Safening 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide injury on cereal crops
View Patent ↗Herbicidal injury caused by 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylates in wheat and barley is reduced with the use of a safener selected from the group consisting of cloquintocet, fenchlorazole, mefenpyr and mixtures thereof.
1. A composition for protecting wheat and barley from the harmful effects of a 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide of the formula (I)
wherein
Q represents a C 2 -C 4 alkenyl or C 1 -C 4 alkoxy;
X represents H or halogen;
Y represents H, halogen, C 1 -C 4 alkoxy, or —NR 1 R 2 ;
Z represents halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and
R 1 and R 2 independently represent H or C 1 -C 4 alkyl;
or an agriculturally acceptable salt, ester, or amide derivative thereof, which comprises, in addition to the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide, a safener which is cloquintocet acid or cloquintocet-mexyl;
wherein the weight ratio of the safener to the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is in the range of 1:16 to 4:1.
2. The composition of claim 1 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid; 6-amino-2-(4-trifluoromethylphenyl)-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-2-tluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-p-tolyl-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-3-dimethylamino-2-fluorophenyl)-5-vinylpyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-3-fluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; or 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; or an agriculturally acceptable salt, ester, or amide thereof.
3. The composition of claim 2 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid methyl ester or 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid methyl ester.
4. The composition of claim 1 in which the weight ratio of the safener to 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is in the range of 1:4 to 2:1.
5. The composition of claim 1 , wherein Q represents a C 2 -C 4 alkenyl.
6. The composition of claim 1 , wherein Q represents a C 1 -C 4 alkoxy.
7. The composition of claim 1 in which the safener is cloquintocet-mexyl.
8. A method of protecting wheat or barley from the harmful effects of a 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide of the formula (I)
wherein
Q represents a C 2 -C 4 alkenyl or C 1 -C 4 alkoxy;
X represents H or halogen;
Y represents H, halogen, C 1 -C 4 alkoxy, or —NR 1 R 2 ;
Z represents halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and
R 1 and R 2 independently represent H or C 1 -C 4 alkyl;
or an agriculturally acceptable salt, ester, or amide derivative thereof, which comprises contacting the wheat or barley with, or applying to the area under cultivation, in addition to the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide, a safener which is cloquintocet acid or cloquintocet-mexyl; wherein the weight ratio of the safener to the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is in the range of 1:16 to 4:1.
9. The method of claim 8 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid; 6-amino-2-(4-trifluoromethylphenyl)-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-p-tolyl-5-methoxypyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-3-dimethylamino-2-fluorophenyl)-5-vinylpyrimidine-4-carboxylic acid; 6-amino-2-(4-chloro-3-fluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; or 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; or an agriculturally acceptable salt, ester, or amide thereof.
10. The method of claim 9 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid methyl ester or 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid methyl ester.
11. The method of claim 8 in which the weight ratio of the safener to 6-amino-2-(substituted phenyl)-5 -substituted-4-pyrimidinecarboxylate herbicide is in the range of 1:4 to 2:1.
12. The method of claim 8 , wherein Q represents a C 2 -C 4 alkenyl.
13. The method of claim 8 , wherein Q represents a C 1 -C 4 alkoxy.
14. The method of claim 8 in which the safener is cloquintocet-mexyl.