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

• US 9,611,282 B2
• Filed: 11/13/2014
• Issued: 04/04/2017
• 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., Fields, Stephen Craig, Fischer, Lindsey G., Giampietro, Natalie C., Guenthenspberger, Katherine A., Lowe, Christian T., Petkus, Jeff, Roth, Joshua, Satchivi, Norbert M., Schmitzer, Paul R., Siddall, Thomas L., Wang, Nick X.
• Primary Examiner(s): Haghighatian, Mina
• Assistant Examiner(s): HIRT, ERIN E
• Application Number:
  US14/540,679
• Publication Number:
  US 20150126372A1
• Time in Patent Office: 873 Days
• Field of Search: None
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/52 condensed with carbocyclic rings, e.g. benzimidazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/647 Triazoles; Hydrogenated triazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• 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 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• 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 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07F 7/0803 Compounds with Si-C or Si-Si linkages

Abstract

4-Amino-6-(heterocyclic)picolinic acids and their derivatives; 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.

Claims

1. A compound of the Formula (I):

2. The compound of claim 1, wherein

R¹ is OR^1′

, wherein R^1′

is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³ and R⁴ taken together represent ═

CR^3′

(R^4′

), wherein R^3′

and R^4′

are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino;

A is A3, A7, A8, A9, A10, A11, A12, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶, R^6′

, and R^6″

are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^7′

are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl, amino or C₁-C₄ alkylamino;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

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

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

5. The compound of claim 1, wherein R³ and R⁴ are hydrogen.

6. The compound of claim 1, wherein A is A3, A7, A8, A9, A10, or A15.

7. The compound of claim 6, wherein A is A3 or A15.

8. The compound of claim 7, wherein A is A15.

9. The compound of claim 1, wherein R⁵ is hydrogen or F.

10. The compound of claim 9, wherein R⁵ is F.

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

12. The compound of claim 1, wherein R^6″

is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

13. The compound of claim 1, wherein R⁶, R^6′

, and R^6″

are all hydrogen.

14. The compound of claim 1, wherein A is A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36.

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

16. A method of controlling undesirable vegetation which comprises applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation a compound of claim 1.

17. A method of controlling undesirable vegetation which comprises applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation a herbicidal composition of claim 15.