IP Library Granted Patent US 11,589,585
Granted Patent B2
US 11,589,585 · App. 17/375,490 · Granted Feb 28, 2023

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 11,589,585
App. No.
17/375,490
Granted
Feb 28, 2023
Kind
B2
Abstract

A compound of formula (II) or formula (III) As defined herein.

Claims (53)

1. A compound of formula (II) or formula (III)

wherein

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;

or an agrochemically acceptable salt or N-oxide thereof.

2. The compound or salt according to claim 1 wherein the formula is formula (II).

3. The compound or salt according to claim 2 wherein

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;

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.

4. The compound or salt according to claim 2 wherein

R 2 is Cl;

A is selected from C—H and N; and

T is

5. The compound or salt according to claim 2 wherein

R 2 is Cl;

A is selected from C—H and N; and

T is selected from

6. The compound or salt according to claim 1 wherein the formula is formula (III).

7. The compound or salt according to claim 6 wherein

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 cyclopropyl or 1-cyanocyclopropyl, then R 1 is not H.

8. The compound or salt according to claim 6 wherein

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;

R 2 is Cl;

A is selected from C—H and N;

Q is

R 3 is selected from H and CN; and

T is

9. The compound or salt according to claim 5 wherein

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;

R 2 is Cl;

A is selected from C—H and N;

Q is

R 3 is selected from H and CN; and

T is selected from

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 070362/0665 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2023
From: JEANGUENAT, ANDRÉ; EL QACEMI, MYRIEM; STOLLER, ANDRÉ; BIGOT, AURELIEN; GRIBKOV, DENIS
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 062329/0671 →