Methods to produce polymer nanoparticles and formulations of active ingredients

• US 8,741,808 B2
• Filed: 01/15/2013
• Issued: 06/03/2014
• Est. Priority Date: 09/25/2008
• Status: Expired due to Term

• Current Assignee: Vive Crop Protection Inc.
• Original Assignee: Vive Crop Protection Inc.
• Inventors: Li, Fugang, Anderson, Darren J., Pham, Hung Hoang
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): CRAIGO, WILLIAM A
• Application Number:
  US13/741,673
• Publication Number:
  US 20130130904A1
• Time in Patent Office: 504 Days
• Field of Search: None
• US Class Current: 504/206
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/68 with two or three nitrogen atoms directly attached to ring carbon atoms
• CPC Class Codes: A01N 43/70 Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• CPC Class Codes: A01N 51/00 Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C08J 2333/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08J 2339/02 Homopolymers or copolymers of vinylamine
• CPC Class Codes: C08J 3/14 by precipitation from solutions C08J3/122 takes precedence
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08J 3/28 Treatment by wave energy or particle radiation
• CPC Class Codes: C08K 2201/011 Nanostructured additives
• CPC Class Codes: C08K 5/0058 Biocides; macromolecular substances as carriers for biocide material A01N25/10
• CPC Class Codes: C08L 25/18 : Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
• CPC Class Codes: C08L 33/02 : Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 39/02 : Homopolymers or copolymers of vinylamine
• CPC Class Codes: C08L 5/08 : Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 105/08 : Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: Y10T 428/2982 : Particulate matter [e.g., sphere, flake, etc.]

Abstract

The present invention provides a composition including a polymer nanoparticle and at least one agricultural active compound incorporated with the nanoparticle, wherein the nanoparticle are less than 100 nm in diameter, and the polymer includes a polyelectrolyte.

Claims

1. A composition comprising a polymer nanoparticle and at least one organic, neutral, non-ionic agricultural compound associated with the polymer nanoparticle, wherein the polymer nanoparticle is less than 100 nm in diameter and cross-Linked;

wherein the polymer nanoparticle comprises a collapsed water-soluble polyelectrolyte;

wherein the polyelectrolyte has a molecular weight of at least about 100,000 Dalton prior to collapse and cross-linking; and

wherein the agricultural compound is a fungicide.

2. The composition of claim 1, wherein the fungicide has a mode of action that targets cell respiration or inhibits sterol biosynthesis in cell membranes.

3. The composition of claim 1, wherein the fungicide is selected from the group consisting of sterol demethylation inhibitors, quinone-outside inhibitors and combinations thereof.

4. The composition of claim 1, wherein the fungicide is a combination of fungicides the first selected from the group consisting of azoxystrobin, pyraclostrobin, trifloxystrobin, and fluoxastrobin and the second is a sterol demethylation inhibitor.

5. The composition of claim 3, wherein the fungicide is a quinone-outside inhibitor selected from the group consisting of azoxystrobin, pyraclostrobin, trifloxystrobin, fluoxastrobin and combinations thereof.

6. The composition of claim 1, wherein the fungicide is azoxystrobin.

7. The composition of claim 3, wherein the fungicide is a sterol demethylation inhibitor.

8. The composition of claim 1, wherein the polymer nanoparticle comprises multiple collapsed water-soluble polyelectrolyte molecules that each have a molecular weight of at least about 100,000 Dalton prior to collapse and cross-linking.

9. A dispersion comprising the composition of claim 3, wherein the fungicide is dispersed at a concentration higher than its solubility in the absence of the polymer nanoparticle.

10. The composition of claim 3, wherein the water-soluble polyelectrolyte is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(styrene sulfonate), and copolymers comprising these polymers.

11. The composition of claim 10, wherein the polyelectrolyte is a copolymer of poly(acrylic acid) and/or poly(methacrylic acid).

12. The composition of claim 1, wherein the water-soluble polyelectrolyte has a molecular weight of at least about 250,000 Daltons prior to collapse and cross-linking.

13. The composition of claim 6, wherein the water-soluble polyelectrolyte is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(styrene sulfonate), and copolymers comprising these polymers.

14. The composition of claim 13, wherein the polyelectrolyte is a copolymer of poly(acrylic acid) and/or poly(methacrylic acid).

15. The composition of claim 7, wherein the water-soluble polyelectrolyte is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(styrene sulfonate), and copolymers thereof.

16. The composition of claim 15, wherein the polyelectrolyte is a copolymer of poly(acrylic acid) and/or poly(methacrylic acid).

17. A composition comprising a polymer nanoparticle and at least one organic, neutral, non-ionic agricultural compound associated with the polymer nanoparticle, wherein the polymer nanoparticle is less than 100 nm in diameter and cross-linked;

wherein the polymer nanoparticle comprises a collapsed water-soluble polyelectrolyte;

wherein the polymer has a molecular weight of at least about 100,000 Dalton prior to collapse and cross-linking; and

wherein the agricultural compound is an insecticide.

18. The composition of claim 17, wherein the insecticide has a mode of action selected from the group consisting of sodium channel modulators, chloride channel inhibitors, nicotinic acetylcholine receptor agonists, and combinations thereof.

19. The composition of claim 17, wherein the insecticide is selected from the group consisting of pyrethroids, mectins, and combinations thereof.

20. The composition of claim 19, wherein the insecticide is a pyrethroid selected from the group consisting of lambda-cyhalothrin, bifenthrin, and combinations thereof.

21. The composition of claim 20, wherein the insecticide is lambda-cyhalothrin.

22. The composition of claim 19, wherein the insecticide is a mectin selected from the group consisting of abamectin, emamectin, emamectin salts and combinations thereof.

23. The composition of claim 17, wherein the polymer nanoparticle comprises multiple collapsed water-soluble polyelectrolyte molecules that each have a molecular weight of at least about 100,000 Dalton prior to collapse and cross-linking.

24. A dispersion comprising the composition of claim 21, wherein the insecticide is dispersed at a concentration higher than its solubility in the absence of the polymer nanoparticle.

25. The composition of claim 17, wherein the water-soluble polyelectrolyte is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(styrene sulfonate), and copolymers comprising these polymers.

26. The composition of claim 25, wherein the polyelectrolyte is a copolymer of poly(acrylic acid) and/or poly(methacrylic acid).

27. The composition of claim 17, wherein the water-soluble polyelectrolyte has a molecular weight of at least about 250,000 Daltons prior to collapse and cross-linking.