Claims
- 1. A 2-benzoylcyclohexane-1,3-dione of formula I where the variables have the following meanings: R1, R2 are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, —OR5, —OCOR6, —OSO2R6, —SH, —S(O)nR7, —SO2OR5, —SO2NR5R8, —NR8SO2R6 or —NR8COR6; R3 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl; R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, —COR9, —CO2R9, —COSR9 or —CONR8R9, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and for R9 of the radicals —COR9, —CO2R9, —COSR9 and —CONR8R9 to be partially or fully halogenated and/or to have attached to them one to three of the following groups: hydroxyl, mercapto, amino, cyano, R10, —OR10, —SR10, —NR8R10, ═NOR10, —OCOR10, —SCOR10, —NR8COR10, —CO2R10, —COSR10, —CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy, phenyl-C1-C4-alkoxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted; X is oxygen or sulfur; z is oxygen or NR8; m is 0 or 1; n is 0, 1 or 2; R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R6 is C1-C6-alkyl or C1-C6-haloalkyl; R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R8 is hydrogen or C1-C6-alkyl; R9 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl; R10 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl; Q is a cyclohexane-1,3-dione ring of formula II wherein R11, R12, R14 and R16 are hydrogen or C1-C4-alkyl; R13 is hydrogen, C1-C4-alkyl or C3-C4-cycloalkyl, it being possible for the two last-mentioned groups to have attached to them one to three of the following substituents: halogen, C1-C4-alkylthio or C1-C4-alkoxy; or is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahy-dropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothio-pyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,4-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-di-thian-2-yl, it being possible for the 6 last-mentioned radicals to be substituted by one to three C1-C4-alkyl radicals; R15 is hydrogen, C1-C4-alkyl or C1-C6-alkoxycarbonyl; or R13 and R16 together form a π bond or a three to six-membered carbocyclic ring; or the CR13R14 unit represents a C═O group; where m is 1 if R3 is hydrogen; or an agriculturally useful salt thereof.
- 2. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 whereinR1 is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, —OR5 or —S(O)nR7; R2 is hydrogen or a radical as mentioned above for R1.
- 3. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein m is 1.
- 4. The 2-benzoylcyclohexane-1,3-dione defined in claim 1 which is of formula Ia
- 5. A process for the preparation of the 2-benzoylcyclo-hexane-1,3-dione of formula I defined in claim 1, 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 L1 is a nucleophilically displaceable leaving group, and, if appropriate, subjecting the acylation product to a rearrangement reaction in the presence of a catalyst to give the compounds I.
- 6. A benzoic acid derivative of formula IIIa where R1, R2 are nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, —OR5 or —S(O)nR7; R3 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl; R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, —COR9, —CO2R9, —COSR9 or —CONR8R9, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and for R9 of the radicals —COR9, —CO2R9, —COSR9 and —CONR8R9 to be partially or fully halogenated and/or to have attached to them one to three of the following groups: hydroxyl, mercapto, amino, cyano, R10, —OR10, —SR10, —NR8R10, ═NOR10, —OCOR10, —SCOR10, —NR8COR10, —CO2R10, —COSR10, —CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy, phenyl-C1-C4-alkoxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted; X is oxygen or sulfur; Z is oxygen or NR8; m is 1; n is 0, 1 or 2; R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R17 is hydroxyl or a radical which can be removed by hydrolysis; where R4 is not hydrogen if Z is NH and R1 and R2 are chlorine.
- 7. The benzoic acid derivative of formula IIIa defined in claim 6, wherein R17 is halogen, hydroxyl or C1-C6-alkoxy.
- 8. A composition comprising a herbicidally active amount of at least one 2-benzoylcyclohexane-1,3-dione of formula I or of an agriculturally useful salt of I defined in claim 1 and auxiliaries conventionally used for the formulation of crop protection products.
- 9. A process for the preparation of herbicidally active composition defined in claim 8, which comprises mixing a herbicidally active amount of at least one 2-benzoyl-cyclohexane-1,3-dione of formula I or of an agriculturally useful salt of I and auxiliaries conventionally used for the formulation of crop protection products.
- 10. A method of controlling undesirable vegetation, which comprises allowing a herbicidally active amount of at least one 2-benzoylcyclohexane-1,3-dione of formula I or of an agriculturally useful salt of I defined in claim 1 to act on plants, their environment and/or on seeds.
- 11. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein R3 is hydrogen, methyl, ethyl, propyl, butyl, difluoromethyl or trifluoromethyl.
- 12. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein X is oxygen.
- 13. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein Z is oxygen, NH or N—CH3.
- 14. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein R11, R12, R14 and R15 are each hydrogen, methyl or ethyl.
- 15. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein R15 is hydrogen, methyl or ethyl.
- 16. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein CR13R14 represents a C═O group.
- 17. The 2-benzoylcyclohexane-1,3-dione defined in claim 1 which is of formula Ia′ wherein R1 is halogen or C1-C4-alkylsulfonyl; R2 is halogen or C1-C4-alkyl; R3 is hydrogen or C1-C4-alkyl; R4 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, it being possible for the two last-mentioned substituents to be partially or fully halogenated and/or to have attached to them one to three of the following froups: phenyl, phenyl-C1-C4-alkyl, hetaryl or phenoxy, it being possible for the 4 last-mentioned radicals to be partially or fully halogenated; X is oxygen; Z is oxygen or NH; m is 0 or 1; R11, R12, R14, R15 and R16 are hydrogen or C1-C4-alkyl; R13 is hydrogen, C1-C4-alkyl, tetrahydropyran-3-yl, tetrahydro-thiopyran-3-yl or 1,4-dioxan-2-yl; or the CR13R14 unit represents a C═O group.
- 18. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 wherein R15 is H or C1-C4-alkyl.
- 19. The 2-benzoylcyclohexane-1,3-dione of formula I defined in claim 4 wherein R15 is H or C1-C4-alkyl.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 197 00 097 |
Jan 1997 |
DE |
|
Parent Case Info
This application is a 371 of PCT/EP97/07211, filed Dec. 19, 1997.
PCT Information
| Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
| PCT/EP97/07211 |
|
WO |
00 |
6/23/1999 |
6/23/1999 |
| Publishing Document |
Publishing Date |
Country |
Kind |
| WO98/29383 |
7/9/1998 |
WO |
A |
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
| 4943310 |
Angermann et al. |
Jul 1990 |
|
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Non-Patent Literature Citations (1)
| Entry |
| Crossfire, Beilstein, XP002063835, 1970. |
Patent Grant
6310245
