IP Library › Granted Patent US 10,750,742

Granted Patent B2

US 10,750,742 · App. 16/064,916 · Granted Aug 25, 2020

Pesticidally active pyrazole derivatives

Inventors: André Jeanguenat (Stein, CH); Myriem El Qacemi (Stein, CH); Thomas Pitterna (Stein, CH); André Stoller (Stein, CH); Regis Jean Georges Mondiere (Stein, CH); Aurelien Bigot (Stein, CH); Andrew Edmunds (Stein, CH)

Assignee: Syngenta Participations AG

A01N43/56 A01N25/00 A01N25/26 A01N43/50 A01N43/713 A01N43/80 A01N53/00

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Quick Facts

Patent No.: US 10,750,742
App. No.: 16/064,916
Granted: Aug 25, 2020
Kind: B2

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Abstract

Compounds of formula (I), as defined herein, to processes for preparing them, to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests.

Claims (306)

1. A compound of formula (I),

wherein

R 1 is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 0 -C 3 )-alkyl and heteroaryl(C 0 -C 3 )-alkyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 0 -C 3 )-alkyl and heteroaryl(C 0 -C 3 )-alkyl is unsubstituted or substituted with 1 to 10 substituents independently selected from halogen, cyano, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl;

Q is selected from H, hydroxy, HC(═O)—, methylsulfonyl, carbamothioylcyclopropyl, 1-carbamoylcyclopropyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 heterocycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 3 -alkyl-C 3 -C 7 cycloalkyl, aryl(C 0 -C 3 )-alkyl, heteroaryl(C 0 -C 3 )-alkyl, N—C 1 -C 6 -alkylamino, N—C 1 -C 6 -alkylcarbonylamino and N,N-di (C 1 -C 6 -alkyl)amino, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 heterocycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 3 -alkyl-C 3 -C 7 cycloalkyl, aryl(C 0 -C 3 )-alkyl, heteroaryl(C 0 -C 3 )-alkyl, N—C 1 -C 6 -alkylamino, N—C 1 -C 6 -alkylcarbonylamino and N,N-di (C 1 -C 6 -alkyl)amino is unsubstituted or substituted with 1 to 10 substituents independently selected from halogen, hydroxyl, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;

W is O or S;

A 1 is CR 2 or N;

A 2 is CR 3 or N;

A 3 is CR 4 or N;

A 4 is CR 5 or N;

with the proviso that no more than 3 of A 1 , A 2 , A 3 and A 4 are N;

R 2 , R 3 , R 4 and R 5 are independently selected from H, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, N—C 1 -C 6 -alkylamino and N,N-di-C 1 -C 6 -alkylamino, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, N—C 1 -C 6 -alkylamino and N,N-di-C 1 -C 6 -alkylamino is unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;

T is a 5-membered heteroaryl of formula

wherein

indicates the bond to the pyrazole group;

D 1 is selected from CR 6a , N, NR 6b , O and S;

D 2 is selected from CR 7a , N, NR 7b , O and S;

D 3 is C or N;

D 4 is selected from CR 8a , N, NR 8b , S and O;

D 5 is C or N;

with the proviso that at least one of D 1 , D 2 , D 3 , D 4 and D 5 is selected from N, O and S, and that no more than one of D 1 , D 2 and D 4 is O or S, and that at least one of D 3 and D 5 is C;

R 6a , R 7a and R 8a are independently selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 5 halogen;

R 6b , R 7b and R 8b are independently selected from H and C 1 -C 6 -alkyl, wherein each of C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 5 halogen;

U is selected from —O— and —NR 100 —;

R 100 is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl and C 3 -C 6 -cycloalkyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 13 substituents independently selected from halogen;

Z 1 is selected from C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, —(C 0 -C 6 -alkyl)-C 3 -C 7 heterocycloalkyl, —(C 0 -C 6 -alkyl)-C 3 -C 6 -cycloalkyl and C 1 -C 10 -alkylsulfonyl, wherein each of C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, —(C 0 -C 6 -alkyl)-C 3 -C 7 heterocycloalkyl, —(C 0 -C 6 -alkyl)-C 3 -C 6 -cycloalkyl and C 1 -C 10 -alkylsulfonyl is unsubstituted or substituted with 1 to 20 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;

Z 2 is selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl; and

Z 3 is selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, aryl and heteroaryl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, aryl and heteroaryl is unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;

or an agrochemically acceptable salt or N-oxide thereof.

2. The compound or salt according to claim 1 , wherein T is selected from

wherein

indicates the bond to the pyrazole group.

3. The compound or salt according to claim 1 , wherein T is selected from

wherein

indicates the bond to the pyrazole group.

4. The compound or salt according to claim 1 , wherein U is —O—.

5. The compound or salt according to claim 1 , wherein U is —NR 100 —, and R 100 is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl and C 3 -C 6 -cycloalkyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 13 substituents independently selected from halogen.

6. The compound or salt according to claim 1 , wherein

R 1 is H;

Q is selected from 1-cyano-cyclopropyl, (E)-1,2,3,3,3-pentafluoroprop-1-enyl, cyanomethyl, benzyl, cyclopropyl, methyl, ethyl, 2-thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluorethyl, methylsulfonyl, thietan-3-yl and 1-carbamoylcyclopropyl;

W is O;

A 1 is CR 2 or N;

A 2 is CR 3 or N;

A 3 is CR 4 or N;

A 4 is CR 5 or N;

with the proviso that no more than 3 of A 1 , A 2 , A 3 and A 4 are N;

R 2 and R 5 are independently selected from H, methyl, fluoro and chloro;

R 3 and R 4 are independently selected from H, fluoro, chloro, bromo, iodo, cyano, nitro, methyl, ethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chloro-difluoromethoxy, dichloro-fluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1-(N-methoxyimino)-ethyl, methylsulfanyl, trifluoromethylsulfanyl, methylsulfonyl, methylsulfinyl, trifluoromethylsulfonyl and trifluoromethylsulfinyl;

U—Z 1 is selected from

difluoromethoxy;

2,2,2-trifluoroethoxy;

1,1,2,3,3,3-hexafluoropropoxy;

methoxy;

1,1,2,2-tetrafluoroethoxy;

2-bromo-1,1,2,2-tetrafluoroethoxy;

1,1,2,3,4,4,4-heptafluoro-3-(trifluoromethyl)butoxy;

1,1,2,4,4,4-hexafluoro-3-(trifluoromethyl)but-2-enoxy;

1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy;

1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethoxy;

2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy;

2,2,3,3,4,4,4-heptafluorobutoxy;

5,6,6-trifluorohex-5-enoxy;

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy;

2,2-difluoroethoxy;

2,2,3,3,4,4,5,5-octafluoropentoxy;

2-(trifluoromethoxy)ethoxy;

2,2,3,3-tetrafluoropropoxy;

1,1,2,2,3,3,3-heptafluoropropoxy;

1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexoxy;

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadeccafluorooctoxy;

2-bromo-1,1-difluoro-ethoxy;

(E)-2,3,3,3-tetrafluoro-1-(trifluoromethyl)prop-1-enoxy;

2-bromo-1,1,2-trifluoro-ethoxy;

2-chloro-1,1,2-trifluoro-ethoxy;

(1E)-1,2-difluorobuta-1,3-dienoxy;

3,4,4-trifluorobut-3-enoxy;

(Z)-1,3,3,3-tetrafluoroprop-1-enoxy;

(Z)-2-fluoro-1-(trifluoromethyl)vinyloxy;

2,2,3,3,4,4,5,5-octafluoropentoxy;

1,1,2,3,4,5,5,5-octafluoro-2-(trifluoromethyl)pent-3-enoxy;

1,2,3,3,3-pentafluoroprop-1-enoxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2,3,3-pentachloroallyloxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2,3,3-pentachloroallyloxy;

1,1,2-trifluoropropoxy;

2,2,2-trifluoroethylamino;

2-bromo-1,1,2-trifluoro-ethoxy; and

2-bromo-2-chloro-1,1-difluoro-ethoxy;

Z 2 is selected from H, halogen, cyano, nitro, amino, methyl, ethyl, 1,1-dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1 methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chlor-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, chloro-difluoromethylsulfanyl, chloro-difluoromethylsulfinyl, chloro-difluoromethylsulfonyl, dichloro-fluoromethylsulfanyl, dichloro-fluoromethylsulfinyl, dichloro-fluoromethylsulfonyl;

Z 3 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethenyl, 1-propenyl, 1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 1 fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl 2,6-dichloro-4-trifluoromethylphenyl, 3-chlor-5-trifluoromethylpyridin-2-yl, 4-NO 2 -phenyl and 3-chloro-pyridin-2-yl.

7. The compound or salt according to claim 1 , wherein

T is

R 1 is H;

R 7a and R 8a are independently selected from H, methyl and trifluoromethoxy;

W is O;

A 1 and A 4 are CH;

A 2 is CH or CF;

A 3 is CH or CCl;

U—Z 1 is selected from

difluoromethoxy;

2,2,2-trifluoroethoxy;

1,1,2,3,3,3-hexafluoropropoxy;

methoxy;

1,1,2,2-tetrafluoroethoxy;

2-bromo-1,1,2,2-tetrafluoroethoxy;

1,1,2,3,4,4,4-heptafluoro-3-(trifluoromethyl)butoxy;

1,1,2,4,4,4-hexafluoro-3-(trifluoromethyl)but-2-enoxy;

1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy;

1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethoxy;

2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy;

2,2,3,3,4,4,4-heptafluorobutoxy;

5,6,6-trifluorohex-5-enoxy;

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy;

2,2-difluoroethoxy;

2,2,3,3,4,4,5,5-octafluoropentoxy;

2-(trifluoromethoxy)ethoxy;

2,2,3,3-tetrafluoropropoxy;

1,1,2,2,3,3,3-heptafluoropropoxy;

1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexoxy;

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadeccafluorooctoxy;

2-bromo-1,1-difluoro-ethoxy;

(E)-2,3,3,3-tetrafluoro-1-(trifluoromethyl)prop-1-enoxy;

2-bromo-1,1,2-trifluoro-ethoxy;

2-chloro-1,1,2-trifluoro-ethoxy;

(1E)-1,2-difluorobuta-1,3-dienoxy;

3,4,4-trifluorobut-3-enoxy;

(Z)-1,3,3,3-tetrafluoroprop-1-enoxy;

(Z)-2-fluoro-1-(trifluoromethyl)vinyloxy;

2,2,3,3,4,4,5,5-octafluoropentoxy;

1,1,2,3,4,5,5,5-octafluoro-2-(trifluoromethyl)pent-3-enoxy;

1,2,3,3,3-pentafluoroprop-1-enoxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2,3,3-pentachloroallyloxy;

1,1,2,3,3,3-hexafluoropropoxy;

1,1,2,3,3-pentachloroallyloxy;

1,1,2-trifluoropropoxy;

2,2,2-trifluoroethylamino;

2-bromo-1,1,2-trifluoro-ethoxy; and

2-bromo-2-chloro-1,1-difluoro-ethoxy;

Z 2 is CF 3 ;

Z 3 is selected from methyl and ethyl.

8. A pesticidal composition, which comprises at least one compound according to claim 1 , or an agrochemically acceptable salt or N-oxide thereof, as active ingredient and at least one auxiliary.

9. The composition according to claim 8 , further comprising one or more active agents selected from insecticidally, acaricidally, nematicidally and fungicidally.

10. A method for controlling pests, which comprises applying the composition according to claim 8 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy.

11. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with the compound of claim 1 .

12. A coated plant propagation material, wherein a coating of the plant propagation material comprises in the compound of claim 1 .

13. A compound of formula (I),

wherein

W is O or S;

A 1 is CR 2 or N;

A 2 is CR 3 or N;

A 3 is CR 4 or N;

A 4 is CR 5 or N;

with the proviso that no more than 3 of A 1 , A 2 , A 3 and A 4 are N;

T is a 5-membered heteroaryl of formula:

T is a 5-membered heteroaryl of formula

wherein

indicates the bond to the pyrazole group;

R 6b , R 7b and R 8b are independently selected from H and C 1 -C 6 -alkyl, wherein each of C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 5 halogen;

U is selected from —S—, —SO— and —SO 2 —;

or an agrochemically acceptable salt or N-oxide thereof.

14. The compound or salt according to claim 13 , wherein

R 1 is H;

W is O;

A 1 is CR 2 or N;

A 2 is CR 3 or N;

A 3 is CR 4 or N;

A 4 is CR 5 or N;

with the proviso that no more than 3 of A 1 , A 2 , A 3 and A 4 are N;

R 2 and R 5 are independently selected from H, methyl, fluoro and chloro;

U—Z 1 is selected from

trifluoromethylsulfonate;

1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl;

2,2,3,3-tetrafluoropropylsulfanyl;

trifluoromethylsulfanyl;

1,1,2,2,3,3,3-heptafluoropropylsulfanyl;

15. The compound or salt according to claim 13 , wherein

T is

R 1 is H;

R 7a and R 8a are independently selected from H, methyl and trifluoromethoxy;

W is O;

A 1 and A 4 are CH;

A 2 is CH or CF;

A 3 is CH or CCl;

U—Z 1 is selected from

trifluoromethylsulfonate;

1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl;

2,2,3,3-tetrafluoropropylsulfanyl;

trifluoromethylsulfanyl;

1,1,2,2,3,3,3-heptafluoropropylsulfanyl;

Z 2 is CF 3 ; and

Z 3 is selected from methyl and ethyl.

16. The compound or salt according to claim 13 , wherein T is selected from

wherein

indicates the bond to the pyrazole group.

17. The compound or salt according to claim 13 , wherein T is selected from

wherein

indicates the bond to the pyrazole group.

18. A compound selected from:

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[(Z)-2-fluoro-1-(trifluoromethyl)vinyloxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-methoxy-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-N-[(E)-1,2,3,3,3-pentafluoroprop-1-enyl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-(difluoromethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-ethyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(cyanomethyl)-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2-tetrafluoroethoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

5-[1-[5-(2-bromo-1,1,2,2-tetrafluoro-ethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[1,1,2,3,4,4,4-heptafluoro-3-(trifluoromethyl)butoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[1,1,2,4,4,4-hexafluoro-3-(trifluoromethyl)but-2-enoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-4-(trifluoromethyl)-5-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]pyrazol-3-yl]pyrazol-4-yl]benzamide;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl]trifluoromethanesulfonate;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(2,2,3,3,4,4,4-heptafluorobutoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5-octafluoropentoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(5,6,6-trifluorohex-5-enoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(2,2-difluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-(2,2-difluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-[2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-(2,2,3,3,4,4,4-heptafluorobutoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5-octafluoropentoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[2-(trifluoromethoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(5,6,6-trifluorohex-5-enoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,3,3-tetrafluoropropoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,3-pentafluoropropoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3-tetrafluoropropoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-[2-(trifluoromethoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,2,3,3,3-heptafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

[5-[4-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl]1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

5-[1-[5-(2-bromo-1,1-difluoro-ethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(E)-2,3,3,3-tetrafluoro-1-(trifluoromethyl)prop-1-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide

5-[1-[5-(2-bromo-1,1,2-trifluoro-ethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

2-chloro-5-[1-[5-(2-chloro-1,1,2-trifluoro-ethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[(1E)-1,2-difluorobuta-1,3-dienoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(3,4,4-trifluorobut-3-enoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

5-[1-[5-(2-bromo-1,1,2-trifluoro-ethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-1-[2-methyl-5-[(Z)-1,3,3,3-tetrafluoroprop-1-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide; 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[(Z)-2-fluoro-1-(trifluoromethyl)vinyloxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[(E or Z)-1,1,2,3,4,5,5,5-octafluoro-2-(trifluoromethyl)pent-3-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-[(E or Z)-1,1,2,3,4,5,5,5-octafluoro-2-(trifluoromethyl)pent-3-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[(E or Z)-1,2,3,3,3-pentafluoroprop-1-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-[(E or Z)-1,2,3,3,3-pentafluoroprop-1-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

5-[1-[4-bromo-2-methyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfanyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-N-methyl-benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-methoxy-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-N-methyl-benzamide;

5-[1-[4-bromo-2-methyl-5-(2,2,3,3-tetrafluoropropylsulfanyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

N-cyclopropyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-methyl-benzamide;

N-(1-cyanocyclopropyl)-2-fluoro-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

N-cyclopropyl-2-fluoro-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-4-(trifluoromethyl)-5-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]pyrazol-3-yl]pyrazol-4-yl]pyridine-3-carboxamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-4-(trifluoromethyl)-5-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]pyrazol-3-yl]pyrazol-4-yl]pyridine-3-carboxamide;

5-[1-[4-bromo-2-methyl-5-(trifluoromethylsulfanyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

5-[1-[4-bromo-5-(1,1,2,2,3,3,3-heptafluoropropylsulfanyl)-2-methyl-pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]pyridine-3-carboxamide;

2-chloro-N-cyclopropyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]pyridine-3-carboxamide;

2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(1,1,2,3,3-pentachloroallyloxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

N-cyclopropyl-2-fluoro-3-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,3,3-pentachloroallyloxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide;

3-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-2-fluoro-N-(1-cyanocyclopropyl)benzamide;

N-cyclopropyl-3-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-2-fluoro-benzamide;

2-chloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-3-fluoro-benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-3-fluoro-benzamide;

2-chloro-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-4-fluoro-N-(1-cyanocyclopropyl)benzamide;

2-chloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-4-fluoro-benzamide;

2,4-dichloro-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)benzamide;

2,4-dichloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2,3-dichloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]benzamide;

2,3-dichloro-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)benzamide;

5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-2-fluoro-N-(1-cyanocyclopropyl)benzamide;

5-[1-[4-bromo-2-methyl-5-(2,2,2-trifluoroethylamino)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

5-[1-[5-(2-bromo-1,1,2-trifluoro-ethoxy)-2,4-dimethyl-pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

5-[1-[5-(2-bromo-1,1,2-trifluoro-ethoxy)-2,4-dimethyl-pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide;

2-chloro-N-cyclopropyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2,4-dimethyl-pyrazol-3-yl]triazol-4-yl]benzamide;

5-[1-[5-(2-bromo-2-chloro-1,1-difluoro-ethoxy)-2,4-dimethyl-pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

5-[1-[5-(2-bromo-2-chloro-1,1-difluoro-ethoxy)-2,4-dimethyl-pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-benzamide; and

2-chloro-N-cyclopropyl-5-[1-(5-methoxy-2,4-dimethyl-pyrazol-3-yl)triazol-4-yl]benzamide;

or an agrochemically acceptable salt or N-oxide thereof.

Assignments (3)

CHANGE OF NAME Recorded Apr 28, 2025

From: SYNGENTA PARTICIPATIONS AG

To: SYNGENTA CROP PROTECTION AG

Reel/Frame 071085/0107 →

MERGER AND CHANGE OF NAME Recorded Mar 14, 2025

From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG

To: SYNGENTA CROP PROTECTION AG

Reel/Frame 070518/0019 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2019

From: JEANGUENAT, ANDRÉ; EL QACEMI, MYRIEM; PITTERNA, THOMAS; STOLLER, ANDRÉ; MONDIERE, REGIS JEAN GEORGES; BIGOT, AURELIEN; EDMUNDS, ANDREW

To: SYNGENTA PARTICIPATIONS AG

Reel/Frame 048467/0085 →