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BICYCLIC ARYLCARBOXYLIC ACID AMIDES AND THEIR USE AS HERBICIDES

20170217909 · 2017-08-03

    Inventors

    Cpc classification

    International classification

    Abstract

    Bicyclic arylcarboxamides of the general formula (I) are described as herbicides.

    ##STR00001##

    In this formula (I), Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4 and Z.sup.5 are a bond, O, S(O).sub.n or a substituted carbon atom. X is a radical such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a substituted heterocycle.

    Claims

    1. A bicyclic arylcarboxamide of the formula (I) or salt thereof ##STR00011## in which A is N or CY, X is nitro, halogen, cyano, formyl, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.1, COOR.sup.1, OCOOR.sup.1, NR.sup.1COOR.sup.1, C(O)N(R.sup.1).sub.2, NR.sup.1C(O)N(R.sup.1).sub.2, OC(O)N(R.sup.1).sub.2, C(O)NR.sup.1OR.sup.1, OR.sup.1, OCOR.sup.1, OSO.sub.2R.sup.2, S(O).sub.nR.sup.2, SO.sub.2OR.sup.1, SO.sub.2N(R.sup.1).sub.2, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl-OCOR.sup.1, (C.sub.1-C.sub.6)-alkyl-OSO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkyl-CO.sub.2R.sup.1, (C.sub.1-C.sub.6)-alkyl-SO.sub.2OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, NR.sub.1R.sub.2, P(O)(OR.sup.11).sub.2, CH.sub.2P(O)(OR.sup.11).sub.2, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, where the latter two radicals are each substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halo-(C.sub.1-C.sub.6)-alkoxy, and where heterocyclyl bears n oxo groups, Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.1, COOR.sup.1, OCOOR.sup.1, NR.sup.1COOR.sup.1, C(O)N(R.sup.1).sub.2, NR.sup.1C(O)N(R.sup.1).sub.2, OC(O)N(R.sup.1).sub.2, CO(NOR.sup.1)R.sup.1, C(NOR.sup.1)R.sup.1, NR.sup.1SO.sub.2R.sup.2, N═S(O)R.sup.2R.sup.2, NR.sup.1COR.sup.1, OR.sup.1, OSO.sub.2R.sup.2, S(O).sub.nR.sup.2, S(O)(NR.sub.2)R.sub.2, SO2OR1, SO.sub.2N(R.sup.1).sub.2 (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl- OCOR.sup.1, (C.sub.1-C.sub.6)-alkyl-OSO2R.sup.2, (C.sub.1-C.sub.6)-alkyl-CO.sub.2R.sup.1, (C.sub.1-C.sub.6)-alkyl-CN, (C.sub.1-C.sub.6)-alkyl-SO.sub.2OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, N(R.sup.1).sub.2, P(O)(OR.sup.11).sub.2, CH.sub.2P(O)(OR.sup.11).sub.2, (C.sub.1-C.sub.6)-alkylphenyl, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the latter six radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups, R.sup.1 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.1-C.sub.6)-alkylheteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkylheterocyclyl, (C.sub.1-C.sub.6)-alkyl-O-heteroaryl, (C.sub.1-C.sub.6)-alkyl-O-heterocyclyl, (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heterocyclyl, where the latter 21 radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR.sup.12, S(O).sub.nR.sup.13, N(R.sup.12).sub.2, NR.sup.12OR.sup.12, COR.sup.12, OCOR.sup.12, SCOR.sup.13, NR.sup.12COR.sup.12, NR.sup.12SO.sub.2R.sup.13, CO.sub.2R.sup.12, COSR.sup.12, CON(R.sup.12).sub.2, (C.sub.1-C.sub.6)-alkyl and (C.sub.1-C.sub.4)-alkoxy-(C.sub.2-C.sub.6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups, R.sup.2 is (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.1-C.sub.6)-alkylheteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkylheterocyclyl, (C.sub.1-C.sub.6)-alkyl-O-heteroaryl, (C.sub.1-C.sub.6)-alkyl-O-heterocyclyl, (C.sub.1-C.sub.6)-alkyl-NR.sup.3-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.3-heterocyclyl, where the latter 21 radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR.sup.12, S(O).sub.nR.sup.13, N(R.sup.12).sub.2, NR.sup.12OR.sup.13, COR.sup.12, OCOR.sup.12, SCOR.sup.13, NR.sup.12COR.sup.12, NR.sup.12SO.sub.2R.sup.13, CO.sub.2R.sup.12, COSR.sup.13, CON(R.sup.12).sub.2 and (C.sub.1-C.sub.4)-alkoxy-(C.sub.2-C.sub.6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups, Q is a Q.sup.1, Q.sup.2, Q.sup.3 or Q.sup.4 radical, ##STR00012## R.sup.3 is (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, where these radicals are each substituted by s radicals from the group consisting of halogen, cyano, hydroxyl, nitro, SiR.sup.11.sub.3, PO(OR.sup.11).sub.2, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, COR.sup.3a, COOR.sup.3a, OCOR.sup.3aNR.sup.3aCOR.sup.3a, NR.sup.3aSO.sub.2R.sup.3b, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the latter 4 radicals are each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl bears n oxo groups, or R.sup.3 is phenyl substituted by s radicals from the group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.3a is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.3b is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.4 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, 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, R.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, CH.sub.2R.sup.5a, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, methylamino, 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, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.5a is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C.sub.1-C.sub.6)-alkoxy or (C.sub.3-C.sub.6)-cycloalkyl, or heteroaryl or heterocyclyl, each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, Z.sup.1 is O, S(O).sub.n, CR.sup.6R.sup.6′ or C═W, Z.sup.2 is O, NR.sup.1, CR.sup.7R.sup.7′ or C═W, Z.sup.3 is a bond, O, CR.sup.8R.sup.8′ or C═W, Z.sup.4 is a bond, O, CR.sup.9R.sup.9′ or C═W, Z.sup.5 is O or CR.sup.10R.sup.10′, with the proviso that at least one of these Z.sup.1 to Z.sup.5 groups is a substituted carbon atom, and that two of these Z.sup.1 to Z.sup.5 groups that are directly adjacent are not both oxygen, m is 1, 2, 3 or 4, R.sup.6 and R.sup.6′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.6 and R.sup.6′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, R.sup.7 and R.sup.7′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.7 and R.sup.7′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, R.sup.8 and R.sup.8′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.8 and R.sup.8′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, R.sup.9 and R.sup.9′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.9 and R.sup.9′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, R.sup.10 and R.sup.10′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.10 and R.sup.10′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, W is oxygen, NOR.sup.1, NNR.sup.1R.sup.1 or CR.sup.1R.sup.1, R.sup.11 is (C.sub.1-C.sub.4)-alkyl, R.sup.12 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.13 is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, n is 0, 1 or 2, s is 0, 1, 2, 3, 4 or 5.

    2. A bicyclic arylcarboxamide or salt as claimed in claim 1, in which A is N or CY, X is nitro, halogen, cyano, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.1, OR.sup.1, OCOR.sup.1, OSO.sub.2R.sup.2, S(O).sub.nR.sup.2, SO.sub.2OR.sup.1, SO.sub.2N(R.sup.1).sub.2, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl-OCOR.sup.1, (C.sub.1-C.sub.6)-alkyl-OSO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkyl-CO.sub.2R.sup.1, (C.sub.1-C.sub.6)-alkyl-SO.sub.2OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1 or (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, where the latter two radicals may each be substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halo-(C.sub.1-C.sub.6)-alkoxy, and where heterocyclyl bears n oxo groups, Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.1, OR.sup.1, COOR.sup.1, OSO.sub.2R.sup.2, S(O).sub.nR.sup.2, SO.sub.2OR.sup.1, SO.sub.2N(R.sup.1).sub.2, N(R.sup.1).sub.2, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl-OCOR.sup.1, (C.sub.1-C.sub.6)-alkyl-OSO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkyl-CO.sub.2R.sup.1, (C.sub.1-C.sub.6)-alkyl-SO.sub.2OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkylphenyl, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the latter six radicals are each substituted by s radicals from the group consisting halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups, R.sup.1 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.1-C.sub.6)-alkylheteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkylheterocyclyl, (C.sub.1-C.sub.6)-alkyl-O-heteroaryl, (C.sub.1-C.sub.6)-alkyl-O-heterocyclyl, (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heterocyclyl, where the latter sixteen radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, OR.sup.12, S(O).sub.nR.sup.13, N(R.sup.12).sub.2, NR.sup.12OR.sup.12, COR.sup.12, OCOR.sup.12, NR.sup.12COR.sup.12, NR.sup.12SO.sub.2R.sup.13, CO.sub.2R.sup.12, CON(R.sup.12).sub.2 and (C.sub.1-C.sub.4)-alkoxy-(C.sub.2-C.sub.6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups, R.sup.2 is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.1-C.sub.6)-alkylheteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkylheterocyclyl, (C.sub.1-C.sub.6)-alkyl-O-heteroaryl, (C.sub.1-C.sub.6)-alkyl-O-heterocyclyl, (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heterocyclyl, where these latter sixteen radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, OR.sup.12, S(O).sub.nR.sup.13, N(R.sup.12).sub.2, NR.sup.12OR.sup.12, NR.sup.12SO.sub.2R.sup.13, COR.sup.12, OCOR.sup.12, NR.sup.12COR.sup.12, CO.sub.2R.sup.12, CON(R.sup.12).sub.2 and (C.sub.1-C.sub.4)-alkoxy-(C.sub.2-C.sub.6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups, Q is a Q.sup.1, Q.sup.2, Q.sup.3 or Q.sup.4 radical, ##STR00013## R.sup.3 is (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, where these radicals are each substituted by s radicals from the group consisting of halogen, cyano, nitro, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the latter 4 radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl bears n oxo groups, or R.sup.3 is phenyl substituted in each case by p radicals from the group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.4 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1,2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenyl substituted in each case by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, R.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine or dimethylamino, or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen, Z.sup.1 is O, S(O).sub.n, CR.sup.6R.sup.6′ or C═W, Z.sup.2 is O, NMe or CH.sub.2, Z.sup.3 is a bond, O or CH.sub.2, Z.sup.4 is a bond, Z.sup.5 is O or CH.sub.2, with the proviso that at least one of these Z.sup.1 to Z.sup.5 groups is a substituted carbon atom, and that two of these Z.sup.1 to Z.sup.5 groups that are directly adjacent are not both oxygen, m is 1, 2, 3 or 4, R.sup.6 and R.sup.6′ are each independently hydrogen, halogen, cyano, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.6 and R.sup.6′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, W is oxygen, NO(C.sub.1-C.sub.6)-alkyl, CH.sub.2, CHMe, CMe.sub.2 R.sup.12 is hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.13 is (C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2, s is 0, 1, 2, 3, 4 or 5.

    3. A bicyclic arylcarboxamide or salt as claimed in claim 1, in which A is N or CY, X is nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, OR.sup.1, S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, where the latter two radicals are each substituted by s halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halo-(C.sub.1-C.sub.6)-alkoxy radicals, and where heterocyclyl bears n oxo groups, Y is hydrogen, nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, OR.sup.1, S(O).sub.nR.sup.2, SO.sub.2N(R.sup.1).sub.2, N(R.sup.1).sub.2, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-S(O).sub.nR.sup.2, (C.sub.1-C.sub.6)-alkyl-OR.sup.1, (C.sub.1-C.sub.6)-alkyl-CON(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-SO.sub.2N(R.sup.1).sub.2, (C.sub.1-C.sub.6)-alkyl-NR.sup.1COR.sup.1, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, (C.sub.1-C.sub.6)-alkylphenyl, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the latter six radicals are each substituted by s radicals from the group consisting halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups, R.sup.1 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.1-C.sub.6)-alkylheteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkylheterocyclyl, (C.sub.1-C.sub.6)-alkyl-O-heteroaryl, (C.sub.1-C.sub.6)-alkyl-O-heterocyclyl, (C.sub.1-C.sub.6)-alkyl-NR.sup.12-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.3-heterocyclyl, where the latter sixteen radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, OR.sup.12, S(O).sub.nR.sup.13, N(R.sup.12).sub.2, NR.sup.12OR.sup.12, COR.sup.12, OCOR.sup.12, NR.sup.12COR.sup.12, NR.sup.12SO.sub.2R.sup.13, CO.sub.2R.sup.12, CON(R.sup.12).sub.2 and (C.sub.1-C.sub.4)-alkoxy-(C.sub.2-C.sub.6)-alkoxycarbonyl, and where heterocyclyl bears n oxo groups, R.sup.2 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, each substituted by s radicals from the group consisting of halogen and OR.sup.12, Q is a Q.sup.1, Q.sup.2, Q.sup.3 or Q.sup.4 radical, ##STR00014## R.sup.3 is (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl or (C.sub.2-C.sub.8)-alkynyl, each substituted by s radicals from the group consisting of halogen, cyano, nitro, S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halo-(C.sub.1-C.sub.6)-alkoxy, R.sup.4 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1,2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenyl substituted in each case by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, R.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine or dimethylamino, or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen, Z.sup.1 is O, SO.sub.2, CR.sup.6R.sup.6′ or C═W, Z.sup.2 is O, NMe or CH.sub.2, Z.sup.3 is a bond, O or CH.sub.2, Z.sup.4 is a bond, Z.sup.5 is O or CH.sub.2, with the proviso that at least one of these Z.sup.1 to Z.sup.5 groups is a substituted carbon atom, and that two of these Z.sup.1 to Z.sup.5 groups that are directly adjacent are not both oxygen, m is 1, 2, 3 or 4, R.sup.6 and R.sup.6′ are each independently hydrogen, fluorine, hydroxyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, or R.sup.6 and R.sup.6′ form a (C.sub.2-C.sub.5)-alkylene group in which n carbon atoms may be by oxygen, W is oxygen or NO(C.sub.1-C.sub.6)-alkyl, R.sup.12 is hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.13 is (C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2, s is 0, 1, 2, 3, 4 or 5.

    4. A herbicidal composition, comprising a herbicidally active content of at least one bicyclic arylcarboxamide of the formula (I) or salt as claimed in claim 1.

    5. The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.

    6. The herbicidal composition as claimed in claim 4, comprising at least one further pesticidally active substance 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 cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

    9. A method for controlling unwanted plants, comprising applying an effective amount of at least one bicyclic arylcarboxamide of the formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to the plants or to a site of unwanted vegetation.

    10. A product comprising a bicyclic arylcarboxamide of the formula (I) or salt as claimed in claim 1 or herbicidal composition thereof for controlling unwanted plants.

    11. A product as claimed in claim 10, wherein the bicyclic arylcarboxamide of the formula (I) or salt is used for controlling unwanted plants in one or more crops of useful plants.

    12. A product as claimed in claim 11, wherein the useful plants are transgenic useful plants.

    Description

    A. CHEMICAL EXAMPLES

    Synthesis of N-(1-methyltetrazol-5-yl)-3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxamide (no. 1-36)

    Step 1: Synthesis of methyl 3-amino-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

    [0079] 11.66 g (120 mmol) of potassium thiocyanate in 120 mL of methanol under an argon atmosphere were cooled down to a temperature of −10° C. At this temperature, 7.19 g (45 mmol) of bromine were added. Subsequently, 6.16 g (30 mmol) of methyl 3-amino-5,6,7,8-tetrahydronaphthalene-2-carboxylate were added. The reaction mixture was stirred without cooling for 1.5 h and then cooled down to 0° C. After addition of 7.46 g (54 mmol) of potassium carbonate, 11.52 g (48 mmol) of sodium sulfide nonahydrate, dissolved in 40 mL of water, were added dropwise. In the course of this, the temperature increased to 7° C. The mixture was stirred while cooling with an ice bath for another 30 min and then 8.70 g (69 mmol) of dimethyl sulfate were added dropwise. After stirring at 0° C. for one hour, 5 mL of dimethylamine solution (60% in water) were added and the mixture was stirred at room temperature for a further 30 min. For workup, the mixture was poured onto 300 mL of ice-water and filtered with suction, and the precipitate was washed with 100 mL of ice-water. The residue was dried in vacuo. 7.17 g of methyl 3-amino-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate were obtained. .sup.1H-NMR (DMSO-d.sub.6): 7.53 (s, 1H), 6.74 (bs, 2H), 3.79 (s, 3H), 2.93 (t, 2H), 2.61 (t, 2H), 2.16 (s, 3H), 1.83-1.70 (m, 4H).

    Step 2: Synthesis of methyl 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

    [0080] To a mixture of 3.50 g (13.9 mmol) of methyl 3-amino-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate and 2.81 g (21 mmol) of copper(II) chloride in 110 mL of acetonitrile were added dropwise, at 70° C., 1.79 g (15 mmol) of isoamyl nitrite. Subsequently, the mixture was stirred at 80° C. for another 30 min. After cooling to RT, the mixture was diluted with ethyl acetate and washed successively with 2 N hydrochloric acid (3 x), saturated aqueous sodium hydrogencarbonate solution and sodium chloride solution. The organic phase was dried and the filtrate was freed of solvents. The residue was purified by means of LC (toluene). 3.09 g of methyl 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate were obtained. .sup.1H-NMR (DMSO-d.sub.6): 7.45 (s, 1H), 3.84 (s, 3H), 3.00 (t, 2H), 2.74 (t, 2H), 2.30 (s, 3H), 1.80-1.66 (m, 4H).

    Step 3: Synthesis of 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

    [0081] 271 mg (1 mmol) of methyl 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylate and 2 mL of 2 N sodium hydroxide solution in 3 mL of methanol were heated to 50° C. for 3 h. After cooling to RT, the mixture was acidified with 2 N hydrochloric acid, and the precipitated crystals were filtered off with suction, washed with water and dried under reduced pressure. 230 mg of 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid were obtained. .sup.1H-NMR (DMSO-d.sub.6): 7.41 (s, 1H), 2.99 (t, 2H), 2.74 (t, 2H), 2.30 (s, 3H), 1.79-1.66 (m, 4H).

    Step 4: N-(1-Methyltetrazol-5-yl)-3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxamide (no. 1-36)

    [0082] 218 mg (0.85 mmol) of 3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid and 129 mg (1.27 mmol) of 5-amino-1-methyltetrazole were dissolved in 2 mL of pyridine. Subsequently, at 0° C., 155 mg (1.27 mmol) of thionyl chloride were added dropwise. After 4 d at RT, the mixture was acidified with 2 N hydrochloric acid and taken up with ethyl acetate, the phases were separated and the organic phase was washed with saturated aqueous sodium hydrogencarbonate solution and sodium chloride solution. The organic phase was dried and the filtrate was freed of solvents. 170 mg of N-(1-methyltetrazol-5-yl)-3-chloro-4-(methylthio)-5,6,7,8-tetrahydronaphthalene-2-carboxamide were obtained.

    [0083] The examples listed in the tables below were prepared analogously to the abovementioned methods or are obtainable analogously to the abovementioned methods. The compounds listed in the tables below are very particularly preferred.

    [0084] The abbreviations used mean:

    [0085] Et=ethyl Me=methyl nPr=n-propyl cPr=cyclopropyl

    TABLE-US-00001 TABLE 1 Inventive compounds of the general formula (I) in which Q is Q.sup.1 and Z.sup.4 is a direct bond [00007]embedded image Physical data No. R.sup.3 X Y Z.sup.1 Z.sup.2 Z.sup.3 Z.sup.5 (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 1-1 Me Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-2 Et Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-3 nPr Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-4 Me Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-5 Et Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-6 Me nPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-7 Me cPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-8 Me Me SMe CH.sub.2 CH.sub.2 bond CH.sub.2 7.53 (s, 1H), 4.16 (s, 3H), 2.92-2.88 (m, 4H), 2.30 (s, 3H), 2.09 (s, 3H), 2.02-1.96 (m, 2H) 1-9 Me Me SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 7.74 (s, 1H), 4.18 (s, 3H), 3.27-2.97 (m, 2H), 2.82 (t, 2H), 2.67 (s, 3H), 2.24 (s, 3H), 2.02 (m, 2H) 1-10 Me Me SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 7.87 (s, 1H), 4.21 (s, 3H), 3.18 (t, 2H), 3.11 (s, 3H), 2.88 (t, 2H), 2.45 (s, 3H), 1.99 (m, 2H) 1-11 Me Me SEt CH.sub.2 CH.sub.2 bond CH.sub.2 1-12 Me Me SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 1-13 Me Me SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 1-14 Me Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-15 Et Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-16 nPr Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 1-17 Me Cl Br CH.sub.2 CH.sub.2 bond CH.sub.2 1-18 Me Cl SMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.68 (bs, 1H), 7.56 (s, 1H), 4.01 (s, 3H), 3.12 (t, 2H), 2.99 (t, 2H), 2.42 (s, 3H), 2.14-2.07 (m, 2H) 1-19 Me Cl SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.77 (bs, 1H), 7.76 (s, 1H), 3.99 (s, 3H), 3.52-3.46 (m, 1H), 3.29-3.22 (m, 1H), 2.93 (s, 3H), 2.88 (t, 2H), 2.14-2.08 (m, 2H) 1-20 Me Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 11.88 (bs, 1H), 7.92 (s, 1H), 4.01 (s, 3H), 3.40 (s, 3H), 3.39 (t, 2H), 2.95 (t, 2H), 2.10-2.02 (m, 2H) 1-21 Me Cl SEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.7 (bs, 1H), 7.54 (s, 1H), 3.98 (s, 3H), 3.08 (t, 2H), 2.98 (t, 2H), 2.89 (q, 2H), 2.08 (m, 2H), 1.13 (t, 3H) 1-22 Me Cl SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.77 (bs, 1H), 7.76 (s, 1H), 3.99 (s, 3H), 3.53-3.44 (m, 1H), 3.22-3.08 (m, 3H), 2.88 (t, 2H), 2.09 (m, 2H), 1.23 (t, 3H) 1-23 Me Cl SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 11.85 (bs, 1H), 7.91 (s, 1H), 4.00 (s, 3H), 3.50 (q, 2H), 3.37 (t, 2H), 2.95 (t, 2H), 2.07 (m, 2H), 1.18 (t, 3H) 1-24 Et Cl SMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.6 (bs, 1H), 7.49 (s, 1H), 4.32 (q, 2H), 3.09 (t, 2H), 2.96 (t, 2H), 2.39 (s, 3H), 2.08 (m, 2H), 1.45 (t, 3H) 1-25 Et Cl SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.68 (bs, 1H), 7.74 (s, 1H), 4.34 (q, 2H), 3.53-3.21 (m, 2H), 2.93 (s, 3H), 2.89 (t, 2H), 2.11 (m, 2H), 1.46 (t, 3H) 1-26 Et Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 11.76 (bs, 1H), 7.89 (s, 1H), 4.37 (q, 2H), 3.40 (s, 3H), 3.37 (t, 2H), 2.95 (t, 2H), 2.07 (m, 2H), 1.48 (t, 3H) 1-27 Et Cl SEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.6 (bs, 1H), 7.53 (S, 1h), 4.34 (q, 2H), 3.08 (t, 2H), 2.98 (t, 2H) 2.89 (q, 2H), 2.08 (m, 2H), 1.46 (t, 3H), 1.11 (t, 3H) 1-28 Et Cl SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.67 (bs, 1H), 7.75 (s, 1H), 4.35 (q, 2H), 3.52-3.44 (m, 2H), 3.22- 3.09 (m, 3H), 2.88 (t, 2H), 2.08 (m, 2H), 1.46 (t, 3H), 1.23 (t, 3H) 1-29 Et Cl SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 11.76 (bs, 1H), 7.90 (s, 1H), 4.36 (q, 2H), 3.50 (q, 2H), 3.37 (t, 2H), 2.96 (t, 2H), 2.06 (m, 2H), 1.47 (t, 3H), 1.18 (t, 3H) 1-30 Me Cl SMe CO CH.sub.2 bond CH.sub.2 11.93 (bs, 1H), 7.85 (s, 1H), 4.02 (s, 3H), 3.10 (m, 2H), 2.77 (m, 2H), 2.50 (s, 3H) 1-31 Me Cl SOMe CO CH.sub.2 bond CH.sub.2 1-32 Me Cl SO.sub.2Me CO CH.sub.2 bond CH.sub.2 7.92 (s, 1H), 4.17 (s, 3H), 3.51 (s, 3H), 3.22 (m, 2H), 2.92 (m, 2H) 1-33 Me Cl SEt CO CH.sub.2 bond CH.sub.2 1-34 Me Cl SOEt CO CH.sub.2 bond CH.sub.2 1-35 Me Cl SO.sub.2Et CO CH.sub.2 bond CH.sub.2 1-36 Me Cl SMe CF.sub.2 CH.sub.2 bond CH.sub.2 1-37 Me Cl SOMe CF.sub.2 CH.sub.2 bond CH.sub.2 1-38 Me Cl SO.sub.2Me CF.sub.2 CH.sub.2 bond CH.sub.2 1-39 Et Cl SMe CF.sub.2 CH.sub.2 bond CH.sub.2 1-40 Et Cl SOMe CF.sub.2 CH.sub.2 bond CH.sub.2 1-41 Et Cl SO.sub.2Me CF.sub.2 CH.sub.2 bond CH.sub.2 1-42 Me Cl SMe CHMe CH.sub.2 bond CH.sub.2 11.67 (bs, 1H), 7.55 (s, 1H), 3.99 (s, 3H), 3.58-3.50 (m, 1H), 3.14-3.04 (m, 1H), 2.92-2.84 (m1H), 2.42 (s, 3H), 2.32-2.22 (m, 1H), 1.86-78 (m, 1H) 1-43 Me Cl SOMe CHMe CH.sub.2 bond CH.sub.2 1-44 Me Cl SO.sub.2Me CHMe CH.sub.2 bond CH.sub.2 1-45 Me Cl SMe CMe.sub.2 CH.sub.2 bond CH.sub.2 1-46 Me Cl SOMe CMe.sub.2 CH.sub.2 bond CH.sub.2 1-47 Me Cl SO.sub.2Me CME.sub.2 CH.sub.2 bond CH.sub.2 1-48 Et Cl SMe CMe.sub.2 CH.sub.2 bond CH.sub.2 1-49 Et Cl SOMe CMe.sub.2 CH.sub.2 bond CH.sub.2 1-50 Et Cl SO.sub.2Me CMe.sub.2 CH.sub.2 bond CH.sub.2 1-51 Me Cl SMe CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 7.43 (s, 1H), 3.97 (s, 3H), 3.02 (t, 2H), 2.78 (t, 2H), 2.32 (s, 3H), 1.84-1.66 (m, 4H) 1-52 Me Cl SOMe CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 11.75 (bs, 1H), 7.59 (s, 1H), 3.99 (s, 3H), 3.45-3.35 (m, 1H), 3.10-3.00 (m, 1H), 3.03 (s, 3H), 1.78-1.72 (m, 4H) 1-53 Me Cl SO.sub.2Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 11.84 (bs, 1H), 7.74 (s, 1H), 4.00 (s, 3H), 3.42 (s, 3H), 3.25 (m, 2H), 2.86 (m, 2H), 1.71 (m, 4H) 1-54 Me Cl SEt CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-55 Me Cl SOEt CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-56 Me Cl SO.sub.2Et CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-57 Et Cl SMe CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-58 Et Cl SOMe CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-59 Et Cl SO.sub.2Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-60 Et Cl SEt CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-61 Et Cl SOEt CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-62 Et Cl SO.sub.2Et CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 1-63 Me Cl SMe O CH.sub.2 bond CH.sub.2 11.57 (bs, 1H), 7.53 (s, 1H), 4.73 (t, 2H), 3.97 (s, 3H), 3.28 (t, 2H), 2.43 (s, 3H) 1-64 Me Cl SOMe O CH.sub.2 bond CH.sub.2 7.73 (s, 1H), 4.82 (t, 2H), 3.93 (s, 3H), 3.26 (t, 2H), 3.05 (s, 3H) 1-65 Me Cl SO.sub.2Me O CH.sub.2 bond CH.sub.2 11.74 (bs, 1H), 7.83 (s, 1H), 4.82 (t, 2H), 3.99 (s, 3H), 3.37 (s, 3H), 3.27 (t, 2H) 1-66 Me Cl SMe CH.sub.2 O bond CH.sub.2 1-67 Me Cl SOMe CH.sub.2 O bond CH.sub.2 1-68 Me Cl SO.sub.2Me CH.sub.2 O bond CH.sub.2 1-69 Me Cl SMe CH.sub.2 CH.sub.2 bond O 11.69 (bs, 1H), 7.12 (s, 1H), 4.65 (t, 2H), 3.98 (s, 3H), 3.41 (t, 2H), 2.45 (s, 3H) 1-70 Me Cl SOMe CH.sub.2 CH.sub.2 bond O 7.31 (s, 1H), 4.69 (t, 2H), 3.98 (s, 3H), 3.5-3.45 (m, 2H), 2.95 (s, 3H) 1-71 Me Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond O 11.87 (bs, 1H), 7.51 (s, 1H), 4.67 (t, 2H), 4.01 (s, 3H), 3.66 (t, 2H), 3.42 (s, 3H) 1-72 Me Cl SMe O CH.sub.2 bond O 1-73 Me Cl SOMe O CH.sub.2 bond O 1-74 Me Cl SO.sub.2Me O CH.sub.2 bond O 1-75 Me Br SMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.77 (bs, 1H), 7.46 (s, 1H), 3.98 (s, 3H), 3.12 (t, 2H), 2.94 (t, 2H), 2.39 (s, 3H), 2.11-2.03 (m, 2H) 1-76 Me Br SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.75 (bs, 1H), 7.71 (s, 1H), 4.01 (s, 3H), 3.55-3.47 (m, 1H), 3.28-3.20 (m, 1H), 2.91 (s, 3H) 2.10 (m, 2H) 1-77 Me Br SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 11.84 (bs, 1H), 7.84 (s, 1H), 4.03 (s, 3H), 3.41 (t, 2H), 3.40 (s, 3H), 2.93 (t, 2H), 2.05 (m, 2H) 1-78 Me Br SEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.85 (bs, 1H), 7.48 (s, 1H), 3.99 (s, 3H), 3.10 (t, 2H), 2.95 (t, 2H), 2.89 (q, 2H), 2.07 (m, 2H), 1.14 (t, 3H) 1-79 Me Br SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.78 (bs, 1H), 7.71 (s, 1H), 4.01 (s, 3H), 3.55-3.47 (m, 1H), 3.23-3.09 (m, 3H), 2.85 (t, 2H), 2.08 (m, 2H), 1.25 (t, 3H) 1-80 Me Br SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 11.84 (bs, 1H), 7.85 (s, 1H), 4.03 (s, 3H), 3.52 (q, 2H), 3.39 (t, 2H), 2.93 (t, 2H), 2.05 (m, 2H), 1.19 (t, 3H) 1-81 Et Br SMe CH.sub.2 CH.sub.2 bond CH.sub.2 1-82 Et Br SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 1-83 Et Br SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 1-84 Et Br SEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.7 (bs, 1H), 7.47 (s, 1H), 4.36 (q, 2H), 3.10 (t, 2H), 2.96 (t, 2H), 2.89 (q, 2H), 2.06 (m, 2H), 1.46 (t, 3H), 1.14 (t, 3H) 1-85 Et Br SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 11.66 (bs, 1H), 7.70 (s, 1H), 4.36 (q, 2H), 3.55-3.47 (m, 2H), 3.22- 3.09 (m, 3H), 2.86 (t, 2H), 2.08 (m, 2H), 1.47 (t, 3H), 1.25 (t, 3H) 1-86 Et Br SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 11.74 (bs, 1H), 7.84 (s, 1H), 4.38 (q, 2H), 3.52 (q, 2H), 3.38 (t, 2H), 2.94 (t, 2H), 2.05 (m, 2H), 1.48 (t, 3H), 1.19 (t, 3H) 1-87 Me Me F SO.sub.2 CH.sub.2 bond CH.sub.2 11.82 (bs, 1H), 7.67 (s, 1H), 3.99 (s, 3H), 3.76 (t, 2H), 3.41 (t, 2H), 2.36 (d, 3H) 1-88 Me Me SMe SO.sub.2 CH.sub.2 bond CH.sub.2 11.05 (bs, 1H), 7.81 (s, 1H), 4.13 (s, 3H), 3.59 (t, 2H), 3.42 (t, 2H), 2.77 (s, 3H), 2.46 (s, 3H) 1-89 Me Me SOMe SO.sub.2 CH.sub.2 bond CH.sub.2 7.93 (s, 1H), 4.01 (s, 3H), 3.76-3.66 (m, 2H), 3.41 (t, 2H), 3.03 (s, 3H), 2.77 (s, 3H) 1-90 Me Me SO.sub.2Me SO.sub.2 CH.sub.2 bond CH.sub.2 8.10 (s, 1H), 4.02 (s, 3H), 3.66 (t, 2H), 3.41 (t, 2H), 3.40 (s, 3H), 2.72 (s, 3H) 1-91 Me Me SEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-92 Me Me SOEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-93 Me Me SO.sub.2Et SO.sub.2 CH.sub.2 bond CH.sub.2 1-94 Et Me SMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-95 Et Me SOMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-96 Et Me SO.sub.2Me SO.sub.2 CH.sub.2 bond CH.sub.2 1-97 Et Me SEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-98 Et Me SOEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-99 Et Me SO.sub.2Et SO.sub.2 CH.sub.2 bond CH.sub.2 1-100 Me Me OMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-101 Me Me OEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-102 Me Me OC.sub.2H.sub.4OMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-103 Me Me Pyrazol-1- SO.sub.2 CH.sub.2 bond CH.sub.2 10.98 (bs, 1H), 7.85 (s, 1H), 7.77 yl (d, 1H), 7.73 (d, 1H), 6.56 (t, 1H), 4.11 (s, 3H), 3.54 (t, 2H), 3.43 (t, 2H), 2.23 (s, 3H) 1-104 Me Cl H SO.sub.2 CH.sub.2 bond CH.sub.2 1-105 Me Cl Cl SO.sub.2 CH.sub.2 bond CH.sub.2 11.98 (bs, 1H), 7.97 (s, 1H), 4.01 (s, 3H), 3.81 (t, 2H), 3.40 (t, 2H) 1-106 Me Cl SMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-107 Me Cl SOMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-108 Me Cl SO.sub.2Me SO.sub.2 CH.sub.2 bond CH.sub.2 1-109 Me Cl SEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-110 Me Cl SOEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-111 Me Cl SO.sub.2Et SO.sub.2 CH.sub.2 bond CH.sub.2 1-112 Et Cl SMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-113 Et Cl SOMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-114 Et Cl SO.sub.2Me SO.sub.2 CH.sub.2 bond CH.sub.2 1-115 Et Cl SEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-116 Et Cl SOEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-117 Et Cl SO.sub.2Et SO.sub.2 CH.sub.2 bond CH.sub.2 1-118 Me Cl OMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-119 Me Cl OEt SO.sub.2 CH.sub.2 bond CH.sub.2 1-120 Me Cl OC.sub.2H.sub.4OMe SO.sub.2 CH.sub.2 bond CH.sub.2 1-121 Me Cl Pyrazol-1- SO.sub.2 CH.sub.2 bond CH.sub.2 yl

    TABLE-US-00002 TABLE 2 Inventive compounds of the general formula (I) in which Q is Q.sup.2, in which R.sup.3 is methyl, and Z.sup.4 is a direct bond [00008]embedded image Physical data No. X Y Z.sup.1 Z.sup.2 Z.sup.3 Z.sup.5 (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 2-1 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-2 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-3 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-4 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-5 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-6 nPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-7 cPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-8 Me SMe CH.sub.2 CH.sub.2 bond CH.sub.2 2-9 Me SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 2-10 Me SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 2-11 Me SEt CH.sub.2 CH.sub.2 bond CH.sub.2 2-12 Me SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 2-13 Me SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 2-14 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-15 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-16 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 2-17 Cl Br CH.sub.2 CH.sub.2 bond CH.sub.2 2-18 Cl SMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.09 (bs, 1H), 7.88 (s1H), 7.48 (s, 1H), 3.76 (s, 3H), 3.09 (t, 2H), 2.96 (t, 2H), 2.40 (s, 3H), 2.08 (m, 2H) 2-19 Cl SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 2-20 Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 11.28 (bs, 1H), 7.90 (s, 1H), 7.85 (s, 1H), 3.78 (s, 3H), 3.39 (s, 3H), 3.38 (t, 2H), 2.94 (t, 2H), 2.06 (m, 2H) 2-21 Cl SEt CH.sub.2 CH.sub.2 bond CH.sub.2 2-22 Cl SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 2-23 Cl SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2

    TABLE-US-00003 TABLE 3 Inventive compounds of the general formula (I) in which Q is Q.sup.3, in which R.sup.4 is methyl, and Z.sup.4 is a direct bond [00009]embedded image Physical data No. X Y Z.sup.1 Z.sup.2 Z.sup.3 Z.sup.5 (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 3-1 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-2 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-3 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-4 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-5 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-6 nPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-7 cPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-8 Me SMe CH.sub.2 CH.sub.2 bond CH.sub.2 3-9 Me SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 3-10 Me SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 3-11 Me SEt CH.sub.2 CH.sub.2 bond CH.sub.2 3-12 Me SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 3-13 Me SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 3-14 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-15 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-16 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 3-17 Cl Br CH.sub.2 CH.sub.2 bond CH.sub.2 3-18 Cl SMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.34 (bs, 1H), 7.49 (s1H), 3.10 (t, 2H), 2.96 (t, 2H), 2.40 (s, 3H), 2.38 (t, 3H), 2.08 (m, 2H) 3-19 Cl SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 11.41 (bs, 1H), 7.70 (s1H), 3.52-3.22 (m, 2H), 2.93 (s, 3H), 2.88 (t, 2H), 2.38 (s, 3H), 2.10 (m, 2H) 3-20 Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 11.50 (bs, 1H), 7.84 (s1H), 3.39 (s, 3H), 3.36 (t, 2H), 2.94 (t, 2H), 2.40 (s, 3H), 2.06 (m, 2H) 3-21 Cl SEt CH.sub.2 CH.sub.2 bond CH.sub.2 3-22 Cl SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 3-23 Cl SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2

    TABLE-US-00004 TABLE 4 Inventive compounds of the general formula (I) in which Q is Q.sup.4, in which R.sup.5 is methyl, and Z.sup.4 is a direct bond [00010]embedded image Physical data No. X Y Z.sup.1 Z.sup.2 Z.sup.3 Z.sup.5 (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 4-1 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-2 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-3 Me Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-4 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-5 Et Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-6 nPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-7 cPr Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-8 Me SMe CH.sub.2 CH.sub.2 bond CH.sub.2 4-9 Me SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 4-10 Me SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 4-11 Me SEt CH.sub.2 CH.sub.2 bond CH.sub.2 4-12 Me SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 4-13 Me SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2 4-14 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-15 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-16 Cl Cl CH.sub.2 CH.sub.2 bond CH.sub.2 4-17 Cl Br CH.sub.2 CH.sub.2 bond CH.sub.2 4-18 Cl SMe CH.sub.2 CH.sub.2 bond CH.sub.2 12.06 (bs, 1H), 7.42 (s1H), 3.09 (t, 2H), 2.93 (t, 2H), 2.47 (s, 3H), 2.39 (s, 3H), 2.07 (m, 2H) 4-19 Cl SOMe CH.sub.2 CH.sub.2 bond CH.sub.2 4-20 Cl SO.sub.2Me CH.sub.2 CH.sub.2 bond CH.sub.2 4-21 Cl SEt CH.sub.2 CH.sub.2 bond CH.sub.2 4-22 Cl SOEt CH.sub.2 CH.sub.2 bond CH.sub.2 4-23 Cl SO.sub.2Et CH.sub.2 CH.sub.2 bond CH.sub.2

    B. FORMULATION EXAMPLES

    [0086] a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. [0087] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0088] c) A readily water-dispersible dispersion concentrate is obtained by mixing parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to above 277 C), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. [0089] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0090] e) Water-dispersible granules are obtained by mixing [0091] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0092] 10 parts by weight of calcium lignosulfonate, [0093] 5 parts by weight of sodium lauryl sulfate, [0094] 3 parts by weight of polyvinyl alcohol and [0095] 7 parts by weight of kaolin, [0096] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. [0097] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0098] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0099] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate [0100] 2 parts by weight of sodium oleoylmethyltaurate, [0101] 1 part by weight of polyvinyl alcohol [0102] 17 parts by weight of calcium carbonate and [0103] 50 parts by weight of water, [0104] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

    C. BIOLOGICAL EXAMPLES

    1. Pre-Emergence Herbicidal Action Against Harmful Plants

    [0105] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood-fiber pots in sandy loam and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 I/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). For example, compounds no. 1-20, 1-23, 1-25, 1-26, 1-27, 1-52, 1-69, 1-75, 1-77 and 1-78 at an application rate of 320 g/ha each have at least 80% efficacy against Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Pharbitis purpureum, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor.

    2. Post-Emergence Herbicidal Action Against Harmful Plants

    [0106] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 I/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). For example, compounds no. 1-18, 1-19, 1-20, 1-21, 1-23, 1-25, 1-26, 1-27, 1-30, 1-32, 1-51, 1-52, 1-53, 1-63, 1-65, 1-69, 1-70, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-84, 2-18, 2-20 and 4-18 at an application rate of 80 g/ha each have 100% efficacy against Stellaria media, Veronica persica and Viola tricolor.