Pesticidally active heterocyclic derivatives with sulphur and cyclopropyl containing substituents
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 or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 2 is C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; or
R 2 is cyclopropyl 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, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted 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 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 alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, 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 pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl 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 alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, 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 a five membered, aromatic ring system linked via a nitrogen atom to the ring which contains the substituent A, 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 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, 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; and
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 4 is hydrogen, halogen, cyano, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and
R 5 is C 1 -C 4 alkyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.
2. A compound of formula I according to claim 1 , wherein
R 1 is C 1 -C 4 alkyl;
R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl or cyclopropane, said cyclopropane 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, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, 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 is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted 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 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 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, 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 pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl 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 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, 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 a pyrazolyl- or a triazolyl 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 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl and —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; and
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 4 is hydrogen, halogen, cyano or C 1 -C 4 haloalkyl; and
R 5 is C 1 -C 4 alkyl.
3. A compound of formula I according to claim 1 , wherein
R 1 is C 1 -C 4 alkyl;
R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl;
R 3 is hydrogen, halogen, cyano, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl or C 1 -C 6 haloalkylsulfonyl; or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted 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 phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; or
R 3 is pyrimidinyl or pyridinyl which both can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; or
R 3 is a pyrazolyl- or a triazolyl 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, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; and 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 4 is hydrogen, halogen, cyano or C 1 -C 4 haloalkyl; and
R 5 is C 1 -C 4 alkyl.
4. A compound of formula I according to claim 1 , wherein
R 1 is ethyl or methyl;
R 2 is C 1 -C 6 haloalkyl;
R 3 is hydrogen, halogen, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl or C 1 -C 6 haloalkylsulfonyl; or
R 3 is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; or
R 3 is pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl can be mono- or polysubstituted by substituents selected from the group
consisting of halogen, cyano, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; or
R 3 is a pyrazolyl- or a triazolyl 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, C 1 -C 4 haloalkyl, 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 and C 1 -C 4 alkylsulfonyl; and 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 4 is hydrogen; and
R 5 is C 1 -C 4 alkyl.
5. A compound of formula I according to claim 1 , wherein
R 1 is ethyl or methyl;
R 2 is CF 3 ;
R 3 is hydrogen, halogen, C 1 -C 2 haloalkyl, cyclopropane, trifluoromethylsulfanyl, trifluoromethylsulfinyl or trifluoromethylsulfonyl; or
R 3 is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 2 haloalkyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and C 1 -C 2 alkylsulfanyl; or
R 3 is pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl can be mono- or polysubstituted by substituents selected from the group
consisting of halogen, cyano, C 1 -C 2 haloalkyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and C 1 -C 2 alkylsulfanyl; or
R 3 is a pyrazolyl- or a triazolyl 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, C 1 -C 2 haloalkyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and C 1 -C 2 alkylsulfanyl; and 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 4 is hydrogen; and
R 5 is C 1 -C 4 alkyl.
6. A compound of formula I according to claim 1 , wherein
R 1 is ethyl;
R 2 is CF 3 ;
R 3 is hydrogen, halogen, trifluoromethyl, pentafluoroethyl, cyclopropane, trifluoromethylsulfanyl, trifluoromethylsulfinyl or trifluoromethylsulfonyl; or
R 3 is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and methylsulfanyl; or
R 3 is pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl can be mono- or polysubstituted by substituents selected from the group
consisting of halogen, cyano, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and methylsulfanyl; or
R 3 is a pyrazolyl- or a triazolyl 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, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl and methylsulfanyl; and 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 4 is hydrogen; and
R 5 is methyl.
7. A compound of formula I according to claim 1 ,
wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 2 is CF 3 ;
R 3 is hydrogen, halogen or C 1 -C 4 haloalkyl; or
R 3 is cyclopropane which can be mono-substituted by cyano; or
R 3 is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 2 haloalkyl, C 1 -C 2 halomethoxy, C 1 -C 2 alkoxy and C 1 -C 2 sulfanyl; or
R 3 is pyrimidinyl or pyridinyl linked via a carbon atom to the ring which contains the substituent A, said pyrimidinyl or pyridinyl can be mono- or polysubstituted by substituents selected from the group
consisting of halogen, cyano, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy; or
R 3 is a pyrazolyl- or a triazolyl ring system linked via a nitrogen atom to the ring, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 2 haloalkyl;
R 4 is hydrogen; and
R 5 is methyl.
8. A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
9. A method for controlling pests, which comprises applying a composition according to claim 8 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
10. 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 8 .
11. Plant propagation material treated in accordance with the method described in claim 10 .
12. The compound of claim 1 , wherein R 2 is CF 3 , R 4 is H, and R 5 is methyl.