Pesticidally active thiosemicarbazone compounds

Patent metadata

Field	Value
Publication number	US-2026020569-A1
Application number	US-202218718880-A
Country	US
Kind code	A1
Filing date	Dec 13, 2022
Priority date	Dec 16, 2021
Publication date	Jan 22, 2026
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 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

1 . A compound of 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, and 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 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 ;
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 R y independently are selected from H or C 1 -C 6 -alkyl, wherein the alkyl group is unsubstituted or substituted with R f ;
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 f ;
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, aryl-carbonyl, aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -alkyl, heteroaryl, carbonyl-heteroaryl, 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 -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 1 -C 6 -alkylene-CN, phenyl, or —CH 2 — phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;
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 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)—.

5 . The compound of formula I according to claim 1 , wherein Q is —N(R 2 )—C(═O)— or —N═C(X)—.

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

7 . A composition comprising a 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.

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

9 . A method for protecting growing plants from attack or infestation by invertebrate pests, 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 .

10 . A seed comprising a compound according to claim 1 , or enantiomers, diastereomers, or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

11 . (canceled)

12 . A non-therapeutical method for treating or protecting an animal from infestation or infection by invertebrate pests comprising bringing the animal in

Assignees

• Basf Se

Inventors

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

Classifications

• C07D231/12

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

• A01N47/48 Primary

  containing —S—C≡N groups (A01N43/00 - A01N47/38 take precedence) · CPC title

• A01P7/00

  Arthropodicides · 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

• A01N43/56

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