IP Library › Granted Patent US 11,459,318

Granted Patent B2

US 11,459,318 · App. 16/754,050 · Granted Oct 4, 2022

Pesticidally active pyrrole derivatives

Inventors: Aurelien Bigot (Stein, CH); Myriem El Qacemi (Stein, CH); Denis Gribkov (Münchwilen, CH); André Stoller (Stein, CH)

Assignee: Syngenta Participations AG

C07D413/04 A01N43/56 A01N43/80 C07D401/14 C07D403/04

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Quick Facts

Patent No.: US 11,459,318
App. No.: 16/754,050
Granted: Oct 4, 2022
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 (141)

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 0 -C 3 -alkyl-C 3 -C 7 cycloalkyl, —C(═O)—C 1 -C 6 -alkyl, —C(═O)—O—C 1 -C 6 -alkyl, —C(═O)—N—(C 1 -C 6 -alkyl) 2 , —(C 0 -C 3 )-alkyl-aryl and —(C 0 -C 3 )-alkyl-heteroaryl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C 0 -C 3 -alkyl-C 3 -C 7 cycloalkyl, —C(═O)—C 1 -C 6 -alkyl, —C(═O)—O—C 1 -C 6 -alkyl, —C(═O)—N—(C 1 -C 6 -alkyl) 2 , —(C 0 -C 3 )-alkyl-aryl and —(C 0 -C 3 )-alkyl-heteroaryl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, cyano, C 1 -C 6 -alkoxy and —C(═O)—O—C 1 -C 6 -alkyl;

Q is selected from H, hydroxy, —C(═O)H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C 0 -C 3 -alkyl-C 3 -C 7 cycloalkyl, —C 0 -C 3 -alkyl-C 3 -C 7 heterocycloalkyl, —C 0 -C 3 -alkyl-aryl, —C 0 -C 3 -alkyl-heteroaryl, —NH—(C 1 -C 6 -alkyl), —N—(C 1 -C 6 -alkyl) 2 and —C(═O)N—(C 1 -C 6 -alkyl) 2 , wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C 0 -C 3 -alkyl-C 3 -C 7 cycloalkyl, —C 0 -C 3 -alkyl-C 3 -C 7 heterocycloalkyl, —C 0 -C 3 -alkyl-aryl, —C 0 -C 3 -alkyl-heteroaryl, —NH—(C 1 -C 6 -alkyl), —N—(C 1 -C 6 -alkyl) 2 and —C(═O)N—(C 1 -C 6 -alkyl) 2 is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxyl, nitro, amino, cyano, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, —C(═O)NH 2 , —C(═S)NH 2 , C 3 -C 6 -cycloalkylcarbamoyl and phenyl;

W is O or S;

L is selected from

wherein

indicates the bond to the group

T is selected from

wherein

indicates the bond to the L group;

R 2 is H, Cl or Br;

R 3 is selected from Cl, Br and CN;

Z 1 is selected from H, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl wherein C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 9 substituents independently selected from halogen, cyano and C 1 -C 6 -alkoxy;

Z 2 and Z 4 are independently selected from H, halogen, cyano, nitro, C 1 -C 6 -alkyl, —C(═S)—NH 2 , —C(═S)—NH(C 1 -C 6 -alkyl), —C(═S)—N(C 1 -C 6 -alkyl) 2 , C 3 -C 7 heterocycloalkyl, C 3 -C 6 -cycloalkyl, —S—C 1 -C 6 -alkyl, —S—C 3 -C 5 -cycloalkyl, —SO—C 1 -C 6 -alkyl, —SO—C 3 -C 5 -cycloalkyl, —SO 2 —C 1 -C 6 -alkyl, —SO 2 —C 3 -C 5 -cycloalkyl, —SO 2 —O—C 1 -C 6 -alkyl, —SO 2 —O—C 3 -C 5 -cycloalkyl, —C 0 -C 3 -alkyl-aryl, —C 0 -C 3 -alkyl-heteroaryl, wherein each of —C(═S)—NH(C 1 -C 6 -alkyl), —C(═S)—N(C 1 -C 6 -alkyl) 2 , C 1 -C 6 -alkyl, C 3 -C 7 heterocycloalkyl, C 3 -C 6 -cycloalkyl, —S—C 1 -C 6 -alkyl, —S—C 3 -C 5 -cycloalkyl, —SO—C 1 -C 6 -alkyl, —SO—C 3 -C 5 -cycloalkyl, —SO 2 —C 1 -C 6 -alkyl, —SO 2 —C 3 -C 5 -cycloalkyl, —SO 2 —O—C 1 -C 6 -alkyl, —SO 2 —O—C 3 -C 5 -cycloalkyl, —C 0 -C 3 -alkyl-aryl and —C 0 -C 3 -alkyl-heteroaryl is unsubstituted or substituted with 1 to 9 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl and hydroxycarbonyl;

Z 3 is selected from H and halogen;

or an agrochemically acceptable salt thereof.

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

wherein

indicates the bond to the L group;

R 3 is selected from Cl, Br and CN.

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

wherein

indicates the bond to the L group;

R 2 is H, Cl or Br.

4. The compound or salt according to claim 1 , wherein T is

wherein

indicates the bond to the L group;

R 2 is H, Cl or Br.

5. The compound or salt according to claim 1 , wherein L is

wherein

indicates the bond to the group

6. A compound or salt according to claim 1 , wherein L is

wherein

indicates the bond to the group

7. The compound or salt according to claim 1 , wherein R 1 is selected from H and C 1 -C 6 -alkyl.

8. The compound or salt according to claim 1 , wherein Q is C 3 -C 6 -cycloalkyl which is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen and cyano.

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

Z 1 is C 1 -C 6 -alkyl wherein C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 7 halogen substituents;

Z 2 is selected from C 1 -C 6 -alkyl which is substituted with 1 to 7 halogen substituents;

Z 3 is H or bromo;

Z 4 is selected from H, halogen, nitro, cyano, methyl, trifluoromethyl and —C(═S)—NH 2 .

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

Z 1 is selected from methyl, —CH 2 CN, —CH 2 F and —CH 2 —O—CH 3 ;

Z 2 is selected from —CF(CF 3 )(CF 3 );

Z 3 is H or bromo;

Z 4 is selected from H, halogen, nitro, cyano, methyl, trifluoromethyl and —C(═S)—NH 2 .

11. 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.

12. The composition according to claim 11 , which further comprises one or more additional insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

13. A method for controlling insect, acarine, mollusc, and nematode pests, which comprises applying a composition according to claim 11 to the pests or their environment with the proviso that treating human or animal bodies by surgery or therapy and/or diagnostic methods practiced on human or animal bodies are excluded.

14. A method for the protection of plant propagation material from attack by insect, acarine, mollusc, and nematode pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 11 .

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

16. A compound selected from:

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

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

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

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

2-chloro-N-(1-cyanocyclopropyl)-5-[3-[1-methyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]isoxazol-5-yl]benzamide;

5-[3-[3-bromo-1-methyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]isoxazol-5-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

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

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

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

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

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[1,3-dimethyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzamide;

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

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

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

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

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[3,4-dibromo-1-methyl-5-(trifluoromethylsulfanyl)pyrrol-2-yl]pyrazol-4-yl]benzamide;

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

5-[1-[3-chloro-1-methyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]-2-cyano-N-cyclopropyl-thiophene-3-carboxamide;

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

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

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

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

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

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

5-[1-[3-bromo-1-tert-butyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide;

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

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

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

2-chloro-5-[1-[3-chloro-1-(fluoromethyl)-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)benzamide;

2-chloro-5-[1-[3-chloro-5-[1-(3,5-dichlorophenyl)-1,2,2,2-tetrafluoro-ethyl]-1-methyl-pyrrol-2-yl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)benzamide;

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

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

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

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

N-acetyl-2-chloro-N-(1-cyano-1-methyl-ethyl)-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzamide;

N-acetyl-2-chloro-N-(1-cyanocyclopropyl)-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyano-1-methyl-ethyl)-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]-N-methyl-benzamide;

methyl N-[2-chloro-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzoyl]-N-(1-cyanocyclopropyl)carbamate;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]benzamide;

2-chloro-N-(1-cyanocyclopropyl)-5-[1-[3,4-dibromo-1-cyclopropyl-5-(trifluoromethylsulfanyl)pyrrol-2-yl]pyrazol-4-yl]benzamide; and

5-[1-[3-bromo-1-cyclopropyl-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]pyrrol-2-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide.

17. The compound of claim 16 , wherein the compound is selected from: