Pesticidally active tetracyclic heterocyclic derivatives with sulphur containing substituents
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-1,
wherein
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;
Q is selected from the group consisting of
wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 halo alkyl, 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 R 001 is hydrogen or C 1 -C 2 alkyl;
Xa 1 is S, SO or SO 2 ; and
Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
2. A compound of formula I-2
wherein
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;
Q is selected from the group consisting of
wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 halo alkyl, 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;
Xa 2 is S, SO or SO 2 ; and
Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
3. A compound of formula Ia-2
wherein
A is CH or N;
X 4 is SO 2 ;
X 5 is N—(C1-C4alkyl);
R 7 is C 1 -C 4 alkyl;
R 8 is C 1 -C 4 haloalkyl; and
Q b is selected from the group consisting of
wherein
each Rx is independently selected from hydrogen, halogen, cyano, 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.
4. A compound of formula Ia-3
wherein
A is CH or N;
R 9 is C 1 -C 4 haloalkyl;
R 10 is C 1 -C 4 alkyl; and
Qc is selected from the group consisting of
wherein Rx is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy.
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 method for controlling arthropods, which comprises applying an effective amount of a composition according to claim 5 to the arthropods or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.
7. A method for the protection of plant propagation material from the attack by arthropods, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a composition according to claim 5 .
8. Plant propagation material treated in accordance with the method described in claim 6 .
9. The method of claim 6 , wherein the arthropods are insects.
10. The method of claim 6 , wherein the arthropods are from the order Acarina.
11. The method of claim 7 , wherein the arthropods are insects.
12. The method of claim 7 , wherein the arthropods are from the order Acarina.