Claims
- 1. A compound having the formula I structure: ##STR45## wherein X is hydrogen, halogen or methyl;
- Y and Z are each hydrogen, halogen,
- C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.3 alkoxy;
- C.sub.1 -C.sub.3 alkoxy, phenoxy, C.sub.1 -C.sub.3 haloalkyl, trifluoromethoxy, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.4 alkylthio, formyl, difluoromethoxy, 1,1,2,2-tetrafluoroethoxy, nitro, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.6 alkenyl optionally substituted with halogen;
- C.sub.2 -C.sub.6 alkynyl optionally substituted with halogen;
- or phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, or halogen;
- and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: --(CH.sub.2).sub.n --, where n is an integer of 3 or 4; or ##STR46## where L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, nitro, cyano, phenyl optionally substituted with halogen or C.sub.1 -C.sub.3 alkyl;
- phenoxy optionally substituted with halogen, trifluoromethyl, nitro or C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 alkenyl optionally substituted with halogen; or C.sub.3 -C.sub.6 alkynyl optionally substituted with halogen;
- A is CR.sub.6 ;
- B is hydroxyl, cyano, halogen, SR.sub.4, ##STR47## R.sub.1 is C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl;
- and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
- R.sub.3 is hydrogen,
- C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.3 alkoxy, halogen, C.sub.3 -C.sub.6 cycloalkyl, benzyl, furyl, trimethylsilyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, or nitrophenyl;
- C.sub.3 -C.sub.6 alkenyl optionally substituted with C.sub.1 -C.sub.3 alkoxy, phenyl, halogen or C.sub.1 -C.sub.4 alkoxycarbonyl;
- C.sub.3 -C.sub.6 cycloalkyl optionally substituted with C.sub.1 -C.sub.3 alkyl;
- C.sub.3 -C.sub.6 alkynyl optionally substituted with C.sub.1 -C.sub.3 alkyl; or
- a cation of alkali metals, ammonium or organic ammonium;
- R.sub.4 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted with nitro, CO.sub.2 R.sub.8, cyano, trifluoromethyl, difluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, or halogen;
- R.sub.5 is C.sub.1 -C.sub.4 alkyl;
- R.sub.6 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or 1,1,2-2-tetrafluoroethoxy;
- R.sub.8 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- the N-oxides thereof, when R.sub.3 is not unsaturated alkyl and Y and Z cannot be unsaturated alkyl or alkylthio;
- the optical isomers thereof, when R.sub.1 and R.sub.2 represent different substituents; and
- the acid addition salts thereof, when R.sub.3 is other than a cation.
- 2. A method for controlling undesirable plant species which comprises applying to the foliage of said plants or to the soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of a compound having the structure: ##STR48## wherein X is hydrogen, halogen or methyl;
- Y and Z are each hydrogen, halogen,
- C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.3 alkoxy;
- C.sub.1 -C.sub.3 alkoxy, phenoxy, C.sub.1 -C.sub.3 haloalkyl, trifluoromethoxy, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.4 alkylthio, formyl, difluoromethoxy, 1,1,2,2-tetrafluoroethoxy, nitro, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.6 alkenyl optionally substituted with halogen;
- C.sub.2 -C.sub.6 alkynyl optionally substituted with halogen;
- or phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, or halogen;
- and, when taken together, Y and Z may form a ring in which YZ are represented by the structure: --(CH.sub.2).sub.n --, where n is an integer of 3 or 4; or ##STR49## where L, M, Q and R.sub.7 are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, nitro, cyano, phenyl optionally substituted with halogen or C.sub.1 -C.sub.3 alkyl;
- phenoxy optionally substituted with halogen, trifluoromethyl, nitro or C.sub.1 -C.sub.3 alkyl; C.sub.3 -C.sub.6 alkenyl optionally substituted with halogen; or C.sub.3 -C.sub.6 alkynyl optionally substituted with halogen;
- A is CR.sub.6 ;
- B is hydroxyl, cyano, halogen, SR.sub.4, ##STR50## R.sub.1 is C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl;
- and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
- R.sub.3 is hydrogen,
- C.sub.1 -C.sub.6 alkyl optionally substituted with C.sub.1 -C.sub.3 alkoxy, halogen, C.sub.3 -C.sub.6 cycloalkyl, benzyl, furyl, trimethylsilyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, or nitrophenyl;
- C.sub.3 -C.sub.6 alkenyl optionally substituted with C.sub.1 -C.sub.3 alkoxy, phenyl, halogen or C.sub.1 -C.sub.4 alkoxycarbonyl;
- C.sub.3 -C.sub.6 cycloalkyl optionally substituted with C.sub.1 -C.sub.3 alkyl;
- C.sub.3 -C.sub.6 alkynyl optionally substituted with C.sub.1 -C.sub.3 alkyl; or
- a cation of alkali metals, ammonium or organic ammonium;
- R.sub.4 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted with nitro, CO.sub.2 R.sub.8, cyano, trifluoromethyl, difluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, or halogen;
- R.sub.5 is C.sub.1 -C.sub.4 alkyl;
- R.sub.6 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or 1,1,2-2-tetrafluoroethoxy;
- R.sub.8 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- the N-oxides thereof, when R.sub.3 is not unsaturated alkyl and Y and Z cannot be unsaturated alkyl or alkylthio;
- the optical isomers thereof, when R.sub.1 and R.sub.2 represent different substituents; and
- the acid addition salts thereof, when R.sub.3 is other than a cation.
- 3. The method according to claim 2, which comprises applying said compound to the foliage of said plants at a rate of about 0.016 kg/ha to 4.0 kg/ha.
- 4. The method according to claim 2, which comprises applying said compound to the soil or water containing seeds or other propagating organs of said plants at a rate of about 0.016 kg/ha to 4.0 kg/ha.
- 5. A composition for controlling undesirable plant species which comprises an agronomically acceptable carrier and a herbicidally effective amount of a 2-(1-substituted-2-imidazolin-2-yl)benzoic or nicotinic acid, ester or salt compound as described in claim 1.
Parent Case Info
This is a divisional of co-pending application Ser. No. 07/762,836 filed on Sep. 19, 1991 (now U.S. Pat. No. 5,213,607) which is a divisional of Ser. No. 07/453,659 filed on Dec. 20, 1989, now U.S. Pat. No. 5,062,881.
US Referenced Citations (8)
Divisions (2)
|
Number |
Date |
Country |
Parent |
762836 |
Sep 1991 |
|
Parent |
453659 |
Dec 1989 |
|