Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof

1. An aryloazol-2-yl-cyanoethylamine compound of the formula (I):

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, and haloalkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl; unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl; or unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, and di(alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

R 6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, and di(alkyl)amino;

R 7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino, and di(alkyl)amino; unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, and di(alkyl)amino; or

unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, and di(alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ;

a is 1, 2 or 3;

p is 0, 1 or 2; and

salts thereof.

2. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 or N;

X is C—R 10 or N;

Y is C—R 11 or N;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, hydroxy-C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio arylthio, C 1 -C 6 -alkoxy, phenoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarboxylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, formyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, and halo-C 1 -C 6 -alkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyloxy-C 1 -C 6 -alkyl; unsubstituted or substituted C 3 -C 7 -cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and C 1 -C 6 -alkyl; or unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, 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, and di(C 1 -C 6 -alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

R 6 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, 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, and di(C 1 -C 6 -alkyl)amino;

R 7 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, phenyl, phenoxy, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, 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, and di(C 1 -C 6 -alkyl)amino; unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino; or

unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ;

a is 1, 2 or 3;

p is 0, 1 or 2; and

salts thereof.

3. The aryloazol-2-yl-cyanoethylamine of claim 2 , wherein

P and Q are N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, hydroxy-C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio arylthio, C 1 -C 6 -alkoxy, phenoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarboxylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, formyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, and halo-C 1 -C 6 -alkylsulfonyl;

R 3 , R 4 and R 6 are H;

R 5 is methyl;

R 7 is unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

Z is C(O); and

a is 1; and

salts thereof.

4. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

P and Q are N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 3 , R 4 and R 6 are hydrogen;

R 5 is hydrogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy-C 1 -C 6 -alkyl, or C 1 -C 6 -alkylsulfonyloxy-C 1 -C 6 -alkyl;

R 7 is unsubstituted phenyl or phenyl substituted by one or more substituents selected from the group consisting of C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, phenyl, phenyloxy, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylsulfinyl and halo-C 1 -C 6 -alkylsulfonyl;

R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, cyano, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylamino, hydroxy-C 1 -C 6 -alkyl, formyl, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C— or unsubstituted or substituted phenyl wherein the substituents are C 1 -C 6 -alkyl or halo-C 1 -C 6 -alkyl;

Z is C(O);

a is 1; and

salts thereof.

5. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

P and Q are N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl, ethyl, butyl, CH 2 OH, CH 2 OCH 3 , CH 2 SCH 3 , or CH 2 OSO 2 CH 3 ;

R 7 is a phenyl substituted with butyl, CF 3 , phenyl, phenoxy, OCF 3 , SCF 3 , SOCF 3 , or SO 2 CF 3 ;

R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, methyl, CH 2 NH 2 , CH 2 N(CH 3 ) 2 , vinyl, CH 2 OH, CH(OH)CH 2 OH, CO 2 H, CO 2 CH 3 , Ph-CF 3 , F, Cl, Br, CF 3 , OCF 3 or CN;

Z is C(O);

a is 1; and

salts thereof.

6. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

P is N;

Q is C—R 2 ;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 is hydrogen, Cl, methyl, methoxy, ethoxy, propoxy, butoxy, O(CH 2 ) 2 OCH 3 , or O(CH 2 ) 2 N(CH 3 ) 2 ;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 , phenoxy, or SCF 3 ;

R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, Cl, Br, C 1 -C 6 -alkyl, CF 3 , nitro, amino, amido, CO 2 CH 3 , or NHCOCH 3 ;

Z is C(O);

a is 1; and

salts thereof.

7. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

P is N;

Q is C—R 2 or N;

V is N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 is hydrogen, Cl, Br, or methoxy;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 or SCF 3 ;

R 9 , R 10 and R 11 each, independently of one another, is hydrogen, Cl, Br or methyl;

Z is C(O); and

a is 1; and

salts thereof.

8. A pesticidal composition comprising a compound of claim 1 and a pesticidally or veterinarily acceptable carrier.

9. The pesticidal composition of claim 8 which further comprises an additional pesticidal compound.

10. A method of making the compounds of formula (I) of claim 1 which comprises of:

(i) obtaining the carbonyl compounds of formula (IV) by treatment of a NH-aryl-azole of general formula (V) with compound of general formula (VI)

wherein

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl; unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl; unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

a is 1, 2 or 3; and T is a leaving group;

(ii) obtaining the α-amino nitrile derivatives of formula (II) by treatment of carbonyl compounds of general formula (IV) with a cyanide source with an amine of general formula R 6 —NH 2 in the presence of an ammonium salt:

 wherein, R 3 , R 4 , R 5 , P, Q, V, W, X, Y, and a are as defined above; and R 6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino; and

(iii) reacting compound (II) with compound (III) in the presence of a base in a solvent:

wherein R 3 , R 4 , R 5 , R 6 , P, Q, V, W, X, Y, and a are as defined above;

R 7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino and di(alkyl)amino; unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino; or

 unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ;

p is 0, 1 or 2; and T is a leaving group.

11. A method of treating an endoparasitic infection in a mammal in need thereof which comprises administering an effective amount of the compound of claim 1 to the mammal.

12. The method of claim 11 , wherein the endoparasitic infection is caused by a helminth selected from the group consisting of Anaplocephala, Ancylostoma, Anecator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostumum, Onchocerca, Ostertagia, Oxyuris, Paracaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorous, Uncinaria, Wuchereria , and combinations thereof.

13. The method of claim 12 , wherein the helminth is Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus and combinations thereof.

14. The method of claim 13 , wherein the helminth is Haemonchus contortus and the compound is a compound of formula (I) wherein:

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 is hydrogen, Cl, Br, methyl or methoxy;

R 3 , R 4 and R 6 are H;

R 5 is methyl;

R 7 is phenyl substituted with OCF 3 , SCF 3 or CHFCF 3 ;

R 8 is H, Cl, Br, F or CN;

R 9 is H, Cl or Br;

R 10 is H, Cl, Br or CF 3 ;

R 11 is H, Cl, Br or methyl;

Z is C(O); and

a is 1.

15. The method of claim 13 , wherein the helminth is Haemonchus contortus and the compound is a compound of formula (I) wherein:

P is N;

Q is C—R 2 or N;

V is N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 is hydrogen, Cl, Br or methoxy;

R 3 , R 4 and R 6 are H;

R 5 is methyl;

R 7 is phenyl substituted with OCF 3 or SCF 3 ;

R 9 is H;

R 10 is Cl or Br;

R 11 is H;

Z is C(O); and

a is 1.

16. A method of treating an ectoparasitic infection in a mammal in need thereof which comprises administering an effective amount of the compound of claim 1 to the mammal.

17. The method of claim 16 , wherein the ectoparasitic infection is caused by an ectoparasite selected from the group consisting of fleas, ticks, mites, mosquitoes, flies, lice, blowfly and combinations thereof.

18. The method of claim 17 , wherein the ectoparasite are fleas.

19. A process of making the aryloazol-2-yl-cyanoethylamine compound of claim 1 which comprises:

(a)(i) reacting a compound of formula (V):

with a compound of formula (VI):

to form the compound of formula (IV):

wherein

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 , R 9 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl; unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl; unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

T is a leaving group; and

a is 1, 2 or 3; or

(a)(ii) reacting a compound of formula (XIV):

with a compound of formula (XV):

to form the compound of formula (XIII)

wherein V, W, X and Y are as defined above;

R 16 is halogen or trifluoromethanesulfonyl; and

R 14 and R 15 are independently C 1 -C 4 alkyl or C 1 -C 4 alkylcarbonyl; and

M is trialkyltin, a boronic acid or a boronate ester;

subjecting the compound of formula (XIII) to oxidative cleavage to form the compound of formula (X):

reacting the compound of formula (X) with a compound of formula (XI):

wherein R 3 , R 4 , R 5 and a are as defined above, and R 12 is a hydroxy protecting group:

to form the compound of formula (IX):

subjecting the compound of formula (IX) to a heterocyclization step to form the compound of formula (VIII):

subjecting the compound of formula (VIII) to deprotection of the hydroxyl protecting group to form the compound of formula (VII):

 where Q is CH; and

oxidizing the compound of formula (VII) to form the compound of formula (IV) where Q is CH;

(b) reacting the compound of formula (IV)

with R 6 -NH 2 , where R 6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino, to form the compound of formula (II): and

(c) reacting a compound of formula (II) with T-Z—R 7 , wherein R 7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino and di(alkyl)amino;

unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino; or

unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ; and T is a leaving group, in the presence of a base, to form the compound of claim 1 ,

wherein

P is N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 2 R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkenyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfonylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl; unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl; unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

R 6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino;

R 7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino and di(alkyl)amino; unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino; or

unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ;

a is 1, 2 or 3; and

p is 0, 1 or 2.

20. The compound of claim 1 wherein the compound has the formula (Ie)

wherein:

R═SCF 3 or OCF 3 ;

Q=C—R 2 ;

R 2 is hydrogen, Br, F, Cl, methyl, methoxy, ethoxy or propoxy; and

R 9 , R 10 and R 11 are each independently H, halogen or C 1 -C 6 -alkyl.

21. The compound of claim 20 , wherein

R 2 is H, Br or methoxy; and

R 9 , R 10 and R 11 are each independently H, Br or Cl.

22. The compound of claim 21 , wherein

R 2 is H; and

R 9 , R 10 and R 11 are each independently H, Br or Cl.

23. The compound of claim 22 , wherein

R is OCF 3 ;

R 2 is H; and

R 9 and R 11 are H; and

R 10 is Br.

24. The compound of claim 1 wherein the compound has the formula (Id)

wherein:

R═SCF 3 or OCF 3 ;

R 2 is hydrogen, Br, F, Cl, methyl, methoxy, ethoxy, propoxy, butoxy, O(CH 2 ) 2 OCH 3 , or O(CH 2 ) 2 N(CH 3 ) 2 ; and

R 8 , R 9 , R 10 and R 11 are each independently H, halogen, nitro, amino, amido, alkylcarbonylamino, HO 2 C—, alkyl-O 2 C—, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkyl.

25. The compound of claim 24 , wherein

R 2 is hydrogen, Br, Cl, methyl, methoxy or ethoxy; and

R 8 , R 9 , R 10 and R 11 are each independently H, Cl, Br, methyl, CF 3 , or nitro.

26. The compound of claim 25 , wherein

R 2 is hydrogen or methoxy; and

R 8 , R 9 , R 10 and R 11 are each independently H, Cl or Br.

27. The compound of claim 1 , wherein the compound has the formula (Ic)

wherein:

R═SCF 3 or OCF 3 ;

R 5 is C 1 -C 6 -alkyl, hydroxyalkyl, alkylthioalkyl or alkylsulfonyloxyalkyl; and

R 8 , R 9 , R 10 and R 11 are each independently H, halogen, cyano, amino, aminoalkyl, alkylaminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy.

28. The compound of claim 27 , wherein:

R 5 is C 1 -C 6 -alkyl, or hydroxyalkyl; and

R 8 , R 9 , R 10 and R 11 are each independently H, halogen, HO 2 C—, alkyl-O 2 C—, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy.

29. The compound of claim 28 , wherein:

R 5 is methyl, or hydroxyalkyl; and

R 8 , R 9 , R 10 and R 11 are each independently H, methyl, CF 3 , Cl, Br, F, methoxy or trifluoromethoxy.

30. The compound of claim 20 , wherein:

R is OCF 3 ;

R 2 is methyl;

R 9 and R 11 are each H; and

R 10 is Br.