IP Library Granted Patent US 11,503,825
Granted Patent B2
US 11,503,825 · App. 17/182,864 · Granted Nov 22, 2022

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.
A01N25/14A01N53/00A01N57/20C05G3/60
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Quick Facts
Patent No.
US 11,503,825
App. No.
17/182,864
Granted
Nov 22, 2022
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 (28)

1. An aqueous formulation comprising:

nanoparticles comprising a polymer-associated pyrethroid compound, wherein the nanoparticles are in an aggregate and the aggregate has an average diameter of between about 10 nm and about 5000 nm;

wherein the polymer is a polyelectrolyte copolymer comprised of at least about 50 weight percent methacrylic acid monomers, a polyelectrolyte copolymer comprised of at least about 75 weight percent acrylic acid monomers, or combinations thereof;

a dispersant, that is not a sodium dodecylbenzene sulfonate wetting agent and/or dispersant, present at an amount of less than 5 weight percent;

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 a preservative; and

water;

wherein the nanoparticles comprising a polymer-associated pyrethroid compound comprise between about 1 weight % and about 50 weight % of the formulation.

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

3. The formulation of claim 1 , a ratio of the weight percent of the pyrethroid compound to the weight percent of the polymer is between about 1:10 to 10:1.

4. The formulation of claim 1 , wherein the polymer-associated pyrethroid compound has a melting point of less than 80° C.

5. The 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 formulation of claim 1 , further comprising between about 0.05 weight % and about 5 weight % of a thickener.

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

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

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

10. The formulation of claim 6 , wherein the thickener comprises between about 0.05 weight percent and about 2 weight percent of the formulation.

11. The 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 formulation of claim 1 , wherein the polymer-associated pyrethroid compound has a melting point of less than 100° C.

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

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

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

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

17. The method of claim 16 , wherein the formulation of claim 1 is diluted so that the concentration of the polymer-associated pyrethroid compound is between about 0.1 to about 1000 ppm, between about 10 to about 1000 ppm, between about 10 to about 500 ppm, or between about 10 to about 100 ppm prior to the applying step.

18. The method of claim 16 , wherein the pest to be controlled is a member of an order selected from lepidoptera, diptera, siphonaptera , ixodida, blattaria, isoptera, hymenoptera, hemiptera , coleopteran, thysanoptera and combinations thereof.

19. The method of claim 16 , wherein the pest is a mite.

20. The method of claim 16 wherein the plant or seed is a soybean or corn plant or seed, the pyrethroid is bifenthrin and is applied at a rate of between about 4 and about 37 grams of bifenthrin per hectare and the pest to be controlled is 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.

21. The method of claim 16 wherein the plant or seed is a soybean or corn plant or seed, the pyrethroid is lambda-cyhalothrin and is applied at a rate of about 2 and about 17 grams of lambda-cyhalothrin per hectare and the pest to be controlled is 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.

Assignments (3)
SECURITY INTEREST Recorded Dec 14, 2022
From: VIVE CROP PROTECTION INC.
To: SILICON VALLEY BANK
Reel/Frame 062087/0315 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2022
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 060516/0262 →
SECURITY INTEREST Recorded Apr 18, 2022
From: VIVE CROP PROTECTION INC.
To: SILICON VALLEY BANK
Reel/Frame 059627/0547 →
Continuity (8)
Continuation 16597021 · Oct 9, 2019
Continuation 15605472 · May 25, 2017
Continuation 14240222
Provisional Application 61641384 · May 2, 2012
Provisional Application 61641518 · May 2, 2012
Provisional Application 61589548 · Jan 23, 2012
Provisional Application 61526433 · Aug 23, 2011
Related Publication 20210321608A1 · Oct 21, 2021