EP0112878A1 - Parasiticidal formulations - Google Patents

Parasiticidal formulations

Info

Publication number
EP0112878A1
EP0112878A1 EP19830902112 EP83902112A EP0112878A1 EP 0112878 A1 EP0112878 A1 EP 0112878A1 EP 19830902112 EP19830902112 EP 19830902112 EP 83902112 A EP83902112 A EP 83902112A EP 0112878 A1 EP0112878 A1 EP 0112878A1
Authority
EP
European Patent Office
Prior art keywords
formulation according
formulation
cypermethrin
levamisole
uherein
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19830902112
Other languages
German (de)
French (fr)
Inventor
John Mckeller Ballany
Andrew Galbraith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Robert Young & Co Ltd
Original Assignee
Robert Young & Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Robert Young & Co Ltd filed Critical Robert Young & Co Ltd
Publication of EP0112878A1 publication Critical patent/EP0112878A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles

Definitions

  • This invention relates to parasiticidal formulations which are useful in eradicating and/or controlling both endo- and ectoparasites which attack warm-blooded non-human animals.
  • animals such as sheep and cattle can be simultaneously infested under certain conditions uith both endoparasites, including for example helminths such as gut and lungw ⁇ rms and ectoparasites including for example lice, keds, mites, ticks and fleas.
  • helminths such as gut and lungw ⁇ rms
  • ectoparasites including for example lice, keds, mites, ticks and fleas.
  • known insecticides are selective in being either endoparasiticidal or ectoparasiticidal and if it is desired to control both types of parasite then separate applications of the insecticides are usually necessary.
  • cypermethrin NRDC 149
  • NRDC 149 whose preparation is described in UK patent No. 1,413,491.
  • the term cypermethrin is used herein to embrace all isomers of: ⁇ - cyano -3-phenocyphenyl (-) -cis, trans -2,2- dimethyl-3-(2, 2-dichloro ⁇ inyl) -cydopropanecarboxylate
  • cypermethrin as a pour-on formulation for controlling ectoparasites and blowfly myiasis is described in our copending application No. 8205879.
  • tetramisole (2,3,5,6 - tetrahydro-6-phenylimidazo-2, 1-6thiazole) and its laevo isomer levamisole.
  • Tetramisole and levamisole are described in UK patent No. 1,043,489.
  • a further object is to provide a pour-on or spot-on endo- and ectoparasiticidal formulation of cypermethrin and levamisole (or tetramisole) 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.
  • a parasiticidal formulation which comprises a mixture of items (i) to (iii) below in a suitable solvent: (i) cypermethrin, (ii) levamisole, and (iii) an amount of a soluble acid effective in retarding or preventing decomposition of either
  • parasites are meant to include endo parasites, e.g. gut and lungworms, as well as ectoparasites, e.g. lice, keds, mites, ticks, fleas, blowfly.
  • controlling parasites is meant to include the interference with the development and/or the reproduction of said parasites.
  • unimpaired efficacy means that the formulations have an efficacy which is unimpaired in comparison with the efficacy of two compositions comprising the same amount of levamisole and cypermethrin separately.
  • useful efficacy means that the formulations have an efficacy greater than mixture which has undergone decomposition but less than unimpaired efficacy.
  • tetramisole may be used or a mixture of tetramisole and levamisole.
  • the preferred acids are optionally substituted aliphatic carb ⁇ xylic acids, either single acids or combinations of one or more and preferably having a pKa value in the range from 0.6 to 6.0.
  • Suitable acids are citric acid, acetic acid and malonic acid.
  • the acid(s) should be selected to minimise any irritation to the animal and maximise stability.
  • the solvents selected for the formulations of the invention may be known insecticidal solvents.
  • Selection is based on the criteria:- a) ability to dissolve both actives, and the stabilising acids, b) ability to facilitate the spread of the cypermethrin across the skin surface of the target species, c) ability to facilitate penetration of the levamisole through the skin of the target species, d) avoidance of significant adverse skin reactions on the target species, e) avoidance of troublesome properties such as toxicity, inflammability, unacceptable odou , high freezing point.
  • the solvent choice for c) and d) will depend on the target species as a 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.
  • etheralcohols such as butyl dioxitol, monoterpenes containing hydrocarbon and ether functions such as eucalyptus oil and terpinolene, and polar oxygenated solvents such as dimethyl sulphoxide and dimethylformamide.
  • BHT butylated hydroxy toluene
  • ingredients can be dissolved in one or more alcohols of formula:-
  • the solvent may comprise & majror part of this alcohol which exhibits excellent spreading and absorbtion characteristics.
  • Cypermethrin will be used in most instances at between 21 ⁇ 2-10 mg/kg liveweight, depending on the species and parasite, with levamisole used at 5-15 mg/kg liveweight. This gives guidance on choice of active ratio and concentrations as below:- Active Ratio
  • Cypermethrin/Levamisole will normally be used between the ratios 1:4 and 1:1, depending on the species and the parasite under attack. Concentration
  • Solubility may again impose limits, but up to
  • the mixture formed a clear homogenous solution, effective in controlling both ectoparasites and endoparasites on cattle, and without sign of unuanted side effects. Stability indications were satisfactory, and shelf-life expectation is high.
  • the active ratio may be 1 cypermethrin: 2 levamisole.
  • a maximum concentration may be 10% w/v cypermethrin:
  • the solvent may include oxygenated compounds such as glycols, ethers and esters. Acid proportions may be up to 20% w/v for malonic or citric acid and up to 10% w/v acetic acid.

Abstract

Une formule parasiticide et une méthode de contrôle des endo et/ou ectoparasites sur des animaux comprennent de la cyperméthrine et du levamisol dans un solvant approprié et dans lequel on ajoute un acide soluble pour stabiliser le mélange contre la décomposition pendant le stockage. On peut utiliser par exemple l'acide acétique ou l'acide malonique.A parasiticidal formula and a method for controlling endo and / or ectoparasites in animals include cypermethrin and levamisol in a suitable solvent and in which a soluble acid is added to stabilize the mixture against decomposition during storage. One can use for example acetic acid or malonic acid.

Description

TITLE
Parasiticidal Formulations
This invention relates to parasiticidal formulations which are useful in eradicating and/or controlling both endo- and ectoparasites which attack warm-blooded non-human animals.
It is accepted that animals such as sheep and cattle can be simultaneously infested under certain conditions uith both endoparasites, including for example helminths such as gut and lungwαrms and ectoparasites including for example lice, keds, mites, ticks and fleas.
In general, known insecticides are selective in being either endoparasiticidal or ectoparasiticidal and if it is desired to control both types of parasite then separate applications of the insecticides are usually necessary.
Among the class of synthetic pyrethroids which are effective in controlling ectoparasites is cypermethrin (NRDC 149) whose preparation is described in UK patent No. 1,413,491. The term cypermethrin is used herein to embrace all isomers of: α - cyano -3-phenocyphenyl (-) -cis, trans -2,2- dimethyl-3-(2, 2-dichloroυinyl) -cydopropanecarboxylate The use of cypermethrin as a pour-on formulation for controlling ectoparasites and blowfly myiasis is described in our copending application No. 8205879.
One effective and preferred endoparasiticidal, and more specifically anthelmintic, compound is tetramisole (2,3,5,6 - tetrahydro-6-phenylimidazo-2, 1-6thiazole) and its laevo isomer levamisole. Tetramisole and levamisole are described in UK patent No. 1,043,489.
It is becoming increasingly important to be able to control parasistes by pour-on or spot-on formulations wherein the active compound is 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. There are many advantages in such applications which are well documented.
In order to reduce the number of separate insecticide applications, for economy and convenience, it is desirable to produce a parasiticidal formulation that is effective in simultaneously controlling endo- and ectoparasites. It would normally be expected that a mixture of cypermethrin and levamisole (or tetramisole) would effectively control both such species of parasite.
Indeed we have found this effect in a combination of the two compounds in a suitable solvent. Ue have also however found that such a mixture begins to decompose after storage for a period of approximately 6 months storage at room temperature. Some reaction is taking place whereby the efficacy of the mixture is reduced as compared to the same quantity of individual ingredients.
It is therefore an object of this invention to provide a formulation of cypermethrin and levamisole (or tetramisole) that is stable for longer than 5 months by preventing or at least retarding any decomposition of the individual active ingredients.
A further object is to provide a pour-on or spot-on endo- and ectoparasiticidal formulation of cypermethrin and levamisole (or tetramisole) 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.
According to one aspect of this invention there is provided a parasiticidal formulation which comprises a mixture of items (i) to (iii) below in a suitable solvent: (i) cypermethrin, (ii) levamisole, and (iii) an amount of a soluble acid effective in retarding or preventing decomposition of either
(i) or (ii). According to a second aspect, there is provided 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. The term "parasites" is meant to include endo parasites, e.g. gut and lungworms, as well as ectoparasites, e.g. lice, keds, mites, ticks, fleas, blowfly.
The term "controlling parasites" is meant to include the interference with the development and/or the reproduction of said parasites.
The term "unimpaired efficacy" means that the formulations have an efficacy which is unimpaired in comparison with the efficacy of two compositions comprising the same amount of levamisole and cypermethrin separately.
The term "useful efficacy" means that the formulations have an efficacy greater than mixture which has undergone decomposition but less than unimpaired efficacy.
In place of item (ii) tetramisole may be used or a mixture of tetramisole and levamisole.
The preferred acids are optionally substituted aliphatic carbαxylic acids, either single acids or combinations of one or more and preferably having a pKa value in the range from 0.6 to 6.0. Suitable acids are citric acid, acetic acid and malonic acid. The acid(s) should be selected to minimise any irritation to the animal and maximise stability. The solvents selected for the formulations of the invention may be known insecticidal solvents. Selection is based on the criteria:- a) ability to dissolve both actives, and the stabilising acids, b) ability to facilitate the spread of the cypermethrin across the skin surface of the target species, c) ability to facilitate penetration of the levamisole through the skin of the target species, d) avoidance of significant adverse skin reactions on the target species, e) avoidance of troublesome properties such as toxicity, inflammability, unacceptable odou , high freezing point. The solvent choice for c) and d) will depend on the target species as a 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.
Among suitable solvents for selection are etheralcohols such as butyl dioxitol, monoterpenes containing hydrocarbon and ether functions such as eucalyptus oil and terpinolene, and polar oxygenated solvents such as dimethyl sulphoxide and dimethylformamide. BHT (Butylated hydroxy toluene) can be included in small quantities as a stabiliser and peroxide scavenger.
As an example the ingredients can be dissolved in one or more alcohols of formula:-
HO - (CH2-CH2-O)m-R wherein m = 1,2 or 3 and R = C1-C6 alkyl.
One suitable alcohol is 2- (2-butσxyethoxy ) ethanol wherein m = 2 and R = ethyl. The solvent may comprise & majror part of this alcohol which exhibits excellent spreading and absorbtion characteristics.
Cypermethrin will be used in most instances at between 2½-10 mg/kg liveweight, depending on the species and parasite, with levamisole used at 5-15 mg/kg liveweight. This gives guidance on choice of active ratio and concentrations as below:- Active Ratio
Cypermethrin/Levamisole will normally be used between the ratios 1:4 and 1:1, depending on the species and the parasite under attack. Concentration
Solubility imposes an upper limit but 10% Cyper methrin/20% Levamisole is a practical upper level, uith lower levels of 2% Cypermethrin/4% Levamisole in particular for sheep. Concentrations lower than these are unlikely for reasons of cost and dose size. Acid Content
Solubility may again impose limits, but up to
20% incorporation is possible for malonic and citric acids, uith 10% being the practical limit for acetic acid.
The following examples illustrate (1) decomposition and (2) inhibition (prevention as opposed to retardation) of decomposition.
Example 1
A solution was made of levamisole (10% w/v) and cypermethrin (10% to w/v) in 2- (2-butoxyethoxy ) ethanol.
After 5 months storage at ambient temperatures the solution uas quantitatively analysed and found to contain the initial proportions of levamisole and cypermethrin.
After 9 months the solution uas again analysed and the cypermethrin level had fallen to 2% w/v. Example 2
A solution was made of levamisole (10% w/v) and cypermethrin (10% w/v) in a solvent mixture of citr ic acid (20% w/v), acetic acid (10% w/v) and 2- (2-butoxyethoxy ) ethanol (balance to 100% volume). Analysis after 5 and 9 and 12 months showed the initial proportions of levamisole and cypermethrin still remaining. Example 3
A mixture was made up as fallows :- Cypermethrin 4% Levamisole base 8% Malonic acid 20% BHT 1%
Dimethylsulphoxide balance
The mixture formed a clear homogenous solution, effective in controlling both ectoparasites and endoparasites on cattle, and without sign of unuanted side effects. Stability indications were satisfactory, and shelf-life expectation is high.
In formulations according to the invention, the active ratio may be 1 cypermethrin: 2 levamisole. A maximum concentration may be 10% w/v cypermethrin:
20% w/v levamisole with 2½% w/v: 5% w/v useful in controlling sheep parasites. The solvent may include oxygenated compounds such as glycols, ethers and esters. Acid proportions may be up to 20% w/v for malonic or citric acid and up to 10% w/v acetic acid.
Ue have surprisingly found that (l) a mixture of levamisole and cypermethrin in a solvent is liable to decompose after 6 months storage at ambient temperatures, the rate of decomposition rapidly increasing thereafter and (2) the decomposition can be inhibited or prevented to prolong the effective shelf life to practical values by adding one or more soluble aliphatic carboxylic acids.

Claims

Claims
1. A parasiticidal formulation comprising in admixture; i) Cypermethrin ii) Levamisole or tetramisole or a mixture thereof, iii) An amount of a soluble acid effective to retard or prevent decomposition of either i) or ii), and iv) A solvent.
2. A formulation according to claim 1, uherein the soluble acid is optionally substituted aliphatic carboxylic acid, either a single acid or combinations of one or more acids.
3. A formulation according to claim 2, uherein the acids have a pKa value betueen 0.6 to 6.0.
4. A formulation in accordance with any preceding claim, uherein the acid is citric, acetic or malonic.
5. A formulation according to claim 1, uherein the acid has a minimal irritational effect on the skin of an animal for uhich the formulation is intended to be used, and a maximal effect of stabilisation of the formulation.
6. A formulation according to any preceding claim, uherein the solvent is selected to fulfil the follouing:- a) ability to dissolve both actives, and the stabilising acids, b) ability to facilitate the spread of the cypermethrin across the skin surface of the target species, c) ability to facilitate penetration of the levamisole through the skin of the target species.
7. Formulation according to any preceding claim, wherein the solvent is selected from ether alcohols, preferably butyl dioxitol,monoterpenes containing hydrocarbon and ether functions, preferably eucalyptus oil and terpinolene, and polar oxygenated solvents, preferably dimethyl sulphoxide and dimethylformamide.
8. Formulation according to any preceding claim , wherein butylated hydroxy toluene is included in small quantities as a stabiliser and peroxide scavenger.
9. Formulation according to any preceding claim , wherein the ratio between cypermethrin and levamisole/tetramisole is between 1:4 and 1:1.
10. Formulation according to any preceding claim, wherein the concentration in solution is between 2 and 10% cypermethrin and 4 and 20% levamisole.
11. Formulation according to any preceding claim, uherein the soluble acid content is betueen 10 and 20%.
12. 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.
13. A method in accordance uith claim 12, uherein the effective dosage of the application is betueen 2.5 and 15 mg/Kg cypermethrin/liveueight, and betueen 5 and 10 mg/Kg levamisole or tetramisole/liveueight.
14. A formulation intended for the purposes herein set forth as herein described and exemplified.
15. A method for controlling parasites on non-human animals as described herein and using the formulations exemplified and described.
EP19830902112 1982-07-02 1983-06-30 Parasiticidal formulations Withdrawn EP0112878A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8219104 1982-07-02
GB8219104 1982-07-02

Publications (1)

Publication Number Publication Date
EP0112878A1 true EP0112878A1 (en) 1984-07-11

Family

ID=10531425

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19830902112 Withdrawn EP0112878A1 (en) 1982-07-02 1983-06-30 Parasiticidal formulations

Country Status (6)

Country Link
EP (1) EP0112878A1 (en)
AU (1) AU1611383A (en)
GB (1) GB2122902B (en)
IE (1) IE55205B1 (en)
NZ (1) NZ204735A (en)
WO (1) WO1984000095A1 (en)

Families Citing this family (11)

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Publication number Priority date Publication date Assignee Title
AU2314184A (en) * 1983-01-10 1984-07-12 Robert Young & Company Limited Endoparasiticidal composition containing levamisole
GB8327761D0 (en) * 1983-10-17 1983-11-16 Janssen Pharmaceutica Nv Parasiticidal formulations
US4710083A (en) * 1984-10-29 1987-12-01 Johann Wolf Gesellschaft M.B.H. Kg Nailing plate for the production of compound supports, and compound support
GB8515459D0 (en) * 1985-06-19 1985-07-24 Young Robert Co Ltd Parasitical compositions
HU207944B (en) * 1988-08-09 1993-07-28 Chinoin Gyogyszer Es Vegyeszet Process for producing veterinary composition against endoparazites
DE9012996U1 (en) * 1990-09-12 1991-10-10 Perycut Chemie Ag
CN1044960C (en) * 1996-09-18 1999-09-08 中国农业科学院植物保护研究所 Matrine-cybermethrin mixed preparation and its production method
ES2157811B1 (en) 1998-07-29 2002-03-16 Sumitomo Chemical Co PREPARED INSECTICIDE ACUOSO FOR THERMAL FUMIGATION.
US6340672B1 (en) 2000-02-16 2002-01-22 Phoenix Scientific, Inc. Parasiticidal formulation and a method of making this formulation
US8178500B2 (en) * 2008-09-12 2012-05-15 Dow Agrosciences Llc Pesticidal compositions
KR101702337B1 (en) * 2008-12-26 2017-02-03 다우 아그로사이언시즈 엘엘씨 Stable sulfoximine-insecticide compositions

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NL131034C (en) * 1964-05-11
GB1413491A (en) * 1972-05-25 1975-11-12 Nat Res Dev 3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters their preparation and their use in pesticidal compositions
IT1123122B (en) * 1979-09-12 1986-04-30 Montedison Spa INSECTICIDE LIQUID COMPOSITIONS CONTAINING SYNTHETIC PYRETROIDS
US4278684A (en) * 1980-06-17 1981-07-14 Janssen Pharmaceutica N.V. Non-toxic anthelminthic pour-on composition
DE3029426A1 (en) * 1980-08-02 1982-03-11 Bayer Ag, 5090 Leverkusen AGAINST EFFECTIVE POUR-ON FORMULATIONS
GB2094626B (en) * 1981-03-16 1985-02-20 Young Robert Co Ltd Insecticidal control of ectoparasites
GB2095107A (en) * 1981-03-24 1982-09-29 Janssen Pharmaceutica Nv Tetramisole-or levamisole pour-on compositions
CH654720A5 (en) * 1981-09-03 1986-03-14 Ciba Geigy Ag STORAGE-RESISTANT MOTH PROTECTION FORMULAS.

Non-Patent Citations (1)

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Title
See references of WO8400095A1 *

Also Published As

Publication number Publication date
GB8316960D0 (en) 1983-07-27
NZ204735A (en) 1986-04-11
AU1611383A (en) 1984-01-05
WO1984000095A1 (en) 1984-01-19
IE831546L (en) 1984-01-02
GB2122902A (en) 1984-01-25
IE55205B1 (en) 1990-07-04
GB2122902B (en) 1985-05-01

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