Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts

• US 20090305896A1
• Filed: 03/30/2007
• Published: 12/10/2009
• Est. Priority Date: 12/06/2006
• Status: Active Grant

• Current Assignee: Akzo Nobel Chemicals International B.V. (Nouryon Coöperatief UA)
• Original Assignee: Akzo Nobel N.V. (Nouryon BV)
• Inventors: Sun, Jinxia Susan, Khan, Shuaib A., Zhu, Shawn
• Granted Patent: US 9,012,365 B2
• Time in Patent Office: Days
• US Class Current: 504/323
• 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 33/02 Amines; Quaternary ammonium compounds
• 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
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: C05G 3/60 Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants

Abstract

The present invention generally relates to a method for minimizing the formation of insoluble salts of phenoxy herbicides. The method comprises (1) mixing a compatibility agent, amine salts of phenoxy acid herbicides, and a chemical containing non-amine cations in a aqueous system to form a stable and non-nozzle plugging solution; and (2) application of said stable and non-nozzle plugging solution onto target plants.

Claims

1. A herbicidal formulation with improved compatibility in the presence of non-amine cations, said formulation comprising at least one amine salt of a phenoxy acid herbicide, and a compatibility agent in an amount effective to prevent the formation of insoluble salts of said phenoxy acid herbicide, wherein said compatibility agent comprises at least one surfactant.

2. The formulation of claim 1 wherein said phenoxy acid herbicide is a phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 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, and combinations thereof.

3. The formulation of claim 1 wherein said surfactant compatibility agent comprises a surfactant selected from alkoxylated quaternary surfactant, alkyl quaternary surfactant, alkoxylated amine, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil alkoxylate, inorganic base or combinations thereof, with the proviso that when glyphosate is present the inorganic base is excluded.

4. The formulation of claim 3 wherein said surfactant compatibility agent is

i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms;

R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and

A is C_iH_2i where i is 2 to 4;

B is C_jH_2j where j is 2 to 6; and

X⁻

is a compatible anion such as methyl sulfate or chloride, f is zero to 10;

m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p may be greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms. R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms. A is C_iH_2i where i is 2 to 4;

B is C_jH_2j where j is 2 to 6; and

X⁻

is a compatible anion such as methyl sulfate or chloride;

f is zero to 10;

p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a provision that p may be greater than q. In one embodiment, the A is C2H₄, f=0, and g=0;

iii. an alkoxylated amine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms;

A is C_iH_2i where i is 2 to 4; and

B is C_jH_2j where j is 2 to 6. f is zero to 10;

m and n is an integer of from 0-30 with the proviso that m+n is at least 1, p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p;

iv. an amidoamine of the formula;

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

v. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

A is C_iH_2i where i is 2 to 4;

n, m, p, and q all is 1 to 20 independently;

x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1;

vi. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms;

A is C_iH_2i where i is 2 to 4;

m is 1 to 30, and n is 1 to 30;

vii. tristyrylphenol ethoxylate with 8-30 EO and its phosphate or salts thereof;

viii. EO/PO block and random copolymer of the formula,

R1

OA′

)_xH

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′

is C2 or C3, x is 30 to 300, EO;

PO>

40;

60 (weight ratio).

ix. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

x. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

xi. Hydroxides of sodium, potassium, ammonium and mixtures thereof with the proviso that if glyphosate is present these hydroxides of sodium, potassium, and ammonium are excluded;

or

xii. mixtures thereof.

5. The formulation of claim 4 wherein said surfactant compatibility agent is selected from the group consisting essentially of tallowamine 2-15EO methylchloride quaternary, cocoamine 2-15EO methylchloride quaternary, cocotrimethyl quaternary ammonium chloride, cocoamine ethoxylate 2-20EO, tallowamine ethoxylate 2-20EO, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tall oil and diethylenetriamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyryrphenol+13-20EO, C4 with average 52EO and 42PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulfonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate-36 EO, coco duoamine-3EO, and mixtures and combinations thereof.

6. The formulation of claim 1 wherein the ratio of said at least one amine salt of a phenoxy acid herbicide, and said compatibility agent is from 20:

1 to 1;

2.

7. The formulation of claim 4 wherein the phenoxy acid herbicide is 2,4-D.

8. The formulation of claim 7 wherein the ratio of 2,4-D amine salt to the surfactant is from −

10;

1 to 1;

1.5.

9. The formulation of claim 7 wherein the ratio of 2,4-D amine salt to the surfactant is from 5:

1 to 1;

1.

10. The formulation of claim 7 wherein the concentration of 2,4-D amine salt is from 0.1 to 40.

11. The formulation of claim 7 wherein the concentration of 2,4-D amine salt is from 1 to 30% by weight.

12. The formulation of claim 7 wherein the concentration of 2,4-D amine salt is from −

2 to 20% by weight.

21. The formulation of claim 4 wherein in formula i), A is C2H₄, f=0, g=0, m+n is 2 to 20, R2 is methyl group, p=1, and X is chloride.

22. The formulation of claim 4 wherein in formula II) A is C2H₄, f=0, g=0, R2 is methyl group, R3 is a methyl group, R4 is a methyl group, p=1, and X is chloride.

23. The formulation of claim 4 wherein in formula iii) A is C2H₄, f=0, g=0, m+n is 1 to 20, p=1.

24. The formulation of claim 4 wherein in formula v), R1 is derived from tall oil, coconut oil, soya oil, corn, and/or tallow.

13. A method for improving the compatibility of herbicidal formulations comprising amine salts of phenoxy acid herbicides when said formulations come into contact with non-amine cations, said method comprising adding to said herbicidal formulation at least one compatibility agent in a sufficient amount to improve the compatibility of said formulation.

14. The method of claim 13 wherein said herbicide is selected from a phenoxy acid herbicide of phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 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, and mixtures thereof.

15. The method of claim 13 wherein said compatibility agent comprises at least one alkoxylate quaternary surfactant, alkyl quaternary surfactant, alkoxylated amine, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil ethoxylate, inorganic base or combinations thereof, with the proviso that when glyphosate is present the inorganic base is excluded.

16. The method of claim 15 wherein said compatibility agent is

i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms;

R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and

A is C_iH_2i where i is 2 to 4;

B is C_jH_2j where j is 2 to 6; and

X⁻

is a compatible anion such as methyl sulfate or chloride, f is zero to 10;

m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p may be greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms. R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms. A is C_iH_2i where i is 2 to 4;

B is C_jH_2j where j is 2 to 6; and

X⁻

is a compatible anion such as methyl sulfate or chloride. f is zero to 10;

p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p may be greater than q;

iii. an alkoxylated amine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms;

A is C_iH_2i where i is 2 to 4; and

B is C_jH_2j j where j is 2 to 6. f is zero to 10;

m and n is an integer of from 0-30 with the proviso that m+n is at least 1, p is 1 to 7 and g can be any number from zero to 6 for each p and independent of p;

iv. an amidoamine of the formula;

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

v. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

A is C_iH_2i where i is 2 to 4;

n, m, p, and q all are 1 to 20 independently;

x and y is 0 to 5 independently with a proviso that x+y are greater than or equal to 1;

vi. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms;

A is C_iH_2i where i is 2 to 4;

m is 1 to 30, and n is 1 to 30;

vii. tristyrylphenol ethoxylate with 8-30 moles ethoxylation and its phosphate or salts thereof;

viii. EO/PO block and/or random copolymer of the formula,

R1

OA′

)_xH

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′

is C2 or C3, x is 30 to 300, EO;

PO>

40;

60 (weight ratio);

ix. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

x. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

xi. Hydroxides of sodium, potassium, ammonium and mixtures thereof with a proviso that if glyphosate is present these hydroxides of sodium, potassium, and ammonium are excluded;

or

xii. mixtures thereof.

17. The method of claim 16 wherein said compatibility agent is selected from the group consisting essentially of tallowamine 2-15EO methyl chloride quaternary, cocoamine 2-15 EO methylchloride quaternary, coco trimethyl quaternary ammonium chloride cocoamine ethoxylate 2-20EO, tallowamine ethoxylate 2-20EO, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyrylphenol+13-20EO, C4 with average of 52EO and 46PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulphonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate 36EO, coco duoamine-3EO, and mixtures and combinations thereof.

18. The method of claim 13 wherein the phenoxy acid herbicide is 2,4-D.

19. The method of claim 18 wherein the ratio of 2,4-D amine salt to the surfactant is from 10:

1 to 1;

1.5.

20. The method of claim 18 wherein the concentration of 2,4-D amine salt is from 0.1 to 40% by weight.