Pesticidally active pyrrole derivatives

Patent metadata

Field	Value
Publication number	US-11384074-B2
Application number	US-201816754016-A
Country	US
Kind code	B2
Filing date	Oct 4, 2018
Priority date	Oct 6, 2017
Publication date	Jul 12, 2022
Grant date	Jul 12, 2022

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

What is 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 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 and C 1 -C 6 -alkyl wherein C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 9 substituents independently selected from halogen, cyano and C 1 -C 6 -alkoxy;
Z 2 is selected from H and halogen;
Z 3 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;
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 or Cl.

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

wherein

 indicates the bond to the L group;
R 2 is H or Cl.

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, methyl and ethyl.

8. The compound or salt according to claim 1 , wherein Q is selected from 1-cyano-cyclopropyl and cyclopropyl.

9. 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 H or chloro;
Z 3 is selected from H, CF(CF 3 )(CF 3 ), —CF 3 and —CF 2 CF 3 ;
Z 4 is selected from H, CF(CF 3 )(CF 3 ), halogen, trifluoromethyl and —CF 2 CF 3 .

10. 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.

11. The composition according to claim 10 , which further comprises one or more additional insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

12. A method for controlling insect, acarine, mollusc, and nematode pests, which comprises applying a composition according to claim 10 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 the human or animal bodies are excluded.

13. 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 10 .

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

15. A compound selected from the group consisting of:
2-cyano-N-cyclopropyl-5-[1-[1-methyl-4-(1,1,2,2,2-pentafluoroethyl)-3-(trif

Assignees

• Syngenta Participations Ag

Inventors

• Bigot Aurelien
• El Qacemi Myriem
• Gribkov Denis
• STOLLER ANDRé

Classifications

• C07D403/04 Primary

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

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D409/14 Primary

  containing three or more hetero rings · CPC title

• C07D413/04

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

• A01N43/56

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