Patent EA-001930-B1 (EA)
Title: 2-hetaroylcyclohexane-1,3-diones
Inventor: OTTEN MARTINA
IPC: C07D327/06
Filed: 1997-02-20
Abstract: 1. A hetaroyl derivative of the formula I   where the substituents have the following meanings: L and M are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen, cyano, nitro; X is oxygen or sulfur which can be substituted by one or two oxygens; n is zero, one, two; R<1> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen; phenyl which can be monosubstituted or polysubstituted by the following groups: C1-C4-alkyl, hydrogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, nitro, cyano, C1-C4-alkyloxycarbonyl; R<2> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen; phenyl which can be monosubstituted or polysubstituted by the following groups: C1-C4-alkyl, hydrogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, nitro, cyano, C1-C4-alkyloxycarbonyl; R<2> and R<3> can form a bond; R<3> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen; phenyl which can be monosubstituted or polysubstituted by the following groups: C1-C4-alkyl, hydrogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, nitro, cyano, C1-C4-alkyloxycarbonyl; R<3> and R<2> can form a bond; R<4> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen; phenyl which can be monosubstituted or polysubstituted by the following groups: C1-C4-alkyl, hydrogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, nitro, cyano, C1-C4-alkyloxycarbonyl; Q is a cyclohexane-1,3-dione ring, linked in the 2-position, of the formula II   where the substituents have the following meanings: R<5>, R<6> and R<10> hydrogen, C1-C4-alkyl; R<7> hydrogen, C1-C4-alkyl, C3-C4-cycloalkyl, it being possible for these groups, if desired, to carry one to three of the following substituents: halogen, C1-C4-thioalkyl or C1-C4-alkoxy; or R<7> is C1-C4-alkoxy; C1-C6-alkoxyalkyl, tetrahydropyranyl-3, tetrahydropyranyl-4; or R<7> and R<9> can together form a bond or a three- to six-membered carbocyclic ring; R<8> is hydrogen, C1-C4-alkyl; R<9> is hydrogen, C1-C4-alkyl or a group COOR<11>; R<11> is C1-C4-alkyl; or agriculturally utilizable salts. 2. A hetaroyl derivative of the formula Ia   where L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and Q, X, R<1>-R<4> and n have the meanings given in Claim 1. 3. A hetaroyl derivative of the formula Ib   where L is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and Q, X, R<1>-R<4> and n have the meanings given in Claim 1. 4. A hetaroyl derivative of the formula I as claimed in Claim 1 where the radicals L and M are hydrogen, methyl, methoxy, chlorine, cyano, nitro and trifluoromethyl. 5. A hetaroyl derivative of the formula Ic   where L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and Q, R<1>-R<4> and n have the meanings given in Claim 1. 6. A hetaroyl derivative of the formula Id1   where L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and Q, R<1>, R<4> and n have the meanings given in Claim 1. 7. A hetaroyl derivative of the formula Id2   where L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro, and m is zero, one or two and Q, R<1>, R<4> and n have the meanings given in Claim 1. 8. A hetaroyl derivative of the formula Ie   where L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, cyano or nitro, and m is zero, one or two and Q, R<1>-R<4> and n have the meanings 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 chloroanhydride acid of the formula IIIa or an acid of the formula IIIb   where L, M, X, R<1> to R<4> and n have the meanings mentioned in Claim 1, and rearranging the acylation product to the compounds I in the presence of a catalyst. 10. A hetaroyl derivative of the formula IIIc   where T, L, M, X, R<1> to R<4> and n have the following meanings: T is chlorine, OH or C1-C4-alkoxy; L is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen, cyano, nitro; M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen, cyano, nitro; X, R<1>, R<2>, R<3>, R<4> and n are as given in Claim 1. 11. A hetaroyl derivative of the formula IIId   where T, L, M, X, R<1> to R<4> and n have the following meanings: T is chlorine, OH or C1-C4-alkoxy; L is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen, cyano, nitro; M is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4-alkoxy; halogen, cyano, nitro; X, R<1>, R<2>, R<3>, R<4> and n are as given in Claim 1. 12. A herbicidal composition, comprising at least one hetaroyl derivative of the formula I as claimed in Claim 1 and additives. 13. A method of controlling undesired plant growth, which comprises allowing a herbicidally active amount of a hetaroyl derivative of the formula I as claimed in Claim 1 to act on the plants or their habitat.