IP Library › Granted Patent US 11,071,300
Granted Patent B2
US 11,071,300 · App. 16/624,710 · Granted Jul 27, 2021

Pesticidally active pyrazole derivatives

Inventors: André Jeanguenat (Stein, CH); Myriem El Qacemi (Stein, CH); André Stoller (Stein, CH); Aurelien Bigot (Stein, CH); Denis Gribkov (Münchwilen, CH)
Assignee: SYNGENTA PARTICIPATIONS AG
A01N43/56A01N43/80C07D401/14C07D403/04C07D413/02
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Quick Facts
Patent No.
US 11,071,300
App. No.
16/624,710
Granted
Jul 27, 2021
Kind
B2
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 (140)

1. A compound of formula (I),

wherein

Z 1 is selected from C 1 -C 4 haloalkyl and F;

T is selected from

wherein indicates the bond to the pyrazole group;

R 5 and R 6 are independently selected from H, methyl and trifluoromethoxy;

A is selected from C—H and N;

R 2 is selected from H, methyl, trifluoromethyl and halogen;

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, formyl, 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)—, 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;

wherein the compound of formula (I) is not [5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] trifluoromethanesulfonate, or [5-[4-[4-chloro-3-(cyanocyclopropylcarbamoyl)phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate, or [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;

or an agrochemically acceptable salt or N-oxide thereof.

2. A compound or salt according to claim 1 of formula (I)

wherein

Z 1 is selected from C 1 -C 4 haloalkyl and F;

T is selected from

wherein indicates the bond to the pyrazole group;

R 5 and R 6 are independently selected from H, methyl and trifluoromethoxy;

A is selected from C—H and N;

R 2 is selected from H, methyl, trifluoromethyl and halogen;

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, formyl, 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)—, 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, 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;

with the proviso that when T is T6, A is C—H, R 5 and R 6 are H, Z 1 is CF 3 or CF 2 CF 2 CF 2 CF 3 , and Q is cyclopropyl or 1-cyanocyclopropyl, then R 1 is not H;

or an agrochemically acceptable salt or N-oxide thereof.

3. A compound or salt according to claim 1 of formula (I)

wherein

Z 1 is selected from

F,

CF 2 CF 3 ,

CF 2 CF 2 C 1 ,

CF 2 CFCl 2 ,

CF 2 CF 2 CF 3 ,

CF(CF 3 )(CF 3 ),

CF 2 CF 2 CF 2 C 1 ,

CF(CF 3 )(CF 2 C 1 ),

CF 2 CF 2 CFCl 2 ,

CF(CF 3 )(CFCl 2 ),

CF 2 CF 2 CF 2 CF 3 ,

CF(CF 3 )CF 2 CF 3 ,

CF 2 CF(CF 3 )(CF 3 ),

C(CF 3 )(CF 3 )(CF 3 );

T is selected from

wherein indicates the bond to the pyrazole group;

R 5 and R 6 are independently selected from H, methyl and trifluoromethoxy;

A is selected from C—H and N;

R 2 is selected from H, methyl, trifluoromethyl and halogen;

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, formyl, 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)—, 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;

with the proviso that when T is T6, A is C—H, R 5 and R 6 are H, Z 1 is CF 3 or CF 2 CF 2 CF 2 CF 3 , and Q is cycloproyl or 1-cyanocyclopropyl, then R 1 is not H;

or an agrochemically acceptable salt or N-oxide thereof.

4. A compound or salt according to claim 1 of formula (Ia)

wherein

Z 1 is CF(CF 3 )(CF 3 );

R 1 is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl 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;

A is selected from C—H and N;

R 3 is selected from H and CN;

Tis

or an agrochemically acceptable salt or N-oxide thereof.

5. A compound or salt according to claim 1 of formula (Ia)

wherein

Z 1 is CF(CF 3 )(CF 3 );

le is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl 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;

A is selected from C—H and N;

R 3 is selected from H and CN;

T is selected from

or an agrochemically acceptable salt or N-oxide thereof.

6. 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.

7. The composition according to claim 6 , which further comprises one or more other insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

8. A method for controlling and preventing pests, which comprises applying a composition according to claim 6 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy.

9. 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 a composition according to claim 6 .

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

11. A compound selected from:

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,2-pentafluoroethanesulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

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

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

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

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-methyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,2-pentafluoroethanesulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 2-chloro-1,1,2,2-tetrafluoro-ethanesulfonate;

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

5-[4-[4-chloro-3-[cyclopropyl(ethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 2-chloro-1,1,2,2-tetrafluoro-ethanesulfonate;

[5-[4-[4-chloro-3-[cyclopropyl(methyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 2-chloro-1,1,2,2-tetrafluoro-ethanesulfonate;

[5-[4-[4-chloro-3-[cyclopropyl(ethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

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

[5-[4-[4-chloro-3-[cyclopropyl(ethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,2-pentafluoroethanesulfonate;

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

[5-[4-[4-chloro-3-[cyclopropyl(methyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,2-pentafluoroethanesulfonate;

[5-[4-[4-chloro-3-[cyclopropyl(methyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-methyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-methyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 2-chloro-1,1,2,2-tetrafluoro-ethanesulfonate;

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

[5-[4-[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[6-chloro-5-[cyclopropyl(methyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-5-[cyclopropyl(ethyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)-methyl-carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)-ethyl-carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

[5-[4-[6-chloro-5-[cyclopropyl(methyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

[5-[4-[6-chloro-5-[cyclopropyl(ethyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)-methyl-carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

[5-[4-[6-chloro-5-[(1-cyanocyclopropyl)-ethyl-carbamoyl]-3-pyridyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;

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

[5-[5-[4-chloro-3-[cyclopropyl(methyl)carbamoyl]phenyl]isoxazol-3-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[5-[4-chloro-3-[cyclopropyl(ethyl)carbamoyl]phenyl]isoxazol-3-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[5-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]isoxazol-3-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[5-[4-chloro-3-[(1-cyanocyclopropyl)-methyl-carbamoyl]phenyl]isoxazol-3-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[5-[4-chloro-3-[(1-cyanocyclopropyl)-ethyl-carbamoyl]phenyl]isoxazol-3-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

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

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

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

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

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

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

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-ethyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[3-[acetyl-(1-cyanocyclopropyl)carbamoyl]-4-chloro-phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(ethoxymethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(methoxymethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(cyanomethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-prop-2-ynyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-ethoxycarbonyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-methoxycarbonyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-propanoyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

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

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-formyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-[(E)-1,2,3,3,3-pentafluoroprop-1-enyl]carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(2,2-dimethylpropanoyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(2-methylpropanoyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(2-methoxyacetyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[[1-(difluoromethyl)cyclopropyl] carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[[1-(trifluoromethyl)cyclopropyl]carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

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

[5-[4-[4-chloro-3-[[1-(cyanomethyl)cyclopropyl]carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(isopropoxymethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(isopropoxymethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-propyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(2-methoxyethyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate;

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-(3-methoxypropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate; or

[5-[4-[4-chloro-3-[(1-cyanocyclopropyl)-isopropoxycarbonyl-carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate.

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Feb 28, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070362/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2020
From: JEANGUENAT, ANDRÉ; EL QACEMI, MYRIEM; STOLLER, ANDRÉ; BIGOT, AURELIEN; GRIBKOV, DENIS
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 051407/0014 →