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

1. A compound of the formula

wherein:

X is O or S;

Q 1 and Q 2 are independently CR 5 or N, provided at least one of Q 1 and Q 2 is N;

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 1 -C 3 alkoxy) 2 CH—;

or a salt thereof.

2. The compound or salt according to claim 1 , wherein Y is a direct bond.

3. The compound or salt according to claim 1 , wherein X is O.

4. The compound or salt according to claim 1 , wherein R 3 is methyl.

5. The compound or salt according to claim 1 , wherein Q 1 is N, Q 2 is CR 5 , and R 5 is H, methyl, or (CH 3 CH 2 O) 2 CH—.

6. The compound or salt according to claim 1 , wherein R 4 is 2-pyridine, or 2-pyrimidine optionally substituted by C 1 -C 3 alkoxy.

7. The compound or salt according to claim 6 , wherein R 4 is 2-pyrimidine.

8. The compound or salt according to claim 1 , wherein R 1 is cyclopropyl-CH 2 —, n-propyl, CH≡C—CH 2 —, CF 3 CH 2 CH 2 —, FCH 2 CH 2 —, FCH 2 CH 2 CH 2 —, 2,2-difluorocyclopropyl-CH 2 —, 2,2-dichlorocyclopropyl-CH 2 —, H, CH 3 , (CH 3 ) 3 SiCH 2 —, CH 3 CH 2 — or CNCH 2 —.

9. The compound or salt according to claim 8 , wherein R 1 is cyclopropyl-CH 2 —, CH≡C—CH 2 —, H or CH 3 .

10. The compound or salt according to claim 1 , wherein R 2 is 3,5-bis(trifluoromethyl)phenyl, 3,5-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 5-trifluoromethylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethylphenyl or 2,6-bis(trifluoromethyl)pyridin-4-yl.

11. The compound or salt according to claim 10 , wherein R 2 is 3,5-bis(trifluoromethyl)phenyl.

12. A formulation comprising a compound or salt according to claim 1 , and at least one acceptable carrier.

13. A method of controlling ectoparasites on an animal in need thereof comprising administering an effective amount of the compound or salt according to claim 1 .

14. The compound or salt according to claim 1 , which is:

N-(Cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

3,5-Dichloro-N-(cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]benzamide;

3,5-Dichloro-N-propyl-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]benzamide;

N-(Cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-(trifluoromethoxy)benzamide;

N-[(3-Chlorophenyl)methyl]-3-cyano-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]benzamide;

3-Chloro-N-(cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide;

3-Chloro-N-prop-2-ynyl-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide;

3-Chloro-N-propyl-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)pyridine-3-carboxamide;

3-Chloro-N-(cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethoxy)benzamide;

N-(2-Fluoroethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[1-[2-(2-Pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-b is (trifluoromethyl)-N-(3,3,3-trifluoropropyl)benzamide;

N-(Oxetan-3-ylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-(Cyanomethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-Prop-2-ynyl-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[(2,2-Difluorocyclopropyl)methyl]-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[(2,2-Dichlorocyclopropyl)methyl]-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Chloro-N-prop-2-ynyl-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethoxy)benzamide;

N-(2-Fluoroethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)-N-(3,3,3-trifluoropropyl)benzamide;

N-(3-Fluoropropyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Chloro-N-(2-fluoroethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide;

3-Chloro-N-(2-fluoroethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Chloro-N-(3-fluoropropyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Chloro-N-(3-fluoropropyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide;

3-Chloro-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)-N-(3,3,3-trifluoropropyl)benzamide;

3-Chloro-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)-N-(3,3,3-trifluoropropyl)benzamide;

N-(Cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-[1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)-N-(3,3,3-trifluoropropyl)pyridine-3-carboxamide;

N-(2-Fluoroethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-(3-Fluoropropyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-Prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-(Cyclopropylmethyl)-N-[1-(1-pyrimidin-2-yltetrazol-5-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Cyano-N-(cyclopropylmethyl)-N-[1-[5-methyl-2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]benzamide;

N-Prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Chloro-N-prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)-benzamide;

3-chloro-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide;

3-Cyano-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide;

N-(Cyclopropylmethyl)-N-[1-[2-(5-methoxypyrimidin-2-yl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Chloro-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Chloro-N-prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-[2-[2-(2-pyridyl)-1,2,4-triazol-3-yl]propyl]-3,5-bis(trifluoromethyl)benzamide;

N-Prop-2-ynyl-N-[(1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-(Cyclopropylmethyl)-N-R1S)-1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-R1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoro methyl)pyridine-3-carboxamide;

N-Prop-2-ynyl-N-[(1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Cyano-N-(cyclopropylmethyl)-N-[1-[2-(2-pyridyl)-1,2,4-triazol-3-yl]ethyl]benzenecarbothioamide;

N-(Cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-R1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Cyano-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-2,6-bis(trifluoromethyl)pyridine-4-carboxamide;

3-Cyano-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide;

N-Ethyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Cyano-N-prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide;

3-Cyano-N-methyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide;

N-(Cyanomethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Cyano-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Cyano-N-prop-2-ynyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Cyano-N-ethyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

3-Cyano-N-methyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-[1-(5-methyl-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

3-Bromo-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

N-[1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-R1S)-1-[2-(5-fluoropyrimidin-2-yl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-Methyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[(1S)-1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)-N-(trimethylsilylmethyl)benzamide;

3-Cyano-N-R1S)-1-[2-(5-fluoropyrimidin-2-yl)-1,2,4-triazol-3-yl]ethyl]benzamide;

N-R1S)-1-[2-(5-Fluoropyrimidin-2-yl)-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

N-(Cyclopropylmethyl)-N-R1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)bent enecarbothioamide;

3-Carbamothioyl-N-methyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide;

3-Carbamothioyl-N-methyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide;

N-[1-[5-(Diethoxymethyl)-2-pyrimidin-2-yl-1,2,4-triazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide;

Methyl5-[1-[[3,5-bis(trifluoromethyl)benzoyl]amino]ethyl]-1-pyrimidin-2-yl-1,2,4-triazole-3-carboxylate; or

N-Methyl-N-R1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide.

15. The compound or salt according to claim 1 , which is N-(cyclopropylmethyl)-N-[(1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide, N-Prop-2-ynyl-N-[(1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-b is (trifluoromethyl)benzamide or N-methyl-N-[(1S)-1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide.

16. A compound that is N-R1S)-1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide or a salt thereof.

17. A compound that is N-[(1S)-1-(2-Pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide.