BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES II

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.2n—Z.sup.2, R.sup.5 is hydrogen, R.sup.1, R.sup.3, R.sup.4 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, ##STR00142## wherein Q is Q.sup.1 or Q.sup.2 or Q.sup.3 or Q.sup.4, ##STR00143## 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.1b—S(O).sub.k—Z.sup.1; R.sup.2 is R.sup.2cR.sup.2dNC(O)NR.sup.2n—Z.sup.2; R.sup.3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy-Z.sup.2, 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.8-haloalkynyloxy-Z.sup.2, R.sup.2b—S(O).sub.k—Z.sup.2, R.sup.2c—C(O)—Z.sup.2, R.sup.2dO—C(O)—Z.sup.2, R.sup.2dO—N═CH—Z.sup.2, R.sup.2eR.sup.2fN—C(O)—Z.sup.2, R.sup.2b—S(O).sub.k—Z.sup.2, R.sup.2c—C(O)O—Z.sup.2, R.sup.2dO—C(O)O—Z.sup.2, R.sup.2dO—N═CH—Z.sup.2, R.sup.2eR.sup.2fN—C(O)—Z.sup.2, R.sup.2gR.sup.2hN—Z.sup.2, R.sup.22C(O)O—Z.sup.2, R.sup.25OC(O)O—Z.sup.2, (R.sup.22).sub.2NC(O)O—Z.sup.2, R.sup.25S(O).sub.2O—Z.sup.2, R.sup.22OS(O).sub.2—Z.sup.2, (R.sup.22).sub.2NS(O).sub.2—Z.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 selected from the group consisting of 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 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.b—S(O).sub.n—C.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, O—C.sub.1-C.sub.4-alkanediyl, C.sub.1-C.sub.4-alkanediyl-0 and C.sub.1-C.sub.4-alkanediyl-O—C.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.n—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, C.sub.1-C4-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.n—C.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-O—C.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)—C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.n—C.sub.1-C.sub.6-alkyl, heterocyclyl-Z.sup.1, heterocyclyl-N(R.sup.23)—C.sub.1-C.sub.6-alkyl, heterocyclyl-O—C.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.n—C.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.23O—C.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-O—C.sub.1-C.sub.6-alkyl, phenyl-N(R.sup.23)—C.sub.1-C.sub.6-alkyl, phenyl-S(O).sub.n—C.sub.1-C.sub.6-alkyl, heterocyclyl-Z.sup.1, heterocyclyl-N(R.sup.23)—C.sub.1-C.sub.6-alkyl, heterocyclyl-O—C.sub.1-C.sub.6-alkyl, heterocyclyl-S(O).sub.n—C.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.23O—C.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.

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.1b—S(O).sub.k—Z.sup.1.

7. The compound as claimed in claim 6, 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.

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.2n—Z.sup.2, where 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 8, 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.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.

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 hydrogen, halogen, 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 hydrogen, 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.4 is selected from the group consisting cyano, halogen, nitro, C.sub.1-C.sub.2-alkyl, and C.sub.1-C.sub.2-haloalkyl.

15. The compound as claimed in claim 14, or an agriculturally suitable salt thereof, where R.sup.4 is selected from the group consisting of fluorine and chlorine.

16. 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.

17. 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, ##STR00144## where R.sup.1 is selected from the group consisting of halogen and C.sub.1-C.sub.4-alkyl, 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, 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, R.sup.3 is selected from the group consisting of hydrogen, halogen and C.sub.1-C.sub.2-haloalkyl, and R.sup.4 is selected from the group consisting of fluorine and chlorine.

18. The compound as claimed in claim 17, or an agriculturally suitable salt thereof, where, R.sup.1, R.sup.2c, R.sup.2d, R.sup.3 and R.sup.4 are as defined in the following tables: TABLE-US-00010 R.sup.1 R.sup.2c R.sup.2d R.sup.3 R.sup.4 1. CH.sub.3 CH.sub.3 CH.sub.3 H Cl 2. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H Cl 3. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H Cl 4. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 H Cl 5. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 H Cl 6. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 H Cl 7. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 H Cl 8. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 H Cl 9. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 H Cl 10. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 H Cl 11. Cl CH.sub.3 CH.sub.3 H Cl 12. Cl CH.sub.3 CH.sub.2CH.sub.3 H Cl 13. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 H Cl 14. Cl CH.sub.3 CH.sub.2CF.sub.3 H Cl 15. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 H Cl 16. Cl CH.sub.3 CH.sub.2CHF.sub.2 H Cl 17. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 H Cl 18. Cl CH.sub.3 CH(CH.sub.3).sub.2 H Cl 19. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 H Cl 20. CH.sub.3 CH.sub.3 CH.sub.3 Cl Cl 21. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl Cl 22. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl Cl 23. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl Cl 24. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Cl Cl 25. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl Cl 26. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Cl Cl 27. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl Cl 28. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Cl Cl 29. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl Cl 30. Cl CH.sub.3 CH.sub.3 Cl Cl 31. Cl CH.sub.3 CH.sub.2CH.sub.3 Cl Cl 32. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl Cl 33. Cl CH.sub.3 CH.sub.2CF.sub.3 Cl Cl 34. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl Cl 35. Cl CH.sub.3 CH.sub.2CHF.sub.2 Cl Cl 36. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl Cl 37. Cl CH.sub.3 CH(CH.sub.3).sub.2 Cl Cl 38. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl Cl 39. CH.sub.3 CH.sub.3 CH.sub.3 Br Cl 40. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Br Cl 41. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br Cl 42. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Br Cl 43. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br Cl 44. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Br Cl 45. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br Cl 46. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Br Cl 47. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br Cl 48. Cl CH.sub.3 CH.sub.3 Br Cl 49. Cl CH.sub.3 CH.sub.2CH.sub.3 Br Cl 50. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br Cl 51. Cl CH.sub.3 CH.sub.2CF.sub.3 Br Cl 52. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br Cl 53. Cl CH.sub.3 CH.sub.2CHF.sub.2 Br Cl 54. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br Cl 55. Cl CH.sub.3 CH(CH.sub.3).sub.2 Br Cl 56. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br Cl 57. CH.sub.3 CH.sub.3 CH.sub.3 CF.sub.3 Cl 58. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 Cl 59. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 Cl 60. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 Cl 61. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 Cl 62. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 Cl 63. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 Cl 64. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 Cl 65. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 Cl 66. Cl CH.sub.3 CH.sub.3 CF.sub.3 Cl 67. Cl CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 Cl 68. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 Cl 69. Cl CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 Cl 70. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 Cl 71. Cl CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 Cl 72. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 Cl 73. Cl CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 Cl 74. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 Cl 75. CH.sub.3 CH.sub.3 CH.sub.3 H F 76. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H F 77. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 H F 78. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 H F 79. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 H F 80. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 H F 81. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 H F 82. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 H F 83. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 H F 84. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 H F 85. Cl CH.sub.3 CH.sub.3 H F 86. Cl CH.sub.3 CH.sub.2CH.sub.3 H F 87. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 H F 88. Cl CH.sub.3 CH.sub.2CF.sub.3 H F 89. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 H F 90. Cl CH.sub.3 CH.sub.2CHF.sub.2 H F 91. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 H F 92. Cl CH.sub.3 CH(CH.sub.3).sub.2 H F 93. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 H F 94. CH.sub.3 CH.sub.3 CH.sub.3 Cl F 95. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl F 96. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Cl F 97. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl F 98. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Cl F 99. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl F 100. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Cl F 101. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl F 102. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Cl F 103. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl F 104. Cl CH.sub.3 CH.sub.3 Cl F 105. Cl CH.sub.3 CH.sub.2CH.sub.3 Cl F 106. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Cl F 107. Cl CH.sub.3 CH.sub.2CF.sub.3 Cl F 108. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Cl F 109. Cl CH.sub.3 CH.sub.2CHF.sub.2 Cl F 110. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Cl F 111. Cl CH.sub.3 CH(CH.sub.3).sub.2 Cl F 112. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Cl F 113. CH.sub.3 CH.sub.3 CH.sub.3 Br F 114. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 Br F 115. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br F 116. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 Br F 117. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br F 118. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 Br F 119. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br F 120. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 Br F 121. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br F 122. Cl CH.sub.3 CH.sub.3 Br F 123. Cl CH.sub.3 CH.sub.2CH.sub.3 Br F 124. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 Br F 125. Cl CH.sub.3 CH.sub.2CF.sub.3 Br F 126. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 Br F 127. Cl CH.sub.3 CH.sub.2CHF.sub.2 Br F 128. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 Br F 129. Cl CH.sub.3 CH(CH.sub.3).sub.2 Br F 130. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 Br F 131. CH.sub.3 CH.sub.3 CH.sub.3 CF.sub.3 F 132. CH.sub.3 CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 F 133. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 F 134. CH.sub.3 CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 F 135. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 F 136. CH.sub.3 CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 F 137. CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 F 138. CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 F 139. CH.sub.3 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 F 140. Cl CH.sub.3 CH.sub.3 CF.sub.3 F 141. Cl CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 F 142. Cl CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 CF.sub.3 F 143. Cl CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 F 144. Cl CH.sub.2CH.sub.3 CH.sub.2CF.sub.3 CF.sub.3 F 145. Cl CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 F 146. Cl CH.sub.2CH.sub.3 CH.sub.2CHF.sub.2 CF.sub.3 F 147. Cl CH.sub.3 CH(CH.sub.3).sub.2 CF.sub.3 F 148. Cl c-C.sub.3H.sub.5 c-C.sub.3H.sub.5 CF.sub.3 F where c-C.sub.3H.sub.5 is cyclopropyl TABLE-US-00011 R.sup.1 NR.sup.2cR.sup.2d R.sup.3 R.sup.3 149. CH.sub.3 pyrrolidin-1-yl H Cl 150. CH.sub.3 piperidin-1-yl H Cl 151. CH.sub.3 morpholin-4-yl H Cl 152. CH.sub.3 2,6-dimethylmorpholin-4-yl H Cl 153. Cl pyrrolidin-1-yl H Cl 154. Cl piperidin-1-yl H Cl 155. Cl morpholin-4-yl H Cl 156. Cl 2,6-dimethylmorpholin-4-yl H Cl 157. CH.sub.3 pyrrolidin-1-yl Cl Cl 158. CH.sub.3 piperidin-1-yl Cl Cl 159. CH.sub.3 morpholin-4-yl Cl Cl 160. CH.sub.3 2,6-dimethylmorpholin-4-yl Cl Cl 161. Cl pyrrolidin-1-yl Cl Cl 162. Cl piperidin-1-yl Cl Cl 163. Cl morpholin-4-yl Cl Cl 164. Cl 2,6-dimethylmorpholin-4-yl Cl Cl 165. CH.sub.3 pyrrolidin-1-yl Br Cl 166. CH.sub.3 piperidin-1-yl Br Cl 167. CH.sub.3 morpholin-4-yl Br Cl 168. CH.sub.3 2,6-dimethylmorpholin-4-yl Br Cl 169. Cl pyrrolidin-1-yl Br Cl 170. Cl piperidin-1-yl Br Cl 171. Cl morpholin-4-yl Br Cl 172. Cl 2,6-dimethylmorpholin-4-yl Br Cl 173. CH.sub.3 pyrrolidin-1-yl CF.sub.3 Cl 174. CH.sub.3 piperidin-1-yl CF.sub.3 Cl 175. CH.sub.3 morpholin-4-yl CF.sub.3 Cl 176. CH.sub.3 2,6-dimethylmorpholin-4-yl CF.sub.3 Cl 177. Cl pyrrolidin-1-yl CF.sub.3 Cl 178. Cl piperidin-1-yl CF.sub.3 Cl 179. Cl morpholin-4-yl CF.sub.3 Cl 180. Cl 2,6-dimethylmorpholin-4-yl CF.sub.3 Cl 181. CH.sub.3 pyrrolidin-1-yl H F 182. CH.sub.3 piperidin-1-yl H F 183. CH.sub.3 morpholin-4-yl H F 184. CH.sub.3 2,6-dimethylmorpholin-4-yl H F 185. Cl pyrrolidin-1-yl H F 186. Cl piperidin-1-yl H F 187. Cl morpholin-4-yl H F 188. Cl 2,6-dimethylmorpholin-4-yl H F 189. CH.sub.3 pyrrolidin-1-yl Cl F 190. CH.sub.3 piperidin-1-yl Cl F 191. CH.sub.3 morpholin-4-yl Cl F 192. CH.sub.3 2,6-dimethylmorpholin-4-yl Cl F 193. Cl pyrrolidin-1-yl Cl F 194. Cl piperidin-1-yl Cl F 195. Cl morpholin-4-yl Cl F 196. Cl 2,6-dimethylmorpholin-4-yl Cl F 197. CH.sub.3 pyrrolidin-1-yl Br F 198. CH.sub.3 piperidin-1-yl Br F 199. CH.sub.3 morpholin-4-yl Br F 200. CH.sub.3 2,6-dimethylmorpholin-4-yl Br F 201. Cl pyrrolidin-1-yl Br F 202. Cl piperidin-1-yl Br F 203. Cl morpholin-4-yl Br F 204. Cl 2,6-dimethylmorpholin-4-yl Br F 205. CH.sub.3 pyrrolidin-1-yl CF.sub.3 F 206. CH.sub.3 piperidin-1-yl CF.sub.3 F 207. CH.sub.3 morpholin-4-yl CF.sub.3 F 208. CH.sub.3 2,6-dimethylmorpholin-4-yl CF.sub.3 F 209. Cl pyrrolidin-1-yl CF.sub.3 F 210. Cl piperidin-1-yl CF.sub.3 F 211. Cl morpholin-4-yl CF.sub.3 F 212. Cl 2,6-dimethylmorpholin-4-yl CF.sub.3 F.

19. 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.

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

21. 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

[0679] The following examples will further illustrate the invention:

[0680] 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 tables that follow, 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.

HPLC-MS=high performance liquid chromatography coupled with mass spectrometry;

[0681] HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; 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 40° C., flow rate 1.8 mL/min.

[0682] MS: quadrupole electrospray ionization, 80 V (positive mode).

[0683] HPLC column: Luna-C18(2) 5 μm column (Phenomenex), 2.0*50 mm; mobile phase: acetonitrile+0.0625% trifluoroacetic acid (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).

[0684] DCM: dichloromethane

[0685] DIPEA: diisopropylethylamine

[0686] DIC (N,N′-diisopropyl carbodiimide

[0687] DMAP: Dimethylaminopyridine

[0688] DMF: N,N-dimethylformamide

[0689] MS: Mass spectrometry

[0690] EtOAc: acetic acid ethyl ester

[0691] THF: tetrahydrofuran

[0692] TFA: trifluoroacetic acid

EXAMPLE 1

Preparation of: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-N-(1-methyltetrazol-5-yl)benzamide

Step 1: Methyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoate

[0693] ##STR00137##

[0694] To a solution of triphosgene (640 mg, 2.19 mmol) in DCM (8 mL) a solution of commercially available methyl 3-amino-2,5-dichloro-benzoate (800 mg, 3.65 mol) in DCM (8 mL) was added. Then DIPEA (diisopropylethylamine, 844 mg, 6.57 mmol) was added to the mixture at 0° C. under N2 atmosphere. The mixture was stirred at 0° C. for 3 h. N-cyclopropylcyclopropanamine hydrochloride (960 mg, 7.3 mmol) and triethylamine (1.45 g, 14.6 mmol) was added and the mixture was stirred for further 3 h at 15° C. To the reaction mixture 20 mL H.sub.2O was added. The layers were separated and andn the aqueous layer was washed with DCM. The combined organic layers were washed with brine and dried over Na.sub.2SO.sub.4. After concentration in vacuo the compound was purified by column chromatography to give the title compound (1.642 g, crude) as a light yellow solid.

[0695] .sup.1H NMR (400 MHz, CDCl.sub.3), δ 8.74 (d, 1H), 8.22 (s, 1H), 7.43 (d, 1H), 3.96-3.91 (m, 3H), 2.63-2.55 (m, 2H), 1.01-0.95 (m, 4H), 0.92-0.87 (m, 4H)

Step 2: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoic acid

[0696] ##STR00138##

[0697] To a solution of methyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoate (1 g, crude) in THF/H.sub.2O (10 mL/2.5 mL) LiOH (420 mg, 17.5 mmol) was added at 0° C. under N2 atmosphere. It was stirred at 15° C. for 2 days. The reaction mixture was adjusted to pH 3 with aqueous 1 N HCl solution and the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na.sub.2SO.sub.4 and concentrated in vacuo to give 2,5-dichloro-3-(dicyclopropylcarbamoylamino)benzoic acid as a crude solid which was used without further purification for the next step.

[0698] .sup.1H NMR (400 MHz, CDCl.sub.3), δ 8.50-8.36 (m, 1H), 8.25 (s, 1H), 7.41 (br d, 1H), 2.71-2.57 (m, 2H), 0.87 (br d, J=5.5 Hz, 4H), 0.84-0.76 (m, 4H)

Step 3: pentafluorophenyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoate

[0699] ##STR00139##

[0700] To a solution of 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoic acid (1 g, 2.9 mmol), 2,3,4,5,6-pentafluorophenol (810 mg, 4.4 mmol) and DMAP (35 mg, 0.29 mmol) in DMF (10 mL) DIC (554 mg, 4.4 mmol) was added at 0° C. The mixture was stirred at 10° C. for 10 h. The reaction mixture was poured into 20 mL lithium chloride solution (water, 4%), extracted with EtOAc and the organic layers were washed with brine, dried over Na.sub.2SO.sub.4, concentrated in vacuo and purified by column chromatography to give the title compound (1.1 g, crude) as a white solid.

[0701] .sup.1H NMR (400 MHz, CDCl.sub.3), δ 8.89 (d, 1H), 8.29 (s, 1H), 7.72 (d, 1H), 2.62 (m.sub.e, 2H), 1.05-0.97 (m, 4H), 0.96-0.89 (m, 4H)

Step 4: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-N-(1-methyltetrazol-5-yl)benzamide

[0702] ##STR00140##

To a solution of 1-methyltetrazol-5-amine (481 mg, 4.86 mmol) in NMP (16 mL) NaH (60%, 162 mg, 4.05 mmol) was added at 0° C. and the mixture was stirred for 0.5 h. Then, 2,3,4,5,6-pentafluorophenyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoate (800 mg, 1.62 mmol) in NMP (4 mL) was added, and the mixture was stirred at 15° C. for another 8 h. The reaction mixture was poured into lithium chloride solution (4%, 30 mL). The the mixture was adjusted to pH 6-7 with 1 N HCl, extracted with EtOAc, the combined organic layers were washed with brine, dried over Na.sub.2SO.sub.4, concentrated in vacuo and purified by chromatography to give the title compound (220 mg) as a white solid.

[0703] .sup.1H NMR (400 MHz, d6-DMSO), δ 8.34 (d, 1H), 8.22 (s, 1H), 7.42 (d, 1H), 3.91 (s, 3H), 2.66-2.60 (m, 2H), 0.92-0.85 (m, 4H), 0.81 (q, 4H).

EXAMPLE 2

Preparation of: 2,5-dichloro-3-[(2,2,2-trifluoroethyl)(methyl)carbamoylamino]-N-(1-methyltetrazol-5-yl)benzamide

[0704] ##STR00141##

[0705] The title compound was prepared by analogy to the method described in Example 1.

[0706] HPLC-MS: m/z 425.8 (M+H).sup.+

USE EXAMPLES

[0707] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0708] 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.

[0709] 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.

[0710] 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. Depending on the species, the plants were kept at 10-25° C. or 20-25° C., respectively.

[0711] 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.

[0712] 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.

[0713] At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against:

ECHCG (Echinocloa crus-galli)
AMARE (Amaranthus retroflexus)
CHEAL (Chenopodium album)

TABLE-US-00009 Example ECHCG AMARE CHEAL 1 >80 >80 >80 2 >80 >80 >80