Benzamide compounds and their use as herbicides

Abstract

The invention relates to a compound of formula I, ##STR00001##
an N-oxide or an agriculturally suitable salt thereof, wherein the variables are as defined in the specification, and their use as herbicides.

Claims

1. A compound of formula I, ##STR00179## an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.1 or Q.sup.2 or Q.sup.3 or Q.sup.4, ##STR00180## R.sup.1 is selected from the group consisting of halogen, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, nitro, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, cyano-Z.sup.1, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.10-cycloalkyl-Z.sup.1, C.sub.2-C.sub.8-haloalkenyl, C.sub.3-C.sub.8-haloalkynyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkylthio-Z.sup.1, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, R.sup.1bS(O).sub.kZ.sup.1, phenoxy-Z.sup.1 and heterocyclyloxy-Z.sup.1, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.11, which are identical or different; R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2cZ.sup.2; R.sup.3 is selected from the group consisting of hydrogen, halogen, hydroxy-Z.sup.2, nitro, C.sub.1-C.sub.4-nitroalkyl, cyano, C.sub.1-C.sub.4-cyanoalkyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.10-cycloalkyl-Z.sup.2, C.sub.3-C.sub.10-cycloalkoxy-Z.sup.2, where the C.sub.3-C.sub.10-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.8-haloalkyl, C.sub.2-C.sub.8-haloalkenyl, C.sub.3-C.sub.8-haloalkynyl, C.sub.1-C.sub.8-alkoxy-Z.sup.2, C.sub.1-C.sub.8-haloalkoxy-Z.sup.2, C.sub.3-C.sub.10-cycloalkyl-C.sub.1-C.sub.2-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.2, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkylthio-Z.sup.2, C.sub.2-C.sub.8-alkenyloxy-Z.sup.2, C.sub.2-C.sub.8-alkynyloxy-Z.sup.2, C.sub.2-C.sub.8-haloalkenyloxy-Z.sup.2, C.sub.3-C.sub.8-haloalkynyloxy-Z.sup.2, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.2, (tri-C.sub.1-C.sub.4-alkyl)silyl-Z.sup.2, R.sup.2b-S(O).sub.k-Z.sup.2, R.sup.2c-C(O)Z.sup.2, R.sup.2dOC(O)Z.sup.2, R.sup.2dONCHZ.sup.2, R.sup.2eR.sup.2fNC(O)Z.sup.2, R.sup.2gR.sup.2hNZ.sup.2, phenyl-Z.sup.2a, heterocyclyl-Z.sup.2a, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z.sup.2a and heterocy-clyl-Z.sup.2a are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.21, which are identical or different, rhodano, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-alkyl, OC(O)R.sup.22, OC(O)OR.sup.25, OC(O)N(R.sup.22).sub.2, OSO.sub.2R.sup.25, SO.sub.2OR.sup.22, SO.sub.2N(R.sup.22).sub.2, SO.sub.2N(R.sup.22)C(O)R.sup.22, SO.sub.2N(R.sup.22)C(O)OR.sup.25, SO.sub.2N(R.sup.22)C(O)N(R.sup.22).sub.2, N(R.sup.22)C(O)OR.sup.25, N(R.sup.22)C(O)N(R.sup.22).sub.2, N(R.sup.22)S(O).sub.2OR.sup.22, N(R.sup.22)S(O).sub.2N(R.sup.22).sub.2, C(O)N(R.sup.22)OR.sup.22, C(O)N(R.sup.22)N(R.sup.22).sub.2, C(O)N(R.sup.22)C(O)R.sup.22, C(O)N(R.sup.22)C(O)OR.sup.25, C(O)N(R.sup.22)C(O)N(R.sup.22).sub.2, C(O)N(R.sup.22)SO.sub.2R.sup.25, C(O)N(R.sup.22)SO.sub.2OR.sup.22, C(O)N(R.sup.22)SO.sub.2N(R.sup.22).sub.2, P(O)(OH).sub.2, P(O)(OC.sub.1-C.sub.4-alkyl).sub.2, C.sub.1-C.sub.6-alkyl-OC(O)R.sup.22, C.sub.1-C.sub.6-alkyl-OC(O)OR.sup.25, C.sub.1-C.sub.6-alkyl-OC(O)N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-OSO.sub.2R.sup.25, C.sub.1-C.sub.6-alkyl-SO.sub.2OR.sup.22, C.sub.1-C.sub.6-alkyl-SO.sub.2N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-SO.sub.2N(R.sup.22)C(O)R.sup.22, C.sub.1-C.sub.6-alkyl-SO.sub.2N(R.sup.22)C(O)OR.sup.25, C.sub.1-C.sub.6-alkyl-SO.sub.2N(R.sup.22)C(O)N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-N(R.sup.22)C(O)OR.sup.25, C.sub.1-C.sub.6-alkyl-N(R.sup.22)C(O)N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-N(R.sup.22)S(O).sub.2OR.sup.22, C.sub.1-C.sub.6-alkyl-N(R.sup.22)S(O).sub.2N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)OR.sup.22, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)C(O)R.sup.22, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)C(O)OR.sup.25, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)C(O)N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)SO.sub.2R.sup.25, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)SO.sub.2OR.sup.22, C.sub.1-C.sub.6-alkyl-C(O)N(R.sup.22)SO.sub.2N(R.sup.22).sub.2, C.sub.1-C.sub.6-alkyl-P(O)(OH).sub.2 and C.sub.1-C.sub.6-alkyl-P(O)(OC.sub.1-C.sub.4-alkyl).sub.2; R.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.8-alkyl, cyano-Z.sup.1, nitro, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-haloalkyl, C.sub.1-C.sub.3-alkylamino, C.sub.1-C.sub.3-dialkylamino, C.sub.1-C.sub.3-alkylamino-S(O).sub.k, C.sub.1-C.sub.3-alkylcarbonyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkylthio-Z.sup.1, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, R.sup.1b-S(O).sub.k-Z.sup.1, phenoxy-Z.sup.1 and heterocyclyloxy-Z.sup.1, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.11, which are identical or different; R.sup.5 is selected from the group consisting of halogen, cyano-Z.sup.1, nitro, C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-haloalkyl, C.sub.1-C.sub.3-alkylamino, C.sub.1-C.sub.3-dialkylamino, C.sub.1-C.sub.3-alkylamino-S(O).sub.k, C.sub.1-C.sub.3-alkylcarbonyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkylthio-Z.sup.1, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, R.sup.1b-S(O).sub.k-Z.sup.1, phenoxy-Z.sup.1 and heterocyclyloxy-Z.sup.1, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.11, which are identical or different; R.sup.6 is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, 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.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, R.sup.b-S(O).sub.nC.sub.1-C.sub.3-alkyl, R.sup.cC(O)C.sub.1-C.sub.3-alkyl, R.sup.dOC(O)C.sub.1-C.sub.3-alkyl, R.sup.eR.sup.fNC(O)C.sub.1-C.sub.3-alkyl, R.sup.gR.sup.hNC.sub.1-C.sub.3-alkyl, phenyl-Z and heterocyclyl-Z, where heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R, which are identical or different; R, R.sup.11, R.sup.21 independently of each other are selected from the group consisting of halogen, NO.sub.2, CN, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-halocycloalkyl, 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.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.7-cycloalkoxy and C.sub.1-C.sub.6-haloalkyloxy, or two radicals R, R.sup.11 or R.sup.21 bound to the same carbon atom together may form a group O; Z, Z.sup.1, Z.sup.2 independently of each other are selected from the group consisting of a covalent bond and C.sub.1-C.sub.4-alkanediyl; Z.sup.2a is selected from the group consisting of a covalent bond, C.sub.1-C.sub.4-alkanediyl, OC.sub.1-C.sub.4-alkanediyl, C.sub.1-C.sub.4-alkanediyl-O and C.sub.1-C.sub.4-alkanediyl-OC.sub.1-C.sub.4-alkanediyl; R.sup.b, R.sup.1b, R.sup.2b independently of each other are selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, 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, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.c, R.sup.2c independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkyl-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.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4S(O).sub.nC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-dialkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.d, R.sup.2d independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkyl-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.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4S(O).sub.nC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-dialkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.2c, R.sup.2d together with the nitrogen atom, to which they are bound may form a 4, -5-, 6- or 7-membered, saturated or unsaturated cyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.e, R.sup.f independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenylene, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or R.sup.e, R.sup.f together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.2e, R.sup.2f independently of each other have the meanings given for R.sup.e, R.sup.f; R.sup.g is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenylene, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.h is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, 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.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkylcarbonyl, a radical C(O)R.sup.k, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or R.sup.g, R.sup.h together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of O, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.2g, R.sup.2h independently of each other have the meanings given for R.sup.g, R.sup.h; R.sup.k has the meanings given for R.sup.c; R.sup.22 is selected from the group consisting of 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.3-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.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, phenyl, phenyl-C.sub.1-C.sub.6-alkyl, heteroaryl, heteroaryl-C.sub.1-C.sub.6-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.6-alkyl, phenyl-OC.sub.1-C.sub.6-alkyl, heteroaryl-OC.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heteroaryl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heteroaryl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, where the 15 aforementioned phenyl, phenyl-C.sub.1-C.sub.6-alkyl, heteroaryl, heteroaryl-C.sub.1-C.sub.6-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.6-alkyl, phenyl-OC.sub.1-C.sub.6-alkyl, heteroaryl-OC.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heteroaryl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heteroaryl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl radicals are substituted by s residues selected from the group consisting of nitro, halogen, cyano, rhodano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C(O)OR.sup.23, C(O)N(R.sup.23).sub.2, OR.sup.23, N(R.sup.23).sub.2, S(O).sub.nR.sup.24, S(O).sub.2OR.sup.23, S(O).sub.2N(R.sup.23).sub.2 and R.sup.23OC.sub.1-C.sub.6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; R.sup.23 is selected from the group consisting of 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-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl and phenyl; R.sup.24 is selected from the group consisting of 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-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl and phenyl; R.sup.25 is selected from the group consisting of 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-cycloalkenylene, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, phenyl, phenyl-C.sub.1-C.sub.6-alkyl, heteroaryl, heteroaryl-C.sub.1-C.sub.6-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.6-alkyl, phenyl-OC.sub.1-C.sub.6-alkyl, heteroaryl-OC.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heteroaryl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heteroaryl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, where the 15 aforementioned phenyl, phenyl-C.sub.1-C.sub.6-alkyl, heteroaryl, heteroaryl-C.sub.1-C.sub.6-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.6-alkyl, phenyl-OC.sub.1-C.sub.6-alkyl, heteroaryl-OC.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heteroaryl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heteroaryl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl radicals are substituted by s residues selected from the group consisting of nitro, halogen, cyano, rhodano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C(O)OR.sup.23, C(O)N(R.sup.23).sub.2, OR.sup.23, N(R.sup.23).sub.2, S(O).sub.nR.sup.24, S(O).sub.2OR.sup.23, S(O).sub.2N(R.sup.23).sub.2 and R.sup.23OC.sub.1-C.sub.6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; s is 0, 1, 2, or 3.

2. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.1.

3. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.2.

4. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.3.

5. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.4.

6. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.1 is selected from the group consisting of halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.k and C.sub.1-C.sub.4-haloalkyl-S(O).sub.k, wherein k is 0 or 2.

7. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.2 is R.sup.2cR.sup.2dNC(O)NHZ.sup.2.

8. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Z.sup.2 in R.sup.2 is a covalent bond and R.sup.2c and R.sup.2d independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4S(O).sub.nC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-dialkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy.

9. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy and R.sup.2b-S(O).sub.k, wherein k is 0, 1 or 2 and wherein R.sup.2b is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

10. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.4 is hydrogen.

11. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.5 is fluorine.

12. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R.sup.6 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl.

13. A composition comprising at least one compound as claimed in claim 1, an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary, which is customary for formulating crop protection compounds.

14. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound as claimed in claim 1, an N-oxide or an agriculturally suitable salt thereof to act on plants, their seed and/or their habitat.

15. The method of claim 14, wherein Q is Q.sup.1.

16. The method of claim 14, wherein Q is Q.sup.2.

17. The method of claim 14, wherein Q is Q.sup.3.

18. The method of claim 14, wherein Q is Q.sup.4.

19. The method of claim 14, wherein R.sup.1 is selected from the group consisting of halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.k and C.sub.1-C.sub.4-haloalkyl-S(O).sub.k, wherein k is 0 or 2.

20. The method of claim 14, wherein R.sup.2 is R.sup.2cR.sup.2dNC(O)NHZ.sup.2.

21. The method of claim 14, wherein Z.sup.2 in R.sup.2 is a covalent bond and R.sup.2c and R.sup.2d independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4S(O).sub.nC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-dialkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy.

22. The method of claim 14, wherein R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy and R.sup.2b-S(O).sub.k, wherein k is 0, 1 or 2 and wherein R.sup.2b is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

23. The method of claim 14, wherein R.sup.4 is hydrogen.

24. The method of claim 14, wherein R.sup.5 is fluorine.

25. The method of claim 14, wherein R.sup.6 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl.

26. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q.sup.1; R.sup.1 is selected from the group consisting of halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.k and C.sub.1-C.sub.4-haloalkyl-S(O).sub.k, wherein k is 0 or 2; R.sup.2 is R.sup.2cR.sup.2dNC(O)NHZ.sup.2, where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c and R.sup.2d, independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the C.sub.3-C.sub.7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-S(O).sub.nC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-dialkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyloxy and R.sup.2b-S(O).sub.k, wherein k is 0, 1 or 2 and wherein R.sup.2b is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; R.sup.4 is hydrogen; R.sup.5 is fluorine; and R.sup.6 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl.

27. The compound of claim 26, an N-oxide or an agriculturally suitable salt thereof, where R.sup.1 is selected from the group consisting of halogen and C.sub.1-C.sub.4-alkyl; R.sup.2 is R.sup.2cR.sup.2dNC(O)NHZ.sup.2, where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, and C.sub.1-C.sub.4-haloalkyl; and R.sup.2d is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, and C.sub.1-C.sub.4-haloalkyl; R.sup.3 is selected from the group consisting of halogen and C.sub.1-C.sub.4-haloalkyl; and R.sup.6 is C.sub.1-C.sub.4-alkyl.

Description

I. SYNTHESIS EXAMPLES

(1) With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the table that follows, together with physical data.

(2) The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.

(3) HPLC-MS=high performance liquid chromatography coupled with mass spectrometry; HPLC column: 15 RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm;

(4) mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40C, flow rate 1.8 ml/min.

(5) MS: quadrupole electrospray ionization, 80 V (positive mode)

(6) AcSK: potassium thioacetate

(7) p-HPLC=preparative HPLC

Example 1: Preparation of 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide of the Formula I.A-3.85, Entry 7

Step 1: methyl 3-amino-4-bromo-6-fluoro-2-methyl-benzoate

(8) ##STR00038##

(9) Commercially available methyl 3-amino-6-fluoro-2-methyl-benzoate (CAS [848678-60-4, 30.0 g, 0.16 mol) was dissolved in anhydrous DMF (220 ml) and treated in portions with NBS (N-bromosuccinimide) at room temperature. The reaction was slightly exothermic and was kept below 29 C. via cooling. The reaction mixture was stirred overnight, concentrated in vacuo and treated with methyl-tert-butyl ether (MTBE, 450 ml) and water (400 ml) and extracted a second time with MTBE (200 ml). The combined organic phases were washed with water (3250 ml) and brine (1250 ml), dried over magnesium sulfate and the solvent evaporated in vacuo to yield the product (41.1 g, 96% yield). LC-MS (M+H): 263.8

Step 2: methyl 4-bromo-6-fluoro-3-isocyanato-2-methyl-benzoate

(10) ##STR00039##

(11) Triphosgene (bis(trichloromethyl) carbonate, 53.2 g, 0.18 mol) was dissolved in toluene (350 ml) and treated with a solution of methyl 3-amino-4-bromo-6-fluoro-2-methyl-benzoate (23.5 g, 0.09 mol) in 100 ml of toluene. Temperature was increased stepwise to reflux with evolution of gas observed starting at a temperature of approx. 85 C. Reflux was kept for 6 h and the reaction mixture stirred overnight at room temperature. Afterwards the reaction mixture was evaporated in vacuo to leave the product (15.5 g, 99%) as an orange solid which was used without further purification for the next step.

Step 3: methyl 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoate

(12) ##STR00040##

(13) Methyl 4-bromo-6-fluoro-3-isocyanato-2-methyl-benzoate (15.00 g, 52.07 mmol) was dissolved in THF (180 ml) and ethyl(methyl)amine (3.45 g, 59.88 mmol) was added dropwise at room temperature. The temperature increased to a maximum of 29 C. Stirring was continued overnight at RT and the solvent afterwards evaporated in vacuo. The remainder was triturated with methyl acetate several times. This gave in several portions solids yielding in total to 17.83 g (98%) of the title compound. LC-MS (M+H): 346.7

Step 4: 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoic acid

(14) ##STR00041##

(15) Methyl 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoate (13.95 g (40.18 mmol) was suspended in THF (250 ml) and treated with a solution of lithium hydroxide (2.89 g, 120.58 mmol) in water (50 ml) and stirred at 50 C. for 25 h. The amount of THF was reduced by concentration in vacuo and the remaining aqueous phase was washed with ethyl acetate. The pH value was adjusted to ca. pH 1-2 by addition of hydrochloric acid (1 molar). The product precipitated upon this treatment and additional cooling with ice and was filtered off. Drying in vacuo yielded 10.55 of a solid (79%) of the title compound which was used without further purification in the next step.

Step 5: 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

(16) ##STR00042##

(17) 1-Methyltetrazol-5-amine (2.38 g, 24.0 mmol) was dissolved in anhydrous THF (120 ml) and cooled to 70 C. under argon atmosphere. A solution of methyl lithium in THF (3 molar, 24.0 mmol) was added dropwise at this temperature and the reaction mixture warmed up to 0 C. At this temperature the solution prepared in the following manner was added dropwise: 4-Bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoic acid (4.00 g, 12.0 mmol) was suspended in dichloromethane (DCM, 100 ml) and cooled to 78 C. under argon atmosphere and DAST (diethlyamino sulfur trifluoride, 2.13 g, 13.2 mmol) was added via syringe. Cooling was continued for 2.5 h and the reaction mixture afterwards allowed to warm up to RT for 15 h. The solvent was evaporated in vacuo and re-dissolved in anhydrous THF (80 ml).

(18) After addition if this solution stirring was continued at RT for 3 h and the reaction mixture carefully quenched by addition of water (60 ml). The major amounts of THF were evaporated in vacuo and the remainder adjusted to a pH value of ca. 1 by addition of aqueous hydrochloric acid (2 molar). Extraction with ethyl acetate (360 ml), drying of the combined organic phases with magnesium sulfate and evaporation of the solvent yielded crude product which was purified by column chromatography to yield the title compound (1.10 g, 22%).

(19) .sup.1H NMR (400 MHz, MeOD), 7.5 (d, 1H), 4.05 (s, 3H), 3.45 (m, 2H), 3.05 (s, 3H), 2.35 (s, 3H), 1.2 (t, 3H)

Example 2: Preparation of 4-bromo-3-(diethylcarbamoylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide of the Formula I.A-15.85, Entry 5

Step 1: 6-Fluoro-2-methyl-3-nitro-benzoyl chloride

(20) ##STR00043##

(21) Commercially available 6-fluoro-2-methyl-3-nitro-benzoic acid (38.4 g, 193 mmol) was suspended in toluene (300 ml) and treated with thionyl chloride (21 g, 1.5 equiv.) and 2 drops of DMF and slightly warmed up while adding thionyl chloride (32.1 g, 1.4 equiv.) keeping the reaction temperature in a range of ca. 55-65 C. Gas evolved and the mixture became clear. The mixture was heated up to reflux for additional 3 hours. Evaporation in vacuo yielded the title compound in quantitative yield (42.3 g). This product was used for the next step without further purification.

Step 2: 6-Fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-nitro-benzamide

(22) ##STR00044##

(23) 1-Methyltetrazol-5-amine (40.2 g, 406 mmol) was dissolved in anhydrous THF (850 ml) and cooled to 75 C. under argon atmosphere. A solution of methyl lithium in THF (2.3 molar, ca. 0.4 mol) was added dropwise at this temperature and the reaction mixture warmed up to ca. 0 C. At this temperature a solution of 6-fluoro-2-methyl-3-nitro-benzoyl chloride in THF (42.3 g, 50 ml) was added keeping the temperature around 0 C. Afterwards the reaction mixture was warmed up to room temperature and stirred overnight. The reaction mixture was quenched with aqueous hydrochloric acid (200 ml, 2M) and phases separated, the organic phase dried over magnesium sulphate and the solvent evaporated to yield the crude product (42.8 g) as a solid which was used without further purification in the next step.

Step 3: 3-Amino-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

(24) ##STR00045##

(25) 6-Fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-nitro-benzamide (48.2 g, 172 mmol) was suspended in methanol (1 l) at RT. A solution of SnCl.sub.22 H.sub.2O (134 g, 593 mmol) in conc. hydrochloric acid (37% in water) was added in a temperature range of 45-65 C. and heated up to reflux for 2.5 h. After cooling down, the methanol was evaporated, 1 l water added and sodium hydroxide solution (50% in water) to adjust the pH to a value of about 5-6. Extraction with several portions of ethyl acetate (total of ca. 3 l), drying and evaporation led to 40.7 g (163 mmol, ca. 95% yield) of the product.

Step 4: 3-Amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

(26) ##STR00046##

(27) 3-Amino-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (20.5 g, 81.9 mmol) was suspended at RT in glacial acetic acid (260 I) and heated to 65 C. to dissolve the amine. A solution of bromine (1 equiv.) in glacial acetic acid (40 ml) was added dropwise over a period of ca. 1.5 h and the mixture stirred thereafter for additional 1.5 h. The glacial acetic acid was evaporated in vacuo and water added at ice cooling (300 ml) and stirred at this temperature for 1 h. The formed precipitate was filtered off and dried in vacuo to yield 24.5 g (91%) of the product as a lilac solid.

Step 5: 4-bromo-3-(diethylcarbamoylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

(28) ##STR00047##

(29) Remark: The reaction with triphosgene leads in most cases predominantly to the formation of the imidoylchlorides as intermediates instead of the respective carboxamides, but can be converted back into a carboxamide after the formation of the urea (i.e. after addition of the respective amine to the isocyanate) by careful reaction with hydroxide solution as described in the following procedure:

(30) A solution of 3-amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (10.0 g, 30.0 mmol) in n-butyl acetate was added dropwise to a solution of triphosgene (13.5 g, 45.5 mmol) in the same solvent (ca. 200 ml) and heated to reflux until the evolution of gas ceased. The solvent was evaporated in vacuo and the remainder dissolved in THF and diethyl amine added (2.34 g, ca. 1.1 equiv.) and stirred overnight. The pH value was adjusted to ca. 9 by addition of sodium hydroxide solution (2 molar in water) and stirred again overnight. Further hydroxide solution was added to reach a pH of 13 and stirring continued for 1 d. Water was added, the THF evaporate in vacuo, the aqueous phase washed with methyl tert-butyl ether and adjusted with hydrochloric acid solution to pH 5. Extraction with ethyl acetate yielded a crude product which was crystallized from ethyl acetate/methanol to yield the product (11.4 g, ca. 89%). 1H NMR (400 MHz, d6-DMSO), 12 (br s, 1H), 8.0 (s, 1H), 7.70 (d, 1H), 4.00 (s, 3H), 3.3 (m, 4H), 2.25 (s, 6H), 1.15 (t, 3H).

Example 3: 3-Amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide as an Example for the Preparation of Intermediates Leading to Compounds with Q.SUP.2., Q.SUP.3 .and Q.SUP.4

(31) ##STR00048##

(32) 3-Amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide (3.2 g, 13 mmol), prepared from 6-fluoro-2-methyl-3-nitro-benzoic acid similar to Example 2, step 1-3 (cf. above), was dissolved in anhydrous DMF (40 ml) and treated in portions with NBS (N-bromo succinimide) at room temperature. The reaction was slightly exothermic. The reaction mixture was stirred for 4.5 h, concentrated in vacuo and treated with methyl-tert-butyl ether (MTBE, 100 ml) and water whereupon a solid was formed and separated via filtration.

(33) The remainder was tried in vacuo and the organic phase separately dried over magnesium sulfate and the solvent evaporated in vacuo. This combined to a total von 3.67 g of the title compound.

(34) The compounds according to Tables I to IV below were prepared in accordance with the methods described above:

(35) TABLE-US-00003 TABLE I compounds of the formula I as shown above wherein Q is Q.sup.1, R.sup.4 is H and R.sup.5 is F no. entry acc. LC-MS no. table A R.sup.1 R.sup.3 R.sup.6 R.sup.2 (M + H) 1 I.A-1.9 Cl Cl CH.sub.3 376.1 2 Cl Cl CH.sub.3 0 390.1 3 Cl Cl CH.sub.3 474.1 (+Na.sup.+) 4 Cl Cl CH.sub.3 424.0 5 I.A- 15.85 CH.sub.3 Br CH.sub.3 428.0 6 CH.sub.3 Br CH.sub.3 388.0 7 I.A- 3.85 CH.sub.3 Br CH.sub.3 416.1 8 I.A- 1.85 CH.sub.3 Br CH.sub.3 401.9 9 CH.sub.3 Br CH.sub.3 401.9 10 CH.sub.3 Br CH.sub.3 416.0 11 I.A- 5.85 CH.sub.3 Br CH.sub.3 428.0 12 CH.sub.3 H CH.sub.3 0 308.1 13 I.A- 1.81 CH.sub.3 Cl CH.sub.3 356.0 14 I.A- 5.81 CH.sub.3 Cl CH.sub.3 384.1 15 I.A- 3.84 CH.sub.3 Cl CH.sub.2CH.sub.2OCH.sub.3 414.1 16 I.A- 3.81 CH.sub.3 Cl CH.sub.3 370.1 17 CH.sub.3 Cl CH.sub.3 356.0 18 I.A- 3.82 CH.sub.3 Cl C.sub.2H.sub.5 384.1 19 CH.sub.3 Cl C.sub.2H.sub.5 370.0 20 CH.sub.3 Cl CH.sub.2CH.sub.2OCH.sub.3 400.1 21 I.A- 3.86 CH.sub.3 Br C.sub.2H.sub.5 430.0 22 I.A- 3.88 CH.sub.3 Br CH.sub.2CH.sub.2OCH.sub.3 0 460.0 23 CH.sub.3 Cl CH.sub.2CH.sub.2OCH.sub.3 414.1 24 CH.sub.3 Cl CH.sub.3 370.0 25 CH.sub.3 Cl CH.sub.2CH.sub.2OCH.sub.3 386.2 26 I.A- 15.81 CH.sub.3 Cl CH.sub.3 384.2 27 CH.sub.3 Cl CH.sub.3 342.1 28 CH.sub.3 Br CH.sub.3 430.0 29 CH.sub.3 Br CH.sub.3 447.9 30 CH.sub.3 Br CH.sub.3 428.0 31 CH.sub.3 Br CH.sub.3 442.1 32 I.A- 13.85 CH.sub.3 Br CH.sub.3 0 444.0 33 CH.sub.3 Br CH.sub.3 374.0 34 I.A- 9.85 CH.sub.3 Br CH.sub.3 444.0 35 CH.sub.3 Br CH.sub.3 460.0 36 CH.sub.3 4-OCH.sub.3- phenyl CH.sub.3 442.2 37 CH.sub.3 Br CH.sub.3 459.2 38 CH.sub.3 Br CH.sub.3 474.2 39 CH.sub.3 Br CH.sub.3 451.9 40 I.A- 11.85 CH.sub.3 Br CH.sub.3 462.1 41 CH.sub.3 Br CH.sub.3 416.1 42 I.A- 5.85 CH.sub.3 Br CH.sub.3 0 426.0 43 CH.sub.3 Br CH.sub.3 413.9 44 CH.sub.3 Br CH.sub.3 442.1 45 CH.sub.3 Br CH.sub.3 454.0 46 CH.sub.3 Br CH.sub.3 445.0 47 CH.sub.3 Br CH.sub.3 454.0 48 CH.sub.3 Br CH.sub.3 442.0 49 CH.sub.3 Br CH.sub.3 473.1 50 CH.sub.3 Br CH.sub.3 472.1 51 CH.sub.3 Br CH.sub.3 471.1 52 CH.sub.3 Br CH.sub.3 00 458.0 53 CH.sub.3 Br CH.sub.3 01 456.0 54 CH.sub.3 Br CH.sub.3 02 442.0 55 CH.sub.3 Br CH.sub.3 03 471.1 56 CH.sub.3 Br CH.sub.3 04 483.1 57 CH.sub.3 Br CH.sub.3 05 441.1 58 CH.sub.3 Br CH.sub.3 06 492.0 59 CH.sub.3 Br CH.sub.3 07 470.1 60 CH.sub.3 Br CH.sub.3 08 460.0 61 CH.sub.3 Br CH.sub.3 09 496.1 62 CH.sub.3 Br CH.sub.3 0 482.0 63 CH.sub.3 Br CH.sub.3 472.0 64 CH.sub.3 Br CH.sub.3 506.0 65 CH.sub.3 Br CH.sub.3 504.1 66 CH.sub.3 Br CH.sub.3 468.1 67 CH.sub.3 Br CH.sub.3 477.0 68 CH.sub.3 Br CH.sub.3 496.1 69 CH.sub.3 Br CH.sub.3 498.1 70 CH.sub.3 Br CH.sub.3 454.0 71 I.A- 15.25 Cl CF.sub.3 CH.sub.3 438.1 72 CH.sub.3 Br CH.sub.3 0 498.1 73 CH.sub.3 Br CH.sub.3 456.0 74 CH.sub.3 Br CH.sub.3 456.0 75 CH.sub.3 Br CH.sub.3 425.9 76 CH.sub.3 Br CH.sub.3 472.0 77 CH.sub.3 Br CH.sub.3 472.0 78 CH.sub.3 Br CH.sub.3 500.0 79 CH.sub.3 Br CH.sub.3 472.1 80 CH.sub.3 Br CH.sub.3 546.0 81 CH.sub.3 Br CH.sub.3 512.0 82 CH.sub.3 Br CH.sub.3 0 508.0 83 Cl CF.sub.3 CH.sub.3 500.0 84 Cl Cl CH.sub.3 390.0 85 I.A- 15.9 Cl Cl CH.sub.3 404.0 86 Cl Cl CH.sub.3 428.0 87 CH.sub.3 Br CH.sub.3 486.0 88 CH.sub.3 Br CH.sub.3 445.0 89 CH.sub.3 Br CH.sub.3 545.9 90 CH.sub.3 Br CH.sub.3 554.0 91 CH.sub.3 Br CH.sub.3 504.0 92 CH.sub.3 Br CH.sub.3 0 443.8 93 CH.sub.3 Br CH.sub.3 458.0 94 CH.sub.3 Br CH.sub.3 580.0 95 CH.sub.3 Br CH.sub.3 580.0 96 CH.sub.3 Br CH.sub.3 531.9 97 CH.sub.3 Br CH.sub.3 479.9 98 CH.sub.3 Br CH.sub.3 559.0 99 I.A- 1.13 Cl Br CH.sub.3 422.0 100 I.A- 3.13 Cl Br CH.sub.3 436.0 101 CH.sub.3 Br CH.sub.3 442.0 102 CH.sub.3 Br CH.sub.3 0 482.1 103 I.A- 15.13 Cl Br CH.sub.3 449.8 104 Cl Br CH.sub.3 484.0 105 Cl Br CH.sub.3 474.0 106 OCH.sub.3 Br CH.sub.3 444.1 107 CH.sub.3 Br CH.sub.3 478.1 108 CH.sub.3 Br CH.sub.3 504.0 109 CH.sub.3 Br CH.sub.3 494.0 110 CH.sub.3 Br CH.sub.3 478.0 111 CH.sub.3 Br CH.sub.3 498.0 112 OCH.sub.3 Br CH.sub.3 0 429.8 113 OCH.sub.3 Br CH.sub.3 479.8 114 OCH.sub.3 Br CH.sub.3 467.9 115 CH.sub.3 Br CH.sub.3 498.0 116 I.A-3.9 Cl Cl CH.sub.3 390.0 117 I.A- 15.9 Cl Cl CH.sub.3 404.0 118 Cl Cl CH.sub.3 428.0 119 CH.sub.3 Br CH.sub.3 463.9 120 CH.sub.3 Br CH.sub.3 510.1

(36) TABLE-US-00004 TABLE II compounds of the formula I as shown above wherein Q is Q.sup.2, R.sup.4 is H and R.sup.5 is F no. acc. entry no. table A R.sup.1 R.sup.3 R.sup.6 R.sup.2 LC-MS (M + H) 1 I.B-3.85 CH.sub.3 Br CH.sub.3 415.0 2 CH.sub.3 Br CH.sub.3 0 462.9 3 I.B-15.85 CH.sub.3 Br CH.sub.3 426.9

(37) TABLE-US-00005 TABLE III compounds of the formula I as shown above wherein Q is Q.sup.3, R.sup.4 is H and R.sup.5 is F no. acc. entry no. table A R.sup.1 R.sup.3 R.sup.6 R.sup.2 LC-MS (M + H) 1 I.C-15.85 CH.sub.3 Br CH.sub.3 428.1 2 I.C-1.85 CH.sub.3 Br CH.sub.3 401.8 3 I.C-3.85 CH.sub.3 Br CH.sub.3 413.9 4 CH.sub.3 Br CH.sub.3 462.0 5 CH.sub.3 Br CH.sub.3 492.0

(38) TABLE-US-00006 TABLE IV compounds of the formula I as shown above wherein Q is Q.sup.4, R.sup.4 is H and R.sup.5 is F entry no. no. acc. table A R.sup.1 R.sup.3 R.sup.6 R.sup.2 LC-MS (M + H) 1 I.D-3.85 CH.sub.3 Br CH.sub.3 416.0 2 I.D-15.85 CH.sub.3 Br CH.sub.3 430.0

II. USE EXAMPLES

(39) The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

(40) The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

(41) For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted.

(42) This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.

(43) For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

(44) Depending on the species, the plants were kept at 10-25 C. or 20-25 C., respectively.

(45) The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

(46) Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.

(47) At an application rate of 250 g/ha the following compounds were tested in pre-emergence tests against AMARE (Amaranthus retroflexus), CHEAL (Chenopodium album) and ECHCG (Echinocloa crus-galli) and showed a control of >85%: Entries no. 1, 5, 7, 8, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 24, 26, 28, 31, 32, 33, 34.

(48) At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against

(49) ALOMY (Alopecurus myosuroiedes) and showed a control of >85%:

(50) Entries of Table I no. 1, 2, 5-8, 11, 13-16, 18, 21-22, 26. 28, 31, 34, 35, 39, 40 42-45, 47, 48, 50, 52-54, 58, 59, 62, 66-70, 73, 76-78, 84-86, 93, 99-100, 103-105, 115;

(51) Entries of Table II no. 1, 2;

(52) Entries of Table III no. 1;

(53) ECHCG (Echinocloa crus-galli) and showed a control of >85%:

(54) Entries Table I no. 1-3, 5-11, 13-24, 26, 28, 30-32, 34-35, 38-40, 42-45, 47-48, 50, 52-54, 58-59, 62-70, 72-74, 79, 84-87, 89-91, 93, 99, 100, 103-105, 115, 119.

(55) Entries of Table II no. 1, 3;

(56) AMARE (Amaranthus retroflexus) and showed a control of >85%:

(57) Entries Table I no. 1-11, 13-28, 31-39, 42-45, 47-48, 50, 52-54, 58-59, 62-70, 73, 84-86, 91, 93, 99, 100, 103-105, 115;

(58) Entries of Table II no. 1-3;

(59) CHEAL (Chenopodium album) and showed a control of >85%:

(60) Entries Table I no. 1-11, 13-29, 31-40, 42-45, 47-48, 50-54, 56-60, 62-70, 72-74, 79, 84-87, 89-91, 93, 99, 100, 103-105, 115, 119;

(61) Entries of Table II no. 1-3;

(62) Entries of Table III no. 1-3, 5;

(63) Entries of Table IV no. 1;