Alkoxylated asymmetric alkylamine surfactants as adjuvants
View Patent ↗The present invention generally relates to a herbicidal formulation that comprises 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 alkoxylated asymmetric alkylamine surfactant having the formula (I) wherein R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group having from 8 to 24 carbon atoms; R2 is a C1-C4 alkyl group or a benzyl group; A is an alkylene group containing from 2-4 carbon atoms; x is 1-30; and y is 0-10; or a quaternised derivative of (I) having the formula (II) wherein R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group having from 8 to 24 carbon atoms; R2 is a C1-C4 alkyl group or a benzyl group; A is an alkylene group containing from 2-4 carbon atoms; x is 1-30; y is 0-10; R3 is a C1-C4 alkyl group; and Y − is an anion. The invention also relates to a method for controlling unwanted vegetation which comprises applying an effective amount of the aforementioned herbicidal formulation to said unwanted vegetation.
1. A 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 alkoxylated asymmetric alkylamine surfactant of the formula
wherein R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group having from 8 to 24 carbon atoms; R2 is a C 1-4 alkyl group or a benzyl group; A is an alkylene group containing from 2-4 carbon atoms; x is 1-30; and y is 0-10; or a salt thereof.
2. The composition of claim 1 wherein R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group having from 10 to 18 carbon atoms; A is an alkylene group containing from 2-4 carbon atoms; x is 1-20; and y is 0-5.
3. The composition of claim 2 wherein R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group having from 12 to 18 carbon atoms; A is an alkylene group containing from 2-3 carbon atoms; x is 1-10; and y is 0-3.
4. The composition of claim 1 wherein said R1 is derived from a natural fatty acid.
5. The composition of claim 1 wherein said R1 group is derived from tallow.
6. The composition of claim 1 wherein said alkoxylated asymmetric alkylamine surfactant is selected from the group consisting of (tallow alkyl)methylamine with 2 to 40 EO; (coco alkyl)methylamine with about 2 to 40 EO; C 12 methylamine with about 2 to 40 EO, 2-propylheptyl methylamine with 3 to 20 EO, compounds of formula I wherein R1 is methyl-branched C 13 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 5-20, and compounds of formula I wherein R1 is C 11 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 5-20.
7. The herbicidal composition of 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.
8. The herbicidal composition of claim 1 where the phenoxy acid herbicide is selected from the group consisting of 4-CPA (4-chlorophenoxyacetic acid), 2,4-D ((2,4-dichlorophenoxy)acetic acid), 3,4-DA ((3,4-dichlorophenoxy)acetic acid), MCPA ((4-chloro-2-methylphenoxy)acetic acid, MCPA-thioethyl, 4-CPB (4-chlorophenoxybutyric acid), 2,4-DB ((2,4-dichlorophenoxy)butyric acid, 3,4-DB ((3,4-dichlorophenoxy)butyric acid), MCPB ((4-chloro-2-methylphenoxy)butyric acid), cloprop, 4-CPP (4-chlorophenoxypropionic acid), dichlorprop dichlorprop-P, 3,4-DP (3,4-dichlorophenoxypropionic acid), 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, and mixtures thereof.
9. The composition of claim 8 wherein said phenoxy acid herbicide is a water-soluble 2,4 D salt.
10. The composition of claim 9 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 from about 1:2 to about 25:1.
11. The composition of claim 10 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 from about 2.5:1 to about 20:1.
12. The composition of claim 11 wherein the ratio of phenoxy acid (wt % ae) to the surfactant adjuvant of formula I is from about 3:1 to about 15:1.
13. The composition of claim 1 which additionally comprises at least one co-herbicide.
14. The composition of claim 1 wherein said composition does not contain any water-insoluble solvent or water-insoluble oil.
15. The composition of claim 1 further comprising an alkaline compound other than the compound of formula (I).
16. The composition of claim 15 wherein the alkaline compound is selected from the group consisting of dimethylamine, isopropylamine, triethylamine and diethanolamine.
17. The composition of claim 1 wherein said composition is a solid phenoxy acid salt formulation.
18. The composition of claim 1 wherein said composition is an aqueous concentrate, wherein said aqueous concentrate contains a phenoxy acid equivalent in the range of from 20 to 40%, and from about 2 to about 20% of alkoxylated asymmetric alkylamine surfactant.
19. A method of controlling unwanted vegetation, said method comprising applying an effective amount of the herbicidal composition of claim 1 to said unwanted vegetation.
20. The method of claim 19 wherein said herbicidal composition comprises the phenoxy acid herbicide 2,4 D.
21. The composition of claim 1 wherein said alkoxylated asymmetric alkylamine surfactant is selected from the group consisting of (tallow alkyl)methylamine with, 5 to 20 EO; (coco alkyl)methylamine with about 2 to 25 EO; C 12 methylamine with about 2 to 25 EO, 2-propylheptyl methylamine with 4 to 15 EO, compounds of formula I wherein R1 is methyl-branched C 13 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15, and compounds of formula I wherein R1 is C 11 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15.
22. The composition of claim 1 wherein said alkoxylated asymmetric alkylamine surfactant is selected from the group consisting of (tallow alkyl)methylamine with 7 to 12 EO; (coco alkyl)methylamine with about 2 to 15 EO; C 12 methylamine with about 2 to 15 EO, 2-propylheptyl methylamine with 4 to 15 EO, compounds of formula I wherein R1 is methyl-branched C 13 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15, and compounds of formula I wherein R1 is C 11 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15.
23. The composition of claim 1 wherein said alkoxylated asymmetric alkylamine surfactant is selected from the group consisting of (tallow alkyl)methylamine with 7 to 12 EO; (coco alkyl)methylamine with about 2 to 10 EO; C 12 methylamine with about 2 to 10 EO, 2-propylheptyl methylamine with 5 to 10 EO, compounds of formula I wherein R1 is methyl-branched C 13 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15, and compounds of formula I wherein R1 is C 11 -alkyl, R2 is methyl, y is 2, 3, 4 or 5, and x is 10-15.