Pesticidally active tetracyclic derivatives with sulfur containing substituents

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, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl; or is 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 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;

R 2 is hydrogen, halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), —SF 5 , —C(O)C 1 -C 4 haloalkyl, cyano, C 1 -C 6 haloalkyl or is C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or is 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;

G 1 is N or CR 4 ;

G 2 is N or CR 5 ;

G 3 is O, S or NR 6 ;

R 6 is C 1 -C 4 alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen and C 1 -C 2 alkylsulfinyl;

R 4 and R 5 , independently from each other, are hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or are C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by R 8 ; or are C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which can be mono- or polysubstituted by R 9 ; or

R 4 and R 5 , independently from each other, are C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl or hydroxyl;

R 8 and R 9 , independently from each other, are halogen, nitro, cyano, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

L 1 , L 2 , L 3 and L 4 form together with the two carbon atoms to which L 1 and L 4 are attached, an aromatic or partially saturated carbocyclic or heterocyclic ring system;

wherein

L 1 is nitrogen, S(O)n, oxygen, N—R 10a or C(R 10a ) m ;

L 2 is nitrogen, S(O)n, oxygen, N—R 10b or C(R 10b ) m ;

L 3 is nitrogen, S(O)n, oxygen, N—R 10c , or C(R 10c ) m ;

L 4 is nitrogen, S(O)n, oxygen, a direct bond, N—R 10d or C(R 10d ) m ; with the provisos that no more than 2 substituents selected from L 1 , L 2 , L 3 and L 4 can be oxygen or sulfur;

and if two L groups are oxygen, they are not adjacent to each other; and no more than three L groups can be nitrogen;

n is 0 to 2;

m is 1 or 2;

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, amino, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 haloalkoxycarbonyl, (C 1 -C 6 alkyl)NH, (C 1 -C 6 alkyl) 2 N, (C 1 -C 6 cycloalkyl)NH, (C 1 -C 6 cycloalkyl) 2 N, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 cycloalkylcarbonylamino or —SF 5 ;

additionally one of R 10a , R 10b , R 10c and R 10d can be oxo; or

R 10a , R 10b , R 10c , and R 10d , independently from each other, are C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 4 haloalkyl, C 1 -C 4 alkyl and cyano; or

R 10a , R 10b , R 10c , and R 10d , independently from each other, are phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and cyano; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

2. The compound of claim 1 , represented by the compounds of formula I-1

wherein the substituents X, A, R 1 , R 2 , R 6 , G 3 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .

3. The compound of claim 1 , represented by the compounds of formula I-2

wherein the substituents X, A, R 1 , R 2 , R 6 , G 3 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .

4. The compound of claim 1 , represented by the compounds of formula I-3

wherein the substituents X, A, R 1 , R 2 , R 6 , G 3 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .

5. The compound of claim 1 , represented by the compounds of formula I-4

wherein the substituents X, A, R 1 , R 2 , R 6 , G 3 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .

6. The compound of claim 1 , represented by the compounds of formula I-5a

wherein

G 1 is N or CH;

G 2 is N or CH;

R 2 is C 1 -C 4 haloalkyl, C 1 -C 4 halosulfanyl or C 1 -C 4 halosulfinyl;

A is N or CH;

R 6 is C 1 -C 4 alkyl;

X is S or SO 2 ;

R 1 is C 1 -C 4 alkyl; and

Ja is selected from the group consisting of

wherein R 10a , R 10b , R 10c , and R 10d , independently from each other, are selected from the group consisting of hydrogen, halogen, cyano, cyclopropyl, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

7. 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.

8. A method for controlling pests, which comprises applying the composition according to claim 7 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.

9. A method for 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 7 .

10. The plant propagation material treated in accordance with the method described in claim 9 .