N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition

Claim 1

A method of controlling weeds in the cultivation of a crop plant by applying a herbicidally effective amount of an N-(3-substituted oxyphenyl)-3,4,5,6-tetrahydrophthalimide of the formula: ##STR441## wherein X and Y each represent hydrogen or halogen; ##STR442## or --CN; R 1 is hydrogen or C 1-10 alkyl, phenyl chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl; R 2 is hydrogen or C 1-4 alkyl; R 3 is hydrogen or a C 1-12 straight or branched alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 1-5 haloalkyl, C 3-4 haloalkenyl, C 2-4 cyanoalkyl, C 2-4 hydroxyalkyl, C 3-6 alkoxyalkyl, C 5-8 alkoxyalkoxyalkyl, C 7-10 alkoxyalkoxyalkoxyalkyl, C 3-8 alkylthioalkyl, C 4-8 cycloalkyl, C 7-9 aralkyl, chlorobenzyl, bromobenzyl, phenyl, γ-butyrolactone optionally substituted by methyl, an alkali metal cation, an alkaline earth metal cation, ammonium cation, or an ammonium cation having 1 to 4 alkyl substituents, wherein the total carbon atom content of the ammonium cation is 1 to 9 carbon atoms; R 4 is C 1-12 alkyl, C 3-6 alkoxycarbonylalkyl or benzyl; R 5 is hydrogen or methyl; R 6 is methyl or phenyl; R 7 and R 8 can be the same or different and each is hydrogen, C 1-10 branched or straight chain alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 2-6 haloalkyl, C 2-6 hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, chlorophenyl, bromophenyl, methylphenyl, methoxyphenyl, pyrimidine, thiazole, pyridine, C 1-6 alkoxy, C 2-4 alkenyloxy, amino, methylamino, phenylamino, dimethylamino, C 1-4 alkanesulfonyl, benzenesulfonyl, toluenesulfonyl, chlorobenzenesulfonyl, methoxybenzenesulfonyl or cyclohexyl; and ##STR443## wherein R 7 and R 8 together form a piperidine, or optionally together with an oxygen form a morpholine, isoxazolidine, or tetrahydroisoxazine ring; and m and n each represent an integer of 1 to 3.

Claim 2

A method of controlling weeds in the cultivation of a crop plant by applying a herbicidally effective amount of an N-(3-substituted oxyphenyl)-3,4,5,6-tetrahydrophthalimide of the formula: ##STR441## wherein X and Y each represent hydrogen or halogen; ##STR442## or --CN; R 1 is hydrogen or C 1-10 alkyl, phenyl chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl; R 2 is hydrogen or C 1-4 alkyl; R 3 is hydrogen or a C 1-12 straight or branched alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 1-5 haloalkyl, C 3-4 haloalkenyl, C 2-4 cyanoalkyl, C 2-4 hydroxyalkyl, C 3-6 alkoxyalkyl, C 5-8 alkoxyalkoxyalkyl, C 7-10 alkoxyalkoxyalkoxyalkyl, C 3-8 alkylthioalkyl, C 4-8 cycloalkyl, C 7-9 aralkyl, chlorobenzyl, bromobenzyl, phenyl, γ-butyrolactone optionally substituted by methyl, an alkali metal cation, an alkaline earth metal cation, ammonium cation, or an ammonium cation having 1 to 4 alkyl substituents, wherein the total carbon atom content of the ammonium cation is 1 to 9 carbon atoms; R 4 is C 1-12 alkyl, C 3-6 alkoxycarbonylalkyl or benzyl; R 5 is hydrogen or methyl; R 6 is methyl or phenyl; R 7 and R 8 can be the same or different and each is hydrogen, C 1-10 branched or straight chain alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 2-6 haloalkyl, C 2-6 hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, chlorophenyl, bromophenyl, methylphenyl, methoxyphenyl, pyrimidine, thiazole, pyridine, C 1-6 alkoxy, C 2-4 alkenyloxy, amino, methylamino, phenylamino, dimethylamino, C 1-4 alkanesulfonyl, benzenesulfonyl, toluenesulfonyl, chlorobenzenesulfonyl, methoxybenzenesulfonyl or cyclohexyl; and ##STR443## wherein R 7 and R 8 together form a piperidine, or optionally together with an oxygen form a morpholine, isoxazolidine, or tetrahydroisoxazine ring; and m and n each represent an integer of 1 to 3.

Claim 10

The method of claims 1, 3 or 4, wherein in said tetrahydrophthalimide compound, ##STR445## R 1 represents hydrogen or C 1-10 alkyl, phenyl, chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl; R 2 represents hydrogen or C 1-14 alkyl; R 3 represents hydrogen, C 1-12 straight or branched alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 1-5 haloalkyl, C 3-4 haloalkenyl, C 2-4 cyanoalkyl, C 2-4 hydroxyalkyl, C 3-6 alkoxyalkyl, C 5-8 alkoxyalkoxyalkyl, C 7-10 alkoxyalkoxyalkoxyalkyl, C 3-8 alkylthioalkyl, C 4-8 cycloalkyl, C 7-9 aralkyl, chlorobenzyl, bromobenzyl, phenyl, γ-butyrolactone optionally substituted by methyl, an alkali metal cation, an alkaline earth metal cation, ammonium cation or an ammonium cation containing from 1 to 4 alkyl groups, wherein the total carbon atom content of the ammonium cation is 1 to 9 carbon atoms; R 4 represents C 1-12 alkyl, C 3-6 alkoxycarbonylalkyl or benzyl; R 5 represents hydrogen of methyl; R 6 represents methyl or phenyl; and n and m are each an integer of 1 to 3.

Claim 13

The method of claims 1, 3 or 4, wherein in said tetrahydrophthalimide compound, group A represents --(CHR 1 ) n --; R 1 represents H or an alkyl group; n is an integer of 1 to 3 and B represents CN.