IP Library Granted Patent US 9,686,979
Granted Patent B2
US 9,686,979 · App. 14/240,222 · Granted Jun 27, 2017

Pyrethroid formulations

Inventors: Danielle Norton (Toronto, CA); Nikolai Loukine (Toronto, CA); Rachel Gong (Mississauga, CA); Henry Galas (Toronto, CA); Jose Amado Dinglasan (Toronto, CA); Anjan Kumar Das (Oakville, CA); Darren J. Anderson (Toronto, CA)
Assignee: Vive Crop Protection Inc.
A01N25/14A01N53/00A01N57/20C05G3/02
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Quick Facts
Patent No.
US 9,686,979
App. No.
14/240,222
Granted
Jun 27, 2017
Kind
B2
Abstract

The present disclosure provides formulations of pyrethroid compounds comprising nanoparticles of polymer-associated pyrethroid compounds along with various formulating agents. The present disclosure also provides methods for producing and using these formulations. The disclosure describes various formulations and formulating agents that can be included in the formulations. Additionally, the disclosures describes application to various plants and pests as well as advantages of the disclosed formulations.

Claims (40)

1. An aqueous formulation comprising:

nanoparticles comprising a polymer and a pyrethroid compound with an average diameter of between about 1 nm and about 500 nm;

wherein the polymer is a polyelectrolyte copolymer comprised of between about 50 weight percent and about 95 weight percent methacrylic acid monomers and between about 50 weight percent and about 5 weight percent ethyl acrylate or styrene monomers;

between about 0.5 weight percent and about 5 weight percent of a naphthalene sulfonate condensate dispersant;

between about 0.5 weight percent and about 5 weight percent of a sodium dodecylbenzene sulfonate wetting agent;

between about 0.1 weight percent and about 1 weight percent of an anti-foaming agent;

between about 0.01 weight percent and about 0.1 weight percent of a preservative; and

water;

wherein the nanoparticles comprise between about 5 weight percent and about 50 weight percent of the formulation.

2. The aqueous formulation of claim 1 , wherein the pyrethroid compound comprises between about 5 weight percent and about 40 weight percent of the formulation.

3. The aqueous formulation of claim 1 , wherein a ratio of a weight percent of the pyrethroid compound to a weight percent of the polymer is between about 1:1 to 5:1.

4. The aqueous formulation of claim 1 ; wherein the pyrethroid compound has a melting point of less than 80° C.

5. The aqueous formulation of claim 1 ; wherein the pyrethroid compound is selected from the group consisting of bifenthrin, gamma-cyhalothrin, lambda-cyhalothrin; cypermethrin, zeta-cypermethrin; beta-cypermethrin, esfenvalerate, fenvalerate, permethrin, resmethrin, acrinathrin, and combinations thereof.

6. The aqueous formulation of claim 1 , further comprising a thickener.

7. The aqueous formulation of claim 1 , further comprising an anti-freeze agent.

8. The aqueous formulation of claim 1 , further comprising a fungicide.

9. The aqueous formulation of claim 1 , wherein the polyelectrolyte copolymer is a poly(methacrylic acid-co-ethyl acrylate) copolymer.

10. The aqueous formulation of claim 6 , wherein the thickener comprises between about 0.05 weight percent and about 5 weight percent of the formulation.

11. The aqueous formulation of claim 7 , wherein the anti-freeze agent comprises between about 1 weight percent and about 10 weight percent of the formulation.

12. The aqueous formulation of claim 1 , wherein the pyrethroid compound has a melting point of less than 100° C.

13. The aqueous formulation of claim 1 , without a UV-blocker.

14. The aqueous formulation of claim 1 , further comprising a liquid fertilizer.

15. The aqueous formulation of claim 14 , wherein the fertilizer comprises at least one of the elements selected from the group consisting of: boron, copper, manganese, iron, chorine, molybdenum, zinc sulfur, nitrogen, phosphorus and potassium.

16. A method of controlling pests comprising applying the aqueous formulation of claim 1 to a plant, a soil adjacent to a plant, to soil where a seed is or will be planted.

17. The method of claim 16 , wherein the pests to be controlled are members of an order selected from the group consisting of lepidoptera, diptera, Siphonaptera, ixodida, blattaria, isoptera, hymenoptera, hemiptera, coleopteran, thysanoptera and combinations thereof.

18. The method of claim 16 , wherein the pests are mites.

19. The method of claim 16 wherein the pyrethroid compound is bifenthrin and is applied at a rate of between about 4 and about 37 grams of bifenthrin per hectare and the pests to be controlled are selected from the group consisting of Alfalfa Caterpillar, Aphids, Aster Leafhopper, Bean Leaf Beetle, Beet Armyworm, Cloverworm, Corn Earworm, Corn Rootworm (adult), Cucumber Beetles, Cutworms, European Corn Borer, Fall Armyworm, Flea Beetle, Grasshoppers, Imported Cabbageworm, Japanese Beetle (Adult), Leafhoppers, Leafminer, Loopers, Mexican Bean Beetle (adult), Pea Leaf Weevil, Pea Weevil, Plant Bug, Saltmarsh Caterpillar, Sap Beetle, Southern Armyworm, Stink Bugs, Tarnished Plant Bug, Thrips , Tobacco budworm, Webworms, Western Bean Cutworm, Whitefly, and Yellowstriped armyworm.

20. The method of claim 16 wherein the pyrethroid compound is lambda-cyhalothrin and is applied at a rate of about 2 and about 17 grams of lambda-cyhalothrin per hectare and the pests are selected from the group consisting of Bean Leaf Beetle, Cabbage Looper Corn Earworm, Cutworm spp., Green Cloverworm, Mexican Bean Beetle, Mexican Corn Rootworm Beetle (Adult), Northern Corn Rootworm Beetle (Adult), Painted Lady (Thistle) Caterpillar, Potato Leafhopper, Saltmarsh Caterpillar, Southern Corn Rootworm Beetle (Adult), Soybean Aphids, Three-cornered Alfalfa Hopper, Thrips , Velvetbean Caterpillar, Western Corn Rootworm Beetle (Adult), and Woollybear Caterpillar.

21. The aqueous formulation of claim 1 , wherein the polyelectrolyte copolymer is a poly(methacrylic acid-co-styrene) copolymer.

22. The aqueous formulation of claim 1 , wherein the polyelectrolyte copolymer is water soluble at pH 7.

23. The aqueous formulation of claim 1 , wherein the polyelectrolyte copolymer has a water solubility at pH 7 of greater than 30%.

24. An aqueous formulation comprising:

nanoparticles comprising a polymer and a pyrethroid compound with an average diameter of between about 1 nm and about 500 nm;

wherein the polymer is a polyelectrolyte copolymer comprised of between about 75 weight percent and about 90 weight percent acrylic acid monomers and between about 25 weight percent and about 10 weight percent styrene monomers;

between about 0.5 weight percent and about 5 weight percent of a naphthalene sulfonate condensate dispersant;

between about 0.5 weight percent and about 5 weight percent of a sodium dodecylbenzene sulfonate wetting agent;

between about 0.1 weight percent and about 1 weight percent of an anti-foaming agent;

between about 0.01 weight percent and about 0.1 weight percent of a preservative; and

water;

wherein the nanoparticles comprise between about 5 weight % and about 50 weight % of the formulation.

Assignments (4)
SECURITY INTEREST Recorded Apr 18, 2022
From: VIVE CROP PROTECTION INC.
To: SILICON VALLEY BANK
Reel/Frame 059627/0547 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CANADIAN IMPERIAL BANK OF COMMERCE
To: VIVE CROP PROTECTION INC.
Reel/Frame 059271/0993 →
SECURITY INTEREST Recorded Oct 1, 2019
From: VIVE CROP PROTECTION INC
To: CANADIAN IMPERIAL BANK OF COMMERCE, AS LENDER
Reel/Frame 050582/0102 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2014
From: NORTON, DANIELLE; LOUKINE, NIKOLAI; GONG, RACHEL; GALAS, HENRY; DINGLASAN, JOSE AMADO; DAS, ANJAN KUMAR; ANDERSON, DARREN J.
To: VIVE CROP PROTECTION INC.
Reel/Frame 032281/0094 →
Continuity (5)
Provisional Application 61526433 · Aug 23, 2011
Provisional Application 61589548 · Jan 23, 2012
Provisional Application 61641384 · May 2, 2012
Provisional Application 61641518 · May 2, 2012
Related Publication 20140187424A1 · Jul 3, 2014