Amidoacetonitrile derivatives

1. A compound of formula I

wherein

X signifies Cl, Br or CF 3 ;

Y signifies a single bond, O, S, S(O) or S(O) 2 ; and

W signifies O or S.

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

3. A compound of formula Ia,

wherein Y is a single bond; and X signifies Cl, Br or CF 3 .

4. A compound of formula Ia according to claim 3 , wherein X signifies Cl or CF 3 .

5. A compound of formula Ia according to claim 3 , wherein X signifies CF 3 .

6. A compound of formula Ia,

wherein Y is O; and X signifies Cl, Br or CF 3 .

7. A compound of formula Ia according to claim 6 , wherein X signifies Cl or CF 3 .

8. A compound of formula Ia according to claim 6 , wherein X signifies CF 3 .

9. A compound of formula Ia,

wherein Y is S, S(O) or S(O 2 ); and X signifies Cl, Br or CF 3 .

10. A compound of formula Ia according to claim 9 , wherein X signifies Cl or CF 3 .

11. A compound of formula Ia according to claim 9 , wherein X signifies CF 3 .

12. A compound of formula Ia according to claim 3 , selected from the group consisting of

N-[1-cyano-1-methyl-2-(4-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylbenzamide; and

N-[1-cyano-1-methyl-2-(5-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylbenzamide.

13. A compound of formula Ia according to claim 6 , selected from the group consisting of

N-[1-cyano-1-methyl-2-(4-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethoxybenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethoxybenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethoxybenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethoxybenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethoxybenzamide; and

N-[1-cyano-1-methyl-2-(5-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethoxybenzamide.

14. A compound of formula Ia according to claim 9 , selected from the group consisting of

N-[1-cyano-1-methyl-2-(4-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsulfanylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsulfanylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylsufanylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsulfanylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsulfanylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trfluoromethylsulfanylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsulfinylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsulfinylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylsufinylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsufinylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsufinylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylsufinylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsulfonylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsufonylbenzamide;

N-[1-cyano-1-methyl-2-(4-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylsufonylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-chlorophenoxy)-ethyl]-4-trifluoromethylsufonylbenzamide;

N-[1-cyano-1-methyl-2-(5-cyano-2-bromophenoxy)-ethyl]-4-trifluoromethylsufonylbenzamide; and

N-[1-cyano-1-methyl-2-(5-cyano-2-trifluoromethylphenoxy)-ethyl]-4-trifluoromethylsufonylbenzamide.

15. A method for the preparation of compounds of formula I, respectively in free form or in salt form, according to claim 1 , whereby a compound of formula II

which is known or may be produced analogously to corresponding known compounds, and wherein Y is a single bond, is reacted with a compound of formula III

which is known or may be prepared analogously to corresponding known compounds, and wherein X is defined as given for formula I and Q is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I, where W is O, obtainable according to the presented method or in another way, respectively in free form or in salt form, is either converted to a compound of formula I, where W is S, e. g. by reaction with P 4 S 10 , or into another compound of formula I, a mixture of isomers obtainable according to the presented method is separated and the desired isomer isolated and/or a free compound of formula I obtainable according to the presented method is converted into a salt or a salt of a compound of formula I obtainable according to the presented method is converted into the free compound of formula I or into another salt.

16. A method for the preparation of compounds of formula Ia, respectively in free form or in salt form, according to claim 6 , whereby a compound of formula II,

which is known or may be produced analogously to corresponding known compounds, and wherein Y is O, is reacted with a compound of formula III,

which is known or may be prepared analogously to corresponding known compounds, and wherein X is defined as Cl, Br or CF 3 and Q is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula Ia obtainable according to the presented method or in another way, respectively in free form or in salt form, is converted into another compound of formula Ia, a mixture of isomers obtainable according to the presented method is separated and the desired isomer isolated and/or a free compound of formula Ia obtainable according to the presented method is converted into a salt or a salt of a compound of formula Ia obtainable according to the presented method is converted into the free compound of formula Ia or into another salt.

17. A method for the preparation of compounds of formula Ia, respectively in free form or in salt form, according to claim 9 , whereby a compound of formula II,

which is known or may be produced analogously to corresponding known compounds, and wherein Y is S, S(O) or S(O 2 ), is reacted with a compound of formula III,

18. A method of controlling parasites comprising applying to said parasites or its habitat a parasiticidal effective amount of at least one compound of formula I of claim 1 .

19. The method of claim 18 wherein said parasiticidal effective amount of said at least one compound of formula I of claim 1 is administered to an animal host of said parasite

20. The method of claim 19 whereby said at least one compound of formula I of claim 1 is administered to said animal host topically, perorally, parenterally, or subcutaneously.

21. The method of claim 19 whereby said compound is in a formulation consisting of the group of pour-on, spot-on, tablet, chewie, powder, boli, capsules, suspension, emulsion, solution, injectable, water-additive, and food-additive.

22. The method of claim 19 wherein said parasites are endo-parasites.

23. The method of claim 22 wherein said endo-parasites are helminthes.