Pesticidal pyrazole and triazole derivatives

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 , 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, or 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,

or R A is 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 , or R A is 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, or 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,

or R B1 , R B2 , R B3 , and R B4 independently of each other are 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 , or R B1 , R B2 , R B3 , and R B4 independently of each other are 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 8 , or N(R 3 ) 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, wherein the alkyl, alkenyl, and cycloalkyl moieties are unsubstituted or substituted with halogen, OR 8 , or N(R 3 ) 2 ;

R 3 is H, C 1 -C 6 -alkyl, or 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,

or R 2 is 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 , or S(═O) m R e , or R 2 is 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,

or 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, 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, C(═O)—R d , SO 2 NR b R c , or S(═O) m R e , or 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, 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,

or R Ar is 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 , or R Ar is 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

YZT-1 to YZT-9, wherein

denotes attachment to the remaining part of the compound;

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,

or R 11 is 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 aryl or hetaryl rings are unsubstituted or substituted with R g and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or an 8-, 9-, or 10-membered bicyclic hetaryl;

R 12 is a radical of the formula A 1 ;

wherein # indicates the point of attachment to oxygen;

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 R 121 , R 122 , R 123 are 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, or C 1 -C 6 -alkoxy, which are unsubstituted or substituted with halogen,

or R ya is 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, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy 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 -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 T is 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 , or S(═O) m R e , or R T is phenyl or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;

R zc together with R T if present, may form C 1 -C 6 -alkylene or a linear C 2 -C 6 -alkenylene group, where in the linear C 1 -C 6 -alkylene and the linear C 2 -C 6 -alkenylene a CH 2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C 1 -C 6 -alkylene and the linear C 2 -C 6 -alkenylene may be unsubstituted or substituted with R h ;

R za is H, 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 4 -alkyl-C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkoxy, or C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or substituted with halogen,

or R za is C 1 -C 6 -alkylene-NR b R c , C 1 -C 6 -alkylene-CN, C(═O)—NR b R c , or C(═O)—R d , or R za is phenyl, phenylcarbonyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;

R za together with R T if present, may form C 1 -C 6 -alkylene or a linear C 2 -C 6 -alkenylene group, where in the linear C 1 -C 6 -alkylene and the linear C 2 -C 6 -alkenylene a CH 2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C 1 -C 6 -alkylene and the linear C 2 -C 6 -alkenylene may be unsubstituted or substituted with R h ;

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, or 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 a , R b and R c are, identical or different, C 1 -C 6 -alkylene-CN, phenyl, or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;

R d 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, or 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 d is 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, or C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen,

or R e is phenyl or —CH 2 -phenyl, wherein the phenyl rings are unsubstituted or substituted with R f ;

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, or 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,

or R f is 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 ;

R g 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, or 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 g is 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 ;

R is halogen, OH, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, or CN;

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 , B 2 is CR B2 , B 3 is CR B3 , and B 4 is CR B4 .

3 . The compound of formula I according to claim 1 , wherein A is N, B 1 is CR B1 , B 2 is CR B2 , B 3 is CR B3 , and B 4 is CR B4 .

4 . The compound of formula I according to claim 1 , wherein A is N, B 1 is CR B1 , B 2 is N, B 3 is CR B3 , B 4 is CR B4 .

5 . The compound of formula I according to claim 1 , wherein A is CR A , B 1 is CR B1 , B 2 is N, B 3 is CR B3 , and B 4 is CR B4 .

6 . The compound of formula I according to claim 1 , wherein A is CR A , B 1 is CR B1 , B 2 is N, B 3 is N, and B 4 is CR B4 .

7 . The compound of formula I according to claim 1 , wherein A is N, B 1 is N, B 2 is CR B2 , B 3 is CR B3 , B 4 is CR B4 .

8 . The compound of formula I according to claim 1 , wherein

Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridyl, which are unsubstituted or substituted with R Ar ;

R Ar is halogen, OH, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, or S—R e ;

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.

9 . A composition, comprising a compound of formula I according to claim 1 , an N-oxide or an agriculturally acceptable salt thereof, and a further pesticidal active substance.

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

11 . 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 .

12 . 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.

13 . A method for treating or protecting an animal from infestation or infection by invertebrate pests comprising bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I according to claim 1 , a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.