IP Library Granted Patent US 12,419,307
Granted Patent B2
US 12,419,307 · App. 17/626,313 · Granted Sep 23, 2025

Mixtures comprising indazole pesticides

Inventor: Wenming Zhang (Newark, DE)
Assignee: FMC Corporation
A01N43/56A01M25/004A01N25/02A01P7/04A01C1/06A01M7/0042A01M7/0046B64D1/18
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Quick Facts
Patent No.
US 12,419,307
App. No.
17/626,313
Granted
Sep 23, 2025
Kind
B2
Abstract

Disclosed are compositions comprising compounds of Formula (I) and compounds of Formula (II). Also disclosed are compositions containing compounds of Formula (I) or compounds of Formula (II), or combinations thereof and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the disclosure.

Claims (31)

1. A composition comprising:

(a) at least one compound of

Formula I:

wherein n is 0, 1, or 2; or

at least one compound of Formula II:

wherein R is CH 3 , or CF 2 H; or

a combination of the foregoing compounds; and

(b) at least one additional invertebrate pest control agent selected from the group consisting of cyantraniliprole, chlorpyrifos, acetamiprid, bifenthrin, buprofezin, chlorfenapyr, flonicamid, flupyradifurone, imidacloprid, methomyl, methoxyfenozide, permethrin, spinetoram, spirotetramat, sulfoxaflor, tolfenpyrad, chlorantraniliprole, and indoxacarb;

wherein the weight ratio of the compound of Formula I or the compound of Formula II to component (b) is from 100:1 to 1:10;

provided that

(1) when component (a) is the compound of Formula I, then component (b) is other than, chlorpyrifos, buprofezin, chlorfenapyr, flonicamid, flupyradifurone, methomyl, methoxyfenozide, permethrin, sulfoxaflor, or tolfenpyrad; and

(2) when component (a) is the compound of Formula I, n is 2 and component (b) is indoxacarb then the weight ratio of the compound of Formula I to component (b) is other than 2:1.

2. The composition of claim 1 wherein component (a) is a compound selected from N-[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide and N-[1-(difluoromethyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide.

3. The composition of claim 1 wherein component (a) is N-[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide and component (b) is cyantraniliprole, acetamiprid, bifenthrin, imidacloprid, spinetoram, spirotetramat, chlorantraniliprole, or indoxacarb.

4. The composition of claim 1 wherein the weight ratio of the compound of Formula I or the compound of Formula II of component (b), is from 1:10 to 50:1.

5. The composition of claim 1 further comprising at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, said composition further comprising at least one additional biologically active compound or agent.

6. The composition of claim 1 further comprising a liquid fertilizer.

7. A soil drench formulation comprising the composition of claim 1 .

8. A spray composition comprising the composition of claim 1 and a propellant.

9. A bait composition, comprising: the composition of claim 1 , one or more food materials, optionally an attractant, and optionally a humectant.

10. A trap device for controlling an invertebrate pest, comprising: the bait composition of claim 9 and a housing adapted to receive said bait composition, wherein the housing has at least one opening sized to permit the invertebrate pest to pass through the opening so the invertebrate pest can gain access to said bait composition from a location outside the housing, and wherein the housing is further adapted to be placed in or near a locus of potential or known activity for the invertebrate pest.

11. A composition comprising the composition of claim 1 wherein the composition is a solid composition selected from the group consisting of dusts, powders, granules, pellets, prills, pastilles, tablets, and filled films.

12. The composition of claim 11 wherein the composition is water-dispersible or water-soluble.

13. A liquid or dry formulation comprising the composition of claim 1 for use in a drip irrigation system, furrow during planting, handheld sprayer, backpack sprayer, boom sprayer, ground sprayer, aerial application, unmanned aerial vehicle, or a seed treatment.

14. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a composition or formulation of claim 1 .

15. The method of claim 14 wherein the composition or formulation is dispensed by a drip irrigation system, furrow during planting, handheld sprayer, backpack sprayer, boom sprayer, ground sprayer, aerial application, or an unmanned aerial vehicle.

16. A treated seed comprising the composition or formulation of claim 1 in an amount of from about 0.0001 to 1% by weight of the seed before treatment.

17. The composition of claim 1 wherein component (a) is N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide and component (b) is cyantraniliprole, acetamiprid, bifenthrin, imidacloprid, spinetoram, spirotetramat, chlorantraniliprole, or indoxacarb.

18. The composition of claim 1 wherein component (a) is N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide and component (b) is cyantraniliprole, acetamiprid, bifenthrin, imidacloprid, spinetoram, spirotetramat, chlorantraniliprole, or indoxacarb.

19. The composition of claim 1 wherein component (a) is N-(1-methyl-cyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide and component (b) is cyantraniliprole, chlorpyrifos, acetamiprid, bifenthrin, buprofezin, chlorfenapyr, flonicamid, flupyradifurone, imidacloprid, methomyl, methoxyfenozide, permethrin, spinetoram, spirotetramat, sulfoxaflor, tolfenpyrad, chlorantraniliprole, or indoxacarb.

20. The composition of claim 1 wherein component (a) is N-[1-(difluoro-methyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide and component (b) is cyantraniliprole, chlorpyrifos, acetamiprid, bifenthrin, buprofezin, chlorfenapyr, flonicamid, flupyradifurone, imidacloprid, methomyl, methoxyfenozide, permethrin, spinetoram, spirotetramat, sulfoxaflor, tolfenpyrad, chlorantraniliprole, or indoxacarb.

Assignments (2)
PATENT SECURITY AGREEMENT Recorded Apr 17, 2026
From: FMC CORPORATION
To: CITIBANK, N.A.
Reel/Frame 075403/0891 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2022
From: ZHANG, WENMING
To: FMC CORPORATION
Reel/Frame 058886/0591 →