N-cycloalkyl-3-alkenybenzoyl-pyrazole derivatives

A pyrazole of the formula I

• where:
• R1 is hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, —S(O)nR8, —SO2OR9, —SO2NR9R10, —NR10SO2R11, —NR10COR11, —PO(OR12)(OR13);
• R2 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C2-C6-alkenyl, C2-C6-alkynyl, halogen, nitro, —S(O)nR8, —SO2OR9, —SO2NR9R10, —NR10SO2R11, —NR10COR11, —PO(OR12)(OR13);
• R3 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl;
• R4, R5 are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkylthio, C1-C6-haloalkoxy, —COR12, —CO2R12, —COSR12, —CONR12R13, —C(R14)═NR15, —PO(OR12)(OR13), C1-C4-alkyl carrying a radical from the following group:
• —COR12, —CO2R12, —COSR12, —CONR12R13 or —C(R14)═NR15;
• heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl or hetaryl-C1-C4-alkyl, where the six last-mentioned radicals may be substituted by one to three halogen atoms and/or may carry one to three radicals from the following group:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl;
• or C1-C4-alkoxycarbonyl;
• and where heterocyclyl alone and in composed form is a three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycle which contains one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur;
• and where heteroaryl alone and in composed form is an aromatic or polycyclic radical which, in addition to carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom;
• or
• R4 and R5 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or may be interrupted by oxygen or sulfur or an unsubstituted or C1-C4-alkyl substituted nitrogen;
• R6 is hydrogen, halogen, C1-C6-alkyl, C1-C6-alkoxy, C3-C8-cycloalkyl;
• R7 is C3-C14-cycloalkyl, C3-C14-cycloalkenyl or a carbocyclic bi- or tricyclic system selected from the group consisting of adamantyl, camphyl, camphenyl and norbornyl;
• n is 0, 1 or 2;
• R8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R9 is hydrogen, C1-C6-alkyl, C1-C6-aloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R10 is hydrogen or C1-C6-alkyl;
• R11 is C1-C6-alkyl or C1-C6-haloalkyl;
• R12 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
• R13 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• or
• R12 and R13 together form a C2-C6-alkanediyl chain which may be mono- to tetrasubstituted by C1-C4-alkyl and/or may be interrupted by oxygen or sulfur or an unsubstituted or C1-C4-alkyl-substituted nitrogen;
• R14 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl or benzyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
• R15 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, phenyl, benzyl or benzyloxy, where the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
• R16 is hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenyl-C1-C4-alkoxy, phenylcarbonyloxy, phenylcarbonyl-C1-C4-alkoxy, phenylsulfonyloxy, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• and their tautomers and agriculturally useful salts.