4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides

• US 9,149,038 B2
• Filed: 03/12/2014
• Issued: 10/06/2015
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Eckelbarger, Joseph D., Epp, Jeffrey B., Fischer, Lindsey G., Lowe, Christian T., Petkus, Jeff, Roth, Joshua, Satchivi, Norbert M., Schmitzer, Paul R., Siddall, Thomas L.
• Primary Examiner(s): Pagano, Alexander R
• Application Number:
  US14/205,883
• Publication Number:
  US 20140274701A1
• Time in Patent Office: 573 Days
• Field of Search: 514/256, 514/336, 514/337, 514/339, 544/329, 546/283.7, 546/284.1, 546/277.4, 546/280.4, 546/280.7
• US Class Current: 1/1
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 411/04 directly linked by a ring-member-to-ring-member bond

Abstract

Novel 4-amino-6-(heterocyclic)picolinic acids and their derivatives and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives are useful to control undesirable vegetation.

Claims

1. A compound of the Formula (I):

2. The compound of claim 1 wherein R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy.

3. The compound of claim 2 wherein R² is Cl, methoxy, vinyl, or 1-propenyl.

4. The compound of claim 1 wherein R³ and R⁴ are both hydrogen.

5. The compound of claim 1 wherein X is N, CH, or CF.

6. The compound of claim 1 wherein R⁵ is hydrogen or halogen.

7. The compound of claim 6 wherein R⁵ is hydrogen or F.

8. The compound of claim 1 wherein R⁶ is hydrogen or F.

9. The compound of claim 1 wherein R^6′

is hydrogen.

10. The compound of claim 1 wherein:

R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy;

R³ and R⁴ are both hydrogen; and

X is N, CH, or CF.

11. The compound of claim 1 wherein:

R² is halogen, C₂-C₄-alkenyl, or C₁-C₄-alkoxy;

R³ and R⁴ are hydrogen; and

X is N, CH, or CF;

Ar is Ar7, Ar9, Ar10, Ar13, Ar15, Ar16, Ar19, Ar21, or Ar22;

R⁵ is hydrogen or F;

R⁶ is hydrogen or F;

R^6′

is hydrogen;

R⁷, R^7′

, R⁸, R^8′

, R⁹, R^9′

, R^9″

, and R<sup>9′

″</sup>

, if applicable to the relevant Ar group, are independently hydrogen or fluorine.

12. The compound of claim 1 wherein:

R² is chlorine, methoxy, vinyl, or 1-propenyl;

R³ and R⁴ are hydrogen; and

X is N, CH, or CF.

13. The compound of claim 1 wherein:

R² is chlorine;

R³ and R⁴ are hydrogen; and

X is N, CH, or CF.

14. The compound of claim 1 wherein:

R² is methoxy;

R³ and R⁴ are hydrogen; and

X is N, CH, or CF.

15. The compound of claim 1 wherein:

R² is vinyl or 1-propenyl;

R³ and R⁴ are hydrogen; and

X is N, CH, or CF.

16. A herbicidal composition comprising the compound of claim 1 and an agriculturally acceptable adjuvant or carrier.

17. The composition of claim 16, further comprising an additional herbicidal compound.

18. The composition of claim 16, further comprising a safener.

19. A method for controlling vegetation comprising applying a herbicidally effective amount of a compound of claim 1.