2-(2-fluoro-substituted phenyl)-6-amino-5-chloro-4-pyrimidinecarboxylates and their use as herbicides

1. A method of controlling undesirable vegetation in corn which comprises applying to the soil to prevent the emergence of the undesirable vegetation an herbicidally effective amount of a compound of formula I,

wherein

X represents H or halogen;

Y represents halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

Z represents H or halogen, with the proviso that at least one of X or Z is halogen and when Z is halogen then X represents H; and

R 1 and R 2 independently represent H, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, hydroxy, C 1 -C 6 alkoxy, amino, C 1 -C 6 acyl, C 1 -C 6 carboalkoxy, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl or C 1 -C 6 dialkyl phosphonyl or R 1 and R 2 taken together with N represent a 5- or 6-membered saturated ring;

and agriculturally acceptable derivatives of the carboxylic acid group.

2. The method of claim 1 , wherein the compound of formula I is:

6-amino-5-chloro-2-(4-chloro-2,3-difluorophenyl)pyrimidine-4-caroxylic acid methyl ester 6-amino-5-chloro-2-(2-fluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester;

6-amino-5-chloro-2-(2,3-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester;

6-amino-5-chloro-2-(2,3-difluoro-4-trifluoromethylphenyl)pyirimidne-4-carboxylic acid;

6-amino-5-chloro-2-(2,5-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester;

6-amino-5-chloro-2-(4,5-dichloro-2-fluorophenyl)pyrimidine-4-carboxylic acid methyl ester;

6-amino-5-chloro-2-(4-chloro-2,3-difluorophenyl)pyrimidine-4-carboxylic acid;

6-amino-5-chloro-2-(2,3-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid;

6-amino-5-chloro-2-(2,3-difluoro-4-trifluoromethylphenyl)pyrimidine-4-carboxylic acid;

6-amino-5-chloro-2-(4.5-dichloro-2-fluorophenyl)pyrimidine-4-carboxylic acid;

6-amino-5-chloro-2-(2,5-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid; or 6-amino-5-chloro-2-(4-chloro-2,5-difluorophenyl)-pyrimidine-4-carboxylic acid methyl ester.

3. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(4-chloro-2,3-difluorophenyl)pyrimidine-4-caroxylic acid methyl ester.

4. The method of claim 1 , wherein compound is 6-amino-5-chloro-2-(2-fluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester.

5. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,3-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester.

6. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,3-difluoro-4-trifluoromethylphenyl)pyirimidne-4-carboxylic acid.

7. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,5-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid methyl ester.

8. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(4,5-dichloro-2-fluorophenyl)pyrimidine-4-carboxylic acid methyl ester.

9. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(4-chloro-2,3-difluorophenyl)pyrimidine-4-carboxylic acid.

10. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,3-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid.

11. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,3-difluoro-4-trifluoromethylphenyl)pyrimidine-4-carboxylic acid.

12. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(4.5-dichloro-2-fluorophenyl)pyrimidine-4-carboxylic acid.

13. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(2,5-difluoro-4-methylphenyl)pyrimidine-4-carboxylic acid.

14. The method of claim 1 , wherein the compound is 6-amino-5-chloro-2-(4-chloro-2,5-difluorophenyl)-pyrimidine-4-carboxylic acid methyl ester.