Claims
- 1. A benzoyl compound of the formula I ##STR302## where the substituents have the following meanings: L and M are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, where these groups may carry one to five halogen atoms or C.sub.1 -C.sub.4 -alkoxy; halogen, cyano, nitro, a group --(A).sub.m --S(O).sub.n R.sup.1 or a group --(A).sub.m --CO--R.sup.2 ;
- Y is CR.sup.10 R.sup.11 ;
- X is --CR.sup.12 R.sup.13 --CR.sup.21 R.sup.22 -- or --CR.sup.12 .dbd.CR.sup.13 --;
- the bond between X and Y can be saturated or unsaturated;
- A is O or NR.sup.14 ;
- m is zero or one;
- n is zero, one or two;
- R.sup.1 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or NR.sup.14 ;
- R.sup.2 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or NR.sup.14 ;
- R.sup.10, R.sup.11 independently of one another are hydrogen, C.sub.1 -C.sub.6 -alkyl; unsubstituted or substituted phenyl, wherein the substituents are selected from the group consisting of one to three halogens, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and nitro; R.sup.10 and R.sup.12 or R.sup.10 and R.sup.21 can form a bond;
- R.sup.12 and R.sup.13 independently of one another are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy; unsubstituted or substituted phenyl, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkyl, halogen, cyano and nitro;
- R.sup.14 is C.sub.1 -C.sub.4 -alkyl;
- R.sup.21 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy; unsubstituted or substituted phenyl, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkyl, halogen, cyano and nitro;
- R.sup.22 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy; unsubstituted or substituted phenyl, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkyl, halogen, cyano and nitro;
- Q is a cyclohexane-1,3-dione ring, which is linked in the 2-position, of the formula II ##STR303## where R.sup.15, R.sup.16, R.sup.18 and R.sup.20 are hydrogen or C.sub.1 -C.sub.4 -alkyl,
- R.sup.19 is hydrogen, C.sub.1 -C.sub.4 -alkyl or a group --COOR.sup.14,
- R.sup.17 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -cycloalkyl, where these groups may carry one to three of the following substituents: halogen, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -alkoxy, or
- R.sup.17 is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl, or
- R.sup.17 and R.sup.20 together form a bond or a three to six-membered carbocyclic ring,
- or an agriculturally utilizable salt thereof.
- 2. A benzoyl compound of the formula Ia ##STR304## where L is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano,
- M is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano, and
- Q, X, n and Y have the meanings given in claim 1.
- 3. A benzoyl compound of the formula Ib ##STR305## where L is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano,
- M is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano, and
- Q, X, n and Y have the meanings given in claim 1.
- 4. The benzoyl compound of the formula I as defined in claim 1 where the radicals L and M are hydrogen, methyl, methoxy, chlorine, cyano, nitro or trifluoromethyl.
- 5. A benzoyl compound of the formula Ic ##STR306## where L is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano,
- M is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano, and
- Q, n, Y and R.sup.22, R.sup.21, R.sup.12 and R.sup.13 have the meanings given in claim 1.
- 6. A benzoyl compound of the formula Ie ##STR307## where L is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano,
- M is hydrogen, C.sub.1 -C-C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano, and
- Q, n, Y and R.sup.12 and R.sup.13 have the meanings given in claim 1.
- 7. A herbicidal composition comprising at least one benzoyl compound of the formula I as defined in claim 1 and customary inert additives.
- 8. A method of controlling undesirable vegetation, which comprises allowing a herbicidally active amount of a benzoyl compound of the formula I as defined in claim 1 to act on the plants or their environment.
- 9. A process for preparing a compound of the formula I as defined in claim 1, which comprises acylating a 1,3-cyclohexanedione of the formula II ##STR308## with an acid chloride of the formula IIIa or an acid IIIb, ##STR309## and rearranging the acylation product in the presence of a catalyst to give the compound I.
- 10. A benzoyl compound of the formula IIIc ##STR310## where T, L, M, X, n and Y have the following meanings: T is chlorine, OH or C.sub.1 -C.sub.4 -alkoxy;
- L is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halothioalkyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano;
- M is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halothioalkyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano;
- X is --CR.sup.12 R.sup.13 --CR.sup.21 R.sup.22 -- or --CR.sup.12 .dbd.CR.sup.13 --;
- Y is CR.sup.10 R.sup.11 ;
- n is zero, one or two.
- 11. A benzoyl compound of the formula IIId ##STR311## where T, L, M, X, n and Y have the following meanings: T is chlorine, OH or C.sub.1 -C.sub.4 -alkoxy;
- L is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halothioalkyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen or cyano;
- M is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halothioalkyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano;
- X is --CR.sup.12 R.sup.13 --CR.sup.21 R.sup.22 -- or --CR.sup.12 .dbd.CR.sup.13 --;
- Y is CR.sup.10 R.sup.11 ;
- n is zero, one or two.
Priority Claims (1)
Number |
Date |
Country |
Kind |
195 32 311 |
Sep 1995 |
DEX |
|
Parent Case Info
This application is a 371 of PCT/EP96/03800 filed Aug. 29, 1996.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP96/03800 |
8/29/1996 |
|
|
2/26/1998 |
2/26/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO97/09324 |
3/13/1997 |
|
|
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