Patent EA-002599-B1 (EA)
Title: Substiteted 2-benzoyl-cyclohexane-1,3-diones
Inventor: ENGEL STEFAN
IPC: C07D305/08
Filed: 1998-04-24
Abstract: 1. The substituted 2-benzoylcyclohexane-1,3-diones of the formula I: wherein substituents have the following meanings: R<1> and R<2> are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6haloalkyl, C1-C6alkoxy, C2-C6alkenyl, C2-C6alkynyl, -OR<10>, -OCOR<10>, -OSO2R<10>, -S(O)nR<10>, -SO2OR<10>, -SO2NR<3>R<10>, -NR<10>SO2R<10> or -NR<10>COR; Q is a cyclohexane-1,3-dione ring with or without substitution, which is attached in position 2; A is a group of the formula IIa, IIb or III: wherein substituents have the following meanings: R<3> is hydrogen, C1-C6alkyl or phenyl, where the alkyl and phenyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, 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-C4alkoxyamino, C1-C4alkylcarbonyl, C1-C4alkoxy-C2-C6alkoxycarbonyl, C1-C4alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; R<4>-R<7> may be identical or different and, independently of each other, are: hydrogen, hydroxyl, mercapto, amino, halogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, -OR<10>, -S(O)nR<10>, -OS(O)nR<10>, -PO(OR<10>)2, -NR<3>R<10>, -Si(R<10>)3 or -OCOR<10>, where the alkyl and cycloalkyl radicals mentioned and R<3> and R<10> of the radicals -OR<10>, -S(O)nR<10>, -OS(O)nR<10>, -PO(OR<10>)2, -NR<3>R<10>, -Si(R<10>)3, -OCOR<10> may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, 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-C4alkyliminooxy, C1-C4alkoxyamino, C1-C4alkylcarbonyl, C1-C4alkoxy-C2-C6alkoxycarbonyl, C1-C4alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; R<4> and R<5> together may form a C2-C5alkylene or C2-C5alkenylene chain which may be interrupted once or twice by a nitrogen or an oxygen atom, or may form a group =X, where X is an oxygen atom or a group CR<3>R<10>, NR<10> or NOR<10>; R<6> and R<7> together may form a C2-C5alkylene or C2-C5alkenylene chain which may be interrupted once or twice by a nitrogen or an oxygen atom, or may form a group =X, where X is an oxygen atom or a group CR<3>R<10>, NR<10> or NOR<10>; n is zero, one or two; R<5> and R<6> together may furthermore, if they are attached to adjacent carbon atoms and if R<4> and R<7> are each hydrogen, form a C3-C4alkylene or C3-C4alkenylene chain which may be interrupted by a nitrogen or an oxygen atom; R<8> and R<9> may be identical or different and, independently of each other, are: hydrogen, nitro, halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C5-C6heterocyclyl, -OR<10>, -SR<10>, -COR<10>, -COOR<10>, -CONR<3>R<10>, phenyl, phenylC1-C6alkyl and five- or six-membered hetaryl, where the alkyl and cycloalkyl radicals mentioned and R<3> and R<10> of the radicals -OR<10>, -SR<10>, -COR<10>, -COOR<10>, -CONR<3>R<10> may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, 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-C4alkyliminooxy, C1-C4alkoxyamino, C1-C4alkylcarbonyl, C1-C4alkoxy-C2-C6alkoxycarbonyl, C1-C4alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; R<8> and R<9> together may furthermore form a C2-C5alkylene or C2-C5alkenylene chain which may be interrupted once or twice by a nitrogen or an oxygen atom; R<10> is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, phenyl or phenyl-C1-C6alkyl; where the alkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R<10>, -OR<10>, -SR<10>, -NR<3>R<10>, =NOR<10>, -OCOR<10>, -SCOR<10>, -NR<3>COR<10>, -CO2R<10>, -COSR<10>, -CONR<3>R<10>, C1-C4 alkyliminooxy, C1-C4alkoxyamino, C1-C4alkylcarbonyl, C1-C4alkoxy-C2-C6alkoxycarbonyl, C1-C4alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted; and agriculturally useful salts thereof. 2. The 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 IV: which is attached in position 2, where R<11>, R<12>, R<14> and R<16> are each hydrogen or C1-C4alkyl; R<13> is hydrogen, C1-C4alkyl or C3-C4cycloalkyl, where the last two groups mentioned may carry one to three of the following substituents: halogen, C1-C4alkylthio or C1-C4alkoxy; 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-C4alkyl radicals; R<15> is hydrogen, C1-C4alkyl or C1-C6alkoxycarbonyl; or R<13> and R<16> together form a π- bond or a three- to six-membered carbocyclic ring; or the CR<13>R<14> unit may be replaced by C=O. 3. The 2-Benzoylcyclohexane-1,3-dione of the formula I as claimed in Claim 1 or 2 wherein: R<1> is nitro, halogen, cyano, thiocyanato, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy-C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, -OR<5> or -S(O)nR<7>; R<2> is hydrogen or one of the radicals mentioned above under R<1>. 4. The 2-Benzoylcyclohexane-1,3-diones of the formula Ia as claimed in one of Claims 1 to 3,   wherein the substituents R<1>, R<2>, Q and A are each as defined in Claim 1 to 3. 5. The 2-Benzoylcyclohexane-1,3-diones of the formula Ia as claimed in Claim 4, in which A is a group of the formula IIa or IIb. 6. The 2-Benzoylcyclohexane-1,3-diones of the formula Ia as claimed in Claim 4, in which A is a group of the formula III. 7. A process for preparing the 2-benzoylcyclohexane-1,3-diones of the formula I as claimed in Claim 1 to 6, which comprises acylating a cyclohexane-1,3-dione Q with or without substitution with an activated carboxylic acid Va or with a carboxylic acid Vb: where the substituents R<1>, R<2> and A are each as defined under Claim 1 and L is a nucleophilically exchangeable leaving group, and rearranging the acylation product, if appropriate in the presence of a catalyst, to give the compounds I. 8. A composition, which comprises a herbicidally active amount of at least one compound of the formula I or an agriculturally useful salt of I as claimed in Claim 1 to 6 and auxiliaries which are customarily used for formulating crop protection agents. 9. A process for preparing herbicidally active 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 I as claimed in Claim 1 to 6 and auxiliaries which are customarily used for formulating 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 I as claimed in Claim 1 to 6 to act on plants, their habitat and/or on seeds. 11. A method of using the compounds of the formula I and agriculturally useful salts thereof as claimed in Claim 1 to 6 as herbicides.