1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
Provided are 1-aryl-5-alkyl pyrazole compounds, of formula (I): wherein: R 1 is hydrogen, cyano, halogen, R 8 , formyl, —C(O)R 8 , —C(O)OR 8 , —C(O)NR 9 R 10 , or —C(S)NH 2 ; R 2 is R 8 or —S(O) m R 11 ; R 3 is methyl, ethyl or C 1 -C 4 haloalkyl; R 4 , R 5 and R 7 are independently hydrogen, halogen, alkyl, haloalkyl, cyano or nitro; R 6 is halogen, alkyl, haloalkyl, alkoxy, haloalkyloxy, cyano, nitro, —C(O)R 12 , —S(O) n R 12 or SF 5 ; Z is a nitrogen atom or C—R 13 ; R 8 is alkyl, haloalkyl, cycloalkyl or halocycloalkyl; R 9 is hydrogen, alkyl, haloalkyl or alkoxy; R 10 is hydrogen, alkyl, haloalkyl or alkoxy; R 11 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl or cycloalkyl; R 12 is alkyl or haloalkyl; R 13 is hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy; m is 0, 1 or 2; and n is 0, 1 or 2; or a salt thereof, the method of making compounds of formula (I) and the use of these compounds against ectoparasites, endoparasites and pests.
1. A compound of formula (I), wherein R 5 and R 7 are each hydrogen; and R 1 , R 2 , R 3 , R 4 , R 6 and Z are as defined below for Compound 1 to Compound 48:
(I)
Compound
#
R 1
R 2
R 3
R 4
R 6
Z
1
CN
SCF 3
CH 3
Cl
CF 3
C—Cl
2
CN
SCF 3
CH 2 CH 3
Cl
CF 3
C—Cl
3
CN
SCF 3
CH 2 F
Cl
CF 3
C—Cl
4
CN
S(O) 2 CF 3
CH 3
Cl
CF 3
C—Cl
5
CN
S(O)CF 3
CH 3
Cl
CF 3
C—Cl
6
CN
SCF 3
CH 3
F
CF 3
C—F
7
CN
SCF 3
CH 3
Cl
CF 3
C—F
8
CN
SCF 3
CH 2 F
Cl
CF 3
C—F
9
CN
S(O)CF 3
CH 3
Cl
CF 3
C—F
10
CN
S(O)CF 3
CH 2 F
Cl
CF 3
C—Cl
11
CN
S(O)CF 3
CH 2 F
Cl
CF 3
C—F
12
CN
S(O)CF 3
CH 3
F
CF 3
C—F
13
CN
SCF 3
CH 3
H
CF 3
C—F
14
CN
S(O)CF 3
CH 3
H
CF 3
C—F
15
CN
SCCl 2 F
CH 3
Cl
CF 3
C—Cl
16
CN
SCF 3
CH 2 F
Cl
OCF 3
C—Cl
17
CN
SCF 3
CH 3
Cl
OCF 3
C—Cl
18
CN
S(O)CF 3
CH 2 F
Cl
OCF 3
C—Cl
19
CN
S(O)CF 3
CH 3
Cl
OCF 3
C—Cl
20
CN
S(O)CCl 2 F
CH 3
Cl
CF 3
C—Cl
21
CN
SCCl 2 F
CH 2 F
Cl
OCF 3
C—Cl
22
CN
S(O)CCl 2 F
CH 2 F
Cl
OCF 3
C—Cl
23
CN
SCCl 2 F
CH 3
Cl
OCF 3
C—Cl
24
CN
S(O)CCl 2 F
CH 3
Cl
OCF 3
C—Cl
25
CN
SCCl 2 F
CH 2 F
Cl
CF 3
C—F
26
CN
SCCl 2 F
CH 3
Cl
CF 3
C—F
27
CN
SCCl 2 F
CH 3
H
CF 3
C—Cl
28
CN
S(O)CCl 2 F
CH 2 F
Cl
CF 3
C—F
29
CN
S(O)CCl 2 F
CH 3
Cl
CF 3
C—F
30
CN
S(O)CCl 2 F
CH 3
H
CF 3
C—Cl
31
CN
S(O) 2 CCl 2 F
CH 3
Cl
CF 3
C—F
32
CN
S(O) 2 CCl 2 F
CH 2 F
Cl
CF 3
C—F
33
CN
SCF 3
CH 2 F
Cl
SF 5
C—Cl
34
CN
SCF 3
CH 3
Cl
SF 5
C—Cl
35
CN
SCClF 2
CH 2 F
Cl
CF 3
C—F
36
CN
SCClF 2
CH 3
Cl
CF 3
C—F
37
CN
S(O)CClF 2
CH 3
Cl
CF 3
C—F
38
CN
S(O)CClF 2
CH 2 F
Cl
CF 3
C—F
39
CN
S(O) 2 CClF 2
CH 3
Cl
CF 3
C—F
40
CN
S(O) 2 CClF 2
CH 2 F
Cl
CF 3
C—F
41
CN
S(O) 2 CCl 2 F
CH 3
Cl
CF 3
C—Cl
42
CN
SCCl 2 F
CH 3
Cl
SF 5
C—Cl
43
CN
SCF 3
CH 3
Cl
CF 3
C—CH 3
44
CN
S(O)CF 3
CH 3
Cl
CF 3
C—CH 3
45
CN
SCCl 2 F
CHF 2
Cl
CF 3
C—F
46
CN
S(O)CCl 2 F
CHF 2
Cl
CF 3
C—F
47
CN
SCCl 2 F
CH 3
Cl
CF 3
N
48
CN
S(O)CCl 2 F
CH 3
Cl
CF 3
N.
2. The compound of claim 1 , wherein the compound is Compound 5, Compound 9 or Compound 29.
3. The compound of claim 2 , wherein the compound is Compound 5.
4. The compound of claim 2 , wherein the compound is Compound 9.
5. The compound of claim 2 , wherein the compound is Compound 29.
6. A veterinary composition comprising a compound of formula (I) in claim 1 together with a veterinarily acceptable carrier.
7. The veterinary composition of claim 6 , wherein the composition is a topical composition.
8. The topical veterinary formulation of claim 7 , wherein the composition is a spot-on or pour-on composition.
9. The composition of claim 6 , wherein the compound of formula (I) is Compound 5.
10. The composition of claim 6 , wherein the compound of formula (I) is Compound 9.
11. The composition of claim 6 , wherein the compound of formula (I) is Compound 29.
12. The composition of claim 6 , wherein the composition further comprises an additional veterinarily-active ingredient.
13. The composition of claim 12 , wherein the additional veterinarily-active ingredient is selected from the group consisting of arylpyrazoles, nodulisporic acid or derivatives thereof, macrocyclic lactones, formamidines, pyrethroids, insect growth regulators, benzenedisulfonamide compounds, anti-cestodal agents, neonicotinoid active agents, a spinosyn, depsipeptides and metaflumizone, or mixtures thereof.
14. The composition of claim 13 , wherein the macrocyclic lactone is abamectin, dimadectin, doramectin, emamectin, eprinomectin, ivermectin, latidectin, lepimectin, selamectin, milbemectin, milbemycin D, moxidectin, nemadectin or milbemycin oxime.
15. The composition of claim 13 , wherein the formamidine is amitraz.
16. The composition of claim 13 , wherein the anti-cestodal active agent is praziquantel, pyrantel or morantel.
17. A method for the therapeutic and/or prophylactic treatment of an animal against an ectoparasitic infestation or an endoparasitic infection comprising administering an effective amount of the compound of claim 1 to the animal in need thereof.
18. The method of claim 17 , wherein the animal is treated against an ectoparasitic infestation.
19. The method of claim 18 , wherein the ectoparasite is a parasitic fly selected from Haematobia sp., Stomoxys sp., Dermatobia sp. and Cochliomyia sp.
20. The method of claim 19 , wherein the ectoparasite is Haematobia irritans.