Patent EA-001884-B1 (EA)
Title: Cyclohexanedione derivatives and herbicides prepared therefrom
Inventor: FRECHET JEAN M J
IPC: C07D335/06
Filed: 1997-12-24
Abstract: 1. Cyclohexanedione derivatives of the general formula (I)   or the salt thereof wherein each of R<1> and R<6> is independently a hydrogen atom or a C1-C6 alkyl group, n is 2, X is a C1-C6 alkyl group, a C1-C6 haloakyl group, or a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, Z is a group (a) or (b),   in which each of R<7> and R<8> is independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkoxy group, provided that when R<7>, R<8> or both are C1-C6 alkyl, or C1-C6 alkoxy group(s), 1 to 13 hydrogen atoms may be substituted with 1 to 13 halogen atoms or C1-C6 alkoxy groups, and when the number of carbon atoms therein is C2-C6 , the group(s) may contain an unsaturated bond, and when the number of carbon atoms therein is C3-C6 , the group(s) may have cycle structure, and  further provided that when both R<7> and R<8> are alkyl groups, compounds of the general formula (I) in which X is a C1-C6 alkyl group, a halogen atom or a haloalkyl group and all of R<3>, R<4>, R<5> and R<6> are hydrogen atoms are excluded, provided that when one of R<7> and R<8> is an alkoxy group and when the other is a hydrogen atom, compounds of the general formula (I) in which X is a C1-C6 alkyl group and all of R<3>, R<4>, R<5> and R<6> are hydrogen atoms when no hydrogen atom of the alkoxy group is replaced with halogen or when the alkoxy group contains no unsaturated bond are excluded, and R<9> is an oxygen atom, or a C1-C6 alkoxyimino-group, provided that compounds of the general formula (I) in which X is a C1-C6 alkyl group and all of R<3>, R<4>, R<5> and R<6> are hydrogen atoms when R<9> is an alkoxyimino group and when no hydrogen atom thereof is replaced with a halogen or the alkoxyimino group contains no unsaturated bond are excluded, and Q is hydroxyl group or (c) group,   wherein R<16> is C1-C6 alkyl group. 2. Cyclohexanedione derivatives of the general formula (I-a1)   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, n is 2, X is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, R<12> is a C1-C6 alkyl group or a C1-C6 haloalkyl group, provided that R<12> may be substituted with a C1-C6 alkoxy group, and when the number of carbon atoms in R<12> is C2-C6 , R<12> may contain an unsaturated bond, and when the number of carbon atoms in R<12> is C1-C6 , R<12> may have cycle structure, and further, when R<12> is C1-C6 alkyl group, compounds of the general formula (I-a1) in which X is a C1-C6 alkyl group and all of R<3>, R<4>, R<5> and R<6> are hydrogen atoms, are excluded, and Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 3. Cyclohexanedione derivatives of the general formula (I-a2),   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, R<13> is a C1-C6 alkyl group, n is 2, X<1> is a C1-C6 haloalkyl group, a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 4. Cyclohexanedione derivatives of the general formula (I-a3),   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, R<14> is a C1-C6 haloalkyl group, alkoxyalkyl group, alkenyl group or alkynylalkyl group n is 2, X<2> is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 5. Cyclohexanedione derivatives of the general formula (I-b1),   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, R<15> is a C1-C6 alkyl group or C1-C6 alkenyl group, n is 2, X is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, provided that when R<15> is a C1-C6 alkyl group, provided that compounds of the general formula (I-b1) in which X is a C1-C6 alkyl group and all of R<3>, R<4>, R<5> and R<6> are hydrogen atoms are excluded, and Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 6. Cyclohexanedione derivatives of the general formula (I-b2),   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, R<13> is a C1-C6 alkyl group, n is 2, X<1> is a C1-C6 haloalkyl group, or a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 7. Cyclohexanedione derivatives of the general formula (I-c),   wherein each of R<1> to R<6> is independently a hydrogen atom or a C1-C6 alkyl group, n is 2, X<2> is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a halogen atom, Y is a hydrogen atom, a C1-C6 alkyl group, or a halogen atom, Q is hydroxyl group or (c) group,   wherein R<16> is a C1-C6 alkyl group or a salt thereof. 8. The cyclohexanedione derivatives according to any of Claims 1-7, wherein each of R<3>, R<4>, R<5> and R<6> is independently a hydrogen atom or methyl. 9. The cyclohexanedione derivatives according to any of Claims 1-7, wherein Y is substituted on the 8-position of a thiochroman ring. 10. Herbicides containing, as active ingredients, the cyclohexanedione derivatives or the salts thereof recited in any of Claims 1-9.