IE56159B1 - Parasiticidal formulations - Google Patents
Parasiticidal formulationsInfo
- Publication number
- IE56159B1 IE56159B1 IE2650/84A IE265084A IE56159B1 IE 56159 B1 IE56159 B1 IE 56159B1 IE 2650/84 A IE2650/84 A IE 2650/84A IE 265084 A IE265084 A IE 265084A IE 56159 B1 IE56159 B1 IE 56159B1
- Authority
- IE
- Ireland
- Prior art keywords
- pour
- composition according
- pyrethroid
- levamisole
- acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 238000009472 formulation Methods 0.000 title claims abstract description 34
- 230000000590 parasiticidal effect Effects 0.000 title description 5
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims abstract description 36
- 229960001614 levamisole Drugs 0.000 claims abstract description 36
- 239000004540 pour-on Substances 0.000 claims abstract description 35
- 239000002728 pyrethroid Substances 0.000 claims abstract description 19
- 239000005892 Deltamethrin Substances 0.000 claims abstract description 10
- 229960002483 decamethrin Drugs 0.000 claims abstract description 10
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims abstract description 10
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims abstract description 6
- 229960001591 cyfluthrin Drugs 0.000 claims abstract description 4
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims abstract description 4
- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims abstract description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims abstract 4
- CWUDZUQQZDXUHF-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 2,2-dimethylspiro[cyclopropane-3,1'-indene]-1-carboxylate Chemical compound C1=CC2=CC=CC=C2C11C(C)(C)C1C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 CWUDZUQQZDXUHF-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 244000045947 parasite Species 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 230000000507 anthelmentic effect Effects 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 241000283690 Bos taurus Species 0.000 claims description 3
- 241001494479 Pecora Species 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 230000001178 anti-ectoparasitic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000003071 parasitic effect Effects 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 abstract description 8
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 241000894007 species Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000001984 ectoparasiticidal effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004544 spot-on Substances 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241000243789 Metastrongyloidea Species 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 241000258242 Siphonaptera Species 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 244000079386 endoparasite Species 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- FJDPATXIBIBRIM-QFMSAKRMSA-N (1R)-trans-cyphenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-QFMSAKRMSA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- RFEJUZJILGIRHQ-XRIOVQLTSA-N 2,3-dihydroxybutanedioic acid;3-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O.CN1CCC[C@H]1C1=CC=CN=C1 RFEJUZJILGIRHQ-XRIOVQLTSA-N 0.000 description 1
- -1 2-butoxyethoxy Chemical group 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 241001608644 Hippoboscidae Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- VQHJWDTTWVEXFE-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C(Br)C(Cl)(Cl)Br)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 VQHJWDTTWVEXFE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Toxicology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Stable pour-on formulations, combining tetramisole or levamisole with a synthetic pyrethroid, which contain one or more optionally substituted aliphatic carboxylic acids having a pKa-value in the range of 0.6 to 6. The pyrethroids are e.g. deltamethrin, cyhalothrin, cyfluthrin, flumethrin, cypothrin and fenvalerate.
Description
This invention relates to parasiticidal formulations which are useful in eradicating and/or controlling both endo- and ectoparasites attacking warm-blooded non-human animals· Animals like sheep and cattle are often simultaneously infected 5 by both endoparasites, such as gut and lungworms, and ectoparasites such as, for example, lice, keds, mites, ticks and fleas.
Most parasiticidal compounds have a rather selective activity: some compounds have predominantly ectoparasiticidal activity while other compounds have predominantly endoparasiticld&l activity. In I 0 order to control both types of parasites, separate applications of an endoparasiticide and of an ectoparasiticide will generally be required.
One effective and preferred endoparasiticidal, and more specifically anthelmintic, compound is 2,3,5,6-tetrahydro-6-phenyl15 imida2o[2,l-b]thiazole, the racemic form of v/hich is generically designated as tetramisole, while the laevorotatory form; which bears most of the anthelmintic activity, is generically Indicated as levamisole. Tetramisole and levamisole are described e.g. in British Patent Nos. 1,043,489, respectively 1,152,544.
An important group of insecticides, v/hich are increasingly used ® to eradicate ectoparasites on animals, are the synthetic pyrethroids, which combine great ectoparasiticidal activity with a relatively high degree of safety towards animals and humans· Potent insecticides within the group of synthetic pyrethroids are, for example, eypermethrin, deltamethrin, cyhalothrin, flumethrin, cyfluthrin, tralomethrin, tralocythrln, fenv&ler&te, permethrin and phenothrin.
In view of the desirability to control both endo- and ectoparasites simultaneously with one treatment, it would obviously be a desirable objective to combine tetramlsole or levamlsole with an appropriate pyrethroid in one single formulation for application to the infected animals. Preferably such a formulation would be a pour-on or spot-on formulation, 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. Various anthelmintic pour-on compositions which contain levamlsole as an active ingredient are now widely used in practice. In O.K. Patent Application No. 2,110,091 A there are described certain pour-on formulations, which comprise a mixture of cyhalothrin with levamlsole or tetramlsole tree base in a carrier comprising particular combinations of an alcohol solvent with an ester co-solvent· In a preferred embodiment, tne compositions ar© taught to contain one or more carboxylic acids selected from the group consisting of C to C_ alkanoic acids. According to the 1 reference, the molar ratio of alkanoic acid to levamlsole free base should not exceed 1.1 and most preferably the alkanoic acid and levamlsole free base are in substantially equimolar proportions.
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 levamlsole, such as those described in U.K.
Patent Application No. 2.110.091 A. As a matter of fact, it has been 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 levamlsole or tetramlsole in combination with a pyrethroid and which are stable for a sufficiently long period of time, preferably at least 6 months. by preventing or et 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 levamisole or tetramisole and a 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.
As used herein, the term parasites is meant to include , endoparasites, e.g. gut and lungworms, as well as ectoparasites, e.g. lice, Reds, mites, ticks, fleas, blowfly.
The term controlling parasites is meant to include the killing * and/or the interference with the development and/or reproduction of said parasites.
The term unimpaired efficacy means that the formulations have an efficacy which is unimpaired in con^arison with the efficacy of two compositions comprising the same amount of levamisole and a synthetic pyrethroid separately.
The term useful efficacy means that the formulations have an efficacy greater than that of a mixture which has undergone decomposition but less than unimpaired efficacy.
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 carboxylic acids having a p£Sa value 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.
In principle there is no upper limit to the acid content of the formulation, but, for reasons of acceptability and lack of irritation, the acid component should not represent more than about 40% (w/v) and preferably not more than 35% (w/v) of the formulation.
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 Ϊ j .CH-O-C-L (ΐ) wherein: Y is hydrogen or cyano; R is hydrogen or halo; Q is CH or N; and L is a radical of the formula a) -CH —CH-CH«C H 3C CH3 wherein: R is halo or lower alkyl, and R2 is halo, lower alkyl, halophenyl or trifluoromethy1: b) -CH—CH—CH-C c h3c^>ch3 r3 * r6 r 4 5 6 wherein each of R , R , R and R is halo.
G wherein : n is 0 or 1, R7 is halo, trifluoromethyl or difluoromethoxy, and 8 R is hydrogen or halo; 2 provided that when said R is hydrogen and said R and R ore both chloro, then said Q is Mi ii) an anthelmintic amount of levamisole or tetramisole or a mixture thereof? 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 present in a proportion of at least 1.5 acid equivalents per mole of levamisole and/or tetramisole; and iv) a solvent.
Similar compositions containing a combination of tetramisole and/or levamisole with cypermethrin as an insecticidal active ingredient are described and claimed in VK>-84/0()()95 (GB 2122902-A), filed on June 30, 1983. The canpositions described and claimed therein are excluded from the scope of the subject invention.
Specific pyrethroids of formula (I) which can advantageously be used in compositions according to the subject invention are listed in the following Table I.
Table 1: Compounds of formula I.
L Q R Y Generic designation xcl -CH—CH-CH«C N H CN DOMCO-417 h3c^cm3C1xBr -CH—CH-CH-C CH H CN Deltamethrin Table I (cont'd) Q R Y Generic designation -CIJ—PH-CH^C χ HjC Z^'CH3 -CH—CH-CH-C χ η3<=Χ:η3 Cl CF, Cl Cl CH H CM Cyhalothrin CH F CM Cyfluthrin -CH—CH-CH-C χ h^cXsl ’3W 3 CH / 3 CH .Cl -CH—CH-CH^C λ—λ νχ,„3 'G* Br -CH—CH-CH-C..
S< I 1 Br H.Cr CH_ Br Br Br -CH—CH—CH-C X 1 |KBr H.jC^ CH.* Cl Cl ^CH3 -CH- C h^c^SchI^s H3OZ^H3 CH H CM Cyphenothrin CH F CM Fliasetbrin CH H CM Tralomethrin CH H CM Tralocythrin CH H CM Fenprop&thin CH H CM Cypothrln Table I (cont'd) isomeric forms and mixtures thereof, including geometric isomers (cis 5 and trans) and optical isomers.
Particularly potent insecticides within the group of synthetic pyrethroids are those wherein the ester group is derived from an c(-cyano alcohol, i.e. the synthetic pyrethroids of formula (I) wherein V is cyano. Pour-on compositions containing Said pyrethroids, hereinafter referred to as ^(-cyanopyrethroids, are particularly preferred within the present invention. <> The prefarrod acids are optionally substituted aliphatic carboxylic tficidis having a pKa value between 0.6 and 6» Suitable acids are, c.
Preferred acids are acetic, propionic and citric acid.
The solvents selected for the formulations of the invention may be known insecticidal solvents. Selection is based on the following criteria: a) ability to dissolve the active ingredients, and the stabilizing acid(s), b) ability to facilitate the spread of the pyrethroid across the skin surface of the target species, c) ability to facilitate penetration of the levamlsole 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 odour, high freezing point.
Th© 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.
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 stabilise the formulation it may be advantageous to include in small quantity an appropriate anti-oxidant, e.g. an alkylated phenol such as BHT (butylated hydroxy toluene) or BHA (butylated hydroxy anisole). t Ο Αβ an example, the ingredients can he dissolved in one or more ether-alcohols of the formula R1 I HO-(CH--CH-O) -R « m wherein bi is 1, 2 or 3, R is c^c^ alkyl and R^ is hydrogen or r> methyl.
One suitable ether-alcohol is 2-(2-butoxyethoxy)ethanol wherein π is 2 and R * ethyl. The solvent may comprise a major part of this ether-alcohol which exhibits excellent spreading and absorption characteristics.
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.
The concentration of the active ingredients in the formulation will depend on their parasiticidal potency, the nature of the animal I 5 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 livewelght. Suitable pour-on formulations according to the subject invention will appropriately contain from about 4 to about 20% of levamisole.
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%.
According to a second aspect, there is provided by the subject invention a method of controlling parasites in non-human animals by 2r> applying to the animal a pour-on or spot-on formulation according to the first aspect.
The following examples are intended to illustrate and not to limit the scope of the present invention· j L EXPERIMENTAL PART Example I A pour-on formulation Is prepared by mixing the following ingredients: levamlsole 10 g deltamethrin 2 g « citric acid 20 g acetic acid 10 g 2~(2-butoxyethoxy)ethanol balance to 100 ml. ' 10 The formulation is stable for at least 6 months Example II A pour-on formulation is prepared by mixing the following ingredients: levamlsole 10 g cyhalothrin 2 g citric acid 20 g acetic acid 10 g dimethyl sulfoxide balance to 100 al.
The formulation is stable for at least 6 months Example III ι A pour-on formulation is prepared by mixing the following ingredients: levamlsole 8 g deltamethrin 1 g malonic acid 20 g BUT 1 g dimethyl sulfoxide balance to 100 ml· The formulation is stable for at least 8 months <1 Example IV A pour-on formulation is prepared by mixing the following ingredients: 2 lovamisola 10 g pormethrin 2 g citric acid 20 g acetic acid 10 g dimethyl sulfoxide balance to 100 ml.
The formulation is stable for at least 6 months Example V Pour-on formulae are prepared by dissolving together: I) II) levamisole base deltamethrin butyl dioxitol levamisole base deltamethrin malonic acid butyl dioxitol g 2 g balance to 100 ml. 20 g g 20 g balance to 100 ml.
These formulations are clear straw-coloured liquids. Storage at ambient temperature gave the following results: I II Original analysis levamisole 20.5¾ 19.7% deltamethrin 2.0% 2.4% visual clear straw clear straw After 1 month levamisole 20.1¾ 19.4% deltamethrin 0.4% 2.6% visual dark amber clear straw I 3
Claims (22)
1. A pour-on composition for combsting parasitic infestations in warm-blooded, non-human animals, which comprises in admixture: i) an anti-ectoparasitic amount of a pyrethroid having the formula wherein: Y is hydrogen or cyano; R is hydrogen or halo; Q is CH or N; and L is a radical of the formula / r1 a) -CH—CH-CH«C CH, R is halo, lower alkyl, halophenyl or trifluoromethyl; H 3 4 5 6 wherein each of R , R , R and R is halo; c) 1 1 wherein n is 0 or 1, R ie halo, trifluoromethyl or dif luoromethoxy, and 8 R is hydrogen or halo; 1 2 provided that when eaid R is hydrogen and eaid R and R are both chloro, then said Q is N; ii) an anthelmintic amount of levamisole or tetramisole or a mixture thereof; iii) at least one optionally substituted carboxylic acid having a p&a value in the range of 0.6 to 6, said acid or acids being present in a proportion of at least 1.5 acid equivalents per mole of levamisole and/or tetramisole; and iv) a solvent.
2. A pour-on composition according to claim 1 wherein the synthetic pyrethroid is a ^-cyanopyrethroid.
3. « A pour-on composition according to any of claims 1 and 2 containing levamisole ae an anthelmintic active ingredient.
4. A pour-on composition according to any of claims 1 to 3 wherein said pyrethroid is deltamethrin.
5. A pour-on composition according to any of claims 1 to 3 wherein said pyrethroid is cyhalothrin.
6. A pour-on composition according to any of claims 1 to 3 wherein said pyrethroid is cyfluthrin.
7. A pour-on composition according to any of claims 1 to 3 wherein eaid pyrethroid is flumethrin.
8. A pour-on composition according to any of claims 1 to 3 wherein said pyrethroid is cypothrin.
9.O A pour-on composition according to any of claims 1 to 3 wherein said pyrethroid is fenvalerate. IS
10. A pour-on coepositloa according to any of cliains 1 which comprio©® frcs 4 to 20¾ (w/v) of levamisole.
11. A pour-on cos^oeition according to any of claims 1 to 10 which cooprleeo fzca 0.5 to 10%' (w/v) of the pyrethroid. 5
12. · A pour-on composition according to any of claims 1 to 11 wherein said carboxylic add is present in a proportion of at leaeJt 2.5 acid equivalents per mole of levamisole and/or tetramisole·
13. Ά pour-on composition according to any of claims 1 to 12 wherein said carboxylic acid is acetic acid. 10
14. A pour-on composition according to any of claims 1 to 12 wherein eaid carboxylic acid is citric acid·
15. h pour-on composition according to any of claims 1 to 12 wherein said carboxylic acid i& acetic acid and citric acid. Id. A pour-on composition according to any of claims 1 to 15 15 wherein said solvent cosaprlweti a major part of 2-(2-buto3cy@thoxy)ethanol.
16. 17. A pour-on composition according to any of claims 1 to 15 wherein said solvent essentially consists of 2“(2* j butoxy®thoxy)“ ethanol· 20 1Θ. A pour-on composition according to any of claims 1 to 15 wherein said solvent comprises a major proportion of monotsrpsne&i containing hydrocarbon and ether functions·
17. 19. h pour-on composition according to any of claims 1 to 15 wherein said solvent coapriHegw a major proportion of dimethyl 25 sulfoxide·
18. 20. Use of a formulation according to any one of the preceding claims for controlling parasites in non-human animals.
19. 21. Use according to claim 20 wherein said animals are cattle.
20. 22. Use according to claim 20 wherein said animals are sheep.
21. 23. A composition as claimed in claim 1 and substantially as described herein and with reference to the examples.
22. 24. Use as claimed in claim 20, substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838327761A GB8327761D0 (en) | 1983-10-17 | 1983-10-17 | Parasiticidal formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE842650L IE842650L (en) | 1985-04-17 |
| IE56159B1 true IE56159B1 (en) | 1991-05-08 |
Family
ID=10550332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2650/84A IE56159B1 (en) | 1983-10-17 | 1984-10-16 | Parasiticidal formulations |
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. |
| MX2011002658A (en) * | 2008-09-12 | 2011-04-07 | Dow Agrosciences 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 |
| NZ203574A (en) * | 1982-03-16 | 1986-04-11 | Wellcome Australia | Pour on compositions containing pyrethroids and thiazoles |
| 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 AU AU34281/84A patent/AU565495B2/en not_active Expired
- 1984-10-16 IE IE2650/84A patent/IE56159B1/en not_active IP Right Cessation
- 1984-10-16 ZA ZA848072A patent/ZA848072B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB8423263D0 (en) | 1984-10-17 |
| GB8327761D0 (en) | 1983-11-16 |
| NZ209781A (en) | 1987-01-23 |
| GB2148119B (en) | 1987-04-08 |
| GB2148119A (en) | 1985-05-30 |
| IE842650L (en) | 1985-04-17 |
| AU565495B2 (en) | 1987-09-17 |
| AU3428184A (en) | 1985-04-26 |
| ZA848072B (en) | 1986-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |