BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES

Abstract

The invention relates to benzamides of formula I,

##STR00001## wherein Q is Q.sup.1 or Q.sup.2 or Q.sup.3 or Q.sup.4,

##STR00002##

and their use as herbicides. In said formula I, R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2nZ.sup.2, both R.sup.4 and R.sup.5 are hydrogen, R.sup.1, R.sup.3 and R.sup.6 represent groups such as hydrogen, halogen or organic groups such as alkyl or phenyl. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

Claims

1. A compound of formula I, ##STR00132## wherein Q is Q.sup.1 or Q.sup.2 Or Q.sup.3 or Q.sup.4, ##STR00133## R.sup.1 is selected from the group consisting of cyano, halogen, nitro, C.sub.1-C.sub.8-alkyl, 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, R.sup.1bS(O).sub.kZ.sup.1; R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2nZ.sup.2; R.sup.3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy-Z.sup.2, nitro, 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.6-cycloalkenyl-Z.sup.2, C.sub.3-C.sub.10-cycloalkoxy-Z.sup.2, 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.2, C.sub.1-C.sub.8-haloalkoxy-Z.sup.2, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.2, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.4-alkoxy-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.8haloalkynyloxy-Z.sup.2, R.sup.2bS(O).sub.kZ.sup.2, R.sup.2cC(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, R.sup.22C(O)OZ.sup.2, R.sup.25OC(O)OZ.sup.2, (R.sup.22).sub.2NC(O)OZ.sup.2, R.sup.25S(O).sub.2OZ.sup.2, R.sup.22OS(O).sub.2Z.sup.2, (R.sup.22).sub.2NS(O).sub.2Z.sup.2, R.sup.25OC(O)N(R.sup.22)Z.sup.2, (R.sup.22).sub.2NC(O)N(R.sup.22)Z.sup.2, (R.sup.22).sub.2NS(O).sub.2N(R.sup.22)Z.sup.2, (OH).sub.2P(O)Z.sup.2, (C.sub.1-C.sub.4-alkoxy).sub.2P(O)Z.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 cyclic groups in phenyl-Z.sup.2a and heterocyclyl-Z.sup.2a are unsubstituted or substituted by 1, 2, 3 or 4 groups R.sup.21, which are identical or different; R.sup.4 is hydrogen; R.sup.5 is hydrogen; R.sup.6 is selected from the group consisting of cyano, 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, R.sup.bS(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.21 is selected from the group consisting of cyano, 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.21 bound to the same carbon atom together may form a group O; 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.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.2c 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.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.2d 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.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; or 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 heterocyclic radical, which may carry 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, 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.2n 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-cyanoalkyl, 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.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; R.sup.2e, R.sup.2f 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.2e, R.sup.2f 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 carry 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, 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 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.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.2h 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.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.2g, R.sup.2h 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 carry 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, 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, 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, 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, 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, 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; k is 0, 1 or 2; n is 0, 1 or 2; R.sup.k has the meanings of R.sup.2c; or an agriculturally suitable salt thereof; with the exception of Benzamide, 4-bromo-2-chloro-N-[1-(2-methoxyethyl)-1H-tetrazol-5-yl]-3-[[(methoxymethylamino)carbonyl]amino]-, CAS Registry Number: 1421777-21 0; Benzamide, 2,4-dichloro-N-[1-(2-methoxyethyl)-1H-tetrazol-5-yl]-3-[[(methoxymethylamino)carbonyl]amino]-, CAS Registry Number: 1421776-96-6; Benzamide, 2,4-dichloro-3-[[(methoxymethylamino)carbonyl]amino]-N-(1-phenyl-1H-tetrazol-5-yl)-, CAS Registry Number: 1361245-23-9; Benzamide, N-(1-ethyl-1H-tetrazol-5-yl)-2-methyl-3-[[[methyl(2-methylpropyl)amino]carbonyl]amino]-4-(methylsulfonyl)-, CAS Registry Number: 1361209-74-6; Benzamide, 2,4-dichloro-3-[[(dimethylamino)carbonyl]amino]-N-(1-methyl-1H-tetrazol-5-yl)-, CAS Registry Number: 1361139-93-6; Benzamide, 2,4-dichloro-3-[[(methoxymethylamino)carbonyl]amino]-N-(1-phenyl-1H-1,2,4-triazol-5-yl)-, CAS Registry Number: 1361103-06-1; Benzamide, 2,4-dichloro-N-(1-ethyl-1H-1,2,4-triazol-5-yl)-3-[[(methoxymethylamino)carbonyl]amino]-, CAS Registry Number: 1361040-89-2; Benzamide, N-(4-cyano-1,2,5-oxadiazol-3-yl)-2-methyl-3-[[[methyl(2-methylpropyl)amino]carbonyl]amino]-4-(methylsulfonyl)-, CAS Registry Number: 1279687-63-6; Benzamide, 2-methyl-3-[[[methyl(2-methylpropyl)amino]carbonyl]amino]-4-(methylsulfonyl)-N-[4-(trifluoromethyl)-1,2,5-oxadiazol-3-yl]-, CAS Registry Number: 1279679-31-0; Benzamide, N-[4-(1,1-dimethylethyl)-1,2,5-oxadiazol-3-yl]-2-methyl-3-[[[methyl(2-methylpropyl)amino] carbonyl]amino]-4-(methyl sulfonyl)-, CAS Registry Number: 1279665-87-0; Benzamide, N-[4-(chloromethyl)-1,2,5-oxadiazol-3-yl]-2-methyl-3-[[[methyl(2-methylpropyl)amino] carbonyl]amino]-4-(methyl sulfonyl)-, CAS Registry Number: 1279659-60-7; Benzamide, 2-methyl-3-[[[methyl(2-methylpropyl)amino]carbonyl]amino]-4-(methylsulfonyl)-N-(4-propyl-1,2,5-oxadiazol-3-yl)-, CAS Registry Number: 1279644-16-4; Benzamide, 2-methyl-N-[4-(1-methylethyl)-1,2,5-oxadiazol-3-yl]-3-[[[methyl(2-methylpropyl)amino] carbonyl]amino]-4-(methyl sulfonyl)-, CAS Registry Number: 1279635-24-3; Benzamide, N-(4-ethyl-1,2,5-oxadiazol-3-yl)-2-methyl-3-[[[methyl(2-methylpropyl)amino] carbonyl]amino]-4-(methyl sulfonyl)-, CAS Registry Number: 1279127-99-9; Benzamide, 2-methyl-3-[[[methyl(2-methylpropyl)amino]carbonyl]amino]-N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-, CAS Registry Number: 1279114-20-3.

2. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q.sup.1.

3. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q.sup.2.

4. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q.sup.3.

5. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q.sup.4.

6. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is selected from the group consisting of halogen, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-Z.sup.1, R.sup.1bS(O).sub.kZ.sup.1.

7. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2nZ.sup.2, where Z.sup.2 is a covalent bond and R.sup.2n is selected from the group consisting of hydrogen and C.sub.1-C.sub.6-alkyl.

8. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2nZ.sup.2, where Z.sup.2 is C.sub.1-C.sub.4-alkanediyl and R.sup.2n is selected from the group consisting of hydrogen and C.sub.1-C.sub.6-alkyl.

9. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where 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 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, 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.

10. The compound as claimed in claim 9, or an agriculturally suitable salt thereof, where Z.sup.2 in R.sup.2 is a covalent bond R.sup.2C is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl and C.sub.1-C.sub.4-haloalkyl and R.sup.2d is selected from the group consisting of C.sub.2-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.6-haloalkyl.

11. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Z.sup.2 in R.sup.2 is a covalent bond and R.sup.2c and 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 heterocyclic radical, which may carry 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, 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.

12. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.3 is selected from the group consisting of halogen, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-haloalkoxy, and R.sup.2b-S(O).sub.k.

13. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.3 is selected from the group consisting of halogen and C.sub.1-C.sub.2-haloalkyl.

14. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is methyl and R.sup.3 is selected from the group consisting of Cl, Br and CF.sub.3.

15. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is Cl and R.sup.3 is selected from the group consisting of Br and CF.sub.3.

16. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is C.sub.1-C.sub.2-alkyl, R.sup.3 is selected from the group consisting of halogen and C.sub.1-C.sub.2-haloalkyl and where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl and C.sub.1-C.sub.4-haloalkyl, and R.sup.2d is selected from the group consisting of C.sub.2-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.4-haloalkyl.

17. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is methyl and R.sup.3 is selected from the group consisting of Cl, Br and CF.sub.3 and where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-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.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.6-haloalkyl.

18. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is halogen, R.sup.3 is selected from the group consisting of halogen and C.sub.1-C.sub.2-haloalkyl and where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting C.sub.1-C.sub.4-alkyl C.sub.3-C.sub.7-cycloalkyl, and C.sub.1-C.sub.4-haloalkyl, and R.sup.2d is selected from the group consisting of C.sub.2-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.6-haloalkyl.

19. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is Cl and R.sup.3 is selected from the group consisting of Br and CF.sub.3. and where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-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.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.6-haloalkyl.

20. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.1 is Cl and R.sup.3 is Cl and where Z.sup.2 in R.sup.2 is a covalent bond, R.sup.2c is selected from the group consisting C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl and C.sub.1-C.sub.4-haloalkyl, and R.sup.2d is selected from the group consisting of C.sub.2-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.6-haloalkyl.

21. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R.sup.6 is 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.

22. The compound as claimed in claim 21, or an agriculturally suitable salt thereof, where R.sup.6 is methyl.

23. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, which is selected from the compounds of the following formulae I.A.I and I.D.I, ##STR00134## where, R.sup.1, R.sup.2c, R.sup.2d and R.sup.3 are as defined in the following tables: TABLE-US-00011 Formula R.sup.1 R.sup.2c R.sup.2d R.sup.3 1. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl 2. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl 3. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Cl 4. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl 5. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Cl 6. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl 7. I.A.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Cl 8. I.A.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl 9. I.A.I Cl CH.sub.3 CH.sub.2CH.sub.3 Cl 10. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl 11. I.A.I Cl CH.sub.3 CH.sub.2CF.sub.3 Cl 12. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl 13. I.A.I Cl CH.sub.3 CH.sub.2CHF.sub.2 Cl 14. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl 15. I.A.I Cl CH.sub.3 CH(CH.sub.3).sub.2 Cl 16. I.A.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl 17. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Br 18. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 19. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Br 20. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br 21. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Br 22. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br 23. I.A.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Br 24. I.A.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br 25. I.A.I Cl CH.sub.3 CH.sub.2CH.sub.3 Br 26. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 27. I.A.I Cl CH.sub.3 CH.sub.2CF.sub.3 Br 28. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br 29. I.A.I Cl CH.sub.3 CH.sub.2CHF.sub.2 Br 30. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br 31. I.A.I Cl CH.sub.3 CH(CH.sub.3).sub.2 Br 32. I.A.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br 33. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 34. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 35. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 36. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 37. I.A.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 38. I.A.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 39. I.A.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 40. I.A.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 41. I.A.I Cl CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 42. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 43. I.A.I Cl CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 44. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 45. I.A.I Cl CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 46. I.A.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 47. I.A.I Cl CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 48. I.A.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 49. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl 50. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl 51. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Cl 52. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl 53. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Cl 54. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl 55. I.D.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Cl 56. I.D.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl 57. I.D.I Cl CH.sub.3 CH.sub.2CH.sub.3 Cl 58. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl 59. I.D.I Cl CH.sub.3 CH.sub.2CF.sub.3 Cl 60. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl 61. I.D.I Cl CH.sub.3 CH.sub.2CHF.sub.2 Cl 62. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl 63. I.D.I Cl CH.sub.3 CH(CH.sub.3).sub.2 Cl 64. I.D.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl 65. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Br 66. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 67. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Br 68. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br 69. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Br 70. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br 71. I.D.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Br 72. I.D.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br 73. I.D.I Cl CH.sub.3 CH.sub.2CH.sub.3 Br 74. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br 75. I.D.I Cl CH.sub.3 CH.sub.2CF.sub.3 Br 76. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br 77. I.D.I Cl CH.sub.3 CH.sub.2CHF.sub.2 Br 78. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br 79. I.D.I Cl CH.sub.3 CH(CH.sub.3).sub.2 Br 80. I.D.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br 81. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 82. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 83. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 84. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 85. I.D.I CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 86. I.D.I CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 87. I.D.I CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 88. I.D.I CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 89. I.D.I Cl CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 90. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 91. I.D.I Cl CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 92. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 93. I.D.I Cl CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 94. I.D.I Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 95. I.D.I Cl CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 96. I.D.I Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 where c-C.sub.3H.sub.5 is cyclopropyl TABLE-US-00012 Formula R.sup.1 NR.sup.2cR.sup.2d R.sup.3 97. I.A.I CH.sub.3 pyrrolidin-1-yl Cl 98. I.A.I CH.sub.3 piperidin-1-yl Cl 99. I.A.I CH.sub.3 morpholin-4-yl Cl 100. I.A.I CH.sub.3 2,6-dimethylmorpholin-4- Cl yl 101. I.A.I Cl pyrrolidin-1-yl Cl 102. I.A.I Cl piperidin-1-yl Cl 103. I.A.I Cl morpholin-4-yl Cl 104. I.A.I Cl 2,6-dimethylmorpholin-4- Cl yl 105. I.A.I CH.sub.3 pyrrolidin-1-yl Br 106. I.A.I CH.sub.3 piperidin-1-yl Br 107. I.A.I CH.sub.3 morpholin-4-yl Br 108. I.A.I CH.sub.3 2,6-dimethylmorpholin-4- Br yl 109. I.A.I Cl pyrrolidin-1-yl Br 110. I.A.I Cl piperidin-1-yl Br 111. I.A.I Cl morpholin-4-yl Br 112. I.A.I Cl 2,6-dimethylmorpholin-4- Br yl 113. I.A.I CH.sub.3 pyrrolidin-1-yl CF.sub.3 114. I.A.I CH.sub.3 piperidin-1-yl CF.sub.3 115. I.A.I CH.sub.3 morpholin-4-yl CF.sub.3 116. I.A.I CH.sub.3 2,6-dimethylmorpholin-4- CF.sub.3 yl 117. I.A.I Cl pyrrolidin-1-yl CF.sub.3 118. I.A.I Cl piperidin-1-yl CF.sub.3 119. I.A.I Cl morpholin-4-yl CF.sub.3 120. I.A.I Cl 2,6-dimethylmorpholin-4- CF.sub.3 yl 121. I.D.I CH.sub.3 pyrrolidin-1-yl Cl 122. I.D.I CH.sub.3 piperidin-1-yl Cl 123. I.D.I CH.sub.3 morpholin-4-yl Cl 124. I.D.I CH.sub.3 2,6-dimethylmorpholin-4- Cl yl 125. I.D.I Cl pyrrolidin-1-yl Cl 126. I.D.I Cl piperidin-1-yl Cl 127. I.D.I Cl morpholin-4-yl Cl 128. I.D.I Cl 2,6-dimethylmorpholin-4- Cl yl 129. I.D.I CH.sub.3 pyrrolidin-1-yl Br 130. I.D.I CH.sub.3 piperidin-1-yl Br 131. I.D.I CH.sub.3 morpholin-4-yl Br 132. I.D.I CH.sub.3 2,6-dimethylmorpholin-4- Br yl 133. I.D.I Cl pyrrolidin-1-yl Br 134. I.D.I Cl piperidin-1-yl Br 135. I.D.I Cl morpholin-4-yl Br 136. I.D.I Cl 2,6-dimethylmorpholin-4- Br yl 137. I.D.I CH.sub.3 pyrrolidin-1-yl CF.sub.3 138. I.D.I CH.sub.3 piperidin-1-yl CF.sub.3 139. I.D.I CH.sub.3 morpholin-4-yl CF.sub.3 140. I.D.I CH.sub.3 2,6-dimethylmorpholin-4- CF.sub.3 yl 141. I.D.I Cl pyrrolidin-1-yl CF.sub.3 142. I.D.I Cl piperidin-1-yl CF.sub.3 143. I.D.I Cl morpholin-4-yl CF.sub.3 144. I.D.I Cl 2,6-dimethylmorpholin-4- CF.sub.3 yl

24. A composition comprising the compound as claimed in claim 1, or an agriculturally suitable salt thereof, and at least one auxiliary for formulating crop protection compounds.

25. A method for controlling unwanted vegetation comprising applying the compound of claim 1, or an agriculturally suitable salt thereof, or of the composition to plants, their seed and/or their habitat.

26. A method for controlling unwanted vegetation comprising allowing a herbicidally effective amount of the compound as claimed in claim 1, or an agriculturally suitable salt thereof, or of the composition thereof to act on plants, their seed and/or their habitat.

Description

EXAMPLE 1: PREPARATION OF: 4-CHLORO-3-[[ETHYL(METHYL)CARBAMOYL]AMINO]-2-METHYL-N-(1-METHYLTETRAZOL-5-yl)benzamide (entry 3 in Table 26)

Step 1: Methyl 4-chloro-3-isocyanato-2-methyl-benzoate

[0829] ##STR00105##

[0830] Triphosgene (bis(trichloromethyl) carbonate, 44.6 g, 0.15 mol) was dissolved in toluene (550 ml) and treated with a solution of methyl 3-amino-4-chloro-2-methyl-benzoate (15 g, 75 mmol) in 50 ml of toluene at a temperature of 70 C. Temperature was increased stepwise to reflux. Reflux was kept for 6 h and the reaction mixture stirred overnight at room temperature. Afterwards the reaction mixture was evaporated in vacuoto leave the product (16.8 g, 99%) as an orange solid which was used without further purification for the next step.

[0831] .sup.1H NMR (400 MHz, CDCl.sub.3), 7.65 (d, 1H) 7.3 (d, 1H), 3.9 (s, 3H), 2.6 (s, 3H).

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

[0832] ##STR00106##

[0833] Methyl 4-chloro-3-isocyanato-2-methyl-benzoate (2.50 g, 11.1 mmol) was dissolved in THF (60 ml) and diethylamine (720 mg, 12.2 mmol) was added dropwise at room temperature. Stirring was continued for 2.5 h. Water (10 ml) and lithium hydroxide (796 mg, ca. 33 mmol) was added and the mixture stirred overnight. The reaction mixture was concentrated in vacuo and the remaining aqueous phase was adjusted to a pH value of ca. 1-2 by addition of hydrochloric acid (1 molar). The product precipitated upon this treatment was filtered off. Drying in vacuo yielded 2.20 g of a solid (73%) of the title compound which was used without further purification in the next step.

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

[0834] ##STR00107##

[0835] 1-Methyltetrazol-5-amine (1.37 g, 13.9 mmol) was dissolved in anhydrous THF (100 ml) and cooled to 70 C. under argon atmosphere. A solution of methyl lithium in THF (3.1 molar, 13.9 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-chloro-3-[[ethyl(methyl)carbamoyl]amino]-2-methyl-benzoic acid (1.50 g, 5.54 mmol) was suspended in dichloromethane (DCM, 60 ml) and cooled to 78 C. under argon atmosphere and DAST (diethlyamino sulfur trifluoride, 982 mg, 6.10 mmol) was added via syringe. Cooling was continued for 3 h and the reaction mixture afterwards allowed to warm up to RT overnight. The solvent was evaporated in vacuo and re-dissolved in anhydrous THF (20 ml).

[0836] After addition if this solution stirring was continued at RT for 17 h and the reaction mixture carefully quenched by addition of water (40 ml). The major amounts of THF were evaporated in vacuo and the remainder adjusted to a pH value of 1-2 by addition of aqueous hydrochloric acid (2 molar). Extraction with ethyl acetate (330 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 (390 mg, 20%).

[0837] .sup.1H NMR (400 MHz, d6-DMSO), 13 (brs, 1H) 7.95 (s, 1H), 7.6 (d, 1H), 7.4 (d, 1H), 3.3 (m, 2H, hidden by solvent), 2.9 (s, 3H), 2.35 (s, 3H), 1.1 (t, 3H).

[0838] By analogy to the methods described in the Examples above, the following compounds of formulae I.A, I.B and I.D according to Table 26 were prepared:

TABLE-US-00009 TABLE 26 I.A [00108] I.B [00109] I.D [00110] in tables MS cpd. no formula 1 to 25 R.sup.1 R.sup.2 R.sup.3 R.sup.6 (m/z) 1 I.A I.A.I.547 CH.sub.3 [00111] Cl CH.sub.3 380.0 2 I.A I.A.I.313 CH.sub.3 [00112] Cl CH.sub.3 366.1 3 I.A I.A.I.283 CH.sub.3 [00113] Cl CH.sub.3 352.1 4 I.A I.A.I.289 CH.sub.3 [00114] Cl CH.sub.3 366.0 5 I.A I.A.I.367 CH.sub.3 [00115] Cl CH.sub.3 390.0 6 I.A I.A.I.571 CH.sub.3 [00116] Cl CH.sub.3 408.0 7 I.A I.A.I.577 CH.sub.3 [00117] Cl CH.sub.3 378.0 8 I.A I.A.I.583 CH.sub.3 [00118] Cl CH.sub.3 364.0 9 I.A I.A.I.307 CH.sub.3 [00119] Cl CH.sub.3 405.9 10 I.A 1.A.I.31 Cl [00120] Cl CH.sub.3 425.8 11 I.A I.A.VII.31 Cl [00121] Cl CH.sub.2CH.sub.2OCH.sub.3 469.9 12 I.A I.A.I.337 CH.sub.3 [00122] Cl CH.sub.3 419.9 13 I.A I.A.I.61 Cl [00123] Cl CH.sub.3 439.9 14 I.A I.A.I.55 Cl [00124] Cl CH.sub.3 421.9 15 I.A I.A.I.25 Cl [00125] Cl CH.sub.3 407.8 16 I.A I.A.I.301 CH.sub.3 [00126] Cl CH.sub.3 378.0 17 I.B I.B.I.31 Cl [00127] Cl CH.sub.3 424.8 18 I.D I.D.I.313 CH.sub.3 [00128] Cl CH.sub.3 365.9 19 I.D I.D.I.283 CH.sub.3 [00129] Cl CH.sub.3 351.8 20 I.D I.D.I.307 CH.sub.3 [00130] Cl CH.sub.3 405.9 21 I.D I.D.I.337 CH.sub.3 [00131] Cl CH.sub.3 419.9

Use Examples

[0839] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0840] 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.

[0841] 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.

[0842] This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.

[0843] 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.

[0844] Depending on the species, the plants were kept at 10-25 C. or 20-25 C., respectively.

[0845] 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.

[0846] 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.

[0847] At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against:

TABLE-US-00010 in tables cpd. no 1 to 25 ALOMY ECHCG AMARE CHEAL 1 I.A.I.547 98 100 100 100 2 I.A.I.313 98 100 100 100 3 I.A.I.283 98 100 100 100 4 I.A.I.289 98 100 100 100 5 I.A.I.367 98 100 100 100 9 I.A.I.307 >80 >80 >80 >80 10 I.A.I.31 >80 >80 >80 >80 11 I.A.VII.31 >80 >80 >80 >80 12 I.A.I.337 >80 >80 >80 >80 13 I.A.I.61 >80 >80 >80 >80 14 I.A.1.55 >80 >80 >80 >80 17 I.B.I.31 >80 >80 >80 >80 18 I.D.I.313 >80 >80 >80 >80 20 I.D.I.307 >80 >80 >80 >80 21 I.D.I.337 >80 >80 >80 >80 ALOMY (Alopecurus myosuroiedes) ECHCG (Echinocloa crus-galli) AMARE (Amaranthus retroflexus) CHEAL (Chenopodium album)