IP Library Granted Patent US 11,559,057
Granted Patent B2
US 11,559,057 · App. 17/071,061 · Granted Jan 24, 2023

Insecticidal mixtures of bifenthrin and chlorantraniliprole

Inventors: John T. Andaloro (Hockessin, DE); Seth David Delaney (Franklin, NC); Hector Eduardo Portillo (Newark, DE); Luis Teixeira (Haddonfield, NJ); Guozhi Wang (Oakland Gardens, NY)
Assignee: FMC Corporation and FMC Agro Singapore Pte. Ltd.
A01N43/56A01N25/04A01N31/04
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Quick Facts
Patent No.
US 11,559,057
App. No.
17/071,061
Granted
Jan 24, 2023
Kind
B2
Abstract

Improved concentrate, premix and tank mix compositions comprising bifenthrin and chlorantraniliprole are provided.

Claims (60)

1. An insecticidal concentrate composition, the composition comprising bifenthrin and chlorantraniliprole, wherein the weight ratio of bifenthrin to chlorantraniliprole on an active ingredient basis is from about 10:1 to about 1:10, wherein the composition is an oil dispersion, and wherein the composition comprises:

(i) from about 20 wt. % to about 35 wt. % bifenthrin, and

(ii) from about 5 wt. % to about 9 wt. % chlorantraniliprole;

and wherein the composition further comprises

(iii) from about 1 wt. % to about 10 wt. % of a dispersant component comprising at least one dispersant compound,

(iv) from about 1 wt. % to about 10 wt. % of an emulsifier component comprising at least one emulsifier compound,

(v) from about 0.1 wt. % to about 5 wt. % of a rheology modifier component comprising at least one rheology modifier compound,

(vi) from about 10 wt. % to about 60 wt. % of a solvent component comprising at least one organic solvent compound, and

(vii) from about 10 wt. % to about 60 wt. % of a carrier component comprising at least one organic carrier compound, and wherein the wt. % of each component is based on the total weight of the composition.

2. An insecticidal concentrate composition, the composition comprising bifenthrin and chlorantraniliprole, wherein the weight ratio of bifenthrin to chlorantraniliprole on an active ingredient basis is from about 10:1 to about 1:10, wherein the composition is a suspoemulsion, wherein the composition comprises:

(i) from about 20 wt. % to about 35 wt. % bifenthrin, and

(ii) from about 5 wt. % to about 9 wt. % chlorantraniliprole;

and wherein the composition further comprises

(iii) from about 1 wt. % to about 10 wt. % of a dispersant component comprising at least one dispersant compound;

(iv) from about 1 wt. % to about 10 wt. % of an emulsifier component comprising at least one emulsifier compound;

(v) from about 0.1 wt. % to about 5 wt. % of a rheology modifier component comprising at least one rheology modifier compound;

(vi) from about 5 wt. % to about 50 wt. % of a solvent component comprising at least one organic solvent compound;

(vii) from about 10 wt. % to about 60 wt. % of a carrier component comprising water; and

(viii) from about 5 wt. % to about 50 wt. % of an adjuvant component comprising at least one efficacy enhancer compound, and wherein the wt. % of each component is based on the total weight of the composition.

3. The insecticidal composition of claim 2 , wherein the solvent (vi) is an organic solvent and is present in an amount.

4. The insecticidal composition of claim 3 wherein the efficacy enhancer comprises a phosphate ester of Formula I

wherein

R 1 is a straight-chain or branched alkyl having from 4 to 12 carbon atoms, or a phenyl group optionally substituted with from 1 to 3 C 1 -C 4 straight-chain or branched alkyl groups, and

R 2 and R 3 are each independently a straight-chain or branched alkyl having from 2 to 8 carbon atoms, or a phenyl group optionally substituted with from 1 to 3 C 1 -C 4 straight-chain or branched alkyl groups.

5. The composition of claim 3 , wherein the efficacy enhancer is selected from the group consisting of trixylenyl phosphate, butylatated phenol phosphate, tris(isopropylphenyl) phosphate, cresyl diphenyl phosphate, isopropylphehyl diphenyl phosphate, t-butylphenyl diphenyl phosphate, 2-ethylhexyl, diphenyl phosphate, iosdecyl diphenyl phosphate, tri-n-butyl phosphate, tri-n-pentyl phosphate, tri-n-hexyl phosphate, tri-n-heptyl phosphate, tri-n-octyl phosphate, nonyl dioctyl phosphate, butyl dioctyl phosphate, dibutyl nonyl phosphate, butan-2-yl dibutyl phosphate, butan-2-yl diethyl phosphate, butan-2-yl bis(2-methylpropyl) phosphate, 3-methylbutyl dipropan-2-yl phosphate, tris-(2-ethylhexyl)phosphate, tri-iso-butyl phosphate, tributoxylethyl phosphate, and combinations thereof.

6. The composition of claim 3 , wherein the efficacy enhancer is a phosphate ester and the phosphate ester is selected from the group consisting of tris-(2-ethylhexyl)phosphate, tri-n-octyl phosphate, and tri-iso-butyl phosphate.

7. A method for controlling insect pests on plants, the method comprising applying the composition of claim 3 to a plurality of the plants.

8. The composition of claim 3 further comprising an aromatic hydrocarbon solvent.

9. The suspoemulsion composition of claim 2 , wherein the composition further comprises:

from about 0.05 wt. % to about 1 wt. % of an antifoam component comprising at least one antifoam compound;

from about 0.01 wt. % to about 0.5 wt. % of a biocide component comprising at least one biocide compound; and from about 1 wt. % to about 10 wt. % of an antifreeze component comprising at least one antifreeze compound.

10. The suspoemulsion composition of claim 3 , wherein the composition further comprises:

from about 0.05 wt. % to about 1 wt. % of an antifoam component comprising at least one antifoam compound;

from about 0.01 wt. % to about 0.5 wt. % of a biocide component comprising at least one biocide compound; and from about 1 wt. % to about 10 wt. % of an antifreeze component comprising at least one antifreeze compound.

11. An insecticidal concentrate composition, the composition comprising bifenthrin and chlorantraniliprole, wherein the weight ratio of bifenthrin to chlorantraniliprole on an active ingredient basis is from about 10:1 to about 1:10, wherein the composition is a suspension concentrate, wherein the composition comprises:

(i) from about 20 wt. % to about 35 wt. % bifenthrin, and

(ii) from about 5 wt. % to about 9 wt. % chlorantraniliprole;

and wherein the composition further comprises

(iii) from about 1 wt. % to about 10 wt. % of a dispersant component comprising at least one dispersant compound;

(iv) from about 0.05 wt. % to about 5 wt. % of a rheology modifier component comprising at least one rheology modifier compound; and

(v) from about 20 wt. % to about 70 wt. % of a carrier component comprising water, at least organic solvent compound, or a combination thereof, and wherein the wt. % of each component is based on the total weight of the composition.

12. An insecticidal concentrate composition, the composition comprising bifenthrin and chlorantraniliprole, wherein

(i) the weight ratio of bifenthrin to chlorantraniliprole on an active ingredient basis is from about 10:1 to about 1:10, wherein the composition is a concentrate comprising:

(i) from about 11 wt. % to about 20 wt. % bifenthrin, and

(ii) from about 5 wt. % to about 15 wt. % chlorantraniliprole;

and wherein the composition further comprises

(iii) from about 1 wt. % to about 10 wt. % of a dispersant component comprising at least one dispersant compound,

(iv) from about 1 wt. % to about 10 wt. % of a wetting agent component comprising at least one wetting agent compound,

(v) from about 1 wt. % to about 12 wt. % of a rheology modifier component comprising at least one rheology modifier compound, and

(vi) from about 20 wt. % to about 60 wt. % water, and wherein the wt. % of each component is based on the total weight percentage of the composition.

13. The insecticidal composition of claim 1 , 2 , 11 or 12 , wherein the efficacy enhancer component comprises

a phosphate ester of Formula I

wherein

R 1 is a straight-chain or branched alkyl having from 4 to 12 carbon atoms, or a phenyl group optionally substituted with from 1 to 3 C 1 -C 4 straight-chain or branched alkyl groups, and

R 2 and R 3 are each independently a straight-chain or branched alkyl having from 2 to 8 carbon atoms, or a phenyl group optionally substituted with from 1 to 3 C 1 -C 4 straight-chain or branched alkyl groups.

14. The composition of claim 1 , 2 , 11 or 12 , further comprising an efficacy enhancer and wherein the efficacy enhancer is selected from the group consisting of trixylenyl phosphate, butylatated phenol phosphate, tris(isopropylphenyl) phosphate, cresyl diphenyl phosphate, isopropylphehyl diphenyl phosphate, t-butylphenyl diphenyl phosphate, 2-ethylhexyl, diphenyl phosphate, iosdecyl diphenyl phosphate, tri-n-butyl phosphate, tri-n-pentyl phosphate, tri-n-hexyl phosphate, tri-n-heptyl phosphate, tri-n-octyl phosphate, nonyl dioctyl phosphate, butyl dioctyl phosphate, dibutyl nonyl phosphate, butan-2-yl dibutyl phosphate, butan-2-yl diethyl phosphate, butan-2-yl bis(2-methylpropyl) phosphate, 3-methylbutyl dipropan-2-yl phosphate, tris-(2-ethylhexyl)phosphate, tri-iso-butyl phosphate, tributoxylethyl phosphate, and combinations thereof.

15. The composition of claim 1 , 2 , 11 or 12 , wherein the phosphate ester is selected from the group consisting of tris-(2-ethylhexyl)phosphate, tri-n-octyl phosphate, and tri-iso-butyl phosphate.

16. A method for controlling insect pests on plants, the method comprising applying the composition of claim 1 , 2 , 11 , or 12 to a plurality of the plants.

17. The composition of any one of claim 1 , 2 , 11 , or 12 wherein the organic solvent comprises an aromatic hydrocarbon solvent.

18. The concentrate composition of claim 12 , wherein the composition is selected from an oil dispersable composition, a suspension concentrate composition, and a suspoemulsion composition.

Assignments (4)
PATENT SECURITY AGREEMENT Recorded Apr 17, 2026
From: FMC CORPORATION
To: CITIBANK, N.A.
Reel/Frame 075403/0891 →
CHANGE OF ADDRESS Recorded Sep 14, 2025
From: FMC IP TECHNOLOGY GMBH
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 072892/0066 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2024
From: FMC AGRO SINGAPORE PTE. LTD.
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 067639/0738 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2021
From: ANDALORO, JOHN T.; DELANEY, SETH DAVID; PORTILLO, HECTOR EDUARDO; TEIXEIRA, LUIS; WANG, GUOZHI
To: FMC CORPORATION; FMC AGRO SINGAPORE PTE. LTD.
Reel/Frame 056159/0438 →
Continuity (2)
Provisional Application 62923152 · Oct 18, 2019
Related Publication 20210112810A1 · Apr 22, 2021