Pesticidally active amide heterocyclic derivatives with sulphur containing substituents

1. A compound of Formula I:

wherein

A is CH or N;

Q is attached to the 3- or 4-position; and is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of 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 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and 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, 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; or

Q is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the group A, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of 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; and said ring system contains 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

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, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of 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 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; 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 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of 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 haloalkylsulfanyl, C 1 -C 4 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; 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, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of 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 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkoxy, —C(O)C 1 -C 4 haloalkyl, C 1 -C 6 alkylsulfanyl, C 1 -C 6 alkylsulfinyl, or C 1 -C 6 alkylsulfonyl;

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; or

R 1 is 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 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;

X 1 is S; or

X 1 is N—R 4 , wherein R 4 is hydrogen or C 1 -C 4 alkyl;

X 2 is N or C—R 5 , wherein R 5 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or cyano;

R 2 is hydrogen, 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 haloalkylsulfanyl, —O(C 1 -C 4 haloalkyl), or —C(O)C 1 -C 4 haloalkyl;

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;

Y is O or S;

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

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

wherein:

Y, R 2 , R 3 , X 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.

3. A compound of Formula I-1 according to claim 2 , wherein Q is selected from the group consisting of J-1 to J-45 wherein the arrow represents the point of attachment of the heterocycle to the radical Q:

wherein each group J-1 to J-45 is mono- di- or trisubstituted with R x ,

wherein each R x is, independently selected from the group consisting of 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 1 according to claim 1 , represented by the Formula 1-2:

wherein:

Y, R 2 , R 3 , X 2 and Q are as defined under formula 1 in claim 1 ;

Xa 2 is S, SO or SO 2 ; and

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

5. A compound of Formula I-2 according to claim 4 , wherein Q is selected from the group consisting of J-1 to J-45 wherein the arrow represents the point of attachment of the heterocycle to the radical Q:

wherein each group J-1 to J-45 is mono- di- or trisubstituted with Rx,

wherein each R x is, independently selected from the group consisting of 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.

6. A compound of Formula 1 according to claim 1 represented by the compounds of Formula Ia-1:

wherein:

A is CH or N;

X 10 is S or SO 2 ;

R 20 is C 1 -C 4 alkyl;

R 21 is C 1 -C 4 haloalkyl;

R 31 is hydrogen or C 1 -C 4 alkyl; and

Q a is selected from the group consisting of the heterocycles:

wherein each group Q a is mono- di- or trisubstituted with Rx,

wherein each R x is, independently selected from the group consisting of 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.

7. A compound of Formula I according to claim 1 represented by the compounds of Formula Ia-2:

wherein

A is CH or N;

X 11 is S or SO 2 ;

R 22 is C 1 -C 4 alkyl;

R 23 is C 1 -C 4 haloalkyl;

R 31 is hydrogen or C 1 -C 4 alkyl; and

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

wherein each R x is, independently selected from the group consisting of 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.

8. A compound of Formula I according to claim 1 represented by the compounds of Formula Ia-3:

wherein:

A is CH or N;

R 24 is C 1 -C 4 haloalkyl;

R 33 is hydrogen or C 1 -C 4 alkyl; and

Q c is selected from the group consisting of the heterocycles:

wherein each R x is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfonyl, and C 1 -C 4 alkylsulfonyl.

9. A compound of formula I according to claim 1 represented by the compounds of Formula I-5:

wherein:

A, Y, R 2 , R 3 , X 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.

10. A compound of formula I according to claim 1 represented by the compounds of Formula Ia-6:

wherein:

A is N or CH;

X 13 is S or SO 2 ;

R 40 is C 1 -C 4 alkyl;

R 41 is C 1 -C 4 haloalkyl;

R 50 is hydrogen or C 1 -C 4 alky; and

Q f is:

wherein J-0a is monosubstituted with R x ,

wherein R x is 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 alkylsulfanyl, —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.

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

wherein:

A is N or CH;

R 42 is C 1 -C 4 haloalkyl;

R 51 is hydrogen or C 1 -C 4 alkyl; and

Q g is:

 wherein R x is hydrogen or C 1 -C 4 haloalkyl.

12. A compound of Formula XXXI-int:

wherein:

R 1 , R 2 , R 3 , X, X 1 , X 2 and A are as defined under Formula I in claim 1 ;

Yb 2 is B(OH) 2 or B (ORb 2 ) 2 , in which Rb 2 is a C 1 -C 6 alkyl; or

Yb2 is:

13. 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.

14. A method for controlling pests, which comprises applying a composition according to claim 13 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 practiced on the human or animal body.