Safening 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide injury on cereal crops

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;

and its agriculturally acceptable salt, ester and amide derivatives,

which comprises, in addition to the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide, a safener selected from the group consisting of fenchlorazole, fenchlorazole-ethty, mefenpyr, mefenpyr-diethyl, and mixtures thereof,

wherein the weight ratio of the safener to 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is between 1:16 and 4:1.

2. 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.

3. The composition of claim 1 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is selected from the group consisting of 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl pyrimidine-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; 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; and agriculturally acceptable salts, esters, or amides thereof.

4. The composition of claim 1 , wherein Q represents a C 2 -C 4 alkenyl.

5. The composition of claim 4 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.

6. The composition of claim 1 , wherein Q represents a C 1 -C 4 alkoxy.

7. The composition of claim 6 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid methyl ester.

8. The composition of claim 1 in which the safener is fenchlorazole-ethyl.

9. The composition of claim 1 in which the safener is mefenpyr-diethyl.

10. A method of protecting a 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, C1-C4 alkyl or C1-C4 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 selected from fenchlorazole, fenchlorazole-ethyl, mefenpyr, mefenpyr-diethyl, and mixtures thereof,

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.

11. The method of claim 10 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 10 in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is selected from the group consisting of 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl pyrimidine-4-carboxylic acid; 6-amino-2-(4-trifluoromethyl phenyl)-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; 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-methoxypyrimidine-4-carboxylic acid; and agriculturally acceptable salts, esters, or amides thereof.

13. The method of claim 10 , wherein Q represents a C 2 -C 4 alkenyl.

14. The method of claim 13 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.

15. The method of claim 10 , wherein Q represents a C 1 -C 4 alkoxy.

16. The method of claim 15 , in which the 6-amino-2-(substituted phenyl)-5-substituted-4-pyrimidinecarboxylate herbicide is 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylic acid methyl ester.

17. The method of claim 10 in which the safener is mefenpyr-diethyl.

18. The method of claim 10 in which the safener is fenchlorazole-ethyl.