Azole pesticidal compounds

Patent metadata

Field	Value
Publication number	US-2026055096-A1
Application number	US-202319112314-A
Country	US
Kind code	A1
Filing date	Sep 15, 2023
Priority date	Sep 19, 2022
Publication date	Feb 26, 2026
Grant date	—

Abstract

The invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, wherein the variables are defined according to the description. The compounds of formula (I), the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

First claim

1 . A compound of formula I

wherein
Q is —C(═O)—N(R 5 )— or —N(R 5 )—C(═O)—;
R 5 is H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, phenyl, 5- or 6-membered hetaryl, —CH 2 — phenyl, —CH 2 -5- or -6-membered hetaryl, 1,3-dioxolan-2-ylmethyl, or halogen, wherein the alkyl, cycloalkyl, phenyl and hetaryl moieties are unsubstituted or substituted with halogen or CN;
A is N or CRA;
R A is H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, halogen, CN, or
NR 6 R 7 wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
R 2 is H or C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen, CN, or C 1 -C 6 -alkoxy;
B 1 is N or CR B1 ;
B 2 is N or CR B2 ;
B 3 is N or CR B3 ;
B 4 is CR B4 ;
R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, or C 1 -C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
D is the moiety DA or DB,

R 3 is H, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
R 4 is H, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen, —O—(C═O)—C 1 -C 6 -alkoxy, —O—(C═O)—C 1 -C 6 -alkyl; or CN; or
B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH 2 moieties of the carbocyclic group may be replaced by a carbonyl group, O, or S, wherein the carbocyclic group is unsubstituted or substituted with R h ;
Ar 1 is phenyl or 5- or 6-membered heteroaryl, which are unsubstituted or substituted with R Ar1 , wherein
R Ar1 ; is halogen, SF 5 , NO 2 , OH, CN, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f , C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , NHS(═O) m R e , S(═O) m R e , —N═S(═O)—(C 1 -C 6 -alkyl) 2 , or SO 2 NR b R c ;
R 6 and R 7 are, identical or different, H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, phenyl, —CH 2 -phenyl, 5- or 6-membered heteroaryl, —CH 2 -5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy;
Ar 2 is phenyl or 5- or 6-membered heteroaryl, which are unsubstituted or substituted with R Ar2 , wherein
R Ar2 is halogen, CN, —SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or substituted with halogen or CN, C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c ;
R a , R b , and R c are, identical or different, H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, —C(═O)—C 1 -C 6 -alkyl, wherein the alkyl, alkenyl, and cycloalkyl moieties are unsubstituted or substituted with halogen;
R d is H or C 1 -C 6 -alkyl;
R e is C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen;
m is 0, 1, or 2;
R f is halogen, OH, CN, SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, or C 3 -C 6 -cycloalkoxyx-C 1 -C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or substituted with halogen;
R h is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy;
and N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

2 . The compound of formula I according to claim 1 , wherein D is DB.

3 . The compound of formula I according to claim 1 , wherein D is a group selected from D5 to D7, which are unsubstituted or substituted with 1 or 2 substituents R h

4 . The compound of formula I according to claim 1 selected from the compounds of formula I.1 to I.8, wherein the variables are as defined in claim 1 .

5 . The compound of formula I according to claim 1 , wherein
R 5 is H, C 1 -C 6 -alkyl, or C 1 -C 6 -alkyl-CN; R A is H, CN, or C 1 -C 6 -alkyl; R 2 is H or C 1 -C 6 -alkyl.

6 . The compound of formula\ I according to claim 1 , wherein B 1 is CR B1 , B 2 is CR B2 , and B 3 is CR B3 .

7 . The compound of formula I according to claim 1 , wherein B 1 is N, B 2 is CR B2 , and B 3 is CR B3 .

8 . The compound of formula I according to claim 1 , wherein R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, or C 1 -C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen.

9 . The compound of formula I according to claim 1 , wherein
Ar 1 is phenyl which is unsubstituted or substituted with R Ar1 ; R Ar1 ; is halogen, SF 5 , NO 2 , OH, CN, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f , C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , NHS(═O) m R e , —N═S(═O)—(C 1 -C 6 -alkyl) 2 , SO 2 NR b R c , or S(═O) m R e ; R a , R b , and R c , identical or different, are H, C 1 -C 6 -alkyl, which are unsubstituted or substituted with halogen; R d is H or C 1 -C 6 -alkyl; R e is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; R f is halogen, OH, CN, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1, or 2.

10 . A composition comprising a compound of formula I according to claim 1 , an N-oxide, or an agriculturally acceptable salt thereof, and a further active substance.

11 . A method for combating or controlling an invertebrate pest comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound according to claim 1 .

12 . A method for protecting growing plants from attack or infestation by an invertebrate pest comprising contacting a plant, or soil or water wherein the plant is growing, with a pesti

Assignees

• Basf Se

Inventors

• Chaudhuri Rupsha
• Maity Pulakesh
• Defieber Christian
• Handore Kishor
• Adisechan Ashokkumar
• Winter Christian Harald
• Koerber Karsten
• Wakeham Matthew Charles Linford

Classifications

• A01N47/36

  containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof · CPC title

• A01P5/00

  Nematocides · CPC title

• A01P7/04

  Insecticides · CPC title

• A01P7/02

  Acaricides · CPC title

• A01N47/42

  containing —N=CX2 groups, e.g. isothiourea · CPC title