N-(1,2,5-oxadiazol-3-yl)-, n-(1,3,4-oxadiazol-2-yl)-, n-(tetrazol-5-yl)-, and n-(triazol-5-yl) aryl carboxylic acid amides and use thereof as herbicides

An N-(1,2,5-oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamide of formula (I) and/or a salt thereof

• in which
• R is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-halocycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-COOR1, (C1-C6)-alkyl-C(O)R1, (C1-C6)-alkyl-CN, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, OR1, COOR1, CON(R1)2, N(R1)2, NR1COOR1NR1CON(R1)2 or
• benzyl in each case substituted by s radicals from the group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,
• W is N or CY,
• X and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-halocycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl-(C1-C6)-alkyl, COR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-COOR1, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, NR1R2, P(O)(OR5)2, or
• heteroaryl, heterocyclyl or phenyl each substituted by s radicals from the group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,
• Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)N(R1)OR1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (C1-C6)-alkyl-S(O)nR2, (C1-C6)-alkyl-OR1, (C1-C6)-alkyl-OCOR1, (C1-C6)-alkyl-OSO2R2, (C1-C6)-alkyl-CO2R1, (C1-C6)-alkyl-CN, (C1-C6)-alkyl-SO2OR1, (C1-C6)-alkyl-CON(R1)2, (C1-C6)-alkyl-SO2N(R1)2, (C1-C6)-alkyl-NR1COR1, (C1-C6)-alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, CH═NOR1, (C1-C6)-alkyl-CH═NOR1, (C1-C6)-alkyl-O—N═C(R1)2, (C1-C6)-alkylphenyl, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 latter radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
• or
• Y and Z together with the two atoms to which they are bonded form a 5-, 6- or 7-membered, unsaturated, partly saturated or saturated ring which, as well as carbon atoms, in each case has s nitrogen atoms, n oxygen atoms, n sulfur atoms and n S(O), S(O)2, C═N—R17, C(OR17)2, C[—O—(CH2)2—O—] or C(O) elements as ring members,
• wherein the carbon atoms are substituted by s radicals from the group consisting of halogen, cyano, (C1-C6)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, phenoxy, halo-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C2-C8)-alkoxyalkyl and phenyl,
• wherein the nitrogen atoms are substituted by n radicals from the group consisting of (C1-C6)-alkyl and phenyl,
• and in which the aforementioned phenyl radicals are substituted by s radicals from the group consisting of cyano, nitro, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and (C1-C6)-alkoxy,
• V is hydrogen, nitro, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, OR1, S(O)nR2,
• R1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocycl, (C1—CO-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl, (C1-C6)-alkyl-NR3-heterocyclyl, where the 21 latter radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
• R2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1—CO-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR3-heteroaryl, (C1-C6)-alkyl-NR3-heterocyclyl, where the 21 latter radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
• R3 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
• R4 is (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
• R5 is (C1-C4)-alkyl,
• n is 0, 1 or 2;
• s is 0, 1, 2 or 3,
• Q is a Q1, Q2, Q3 or Q4 radical,
• R6 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl,
• where these 6 aforementioned radicals are each substituted by s radicals from the group consisting of nitro, cyano, SiR123, PO(OR12)3, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, N(R10)2, COR10, COOR10, OCOR10, OCO2R10, NR10COR10, NR10SO2R11, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl or D-benzyl, and where the 7 latter radicals are substituted by s radicals from the group of methyl, ethyl, methoxy, trifluoromethyl and halogen, and where heterocyclyl bears n oxo groups,
• or
• R6 is (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl,
• R7 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl,
• where these 6 aforementioned radicals are each substituted by s radicals from the group consisting of nitro, cyano, SiR123, PO(OR12)3, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, N(R10)2, COR10, COOR10, OCOR10, OCO2R10, NR10COR10, NR10SO2R11, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl and D-benzyl, and where the 7 latter radicals are substituted by s radicals from the group of methyl, ethyl, methoxy, trifluoromethyl and halogen, and where heterocyclyl bears n oxo groups,
• R7 is (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl,
• R8 is hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-alkynyloxy, halo-(C2-C6)-alkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C1-C6)-alkylcarbonylamino, (C1-C6-alkoxycarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;
• R9 is hydrogen, (C1-C6)-alkyl, R13O—(C1-C6)-alkyl, CH2R14, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, OR13, NHR13, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or heteroaryl, heterocyclyl, benzyl or phenyl, each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O)n—(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl,
• R10 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl,
• R11 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or phenyl,
• R12 is (C1-C6)-alkyl,
• R13 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR15-heteroaryl or (C1-C6)-alkyl-NR15-heterocyclyl, where the 21 latter radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR15, S(O)nR16, N(R15)2, NR15OR15, COR15, OCOR15, SCOR16, NR15COR15, NR15SO2R16, CO2R15, COSR16, CON(R15)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
• R14 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C3-C6)-alkoxy, (C3-C6)-cycloalkyl, or heteroaryl, heterocyclyl or phenyl, each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;
• R15 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
• R16 is (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl,
• R17 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy,
• s is 0, 1, 2 or 3,
• n is 0, 1 or 2;
• D is O, S, or NR11,
• excluding the compounds 2-methoxy-N-methyl-N-(1H-tetrazol-5-yl)benzamide, 2-hydroxy-N-methyl-N-(1H-tetrazol-5-yl)benzamide, 2-methoxy-N-methyl-N-(1-methyl-1H-tetrazol-5-yl)benzamide, 2-methoxy-N-(2-methyl-2H-tetrazol-5-yl)benzamide, N-methyl-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide and 3-bromo-4-methoxy-N-methyl-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide.