Aminoacetonitrile derivatives and their use for controlling parasites

Abstract

The invention relates to compounds of the general formula in which R 1 , R 2 , X, Ar 1 and Ar 2 are as defined in claim 1 , and to any enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are particularly suitable for controlling parasites in warm-blooded animals.

1 - 33 . (canceled)  
   
   
       34 . A method for the preparation of a compound of formula II  
     
       
         
         
             
             
         
       
     
     which is known or can be prepared by analogy to relevant known compounds and in which Ar 2  is unsubstituted or mono- or polysubstituted phenyl, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, halO-C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylamino, C 3 -C 6 cycloalkylthio, C 2 -C 6 alkenyloxy, halo-C 2 -C 6 alkenyloxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyloxy, halo-C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo-C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenylthio, halo-C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, halo-C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, halo-C 2 -C 6 alkenylsulfonyl, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfonylamino, halo-C 1 -C 6 alkylsufonylamino, C 1 -C 6 alkylcarbonyl, halo-C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl and di-C 1 -C 6 alkylaminocarbonyl; unsubstituted or mono- or polysubstituted phenylamino; unsubstituted or mono- or polysubstituted phenylcarbonyl; unsubstituted or mono- or polysubstituted phenylmethoxymino; unsubstituted or mono- or polysubstituted phenylhydroxymethyl; unsubstituted or mono- or polysubstituted 1-phenyl-1-hydroxyethyl; unsubstituted or mono- or polysubstituted phenylchloromethyl; unsubstituted or mono- or polysubstituted phenylcyanomethyl; unsubstituted or mono- or polysubstituted phenyl, in which the substituents in each case can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsufinyl, C 1 -C 6 alkylsulfonyl and halo-C 1 -C 6 alkylsulfonyl; unsubstituted or mono- or polysubstituted phenoxy, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl and halo-C 1 -C 6 alkylsulfonyl; unsubstituted or mono- or polysubstituted phenylacetylenyl, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsufinyl, C 1 -C 6 alkylsulfonyl and halo-C 1 -C 6 alkylsulfonyl; and unsubstituted or mono- or polysubstituted pyridyloxy, in which the substituents can be independent of one another and are chosen from the group consisting of substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl and halo-C 1 -C 6 alkylsulfonyl; 
 unsubstituted or mono- or polysubstituted hetaryl, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, halo-C 2 -C 6 alkenyloxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 2 -C 6 alkenylthio, halo-C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, halo-C 2 -C 6 alkenylsulfinyl, C 1 -C 6 alkylsulfonyl, halo-C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenylsulfonyl, halo-C 2 -C 6 alkenylsulfonyl, C 1 -C 6 alkylamino and di-C 1 -C 6 alkylamino; or  
 unsubstituted or mono- or polysubstituted naphthyl or quinolyl, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, halo-C 2 -C 6 alkenyloxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 2 -C 6 alkenylthio, halo-C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, halo-C 2 -C 6 alkenylsulfinyl, C 1 -C 6 alkylsulfonyl, halo-C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenylsulfonyl, halo-C 2 -C 6 alkenylsulfonyl, C 1 -C 6 alkylamino and di-C 1 -C 6 alkylamino;  
 R 1  is hydrogen, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, allyl or C 1 -C 6 alkoxymethyl;  
 R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  are either, independently of one another, hydrogen, halogen, unsubstituted or mono- or polyhalogenated C 1 -C 6 alkyl, unsubstituted or mono- or polyhalogenated C 2 -C 6 alkenyl, unsubstituted or mono- or polyhalogenated C 2 -C 6 alkynyl; unsubstituted or mono- or polysubstituted C 1 -C 6 alkoxy, unsubstituted or mono- or polysubstituted halo-C 1 -C 6 alkoxy, unsubstituted or mono- or polysubstituted C 3 -C 6 cycloalkyl, in which the substituents in each case can be independent of one another and are chosen from the group consisting of halogen and C 1 -C 6 alkyl; or unsubstituted or mono- or polysubstituted phenyl, in which the substituents can be independent of one another and are chosen from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo-C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo-C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo-C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylamino or di-C 1 -C 6 alkylamino;  
 or R 2  and R 3  are jointly C 2 -C 6 alkylene; and  
 X is C(R 3 )(R 4 )—C(R 5 )(R 6 ) or C(R 7 )═C(R 8 ), in each case in the free form or in the salt form, which comprises the reaction of a compound of the formula IV  
                     
 which is known or can be prepared by analogy to relevant known compounds and in which R 2 , X and Ar 2  are as defined above, with an inorganic or organic cyanide and a compound of the formula R 1 —NH 2 , which is known or can be prepared by analogy to relevant known compounds and in which R 1  is as defined as above, and in each case, if desired, the conversion of a compound of the formula II obtainable according to the process or in another way, in each case in the free form or in the salt form, to another compound of the formula II, the separation of a mixture of isomers obtainable according to the process and the isolation of the desired isomer and/or the conversion of a free compound of the formula II obtainable according to the process to a salt or the conversion of a salt of a compound of the formula II obtainable according to the process to the free compound of the formula II or to another salt.