Pesticidally active thiosemicarbazone compounds

Patent metadata

Field	Value
Publication number	US-2025197358-A1
Application number	US-202318838023-A
Country	US
Kind code	A1
Filing date	Feb 14, 2023
Priority date	Feb 17, 2022
Publication date	Jun 19, 2025
Grant date	—

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. 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 such compounds for use in 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

1 . A compound of the formula I

wherein
A is N or CR A ;
B 1 is N or CR B1 ;
B 2 is N or CR B2 ;
R A is H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, alkynyl, cycloalkyl moieties are unsubstituted or substituted with halogen;
R B1 and R B2 independently of each other are H, halogen, OH, CN, —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, wherein the alkyl, alkoxy, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,
C(═O)—OR a , NR b R c ;

Q is —N(R 2 )—C(═O)—, —N(R 2 )—C(═S)—, —N═C(X)—, or —N(R 2 )—C(═NR)—, wherein Ar is bound to either side of Q;
X is N(R 3 ) 2 ;
R is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkynyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl, and cycloalkyl moieties are unsubstituted or substituted with halogen,

R 3 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl; C 3 -C 6 -cycloalkyl;
R 2 is H, C 1 -C 6 -alkyl, 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, wherein the alkyl, alkoxy, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted
or substituted with halogen,
C(═O)—OR a ;
m is 0, 1, or 2;

R 6 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkynyl, and cycloalkyl moieties are unsubstituted or substituted with halogen,
Ar is phenyl or 5- or 6-membered heteroaryl or 1,3-benzodioxole, which are unsubstituted or substituted with R Ar , wherein
R Ar 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 3 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -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 , SO 2 NR b R c , or S(═O) m R e ;
R s is selected from —(CR x R y ) n —O—CO—(OC 1 -C 6 -alkyl) p —Y, —(CR x R y ) n —O—CO—(C 2 -C 6 -alkenyl) q -Y, —(CR x R y ) n —O—CO—NR j R k ,
n is 1 or 2;
p is 0, 1, 2, 3, 4, or 5;
q is 0, 1, or 2;

Y is C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, 5- to 6-membered heterocyclic group, or phenyl, wherein the alkyl, heterocyclic and phenyl groups are unsubstituted or substituted with R f ;
R x and R y independently are selected from H or C 1 -C 6 -alkyl, wherein the alkyl group is unsubstituted or substituted with R 1 ;
R j and R k independently are selected from H or C 1 -C 6 -alkyl, wherein the alkyl group is unsubstituted or substituted with R 1 ;
R n H, C 1 -C 6 -alkyl, wherein the alkyl moiety is unsubstituted or substituted with halogen, C 1 -C 6 -alkylene-CN;
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 , aryl, arylcarbonyl, aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -alkyl, heteroaryl, carbonylheteroaryl, heteroaryl-C 1 -C 4 -alkyl or heteroaryloxy-C 1 -C 4 -alkyl, wherein the phenyl rings are unsubstituted or substituted with R g and wherein the heteroaryl is a 5- or 6-membered monocyclic heteroaryl or a 8-, 9- or 10-membered bicyclic heteroaryl;
R a , R b , and R c 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 -cycloalkylC 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 1 -C 6 -alkylene-CN, phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R 1 ;

R e is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen;
R f 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 -cycloalkoxyx-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 , SO 2 NR b R c , or S(═O) m R e ;

R g is halogen, OH, CN, —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, 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 , SO 2 NR b R c , or S(═O) m R e ;

and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

2 . The compound of formula I according to claim 1 , wherein A is CR A , B 1 is CR B1 , and B 2 is CR B2 .

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

4 . The compound of formula I according to claim 1 , wherein Q is —N(R 2 )—C(═O)— or —N═C(X)—, R 2 and X are as defined in claim 1 and wherein Ar is bound to either side of Q.

5 . The compound of formula I according to claim 1 , wherein R s is —(CR x R y ) n —O—CO—(OC 1 -C 6 -alkyl) p —Y, R x , R y , Y, p and n are as defined in claim 1 .

6 . The compound of formula I according to claim 1 , wherein Ar is phenyl which is unsubstituted or substituted with R Ar .

7 . The compound of formula I according to claim 1 , wherein R 11 is phenyl which is unsubstituted or substituted with R g .

8 . A composition comprising at least one compound of formula I according to claim 1 , an N-oxide, or an agriculturally acceptable salt thereof, and at least one liquid and/or solid carrier.

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

10 . 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 pesticidally effective amount of at least one compound according to claim 1 .

11 . A seed comprising a compound according to claim 1 , the

Assignees

• Basf Se

Inventors

• Maity Pulakesh
• Chaudhuri Rupsha
• Defieber Christian
• Handore Kishor
• Adisechan Ashokkumar
• Winter Christian Harald

Classifications

• A01N47/42

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

• A01P7/04

  Insecticides · CPC title

• C07D231/14

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D231/40 Primary

  Acylated on said nitrogen atom · CPC title

• C07D249/14

  Nitrogen atoms · CPC title