N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and use thereof as herbicides
View Patent ↗N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and use thereof as herbicides N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides of the general formula (I) are described as herbicides. In this formula (I), X, Y, Z and R represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A and B represent N and CY.
1. An N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamide of formula (I) and/or a salt thereof
in which
A represents N or CY,
B represents N or CH,
X represents nitro, halogen, cyano, formyl, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P(O)(OR 5 ) 2 , CH 2 P(O)(OR 5 ) 2 , (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, where the two last-mentioned radicals are each substituted by s radicals halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl carries n oxo groups,
Y represents hydrogen, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , CO(NOR 1 )R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO2R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-CN, (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , P(O)(OR 5 ) 2 , CH 2 P(O)(OR 5 ) 2 , (C 1 -C 6 )-alkyl-phenyl, (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, thiocyanato, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 ,NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , P(O)(OR 5 ) 2 , heteroaryl, heterocyclyl or phenyl, where the three last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy and halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl carries n oxo groups, or
Z optionally represents hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkoxy if Y represents the radical S(O) n R 2 ,
R represents CH 2 R 6 , CH 2 -heterocyclyl which is substituted by m oxo groups, (C 3 -C 7 )-cycloalkyl which is substituted by t (C 1 -C 6 )-alkyl groups, or (C 2 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 2 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or halo-(C 2 -C 6 )-alkynyl, each of which is substituted by u radicals from the group consisting of nitro, cyano, hydroxy, oxo, SiR 5 3 , PO(OR 5 ) 2 , S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, N(R 3 ) 2 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl, where the radicals (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halogen, and where heterocyclyl and cycloalkyl carry n oxo groups,
Q represents O, S or NR 3 ,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 )-alkyl-heterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl, (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where the 21 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R 2 represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 )-alkyl-heterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl, (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where the 21 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R 3 represents hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl,
R 4 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl,
R 5 represents (C 1 -C 4 )-alkyl,
R 6 represents OCOOR 4 , NR 4 COOR 4 , S(O) n —(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-haloalkyl, nitro, cyano, SiR 5 3 , PO(OR 5 ) 2 , heterocyclyl or cycloalkyl, where the two last-mentioned radicals carry m oxo or hydroxy groups,
m represents 1 or 2,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3,
t represents 1, 2, 3 or 4, and
u represents 1, 2, 3, 4 or 5.
2. The N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamide and/or salt as claimed in claim 1 in which
A represents N or CY,
B represents N or CH,
X represents nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 or (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, where the two last-mentioned radicals are each substituted by s radicals halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl carries n oxo groups,
Y represents hydrogen, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , COOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 )-alkyl-phenyl, (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, thiocyanato, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , C(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , 1,2,4-triazol-1-yl, or
Z optionally represents hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkoxy if Y represents the radical S(O) n R 2 ,
R represents CH 2 R 6 , CH 2 -heterocyclyl which is substituted by m oxo groups, or (C 2 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 2 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or halo-(C 2 -C 6 )-alkynyl, each of which is substituted by u radicals from the group consisting of nitro, cyano, hydroxy, oxo, SiR 5 3 , PO(OR 5 ) 2 , S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, N(R 3 ) 2 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl, where the radicals (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halogen, and where heterocyclyl and cycloalkyl carry n oxo groups,
Q represents O, S or NR 3 ,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 )-alkyl-heterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl or (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where the 16 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R 2 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkyl-heteroaryl, heterocyclyl, (C 1 C 6 )-alkyl-heterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl or (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where these radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , NR 3 SO 2 R 4 , COR 3 , OCOR 3 , NR 3 COR 3 , CO 2 R 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R 3 represents hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl,
R 4 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 5 represents methyl or ethyl,
R 6 represents OCOOR 4 , NR 4 COOR 4 , S(O) n —(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-haloalkyl, nitro, cyano, SiR 5 3 , PO(OR 5 ) 2 or heterocyclyl which carries m oxo groups,
m represents 1 or 2,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3, and
u represents 1, 2, 3, 4 or 5.
3. The N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamide and/or salt thereof as claimed in claim 1 in which
A represents N or CY,
B represents N or CH,
X represents nitro, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, where the two last-mentioned radicals are each substituted by s radicals halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl carries n oxo groups,
Y represents hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, OR 1 , S(O) n R 2 , SO 2 N(R 1 ) 2 , N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 )-alkyl-phenyl, (C 1 -C 6 )-alkyl-heteroaryl, (C 1 -C 6 )-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Z represents halogen, cyano, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n R 2 , 1,2,4-triazol-1-yl, or Z optionally represents hydrogen, methyl, methoxy or ethoxy if Y represents the radical S(O) n R 2 ,
R represents CH 2 R 6 , CH 2 -heterocyclyl, where heterocyclyl carries m oxo groups, or (C 2 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 2 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or halo-(C 2 -C 6 )-alkynyl, each of which is substituted by u radicals from the group consisting of nitro, cyano, hydroxy, oxo, SiR 5 3 , PO(OR 5 ) 2 , S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, N(R 3 ) 2 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl, where the radicals (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halogen, and where heterocyclyl and cycloalkyl carry n oxo groups,
Q represents O, S or NR 3 ,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 )-alkyl-heterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl or (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where the 16 last-mentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R 2 represents (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three radicals mentioned above are each substituted by s radicals from the group consisting of halogen and OR 3 ,
R 3 represents hydrogen or (C 1 -C 6 )-alkyl,
R 4 represents (C 1 -C 6 )-alkyl,
R 5 represents methyl or ethyl,
R 6 represents OCOOR 4 , NR 4 COOR 4 , S(O) n —(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-haloalkyl, nitro, cyano, SiR 5 3 , PO(OR 5 ) 2 ,
m represents 1 or 2,
n represents 0, 1 or 2,
s represents 0, 1, 2 or 3, and
u represents 1, 2, 3, 4 or 5.
4. A herbicidal composition comprising a herbicidally effective amount of at least one compound as claimed in claim 1 .
5. The herbicidal composition as claimed in claim 4 in a mixture with at least one formulation auxiliary.
6. The herbicidal composition as claimed in claim 4 , comprising at least one further pesticidally active compound selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.
7. The herbicidal composition as claimed in claim 6 , comprising a safener.
8. The herbicidal composition as claimed in claim 7 , comprising cyprosulfamid, cloquintocet-mexyl, mefenpyr-diethyl and/or isoxadifen-ethyl.
9. The herbicidal composition as claimed in claim 6 , comprising a further herbicide.
10. A method for controlling unwanted vegetation, comprising applying an effective amount of at least one compound as claimed in claim 1 to a plant and/or a site of unwanted vegetation.
11. A compound as claimed in claim 1 capable of being used for controlling an unwanted plant.
12. A compound as claimed in claim 11 , wherein the compound is capable of being used for controlling an unwanted plant in a crop of a useful plant.
13. A compound as claimed in claim 12 , wherein the useful plant comprises a transgenic useful plant.
14. A method for controlling unwanted vegetation, comprising applying an effective amount of a herbicidal composition as claimed in claim 4 to a plant and/or site of unwanted vegetation.
15. A herbicidal composition as claimed in claim 4 , capable of being used for controlling an unwanted plant.