Encapsulation of herbicides to reduce crop injury

Patent metadata

Field	Value
Publication number	US-12239130-B2
Application number	US-202017067977-A
Country	US
Kind code	B2
Filing date	Oct 12, 2020
Priority date	Feb 13, 2009
Publication date	Mar 4, 2025
Grant date	Mar 4, 2025

Abstract

Methods of reducing injury to crop foliage and achieving weed control using encapsulated acetamide herbicides are described. Herbicidal microcapsules comprising herbicide core material and a shell wall encapsulating the core material are also described. The microcapsules provide reduced crop injury through controlled herbicide release.

First claim

What is claimed is:

1. An herbicidal composition comprising:
microcapsules dispersed in an aqueous liquid, the microcapsules comprising a shell wall comprising a polyurea and containing a water-immiscible core material comprising an acetamide herbicide, wherein the acetamide herbicide comprises acetochlor,
wherein the shell wall is formed in a polymerization medium by a polymerization reaction between a polyisocyanate component comprising a mixture of aliphatic polyisocyanates and a polyamine component comprising a polyamine or mixture of polyamines to form the polyurea and
wherein the microcapsules have a mean particle size range of from about 9 μm to about 12 μm, the composition further comprising:
a thickener selected from the group consisting of guar- or xanthan-based gums, cellulose ethers, modified cellulosics and polymers, and microcrystalline cellulose anti-packing agents; and
urea; and wherein:
the core material further comprises from about 1% to about 10% by weight of a water-insoluble paraffinic hydrocarbon organic solvent selected from linear or branched hydrocarbons;
the mixture of aliphatic polyisocyanates comprises:
a cycloaliphatic diisocyanate of structure (IX):

 and
an aliphatic triisocyanate of structure (X):

 and
the polyamine or the mixture of polyamines comprises triethylene tetramine.

2. The herbicidal composition of claim 1 wherein the microcapsules have a mean particle size range of from about 9 μm to about 11 μm.

3. The herbicidal composition of claim 1 wherein the ratio of amine molar equivalents contained in the polyamine component to isocyanate molar equivalents contained in the polyisocyanate component is from 1.1:1 to about 1.7:1.

4. The herbicidal composition of claim 1 wherein the weight to weight ratio of acetamide herbicide to the shell wall is from about 10:1 to about 6:1.

5. The herbicidal composition of claim 1 wherein the polyisocyanate component has a minimum average of 2.5 reactive groups per polyisocyanate molecule and the polyamine component has an average of at least three reactive groups per polyamine molecule.

6. The herbicidal composition of claim 1 wherein the ratio of the aliphatic triisocyanate of structure (X) to the cycloaliphatic diisocyanate of structure (IX), on an isocyanate equivalent basis, is between about 90:10 and about 30:70.

7. The herbicidal composition of claim 1 wherein the core material comprises the water-insoluble paraffinic hydrocarbon solvent at a weight ratio of the acetamide herbicide to the solvent of from 15 to 1.

8. The herbicidal composition of claim 1 wherein the amine molar equivalents contained in the polyamine component is in excess to the isocyanate molar equivalents contained in the polyisocyanate component.

9. An herbicidal composition comprising:
microcapsules dispersed in an aqueous liquid, the microcapsules comprising a shell wall comprising a polyurea and containing a water-immiscible core material comprising an acetamide herbicide, wherein the acetamide herbicide comprises acetochlor,
wherein the shell wall is formed in a polymerization medium by a polymerization reaction between a polyisocyanate component comprising a mixture of polyisocyanates and a polyamine component comprising a polyamine or mixture of polyamines to form the polyurea, and
wherein the microcapsules have a mean particle size range of from about 8 μm to about 12 μm, where the polyisocyanate component is more than 50% by weight of a trimer of 1,6-hexamethylene diisocyanate, and
wherein the polyamine or the mixture of polyamines comprises triethylene tetramine.

10. The herbicidal composition of claim 1 wherein the weight ratio of the microcapsule core to the shell wall is from 12:1 to 6:1.

11. The herbicidal composition of claim 1 further comprising one or more co-herbicides, wherein the co-herbicide is selected from acetyl CoA carboxylase inhibitors, organophosphorus herbicides, auxins, photosystem II inhibitors, acetolactate synthesis (ALS) inhibitors, protoporphyrinogen oxidase inhibitors and carotenoid biosynthesis inhibitors, salts and esters thereof, and mixtures thereof.

12. The herbicidal composition of claim 1 wherein the microcapsules have a mean particle size from about 9 μm to about 12 μm.

13. The herbicidal composition of claim 1 wherein the composition further comprises one or more of an emulsifying agent, pH buffer, biocide, preservative, antifreeze agent, antifoam agent, drift control agent, diluent, buffer, and/or anti-packing agent.

14. The herbicidal composition of claim 13 wherein the composition further comprises an emulsifying agent selected from the group consisting of maleic acid-olefin copolymers, gelatin, casein, polyvinyl alcohol, alkylated polyvinyl pyrrolidone polymers, maleic anhydride-methyl vinyl ether copolymers, styrene-maleic anhydride copolymers, maleic acid-butadiene and diisobutylene copolymers, sodium and calcium lignosulfonates, naphthalene formaldehyde condensate sulfonates, modified starches, and modified cellulosics.

15. The herbicidal composition of claim 13 wherein the composition further comprises a pH buffer comprising citric acid monohydrate, disodium phosphate, or combinations thereof.

16. The herbicidal composition of claim 1 wherein the composition comprises a thickener selected from guar- or xanthan-based gums.

17. The herbicidal composition of claim 11 wherein the co-herbicide comprises an auxin herbicide selected from the group consisting of 2,4-D (2,4-dichlorophenoxyacetic acid), 2,4-DB (4-(2,4-dichlorophenoxy) butyric acid), dichloroprop, MCPA ((4-chloro-2-methylphenoxy) acetic acid), MCPB (4-(4-chloro-2-methylphenoxy) butanoic acid), aminopyralid, clopyralid, fluroxypyr, triclopyr, diclopyr, mecoprop, dicamba, picloram and quinclorac, salts and esters thereof, and combinations thereof.

18. The herbicidal composition of claim 9 wherein the polyisocyanate component comprises a cycloaliphatic diisocyanate of structure (IX):

19. The herbicidal composition of claim 18 further comprising a thickener selected from the group consisting of guar- or xanthan-based gums, cellulose ethers, modified cellulosics and polymers, and microcrystalline cellulose anti-packing agents.

20. The herbicidal composition of claim 19 wherein the composition comprises a thickener selected from guar- or xanthan-based gums.

21. The composition of claim 18 further comprising urea.

22. The herbicidal composition of claim 9 wherein the amine molar equivalents contained in the polyamine component is in excess to the isocyanate molar equivalents contained in the polyisocyanate component.

23. The herbicidal composition of claim 9 wherein the ratio of amine molar equivalents contained in the polyamine component to isocyanate molar equivalents contained in the polyisocyanate component is from 1.1:1 to about 1.7:1.

24. The herbicidal composition of claim 9 wherein the weight to weight ratio of acetamide herbicide to the shell wall is from about 10:1 to about 6:1.

25. The herbicidal composition of claim 9 wherein the composition further comprises one or more of an emulsifying agen

Assignees

• Monsanto Technology Llc

Inventors

• Abraham William
• Becher David Z
• Bussler Brett H
• Herr Amanda C
• Prosch S Douglas

Classifications

• A01N37/26 Primary

  containing the group [IMAGE cpc-sch-A01N-0936.gif]; Thio analogues thereof · CPC title

• A01N2300/00

  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 title

• A01N25/28

  Microcapsules {or nanocapsules} · CPC title