NZ209781A - Pour-on parasiticidal compositions - Google Patents
Pour-on parasiticidal compositionsInfo
- Publication number
- NZ209781A NZ209781A NZ209781A NZ20978184A NZ209781A NZ 209781 A NZ209781 A NZ 209781A NZ 209781 A NZ209781 A NZ 209781A NZ 20978184 A NZ20978184 A NZ 20978184A NZ 209781 A NZ209781 A NZ 209781A
- Authority
- NZ
- New Zealand
- Prior art keywords
- pour
- composition according
- levamisole
- pyrethroid
- acid
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Toxicology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
<div class="application article clearfix" id="description">
<p class="printTableText" lang="en">New Zealand Paient Spedficaiion for Paient Number £09781 <br><br>
20978 <br><br>
Priority Date(s): .../. ?; Jf?. <br><br>
Complete Specification Filed: <br><br>
Class: <br><br>
({?! ... $'r)JN.6>. y. <br><br>
Publication Date: ]??7... <br><br>
P.O. Journal, No: . <br><br>
HO DRAWINGS <br><br>
Patents Form No. 5 Number <br><br>
PATENTS ACT 1953 Dated <br><br>
COMPLETE SPECIFICATION <br><br>
PARASITICIDAL FORMULATIONS <br><br>
f^We JANSSEN PHARMACEUTICA N.V. a company organised under the laws of Belgium of Turnhoutsebaan 30, B-2340-Beerse, Belgium do hereby declare the invention for which Hv/s pray that a Patent may be granted toxK/us, and the method by which it is to be performed, to be particularly described in and by the following statement: <br><br>
- 1 - (followed by 1a) <br><br>
10 <br><br>
This invention relates to parasiticidal formulations which are useful in eradicating and/or controlling both endo- and ectoparasites 15 attacking warm-blooded non-human animals. <br><br>
Animals like sheep and cattle are often simultaneously infected by both endoparasites, such as gut and lungworms, and ectoparasites such as, for example, lice, keds, mites, ticks and fleas. <br><br>
Most parasiticidal compounds have a rather selective activity: 20 some compounds have predominantly ectoparasiticidal activity while other confounds have predominantly endoparasiticidal activity. In order to control both types of parasites, separate applications of an endoparasiticide and of an ectoparasiticide will generally be required. <br><br>
25 One effective and preferred endoparasiticidal, and more specifically anthelmintic, compound is 2,3,5,6-tetrahydro-6-phenyl-imidazo[2,l-b]thiazole, the racemic form of which is generically designated as tetramisole, while the laevorotatory form; which bears most of the anthelmintic activity, is generically indicated as 30 levamisole. Tetramisole and levamisole are described e.g. in British Patent Nos. 1,043,489, respectively 1,152,544. <br><br>
An important group of insecticides, which are increasingly used to eradicate ectoparasites on animals, are the synthetic pyrethroids, which combine great ectoparasiticidal activity with a relatively high <br><br>
I <br><br>
2 097 S 1 <br><br>
-2- <br><br>
degree of safety towards animals and humans. Potent insecticides within the group of synthetic pyrethroids are, for example, cypermethrin, deltamethrin, cyhalothrin, flumethrin, cyfluthrin, tralomethrin, tralocythrin, fenvalerate, permethrin and phenothrin. 5 In view of the desirability to control both endo- and ecto parasites simultaneously with one treatment, it would obviously be a desirable objective to combine tetramisole or levamisole with an appropriate pyrethroid in one single formulation for application to the infected animals. Preferably such a formulation would be a 10 pour-on or spot-on formulation, wherein the active compound is <br><br>
•n."" <br><br>
dissolved or suspended in a suitable solvent or carrier and poured directly on to an infested animal, e.g. along the backline, or discrete spots are locally applied. Various anthelmintic pour-on compositions which contain levamisole as an active ingredient are now \ 15 widely used in practice. In U.K. Patent Application No. 2,110,092 A <br><br>
there are described certain pour-on formulations, which comprise a mixture of cyhalothrin with levamisole or tetramisole free base in a carrier comprising particular combinations of an alcohol solvent with an ester co-solvent. <br><br>
20 In a preferred embodiment, trie compositions are taught to contain one or more carboxylic acids selected from the group consisting of to Cg alkanoic acids. According to the reference, the molar ratio of alkanoic acid to levamisole free base should not exceed 1.1 and most preferably the alkanoic acid and 25 levamisole free base are in substantially equimolar proportions. <br><br>
It has however been found that synthetic pyrethroids tend not to be stable when incorporated in a pour-on formulation which further comprises tetra- or levamisole, such as those described in U.K. <br><br>
^ Patent Application No. 2.110.092 A. As a matter of fact, it has been <br><br>
30 observed that, when such formulations are stored for some time, a considerable part of the synthetic pyrethroid is destroyed, giving rise to ineffective formulations. It is therefore an object of this invention to provide pour-on formulations which comprise levamisole or tetramisole in combination with a pyrethroid and which are stable 35 for a sufficiently long period of time, preferably at least 6 months. <br><br>
by preventing or at least retarding any decomposition of the individual active ingredients. <br><br>
A further object is to provide a pour-on or spot-on endo- and ectoparasiticidal formulation of levamisole or tetramisole and a 5 synthetic pyrethroid in a suitable solvent and which retains useful or unimpaired efficacy against parasites after storage of the formulation for a prolonged period e.g. greater than one year. <br><br>
As used herein, the term "parasites" is meant to include endoparasites, e.g. gut and lungworms, as well as ectoparasites, e.g. 10 lice, keds, mites, ticks, fleas, blowfly. <br><br>
The term "controlling parasites" is meant to include the killing and/or the interference with the development and/or reproduction of said parasites. <br><br>
The term "unimpaired efficacy" means that the formulations have an 15 efficacy which is unimpaired in comparison with the efficacy of two compositions comprising the same amount of levamisole and a synthetic pyrethroid separately. <br><br>
The term "useful efficacy" means that the formulations have an efficacy greater than that of a mixture which has undergone 20 decomposition but less than unimpaired efficacy. <br><br>
The term "lower alkyl" designates alkyl radicals having 1 to 6 carbon atoms. <br><br>
According to the invention, it has been found that pour-on formulations which combine tetramisole or levamisole with a synthetic pyrethroid can be made stable by adding thereto one or more optionally substituted aliphatic carboxylic acids having a pKa value 25 in the range of 0.6 to 6, said acid or acids being present in a proportion of at least 1.5 and preferably at least 2.5 acid equivalents per mole of tetramisole or levamisole. <br><br>
In principle there is no upper limit to the acid content of the formulation, but, for reasons of acceptability and lack of irritation, 30 the acid component should not represent more than about 40% (w/v) and preferably not more than 35% (w/v) of the formulation. <br><br>
Consequently, there are provided by the subject invention parasiticidal compositions which comprise in admixture; i) an anti-ectoparasitic amount of a pyrethroid having the formula <br><br>
35 I—patent office <br><br>
-4- <br><br>
T « <br><br>
Q^^CH-O-C-L <br><br>
(I) <br><br>
10 <br><br>
wherein: <br><br>
Y is hydrogen or cyano; R is hydrogen or halo; <br><br>
5 is CH or N; and L is a radical of the formula a) -CH—CH-CH=C <br><br>
X <br><br>
H3C CH3 <br><br>
15 <br><br>
wherein: R is halo or lower alkyl, and 2 <br><br>
R is halo, lower alkyl, halophenyl or trifluoromethy1; <br><br>
20 <br><br>
b) -CH—CH—CH-C e hXh, & <br><br>
wherein each of R^, R^, R~* and R^ is halo, <br><br>
25 <br><br>
^CH3 <br><br>
c) -CH-CC" <br><br>
H3C^CH3 CH3 <br><br>
30 <br><br>
35 <br><br>
d) <br><br>
e) <br><br>
V Vp7 <br><br>
*/ NcH3 R <br><br>
or <br><br>
f> Oi '"j ^ 4 <br><br>
riu'diCI <br><br>
-5- <br><br>
wherein : n is 0 or 1# R is halo/ trifluoromethyl or difluoromethoxy, and 8 <br><br>
R is hydrogen or halo; <br><br>
1 2 <br><br>
provided that when said R is hydrogen and said R and R 5 are both chloro, then said Q is N; <br><br>
ii) an anthelmintic amount of levamisole or tetramisole or a mixture thereof; <br><br>
iii) at least one optionally substituted carboxylic acid having a pKa value in the range of 0.6 to 6, said acid or acids being <br><br>
10 present in a proportion of at least 1.5 acid equivalents per mole of levamisole and/or tetramisole; and iv) a solvent. <br><br>
Similar compositions containing a combination of tetramisole and/or levamisole with cypermethrin as an insecticidal active 15 ingredient are described and claimed in New Zealand Patent Specification No. 204735. The composi tions described and claimed therein are excluded from the scope of the subject invention. <br><br>
Specific pyrethroids of formula (I) which can advantageously be 20 used in compositions according to the subject invention are listed in the following Table I. <br><br>
Table I: Compounds of formula I. <br><br>
30 <br><br>
35 <br><br>
L <br><br>
Q <br><br>
R <br><br>
y <br><br>
Generic designation <br><br>
/C1 <br><br>
-CH — CH-CH=C H3C^CH3 C1 <br><br>
N <br><br>
H <br><br>
CN <br><br>
DOWCO-417 <br><br>
/Br <br><br>
-CH—CH—CH=C <br><br>
H C^CH Bl 3 3 <br><br>
CH <br><br>
H <br><br>
CN <br><br>
Deltamethrin <br><br>
■v.r&vr office 1 1 MOV 1986 <br><br>
RECEIVED <br><br>
v' ■ i -t ■»>* <br><br>
-6- <br><br>
Table I (cont'd) <br><br>
L <br><br>
Q <br><br>
R <br><br>
Y <br><br>
Generic designation <br><br>
-CH—CH-CH=C . <br><br>
CF <br><br>
H3C CH3 3 <br><br>
CH <br><br>
H <br><br>
CN <br><br>
Cyhalothrin <br><br>
^ CI <br><br>
-CH—CH-CH=C <br><br>
>< NC1 H3C^ CH3 <br><br>
CH <br><br>
F <br><br>
CN <br><br>
Cyfluthrin <br><br>
-CHo <br><br>
-CH—CH-CH=C^ H3C-^><\:H3 CH3 <br><br>
CH <br><br>
H <br><br>
CN <br><br>
Cyphenothrin <br><br>
/C1 <br><br>
-CH— CH-CH=C /—a h3cx;„3 ^ <br><br>
CH <br><br>
F <br><br>
CN <br><br>
Flumethrin <br><br>
/Br <br><br>
-CH—CH—CH—C^ H3C^KN:H3 Br Br Br <br><br>
CH <br><br>
H <br><br>
CN <br><br>
Tralomethrin <br><br>
Br <br><br>
-CH—CH—CH-C <br><br>
h3c-^ch3 ci ci Br <br><br>
CH <br><br>
H <br><br>
CN <br><br>
Tralocythrin <br><br>
/CH3 <br><br>
-ch- c h cyxch"ch3 3 3 <br><br>
CH <br><br>
h <br><br>
CN <br><br>
Fenpropathin dD <br><br>
-CH—C <br><br>
hsc^chj <br><br>
CH <br><br>
h <br><br>
CN <br><br>
Cypothrin <br><br>
10 <br><br>
15 <br><br>
20 <br><br>
25 <br><br>
30 <br><br>
35 <br><br>
Table I (cont'd) <br><br>
10 <br><br>
15 <br><br>
20 <br><br>
25 <br><br>
isomeric forms and mixtures thereof, including geometric isomers (cis and trans) and optical isomers. <br><br>
30 Particularly potent insecticides within the group of synthetic pyrethroids are those wherein the ester group is derived from an o(-cyano alcohol, i.e. the synthetic pyrethroids of formula (I) <br><br>
wherein Y is cyano. Pour-on compositions containing said pyrethroids, hereinafter referred to as «(-cyanopyrethroids, are particularly 35 preferred within the present invention. <br><br>
Q R Y Generic designation <br><br>
-CH—^V-C <br><br>
\ / C1 <br><br>
^ \=/ ch h cn Fenvalerate <br><br>
/ \ <br><br>
ch3 ch3 <br><br>
-ch—p 0-chf2 <br><br>
ch / \ <br><br>
ch3 ch3 <br><br>
ch h cn ac-222705 <br><br>
-ch-nh—^ y- <br><br>
ch <br><br>
CF3 <br><br>
\=/ CH H CN Fluvalerate. <br><br>
X \ Cl ch3 ch3 <br><br>
,C1 <br><br>
-CH—CH—CH=C CH H H Permethrin <br><br>
H3cXcH3 ^C1 <br><br>
CH <br><br>
-CH—CH—CH=C CH H H Phenothrin <br><br>
-3- '-3 "3 <br><br>
It is understood that formula I as used herein covers all <br><br>
I <br><br>
V <br><br>
O <br><br>
* 7 - " <br><br>
-8- <br><br>
The preferred acids are optionally substituted aliphatic carboxylic acids having a pKa value between 0.6 and 6. Suitable acids are citric acid, acetic acid, malonic acid, propionic acid, lactic acid, malic acid and the like. Either one single acid or a combination of 5 acids may be used. The acid(s) should be selected to minimize any irritation to the animal and maximize stability. <br><br>
Preferred acids are acetic, propionic and citric acid. <br><br>
The solvents selected for the formulations of the invention may be known insecticidal solvents. Selection is based on the following 10 criteria: <br><br>
a) ability to dissolve the active ingredients, and the stabilizing acid(s), <br><br>
b) ability to facilitate the spread of the pyrethroid across the skin surface of the target species, <br><br>
15 c) abil-ity to facilitate penetration of the levamisole through the skin of the target species, <br><br>
d) avoidance of significant adverse skin reactions on the target species, <br><br>
e) avoidance of troublesome properties such as toxicity, <br><br>
20 inflammability, unacceptable odour, high freezing point. <br><br>
The solvent choice for c) and d) will depend on the target species. Solvent system with no drawbacks on cattle may not be acceptable for treatment of sheep, and vice-versa. Also, it is unlikely that one single solvent will meet all the above criteria. 25 Among suitable solvents for selection are ether-alcohols such as butyl dioxitol, monoterpenes containing hydrocarbon and ether functions such as eucalyptus oil and terpinolene, and polar oxygenated solvents such as dimethyl sulfoxide and dimethylformamide. In order to stabilize the formulation it may be advantageous to 30 include in small quantity an appropriate anti-oxidant, e.g. an alkylated phenol such as BHT (butylated hydroxy toluene) or BHA (butylated hydroxy anisole). <br><br>
35 <br><br>
As an example, the ingredients can be dissolved in one or more ether-alcohols of the formula R1 <br><br>
I <br><br>
HO—(CH_-CH-0) -R 2 m wherein mis 1, 2 or 3, R is C -C alkyl and R. is hydrogen or lb j. <br><br>
methyl. <br><br>
One suitable ether-alcohol is 2-(2-butoxyethoxy)ethanol wherein m is 2 and R = ethyl. The solvent may comprise a major part of this ether-alcohol which exhibits excellent spreading and absorption characteristics. <br><br>
Although the compositions according to the invention may contain either tetramisole or levamisole or a mixture of both as an active ingredient, the use of levamisole is definitely preferred. <br><br>
The concentration of the active ingredients in the formulation will depend on their parasiticidal potency, the nature of the animal to be treated, the parasites to be controlled and the desired volume to be poured on to the animal. For levamisole a normal dose will usually be in the range of 5-15 mg/kg of liveweight. Suitable pour-on formulations according to the subject invention will appropriately contain from about 4 to about 20% of levamisole. <br><br>
The concentration of the pyrethroid of formula I in the formulation will largely depend on its anti-parasitic potency but will in general be from about 0.5 to about 10%. <br><br>
According to a second aspect, there is provided by the subject invention a method of controlling parasites in non-human animals by applying to the animal a pour-on or spot-on formulation according to the first aspect. <br><br>
The following examples are intended to illustrate and not to limit the scope of the present invention. <br><br>
1 09*^ 1 <br><br>
-10- <br><br>
EXPERIMENTAL PART <br><br>
Example I <br><br>
A pour-on formulation is prepared by mixing the following ^ ingredients: <br><br>
levamisole 10 g deltamethrin 2 g citric acid 20 g acetic acid 10 g jq 2-(2—butoxyethoxy)ethanol balance to 100 ml. <br><br>
The formulation is stable for at least 6 months <br><br>
Example II <br><br>
A pour-on formulation is prepared by mixing the following J j ingredients: <br><br>
levamisole 10 g cyhalothrin 2 g citric acid 20 g acetic acid 10 g <br><br>
2q dimethyl sulfoxide balance to 100 ml. <br><br>
The formulation is stable for at least 6 months <br><br>
Example III <br><br>
A pour-on formulation is prepared by mixing the following ingredients: <br><br>
levamisole 8 g deltamethrin 1 g malonic acid 20 g <br><br>
BHT 1 g <br><br>
2Q dimethyl sulfoxide balance to 100 ml. <br><br>
The formulation is stable for at least 6 months <br><br>
Example IV <br><br>
A pour-on formulation is prepared by mixing the following ingredients s <br><br></p>
</div>
Claims (24)
1. A pour-on composition for combating parasitic infestations in warm-blooded/ non-human animals, which comprises in admixture: i) an anti-ectoparasitic amount of a pyrethroid having the formula wherein:<br><br> Y is hydrogen or cyano; R is hydrogen or halo;<br><br> Q is CH or N; and L is a radical of the formula a) -CH— CH-CH=C<br><br> \ 2<br><br> ^ t»<br><br> R<br><br> wherein: R* is halo or lower alkyl, and<br><br> 2<br><br> R is halo, lower alkyl, halophenyl or trifluoromethyl;<br><br> R<br><br> 4<br><br> b)<br><br> •CH - CH—CH-of wherein each of R3, R^, R^ and R^ is halo c)<br><br> -CH—C<br><br> or<br><br> -13-<br><br> e)<br><br> 13 wherein n is 0 or 1, r' is halo, trifluoromethyl or<br><br> 14 difluoromethoxy, and q<br><br> 15 R is hydrogen or halo;<br><br> 1 2<br><br> 16 provided that when said R is hydrogen and said R and R are<br><br> 17 both chloro, then said Q is N;<br><br> 18 ii) an anthelmintic amount of levamisole or tetramisole or a mixture<br><br> 19 thereof;<br><br> 20 iii) at least one optionally substituted carboxylic acid having a pKa<br><br> 21 value in the range of 0.6 to 6, said acid or acids being present<br><br> 22 in a proportion of at least 1.5 acid equivalents per mole of<br><br> 23 levamisole and/or tetramisole; and<br><br> 24 iv) a solvent.<br><br> 1
2. A pour-on composition according to claim 1 wherein the<br><br> 2 synthetic pyrethroid is a °f-cyanopyrethroid.<br><br> 1
3. A pour-on composition according to either of claims 1 arid 2<br><br> 2 containing levamisole as an anthelmintic active ingredient.<br><br> 1
4. A pour-on composition according to any one of claims 1 to 3<br><br> 2 wherein said pyrethroid is deltamethrin.<br><br> 1
5. A pour-on composition according to any one of claims 1 to 3<br><br> 2 wherein said pyrethroid is cyhalothrin.<br><br> 1
6. A pour-on composition according to any one of claims 1.to 3<br><br> 2 wherein said pyrethroid is cyfluthrin.<br><br> 1
7. A pour-on composition according to any one of claims 1 to 3<br><br> 2 wherein said pyrethroid is flumethrin.<br><br> 1
8. A pour-on composition according to any one of claims 1 to 3<br><br> 2 wherein said pyrethroid is cypothrin.<br><br> 1
9. A pour-on composition according to any one of claims 1 to 3<br><br> 2 wherein said pyrethroid is fenvalerate.<br><br> N.Z. PATci'il '":T i<br><br> 1 1 NOV 1 jC6<br><br> RECEIVED 1<br><br> -14-<br><br> 200781<br><br> G<br><br>
10. A pour-on composition according to any one of claims 1 to<br><br> 9 which comprises from 4 to 20% (w/v) of levamisole.<br><br>
11. A pour-on composition according to any one of claims 1 to<br><br> 10 which comprises from 0.5 to 10% (w/v) of the pyrethroid.<br><br>
12. A pour-on composition according to any one of claims 1 to<br><br> 11 wherein said carboxylic acid is present in a proportion of at least 2.5 acid equivalents per mole of levamisole and/or tetramisole.<br><br>
13. A pour-on composition according to any one of claims 1 to<br><br> 12 wherein said carboxylic acid is acetic acid.<br><br>
14. A pour-on composition according to any one of claims 1 to 12 wherein said carboxylic acid is citric acid.<br><br>
15. A pour-on composition according to any one of claims 1 to<br><br> 12 wherein said carboxylic acid is a mixture of acetic acid and citric acid.<br><br>
16. A pour-on composition according to any one of claims 1 to<br><br> 15 wherein said solvent comprises a major part of 2-(2-butoxyethoxy)-ethanol.<br><br>
17. A pour-on composition according to any one of claims 1 to 15 wherein said solvent essentially consists of 2-(2-butoxyethoxy)-ethanol.<br><br>
18. A pour-on composition according to any one of claims 1 to<br><br> 15 wherein said solvent comprises a major proportion of monoterpenes containing hydrocarbon and ether functions.<br><br>
19. A pour-on composition according to any one of claims 1 to<br><br> 15 wherein said solvent comprises a major proportion of dimethyl sulfoxide .<br><br>
20. A method of controlling parasites in non-human animals by applying to the skin or fleece of the animal by a pour-on or spot-on method a formulation according to any one of the preceding claims.<br><br>
21. A method according to claim 20 wherein said animals are cattle.<br><br>
22. A method according to claim 20 wherein said animals are sheep.<br><br>
23. A composition according to claim 1 substantially as described herein and with reference to the examples.<br><br>
24. A method acccording to claim 20 for controlling parasites in and on non-human animals as described and using the compositions exemplified and described.<br><br> WEST-WALKER, McOABS<br><br> 1 1 MOV 1936 ><br><br> </p> </div>
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB838327761A GB8327761D0 (en) | 1983-10-17 | 1983-10-17 | Parasiticidal formulations |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ209781A true NZ209781A (en) | 1987-01-23 |
Family
ID=10550332
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ209781A NZ209781A (en) | 1983-10-17 | 1984-10-04 | Pour-on parasiticidal compositions |
Country Status (5)
Country | Link |
---|---|
AU (1) | AU565495B2 (en) |
GB (2) | GB8327761D0 (en) |
IE (1) | IE56159B1 (en) |
NZ (1) | NZ209781A (en) |
ZA (1) | ZA848072B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2696318B1 (en) * | 1992-10-01 | 1995-12-22 | Daniel Sincholle | NEW MEDICINAL PRODUCTS OR BODY HYGIENE FOR THE ELIMINATION OF BODY, HAIR AND SCALP PESTS, CONTAINING A COMBINATION OF INSECTICIDES AND ANTI-OXIDANT SUBSTANCES. |
AU2009292044B2 (en) * | 2008-09-12 | 2014-05-08 | Corteva Agriscience Llc | Stabilized pesticidal compositions |
NZ622869A (en) * | 2014-03-24 | 2015-01-30 | Donaghys Ltd | Stable veterinary anthelmintic formulations |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4278684A (en) * | 1980-06-17 | 1981-07-14 | Janssen Pharmaceutica N.V. | Non-toxic anthelminthic pour-on composition |
AU550754B2 (en) * | 1981-11-27 | 1986-04-10 | Pitman-Moore Australia Limited | Levamisole and cyhalothrin compositions |
FR2523444B1 (en) * | 1982-03-16 | 1987-07-24 | Wellcome Australia | LOCALLY APPLIED PEST CONTROL FORMULA FOR MAMMALS CONTAINING A COMBINATION OF A PYRETHROID AND A THIAZOLE |
AU1611383A (en) * | 1982-07-02 | 1984-01-05 | Robert Young & Company Limited | Pesticidal formulation with cypermethrin |
-
1983
- 1983-10-17 GB GB838327761A patent/GB8327761D0/en active Pending
-
1984
- 1984-09-14 GB GB08423263A patent/GB2148119B/en not_active Expired
- 1984-10-04 NZ NZ209781A patent/NZ209781A/en unknown
- 1984-10-16 ZA ZA848072A patent/ZA848072B/en unknown
- 1984-10-16 IE IE2650/84A patent/IE56159B1/en not_active IP Right Cessation
- 1984-10-16 AU AU34281/84A patent/AU565495B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AU3428184A (en) | 1985-04-26 |
ZA848072B (en) | 1986-05-28 |
GB8327761D0 (en) | 1983-11-16 |
AU565495B2 (en) | 1987-09-17 |
IE56159B1 (en) | 1991-05-08 |
IE842650L (en) | 1985-04-17 |
GB2148119A (en) | 1985-05-30 |
GB8423263D0 (en) | 1984-10-17 |
GB2148119B (en) | 1987-04-08 |
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