Patent EA-001605-B1 (EA)
Title: Sustituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal effect
Inventor: HILL REGINA LUISE
IPC: A01N33/24
Filed: 1997-12-19
Abstract: 1. 2-benzoylcyclohexane-1,3-diones of the formula I and agriculturally useful salts thereof:   wherein R<1> and R<2> are each hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR<5>, -OCOR<6>, -OSO2R<6>, -SH, -S(O)nR<7>, -SO2OR<5>, -SO2NR<5>R<8>, -NR<8>SO2R<6> or -NR<8>COR<6>; R<3> is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, -OR<7>, -SR<7> or -NR<7>R<10>; R<4> is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, -COR<9>, -CO2R<9>, -COSR<9> or -CONR<8>R<9>, where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned and R<9> of the radicals -COR<9>, -CO2R<9>, -COSR<9> and -CONR<8>R<9> may be partially or fully halogenated and/or carry one to three of the following groups: hydroxy, mercapto, amino, cyano, R<10>, -OR<10>, -SR<10>, -NR<8>R<10>, =NOR<10>, -OCOR<10>, -SCOR<10>, -NR<8>COR<10>, -CO2R<10>, -COSR<10>, -CONR<8>R<10>, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; X is oxygen or NR<8>; n is 0, 1 or 2; R<5> is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R<6> is C1-C6-alkyl or C1-C6-haloalkyl; R<7> is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R<8> is hydrogen or C1-C6-alkyl; R<9> is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl; R<10> is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl; Q is a cyclohexane-1,3-dione ring attached in position 2 with or without substitution. 2. 2-benzoylcyclohexane-1,3-diones of the formula I as claimed in Claim 1 in which Q is a cyclohexane-1,3-dione ring of the formula II attached in position 2   wherein R<11>, R<12>, R<14> and R<16> are each hydrogen or C1-C4-alkyl; R<13> is hydrogen, C1-C4-alkyl or C3-C4-cycloalkyl, where the last two groups may carry one to three of the following substituents: halogen, C1-C4-alkylthio or C1-C4-alkoxy; or is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the last 6 radicals mentioned may be substituted by one to three C1-C4-alkyl radicals; R<15> is hydrogen, C1-C4-alkyl or C1-C6-alkoxycarbonyl; or R<13> and R<16> together form a π-bond or a three- to six-membered carbocyclic ring; or CR<13>R<14> unit can be replaced by C=O. 3. 2-benzoylcyclohexane-1,3-diones of the formula I as claimed in Claim 1 or 2, wherein R<1> is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR<5> or -S(O)nR<7>; R<2> is hydrogen or one of the radicals mentioned above for R<1>. 4. 2-benzoylcyclohexane-1,3-diones of the formula Ia   wherein the substituents R<1> to R<4>, X and Q are each as defined under Claims 1 to 3. 5. A process for preparing 2-benzoylcyclohexane-1,3-diones of the formula I as claimed in any of Claims 1 to 4, which comprises acylating an unsubstituted or substituted cyclohexane-1,3-dione Q with an activated carboxylic acid IIIα or with a carboxylic acid IIIβ,   where the substituents R<1> to R<4> and X are each as defined under Claim 1 and L is a nucleophilically displaceable leaving group, and rearranging the acylation product in the presence or absence of a catalyst to the compounds I. 6. Benzoic acid derivatives of the formula IIIa,   wherein R<1> is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or -S(O)nR<7>; R<2> is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR<5> or -S(O)nR<7>; R<4> is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, -COR<9>, -CO2R<9>, -COSR<9> or -CONR<8>R<9>, where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned and R<9> of the radicals -COR<9>, -CO2R<9>, -COSR<9> and -CONR<8>R<9> may be partially or fully halogenated and/or carry one to three of the following groups: hydroxy, mercapto, amino, cyano, R<10>, -OR<10>, -SR<10>, -NR<8>R<10>, =NOR<10>, -OCOR<10>, -SCOR<10>, -NR<8>COR<10>, -CO2R<10>, -COSR<10>, -CONR<8>R<10>, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; R<17> is hydroxy or a radical that can be removed by hydrolysis and the substituents R<3>, R<5> and R<7>-R<10>, X and n are each as defined under Claim 1. 7. Benzoic acid derivatives of the formula IIIa as claimed in Claim 6, wherein R<17> is halogen, hydroxy or C1-C6-alkoxy. 8. A composition comprising a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of compound I as claimed in any of Claims 1-4, and auxiliaries usually used in the formulation of crop protection agents. 9. A process for preparing herbicidally effective compositions as claimed in Claim 8, which comprises mixing a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of compound I as claimed in any of Claims 1 to 4 and auxiliaries usually used in the formulation of crop protection agents. 10. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of compound I as claimed in any of Claims 1-4 to act on plants, their habitat and/or on seeds. 11. Use of the compounds of the formula I and of agriculturally useful salts thereof as claimed in any of Claims 1-4 as herbicides.