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 method of controlling ectoparasites in cattle or sheep comprising applying to the back of the cattle or sheep a pour-on skin solution comprising an effective insecticidal amount of 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. A method of claim 1 , wherein the compound is Compound 5.
3. A method of claim 1 , wherein the ectoparasites are selected from the group consisting of fleas, ticks, mites mosquitoes, flies, lice, blowfly and combinations thereof.
4. A method of claim 1 wherein the method is for controlling Boophilus microplus in cattle.
5. A method of claim 1 wherein the method is for controlling ticks in sheep.
6. A method of claim 1 , wherein the solution is applied every month or every two months.
7. A method of claim 1 wherein the solution comprises from 0.05 to 10% weight/volume of the compound.
8. A method of claim 1 wherein the solution comprises from 0.1 to 2% weight/volume of the compound.
9. A method of claim 1 wherein the solution comprises from 0.25 to 1.5% weight/volume of the compound.
10. A method of claim 1 wherein the solution comprises about 1% weight/volume of the compound.
11. A method of claim 1 wherein the effective insecticidal amount of the compound is between 0.001 and about 100 mg/kg of the cattle or sheep.
12. The method of claim 1 wherein the effective insecticidal amount of the compound is between 0.001 to about 50 mg/kg of the cattle or sheep.
13. A method of claim 1 wherein the effective insecticidal amount of the compound is about 1 mg/kg of the cattle or sheep.
14. A method of claim 1 wherein the applying of the pour-on skin solution is prior to the cattle or sheep arriving in the feed lot.
15. A method of claim 1 wherein the applying of the pour-on skin solution ceases from between one to two months prior to slaughter.
16. A method of claim 1 wherein the applying of the pour-on skin solution is to the back of the sheep or cattle at one or more points along a line of the back.
17. A method of claim 1 wherein the solution comprises a solvent, a diluent, and optionally an emollient.
18. A method of claim 17 , wherein the solvent is selected from the group consisting of:
acetyl tributyl citrate, fatty acid esters, diisobutyl adipate, acetone, acetonitrile, benzyl alcohol, butyl diglycol, dimethylacetamide, dimethylformamide, dipropylene glycol n-butyl ether, ethanol, isopropanol, methanol, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, monomethylacetamide, dipropylene glycol monomethyl ether, liquid polyoxyethylene glycols, propylene glycol, 2-pyrrolidone, N-methylpyrrolidone, diethylene glycol monoethyl ether, ethylene glycol and diethyl phthalate, or a mixture of at least two of these solvents.
19. A method of claim 17 wherein the diluent is selected from the group consisting of: plant oils;
mineral oils aliphatic or cyclic hydrocarbons.
20. A method of claim 17 , wherein the emollient is selected from the group of agents:
(a) polyvinylpyrrolidone, polyvinyl alcohols, polyethylene glycols, benzyl alcohol, mannitol, glycerol, sorbitol, polyoxyethylenated sorbitan esters; lecithin, sodium carboxymethylcellulose, silicone oils, polydiorganosiloxane oils,
(b) anionic surfactants such as alkaline stearates, sodium, potassium or ammonium stearates; calcium stearate, triethanolamine stearate; sodium abietate; alkyl sulphates, sodium dodecylbenzenesulphonate, sodium dioctylsulphosuccinate; fatty acids,
(c) cationic surfactants,
(d) amine salts of formula N + R′R″R′″ in which the radicals R are optionally hydroxylated hydrocarbon radicals; octadecylamine hydrochloride is among the cationic surfactants which can be used,
(e) nonionic surfactants, and
(f) amphoteric surfactants, or
(g) a mixture of at least two of these agents.