Low volatility herbicidal compositions

• US 10,212,933 B2
• Filed: 07/19/2017
• Issued: 02/26/2019
• Est. Priority Date: 11/05/2012
• Status: Active Grant

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Hemminghaus, John W., MacInnes, Alison, Wright, Daniel R., Zhang, Junhua
• Primary Examiner(s): Pryor, Alton N
• Application Number:
  US15/653,772
• Publication Number:
  US 20170311593A1
• Time in Patent Office: 587 Days
• Field of Search: None
• 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 25/22 containing ingredients stabilising the active ingredients
• CPC Class Codes: A01N 37/02 Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 37/04 polybasic
• 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 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 57/02 having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: G09B 19/00 Teaching not covered by other main groups of this subclass teaching or practice apparatus for gun-aiming or gun-laying F41G3/26

Abstract

The present invention relates generally low volatility herbicidal compositions comprising at least one auxin herbicide and at least one monocarboxylic acid, or monocarboxylate thereof. The invention further relates generally to methods for preparing and using such low volatility herbicidal compositions, including methods for controlling auxin-susceptible plant growth on agricultural and non-agricultural lands.

Claims

1. A herbicidal composition concentrate comprising:

dicamba, or an agriculturally acceptable salt or ester thereof; and

a potassium or sodium monocarboxylate of a monocarboxylic acid;

wherein;

the concentrate comprises an amount of the potassium or sodium monocarboxylate sufficient to reduce the concentration of volatilized dicamba in the vapor phase surrounding a diluted version of the concentrate relative to the concentration of volatilized dicamba in the vapor phase surrounding an otherwise identical diluted version of the concentrate lacking the potassium or sodium monocarboxylate.

2. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises an agriculturally acceptable salt of dicamba selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.

3. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises the diglycolamine salt of dicamba.

4. The herbicidal composition concentrate of claim 1, wherein the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, and benzoic acid.

5. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises the potassium or sodium monocarboxylate salt, in whole or in part, in dissociated form, the monocarboxylate salt selected from the group consisting of formate salts, acetate salts, propionate salts, and benzoate salts of the monocarboxylic acid.

6. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises acetic acid, or an agriculturally acceptable salt thereof.

7. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises an additive selected from the group consisting of surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, antimicrobials, and/or other additives that are necessary or desirable to improve the performance, crop safety, or handling of the composition.

8. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises less than about 10 ppm of ammonium sulfate.

9. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 120 to about 600 g acid equivalent (a.e.)/L.

10. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 300 g a.e./L to about 600 g a.e./L.

11. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 350 g a.e./L to about 600 g a.e./L.

12. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 400 g a.e./L to about 600 g a.e./L.

13. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 450 g a.e./L to about 600 g a.e./L.

14. The herbicidal composition concentrate of claim 1, wherein the concentrate contains dicamba at a total loading of from about 500 g a.e./L to about 600 g a.e./L.

15. The herbicidal composition concentrate of claim 1, wherein the composition is a liquid concentrate containing a total amount (acid equivalent weight) of dicamba from about 5% to about 75% by weight of the concentrate.

16. The herbicidal composition concentrate of claim 1, wherein the composition is a liquid concentrate containing a total amount (acid equivalent weight) of dicamba from about 25% to about 35% by weight of the concentrate.

17. The herbicidal composition concentrate of claim 1, wherein the composition is a dry concentrate containing a total amount (acid equivalent weight) of dicamba from about 40% to about 90% by weight of the concentrate.

18. The herbicidal composition concentrate of claim 1, wherein the molar ratio of dicamba to the potassium or sodium monocarboxylate, is from about 1:

10 to about 10;

1.

19. The herbicidal composition concentrate of claim 1, wherein the molar ratio of dicamba to the potassium or sodium monocarboxylate, is from about 2:

1 to about 1;

2.

20. The herbicidal composition concentrate of claim 1, wherein the concentration of the potassium or sodium monocarboxylate, is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.

21. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises an amount (acid equivalent weight) of the potassium or sodium monocarboxylate, of from about 1% to about 20% by weight of the concentrate.

22. The herbicidal composition concentrate of claim 1, wherein the concentrate comprises an amount (acid equivalent weight) of the potassium or sodium monocarboxylate, of from about 2% to about 15% by weight of the concentrate.

23. The herbicidal composition concentrate of claim 1, wherein the concentrate is a liquid concentrate and comprises an amount (acid equivalent weight) of the monocarboxylate, of from about 2% to about 10% by weight of the concentrate.

24. The herbicidal composition concentrate of claim 1, wherein the concentrate is a dry concentrate and comprises an amount (acid equivalent weight) of the monocarboxylate, of from about 5% to about 15% by weight of the concentrate.

25. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof;

wherein the molar ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof, is from about 1;

10 to about 10;

1; and

/or

wherein the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof, is from about 1;

10 to about 5;

1; and

/or

wherein the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 0.25% to about 25% by weight of the concentrate; and

/or

wherein the concentration of the acetic acid, or agriculturally acceptable salt thereof, is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L; and

/or

wherein the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L.

26. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L; and

wherein the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof, is from about 1;

10 to about 5;

1.

27. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 1% to about 25% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 10% to about 60% by weight of the concentrate.

28. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 2% to about 20% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 15% to about 50% by weight of the concentrate.

29. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 3% to about 15% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 20% to about 40% by weight of the concentrate.

30. The herbicidal composition concentrate of claim 1, wherein the composition comprises:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 3% to about 10% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 25% to about 35% by weight of the concentrate.

31. The herbicidal composition concentrate of claim 1, wherein the concentrate is a dry concentrate comprising:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 1% to about 40% by weight of the concentrate;

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 40% to about 90% by weight of the concentrate; and

wherein the sum of the acetic acid weight percent and the dicamba weight percent is less than or equal to 100%.

32. The herbicidal composition concentrate of claim 1, wherein the concentrate is a dry concentrate comprising:

acetic acid, or an agriculturally acceptable salt thereof;

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 3% to about 30% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 50% to about 80% by weight of the concentrate; and

wherein the sum of the acetic acid weight percent and the dicamba weight percent is less than or equal to 100%.

33. The herbicidal composition concentrate of claim 1, wherein the concentrate is a dry concentrate comprising:

acetic acid, or an agriculturally acceptable salt thereof; and

wherein;

the concentrate contains an amount (acid equivalent weight) of the acetic acid, or agriculturally acceptable salt thereof, from about 5% to about 20% by weight of the concentrate; and

the concentrate contains an amount (acid equivalent weight) of dicamba, or an agriculturally acceptable salt or ester thereof, from about 60% to about 75% by weight of the concentrate.

34. A herbicidal composition concentrate comprising:

(a) dicamba, or an agriculturally acceptable salt or ester thereof;

(b) at least one monocarboxylic acid; and

(c) a neutralizing base, wherein the neutralizing base is an alkali metal hydroxide selected from potassium hydroxide, sodium hydroxide, or a mixture thereof, wherein;

the concentrate comprises an amount of the monocarboxylic acid and neutralizing base sufficient to reduce the concentration of volatilized dicamba in the vapor phase surrounding a diluted version of the concentrate relative to the concentration of volatilized dicamba in the vapor phase surrounding an otherwise identical diluted version of the concentrate lacking the monocarboxylic acid, and neutralizing base.

35. A herbicidal composition comprising:

(a) dicamba or an agriculturally acceptable salt or ester thereof;

(b) at least one monocarboxylic acid, or a monocarboxylate thereof;

(c) a neutralizing base, wherein the neutralizing base is an alkali metal hydroxide selected from potassium hydroxide, sodium hydroxide, or a mixture thereof; and

(d) water;

wherein;

the composition comprises an amount of the monocarboxylic acid and neutralizing base, or an amount of the monocarboxylate, sufficient to reduce the concentration of volatilized dicamba in the vapor phase surrounding the composition relative to the concentration of volatilized dicamba in the vapor phase surrounding an otherwise identical composition lacking the monocarboxylic acid and neutralizing base, or monocarboxylate.

36. The herbicidal composition of claim 35, wherein the herbicidal composition is prepared by a process comprising:

mixing the dicamba, or agriculturally acceptable salt or ester thereof, the monocarboxylic acid, and a neutralizing base comprising an alkali metal hydroxide selected from potassium hydroxide, sodium hydroxide, or a mixture thereof, thereby forming a liquid concentrate comprising the dicamba, or agriculturally salt or ester thereof, and the monocarboxylate.

37. The herbicidal composition of claim 35, wherein the herbicidal composition is prepared by a process comprising:

mixing the dicamba, or agriculturally acceptable salt or ester thereof, with the monocarboxylate, thereby forming a liquid concentrate comprising the dicamba, or agriculturally acceptable salt or ester thereof, and the monocarboxylate.

38. The herbicidal composition of claim 35, wherein:

the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to dicamba, or an agriculturally acceptable salt or ester thereof, is from about 1;

10 to about 10;

1; and

/or

the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to dicamba, or an agriculturally acceptable salt or ester thereof, is from about 1;

10 to about 5;

1; and

/or

the composition comprises an amount (acid equivalent weight) of the monocarboxylic acid, or monocarboxylate thereof, from about 0.01% to about 25% by weight of the composition; and

/or

the concentration of the monocarboxylic acid, or monocarboxylate thereof, is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.

39. The herbicidal composition of claim 35, wherein the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, is from about 0.1 grams (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L.

40. The herbicidal composition of claim 35, wherein the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, is from about 10 grams (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L.

41. The herbicidal composition of claim 35, wherein the composition comprises an amount (acid equivalent weight) of the monocarboxylic acid, or monocarboxylate thereof, from about 0.05% to about 5% by weight of the composition.

42. The herbicidal composition of claim 35, wherein the neutralizing base is potassium hydroxide.

43. The herbicidal composition of claim 35, wherein the neutralizing base is sodium hydroxide.

44. The herbicidal composition of claim 35, comprising the neutralizing base and monocarboxylic acid at a molar ratio of about 50:

50 (1;

1) or about 60;

40 (1.5;

1).

45. The herbicidal composition of claim 35, wherein the composition has a pH equal to or higher than the acid dissociation constant (pKa) of the monocarboxylic acid present in the composition.