Pesticidally active heterocyclic derivatives with sulphur containing substituents

1. A compound of formula I,

wherein

A represents CH or N;

Q is a five- to ten-membered monocyclic or fused bicyclic heterocyclic ring system which can be aromatic, partially saturated or fully saturated and which contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five- to ten-membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, oxo, OH, NH 2 , C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 halo-alkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino;

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; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

2. A compound of formula I according to claim 1 , wherein

Q is selected from the group consisting of

wherein each group J-1 to J-56 is mono- di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, and C 1 -C 6 di-alkylamino.

3. A compound of formula I according to claim 1 , represented by the compounds of formula

I-1

wherein

R 2 and Q are as defined under formula I in claim 1 ;

Xa 1 is S, SO or SO 2 ; and

Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

4. A compound of formula I-1 according to claim 3 , wherein

Q is selected from the group consisting of the heterocycles

wherein Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino.

5. A compound of formula I according to claim 1 , represented by the compounds of formula

I-2

wherein

R 2 and Q are as defined under formula I in claim 1 ;

Xa 2 is S, SO or SO 2 ; and

Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

6. A compound of formula I-2 according to claim 5 , wherein

Q is selected from the group consisting of the heterocycles

wherein Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, and C 1 -C 6 di-alkylamino.

7. A compound of formula I according to claim 1 represented by the compounds of formula Ia-1

wherein

X 2 is S or SO 2 ;

X 3 is N—(C 1 -C 4 alkyl);

R 4 is C 1 -C 4 alkyl;

R 6 is C 1 -C 4 haloalkyl; and

Q a is selected from the group consisting of the heterocycles

wherein each preferred group Q a is mono- di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino.

8. A compound of formula I according to claim 1 represented by the compounds of formula Ia-2

wherein

X 4 is SO 2 ;

X 5 is N—(C 1 -C 4 alkyl);

R 7 is C 1 -C 4 alkyl;

R 8 is C 1 -C 4 haloalkyl; and

Q b is preferably selected from the group consisting of the heterocycles

wherein each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino.

9. A compound of formula I according to claim 1 , represented by the compounds of formula Ia-3

wherein

R 9 is C 1 -C 4 haloalkyl;

R 10 is C 1 -C 4 alkyl; and

Qc is selected from

wherein

each Rx is, independently selected from the group consisting of hydrogen, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 haloalkylcarbonylamino, halogen, amino, cyano, C 1 -C 6 alkylsulfanyl and phenyl, said phenyl can be substituted by halogen.

10. A compound of formula Ia-3 according to claim 9 ,

wherein

R 9 is C 1 -C 4 haloalkyl;

R 10 is C 1 -C 4 alkyl; and

Qc is

wherein

Rx is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or halogen.

11. 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.