Compositions and methods related to half salts of herbicidal carboxylic acids

• US 10,526,271 B2
• Filed: 03/09/2017
• Issued: 01/07/2020
• Est. Priority Date: 12/14/2015
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Liu, Lei, Tank, Holger, Olds, Melissa Gail, Wilson, Stephen L.
• Primary Examiner(s): Shin, Monica A
• Application Number:
  US15/378,659
• Publication Number:
  US 20170210691A1
• Time in Patent Office: 1,034 Days
• Field of Search: None
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: C07C 59/31 containing rings
• CPC Class Codes: C07D 213/64 attached in position 2 or 6

Abstract

Half salts of certain synthetic auxin herbicides are provided. These half salts are useful for controlling unwanted plant growth. The half salts have low solubility in water, low volatility relative to commercial compositions of the corresponding synthetic auxin herbicides, and offer comparable herbicidal performance when compared to existing salts of the synthetic auxin herbicides.

Claims

1. A half salt of a synthetic auxin herbicide that has the formula

2. The half salt of claim 1, wherein the monovalent metal cation is selected from the group consisting of lithium, sodium, and potassium.

3. The half salt of claim 1, wherein the tetrasubstituted ammonium ion is selected from the group consisting of tetramethyl ammonium, tetraethyl ammonium and choline.

4. The half salt of claim 1, wherein the synthetic auxin herbicide is selected from the group consisting of 2,4-D, 2,4-DB, triclopyr, fluroxypyr, MCPA, MCPB, mecoprop, and mecoprop-P.

5. The half salt of claim 4 wherein the synthetic auxin herbicide is 2,4-D and M is sodium.

6. The half salt of claim 4 wherein the auxin herbicide is 2,4-D and M is potassium.

7. The half salt of claim 4 wherein the auxin herbicide is 2,4-D and M is lithium.

8. The half salt of claim 4 wherein the auxin herbicide is 2,4-D and M is choline.

9. The half salt of claim 4 wherein the auxin herbicide is triclopyr and M is sodium.

10. The half salt of claim 4 wherein the auxin herbicide is triclopyr and M is potassium.

11. The half salt of claim 4 wherein the auxin herbicide is triclopyr and M is lithium.

12. The half salt of claim 4 wherein the auxin herbicide is triclopyr and M is choline.

13. The half salt of claim 4 wherein the auxin herbicide is fluroxypyr and M is sodium.

14. The half salt of claim 4 wherein the auxin herbicide is fluroxypyr and M is potassium.

15. The half salt of claim 4 wherein the auxin herbicide is fluroxypyr and M is lithium.

16. The half salt of claim 4 wherein the auxin herbicide is fluroxypyr and M is choline.

17. A herbicidal composition comprising the half salt of claim 1.

18. The herbicidal composition of claim 17, further comprising one or more agriculturally acceptable adjuvants or carriers.

19. The herbicidal composition of claim 17, wherein the composition is a liquid concentrate or a dry concentrate.

20. The herbicidal composition of claim 19, wherein the liquid concentrate is a suspension concentrate.

21. The herbicidal composition of claim 19, wherein the dry concentrate is selected from the group consisting of a powder, a granule, and a dispersible granule.

22. The herbicidal composition of claim 17, wherein the composition is an aqueous spray solution or mixture.

23. The herbicidal composition of claim 17 further comprising a second herbicide.

24. The herbicidal composition of claim 23, wherein the second herbicide is selected from the group consisting of glyphosate, glufosinate, and salts thereof.

25. The composition of claim 17, wherein the synthetic auxin comprises the sodium half salt of 2,4-D and a salt of glyphosate.

26. The composition of claim 17, wherein the synthetic auxin comprises the potassium half salt of 2,4-D and a salt of glyphosate.

27. The composition of claim 17, wherein the synthetic auxin comprises the lithium half salt of 2,4-D and a salt of glyphosate.

28. The composition of claim 17, wherein the synthetic auxin comprises the choline half salt of 2,4-D and a salt of glyphosate.

29. The composition of claim 17, wherein the synthetic auxin comprises the sodium half salt of 2,4-D and a salt of glufosinate.

30. The composition of claim 17, wherein the synthetic auxin comprises the potassium half salt of 2,4-D and a salt of glufosinate.

31. The composition of claim 17, wherein the synthetic auxin comprises the lithium half salt of 2,4-D and a salt of glufosinate.

32. The composition of claim 17, wherein the synthetic auxin comprises the choline half salt of 2,4-D and a salt of glufosinate.

33. The composition of claim 25, wherein the salt of glyphosate is selected from the group consisting of the isopropyl ammonium salt, the dimethyl ammonium salt, and the potassium salt.

34. The composition of claim 26, wherein the salt of glyphosate is selected from the group consisting of the isopropyl ammonium salt, the dimethyl ammonium salt, and the potassium salt.

35. The composition of claim 27, wherein the salt of glyphosate is selected from the group consisting of the isopropyl ammonium salt, the dimethyl ammonium salt, and the potassium salt.

36. The composition of claim 28, wherein the salt of glyphosate is selected from the group consisting of the isopropyl ammonium salt, the dimethyl ammonium salt, and the potassium salt.

37. The composition of claim 29, wherein the salt of glufosinate is the ammonium salt.

38. The composition of claim 30, wherein the salt of glufosinate is the ammonium salt.

39. The composition of claim 31, wherein the salt of glufosinate is the ammonium salt.

40. The composition of claim 32, wherein the salt of glufosinate is the ammonium salt.

41. A method of preparing the half salt of claim 1 comprising:

a) combining;

i) a solution consisting essentially of a first solvent and a synthetic auxin herbicide of formula

42. The method of claim 41, wherein the synthetic auxin herbicide is selected from the group consisting of 2,4-D, 2,4-DB, triclopyr, fluroxypyr, MCPA, MCPB, mecoprop, and mecoprop-P.

43. A method of controlling undesirable vegetation comprising contacting the vegetation or a locus thereof with, or applying to soil to prevent the emergence of vegetation, a herbicidally effective amount of the herbicidal composition of claim 17.