Microemulsion coformulation of a graminicide and a water-soluble herbicide

• US 6,369,001 B1
• Filed: 08/04/2000
• Issued: 04/09/2002
• Est. Priority Date: 08/11/1999
• Status: Expired due to Term

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Jimoh, Ganiyu A.
• Primary Examiner(s): CLARDY, S
• Application Number:
  US09/633,193
• Time in Patent Office: 613 Days
• Field of Search: 504/128, 504/363, 504/118
• US Class Current: 504/118
• 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 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals

Abstract

A liquid concentrate herbicidal microemulsion composition is provided comprising

(i) water;

(ii) a water-soluble herbicide;

(iii) an oil-soluble cyclohexenone or aryloxyphenoxypropionate graminicide in a weight ratio to the water-soluble herbicide of about 1:50 to about 1:1;

(iv) a substantially water-immiscible organic solvent selected such that the graminicide has an organic solvent/water partition coefficient, expressed as a logarithm, of about 4 or greater, in a weight ratio to the graminicide of about 3:1 to about 30:1;

(v) an emulsifying system comprising one or more surfactants each having a tertiary amine functional group, in an amount not exceeding about 10% by weight but sufficient to provide acceptable physical stability of the microemulsion;

(vi) zero to a stabilizing amount of one or more water-soluble chlorides selected from hydrochloric acid, alkali metal chlorides, ammonium chloride, low molecular weight organic ammonium chlorides and quaternary ammonium chloride surfactants; and

(vii) a dispersing system comprising one or more nonionic surfactants, in a total amount not exceeding about 5% by weight but sufficient to provide acceptable dispersion of the microemulsion upon dilution thereof in a suitable volume of water for application to plants and not sufficient to destabilize the microemulsion.

Compositions of the invention wherein the water-soluble herbicide is a salt of glyphosate are particularly useful for controlling unwanted glyphosate-tolerant plants of the grass family in glyphosate-tolerant broadleaf crops.

Claims

1. A liquid concentrate herbicidal microemulsion composition having a continuous aqueous phase and a discontinuous oil phease, comprising

(i) water in said aqueous phase;

(ii) a water-soluble herbicide dissolved in said water in an amount which is biologically effective when the compositioin is diluted in a suitable volunme of water and applied to foliage of a susceptible plant;

(iii) an oil-soluble graminicide in said oil phase having the chemical formula (I)

 

where R¹ is a butyryl, (2-ethylthio)propyl or 2,4,6-trimethylphenyl group or a group

 

wherein X is O or S;

R² is a C_1-4 alkyl group; and

R³ is an ethyl, allyl or 3- haloallyl group;

or the chemical formula (II)

 

where R⁴ is a group

 

wherein R⁶ and R⁷ are independently selected from hydrogen, halogen, methyl, trifluoromethyl and cyano groups, and Y and Z are independently selected from CH and N, at least one of Y and Z being N; and

R⁵ is a hydrogen, C_1-4 alkyl, allyl, propargyl, tetrahydrofurfuryl, 2-ethoxyethyl or 2-isopropylideneaminooxyethyl group;

said graminicide being present in a weight ratio to said water-soluble herbicide of about 1;

50 to about 1;

1;

(iv) a substantially water-immiscible organic solvent in said oil phase selected such that said graminicide has an organic solvent/water partition coefficient, expressed as a logarithm, of about 4 or greater, said organic solvent being present in a weight ratio to said graminicide of about 3;

1 to about 30;

1;

(v) an emulsifying system comprising one or more surfactants each having a tertiary amine functional group, in an amount not exceeding about 10% by weight of the composition but sufficient to provide acceptable physical stability of the microemulsion;

(vi) a stabilizing amount of one or more water-solublc chlorides selected from hydrochloric acid, alkali metal chlorides, ammonium chloride, low molecular weight organic ammonium chlorides and quaternary ammonium chloride surfactants; and

(vii) a dispersing system comprising one or more nonionic surfactants, in a total amount not exceeding about 5% by weight but sufficient to provide acceptable dispersion of the microemulsion upon dilution thereof in a suitable volume of water for application to plants and not sufficient to destabilize the microemulsion.

2. A composition of claim 1 that contains about 5% to about 50% by weight in total of the water-soluble herbicide and the graminicide.

3. A composition of claim 1 that contains about 20% to about 50% by weight in total of the water-soluble herbicide and the graminicide.

4. A composition of claim 1 wherein the water-soluble herbicide is selected from acifluorfen, acrolein, amitrole, asulam, benazolin, bentazon, bialaphos, bromacil, bromoxynil, chloramben, chloroacetic acid, clopyralid, 2,4-D, 2,4-DB, dalapon, dicamba, dichlorprop, difenzoquat, diquat, endothall, fenac, fenoxaprop, flamprop, flumiclorac, fluoroglycofen, flupropanate, fomesafen, fosamine, glufosinate, glyphosate, imazameth, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, mecoprop, methylarsonic acid, naptalam, nonanoic acid, paraquat, picloram, quinclorac, sulfamic acid, 2,3,6-TBA, TCA, triclopyr and water-soluble salts thereof.

5. A composition of claim 1 wherein the water-soluble herbicide is a salt of glyphosate.

6. A composition of claim 5 wherein the salt of glyphosate is selected from the alkali metal, ammonium, C_1-6 alkylammonium, C_1-6 alkanolammonium and C_1-6 alkylsulfonium salts.

7. A composition of claim 1 wherein the graminicide is selected from butroxydim, clethodim, cycloxydim, sethoxydim, tepraloxydim, haloxyfop, propaquizafop and the C_4-1 alkyl and propargyl esters of clodinafop, cyhalofop, diclofop, fluazifop, fluazifop-P, quizalofop and quizalofop-P.

8. A composition of claim 1 wherein the water-soluble herbicide is a salt of glyphosate and the graminicide is quizalofop-P-ethyl.

9. A composition of claim 1 wherein the organic solvent is selected such that said graminicide has an organic solvent/water partition coefficient, expressed as a logarithm, of about 5 or greater.

10. A composition of claim 1 wherein the organic solvent is an aromatic solvent.

11. A composition of claim 1 wherein the organic solvent is present in a weight ratio to said graminicide of about 4:

1 to about 10;

1.

12. A composition of claim 1 wherein the amount of all surfactants in the composition is less than about 12% by weight.

13. A composition of claim 1 wherein the emulsifying system comprises one or more surfactants selected from polyoxyethylene (2-20) tertiary alkylamines and polyoxyethylene (2-20) tertiary alkyletheramines.

14. A composition of claim 13 wherein said alkylamines and alkyletheramines have alkyl chains having about 12 to about 18 carbon atoms.

15. A composition of claim 13 wherein the amount of said alkylamine and/or alkyletheramine surfactants is about 3% to about 10% by weight.

16. A composition of claim 13 wherein the amount of said alkylamine and/or alkyletheramine surfactants is about 3% to about 6% by weight.

17. A composition of claim 1 wherein a water-soluble quaternary ammonium chloride surfactant is present at about 1% to about 6% by weight.

18. A composition of claim 17 wherein said quaternary ammonium chloride surfactant is benzalkonium chloride.

19. A composition of claim 1 wherein one or more chlorides selected from low molecular weight organic ammonium chlorides, ammonium chloride, alkali metal chlorides and hydrochloric acid are present in an amount providing about 0.5% to about 2.5% chloride ion by weight.

20. A composition of claim 19 wherein the chlorides are one or both of ammonium chloride and hydrochloric acid.

21. A composition of claim 1 wherein the dispersing system comprises one or more nonionic surfactants selected from polyoxyethylene (2-20) alkylethers and alkylphenylethers.

22. A composition of claim 21 wherein the amount of said nonionic surfactants is about 1% to about 3% by weight.

23. A composition of claim 1 wherein the aqueous phase has a pH in a range that is minimally conducive to chemical degradation of the graminicide.

24. A process for killing or controlling unwanted plants, comprising diluting a composition of claim 1 in a suitable volume of water to form a plant treatment composition, and applying the plant treatment composition to foliage of the unwanted plants.

25. A process of claim 24 wherein the unwanted plants comprise descendants of crop plants of the grass family genetically transformed to tolerate the water-soluble herbicide present in the composition, and said unwanted plants are growing in a broadleaf crop genetically transformed to tolerate said water-soluble herbicide.

26. A process of claim 25 wherein the water-soluble herbicide present in the composition is glyphosate, said descendants of crop plants of the grass family are selected from glyphosate-tolerant corn, rice and wheat and said broadleaf crop is selected from glyphosate-tolerant cotton, soybeans, rapeseed, canola and sugar beet.