Pesticidally active heterocyclic derivatives with sulphur containing substituents
View Patent ↗Compounds of formula I, wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.
1. A compound of formula I,
wherein
A is CH, N or CR 7 ; wherein R 7 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano, nitro or halogen;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl; or
R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl; or
R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;
R 2a and R 2b are, independently from each other, hydrogen, halogen, cyano, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or
R 2a and R 2b are, independently from each other, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, or —C(O)(C 1 -C 4 haloalkyl); or
R 2a and R 2b are, independently from each other, C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl;
R 3 is hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, or
R 3 is C 3 -C 6 cycloalkyl which is mono- or di-substituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and cyano; or
R 3 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl; or
R 3 is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, nitro, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, and —C(O)C 1 -C 4 haloalkyl; or
R 3 is C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkoxy,
—C(O)C 1 -C 4 haloalkyl, C 1 -C 6 alkylsulfanyl, C 1 -C 6 alkylsulfinyl, or C 1 -C 6 alkylsulfonyl; or
R 3 is pyrimidinyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, nitro, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or
R 3 is pyridinyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, nitro, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, or C 1 -C 4 alkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or
R 3 is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the substituent G 3 , said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, nitro, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; said ring system contains 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur; where said ring system may not contain more than one oxygen atom and not more than one sulfur atom;
R 6 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or cyano;
G 1 is CR 4 , wherein R 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano or halogen;
G 2 is N or CR 5 , wherein R 5 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano, nitro or halogen;
G 3 is N or CR 5 , wherein R 5 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or cyano;
or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.
2. A compound according to claim 1 represented by the compounds of formula I-1
wherein X, G 1 , G 2 , R 1 and R 2a are as defined in claim 1 ; R 3 is hydrogen, halogen or C 1 -C 4 haloalkyl.
3. A compound according to claim 1 represented by the compounds of formula I-2
wherein X, G 1 , G 2 , R 1 and R 2a are as defined in claim 1 ; R 3 is hydrogen, halogen or C 1 -C 4 haloalkyl.
4. A compound according to claim 1 represented by the compounds of formula I-3a
wherein
X is S, SO or SO 2 ; R 2a is C 1 -C 4 haloalkyl or halogen; R 3 is hydrogen, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, or is phenyl which can be monosubstituted by halogen or C 1 -C 4 haloalkyl;
G 1 is CR 4 , wherein R 4 is hydrogen, C 1 -C 4 alkyl, cyano or halogen; G 2 is CH or N; and
A is CH or N.
5. A compound according to claim 1 represented by the compounds of formula I-3
wherein
X is S, SO or SO 2 ;
R 3 is hydrogen, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl or phenyl which can be monosubstituted by halogen or C 1 -C 4 haloalkyl;
G 1 is CR 4 , wherein R 4 is hydrogen, C 1 -C 4 alkyl, cyano or halogen;
G 2 is CH or N; and
A is CH or N.
6. A pesticidal composition, which comprises at least one compound according to claim 1 in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
7. A method for controlling agricultural pests, which comprises applying a composition according to claim 6 to the pests or their environment.
8. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 6 .