Alkylamidopropyl dialkylamine surfactants as adjuvants

• US 20100056375A1
• Filed: 12/03/2007
• Published: 03/04/2010
• Est. Priority Date: 12/06/2006
• Status: Active Grant

• Current Assignee: Nouryon Chemicals International B.V. (Nouryon BV)
• Original Assignee: Akzo Nobel N.V. (Nouryon BV)
• Inventors: Jönsson, Claes Johan Markus, Zhu, Shawn
• Granted Patent: US 8,293,683 B2
• Time in Patent Office: Days
• US Class Current: 504/142
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• 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 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Abstract

The present invention generally relates to an aqueous herbicidal formulation that comprises at least one phenoxy acid herbicide or an agriculturally acceptable salt or derivative thereof, and an alkylamidopropyl dialkylamine surfactant adjuvant, wherein said surfactant adjuvant comprises at least one surfactant having the formula (I) wherein R is a straight or branched chain, saturated or unsaturated acyl group having 6-22 carbon atoms, n is 3, and Y and Y′ are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10; provided that at least one of the groups Y and Y′ is an alkyl group having 1-4 carbon atoms; or a salt thereof; or a quaternised derivative of (I) having the formula (II) wherein R is a straight or branched chain, saturated or unsaturated acyl group having from 6 to 22 carbon atoms; n is 3; Y and Y′ are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10; provided that at least one of the groups Y and Y′ is an alkyl group having 1-4 carbon atoms; R2 is a C1-C4 alkyl group; and X⁻ is an anion. The invention also relates to a method for combating unwanted vegetation which comprises applying to said unwanted vegetation an effective amount of the aforementioned herbicidal formulation.

Claims

1. An aqueous herbicidal composition comprising at least one phenoxy acid herbicide or an agriculturally acceptable salt or derivative thereof, and a surfactant adjuvant, wherein said surfactant adjuvant comprises at least one alkylamidopropyl dialkylamine surfactant having the formula

wherein R is—

a straight or branched chain, saturated or unsaturated acyl group having 6-22 carbon atoms, n is 3, and Y and Y′

are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10;

provided that at least one of the groups Y and Y′

is an alkyl group having 1-4 carbon atoms;

or a salt thereof;

or a quaternised derivative of (I) having the formula

wherein R is a straight or branched chain, saturated or unsaturated acyl group having from 6 to 22 carbon atoms;

n is 3;

Y and Y′

are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10;

provided that at least one of the groups Y and Y′

is an alkyl group having 1-4 carbon atoms;

R2 is a C1-C4 alkyl group; and

X⁻

is an anion.

2. The composition of claim 1 wherein R is a straight or branched chain, saturated or unsaturated acyl group having from 6 to 18 carbon atoms;

at least one of Y and Y′

is a C₁-C₄ alkyl group, and n is 3.

3. The composition of claim 2 wherein R is a straight or branched chain, saturated or unsaturated alkyl group having from 6 to 14 carbon atoms;

Y and Y′

are methyl, and n is 3.

4. The composition of claim 2 wherein R is a straight or branched chain, saturated or unsaturated alkyl group having from 6 to 10 carbon atoms.

5. The composition of claim 1 wherein said R is derived from a natural fatty acid.

6. The composition of claim 1 wherein said R group is derived from coco.

7. The composition of claim 1 wherein said R group is an acyl group having 8 to 10 carbon atoms.

8. The composition of claim 1 wherein said alkylamidopropyl dialkylamine surfactant is selected from the group consisting of N-[3-(dimethylamino)propyl] (C₈-C₁₀) amide, N-[3-(dimethylamino)propyl]cocoamide, and N-[3-(dimethylamino)propyl] (rape-seed) amide.

9. A herbicidal composition according to claim 1 wherein the phenoxy acid herbicide is a phenoxyacetic acid herbicide, phenoxybutyric acid herbicide, phenoxypropionic acid herbicide, aryloxyphenoxypropionic acid herbicide, or a mixture thereof.

10. A herbicidal composition according to claim 1 wherein the phenoxy acid herbicide is selected from the group consisting of 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, 2,4,5-T, 2,4,5-TB, and mixtures thereof.

11. The composition of claim 10 wherein said phenoxy acid herbicide is a water-soluble 2,4 D salt.

12. The composition of claim 11 wherein the concentration of phenoxy acid is in the range of 100-800 g ae/l, and the ratio of phenoxy acid (wt % ae) to the surfactant adjuvant of formula I is between 1:

2 and 25;

1.

13. The composition of claim 12 wherein the concentration of phenoxy acid is in the range of 400-700 g ae/l, and the ratio of phenoxy acid (wt % ae) to the surfactant adjuvant of formula I is between 2.5:

1 and 20;

1.

14. The composition of claim 13 wherein the ratio of phenoxy acid (wt % ae) to the surfactant adjuvant of formula I is between 3:

1 and 15;

1.

15. The composition of claim 1 further comprising at least one co-herbicide.

16. The composition of claim 1 wherein said composition does not contain any water-insoluble solvent or water-insoluble oil.

17. The composition of claim 1 further comprising an alkaline compound other than the compound of formula (I).

18. The composition of claim 17 where the alkaline compound is selected from the group consisting of dimethylamine, isopropylamine, triethylamine and diethanolamine.

19. The composition of claim 1 wherein said composition is an aqueous concentrate, wherein said aqueous concentrate contains phenoxy acid equivalent in the range of from 20 to 40%, and from about 2 to about 20% alkylamidopropyl dialkylamine surfactant.

21. A method of controlling unwanted vegetation, said method comprising applying to said unwanted vegetation an effective amount of a herbicidal composition according to claim 1.

22. The method of claim 21 wherein said herbicidal composition comprises the phenoxy acid herbicide 2,4 D.

20. A method of making an aqueous herbicidal composition comprising mixing at least one phenoxy acid herbicide or an agriculturally acceptable salt or derivative thereof with a surfactant adjuvant, wherein the surfactant adjuvant comprises at least one alkylamidopropyl dialkylamine surfactant having the formula

wherein R is a straight or branched chain, saturated or unsaturated acyl group having 6-22 carbon atoms, n is 3, and Y and Y′

are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10;

provided that at least one of the groups Y and Y′

is an alkyl group having 1-4 carbon atoms;

or a salt thereof;

or a quaternised derivative of (I) having the formula

wherein R is a straight or branched chain, saturated or unsaturated acyl group having from 6 to 22 carbon atoms;

n is 3;

Y and Y′

are, independently, an alkyl group having 1-4 carbon atoms or (AO)_sH, wherein AO is an alkyleneoxy group having 2-4 carbon atoms, and s is on average 1-10;

provided that at least one of the groups Y and Y′

is an alkyl group having 1-4 carbon atoms;

R2 is a C1-C4 alkyl group; and

X⁻

is an anion.