Patent EA-001202-B1 (EA)
Title: 2-cyclohexane-1,3-dione bensoyl derivatives
Inventor: OTTEN MARTINA
IPC: C07D279/16
Filed: 1996-08-29
Abstract: 1. A benzoyl derivative of the formula I   where the substituents have the following meanings: L and M are hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4alkoxy group; halogen, cyano, nitro, a group -(A)m-S(O)nR<1> or a group -(A)m-CO-R<2>; Y is a group consisting of C=O, C=N-R<3>, CR<7>-NR<5>R<6>, CR<7>-OR<8>, CR<10>R<11>, CR<7>-SR<8>; substituted with hydrogen or C1-C4alkyl 1,3-dioxanyl or 1,3-dioxolanyl, a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen; X is a chain (-CR<12>R<13>-), (-CR<12>R<13>-CR<21>CR<22>-), (-CR<12>=CR<13>-), (-CR<12>R<13>-CR<12>=CR<13>-); NR<23>; the bond between X and Y can be saturated or unsaturated; A is O.NR<14>; m is zero or one; n is zero, one or two; R<1> is C1-C4alkyl, C1-C4haloalkyl or NR<14>; R<2> is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or NR<14>; R<3> is hydrogen, -NR<9>R<4>; C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl; optionally substituted phenyl, it being possible for the substituents to be selected from the group consisting of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C-4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyloxy, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<4> is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C=O-NR<14>; optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<9> is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C=O-NR<14>; optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<5> and R<6> independently of one another are hydrogen, C1-C6alkyl, C2-C6alkenyl, C1-C4haloalkyl, C2-C6haloalkenyl, C1-C6alkoxy, C1-C6haloalkoxy; optonally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<7> is hydrogen, C1-C6alkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy; optionally substituted phenyl, it being possible for the substituents to be selected from the group consisting of one to three halogens, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro; wherein R<7> and R<21> or R<7> and R<23> or R<7> and R<12> can form a bond; R<8> is hydrogen, C1-C6alkyl, C1-C4haloalkyl, optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<10> and R<11> independently of one another are hydrogen, C1-C6alkyl; optionally substituted phenyl, it being possible for the substituents to consist of one to three halogens, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro; wherein R<10> and R<12> or R<10> and R<21> or R<10> and R<23> can form a bond; R<12> and R<13> independently of one another are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<14> is C1-C4alkyl; R<21> is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<22> is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, it being possible for the substituents to consist of C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<23> is hydrogen, C1-C6alkyl, C2-C6alkenyl, C1-C6alkoxy; phenyl or benzyl optionally substituted by C1-C4alkyl, C1-C4alkoxy group, C1-C4haloalkoxy group, C1-C4haloalkyl, halogen, cyano group, nitro group; which is a cyclohexane-1,3-dione ring, which is linked in the 2-position, of the formula II,   wherein R<15>, R<16>, R<18> and R<20> are hydrogen or C1-C4alkyl, R<19> is hydrogen, C1-C4alkyl or a group -COOR<14>, R<17> is hydrogen, C1-C4alkyl, C3-C4cycloalkyl, it being possible for these groups, if desired, to carry one to three of the following substituents: halogen, C1-C4alkylthio or C1-C4alkoxy, or R<17> is tetrahydropyranyl-3, tetrahydropyranyl-4 or tetrahydrothiopyranyl-3 or R<17> and R<20> together form a bond or a three to six-membered carbocyclic ring, wherein in the case if Y is C=O, X is not equal to NR<23>, and agriculturally utilizable salts. 2. A benzoyl derivative of the formula Ia   wherein L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4haloalkylthio, C1-C4alkylsulfonyl, halogen, nitro or cyano and M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4haloalkylthio, C1-C4alkylsulfonyl, halogen, nitro or cyano and Q, X, n and Y have the meanings given in claim 1, where in the case when Y is C=O, X is not equal to NR<23>. 3. A benzoyl derivative of the formula Ib   where L is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and Q, X, n and Y have the meanings given in claim 1, where in the case when Y is C=O, X is not equal to NR<23>. 4. The benzoyl derivatives of the formula I as claimed in claim 1, in which the radicals L, correspondingly M are hydrogen, methyl, methoxy group, chlorine, cyano group, nitro group, trifluoromethyl. 5. The benzoyl derivatives of the formula Ic   where L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and Q, n, Y and R<22>, R<21>, R<12> and R<13> have the meanings given in claim 1. 6. The benzoyl derivatives of the formula Id   wherein L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and Q, n, Y and R<12> and R<13> have the meanings given in claim 1. 7. The benzoyl derivatives of the formula Ie   wherein L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, nitro or cyano and Q, n, Y and R<12> and R<13> have the meanings given in claim 1. 8. The benzoyl derivatives of the formula I as claimed in claim 1, in which n is one or two and Y is CR<7>-OR<8>, where R<7> and R<8> have the meaning given in claim 1. 9. A process for preparing the compound of the formula I as claimed in claim 1, which comprises acylating the respective starting substances of the formula II   using an acid chloride of the formula IIIa or an acid IIIb,                    where L, M, X, n and Y have the meaning given in claim 1, and rearranging the acylation product in the presence of a caltalyst to give the compounds I. 10. A herbicidal composition comprising at least one benzoyl derivative of the formula I as claimed in claim 1 and customary inert additives. 11. The benzoyl derivatives of the formula IIIc   where T, L, M, X, n and Y have the following meanings: T is chlorine, OH or C1-C4alkoxy; L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4halothioalkyl, C1-C4alkylsulfonyl, halogen, nitro or cyano; M is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4halothioalkyl, C1-C4alkylsulfonyl, halogen, nitro or cyano; X, Y, and n are as given in claim 1, excluding the case when X is (-CH2CH2-) or (-CH2-) and Y is C=O or oxygen, L and M can not then simultaneously be hydrogen and if Y is C=O, X can not be NR<23>. 12. The benzoyl derivatives of the formula IIId   where T, L, M, X, n and Y have the following meanings: T is chlorine, OH or C1-C4alkoxy; L is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4halothioalkyl, C1-C4alkylsulfonyl, halogen or cyano; M is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4halothioalkyl, C1-C4alkylsulfonyl, halogen, nitro or cyano; X, Y, and n are as given in claim 1, wherein when Y is C=O, X can not be NR<23>.