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 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 represents N;
Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl; or
Q is C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl; or
Q is C 2 -C 6 alkynyl, or C 2 -C 6 alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 4 alkyl)silyl and phenyl;
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 or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano 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 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 2 is 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 2 is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), or C(O)C 1 -C 4 haloalkyl; or
R 2 is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
X 1 is O, S or NR 3 , wherein R 3 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.
2. A compound of formula I according to claim 1 , represented by the compounds of formula I-10
wherein
R 2 and Q are as defined under formula I in claim 1 ;
Xa 10 is S, SO or SO 2 ; and
Ra 10 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
3. A compound of formula I-10 according to claim 2 , wherein Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or disubstituted by substituents selected from the group consisting of cyano, C 1 -C 4 haloalkyl and halogen; or Q is C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl monosubstituted by substituents selected from the group consisting of C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl; or Q is C 2 -C 6 alkynyl, or C 2 -C 6 alkynyl monosubstituted by substituents selected from the group consisting of tri(C 1 -C 4 alkyl)silyl, phenyl and phenyl which itself can be monosubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.
4. A compound of formula I according to claim 1 represented by the compounds of formula Ia
wherein
X 2 is SO 2 ;
X 3 is N—(C 1 -C 4 alkyl);
R 4 is C 1 -C 4 alkyl;
Q a is C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, or is C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl each mono- or disubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano, C 3 -C 6 cycloalkyl, tri(C 1 -C 4 alkyl)silyl and phenyl, said phenyl can be mono-substituted by halogen or C 1 -C 4 haloalkyl; or Q a is C 3 -C 6 cycloalkenyl which itself can be mono- or di-substituted by C 1 -C 4 alkyl; and
R 6 is C 1 -C 4 haloalkyl.
5. A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
6. A compound of formula I according to claim 1 , wherein Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl.
7. A compound of formula I according to claim 6 , wherein Q is C 3 -C 6 cycloalkyl monosubstituted by cyano.