Pesticidal compounds

Patent metadata

Field	Value
Publication number	US-12564191-B2
Application number	US-202117920786-A
Country	US
Kind code	B2
Filing date	Apr 23, 2021
Priority date	Apr 28, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

The present application 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 in the claims. The compounds of formula (I), as well as 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 application also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

First claim

We claim:

1 . A compound of the formula I

wherein
A is N or CR A ;
B 1 is N or CR B1 ;
D is N or CR D ;
E is N or CR E ;
wherein at least one of the A, B 1 , E, and D is N; and when A and D are N, B 1 is CR B1 ;
B 2 is N or CR B2 ;
B 3 is N or CR B3 ;
B 4 is N or CR B4 ;
provided that at least one of the B 2 , B 3 , and B 4 is other than N;
R A , R D , R B1 , and R E independently of each other are H, halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, 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, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-NR b R c , O-C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, NH-C 1 -C 6 -alkylene-NR b R c , C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , or S(═O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R B2 , R B3 , and R B4 independently of each other are H, halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, 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, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-NR b R c , O-C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, NH-C 1 -C 6 -alkylene-NR b R c , C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , or S(═O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
Q is —C(R 4 R 5 )—O—, —C(═O)—O—, —S(═O) m —C(R 7 R 8 )—, —N(R 2 )—S(═O) m —, —N(R 2 )—C(R 9 R 10 )—, —C(═O)—C(R 19 R 20 )—, —N(R 2 )—, —N(R 2 )—C(═O)—, —N(R 2 )—C(═S)—, —C(R 13 R 14 )—C(R 15 R 16 )—, —N═C(X)—, —N(R 2 )—C(═NR)—, or —C(R 17 )═C(R 18 )—;
wherein Ar is bound to either side of Q;

m is 0, 1, or 2;
X is H, halogen, SR 7 , OR 8 , or N(R 8 ) 2 ;
R is H, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, or C 3 -C 6 -cycloalkyl, which moieties are unsubstituted or substituted with halogen, OR 8 , N(R 3 ) 2 ;
R 3 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl;
R 2 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which moieties are unsubstituted or substituted with halogen C(═O)—OR a , C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , S(═O) m R e , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 are, identical or different, H, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR a , C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , S(═O) m R e , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
Ar is phenyl or 5- or 6-membered hetaryl or 1,3-benzodioxole, which are unsubstituted or substituted with R Ar , wherein
R Ar is halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, 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, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR a , NR b R c , C 1 -C 6 -alkylene-NR b R c , O—C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, NH—C 1 -C 6 -alkylene-NR b R c , C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , or S(═O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio or —CH 2 -phenyl, wherein phenyl rings are unsubstituted or substituted with R f ;
R 1 is a moiety of formula Y—Z—T—R 11 or Y—Z—T—R 12 ; wherein
Y is —CR ya ═N—, wherein the N is bound to Z;
—NR yc —C(═O)—, wherein C(═O) is bound to Z; or
—NR yc —C(═S)—, wherein C(═S) is bound to Z;

Z is a single bond;
—NR zc —C(═O)—, wherein C(═O) is bound to T;
—NR zc —C(═S)—, wherein C(═S) is bound to T;
—N═C(S—R za )—, wherein T is bound to the carbon atom;
—O—C(═O)—, wherein T is bound to the carbon atom; or
—NR zc —C(S—R za )=, wherein T is bound to the carbon atom;
Provided that when Y is —NR yc —C(═O)— or —NR yc —C(═S)—, then Z is other than a single bond;

T is O, N or N—R T ;
R 11 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, which moieties are unsubstituted or substituted with halogen,
C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , aryl, aryl-carbonyl, aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C 1 -C 4 -alkyl or hetaryloxy-C 1 -C 4 -alkyl, wherein the phenyl and hetaryl rings are unsubstituted or substituted with R g and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl;

R 12 is a radical of the formula A 1 ;

wherein # indicates the point of attachment to T;

R 121 , R 122 , R 123 are, identical or different, H, halogen, C 1 -C 6 -alkyl, 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 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylcarbonlyoxy, C 1 -C 6 -alkenylcarbonlyoxy, C 3 -C 6 -cycloalkylcarbonlyoxy, which moieties are unsubstituted or substituted with halogen, or NR b R c , or one of R 121 , R 122 , R 123 may also be oxo;
R 124 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, or C 2 -C 6 -alkenyloxy, which moieties are unsubstituted or substituted with halogen;
and where

R ya is H, halogen, 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 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR a , C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , C(═O)—R d , SO 2 NR b R c , S(═O) m R e , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R yc , R zc are, identical or different, H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkyl-C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, or C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, which moieties are unsubstituted or substituted with halogen;
R T is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkyl-C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -c

Assignees

• Basf Se

Inventors

• Garza Sanchez Rosario Aleyda
• Narine Arun
• Chaudhuri Rupsha
• Maity Pulakesh

Classifications

• C07D213/75 Primary

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• C07D239/28

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms · CPC title

• A01N47/34

  containing the groups [IMAGE cpc-sch-A01N-0947.gif], e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products · CPC title

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title