Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof
View Patent ↗The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I): wherein R 3 , R 4 , R 5 , R 6 , R 7 , P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.
1. An aryloazol-2-yl-cyanoethylamine compound of the formula (Id):
wherein:
R is alkylthio, haloalkylthio, alkoxy, haloalkoxy, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl;
R 2 is hydrogen;
R 8 is halogen, alkyl, haloalkyl, alkenyl, hydroxyalkyl, —CO 2 H, formyl, alkylcarbonyl, haloalkylcarbonyl, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl;
R 9 is hydrogen; and
R 10 and R 11 are independently hydrogen, halogen, alkyl, haloalkyl, hydroxyalkyl, alkenyl, formyl, —CO 2 H, alkylcarbonyl or haloalkylcarbonyl.
2. The compound of claim 1 , wherein:
R is haloalkylthio or haloalkoxy.
3. The compound of claim 1 , wherein:
R 8 is halogen, alkyl, haloalkyl, alkenyl or hydroxyalkyl.
4. The compound of claim 1 , wherein:
R 8 is —CO 2 H, alkylcarbonyl, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl.
5. The compound of claim 1 , wherein:
R 10 is halogen; and
R 11 is hydrogen or halogen.
6. The compound of claim 1 , wherein:
R is haloalkylthio or haloalkoxy;
R 8 is halogen, alkyl, haloalkyl or hydroxyalkyl; and
R 10 and R 11 are independently hydrogen, halogen, alkyl, haloalkyl, hydroxyalkyl, alkenyl or formyl.
7. The compound of claim 1 , wherein:
R is SCF 3 or OCF 3 ;
R 8 is halogen, haloalkyl or hydroxyalkyl;
R 10 is halogen; and
R 11 is hydrogen, halogen, hydroxyalkyl, haloalkyl, alkenyl or formyl.
8. The compound of claim 7 , wherein:
R 10 is Cl or Br; and
R 11 is hydrogen, Cl, I, vinyl, formyl, CHF 2 , CH 2 F, CF 3 or CH 2 OH.
9. The compound of claim 7 , wherein:
R 8 is Cl, Br, F, CHF 2 , CH 2 F, CF 3 or CH 2 OH.
10. The compound of claim 7 , wherein:
R 8 is Cl, CHF 2 , CH 2 F or CF 3 ;
R 10 is Cl; and
R 11 is H, Cl, CH 2 OH, CHF 2 , CH 2 F or CF 3 .
11. The compound of claim 7 , wherein:
R 8 is Cl, CHF 2 , CH 2 F or CF 3 ;
R 10 is Cl; and
R 11 is H or Cl.
12. The compound of claim 7 , wherein:
R 8 is Cl, CHF 2 or CF 3 ;
R 10 is Cl; and
R 11 is H or Cl.
13. A composition for the treatment or prevention of parasites in animals comprising an effective amount of a compound of claim 1 together with a pharmaceutically or veterinarily acceptable carrier.
14. The composition of claim 13 , wherein the composition is suitable for administration to an animal orally, topically or by injection.
15. The composition of claim 14 , wherein the composition is an oral drench.
16. The composition of claim 14 , wherein the composition is a pour-on composition.
17. A method of treating an endoparasitic infection in a mammal in need thereof comprising administering an effective amount of the compound of claim 1 to the mammal.
18. The method of claim 17 , wherein the endoparasitic infection is caused by a helminth selected from the group consisting of Anoplocephala, 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.
19. The method of claim 18 , wherein the helminth is Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus and combinations thereof.
20. The method of claim 17 , wherein the mammal is a livestock animal.