Pesticidally active pryazole derivatives

Patent metadata

Field	Value
Publication number	US-10874104-B2
Application number	US-201715999052-A
Country	US
Kind code	B2
Filing date	Feb 16, 2017
Priority date	Feb 18, 2016
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

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.

First claim

The invention claimed is:

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 3 -C 6 alkenyl, C 3 -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 5 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 2 -C 6 alkenyl, C 2 -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 5 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 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;
Z 1 is selected from C 1 -C 6 -alkyl, C 3 -C 7 heterocycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, wherein each of C 1 -C 6 -alkyl, C 3 -C 7 heterocycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl 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;
U is —OCHF 2 ;
Z 3 is selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -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. A compound according to claim 1 , wherein T is

wherein

indicates the bond to the pyrazole group.

3. A compound according to claim 1 , wherein Z 1 is selected from 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-chloro-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, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-bromocyclopropyl, 1-cyano-cyclopropyl, 1-trifluoromethyl-cyclopropyl, cyclobutyl and 2,2-difluoro-1-methyl-cyclopropyl.

4. A compound according to claim 1 , wherein Z 1 is —CF 2 CF 3 .

5. A compound according to claim 1 , wherein Z 3 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethenyl, 1-propenyl, 1-propinyl, cyclopropyl, 1-butinyl, 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.

6. A compound according to claim 1 , wherein Z 3 is methyl.

7. A compound according to claim 1 , wherein:
R 1 is H or C 1 -C 6 alkyl;
Q is cyclopropyl or 1-cyanocyclopropyl;
T is

R 7a and R 8a are hydrogen;
W is O;
A 1 is CH;
A 2 is CH or N;
A 3 is CR 4 ;
A 4 is CH;
R 4 is selected from H, halogen, cyano, and C 1 -C 6 alkyl;
Z 1 is C 1 -C 6 -haloalkyl; and
Z 3 is H or C 1 -C 6 alkyl.

8. A compound according to claim 7 , wherein T is T47.

9. A compound according to claim 8 , wherein:
R 1 is C 1 -C 6 alkyl;
R 4 is selected from H, halogen, and cyano; and
Z 3 is C 1 -C 6 alkyl.

10. A compound according to claim 9 , where

Assignees

• Syngenta Participations Ag

Inventors

• JEANGUENAT ANDRé
• Pitterna Thomas
• El Qacemi Myriem
• STOLLER ANDRé
• Mondiere Régis Jean Georges
• Bigot Aurelien
• Edmunds Andrew
• Gribkov Denis

Classifications

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• C07D231/44

  Oxygen and nitrogen or sulfur and nitrogen atoms · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title