Heteroaryl-1,2,4-triazole and heteroaryl-tetrazole compounds for controlling ectoparasites

1. A process for preparing a compound of formula

wherein:

Q 4 and Q 2 are independently CR 5 or N, provided at least one of Q 4 and Q 2 is N;

Y is a direct bond or CH 2 ;

R 4 is H; C 1 -C 6 alkyl optionally substituted with one substituent selected from: CN, CONH 2 , COOH, NO 2 and Si(CH 3 ) 3 ; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH 2 —; or benzyl optionally substituted with halo or C 1 -C 3 haloalkyl;

R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the

group, each independently selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 thiohaloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halo, NO 2 , SF 5 , CN, CONH 2 , COOH and C(S)NH 2 ;

R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one substituent selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halo or hydroxy; and

R 5 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkoxyC(O)— or (C 4 -C 3 alkoxy) 2 CH—;

or a salt thereof;

the process comprising reacting an azole compound of formula (a) with a carboxylic acid of formula (b) to form a compound of formula (I′),

wherein R 1 , R 2 , R 3 , R 4 , Q 1 , and Q 2 are as defined above;

wherein the azole compound of formula (a) is prepared by:

(i) reacting an amine of formula (c) with a substituted azole of formula (d),

wherein LG is a suitable leaving group, and R 1 , R 3 , R 4 , Q 1 , and Q 2 are as defined above; or

(ii) reacting a substituted azole of formula (d) with ammonia to form a substituted azole of formula (e), and subsequently reacting the substituted azole of formula (e) with a compound of formula (f),

wherein LG is a suitable leaving group, and R 1 , R 3 , R 4 , Q 1 , and Q 2 are as defined above.

2. A process for preparing a compound of formula

wherein:

Y is a direct bond or CH 2 ;

R 4 is H; C 1 -C 6 alkyl optionally substituted with one substituent selected from: CN, CONH 2 , COOH, NO 2 and Si(CH 3 ) 3 ; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH 2 —; or benzyl optionally substituted with halo or C 1 -C 3 haloalkyl;

R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the

group, each independently selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 thiohaloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halo, NO 2 , SF 5 , CN, CONH 2 , COOH and C(S)NH 2 ;

R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one substituent selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halo or hydroxy; and

R 5 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkoxyC(O)— or (C 4 -C 3 alkoxy) 2 CH—;

or a salt thereof;

the process comprising reacting an amide of formula (n) with an N,N-dimethylamide dimethyl acetal of formula (g) to a form compound of formula (o) which is subsequently reacted with a substituted hydrazine of formula (j) under acidic conditions to form a compound of formula (I″),

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and Y are as defined above.

3. The process of claim 2 , wherein the compound of formula (I″) is N-[(1S)-1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide or a salt thereof.

4. The process of claim 2 , wherein the compound of formula (I″) is N-[(1S)-1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide.

5. A process for preparing a compound of formula

wherein:

Y is a direct bond or CH 2 ;

R 1 is H; C 1 -C 6 alkyl optionally substituted with one substituent selected from: CN, CONH 2 , COOH, NO 2 and —Si(CH 3 ) 3 ; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH 2 —; or benzyl optionally substituted with halo or C 1 -C 3 haloalkyl;

R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the

group, each independently selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 thiohaloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halo, NO 2 , SF 5 , CN, CONH 2 , COOH and C(S)NH 2 ;

R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one substituent selected from: C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 3 -C 4 cycloalkyl, halo or hydroxy; and

R 5 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkoxyC(O)— or (C 4 -C 3 alkoxy) 2 CH—;

or a salt thereof;

the process comprising reacting an amidine hydrochloride of formula (q) with an acid of formula (r) to form a compound of formula (t) which is subsequently reacted with a substituted hydrazine of formula (j) under acidic conditions to form a compound of formula (I″),

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and Y are as defined above.