3-alkoxy, thioalkyl and amino-4-amino-6-(substituted)picolinates and their use as herbicides

• US 8,754,229 B2
• Filed: 06/29/2012
• Issued: 06/17/2014
• Est. Priority Date: 06/30/2011
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Epp, Jeffrey B., Lowe, Christian T., Renga, James M., Schmitzer, Paul R., Eckelbarger, Joseph D., Guenthenspberger, Katherine A., Siddall, Thomas L., Yerkes, Carla N., Kister, Jeremy, Roth, Joshua, Fischer, Lindsey Gayle, Giampietro, Natalie Christine
• Primary Examiner(s): REESE, HEIDI L
• Application Number:
  US13/538,399
• Publication Number:
  US 20130005574A1
• Time in Patent Office: 718 Days
• Field of Search: None
• US Class Current: 546/290
• CPC Class Codes: A01N 43/40 six-membered rings
• 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 213/65 attached in position 3 or 5
• CPC Class Codes: C07D 213/73 Unsubstituted amino or imino radicals
• CPC Class Codes: C07D 213/79 Acids; Esters
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07F 7/0803 Compounds with Si-C or Si-Si linkages
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring

Abstract

3-alkoxy, thioalkyl and amino-4-amino-6-(substituted)picolinic acids having a halogen, alkyl or mono-, di- tri- and tetra-substituted aryl substituents in the 6-position, and their acid derivatives, are herbicides demonstrating a broad spectrum of weed control.

Claims

1. A compound of the Formula A:

2. The compound of claim 1, wherein Q is C₁-C₄ alkoxy or C₁-C₄ haloalkoxy.

3. The compound of claim 1, wherein Q is SR³ or NR₁R_2.

4. The compound of claim 1, wherein Q is C₁-C₄ alkoxy.

5. The compound of claim 1, wherein Q is methoxy.

6. The compound of claim 1, wherein X is H or F.

7. The compound of claim 1, wherein Y is Ar.

8. The compound of claim 1, wherein Ar is para-substituted phenyl with or without other substituents.

9. The compound of claim 8, wherein the para-substituted phenyl has no other substitutents.

10. The compound of claim 8, wherein the para-substituted phenyl has one or two other substitutents.

11. The compound of claim 8, wherein the para-substituted phenyl has three or four other substitutents.

12. The compound of claim 8, wherein the other substituents is each independently halogen or C_1-6 alkoxy.

13. The compound of claim 1, wherein:

a. Q is methoxy,

b. X is H or F,

c. Y is para-substitued phenyl with or without other substituents, and

d. R¹ and R² independently represent H.

14. The compound of claim 1, wherein the compound is the compound of formula A or, with respect to the carboxylic acid moiety of Formula A, a C₁-C₆ alkyl ester or benzyl ester thereof.

16. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 1 and an agriculturally acceptable adjuvant or carrier.

17. A method of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof with, or applying to soil or water to prevent the emergence of vegetation, an herbicidally effective amount of a compound of claim 1.

15. A compound selected from the following: