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

Patent metadata

Field	Value
Publication number	US-9408387-B2
Application number	US-91387910-A
Country	US
Kind code	B2
Filing date	Oct 28, 2010
Priority date	Oct 29, 2009
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Satchivi Norbert M
• Schmitzer Paul R
• Dow Agrosciences Llc

Inventors

• Satchivi Norbert M
• Schmitzer Paul R

Classifications

• A01N43/54 Primary

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title