Pesticidal compounds

Patent metadata

Field	Value
Publication number	US-11512054-B2
Application number	US-201816772286-A
Country	US
Kind code	B2
Filing date	Dec 11, 2018
Priority date	Dec 21, 2017
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present 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, formula (I). 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 invention 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 formula I

wherein
A 1 is N or CR A ;
A 2 is N or CR B ;
A 3 is N or CR B1 ;
W is O, S(═O) m , or NR 6 ;
R A , R B and R B1 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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 —N═C(X)—, —N(R 2 )—C(═NR)—, or —N(R 2 )—C(═S)—; wherein Ar is bound to either side of Q;
X is identical or different, H, halogen, SR 7 , OR 8 , N(R 3 ) 2 , —CR 4 ═N(OCH 3 ), CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen; phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R 5 ;
R 5 is halogen, N 3 , OH, CN, NO 2 , —SCN, —SF, 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, C1-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 -cycloalkylthio, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, wherein the alkyl, alkoxy, alkylthio, alkenyl, alkynyl, cycloalkyl, cycloalkoxy and cycloalkylthio moieties are unsubstituted or substituted with halogen, C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-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 ;
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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(O)—OR a , C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-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 is identical or different, H, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen, SR 7 , OR 8 , N(R 3 ) 2 , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R 5 ;
R 4 is 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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 , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R 7 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 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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 , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R 8 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 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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 , phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
R 3 , R 6 are, identical or different, 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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, which are unsubstituted or substituted with R Ar , wherein
R Ar is halogen, N 3 , OH, CN, NO 2 , —SCN, —SF, 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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; or
—NR zc —C(S—R za )═, wherein T is bound to the carbon atom;

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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy 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, arylcarbonyl, 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 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 -cycloalkylc

Assignees

• Basf Se

Inventors

• Chaudhuri Rupsha
• Sambasivan Sunderraman
• Narine Arun
• Adisechan Ashokkumar
• Vyas Devendra

Classifications

• C07D401/12

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

• C07D407/12

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

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• C07D405/12

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

• A01N43/56

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