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 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C i -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 NR 4 and G 2 is C(Y); or

G 1 is C(Y) and G 2 is NR 6 ;

Y is O or S;

G 3 is 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 is hydrogen, 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 7 ,or is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which can be mono-or polysubstituted by R 7 , or

R 4 is C 1 -C 4 alkyl substituted by cyano, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinyl,

C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl or by phenyl which itself can be mono- or polysubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C i -C 4 haloalkyl and C 1 -C 4 alkoxy; or

R 4 is 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 4 alkoxy C 1 -C 4 alkyl C 1 -C 6 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, amine or hydroxyl; or

R 4 is C 2 -C 6 alkenyl substituted by R 11 or C 2 -C 6 alkynyl substituted by R 11 ; or

R 4 is a five- to six-membered, aromatic, partially saturated or fully saturated ring system, 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 can contain 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 5 is hydrogen, 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 7 ,or are C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which can be mono- or polysubstituted by R 7 , or

R 5 is C 1 -C 4 alkyl substituted by cyano, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinyl,

C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl or by phenyl which itself 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 C 1 -C 4 alkoxy; or

R 5 is 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 4 alkoxy C 1 -C 4 alkyl C 1 -C 6 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, amine or hydroxyl; or

R 5 is C 2 -C 6 alkenyl substituted by R 11 or C 2 -C 6 alkynyl substituted by R 11 ; or

R 5 is a five- to six-membered, aromatic, partially saturated or fully saturated ring system, 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 can contain 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 7 is cyano, halogen, C 1 -C 6 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, partially saturated or fully 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, 1 or 2;

m is 1 or 2;

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, 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- to polysubstituted by substituents selected from the group consisting of halogen, 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 witch can be mono- to polysubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl and cyano; and

R 11 is nitro, phenyl, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfonyl or C 1 -C 4 haloalkylsulfinyl;

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-1

wherein the substituents X, A, R 1 , R 2 , R 5 , G 3 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .

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

A is C—H or N;

R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or 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; and

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C2-C4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or —SF 5 , additionally one of R 10a , R 10b , R 10c and R 10d can be oxo.

4. A compound of formula I according to claim 1 , represented by the compounds of formula I-1 a

wherein J is selected from the group consisting of

A is C—H or N;

R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1i -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or 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;

R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or are C 3 -C 6 cycloalkyl which can be mono- or poly substituted by R 7 , or are C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which can be mono- or polysubstituted by R 7 ;

or R 5 is C i -C 4 alkyl substituted by cyano or by phenyl which itself can be mono-or polysubstituted by sub stituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy; or

R 5 is 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 6 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, amine or hydroxyl;

R 7 is cyano, halogen or C 1 -C 2 haloalkyl;

X is S, SO or SO 2 ;

G 3 is 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; and

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl- C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10d oxo.

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

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

6. A compound of formula I-1 according to claim 5 , wherein

A is C—H or N;

R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or 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; and

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl- C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10b can be oxo.

7. A compound of formula I according to claim 1 , represented by the compounds of formula I-2a

wherein J is selected from the group consisting of

A is C—H or N;

R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or 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;

R 4 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or are C 3 -C 6 cycloalkyl which can be mono- or poly substituted by R 7 ; or are C 3 -C 6 cycloalkyl-C i -C 4 alkyl which can be mono- or polysubstituted by R 7 ; or

R 4 is C 1 -C 4 alkyl substituted by cyano or by phenyl which itself 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 C 1 -C 4 alkoxy; or

R 4 is 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 6 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, amine or hydroxyl;

R 7 is cyano, halogen or C 1 -C 2 haloalkyl;

X is S, SO or SO 2 ;

G 3 is 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; and

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl- C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10d can be oxo.

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

wherein J is selected from the group consisting of

wherein

A is CH or N;

R 2 is C 1 -C 2 haloalkyl;

R 4 is C 1 -C 4 alkyl; and

R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, C 1 -C 2 haloalkyl or C 1 -C 2 alkyl.

9. A compound of formula I according to claim 1 , represented by the compounds of formula I-2a

wherein J is selected from the group consisting of

wherein

A is CH or N;

R 2 is trifluoromethyl;

R 4 is methyl or ethyl; and

R 10a , R 10b, R 10c , and R 10d , independently from each other, are hydrogen, trifluoromethyl or methyl.

10. 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 agrochemic ally utilizable salt form, as active ingredient and at least one auxiliary.

11. A method for controlling pests, which comprises applying a composition according to claim 10 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.

12. A method for the protection of seeds from the attack by pests, which comprises treating the seeds or the site, where the seeds are planted, with a composition according to claim 10 .

13. The compound of claim 1 , wherein X is SO or SO 2.

14. The compound of claim 1 , wherein A is N.

15. The compound of claim 1 , wherein G 1 is NR 4 and G 2 is C(Y).

16. The compound of claim 1 , wherein R 5 is not hydrogen.

17. The compound of claim 1 , wherein R 6 is not methyl.