Pesticidal pyrazole and triazole derivatives

Patent metadata

Field	Value
Publication number	US-2022256857-A1
Application number	US-202017625383-A
Country	US
Kind code	A1
Filing date	Jul 9, 2020
Priority date	Jul 19, 2019
Publication date	Aug 18, 2022
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 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 ;
B 3 is N or CR B3 ;
B 4 is CR B4 ;
R A is 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 ;
R B1 , 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, 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 —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 )—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 B , or N(R 8 ) 2 ;
R s H, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl, alkenyl, and cycloalkyl 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, 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 ;

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, 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 ;

R 6 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,
or R 6 is —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, 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;
—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;

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, 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 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;
provided that when T is O, R 11 is other than C 1 -C 6 -alkyl;

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, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkyl 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, wherein the alkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or substituted with halogen;

and where
R ya is H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, which are unsubstituted or substituted with halogen,
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 -cy

Assignees

• Basf Se

Inventors

• Maity Pulakesh
• Narine Arun
• Chaudhuri Rupsha
• Garza Sanchez Rosario Aleyda
• Sambasivan Sunderraman
• Adisechan Ashokkumar
• Shaikh Rizwan Shabbir

Classifications

• C07H15/00

  Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals · CPC title

• C07D231/40 Primary

  Acylated on said nitrogen atom · CPC title

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• A61K31/553

  having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine · CPC title

• A01N43/56

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