Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use

• US 20030144147A1
• Filed: 03/21/2002
• Published: 07/31/2003
• Est. Priority Date: 09/26/2001
• Status: Active Grant

• Current Assignee: Platte Chemical Company
• Original Assignee: Platte Chemical Company
• Inventors: Herold, Anthony E., Parrish, Scott K., Beardmore, Richard A.
• Granted Patent: US 6,703,346 B2
• Time in Patent Office: Days
• US Class Current: 504/275
• CPC Class Codes: A01N 2300/00 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 Class Codes: A01N 25/02 containing liquids as carriers, diluents or solvents
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• CPC Class Codes: A01N 37/38 having at least one oxygen or sulfur atom attached to an aromatic ring system
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• 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 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: A01N 59/02 Sulfur; Selenium; Tellurium; Compounds thereof
• CPC Class Codes: A01N 59/20 Copper
• CPC Class Codes: A01N 59/26 Phosphorus; Compounds thereof
• CPC Class Codes: A01N 61/00 Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

Abstract

Described are herbicide compositions (including suspension concentrates, herbicide compositions prepared therefrom), and others that include imidazolinone acid, which can optionally and preferably also include an acidifying agent, and methods of making and using such compositions.

Claims

1. A herbicide composition comprising

a suspension concentrate comprising an imidazolinone acid, and

acidifying agent other than sulfuric acid in an amount so the pH of the composition is below the pKa of the imidazolinone acid.

2. The composition of claim 1 wherein the pH of the composition is below about 4.0.

3. The composition of claim 1 comprising an acidifying agent selected from the group consisting of:

hydrochloric acid, nitric acid, acetic acid, phosphoric acid, perchloric acid, polyphosphoric acid, and combinations thereof.

4. The composition of claim 3 wherein the composition does not include sulfuric acid.

5. The composition of claim 3 wherein the composition does not include sulfuric acid adduct of the formula:

6. The composition of claim 1 wherein the acidifying agent comprises sulfuric acid adduct of the formula:

7. The composition of claim 6 wherein the adduct is an adduct of sulfuric acid and urea.

8. The composition of claim 1 wherein the imidazolinone acid is chosen from the group consisting of imazethapyr acid, imazaquin acid, imazapyr acid, imazamethabenz acid, imazapic acid, imazamox acid, and combinations thereof.

9. The composition of claim 1 wherein the suspension concentrate comprises surfactant selected from nonionic surfactant, anionic surfactant, cationic surfactant, and mixtures thereof.

10. The composition of claim 1 comprising alcohol alkoxylate nonionic surfactant having the formula

R—

O—

((CH₂)_xO)_y—

H

wherein R is a branched or linear alkyl, x is in the range from 2 to 5, and y is in the range from 5 to 25.

11. The composition of claim 10 wherein R is a short chain branched or linear alcohol having from about 3 to 23 or fewer carbon atoms.

12. The composition of claim 1 comprising linear alcohol ethoxylate nonionic surfactant of the formula:

CH₃(C₂H₄)_mO(C₂H₄O)_nH

wherein m is in the range from 1 to 11 and n is in the range from about 5 to 25.

13. The composition of claim 1 comprising linear alcohol propoxylate nonionic surfactant of the formula:

CH₃(C₂H₄)_mO(C₃H₆O)_nH,

wherein m is in the range from 1 to 11 carbon atoms and n is in the range from about 5 to 25.

14. The composition of claim 1 comprising anionic surfactant selected from the group consisting of sodium alkyl naphthalene sulfonate, sodium butyl naphthalene sulfonate, sodium di-n-butyl naphthalene sulfonate, sodium diisopropyl naphthalene sulfonate, sodium dimethyl naphthalene sulfonate, ethoxylated tristyrylphenol phosphate potassium salt, and mixtures thereof.

42. The herbicide composition of claim 1 comprising additional active herbicide compound.

43. The herbicide composition of claim 42 wherein the additional active herbicide compound is a herbicide compound in acid form.

44. The herbicide composition of claim 43 wherein the additional herbicide compound in acid form is glyphosate acid.

15. A herbicide composition comprising

imidazolinone acid, and

acidifying agent other than sulfuric acid in an amount so the pH of the composition is below the pKa of the imidazolinone acid.

45. The herbicide composition of claim 15 comprising additional active herbicide compound.

46. The herbicide composition of claim 45 wherein the additional active herbicide compound is an acid form of active herbicide compound.

47. The herbicide composition of claim 46 wherein the additional active herbicide compound is glyphosate acid.

16. A suspension concentrate comprising imidazolinone acid and a short chain alcohol ethoxylate nonionic surfactant having a short chain branched or linear alkyl having from 3 to 23 or fewer carbon atoms.

17. The suspension concentrate of claim 16 wherein the nonionic surfactant comprises short chain linear alcohol ethoxylate surfactant.

18. The suspension concentrate of claim 16 wherein the nonionic surfactant has the formula:

CH₃(C₂H₄)_mO(C₂H₄O)_nH

wherein m is in the range from 1 to 11 and n is in the range from about 5 to 25.

19. The suspension concentrate of claim 16 comprising from greater than 30 to about 50 parts by weight imidazolinone acid per 1 part by weight surfactant.

20. The suspension concentrate of claim 16 wherein the suspension concentrate is an aqueous suspension concentrate.

21. The suspension concentrate of claim 20 containing essentially no organic solvent.

22. The suspension concentrate of claim 16 wherein the imidazolinone acid is selected from the group consisting of imazethapyr acid, imazaquin acid, imazapyr acid, imazamethabenz acid, imazapic acid, imazamox acid, and combinations thereof.

48. A herbicide composition comprising suspension concentrate of claim 16 and acidifying agent.

23. A suspension concentrate comprising an imidazolinone acid and anionic surfactant.

24. The suspension concentrate of claim 23 wherein the suspension concentrate is an aqueous suspension concentrate.

25. The suspension concentrate of claim 23 wherein the anionic surfactant comprises a sodium alkyl naphthalene sulfonate surfactant.

26. The suspension concentrate of claim 25 wherein the anionic surfactant is selected from the group consisting of sodium butyl naphthalene sulfonate, sodium di-n-butyl naphthalene sulfonate, sodium diisopropyl naphthalene sulfonate, sodium dimethyl naphthalene sulfonate, and mixtures thereof.

27. The suspension concentrate of claim 23 wherein the anionic surfactant comprises an ethoxylated tristyrylphenol phosphate salt.

28. The suspension concentrate of claim 27 wherein the anionic surfactant comprises ethoxylated tristyrylphenol phosphate potassium salt.

49. A herbicide composition comprising suspension concentrate of claim 23 and acidifying agent.

29. A suspension concentrate comprising imidazolinone acid and surfactant, comprising from greater than 30 parts by weight imidazolinone acid to about 50 parts by weight imidazolinone acid, per 1 part by weight surfactant.

30. The suspension concentrate of claim 29 wherein the suspension concentrate is an aqueous suspension concentrate.

31. The suspension concentrate of claim 29 comprising from 31 to 45 parts by weight imidazolinone acid per 1 part by weight surfactant.

32. The composition of claim 29 further comprising from about 2 to about 5 weight percent dispersant.

33. A herbicide composition comprising:

aqueous suspension concentrate comprising

about 25 to about 45 weight percent imidazolinone acid, and

about 0.5 to about 1.5 weight percent surfactant selected from the group consisting of;

short chain alcohol ethoxylate nonionic surfactant, anionic surfactant, cationic surfactant, and mixtures thereof, and

about 40 to about 60 parts by weight water; and

acidifying agent selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, acetic acid, phosphoric acid, perchloric acid, polyphosphoric acid, an adduct of sulfuric acid and urea, and combinations thereof, in an amount so the pH of the composition is below the pKa of the imidazolinone acid.

34. A herbicide composition comprising:

aqueous suspension concentrate comprising

about 25 to about 45 weight percent imidazolinone acid, and

about 0.5 to about 1.5 weight percent surfactant selected from the group consisting of;

nonionic surfactant, anionic surfactant, cationic surfactant, and mixtures thereof, and

about 40 to about 60 parts by weight water; and

acidifying agent selected from the group consisting of hydrochloric acid, nitric acid, acetic acid, phosphoric acid, perchloric acid, and polyphosphoric acid, an adduct of sulfuric acid and urea, and combinations thereof, in an amount so the pH of the composition is below the pKa of the imidazolinone acid.

35. A method of killing or controlling unwanted vegetation growth, the method comprising

preparing a herbicide composition comprising an imidazolinone acid and an amount of acidifying agent other than sulfuric acid to reduce the pH of the herbicide composition to a pH below the pKa of the imidazolinone acid, and

applying the herbicide composition to control plant growth.

36. A method of killing or controlling unwanted vegetation growth, the method comprising

preparing a herbicide composition comprising a suspension concentrate comprising an imidazolinone acid and surfactant selected from the group consisting of short chain alcohol ethoxylate nonionic surfactant, anionic surfactant, cationic surfactant, and mixtures thereof, and

applying the herbicide composition to control plant growth.

37. The method of claim 36 wherein the herbicide composition comprises acidifying agent to reduce the pH of the herbicide composition to below the pKa of the imidazolinone acid, the acidifying agent selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, acetic acid, phosphoric acid, perchloric acid, and polyphosphoric acid, and a sulfuric acid adduct of the formula:

38. The method of claim 37 wherein the acidifying agent is selected from the group consisting of phosphoric acid, polyphosphoric acid, and an adduct of urea and sulfuric acid.

39. A method of preparing a herbicide composition comprising imidazolinone acid, the method comprising

combining imidazolinone acid particles with water and surfactant,

mixing or agitating the water, imidazolinone acid particles, and surfactant,

wet milling water, imidazolinone acid particles, and surfactant to produce a suspension concentrate, and

combining the suspension concentrate with acidifying agent in an amount to produce a herbicide composition having a pH below the pKa of the imidazolinone acid.

40. A method of preparing a suspension concentrate, the method comprising

combining imidazolinone particles with surfactant and water, the surfactant comprising a surfactant selected from the group consisting of:

a short chain alcohol ethoxylate nonionic surfactant, anionic surfactant, cationic surfactant, and mixtures thereof,

mixing the water, imidazolinone particles, and surfactant, and

wet milling the mixture to produce a suspension concentrate.

41. The method of claim 40 wherein the suspension concentrate is an aqueous suspension concentrate.