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BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES

20200331866 · 2020-10-22

    Inventors

    Cpc classification

    International classification

    Abstract

    The present invention relates to benzamide compounds of formula (I), the N-oxides and the salts thereof (I), where the variables are as defined in the claims and the description. The invention also relates to compositions comprising such compounds and to the use of such compounds for controlling unwanted vegetation.

    ##STR00001##

    Claims

    1. A compound of formula I, ##STR00129## wherein Q is selected from the group consisting of radicals of the formulae Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4; ##STR00130## where # in formulae Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 indicates the point of attachment to the nitrogen atom; R.sup.1 is selected from the group consisting of cyano, halogen, nitro, C.sub.1-C.sub.8-alkyl, 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.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.8-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, C.sub.1-C.sub.6-haloalkoxy, and R.sup.1bS(O).sub.kZ; R.sup.2a is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylamino, di-C.sub.1-C.sub.6-alkylamino, C.sub.3-C.sub.10-cycloalkyl and C.sub.3-C.sub.10-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the alkyl, alkoxy, alkenyl, alkynyl and cycloalkyl parts of the eight aforementioned radicals are unsubstituted, partially or completely halogenated, or substituted by 1 or 2 radicals R.sup.2f and where the cycloalkyl parts may also be fused to a benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 radicals R.sup.21 which are identical or different, R.sup.2a may also be selected from the group consisting of 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 R.sup.21 which are identical or different; R.sup.2b is selected from the group consisting of 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.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the alkyl, alkenyl, alkynyl and cycloalkyl parts of the five aforementioned radicals are unsubstituted, partially or completely halogenated, or substituted by 1 or 2 radicals R.sup.21; R.sup.2b may also be selected from the group consisting of 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 R.sup.21 which are identical or different; or R.sup.2a and R.sup.2b, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6-, 7- or 8-membered, saturated or partially unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and where the heterocyclic radical is unsubstituted or carries 1, 2, 3 or 4 groups R.sup.2d or carries 1 group R.sup.2e and 0, 1, 2 or 3 groups R.sup.2d, R.sup.2c is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylamino, di-C.sub.1-C.sub.6-alkylamino, C.sub.3-C.sub.10-cycloalkyl and C.sub.3-C.sub.10-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the alkyl, alkenyl, alkynyl and cycloalkyl parts of the seven aforementioned radicals are unsubstituted, partially or completely halogenated or substituted by 1 or 2 radicals R.sup.2f, and where the cycloalkyl parts may also be fused to a benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 radicals R.sup.21 which are identical or different, R.sup.2c may also be selected from the group consisting of 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 R.sup.21 which are identical or different; R.sup.2d are identical or different and selected from the group consisting of halogen, CN, 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 two groups R.sup.2d which are bound to adjacent carbon atoms may form together a fused benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.21 which are identical or different; R.sup.2e is selected from the group consisting of O, OH, R.sup.4bS(O).sub.kZ.sup.4, R.sup.4cC(O)Z.sup.4, R.sup.4dOC(O)Z.sup.4, R.sup.4eR.sup.4fNC(O)Z.sup.4, R.sup.4g R.sup.4hNZ.sup.4 and R.sup.4eR.sup.4fNS(O).sub.2Z.sup.4; R.sup.2f is selected from the group consisting of OH, CN, NH.sub.2, SH, SCN, nitro, tri(C.sub.1-C.sub.4-alkyl)silyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, R.sup.3eR.sup.3fN, R.sup.3cC(O), HOC(O)R.sup.3dOC(O), R.sup.3dSC(O), R.sup.3eR.sup.3fNC(O), R.sup.3eR.sup.3fNNR.sup.3hC(O), R.sup.3cC(S), R.sup.3dOC(S), R.sup.3dSC(S), R.sup.3eR.sup.3fNC(S), R.sup.3cS(O).sub.n, R.sup.3cS(O).sub.2O, R.sup.3dOS(O).sub.2, R.sup.3eR.sup.3fNS(O).sub.2, R.sup.3cC(O)NR.sup.3g, R.sup.3dOC(O)NR.sup.3g, R.sup.3eR.sup.3fNC(O)NR.sup.3g, R.sup.3eR.sup.3fNNR.sup.3hC(O)NR.sup.3g, R.sup.3dOS(O).sub.2NR.sup.3g, R.sup.3eR.sup.3fNS(O).sub.2NR.sup.3g, R.sup.3cC(O)NR.sup.3gC(O), R.sup.3dOC(O)NR.sup.3gC(O), R.sup.3eR.sup.3fNC(O)NR.sup.3gC(O), R.sup.3dOS(O).sub.2NR.sup.3gC(O), R.sup.3eR.sup.3fNS(O)NR.sup.3gC(O), R.sup.3cC(O)NR.sup.3gS(O).sub.2, R.sup.3dOC(O)NR.sup.3gS(O).sub.2, R.sup.3eR.sup.3fNC(O)NR.sup.3gS(O).sub.2, (OH).sub.2P(O), (C.sub.1-C.sub.4-alkoxy).sub.2P(O), R.sup.3dONCH, phenyl-X and heterocyclyl-X, where heterocyclyl in the last two mentioned radicals 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 R.sup.11 which are identical or different; R.sup.3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z.sup.3, 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.3, C.sub.3-C.sub.6-cycloalkenyl-Z.sup.3, C.sub.3-C.sub.10-cycloalkoxy-Z.sup.3, C.sub.3-C.sub.10-cycloalkyl-C.sub.1-C.sub.2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.4-cyanoalkyl, 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.3, C.sub.1-C.sub.8-haloalkoxy-Z.sup.3, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.3, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.3, C.sub.2-C.sub.8-alkenyloxy-Z.sup.3, C.sub.2-C.sub.8-alkynyloxy-Z.sup.3, C.sub.2-C.sub.8-haloalkenyloxy-Z.sup.3, C.sub.3-C.sub.8-haloalkynyloxy-Z.sup.3, R.sup.3bS(O).sub.kZ.sup.3, R.sup.3dC(O)Z.sup.3, R.sup.3dOC(O)Z.sup.3, R.sup.3dONCHZ.sup.3, R.sup.3eR.sup.3fNC(O)Z.sup.3 R.sup.3gR.sup.3hNZ.sup.3, R.sup.22C(O)OZ.sup.3, R.sup.25O C(O)OZ.sup.3, (R.sup.22).sub.2NC(O)OZ.sup.3, R.sup.25S(O).sub.2OZ.sup.3, R.sup.22OS(O).sub.2Z.sup.3, (R.sup.22).sub.2NS(O).sub.2Z.sup.3, R.sup.25O C(O)N(R.sup.22)Z.sup.3, (R.sup.22).sub.2NC(O)N(R.sup.22)Z.sup.3, (R.sup.22).sub.2NS(O).sub.2N(R.sup.22)Z.sup.3, (OH).sub.2P(O)Z.sup.3, (C.sub.1-C.sub.4-alkoxy).sub.2P(O)Z.sup.3, phenyl-Z.sup.3a, and heterocyclyl-Z.sup.3a, 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.3a and heterocyclyl-Z.sup.3a are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.21 which are identical or different; R.sup.4 is selected from the group consisting of hydrogen, halogen, cyano-Z.sup.1, C.sub.1-C.sub.8-alkyl, 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-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, 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 hydrogen, 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.1bS(O).sub.kZ.sup.1, phenoxy-Z.sup.1- and heterocyclyloxy-Z.sup.1, where heterocyclyloxy is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which is bound via an oxygen atom and 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.6a, R.sup.6b, R.sup.6c, R.sup.6d, 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.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, where the C.sub.3-C.sub.7-cycloalkyl groups of 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-alkynyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.3-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, RS(O).sub.nC.sub.1-C.sub.3-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; R.sup.7 is selected from the group consisting of hydyrogen, CN, NH.sub.2, 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 of 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-alkynyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.3-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, C.sub.1-C.sub.4-cyanoalkyl, R.sup.3bS(O).sub.kZ.sup.3b, R.sup.3cC(O)Z.sup.3b, R.sup.3dOC(O)Z.sup.3b, R.sup.3dONCHZ.sup.3b, R.sup.3eR.sup.3fNC(O)Z.sup.3b, R.sup.3gR.sup.3hNZ.sup.3b R.sup.22C(O)OZ.sup.3b, R.sup.25OC(O)OZ.sup.3b, (R.sup.22).sub.2NC(O)OZ.sup.3b, R.sup.25S(O).sub.2OZ.sup.3b, R.sup.22OS(O).sub.2Z.sup.3b, (R.sup.22).sub.2NS(O).sub.2Z.sup.3b, R.sup.25OC(O)N(R.sup.22)Z.sup.3b, (R.sup.22).sub.2NC(O)N(R.sup.22)Z.sup.3b, (R.sup.22).sub.2NS(O).sub.2N(R.sup.22)Z.sup.3b, (OH).sub.2P(O)Z.sup.3b, (C.sub.1-C.sub.4-alkoxy).sub.2P(O)Z.sup.3b, phenyl-Z.sup.3a, and heterocyclyl-Z.sup.3a, 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.3a and heterocyclyl-Z.sup.3a are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.21 which are identical or different; R.sup.11, R.sup.21, independently of each other, are selected from the group consisting of cyano, OH, halogen, nitro, 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.3-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-haloalkoxy, or two radicals R.sup.11 or R.sup.21, respectively, which are bound to the same carbon atom, may form together a group O, or two radicals R.sup.11 or R.sup.21, respectively, which are bound to adjacent carbon atoms, may form together a group selected from C.sub.3-C.sub.5-alkylene, OC.sub.2-C.sub.4-alkylene and O(C.sub.1-C.sub.3-alkylene)-O; Z.sup.1, Z.sup.3, Z.sup.4, independently of each other, are selected from the group consisting of a covalent bond and C.sub.1-C.sub.4-alkanediyl which is unsubstituted, partly or completely fluorinated; Z.sup.2 is a covalent bond or a bivalent radical selected from C.sub.1-C.sub.4-alkanediyl and C.sub.1-C.sub.4-alkanediyl-OC.sub.1-C.sub.4-alkanediyl, where in the two last-mentioned radicals the C.sub.1-C.sub.4-alkanediyl groups are linear and where the C.sub.1-C.sub.4-alkanediyl is unsubstituted, or is partly or completely fluorinated or substituted by 1, 2, 3 or 4 groups R.sup.z, Z.sup.3a 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; Z.sup.3b is selected from the group consisting of C.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.z are identical or different and 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.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.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-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, heterocyclyl and heterocyclylmethyl, where heterocyclyl in the last two mentioned radicals 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, heterocyclyl and heterocyclylmethyl 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.b, R.sup.1b, R.sup.3b, R.sup.4b, 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.3-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.3c, R.sup.4c, 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.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-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.3d, R.sup.4d, 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.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-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 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.3e, R.sup.3f, R.sup.4e, R.sup.4f, 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-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-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.3e and R.sup.3f or R.sup.4e and R.sup.4f, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or carries 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.3g, R.sup.4g, 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-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-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.3h, R.sup.4h, 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-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-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.3g and R.sup.3h or R.sup.4g and R.sup.4h, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered, saturated or partially unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or carries 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.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-Z.sup.1, phenyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-Z.sup.1, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, and heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, 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 cyano, halogen, nitro, thiocyanato, 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-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-Z.sup.1, phenyl-OC.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, heterocyclyl-Z.sup.1, heterocyclyl-N(R.sup.23)C.sub.1-C.sub.6-alkyl, heterocyclyl-OC.sub.1-C.sub.6-alkyl, and heterocyclyl-S(O).sub.nC.sub.1-C.sub.6-alkyl, 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 cyano, halogen, nitro, thiocyanato, 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; X is a covalent bond, O, S(O).sub.n or NR, where R is hydrogen or C.sub.1-C.sub.4-alkyl; k is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1 or 2; and R.sup.k has the meanings of R.sup.3c; an N-oxide or an agriculturally suitable salt thereof.

    2. The compound of claim 1, where Q is Q.sup.1.

    3. The compound of claim 1, where Q is Q.sup.2.

    4. The compound of claim 1, where Q is Q.sup.4.

    5. The compound of claim 1, where R.sup.1 is selected from the group consisting of halogen, nitro, cyano, 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-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1- and R.sup.1bS(O).sub.kZ.sup.1-.

    6. The compound of claim 5, where R.sup.1 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-alkoxy.

    7. The compound of claim 1, where R.sup.2a is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl, 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; and R.sup.2b 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, C.sub.1-C.sub.6-haloalkyl, 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.

    8. The compound of claim 1, where R.sup.2a and R.sup.2b, together with the nitrogen atom to which they are bound, form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from 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, OH, 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, where R.sup.2a is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 C.sub.1-C.sub.4-alkyl groups which are identical or different; and R.sup.2b is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl and C.sub.3-C.sub.6-cycloalkyl; or R.sup.2a and R.sup.2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N, and which is unsubstituted or carries 1, 2, 3 or 4 groups R.sup.2d which are selected from the group consisting of C.sub.1-C.sub.4-alkyl and fluorinated C.sub.1-C.sub.4-alkyl.

    10. The compound of claim 1, where R.sup.2c is hydrogen or C.sub.1-C.sub.4-alkyl, and is in particular hydrogen.

    11. The compound of claim 1, having one or more of the following features i) to v): i) R.sup.3 is selected from the group consisting of halogen, nitro, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.1-C.sub.8-haloalkoxy-Z.sup.3, and R.sup.3bS(O).sub.kZ.sup.3; ii) R.sup.4 is hydrogen or halogen; iii) R.sup.5 is hydrogen or halogen; iv) R.sup.6a, R.sup.6b, R.sup.6c, R.sup.6d, independently of each other, are selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, and phenyl; v) R.sup.7 is hydrogen.

    12. The compound of claim 1, where R.sup.3 is halogen.

    13. The compound of claim 1, where R.sup.4 is hydrogen.

    14. The compound of claim 1, where R.sup.5 is hydrogen or fluorine.

    15. The compound of claim 1, where R.sup.6a, R.sup.6b, R.sup.6c, R.sup.6d, independently of each other, are C.sub.1-C.sub.4-alkyl.

    16. The compound of claim 1, where R.sup.7 is hydrogen.

    17. The compound of claim 1, where Z.sup.2 is covalent bond.

    18. The compound of claim 1, which is selected from the compounds of formulae I.A, I.B and I.D ##STR00131## the N-oxides and the agriculturally suitable salts thereof.

    19. The compound of claim 18, where R.sup.1 is halogen, C.sub.1-C.sub.2-alkyl or C.sub.1-C.sub.2-alkoxy; R.sup.2a is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-methyl, fluorinated C.sub.1-C.sub.4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of halogen, methyl and methoxy; R.sup.2b is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-methyl and fluorinated C.sub.1-C.sub.4-alkyl; or R.sup.2a and R.sup.2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which is selected from the group consisting of 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R.sup.2d which are selected from the group consisting of C.sub.1-C.sub.4-alkyl and fluorinated C.sub.1-C.sub.4-alkyl; R.sup.2c is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl; R.sup.3 is selected from the group consisting of halogen, C.sub.1-C.sub.2-alkyl, fluorinated C.sub.1-C.sub.2-alkyl, SC.sub.1-C.sub.2-alkyl, S(O).sub.2C.sub.1-C.sub.2-alkyl, S(O).sub.2C.sub.1-C.sub.2-alkyl, S-(fluorinated C.sub.1-C.sub.2-alkyl), S(O)-(fluorinated C.sub.1-C.sub.2-alkyl) and S(O).sub.2-(fluorinated C.sub.1-C.sub.2-alkyl); R.sup.4 is hydrogen, R.sup.5 is hydrogen or fluorine; and R.sup.6a, R.sup.6b and R.sup.6d, independently of each other, are selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; and where in particular R.sup.1 is halogen, C.sub.1-C.sub.2-alkyl or C.sub.1-C.sub.2-alkoxy; R.sup.2a is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, fluorinated C.sub.1-C.sub.4-alkyl and phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 methyl groups; R.sup.2b is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl and C.sub.3-C.sub.6-cycloalkyl; or R.sup.2a and R.sup.2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring; R.sup.2c is hydrogen; R.sup.3 is halogen; R.sup.4 is hydrogen, R.sup.5 is hydrogen or fluorine; and R.sup.6a, R.sup.6b and R.sup.6d, independently of each other, are C.sub.1-C.sub.4-alkyl.

    20. 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.

    21. (canceled)

    22. A method for controlling unwanted vegetation comprising allowing a herbicidally effective amount of at least one compound as claimed in claim 1 to act on plants, their seed, and/or their habitat.

    Description

    EXAMPLES

    [0774] The preparation of the compounds of formula I is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given. With appropriate modification of the starting materials, the procedures given in the examples below were used to obtain further compounds 1. The compounds obtained in this manner are listed in table C, together with physical data. The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.

    [0775] HPLC-MS: high performance liquid chromatography coupled with mass spectrometry;

    [0776] MeOD: Tetradeuteromethanol

    [0777] MS: Mass spectroscopy

    [0778] THF: tetrahydrofuran

    [0779] TFA: trifluoroacetic acid

    [0780] s: singlet

    [0781] d: doublet

    [0782] t: triplet

    [0783] m: multiplet

    [0784] HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile+0.1% TFA/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40 C., flow rate 1.8 mL/min.

    [0785] MS: quadrupole electrospray ionization, 80 V (positive mode).

    [0786] HPLC column: Luna-C18(2) 5 m column (Phenomenex), 2.0*50 mm; mobile phase: acetonitrile+0.0625% TFA/water+0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 minutes at 40 C., flow rate 0.8 mL/min.

    MS: quadrupole electrospray ionization, 70 V (positive mode).

    Example 1: 4-Bromo-3-(diethylcarbamothioylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (compound formula (I.A.VII), where, R.SUP.1., R.SUP.2a., R.SUP.2b .and R.SUP.3 .are as defined in line 722 of table A

    [0787] ##STR00122##

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

    [0788] A solution of 3-amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (8.0 g, 24 mmol) in 500 ml THE was cooled to 0 C. and thiophosgene (3.2 g, 28 mmol) was added. The mixture was heated to reflux for 8 hours and stirred for additional 48 h at 22 C. The obtained crude solution of the isothiocyanate was used without further purification in step 2.

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

    [0789] An aliquot of the solution of 4-bromo-6-fluoro-3-isothiocyanato-2-methyl-N-(1-methyltetrazol-5-yl)benzamide in THE (containing ca. 400 mg of the isothiocyanate, 1.08 mmol) was treated with triethylamine (218 mg) and a solution of diethylamine (79 mg) in THE (5 ml). The mixture was stirred for 4 h at 22 C. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. The thus obtained solution was washed with 2N aqueous hydrochloric acid and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the remainder was purified by column chromatography to yield 164 mg of the product as a solid.

    [0790] .sup.1H NMR (400 MHz, MeOD), 7.50 (d, 1H), 4.05 (s, 3H), 3.7-3.9 (m, 4H), 2.35 (s, 3H), 1.3 (t, 6H).

    [0791] By analogy to the method described in the Example 1, the following compounds of formula (I.A.VII) according to Table C (examples 2 to 17), compounds of formula (I.A.VIII) according to Table D (examples 18 to 24), compounds of formula (I.A.I) according to Table E (examples 25 to 33), compounds of formula (I.B.VII) according to Table F (examples 34 and 35), and compounds of formula (I.D.VII) according to Table G (examples 36 to 38) were prepared:

    TABLE-US-00007 TABLE C I.A.VII [00123]embedded image cpd. no in table A R.sup.1 R.sup.2a R.sup.2b R.sup.3 MS (m/z) 1 722 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 444.0 2 644 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.3 Br 432.0 3 692 CH.sub.3 C.sub.6H.sub.5 CH.sub.3 Br 478.0 4 1088 CH.sub.3 [00124]embedded image Br 457.9 5 932 CH.sub.3 cyclopropyl cyclopropyl Br 470.0 6 656 CH.sub.3 CH(CH.sub.3).sub.2 CH.sub.3 Br 446.0 7 650 CH.sub.3 CH.sub.2CH.sub.2CH.sub.3 CH.sub.3 Br 446.0 8 746 CH.sub.3 cyclopropyl CH.sub.2CH.sub.3 Br 456.0 9 632 CH.sub.3 2,6-(CH.sub.3).sub.2C.sub.6H.sub.3 H Br 493.9 10 578 CH.sub.3 C(CH.sub.3).sub.3 H Br 445.9 11 608 CH.sub.3 C.sub.6H.sub.5 H Br 447.8 12 584 CH.sub.3 cyclopropyl H Br 427.8 13 1454 OCH.sub.3 phenyl CH(CH.sub.3).sub.2 Br 524.0 14 680 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.3 Br 486.0 15 758 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.2CH.sub.3 Br 500.0 16 752 CH.sub.3 CH.sub.2CHF.sub.2 CH.sub.2CH.sub.3 Br 482.0 17 674 CH.sub.3 CH.sub.2CHF.sub.2 CH.sub.3 Br 468.0

    TABLE-US-00008 TABLE D I.A.VIII [00125]embedded image cpd. no in table A R.sup.1 R.sup.2a R.sup.2b R.sup.3 MS (m/z) 18 932 CH.sub.3 cyclopropyl cyclopropyl Br 484.1 19 746 CH.sub.3 cyclopropyl CH.sub.2CH.sub.3 Br 470.1 20 644 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.3 Br 444.1 21 722 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 460.1 22 692 CH.sub.3 phenyl CH.sub.3 Br 492.1 23 770 CH.sub.3 phenyl CH.sub.2CH.sub.3 Br 506.1 24 902 CH.sub.3 phenyl CH(CH.sub.3).sub.2 Br 520.1

    TABLE-US-00009 TABLE E I.A.I [00126]embedded image cpd. no in table A R.sup.1 R.sup.2a R.sup.2b R.sup.3 MS (m/z) 25 679 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.3 Cl 422.0 26 757 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.2CH.sub.3 Cl 436.0 27 673 CH.sub.3 CH.sub.2CHF.sub.2 CH.sub.3 Cl 404.0 28 751 CH.sub.3 CH.sub.2CHF.sub.2 CH.sub.2CH.sub.3 Cl 418.1 29 680 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.3 Br 468.0 30 758 CH.sub.3 CH.sub.2CF.sub.3 CH.sub.2CH.sub.3 Br 482.0 31 121 Cl CH.sub.2CHF.sub.2 CH.sub.3 Cl 424.0 32 127 Cl CH.sub.2CF.sub.3 CH.sub.3 Cl 442.0 33 205 Cl CH.sub.2CF.sub.3 CH.sub.2CH.sub.3 Cl 420.0

    TABLE-US-00010 TABLE F I.B.VII [00127]embedded image cpd. no in table A R.sup.1 R.sup.2a R.sup.2b R.sup.3 MS (m/z) 34 722 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 442.9 35 644 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.3 Br 430.8

    TABLE-US-00011 TABLE G I.D.VII [00128]embedded image cpd. no in table A R.sup.1 R.sup.2a R.sup.2b R.sup.3 MS (m/z) 36 722 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 444.0 37 692 CH.sub.3 phenyl CH.sub.3 Br 480.0 38 644 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.3 Br 431.9

    Use Examples

    [0792] The herbicidal activity of the compounds of formula I was demonstrated by the following greenhouse experiments:

    [0793] 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.

    [0794] 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. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.

    [0795] 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 by means of finely distributing nozzles. 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.

    [0796] Depending on the species, the plants were kept at 10-25 C. or 20-25 C., respectively. 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.

    [0797] 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.

    [0798] Test series 1:

    [0799] At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against:

    [0800] ALOMY (Alopecurus myosuroiedes)

    [0801] ECHCG (Echinocloa crus-galli)

    [0802] SETFA (Setaria faberi)

    [0803] In test series 1, compounds of examples 1, 2, 4, 5, 6, 7, 8, 14, 16, 17, 18, 19, 21, 25, 26, 27, 28, 29, 30, 31, 32, 33 showed >85% control of ALOMY. The compound of example 34 showed 80% control of ALOMY.

    [0804] In test series 1, compounds of examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 36, 37 showed >85% control of ECHCG. The compound of example 34 showed 80% control of ECHCG.

    [0805] In test series 1, compounds of examples 1, 2, 4, 5, 7, 8, 9, 10, 14, 16, 17, 18, 25, 26, 27, 28, 29, 30, 31, 32, 33 showed >85% control of SETFA.