Pesticide concentrates containing etheramine surfactants

• US 20030096708A1
• Filed: 11/19/2001
• Published: 05/22/2003
• Est. Priority Date: 03/02/2001
• Status: Abandoned Application

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Seifert-Higgins, Simone, Agbaje, Henry E., Becher, David Z., Brinker, Ronald J., Bates, Chris
• Application Number:
  US09/988,340
• Publication Number:
  US 20030096708A1
• Time in Patent Office: Days
• US Class Current: 504/365
• 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 25/30 characterised by the surfactants
• CPC Class Codes: A01N 37/04 polybasic
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• 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

Diamines or other polyamines increase the compatibility of ether amine surfactants with pesticide formulations such as those containing glyphosate or a salt or ester thereof.

Claims

1. A cationic surfactant composition for use in an aqueous pesticidal formulation comprising a first surfactant selected from the group consisting of:

(a) dialkoxylated amines or quaternary ammonium salts having the formulae;

wherein R¹ and R⁴ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, -R⁵SR⁶, or -(R²O)_zR³,R² in each of the x (R²O), y (R²O) and z (R²O) groups is independently C₂-C₄ alkylene, R³ is hydrogen, or a linear or branched alkyl group having from 1 to about 22 carbon atoms, R⁵ is a linear or branched alkyl group having from about 6 to about 30 carbon atoms, R⁶ is a linear or branched alkyl group having from about 4 to about 15 carbon atoms, x, y and z are independently an average number from 1 to about 40, and X- is an agriculturally acceptable anion.;

(b) aminated alkoxylated alcohol having the formula;

wherein R¹ is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms;

R² in each of the x (R²O) and y (R²O) groups is independently C₂-C₄ alkylene;

R³ and R⁶ are each independently hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms;

R⁴ is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy substituted hydrocarbyl, -(R⁶)_n-(R²O)_yR⁷, —

C(=NR¹¹)NR¹²R¹³, —

C(=O)NR¹²R¹³, or —

C(=S)NR¹²R¹³;

R⁵ is -(R⁶)_n-(R²O)_yR⁷;

R⁷ is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms;

R¹¹, R¹² and R¹³ are hydrogen, hydrocarbyl or substituted hydrocarbyl, R¹⁴ is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy substituted hydrocarbyl, -(R⁶)_n-(R²O)_yR⁷, —

C(=NR¹¹)NR¹²R¹³, —

C(=O)NR¹²R¹³, or —

C(=S)NR¹²R ¹³, n is 0 or 1, x and y are independently an average number from 1 to about 60, and A- is an agriculturally acceptable anion;

(c) etheramines or ether quaternary ammonium salts having the formula;

wherein R¹ is hydrogen or a hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms;

R² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms;

R³, R⁴ and R⁵ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R⁶O)_xR⁷, R⁶ in each of the x(R⁶O) groups is independently C₂-C₄ alkylene, R⁷ is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, x is an average number from 1 to about 50, and A- is an agriculturally acceptable anion;

(d) alkoxylated poly(hydroxyaikyl)amines having the formula;

wherein R¹ and R³ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R² in each of the x (R²O) groups is independently C₂-C₄ alkylene;

R⁴ is hydrocarbylene or substituted hydrocarbylene having from 1 to about 30 carbon atoms, R⁵ is hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl;

x is an average number from 0 to about 30, and y is 0or 1;

(e) monoalkoxylated amines having the formula;

wherein R¹ and R⁴ are independently hydrocarbyl or substituted hydrocarbyl groups having from 1 to about 30 carbon atoms or -R⁵SR⁶, R² in each of the x (R²O) groups is independently C₂-C₄ alkylene, R³ is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R⁵ is a linear or branched alkyl group having from about 6 to about 30 carbon atoms, R⁶ is a hydrocarbyl or substituted hydrocarbyl group having from 4 to about 15 carbon atoms and x is an average number from 1 to about 60;

(f) monoalkoxylated quatemary ammonium salts having the formula;

wherein R¹ and R⁵ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R⁴ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R² in each of the x (R²O) groups is independently C₂-C₄ alkylene, R³ is hydrogen, or a linear or branched alkyl group having from 1 to about 30 carbon atoms, x is an average number from 1 to about 60, and X- is an agriculturally acceptable anion; and

(g) an amine having the formula;

wherein R¹ and R⁹ are independently hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R²O)_pR¹³;

R² in each of the m (R²O), n (R²O), p (R²O) and q (R²O) groups is independently C₂-C₄ alkylene;

R³, R⁸, R¹³ R¹⁵ are independently hydrogen, or a hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms;

R⁴ is —

(CH₂)_yOR¹³ or —

(CH₂)_yO(R²O)_qR³;

R⁵, R⁶ and R⁷ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or R⁴;

R¹⁴ is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —

(CH₂)_zO(R²O)_pR³;

m, n, p and q are independently an average number from 1 to about 50;

X is —

O—

, —

N(R¹⁴)—

, —

C(O)—

, —

C(O)O—

, —

OC(O)—

, —

N(R¹⁵)C(O)—

, —

C(O)N(R¹⁵)—

, —

S—

, —

SO—

, or —

SO₂—

;

t is 0 or 1;

A- is an agriculturally acceptable anion; and

y and z are independently an integer from 0 to about 30; and

a second surfactant selected from the group consisting of;

(a) alkoxylated diamines having the formula;

wherein R¹ is hydrocarbyl or substituted hydrocarbyl having from about 8 to about 30 carbon atoms;

R² in each of the x (R²O) groups and the y (R²O) groups is independently C₂-C₄ alkylene;

R³, R⁵ and R⁶ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R²O)_yR⁷;

R⁴ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms, —

C(=NR¹¹)NR¹²R¹³—

, —

C(=O)NR ¹²R¹³—

, —

C(=S)NR¹²R¹³—

, —

C(=NR¹²)—

, —

C(S)—

, or —

C(O)—

;

R⁷ is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms;

R¹¹, R¹² and R¹³ are hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, x is 0 or an average number from 1 to about 30; and

y is an average number from 1 to about 50;

(b) diamines having the formula;

wherein R¹, R³, R⁴ and R⁵ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R⁶O)_xR⁷;

R² and R⁸ are independently hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, R⁶ in each of the x (R⁶O) and y (R⁶O) groups is independently C₂-C₄ alkylene, R⁷ is hydrogen, or a linear or branched alkyl group having from 1 to about 30 carbon atoms, x is an average number from 1 to about 30, X is —

O—

, —

N(R⁶)—

, —

C(O)—

, —

C(O)O—

, —

OC(O)—

, —

N(R⁹)C(O)—

, —

C(O)N(R⁹)—

, —

S—

, —

SO—

, or —

SO₂—

, y is 0 or an average number from 1 to about 30, n and z are independently 0 or 1, and R⁹ is hydrogen or hydrocarbyl or substituted hydrocarbyl;

(c) diamines having the formula;

wherein R¹, R³, R⁴ and R⁵ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R⁶O)_xR⁷, R² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, R⁶ in each of the x (R⁶O) and y (R⁶O) groups is independently C₂-C₄ alkylene, R⁷ is hydrogen, or a linear or branched alkyl group having from 1 to about 30 carbon atoms, x is an average number from 1 to about 30, and y is an average number from about 3 to about 60;

(d) diamines having the formula;

wherein R¹, R² and R⁵ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms or -R⁸(OR⁹)_nOR¹⁰, R³ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R⁸ and R⁹ are individually hydrocarbylene or substituted hydrocarbylene having from 2 to about 4 carbon atoms, R⁴ and R¹⁰ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an average number from 0 to about 40, X is —

C(O)—

or —

SO₂—

, and A- is an agriculturally acceptable anion;

(e) diamines having the formula;

wherein R¹, R⁴, R⁵ and R⁶ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R² in each of the m (R²O) and n (R²O) groups and R⁷ are independently C₂-C₄ alkylene, R³ is hydrocarbylene or substituted hydrocarbylene having from about 2 to about 6 carbon atoms or -(R²O)_pR⁷-, m and n are individually an average number from 0 to about 50, and p is an average number from 0 to about 60;

(f) di-poly(hydroxyalkyl)amines having the formula;

wherein R¹ and R³ are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R⁴ and R⁵ are independently hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl; and

(g) alkoxylated triamines having the formula;

wherein R¹ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms;

R², R³, R⁴ and R⁵ are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or -(R⁸)_s(R⁷O)_nR⁶;

R⁶ is hydrogen or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R⁷ in each of the n (R⁷O) groups is independently C₂-C₄ alkylene;

R⁸ is hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms, n is an average number from 1 to about 10, s is 0 or 1, and x and y are independently an integer from1 to about 4.

2. A surfactant composition of claim 1 wherein said surfactant of formula (d) is a monoalkoxylated amine or quaternary amine having the formulae:

3. A pesticidal composition comprising

(a) at least one pesticide;

and

(b) an agriculturally useful amount of the surfactant composition of claim 1.

4. A composition of claim 3 wherein the pesticide comprises a herbicide.

5. A composition of claim 4 wherein the herbicide comprises glyphosate or a salt or ester thereof.

6. A composition of claim 5 wherein the glyphosate is predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, isopropylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsuffonium salt thereof.

7. A composition of claim 6 wherein the glyphosate is predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsulfonium salt thereof.

8. A composition of claim 1 wherein said composition is a concentrate.

9. An aqueous herbicidal composition comprising:

(a) glyphosate or a salt or ester thereof; and

(b) an agriculturally useful amount of the surfactant composition of claim 1.

10. A composition of claim 1 wherein said composition is a concentrate.

11. An aqueous herbicidal composition comprising

(a) glyphosate, predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine ortrimethylsulfonium salt thereof;

and

(b) an agriculturally useful amount of the surfactant composition of claim 1.

12. A composition of claim 11 wherein said composition is a concentrate.

13. A composition of claim 11 wherein the glyphosate is predominantly in the form of the potassium salt.

14. An aqueous herbicidal concentrate composition comprising:

glyphosate predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsulfonium salt thereof, in solution in an aqueous medium in an amount of in excess of 300 grams acid equivalent per liter of the composition; and

from about 20 to about 300 grams per liter of the surfactant composition of claim 1.

15. The composition of claim 14 wherein the surfactant component is in a stable emulsion.

16. The composition of claim 14 wherein the surfactant component is in a stable suspension.

17. The composition of claim 14 wherein the surfactant component is in a stable dispersion.

18. The composition of claim 14 wherein the surfactant component is in a solution.

19. The composition of claim 14 wherein the composition is stable after storage at 50°

C. for at least 14 days.

20. The composition of claim 14 wherein the composition is stable after storage at 50°

C. for about 28 days.

21. The composition of claim 14 wherein said surfactant component is selected such that the composition has a cloud point not lower than about 50°

C.

22. The composition of claim 14 wherein the composition has a viscosity of less than about 1000 centipoise at 0°

C. at 45/s shear rate.

23. The composition of claim 22 wherein the composition has a viscosity of less than about 700 centipoise at 0°

C. at 45/s shear rate.

24. The composition of claim 23 wherein the composition has a viscosity of less than about 400 centipoise at 0°

C. at 45/s shear rate.

25. The composition of claim 24 wherein the composition has a viscosity of less than about 225 centipoise at 0°

C. at 45/s shear rate.

26. The composition of claim 14 wherein said surfactant composition is selected such that the herbicidal concentrate composition exhibits no crystallization of said glyphosate or salt thereof when stored at a temperature of about 0°

C. for a period of about 7 days.

27. The composition of claim 26 wherein said surfactant composition is selected such that the herbicidal concentrate composition exhibits no crystallization of said glyphosate or salt thereof when stored at a temperature of about −

10°

C. for a period of about 7 days.

28. The composition of claim 14 wherein said glyphosate, predominantly in the form of the potassium salt thereof, is in solution in said medium in an amount of about 310 to about 600 grams of acid equivalent per liter of the composition.

29. The composition of claim 28 wherein said glyphosate, predominantly in the form of the potassium salt thereof, is in solution in said medium in an amount of about 360 to about 600 grams of acid equivalent per liter of the composition.

30. The composition of claim 29 wherein said glyphosate, predominantly in the form of the potassium salt thereof, is in solution in said medium in an amount of about 400 to about 600 grams of acid equivalent per liter of the composition.

31. The composition of claim 30 wherein the concentration of said glyphosate is from about 450 to about 600 grams of acid equivalent per liter of the composition.

32. The composition of claim 30 wherein the concentration of said glyphosate is from about 500 to about 600 grams of acid equivalent per liter of the composition.

33. The composition of claim 31 wherein the concentration of said glyphosate is from about 480 to about 600 grams of acid equivalent per liter of the composition.

34. The composition of claim 30 wherein the concentration of said glyphosate is from about 480 to about 580 grams of acid equivalent per liter of the composition.

35. The composition of claim 31 wherein the concentration of said glyphosate is from about 540 to about 600 grams of acid equivalent per liter of the composition.

36. The composition of claim 14 wherein the total amount of surfactant is from about 60 to about 240 grams per liter of the herbicidal concentrate composition.

37. The composition of claim 36 wherein the total amount of surfactant is from about 60 to about 200 grams per liter of the herbicidal concentrate composition.

38. The composition of claim 14 wherein the composition is substantially homogeneous upon storage at 50°

C. for one week.

39. A composition of claim 14 wherein the composition has a density of at least about 1.210 grams/liter.

40. A composition of claim 14 wherein the surfactant composition comprised by the herbicidal concentrate composition is not substantially antagonistic to the herbicidal activity of the glyphosate.

42. A pesticidal composition comprising

(a) at least one pesticide;

and

(b) an agriculturally useful amount of the surfactant composition of claim 1.

43. A composition of claim 42 wherein the pesticide comprises a herbicide.

44. A composition of claim 43 wherein the herbicide comprises glyphosate or a salt or ester thereof.

45. A composition of claim 44 wherein the glyphosate is predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, isopropylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsulfonium salt thereof.

46. A composition of claim 45 wherein the glyphosate is predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsulfonium salt thereof.

52. A herbicidal method comprising diluting in a suitable volume of water a herbicidally effective amount of a composition of claim 14 to form an application mixture, and applying the application mixture to foliage of a plant.

53. A herbicidal method comprising mixing a surfactant composition of claim 1 with a herbicide to form a herbicidal composition, diluting in a suitable volume of water a herbicidally effective amount of the herbicidal composition to form an application mixture, and applying the application mixture to foliage of a plant or plants.

41. A cationic surfactant composition for use in an aqueous pesticidal formulation comprising at least one etheramine having the formula:

47. A composition of claim 41 wherein said composition is a concentrate.

48. An aqueous herbicidal composition comprising:

glyphosate or a salt or ester thereof; and

an agriculturally useful amount of the surfactant composition of claim 41.

49. A composition of claim 41 wherein said composition is a concentrate.

50. An aqueous herbicidal composition comprising

glyphosate, predominantly in the form of the potassium, monoammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine or trimethylsulfonium salt thereof;

and

an agriculturally useful amount of the surfactant composition of claim 41.

51. A composition of claim 50 wherein said composition is a concentrate.

54. A herbicidal method comprising diluting in a suitable volume of water a herbicidally effective amount of a composition of claim 49 to form an application mixture, and applying the application mixture to foliage of a plant.

55. A herbicidal method comprising mixing a surfactant composition of claim 41 with a herbicide to form a herbicidal composition, diluting in a suitable volume of water a herbicidally effective amount of the herbicidal composition to form an application mixture, and applying the application mixture to foliage of a plant or plants.