Granted Patent B2

US 12,446,583 · App. 18/429,916 · Granted Oct 21, 2025

Inventors: Myriem El Qacemi (Stein, CH); Jerome Yves Cassayre (Stein, CH)

Assignee: SYNGENTA CROP PROTECTION AG

A01N43/80G06Q30/018

Abstract

Claims (321)

1. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more additional active ingredients including at least one of a) a pyrethroid, b) an organophosphate, c) a carbamate, d) a benzoyl urea, e) an organic tin compound, f) a pyrazole, g) macrolides, h) hormones or pheromones, i) an organochlorine, j) an amidine, k) a fumigant, l) a neonicotinoid, m) a diacylhydrazine, n) a diphenyl ether, o) a urea, p) a ketoenol, q) a diamide, r) an essential oil, or s) a compound selected from buprofezine, flonicamid, acequinocyl, bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin, fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin, iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen, flupyradifurone, 4-[(6-Chloro-pyridin-3-ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one, chlorfenapyr, pymetrozine, sulfoxaflor, and pyrifluqinazon.

2. The method of claim 1 , wherein the pyrethroid a) is selected from permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin, bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids, natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox, and

5-benzyl-3-furylmethyl-( E )-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropan e carboxylate.

3. The method of claim 1 , wherein the organophosphate b) is selected from profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate, and diazinon.

4. The method of claim 1 , wherein the carbamate c) is selected from pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl, and oxamyl.

5. The method of claim 1 , wherein the benzoyl urea d) is selected from diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron, and chlorfluazuron.

6. The method of claim 1 , wherein the organic tin compound e) is selected from cyhexatin, fenbutatin oxide, and azocyclotin.

7. The method of claim 1 , wherein the pyrazole f) is selected from tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate.

8. The method of claim 1 , wherein the macrolides g) are selected from avermectins and milbemycins, and preferably from abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin, and spinetoram.

9. The method of claim 1 , wherein the organochlorine i) is selected from endosulfan, alpha-endosulfan, benzene hexachloride, DDT, chlordane, and dieldrin.

10. The method of claim 1 , wherein the amidine j) is chlordimeform or amitraz.

11. The method of claim 1 , wherein the fumigant k) is selected from chloropicrin, dichloropropane, methyl bromide, and metam.

12. The method of claim 1 , wherein the neonicotinoid 1) is selected from imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, and nithiazine.

13. The method of claim 1 , wherein the diacylhydrazine m) is selected from tebufenozide, chromafenozide, and methoxyfenozide.

14. The method of claim 1 , wherein the diphenyl ether n) is diofenolan or pyriproxyfen.

15. The method of claim 1 , wherein the urea o) is indoxacarb or metaflumizone.

16. The method of claim 1 , wherein the ketoenol p) is selected from spirotetramat, spirodiclofen, and spiromesifen.

17. The method of claim 1 , wherein the diamide q) is selected from flubendiamide, chlorantraniliprole, and cyantraniliprole.

18. The method of claim 1 , wherein the Bt plants comprise at least one gene selected from CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CrylF.

19. The method of claim 1 , wherein the compound is compound A12

20. The method of claim 1 , wherein the compound is compound A20

21. The method of claim 1 , wherein the compound is A27

22. The method of claim 1 , wherein the compound is compound A28

23. The method of claim 1 , wherein the pest is a stinkbug.

24. The method of claim 23 , wherein the pest is a stinkbug Euschistus heros.

25. The method of claim 1 , wherein the compound is applied at a rate of 1 g to 1 kg per hectare.

26. The method of claim 1 , wherein the compound is part of a composition selected from dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions, micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.

27. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more additional active ingredients selected from buprofezine, flonicamid, acequinocyl, bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin, fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin, iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen, flupyradifurone, 4-[(6-Chloro-pyridin-3-ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one, chlorfenapyr, pymetrozine, sulfoxaflor, and pyrifluqinazon.

28. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more pyrethroid selected from permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin, bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids, natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox, and

5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropan e carboxylate.

29. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more pyrazole selected from tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate.

30. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more macrolides selected from abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin, and spinetoram.

31. A method of controlling pests on soybean plants, comprising:

applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (Ia),

wherein X 1 , R 1 , R 4 , R 5 , *, and **, as defined as follows

Stereo-

Stereo-

chemistry

chemistry

X1

R1

R4

R5

at *

at **

A12

3,5-dichloro-

ethyl

CH3

H

S

R

4-fluorophenyl

A20

3,5-

2,2,2-

CH3

H

S

R/S

dichlorophenyl

trifluoroethyl

A27

3,5-

2,2,2-

CH3

H

S

R

dichlorophenyl

trifluoroethyl

A28

3,5-

ethyl

CH3

H

S

R

dichlorophenyl

wherein the soybean plants are Bt plants, and

wherein the applying of the compound is admixed with one or more diamide selected from flubendiamide, chlorantraniliprole, and cyantraniliprole.

Assignments (1)

Priority Claims (2)

Continuity (2)

References Cited (12)