound of the formula (I), according to  claim 1 , wherein
 A represents a single bond,  
 Q represents oxygen or sulphur,  
 R 1  represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl,  
 R 2  represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and  
 R 3  represents in each case optionally substituted heterocyclyl of the formula below, 
                 
 
  in which 
 Q 1  represents oxygen or sulphur, and  
 R 4  represents hydrogen, or amino, or represents C 3 -C 4 -alkylideneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, 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, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,  
 R 5  represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, 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, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, 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, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy-and/or methoxy-carbonyl substituted phenoxy, benzyloxy, phenylthio, benzylthio, or  
 R 4  and R 5  together represent optionally branched alkanediyl having 3 to 11 carbon atoms,  
 
 
       with the proviso that if R 1  represents methyl then R 2  does not represent 5-methoxy and if R 1  represents ethyl then R 2  does not represent 5-ethoxy. 
     
     
       4. The compound of formula (I) according to  claim 1  wherein
 A represents a single bond,  
 Q represents oxygen,  
 R 1  represents 2,2-difluoro-ethyl,  
 R 2  represents (6-)ethyl, and  
 R 3  represents 4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-on-2-yl.  
 
     
     
       5. An herbicidal composition composing an herbicidally effective amount of a compound according to  claim 1  and an inert carrier. 
     
     
       6. A method of controlling unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation an herbicidally effective amount of a compound according to  claim 1 .