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N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivatives with herbicidal action

10548318 · 2020-02-04

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Inventors

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Abstract

N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivatives of the general formula (I) are described as herbicides. ##STR00001##
In this formula (I), V, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A represents a tetrazole or triazole radical. W is CY or N.

Claims

1. An N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) ##STR00045## wherein the symbols and indices are each defined as follows: W is N or CY, X and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, (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.3-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(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, (C.sub.1-C.sub.6)-alkyl-NR.sup.1SO.sub.2R.sup.2, NR.sup.1R.sup.2, P(O)(OR.sup.5).sub.2, or heteroaryl, heterocyclyl or phenyl, each substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, 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, CO.sub.2R.sup.1, OCO.sub.2R.sup.1, NR.sup.1CO.sub.2R.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)N(R.sup.1)OR.sup.1, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, OR.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, (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-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.5).sub.2, CH.sub.2P(O)(OR.sup.5).sub.2, CHNOR.sup.1, (C.sub.1-C.sub.6)-alkyl-CHNOR.sup.1, (C.sub.1-C.sub.6)-alkyl-ONC(R.sup.1).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, wherein the latter 6 radicals are each substituted by s radicals selected 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, 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).sub.2, CNR.sup.10, C(OR.sup.11).sub.2, C[O(CH.sub.2).sub.2O-] or C(O) elements as ring members, wherein the carbon atoms are substituted by s radicals selected from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.10)-alkenyl, (C.sub.2-C.sub.10)-alkynyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, phenoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.8)-alkoxyalkyl and phenyl, wherein the nitrogen atoms are substituted by n radicals selected from the group consisting of (C.sub.1-C.sub.6)-alkyl and phenyl, and wherein the aforementioned phenyl radicals are substituted by s radicals selected from the group consisting of cyano, nitro, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl and (C.sub.1-C.sub.6)-alkoxy, V is hydrogen, nitro, halogen, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or OR.sup.1, S(O).sub.nR.sup.2, 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.3-heteroaryl or (C.sub.1-C.sub.6)-alkyl-NR.sup.3-heterocyclyl, wherein the 21 latter radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR.sup.3, S(O).sub.nR.sup.4, N(R.sup.3).sub.2, NR.sup.3OR.sup.3, COR.sup.3, OCOR.sup.3, SCOR.sup.4, NR.sup.3COR.sup.3, NR.sup.3SO.sub.2R.sup.4, CO.sub.2R.sup.3, COSR.sup.4, CON(R.sup.3).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.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, (C.sub.1-C.sub.6)-alkyl-NR.sup.3-heterocyclyl, wherein the 21 latter radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR.sup.3, S(O).sub.nR.sup.4, N(R.sup.3).sub.2, NR.sup.3OR.sup.3, COR.sup.3, OCOR.sup.3, SCOR.sup.4, NR.sup.3COR.sup.3, NR.sup.3SO.sub.2R.sup.4, CO.sub.2R.sup.3, COSR.sup.4, CON(R.sup.3).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.3 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 or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.4 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 or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.5 is (C.sub.1-C.sub.4)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3, A is an A1, A2, A3 or A4 radical ##STR00046## B is N or CH, R is (C.sub.1-C.sub.6)-alkyl-OC(O)N(R.sup.3).sub.2 or (C.sub.1-C.sub.6)-alkyl-OC(O)OR.sup.12, R.sup.6 is (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, or halo-(C.sub.2-C.sub.6)-alkynyl, wherein these 6 aforementioned radicals are each substituted by s radicals selected from the group consisting of nitro, cyano, SiR.sup.9.sub.3, PO(OR.sup.9).sub.3, 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, N(R.sup.7).sub.2, COR.sup.7, CO.sub.2R.sup.7, OCOR.sup.7, OCO.sub.2R.sup.7, NR.sup.7COR.sup.7, NR.sup.7SO.sub.2R.sup.8, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl and D-benzyl, and wherein the 7 latter radicals are substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, and where heterocyclyl bears n oxo groups, or R.sup.6 is (C.sub.3-C.sub.7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substituted by s radicals selected 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.7 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.8 is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl or phenyl, R.sup.9 is (C.sub.1-C)-alkyl, R.sup.10 is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy or halo-(C.sub.1-C.sub.6)-alkoxy, R.sup.11 is (C.sub.1-C.sub.6)-alkyl or halo-(C.sub.1-C.sub.6)-alkyl, R.sup.12 is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-cycloalkyl, s is 0, 1, 2 or 3, n is 0, 1 or 2, D is O, S, or NR.sup.8.

2. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimed in claim 1, wherein R.sup.6 is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, or (C.sub.2-C.sub.6)-alkynyl, wherein these 4 aforementioned radicals are each substituted by s radicals selected from the group consisting of 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, N(R.sup.7).sub.2, COR.sup.7, CO.sub.2R.sup.7, OCOR.sup.7, OCO.sub.2R.sup.7, NR.sup.7COR.sup.7, NR.sup.7SO.sub.2R.sup.8, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl and D-benzyl, and wherein the 7 latter radicals are substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, and wherein heterocyclyl bears n oxo groups, or R.sup.6 is (C.sub.3-C.sub.7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substituted by s radicals selected 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.

3. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimed in claim 1, wherein W is CY, X and Z are each independently hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl, OR.sup.1, S(O).sub.nR.sup.2, 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, or (C.sub.1-C.sub.6)-alkyl-OR.sup.1, or heteroaryl, heterocyclyl or phenyl, each substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, Y is hydrogen, (C.sub.2-C.sub.6)-alkenyl, COR.sup.1, CO.sub.2R.sup.1, OCO.sub.2R.sup.1, NR.sup.1CO.sub.2R.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)N(R.sup.1)OR.sup.1, NR.sup.1SO.sub.2R.sup.2, NR.sup.1COR.sup.1, OR.sup.1, S(O).sub.nR.sup.2, 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-CO.sub.2R.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, CHNOR.sup.1, (C.sub.1-C.sub.6)-alkyl-CHNOR.sup.1, (C.sub.1-C.sub.6)-alkylheteroaryl, (C.sub.1-C.sub.6)-alkylheterocyclyl, heteroaryl or heterocyclyl, wherein the 4 latter radicals are each substituted by s radicals selected 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 wherein heterocyclyl bears n oxo groups, V is hydrogen, Cl, OMe, methyl or ethyl, R.sup.6 is methyl, ethyl, or n-propyl.

4. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimed in claim 1, wherein W is CY, X is F, Cl, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, methoxymethyl, methoxyethoxymethyl, SMe or SO.sub.2Me, Z is hydrogen, F, Cl, Br, I, methyl, ethyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfonyl or ethylsulfonyl, Y is hydrogen, SMe, S(O)Me, SO.sub.2Me, SEt, S(O)Et, SO.sub.2Et, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2OCH.sub.2CF.sub.3, CH.sub.2SMe, CH.sub.2S(O)Me, CH.sub.2SO.sub.2Me, vinyl, C(O)Me, C(O)Et, C(O)cPr, CO.sub.2Me, CHNOMe, 4,5-dihydro-1,2-oxazol-3-yl, 5-methyl-4,5-dihydro-1,2-oxazol-3-yl, 5-methyl-4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, 4,5-dihydro-1,2-oxazol-5-yl, 3-methyl-4,5-dihydro-1,2-oxazol-5-yl, 1H-pyrazol-1-yl, 1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl, pyrolidin-2-on-1-yl, morpholin-3-on-4-yl, OMe, OEt, O-n-Pr, OCH.sub.2-c-Pr, OCH.sub.2CH.sub.2F; OCH.sub.2CH.sub.2OMe or OCH.sub.2CH.sub.2CH.sub.2OMe, V is hydrogen, B is N, R is CH.sub.2OCO.sub.2Et, CH(CH.sub.3)OCO.sub.2Me, CH(CH.sub.3)OCO.sub.2Et, CH(CH.sub.3)OCO.sub.2-c-hexyl, CH(CH.sub.3)OCO.sub.2-i-Pr or CH(CH.sub.3)OCO.sub.2-t-Bu, R.sup.6 is methyl or ethyl.

5. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 4, wherein A is A1.

6. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 5, wherein R is CH(CH.sub.3)OCO.sub.2Et, and R.sup.6 is methyl.

7. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 6, wherein X is Cl.

8. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 6, wherein Z is methyl.

9. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 6, wherein Y is SO.sub.2Me.

10. The N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivative of formula (I) as claimed in claim 7, wherein Y is SO.sub.2Me, and Z is methyl.

11. A herbicidal composition comprising a herbicidally effective amount of at least one N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimed in claim 1.

12. The herbicidal composition as claimed in claim 11 in a mixture with one or more formulation auxiliaries.

13. The herbicidal composition as claimed in claim 11, comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

14. The herbicidal composition as claimed in claim 13, comprising a safener.

15. The herbicidal composition as claimed in claim 14, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

16. The herbicidal composition as claimed in claim 11, comprising a further herbicide.

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

18. The method as claimed in claim 17, wherein the effective amount of at least one compound of the formula (I) is applied to one or more unwanted plants in crops of one or more useful plants.

19. The method as claimed in claim 18, wherein the useful plants are transgenic useful plants.

Description

A. CHEMICAL EXAMPLES

(1) 1. Synthesis of 1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethyl ethyl carbonate (Table example No. 1-384) and 1-[(ethoxycarbonyl)oxy]ethyl 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate (Table example No. 19-384):

(2) To a solution of 1.00 g (2.843 mmol) of 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide are in 20 ml of acetonitrile are added at room temperature 911 mg (5.97 mmol) of 1-chloroethyl ethyl carbonate and 825 mg (5.97 mmol) of potassium carbonate and the mixture is boiled under reflux for 9 h. The reaction mixture is concentrated and then dissolved in 20 ml of ethyl acetate and 20 ml of water are added and extracted. The aqueous phase is extracted twice more with 20 ml of ethyl acetate each time. The combined organic phases are washed with saturated NaCl solution, dried and concentrated. The residue is purified by RP-HPLC (acetonitrile/water).

(3) Compound No. 1-384

(4) Yield: 230 mg (15.7%)

(5) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.78 ppm (d, 1H), 7.67 ppm (d, 1H), 7.03 (q, 1H), 4.25-4.16 (m, 2H); 3.97 (s, 3H); 2.43 (s, 3H); 2.00 (d, 3H), 1.29 (t; 3H).

(6) Compound No. 19-384

(7) Yield: 200 mg (13.5%)

(8) .sup.1H-NMR (400 MHz; CDCl.sub.3): 8.04 ppm (d, 1H), 7.81 ppm (d, 1H), 6.74 (q, 1H), 4.25-4.18 (m, 2H); 3.25 (s, 3H); 2.92 (s, 3H); 2.49 (s, 3H); 1.77 (d, 3H), 1.30 (t; 3H).

(9) 2. Synthesis of 1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethyl methyl carbonate (Table example No. 3-384) and

(10) 1-[(Methoxycarbonyl)oxy]ethyl 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate (Table example No. 21-384)

(11) By analogy to the abovementioned preparation method, by reacting 1.00 g (2.843 mmol) of 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide with 871 mg (5.71 mmol) of 1-chloroethyl ethyl carbonate, isolated were:

(12) Compound No. 3-384

(13) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.78 ppm (d, 1H), 7.68 ppm (d, 1H), 7.04 (q, 1H), 3.98 (s, 3H); 3.80 (s, 3H), 2.43 (s, 3H); 2.00 (d, 3H).

(14) Compound No. 21-384

(15) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.73 ppm (d, 1H), 7.53 ppm (d, 1H), 7.28 (q, 1H), 3.97 (s, 3H); 3.86 (s, 3H); 2.33 (s, 3H), 1.75 (d, 3H).

(16) 3. Synthesis of 1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethyl cyclohexyl carbonate (Table example No. 5-384) and 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate (Table example No. 23-384):

(17) By analogy to the abovementioned preparation method, by reacting 1.00 g (2.719 mmol) of 2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide with 1234 mg (5.97 mmol) of 1-chloroethyl cyclohexyl carbonate, isolated were:

(18) Compound No. 5-384

(19) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.77 ppm (d, 1H), 7.68 ppm (d, 1H), 7.00 (q, 1H), 4.65-4.59 (m, 1H), 3.98 (s, 3H); 2.43 (s, 3H); 2.00 (d, 3H); 1.98-1.88 (m, 1H), 1.85-1.65 (m, 4H), 1.59-1.18 (m, 5H).

(20) Compound No. 23-384

(21) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.96 ppm (d, 1H), 7.73 ppm (d, 1H), 7.54 ppm (d, 1H), 7.27 (q, 1H), 4.72-4.63 (m, 1H), 3.97 (s, 3H); 2.32 (s, 3H); 2.00-1.86 (m, 2H), 1.77-1.65 (m, 5H), 1.59-1.21 (m, 6H).

(22) Compound No. 32-384

(23) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.81 ppm and 7.72 ppm (2d, 1H), 7.52 ppm and 7.38 (2d, 1H), 6.23 and 5.95 (2q, 1H), 4.72 and 4.56 (2m, 1H), 4.12-3.98 (3s, 3H); 2.2.46 and 2.34 (2s, 3H); 2.01-1.766 (m, 4H), 1.59-1.1.22 (m, 8H).

(24) 4. Synthesis of 1-(5-{[2-chloro-4-methyl-3-(methylsulfonyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethyl ethyl carbonate (Table example No. 1-390), 1-[(ethoxycarbonyl)oxy]ethyl 2-chloro-4-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzenecarboximidate (Table example No. 19-390) and 1-{[2-chloro-4-methyl-3-(methylsulfonyl)benzoyl](1-methyl-1H-tetrazol-5-yl)amino}ethyl ethyl carbonate (Table example No. 28-390):

(25) To a solution of 100 mg (0.303 mmol) of 2-chloro-4-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl) benzamide in 3 ml of acetonitrile are added at room temperature 49 mg (0.318 mmol) of 1-chloroethyl ethyl carbonate and 104 mg (5.97 mmol) of cesium carbonate. The mixture is heated to 75 C. for 5 d and stirred at RT until reaction is complete (LC-MS monitoring). The reaction mixture is filtered and the solvent is removed under reduced pressure. The residue is purified by RP-HPLC (acetonitrile/water).

(26) Compound No. 1-390

(27) Yield: 32 mg (24%)

(28) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.80 ppm (d, 1H), 7.27 ppm (d, 1H), 7.01 (q, 1H), 4.23-4.19 (m, 2H); 3.95 (s, 3H); 3.34 (s, 3H); 2.78 (s, 3H), 2.00 (d, 3H), 1.29 (t; 3H).

(29) Compound No. 19-390

(30) Yield: 26 mg (19%)

(31) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.96 ppm (d, 1H), 7.50 ppm (d, 1H), 7.34 ppm (d, 1H), 7.26 (q, 1H), 4.27-4.24 (m, 2H); 3.96 (s, 3H); 3.20 (s, 3H), 2.79 (s, 3H); 1.74 (d, 3H), 1.34 (t; 3H).

(32) Compound No. 28-390

(33) Yield: 36 mg (27%)

(34) .sup.1H-NMR (400 MHz; CDCl.sub.3): 7.96 ppm (d, 1H), 7.72 ppm (br, 1H), 7.49 ppm (d, 1H), 6.48 (br, 1H), 4.17 (q, 2H); 4.01 (s, 3H); 3.31 (s, 3H), 2.69 (s, 3H); 1.39 (d, 3H), 1.23 (t; 3H).

(35) 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.

(36) TABLE-US-00001 TABLE 1 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen embedded image Physical data No. X Y Z (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 1-1 F H Cl 1-2 F H SO.sub.2Me 1-3 F H SO.sub.2Et 1-4 F H CF.sub.3 1-5 F H NO.sub.2 1-6 Cl H Br 1-7 Cl H SMe 1-8 Cl H SOMe 1-9 Cl H SO.sub.2Me 1-10 Cl H SO.sub.2CH.sub.2Cl 1-11 Cl H SEt 1-12 Cl H SO.sub.2Et 1-13 Cl H CF.sub.3 1-14 Cl H NO.sub.2 1-15 Cl H pyrazol-1-yl 1-16 Cl H 1H-1,2,4- triazol-1-yl 1-17 Br H Cl 1-18 Br H Br 1-19 Br H SO.sub.2Me 1-20 Br H SO.sub.2Et 1-21 Br H CF.sub.3 1-22 SO.sub.2Me H Cl 1-23 SO.sub.2Me H Br 1-24 SO.sub.2Me H SMe 1-25 SO.sub.2Me H SOMe 1-26 SO.sub.2Me H SO.sub.2Me 1-27 SO.sub.2Me H SO.sub.2Et 1-28 SO.sub.2Me H CF.sub.3 1-29 SO.sub.2Et H Cl 1-30 SO.sub.2Et H Br 1-31 SO.sub.2Et H SMe 1-32 SO.sub.2Et H SOMe 1-33 SO.sub.2Et H SO.sub.2Me 1-34 SO.sub.2Et H CF.sub.3 1-35 NO.sub.2 H F 1-36 NO.sub.2 H Cl 1-37 NO.sub.2 H Br 1-38 NO.sub.2 H I 1-39 NO.sub.2 H CN 1-40 NO.sub.2 H SO.sub.2Me 1-41 NO.sub.2 H SO.sub.2Et 1-42 NO.sub.2 H CF.sub.3 1-43 Me H Cl 1-44 Me H Br 1-45 Me H SMe 1-46 Me H SO.sub.2Me 1-47 Me H SO.sub.2CH.sub.2Cl 1-48 Me H SEt 1-49 Me H SO.sub.2Et 1-50 Me H CF.sub.3 1-51 CH.sub.2SO.sub.2Me H CF.sub.3 1-52 Et H Cl 1-53 Et H Br 1-54 Et H SMe 1-55 Et H SO.sub.2Me 1-56 Et H SO.sub.2CH.sub.2Cl 1-57 Et H SEt 1-58 Et H SO.sub.2Et 1-59 Et H CF.sub.3 1-60 CF.sub.3 H Cl 1-61 CF.sub.3 H Br 1-62 CF.sub.3 H SO.sub.2Me 1-63 CF.sub.3 H SO.sub.2Et 1-64 CF.sub.3 H CF.sub.3 1-65 NO.sub.2 NH.sub.2 F 1-66 NO.sub.2 NHMe F 1-67 NO.sub.2 NMe.sub.2 F 1-68 NO.sub.2 Me Cl 1-69 NO.sub.2 NH.sub.2 Cl 1-70 NO.sub.2 NHMe Cl 1-71 NO.sub.2 NMe.sub.2 Cl 1-72 NO.sub.2 NH.sub.2 Br 1-73 NO.sub.2 NHMe Br 1-74 NO.sub.2 NMe.sub.2 Br 1-75 NO.sub.2 NH.sub.2 CF.sub.3 1-76 NO.sub.2 NMe.sub.2 CF.sub.3 1-77 NO.sub.2 NH.sub.2 SO.sub.2Me 1-78 NO.sub.2 NH.sub.2 SO.sub.2Et 1-79 NO.sub.2 NHMe SO.sub.2Me 1-80 NO.sub.2 NMe.sub.2 SO.sub.2Me 1-81 NO.sub.2 NMe.sub.2 SO.sub.2Et 1-82 NO.sub.2 NH.sub.2 1H-1,2,4- triazol-1-yl 1-83 NO.sub.2 NHMe 1H-1,2,4- triazol-1-yl 1-84 NO.sub.2 NMe.sub.2 1H-1,2,4- triazol-1-yl 1-85 Me SMe H 1-86 Me SOMe H 1-87 Me SO.sub.2Me H 1-88 Me SEt H 1-89 Me SOEt H 1-90 Me SO.sub.2Et H 1-91 Me S(CH.sub.2).sub.2OMe H 1-92 Me SO(CH.sub.2).sub.2OMe H 1-93 Me SO.sub.2(CH.sub.2).sub.2OMe H 1-94 Me F F 1-95 Me F Cl 1-96 Me SEt F 1-97 Me SOEt F 1-98 Me SO.sub.2Et F 1-99 Me Me Cl 1-100 Me F Cl 1-101 Me Cl Cl 1-102 Me NH.sub.2 Cl 1-103 Me NHMe Cl 1-104 Me NMe.sub.2 Cl 1-105 Me O(CH.sub.2).sub.2OMe Cl 1-106 Me O(CH.sub.2).sub.3OMe Cl 1-107 Me O(CH.sub.2).sub.4OMe Cl 1-108 Me OCH.sub.2CONMe.sub.2 Cl 1-109 Me O(CH.sub.2).sub.2CONMe.sub.2 Cl 1-110 Me O(CH.sub.2).sub.2NH(CO)NMe.sub.2 Cl 1-111 Me O(CH.sub.2).sub.2NH(CO)NHCO.sub.2Et Cl 1-112 Me O(CH.sub.2).sub.2NHCO.sub.2Me Cl 1-113 Me OCH.sub.2NHSO.sub.2cPr Cl 1-114 Me O(CH.sub.2)-5-2,4-dimethyl- Cl 2,4-dihydro-3H- 1,2,4-triazol-3-one 1-115 Me O(CH.sub.2)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 1-116 Me SMe Cl 1-117 Me SOMe Cl 1-118 Me SO.sub.2Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO.sub.2Et Cl 1-122 Me S(CH.sub.2).sub.2OMe Cl 1-123 Me SO(CH.sub.2).sub.2OMe Cl 1-124 Me SO.sub.2(CH.sub.2).sub.2OMe Cl 1-125 Me NH.sub.2 Br 1-126 Me NHMe Br 1-127 Me NMe.sub.2 Br 1-128 Me OCH.sub.2(CO)NMe.sub.2 Br 1-129 Me O(CH.sub.2)-5-pyrrolidin-2-one Br 1-130 Me SMe Br 1-131 Me SOMe Br 1-132 Me SO.sub.2Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO.sub.2Et Br 1-136 Me SMe I 1-137 Me SOMe I 1-138 Me SO.sub.2Me I 1-139 Me SEt I 1-140 Me SOEt I 1-141 Me SO.sub.2Et I 1-142 Me Cl CF.sub.3 1-143 Me SMe CF.sub.3 1-144 Me SOMe CF.sub.3 1-145 Me SO.sub.2Me CF.sub.3 1-146 Me SEt CF.sub.3 1-147 Me SOEt CF.sub.3 1-148 Me SO.sub.2Et CF.sub.3 1-149 Me S(CH.sub.2).sub.2OMe CF.sub.3 1-150 Me SO(CH.sub.2).sub.2OMe CF.sub.3 1-151 Me SO.sub.2(CH.sub.2).sub.2OMe CF.sub.3 1-152 Me Me SO.sub.2Me 1-153 Me 4,5-dihydro-1,2- SO.sub.2Me oxazol-3-yl 1-154 Me 4,5-dihydro-1,2- SO.sub.2Et oxazol-3-yl 1-155 Me 5-cyanomethyl-4,5- SO.sub.2Me dihydro-1,2-oxazol-3-yl 1-156 Me 5-cyanomethyl-4,5- SO.sub.2Et dihydro-1,2-oxazol-3-yl 1-157 Me NH.sub.2 SO.sub.2Me 1-158 Me NHMe SO.sub.2Me 1-159 Me NMe.sub.2 SO.sub.2Me 1-160 Me NH(CH.sub.2).sub.2OMe SO.sub.2Me 1-161 Me pyrazol-1-yl SO.sub.2Me 1-162 Me OH SO.sub.2Me 1-163 Me OMe SO.sub.2Me 1-164 Me OMe SO.sub.2Et 1-165 Me OEt SO.sub.2Me 1-166 Me OEt SO.sub.2Et 1-167 Me Oi-Pr SO.sub.2Me 1-168 Me Oi-Pr SO.sub.2Et 1-169 Me O(CH.sub.2).sub.2OMe SO.sub.2Me 1-170 Me O(CH.sub.2).sub.2OMe SO.sub.2Et 1-171 Me O(CH.sub.2).sub.3OMe SO.sub.2Me 1-172 Me O(CH.sub.2).sub.3OMe SO.sub.2Et 1-173 Me O(CH.sub.2).sub.4OMe SO.sub.2Me 1-174 Me O(CH.sub.2).sub.4OMe SO.sub.2Et 1-175 Me O(CH.sub.2).sub.2NHSO2Me SO.sub.2Me 1-176 Me O(CH.sub.2).sub.2NHSO2Me SO.sub.2Et 1-177 Me OCH.sub.2(CO)NMe.sub.2 SO.sub.2Me 1-178 Me OCH.sub.2(CO)NMe.sub.2 SO.sub.2Et 1-179 Me [1,4]dioxan-2- SO.sub.2Me ylmethoxy 1-180 Me [1,4]dioxan-2- SO.sub.2Et ylmethoxy 1-181 Me O(CH.sub.2).sub.2O-(3,5- SO.sub.2Me dimethoxypyrimidin-2-yl) 1-182 Me Cl SO.sub.2Me 1-183 Me SMe SO.sub.2Me 1-184 Me SOMe SO.sub.2Me 1-185 Me SO.sub.2Me SO.sub.2Me 1-186 Me SO.sub.2Me SO.sub.2Et 1-187 Me SEt SO.sub.2Me 1-188 Me SOEt SO.sub.2Me 1-189 Me SO.sub.2Et SO.sub.2Me 1-190 Me S(CH.sub.2).sub.2OMe SO.sub.2Me 1-191 Me SO(CH.sub.2).sub.2OMe SO.sub.2Me 1-192 Me SO.sub.2(CH.sub.2).sub.2OMe SO.sub.2Me 1-193 CH.sub.2SMe OMe SO.sub.2Me 1-194 CH.sub.2OMe OMe SO.sub.2Me 1-195 CH.sub.2O(CH.sub.2).sub.2 NH(CH.sub.2).sub.2OEt SO.sub.2Me OMe 1-196 CH.sub.2O(CH.sub.2).sub.2 NH(CH.sub.2).sub.3OEt SO.sub.2Me OMe 1-197 CH.sub.2O(CH.sub.2).sub.3 OMe SO.sub.2Me OMe 1-198 CH.sub.2O(CH.sub.2).sub.2 NH(CH.sub.2).sub.2OMe SO.sub.2Me OMe 1-199 CH.sub.2O(CH.sub.2).sub.2 NH(CH.sub.2).sub.3OMe SO.sub.2Me OMe 1-200 Et SMe Cl 1-201 Et SO.sub.2Me Cl 1-202 Et SMe CF.sub.3 1-203 Et SO.sub.2Me CF.sub.3 1-204 Et F SO.sub.2Me 1-205 Et NH(CH.sub.2).sub.2OMe SO.sub.2Me 1-206 i-Pr SO.sub.2Me CF.sub.3 1-207 cPr SO.sub.2Me CF.sub.3 1-208 CF.sub.3 O(CH.sub.2).sub.2OMe F 1-209 CF.sub.3 O(CH.sub.2).sub.3OMe F 1-210 CF.sub.3 OCH.sub.2CONMe.sub.2 F 1-211 CF.sub.3 [1,4]dioxan-2-yl- F methoxy 1-212 CF.sub.3 O(CH.sub.2).sub.2OMe Cl 1-213 CF.sub.3 O(CH.sub.2).sub.3OMe Cl 1-214 CF.sub.3 OCH.sub.2CONMe.sub.2 Cl 1-215 CF.sub.3 [1,4]dioxan-2-yl- Cl methoxy 1-216 CF.sub.3 O(CH.sub.2).sub.2OMe Br 1-217 CF.sub.3 O(CH.sub.2).sub.3OMe Br 1-218 CF.sub.3 OCH.sub.2CONMe.sub.2 Br 1-219 CF.sub.3 [1,4]dioxan-2-yl- Br methoxy 1-220 CF.sub.3 O(CH.sub.2).sub.2OMe I 1-221 CF.sub.3 O(CH.sub.2).sub.3OMe I 1-222 CF.sub.3 OCH.sub.2CONMe.sub.2 I 1-223 CF.sub.3 [1,4]dioxan-2- I ylmethoxy 1-224 CF.sub.3 F SO.sub.2Me 1-225 CF.sub.3 F SO.sub.2Et 1-226 CF.sub.3 O(CH.sub.2).sub.2OMe SO.sub.2Me 1-227 CF.sub.3 O(CH.sub.2).sub.2OMe SO.sub.2Et 1-228 CF.sub.3 O(CH.sub.2).sub.3OMe SO.sub.2Me 1-229 CF.sub.3 O(CH.sub.2).sub.3OMe SO.sub.2Et 1-230 CF.sub.3 OCH.sub.2CONMe.sub.2 SO.sub.2Me 1-231 CF.sub.3 OCH.sub.2CONMe.sub.2 SO.sub.2Et 1-232 CF.sub.3 [1,4]dioxan-2- SO.sub.2Me ylmethoxy 1-233 CF.sub.3 [1,4]dioxan-2- SO.sub.2Et ylmethoxy 1-234 F SMe CF.sub.3 1-235 F SOMe CF.sub.3 1-236 Cl Me Cl 1-237 Cl OCH.sub.2CHCH.sub.2 Cl 1-238 Cl OCH.sub.2CHF.sub.2 Cl 1-239 Cl O(CH.sub.2).sub.2OMe Cl 1-240 Cl OCH.sub.2CONMe.sub.2 Cl 1-241 Cl O(CH.sub.2)-5-pyrrolidin- Cl 2-one 1-242 Cl SMe Cl 1-243 Cl SOMe Cl 1-244 Cl SO.sub.2Me Cl 1-245 Cl F SMe 1-246 Cl Cl SO.sub.2Me 1-247 Cl CO.sub.2Me SO.sub.2Me 1-248 Cl CONMe.sub.2 SO.sub.2Me 1-249 Cl CONMe(OMe) SO.sub.2Me 1-250 Cl CH.sub.2OMe SO.sub.2Me 1-251 Cl CH.sub.2OMe SO.sub.2Et 1-252 Cl CH.sub.2OEt SO.sub.2Me 1-253 Cl CH.sub.2OEt SO.sub.2Et 1-254 Cl CH.sub.2OCH.sub.2CHF.sub.2 SO.sub.2Me 1-255 Cl CH.sub.2OCH.sub.2CF.sub.3 SO.sub.2Me 1-256 Cl CH.sub.2OCH.sub.2CF.sub.3 SO.sub.2Et 1-257 Cl CH.sub.2OCH.sub.2CF.sub.2CHF.sub.2 SO.sub.2Me 1-258 Cl CH.sub.2OcPentyl SO.sub.2Me 1-259 Cl CH.sub.2PO(OMe).sub.2 SO.sub.2Me 1-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO.sub.2Me oxazol-3-yl 1-262 Cl 4,5-dihydro-1,2- SO.sub.2Et oxazol-3-yl 1-263 Cl 5-cyanomethyl-4,5- SO.sub.2Me dihydro-1,2-oxazol-3-yl 1-264 Cl 5-cyanomethyl-4,5- SO.sub.2Et dihydro-1,2-oxazol-3-yl 1-265 Cl 5-(methoxymethyl)- SO.sub.2Et 4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl 5-(methoxymethyl)- SO.sub.2Et 5-methyl-4,5-dihydro- 1,2-oxazol-3-yl 1-267 Cl CH.sub.2O- SO.sub.2Me tetrahydrofuran-3-yl 1-268 Cl CH.sub.2O- SO.sub.2Et tetrahydrofuran-3-yl 1-269 Cl CH.sub.2OCH.sub.2- SO.sub.2Me tetrahydrofuran-2-yl 1-270 Cl CH.sub.2OCH.sub.2- SO.sub.2Et tetrahydrofuran-2-yl 1-271 Cl CH.sub.2OCH.sub.2- SO.sub.2Me tetrahydrofuran-3-yl 1-272 Cl CH.sub.2OCH.sub.2- SO.sub.2Et tetrahydrofuran-3-yl 1-273 Cl OMe SO.sub.2Me 1-274 Cl OMe SO.sub.2Et 1-275 Cl OEt SO.sub.2Me 1-276 Cl OEt SO.sub.2Et 1-277 Cl Oi-Pr SO.sub.2Me 1-278 Cl Oi-Pr SO.sub.2Et 1-279 Cl O(CH.sub.2).sub.2OMe SO.sub.2Me 1-280 Cl O(CH.sub.2).sub.4OMe SO.sub.2Me 1-281 Cl O(CH.sub.2).sub.4OMe SO.sub.2Et 1-282 Cl O(CH.sub.2).sub.3OMe SO.sub.2Me 1-283 Cl O(CH.sub.2).sub.3OMe SO.sub.2Et 1-284 Cl O(CH.sub.2).sub.2OMe SO.sub.2Me 1-285 Cl O(CH.sub.2).sub.2OMe SO.sub.2Et 1-286 Cl [1,4]dioxan-2- SO.sub.2Me ylmethoxy 1-287 Cl [1,4]dioxan-2- SO.sub.2Et ylmethoxy 1-288 Cl OCH.sub.2(CO)NMe.sub.2 SO.sub.2Me 1-289 Cl OCH.sub.2(CO)NMe.sub.2 SO.sub.2Et 1-290 Cl SMe SO.sub.2Me 1-291 Cl SOMe SO.sub.2Me 1-292 Br OMe Br 1-293 Br O(CH.sub.2).sub.2OMe Br 1-294 Br O(CH.sub.2).sub.2OMe SO.sub.2Me 1-295 Br O(CH.sub.2).sub.2OMe SO.sub.2Et 1-296 Br O(CH.sub.2).sub.3OMe SO.sub.2Me 1-297 Br O(CH.sub.2).sub.3OMe SO.sub.2Et 1-298 Br O(CH.sub.2).sub.4OMe SO.sub.2Me 1-299 Br O(CH.sub.2).sub.4OMe SO.sub.2Et 1-300 Br [1,4]dioxan-2- SO.sub.2Me ylmethoxy 1-301 Br [1,4]dioxan-2- SO.sub.2Et ylmethoxy 1-302 I O(CH.sub.2).sub.2OMe SO.sub.2Me 1-303 I O(CH.sub.2).sub.2OMe SO.sub.2Et 1-304 I O(CH.sub.2).sub.3OMe SO.sub.2Me 1-305 I O(CH.sub.2).sub.3OMe SO.sub.2Et 1-306 I O(CH.sub.2).sub.4OMe SO.sub.2Me 1-307 I O(CH.sub.2).sub.4OMe SO.sub.2Et 1-308 I [1,4]dioxan-2- SO.sub.2Me ylmethoxy 1-309 I [1,4]dioxan-2- SO.sub.2Et ylmethoxy 1-310 OMe SMe CF.sub.3 1-311 OMe SOMe CF.sub.3 1-312 OMe SO.sub.2Me CF.sub.3 1-313 OMe SOEt CF.sub.3 1-314 OMe SO.sub.2Et CF.sub.3 1-315 OMe S(CH.sub.2).sub.2OMe CF.sub.3 1-316 OMe SO(CH.sub.2).sub.2OMe CF.sub.3 1-317 OMe SO.sub.2(CH.sub.2).sub.2OMe CF.sub.3 1-318 OMe SMe Cl 1-319 OMe SOMe Cl 1-320 OMe SO.sub.2Me Cl 1-321 OMe SEt Cl 1-322 OMe SOEt Cl 1-323 OMe SO.sub.2Et Cl 1-324 OMe S(CH.sub.2).sub.2OMe Cl 1-325 OMe SO(CH.sub.2).sub.2OMe Cl 1-326 OMe SO.sub.2(CH.sub.2).sub.2OMe Cl 1-327 OCH.sub.2c-Pr SMe CF.sub.3 1-328 OCH.sub.2c-Pr SOMe CF.sub.3 1-329 OCH.sub.2c-Pr SO.sub.2Me CF.sub.3 1-330 OCH.sub.2c-Pr SEt CF.sub.3 1-331 OCH.sub.2c-Pr SOEt CF.sub.3 1-332 OCH.sub.2c-Pr SO.sub.2Et CF.sub.3 1-333 OCH.sub.2c-Pr S(CH.sub.2).sub.2OMe CF.sub.3 1-334 OCH.sub.2c-Pr SO(CH.sub.2).sub.2OMe CF.sub.3 1-335 OCH.sub.2c-Pr SO.sub.2(CH.sub.2).sub.2OMe CF.sub.3 1-336 OCH.sub.2c-Pr SMe Cl 1-337 OCH.sub.2c-Pr SOMe Cl 1-338 OCH.sub.2c-Pr SO.sub.2Me Cl 1-339 OCH.sub.2c-Pr SEt Cl 1-340 OCH.sub.2c-Pr SOEt Cl 1-341 OCH.sub.2c-Pr SO.sub.2Et Cl 1-342 OCH.sub.2c-Pr S(CH.sub.2).sub.2OMe Cl 1-343 OCH.sub.2c-Pr SO(CH.sub.2).sub.2OMe Cl 1-344 OCH.sub.2c-Pr SO.sub.2(CH.sub.2).sub.2OMe Cl 1-345 OCH.sub.2c-Pr SMe SO.sub.2Me 1-346 OCH.sub.2c-Pr SOMe SO.sub.2Me 1-347 OCH.sub.2c-Pr SO.sub.2Me SO.sub.2Me 1-348 OCH.sub.2c-Pr SEt SO.sub.2Me 1-349 OCH.sub.2c-Pr SOEt SO.sub.2Me 1-350 OCH.sub.2c-Pr SO.sub.2Et SO.sub.2Me 1-351 OCH.sub.2c-Pr S(CH.sub.2).sub.2OMe SO.sub.2Me 1-352 OCH.sub.2c-Pr SO(CH.sub.2).sub.2OMe SO.sub.2Me 1-353 OCH.sub.2c-Pr SO.sub.2(CH.sub.2).sub.2OMe SO.sub.2Me 1-354 SO.sub.2Me F CF.sub.3 1-355 SO.sub.2Me NH.sub.2 CF.sub.3 1-356 SO.sub.2Me NHEt Cl 1-357 SMe SEt F 1-358 SMe SMe F 1-359 SMe SMe CF.sub.3 1-360 SMe SOMe CF.sub.3 1-361 SMe SO.sub.2Me CF.sub.3 1-362 SMe SMe Cl 1-363 SMe SMe Br 1-364 Cl Ac CF.sub.3 1-365 Cl Ac SO.sub.2Me 1-366 Cl C(O)cPr CF.sub.3 1-367 Cl C(O)cPr SO.sub.2Me 1-368 Cl CH.sub.2SMe CF.sub.3 1-369 Cl CH.sub.2S(O)Me CF.sub.3 1-370 Cl CH.sub.2SO.sub.2Me CF.sub.3 1-371 Cl CH.sub.2SMe SO.sub.2Me 1-372 Cl CH.sub.2S(O)Me SO.sub.2Me 1-373 Cl CH.sub.2SO.sub.2Me SO.sub.2Me 1-374 Cl CHNOMe CF.sub.3 1-375 Cl CHNOMe SO.sub.2Me 1-376 Cl 4,5-dihydro-1,2- CF.sub.3 oxazol-5-yl, 1-377 Cl 4,5-dihydro-1,2- SO.sub.2Me oxazol-5-yl, 1-378 Cl 3-methyl-4,5-dihydro- CF.sub.3 1,2-oxazol-5-yl 1-379 Cl 3-methyl-4,5-dihydro- SO.sub.2Me 1,2-oxazol-5-yl 1-380 Cl vinyl CF.sub.3 1-381 Cl vinyl SO.sub.2Me 1-382 Cl CO.sub.2Me CF.sub.3 1-383 Cl CO.sub.2Me SO.sub.2Me 1-384 Cl SMe CF.sub.3 1-385 Cl S(O)Me CF.sub.3 1-386 Cl SO.sub.2Me CF.sub.3 1-387 Cl SO.sub.2Me SO.sub.2Me 1-388 Cl SMe Me 1-389 Cl SOMe Me 1-390 Cl SO.sub.2Me Me 1-391 Cl 1H-1,2,4-triazol-1-yl CF.sub.3 1-392 Cl 1H-1,2,3-triazol-1-yl CF.sub.3 1-393 Cl 2H-1,2,3-triazol-2-yl CF.sub.3 1-394 Cl 1H-pyrazol-1-yl CF.sub.3 1-395 Cl 1H-4-chloropyrazol-1-yl CF.sub.3 1-396 Cl 1H-3-bromopyrazol- CF.sub.3 1-yl 1-397 Cl 1H-4-trifluoromethyl- CF.sub.3 pyrazol-1-yl 1-398 Cl pyrolidin-2-on-1-yl CF.sub.3 1-399 Cl morpholin-3-on-4-yl CF.sub.3 1-400 Cl 1,2-thiazolidine-1,1- CF.sub.3 dioxid-2-yl 1-401 Br 1H-1,2,4-triazol-1-yl CF.sub.3 1-402 Br 1H-1,2,3-triazol-1-yl CF.sub.3 1-403 Br 2H-1,2,3-triazol-2-yl CF.sub.3 1-404 Br 1H-pyrazol-1-yl CF.sub.3 1-405 Br 1H-4-chloropyrazol-1-yl CF.sub.3 1-406 Br 1H-3-bromopyrazol- CF.sub.3 1-yl 1-407 Br 1H-4-trifluoromethyl- CF.sub.3 pyrazol-1-yl 1-408 Br pyrolidin-2-on-1-yl CF.sub.3 1-409 Br morpholin-3-on-4-yl CF.sub.3 1-410 Br 1,2-thiazolidine-1,1- CF.sub.3 dioxid-2-yl 1-411 CH.sub.2OMe 1H-1,2,4-triazol-1-yl CF.sub.3 1-412 CH.sub.2OMe 1H-1,2,3-triazol-1-yl CF.sub.3 1-413 CH.sub.2OMe 2H-1,2,3-triazol-2-yl CF.sub.3 1-414 CF.sub.3 OCH.sub.2CH.sub.2F CF.sub.3 1-415 CF.sub.3 OMe CF.sub.3 1-416 CF.sub.3 SMe CF.sub.3 1-417 CF.sub.3 SOMe CF.sub.3 1-418 CF.sub.3 SO.sub.2Me CF.sub.3 1-419 CF.sub.3 1H-pyrazol-1-yl CF.sub.3 1-420 Me SMe Et 1-421 Me SOMe Et 1-422 Me SO.sub.2Me Et 1-423 Me 1H-pyrazol-1-yl Et 1-424 Me OCH.sub.2CH.sub.2F Et 1-425 Me OMe Et 1-426 Me Ac CF.sub.3 1-427 Me Ac SO.sub.2Me 1-428 Me C(O)cPr CF.sub.3 1-429 Me C(O)cPr SO.sub.2Me 1-430 Me CH.sub.2SMe CF.sub.3 1-431 Me CH.sub.2S(O)Me CF.sub.3 1-432 Me CH.sub.2SO.sub.2Me CF.sub.3 1-433 Me CH.sub.2SMe SO.sub.2Me 1-434 Me CH.sub.2S(O)Me SO.sub.2Me 1-435 Me CH.sub.2SO.sub.2Me SO.sub.2Me 1-436 Me CHNOMe CF.sub.3 1-437 Me CHNOMe SO.sub.2Me 1-438 Me 4,5-dihydro-1,2- CF.sub.3 oxazol-5-yl, 1-439 Me 4,5-dihydro-1,2- SO.sub.2Me oxazol-5-yl, 1-440 Me 3-methyl-4,5-dihydro- CF.sub.3 1,2-oxazol-5-yl 1-441 Me 3-methyl-4,5-dihydro- SO.sub.2Me 1,2-oxazol-5-yl 1-442 Me vinyl CF.sub.3 1-443 Me vinyl SO.sub.2Me 1-444 Me CO.sub.2Me CF.sub.3 1-445 Me CO.sub.2Me SO.sub.2Me 1-446 Cl SMe CF.sub.3 1-447 Cl SOMe CF.sub.3 1-448 Cl SO.sub.2Me CF.sub.3 1-449 Et SEt CF.sub.3 1-450 Et SOEt CF.sub.3 1-451 Et SO.sub.2Et CF.sub.3

(37) TABLE-US-00002 TABLE 2 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 2 comprises 451 compounds (2-1 to 2-451) in which X, Y and Z are defined in Table 1. embedded image

(38) TABLE-US-00003 TABLE 3 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 3 comprises 451 compounds (3-1 to 3-451) in which X, Y and Z are defined in Table 1. embedded image

(39) TABLE-US-00004 TABLE 4 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R6 is ethyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 4 comprises 451 compounds (4-1 to 4-451) in which X, Y and Z are defined in Table 1. embedded image

(40) TABLE-US-00005 TABLE 5 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 5 comprises 451 compounds (5-1 to 5-451) in which X, Y and Z are defined in Table 1. embedded image

(41) TABLE-US-00006 TABLE 6 Compounds of the general formula (I) according to the invention, where A is A1, B is N, R6 is ethyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 6 comprises 451 compounds (6-1 to 6-451) in which X, Y and Z are defined in Table 1. 0embedded image

(42) TABLE-US-00007 TABLE 7 Compounds of the general formula (I) according to the invention, where A is A1, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 7 comprises 451 compounds (7-1 to 7-451) in which X, Y and Z are defined in Table 1. embedded image

(43) TABLE-US-00008 TABLE 8 Compounds of the general formula (I) according to the invention, where A is A1, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 8 comprises 451 compounds (8-1 to 8-451) in which X, Y and Z are defined in Table 1. embedded image

(44) TABLE-US-00009 TABLE 9 Compounds of the general formula (I) according to the invention, where A is A1, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 9 comprises 451 compounds (9-1 to 9-451) in which X, Y and Z are defined in Table 1. embedded image

(45) TABLE-US-00010 TABLE 10 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 10 comprises 451 compounds (10-1 to 10-451) in which X, Y and Z are defined in Table 1. embedded image

(46) TABLE-US-00011 TABLE 11 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 11 comprises 451 compounds (11-1 to 11-451) in which X, Y and Z are defined in Table 1. embedded image

(47) TABLE-US-00012 TABLE 12 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 12 comprises 451 compounds (12-1 to 12-451) in which X, Y and Z are defined in Table 1. embedded image

(48) TABLE-US-00013 TABLE 13 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 13 comprises 451 compounds (13-1 to 13-451) in which X, Y and Z are defined in Table 1. embedded image

(49) TABLE-US-00014 TABLE 14 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 14 comprises 451 compounds (14-1 to 14-451) in which X, Y and Z are defined in Table 1. embedded image

(50) TABLE-US-00015 TABLE 15 Compounds of the general formula (I) according to the invention, where A is A2, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 15 comprises 451 compounds (15-1 to 15-451) in which X, Y and Z are defined in Table 1. embedded image

(51) TABLE-US-00016 TABLE 16 Compounds of the general formula (I) according to the invention, where A is A2, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 16 comprises 451 compounds (16-1 to 16-451) in which X, Y and Z are defined in Table 1. 0embedded image

(52) TABLE-US-00017 TABLE 17 Compounds of the general formula (I) according to the invention, where A is A2, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 17 comprises 451 compounds (17-1 to 17-451) in which X, Y and Z are defined in Table 1. embedded image

(53) TABLE-US-00018 TABLE 18 Compounds of the general formula (I) according to the invention, where A is A2, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 18 comprises 451 compounds (18-1 to 18-451) in which X, Y and Z are defined in Table 1. embedded image

(54) TABLE-US-00019 TABLE 19 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 19 comprises 451 compounds (19-1 to 19-451) in which X, Y and Z are defined in Table 1. embedded image

(55) TABLE-US-00020 TABLE 20 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 20 comprises 451 compounds (20-1 to 20-451) in which X, Y and Z are defined in Table 1. embedded image

(56) TABLE-US-00021 TABLE 21 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 20 comprises 451 compounds (20-1 to 20-451) in which X, Y and Z are defined in Table 1. embedded image

(57) TABLE-US-00022 TABLE 22 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 22 comprises 451 compounds (22-1 to 22-451) in which X, Y and Z are defined in Table 1. embedded image

(58) TABLE-US-00023 TABLE 23 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 23 comprises 451 compounds (23-1 to 23-451) in which X, Y and Z are defined in Table 1. embedded image

(59) TABLE-US-00024 TABLE 24 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 24 comprises 451 compounds (24-1 to 24-451) in which X, Y and Z are defined in Table 1. embedded image

(60) TABLE-US-00025 TABLE 25 Compounds of the general formula (I) according to the invention, where A is A3, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 25 comprises 451 compounds (25-1 to 25-451) in which X, Y and Z are defined in Table 1. embedded image

(61) TABLE-US-00026 TABLE 26 Compounds of the general formula (I) according to the invention, where A is A3, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 26 comprises 451 compounds (26-1 to 26-451) in which X, Y and Z are defined in Table 1. 0embedded image

(62) TABLE-US-00027 TABLE 27 Compounds of the general formula (I) according to the invention, where A is A3, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 27 comprises 451 compounds (27-1 to 27-451) in which X, Y and Z are defined in Table 1. embedded image

(63) TABLE-US-00028 TABLE 28 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 28 comprises 451 compounds (28-1 to 28-451) in which X, Y and Z are defined in Table 1. embedded image

(64) TABLE-US-00029 TABLE 29 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 29 comprises 451 compounds (29-1 to 29-451) in which X, Y and Z are defined in Table 1. embedded image

(65) TABLE-US-00030 TABLE 30 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 30 comprises 451 compounds (30-1 to 30-451) in which X, Y and Z are defined in Table 1. embedded image

(66) TABLE-US-00031 TABLE 31 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 31 comprises 451 compounds (31-1 to 31-451) in which X, Y and Z are defined in Table 1. embedded image

(67) TABLE-US-00032 TABLE 32 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 32 comprises 451 compounds (32-1 to 32-451) in which X, Y and Z are defined in Table 1. embedded image

(68) TABLE-US-00033 TABLE 33 Compounds of the general formula (I) according to the invention, where A is A4, B is N, R.sup.6 is ethyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 33 comprises 451 compounds (33-1 to 33-451) in which X, Y and Z are defined in Table 1. embedded image

(69) TABLE-US-00034 TABLE 34 Compounds of the general formula (I) according to the invention, where A is A4, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Et, W is CY and V is hydrogen. Table 34 comprises 451 compounds (34-1 to 34-451) in which X, Y and Z are defined in Table 1. embedded image

(70) TABLE-US-00035 TABLE 35 Compounds of the general formula (I) according to the invention, where A is A4, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2Me, W is CY and V is hydrogen. Table 35 comprises 451 compounds (35-1 to 35-451) in which X, Y and Z are defined in Table 1. embedded image

(71) TABLE-US-00036 TABLE 36 Compounds of the general formula (I) according to the invention, where A is A4, B is CH, R.sup.6 is methyl, R is CH(Me)OCO.sub.2-c-hexyl, W is CY and V is hydrogen. Table 36 comprises 451 compounds (36-1 to 36-451) in which X, Y and Z are defined in Table 1. 0embedded image

(72) TABLE-US-00037 TABLE 37 Compounds of the general formula (I) according to the invention, where A is A1, B is N, W is CY and V is hydrogen and R, R.sup.6, X and Z have the definitions specified in Table 37 embedded image Physical data No. X Z R.sup.6 R (.sup.1H NMR, DMSO-d.sub.6, 400 MHz) 10-1 Cl CF.sub.3 Me CH(Me)OCO.sub.2Et 10-2 Cl CF.sub.3 Me CH(Me)OCO.sub.2Me 10-3 Cl CF.sub.3 Me CH(Me)OCO.sub.2-c-hexyl 10-4 Cl CF.sub.3 Et CH(Me)OCO.sub.2Et 10-5 Cl CF.sub.3 Et CH(Me)OCO.sub.2Me 10-6 Cl CF.sub.3 Et CH(Me)OCO.sub.2-c-hexyl 10-7 Br CF.sub.3 Me CH(Me)OCO.sub.2Et 10-8 Br CF.sub.3 Me CH(Me)OCO.sub.2Me 10-9 Br CF.sub.3 Me CH(Me)OCO.sub.2-c-hexyl 10-10 Br CF.sub.3 Et CH(Me)OCO.sub.2Et 10-11 Br CF.sub.3 Et CH(Me)OCO.sub.2Me 10-12 Br CF.sub.3 Et CH(Me)OCO.sub.2-c-hexyl 10-13 Me CF.sub.3 Me CH(Me)OCO.sub.2Et 10-14 Me CF.sub.3 Me CH(Me)OCO.sub.2Me 10-15 Me CF.sub.3 Me CH(Me)OCO.sub.2-c-hexyl 10-16 Me CF.sub.3 Et CH(Me)OCO.sub.2Et 10-17 Me CF.sub.3 Et CH(Me)OCO.sub.2Me 10-18 Me CF.sub.3 Et CH(Me)OCO.sub.2-c-hexyl 10-19 CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2Et 10-20 CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2Me 10-21 CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2-c-hexyl 10-22 CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2Et 10-23 CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2Me 10-24 CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2-c-hexyl 10-25 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2Et 10-26 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2Me 10-27 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Me CH(Me)OCO.sub.2-c-hexyl 10-28 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2Et 10-29 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2Me 10-30 CH.sub.2OCH.sub.2CH.sub.2OMe CF.sub.3 Et CH(Me)OCO.sub.2-c-hexyl

(73) TABLE-US-00038 TABLE 38 Compounds of the general formula (I) according to the invention, where A is A2, B is N, W is CY and V is hydrogen. Table 38 comprises 30 compounds (38-1 to 38-30) in which R, R.sup.6, X and Z are as defined in Table 37. embedded image

(74) TABLE-US-00039 TABLE 39 Compounds of the general formula (I) according to the invention, where A is A3, B is N, W is CY and V is hydrogen. Table 39 comprises 30 compounds (39-1 to 39-30) in which R, R.sup.6, X and Z are as defined in Table 37. embedded image

(75) TABLE-US-00040 TABLE 40 Compounds of the general formula (I) according to the invention, where A is A4, B is N, W is CY and V is hydrogen. Table 40 comprises 30 compounds (40-1 to 40-30) in which R, R.sup.6, X and Z are as defined in Table 37. embedded image

(76) The abbreviations used mean:

(77) TABLE-US-00041 Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl Bn = benzyl Bu = butyl c = cyclo

B. FORMULATION EXAMPLES

(78) a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) 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 ball mill to a fineness of below 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of the formula (I) and/or salts thereof, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, 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. f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, 25 parts by weight of a compound of the formula (I), 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol 17 parts by weight of calcium carbonate and 50 parts by weight of water, 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

(79) 1. Pre-Emergence Herbicidal Action Against Harmful Plants

(80) 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). Here, for example, the compounds Nos. 1-384, 1-390, 3-384, 5-384, 19-384, 9-390, 21-384, 23-384 and 28-390, at an application rate of 320 g/ha, each show an activity of at least 80% against Stellaria media and Amaranthus retroflexus.

(81) 2. Post-Emergence Herbicidal Action Against Harmful Plants

(82) Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil 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). Here, for example, the compounds Nos. 1-384, 1-390, 3-384, 5-384, 19-384, 9-390, 21-384, 23-384, 28-390 and 32-384, at an application rate of 80 g/ha, each show an activity of at least 80% against Stellaria media and Veronica persica.

(83) 3. Comparative Experiment in Pre-Emergence

(84) For comparative purposes, the herbicidal activity of some compounds according to the invention and the most structurally similar compounds known from the prior art were tested.

(85) TABLE-US-00042 Herbicidal activity Compound Dosage [g/ha] against POLCO No. 1-390, inventive 320 100% No. 4-634, from WO 320 70% 2012/028579 No. 19-390, inventive 320 100% No. 4-634, from WO 320 70% 2012/028579 No. 28-390, inventive 320 90% No. 4-634, from WO 320 70% 2012/028579 No. 1-390, inventive 320 100% No. 3-040, from WO 320 70% 2014/126070 No. 28-390, inventive 320 90% No. 3-040, from WO 320 70% 2014/126070 No. 21-384, inventive 320 100% No. 4-638, from WO 320 50% 2012/028579 No. 23-384, inventive 320 90% No. 4-638, from WO 320 50% 2012/028579 No. 32-384, inventive 320 70% No. 4-638, from WO 320 50% 2012/028579

(86) The experiments show, by way of example, the superior herbicidal activity of the compounds according to the invention on the harmful plant Polygonum convolvulus (POLCO).