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US 5,180,417 AGranted
4-((aryloxy)phenoxy)fluoroalkanoic acid derivatives and their herbicidal uses
AssigneeDowElanco
InventorJames A. Turner
Life of this patent
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Abstract
Disclosed herein are derivatives of 4-((aryloxy)phenoxy)fluoroalkanoic acid and their use as active herbicides for the pre- and postemergent control of grassy weeds, especially in the presence of broadleaf crops.
Claims12
A compound or an optical isomer thereof corresponding to the formula ##STR31## wherein Ar represents ##STR32## each Y independently represents --H or --F;
- G represents, in the 5 or 6 ring position, --Br, --Cl, --F or --CF.sub.3 :
- R.sup.1 represents --CH.sub.2 OH, --CN, --COOH, --COOM --COOR.sup.2, ##STR33## X.sup.1 represents --Br or --Cl;
- L represents oxygen or sulfur;
- M represents an agriculturally acceptable cation;
- R.sup.2 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.12 alkyl substituted with 1 or 2 bromo, chloro, fluoro or C.sub.1 -C.sub.4 alkoxy substituents or R.sup.2 represents phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro substituents or R.sup.2 represents the radical --N.dbd.C(R.sup.3).sub.2 wherein each R.sup.3 independently represents a C.sub.1 -C.sub.4 alkyl;
- R.sup.4 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro groups;
- R.sup.5 represents hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 cycloalkyl, --CN --SO.sub.2 CH.sub.3, --OR.sup.2 wherein R.sup.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, --NHR.sup.7, phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro groups;
- and
- R.sup.6 represents hydrogen, methyl, ethyl, C.sub.3 alkenyl, C.sub.3 alkynyl or cyclopropyl.
6 more elements
A composition which comprises an agriculturally acceptable inert adjuvant in intimate admixture with a herbicidally effective amount of a compound, as the active material, which corresponds to the formula ##STR36## wherein Ar represents ##STR37## each Y independently represents --H or --F;
- G represents, in the 5 to 6 ring position, --Br, --Cl, --F, or --CF.sub.3 ;
- R.sup.1 represents --CH.sub.2 OH, --CN, --COOH, --COOM, --COOR.sup.2, ##STR38## X.sup.1 represents --Br or --Cl;
- L represents oxygen or sulfur;
- M represents an agriculturally acceptable cation;
- R.sup.2 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.12 alkyl substituted with 1 or 2 bromo, chloro, fluoro or C.sub.1 -C.sub.4 alkoxy substituents or R.sup.2 represents phenyl substituted with 1 or 2 bromo, chloro fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro substituents or R.sup.2 represents the radical --N.dbd.C(R.sup.3).sub.2 wherein each R.sup.3 independently represents a C.sub.1 -C.sub.4 alkyl;
- R.sup.4 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl, phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxyl or nitro groups:
- R.sup.5 represents hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 cycloalkyl, --CN, --SO.sub.2 CH.sub.3, --OR.sup.7 wherein R.sup.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, --NHR.sup.7, phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro groups;
- and
- R.sup.6 represents hydrogen, methyl, ethyl, C.sub.3 alkenyl, C.sub.3 alkynyl or cyclopropyl.
6 more elements
A method for the postemergent kill and control of grassy weeds which comprises applying to said weeds a herbicidally effective amount of a composition comprising an agriculturally acceptable inert adjuvant in intimate admixture with, as the active material, a compound corresponding to one of the formulae ##STR41## wherein Ar represents ##STR42## each Y independently represents --H or --F;
- G represents, in the 5 or 6 ring position, --Br, --Cl, --F or --CF.sub.3 ;
- R.sup.1 represents --CH.sub.2 OH, --CN, --COOH, --COOM, --COOR.sup.2, ##STR43## X.sup.1 represents --Br or --Cl;
- L represents oxygen or sulfur;
- M represents an agriculturally acceptable cation;
- R.sup.2 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.12 alkyl substituted with 1 or 2 bromo, chloro, fluoro or C.sub.1 -C.sub.4 alkoxy substituents or R.sup.2 represents phenyl substituted with 1 or 2 bromo, chloro fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro substituents or R.sup.2 represents the radical --N.dbd.C(R.sup.3).sub.2 wherein each R.sup.3 independently represents a C.sub.1 -C.sub.4 alkyl;
- R.sup.4 represents C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkenyl, C.sub.3 -C.sub.12 alkynyl, C.sub.3 -C.sub.12 cycloalkyl, phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.4 alkoxy or nitro groups;
- R.sup.5 represents hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 cycloalkyl, --CN, --SO.sub.2 CH.sub.3, --OR.sup.7 wherein R.sup.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, --NHR.sup.7, phenyl or phenyl substituted with 1 or 2 bromo, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro groups;
- and R.sup.6 represents hydrogen, methyl, ethyl, C.sub.3 alkenyl, C.sub.3 alkynyl or cyclopropyl.
5 more elements
Dependencies are inferred from the claim text.