IE55205B1 - Parasiticidal formulations - Google Patents
Parasiticidal formulationsInfo
- Publication number
- IE55205B1 IE55205B1 IE154683A IE154683A IE55205B1 IE 55205 B1 IE55205 B1 IE 55205B1 IE 154683 A IE154683 A IE 154683A IE 154683 A IE154683 A IE 154683A IE 55205 B1 IE55205 B1 IE 55205B1
- Authority
- IE
- Ireland
- Prior art keywords
- formulation
- formulation according
- levamisole
- cypermethrin
- uherein
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 238000009472 formulation Methods 0.000 title claims abstract description 29
- 230000000590 parasiticidal effect Effects 0.000 title abstract description 4
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims abstract description 31
- 229960001614 levamisole Drugs 0.000 claims abstract description 31
- 239000005946 Cypermethrin Substances 0.000 claims abstract description 26
- 229960005424 cypermethrin Drugs 0.000 claims abstract description 26
- 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 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 244000045947 parasite Species 0.000 claims description 12
- 241000894007 species Species 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004540 pour-on Substances 0.000 claims description 5
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 4
- 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 claims description 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 claims description 4
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000004544 spot-on Substances 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229940044949 eucalyptus oil Drugs 0.000 claims description 2
- 239000010642 eucalyptus oil Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 230000003019 stabilising effect Effects 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- -1 ether alcohols Chemical class 0.000 claims 1
- 229930003658 monoterpene Natural products 0.000 claims 1
- 150000002773 monoterpene derivatives Chemical class 0.000 claims 1
- 235000002577 monoterpenes Nutrition 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000354 decomposition reaction Methods 0.000 abstract description 8
- 244000078703 ectoparasite Species 0.000 abstract description 8
- 244000079386 endoparasite Species 0.000 abstract description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- 241000238876 Acari Species 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001608644 Hippoboscidae Species 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 241000258242 Siphonaptera Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001984 ectoparasiticidal effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101001108356 Homo sapiens Nardilysin Proteins 0.000 description 1
- 208000006123 Myiasis Diseases 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 102100021850 Nardilysin Human genes 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 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 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A parasiticidal formulation and a method for control of endo and/or ectoparasites on non-human animals comprises cypermethrin and levamisole in a suitable solvent and in which the mixture is stabilised against decomposition in storage by addition of a soluble acid. Examples of acids used are acetic and malonic acid.
[GB2122902A]
Description
This invention relates to pa'rasiticidal formulations uhich are useful in eradicating and/or controlling both endo- and ectoparasites uhich attack uarm-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 lunguorms and ectoparasites including for example lice, keds, mites, ticks and fleas.
In general, knoun insecticides are selective in being either endoparasiticidal or ectoparasiticidal and t 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 uhich are effective in controlling ectoparasites is cypermethrin
British (NRDC '149) uhose preparation is described in / patent specification /No. 1,413,491. The term cypermethrin is used herein to embrace all isomers of: cC - cyano -3-phenocyphenyl {*) -cis, trans -2,2- dimethyl-3-(2,2-dichlorOvinyl) -cydopropanecarboxylate The use of cypermethrin as a pour-on formLiation for controlling ectoparasites and bloufly myiasis is described -2-
British patent in our copending/application No. 8205879, Publication No. 2,094,626A.
One effective and preferred endoparasiticidal, and more specifically anthelmintic, compound is totramisole (2,3,5,6 - tetrahydro-6-phenylimidazo-2,1-6thiazole) and its laevo isomer levamisole. Totramisole and
British specification levamisole are described in / patent /No. 1,043,489.
It is becoming increasingly important to be able to control parasistes by pour-on or spot-on formulations uherein 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 uhich are uell documented.
In or'der 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 uould normally be expected that a mixture of cypermethrin and levamisole (or tetramisole) uould effectively control both such species of parasite.
Indeed ue have found this effect in a combination of the tuo compounds in a suitable solvent. Ue have also houever 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 -3- 5 Οι id ο 5 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 6 months by preventing or at least retarding any decomposition of the individual active ingredients.
- »·. - 10 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 uhich retains useful or unimpaired efficacy against parasites after storage of the formulation for a prolonged period e.g. greater than one year·' 15
According to one aspect of this invention there is provided a parasiticidal formulation uhich comprises a mixture of items (i) to (iii) belou in a suitable solvent: (i) cypermethrin, (ii) levamisole, and (iii) an amount of a soluble acid effective in 20 retarding or preventing decomposition of either (i) or (ii).
According to a second aspect, there is provided a ecto- 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.
-4- 5 5 2 0 5
The term "parasites" is meant to include endo-parasites, e.g. gut and lunguorms, as uell as ectoparasites, e.g. lice, keds, mites, ticks, Fleas, bloufly. The term "controlling parasites" is meant to include 5 the interference uith the development and/or the reproduction of said parasites·
The term "unimpaired efficacy" means that the formulations have an efficacy uhich is unimpaired in comparison uith the efficacy of tuo compositions comprising 10 the same amount of levamisole and cypermethrin separately.
The term "useful efficacy" means that the formulations have an efficacy greater than mixture uhich has undergone decomposition but less than unimpaired efficacy.
In place of item (ii) tetramisole may be used or a 15 mixture of tetramisole and levamisole.
The preferred acids are optionally substituted aliphatic carboxylic 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 20 citric acid, acet'iC 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 knoun 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 thB 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 odour, high freezing point.
ThB solvent choice for c) and d) uill depend on the target species as a solvent system with no draubacks on cattle may not be acceptable for treatment of sheep, and vice-versa. Also it is unlikely that one single solvent uill meet all the above criteria.
Among suitable solvents for selection are ether-alcohols such as butyl dioxitol, monoterpenea containing hydrocarbon and ether functions euch as eucalyptus oil and terpinolene, and'polar oxygenated solvents such as dimethyl sulphoxide and dimethylformamide. BHT (Butylated hydroxy toluene) can be .included in small -6- quantities as a stabiliser and peroxide scavenger.
As an example the ingredients can ba dissolved in one or more alcohols of formula:-
HO - (CH2-CH2-0)m_R
wherein m = 1,2 or 3 and R = Cj-Cg alkyl.
One suitable alcohol is 2-(2-butoxyethoxy) ethanol wherein m = 2 and R = ethyl. The solvent may comprise part of this alcohol uhich exhibits excellent spreading and absorbtion characteristics. *
Cypermethrin will be used in most instances at between 2-J--10 mg/kg liveueight, depending on the species and parasite, with levamisole used at 5-15 mg/kg liveueight. This gives guidance on choice of active ratio and concentrations as belou:-Active Ratio
Cyparmethrin/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, with lower levels of 2% Cypermethrin/4$ Levamisole in particular for sheep. Concentrations lower then these are unlikely for reasons of cost and dose size.
-7- flcid Content
Solubility may again impose limits,:but up to 20$ incorporation is possible for malonic and citric acids, with 10$ being the practical limit for acetic 5 acid.
The follouing examples illustrate (l) decomposition and (2) inhibition (prevention as opposed to retardation) of decomposition.
Example 1 10 A solution uas made of levamisole (10$ u/v) and cypermethrin (10$ to u/v) in 2-(2-butoxyethoxy) athanol. 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$ u/v.
Example 2 A solution uas made of levamisole (i0$ u/v) and cypermethrin (10$ u/v) in a solvent mixture of citric 20 acid (20$ u/v), acetic acid (10$ u/v) and 2-(2-butoxyethoxy) ethanol (balance to 100$ volume). Analysis after 5 and 9 and 12 months shaued the initial proportions of levamisolB and cypermethrin still remaining.
5520 5 -B-
Example 3 A mixture uas mads up as Follous:-Cypermethrin 4$
Lavamisola base 8$
Malonic acid 20$ BHT 1$
Dimethylsulphoxide balance
The mixture Formed a clear homogenous solution, affective in controlling both ectoparasites and endoparasites on cattle, and uithout sign of unuanted side effects. Stability indications uere 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$ u/v cypermethrin: 20$ w/v levamisole with 2$$ u/v: 5$ u/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$ u/v for malonic or citric acid and up to 10$ u/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 (8)
1. 2. A formulation according to claim 1, wherein thB soluble acid is optionally substituted aliphatic carboxylic acid, either a single acid or combinations of one or more acids. 15
2. 3. A formulation according to claim 2, wherein the acids have a pKa yalue between 0.6 to 6.0.
3. 4. A formulation in accordance with any preceding claim, wherein the acid is citric, acetic or malonic. 20
4. 5. A formulation' according to claim 1, wherein the acid has a minimal irritational effect On the skin of an animal for which the formulation ie intended to be used, and a maximal effect of stabilisation of the formulation.
5. 6. A formulation according to any preceding claim, wherein the solvent is selected to fulfil the following :- a) ability to dissolve both actives, and the 25 -10- -10- 5 5 £ Ο 5 stabilising acids, b) ability to facilitate tha 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, uherein 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.
6. 8. Formulation according to any preceding claim , uherein butylated hydroxy toluene is included in small quantities as a stabiliser and peroxide scavenger. 9. formulation according to any preceding claim , uherein the ratio between cypermethrin and levamisole/ tetramisole is betueen 1:4 and 1:1. 10. formulation according to any preceding claim, uherein the concentration in solution is betueen 2 and 10^ cypermethrin and 4 and 20J& levamisole. 11. formulation according to any preceding claim, uherein the soluble acid content is betueen 10 and 20^. ecto-
7. 12. A method of controlling/parasites in non-human animals by applying ta the skin or fleece of tha animal by a pour-on or spot-on method a formulation according to any οπβ of the preceding claims. 13. ft method in accordance uith claim 12, uherein the effective dosage of the application is between 2.5 and 15 mg/Kg cypermethrin/liveueight, and betueen 5 and 10 mg/Kg levamisole or tetramisole/liveueight. 14. ft formulation intended for the purposes herein set forth ‘as herein described and exemplified. ecto- 15. ft method for controlling/parasites on non-human animals as described herein and using the formulations exemplified and described. Dated this 1st day of July 1983. BY: TOMKINS 6 CO., Applicants' Agents, (Signed)
8. 5, Dartmouth Road, > Dublin 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8219104 | 1982-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831546L IE831546L (en) | 1984-01-02 |
| IE55205B1 true IE55205B1 (en) | 1990-07-04 |
Family
ID=10531425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE154683A IE55205B1 (en) | 1982-07-02 | 1983-07-01 | 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)
| 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, Zürich | Insecticidal product |
| 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 |
| PL2334187T3 (en) * | 2008-09-12 | 2018-03-30 | Dow Agrosciences Llc | Stabilized pesticidal compositions |
| UA106363C2 (en) * | 2008-12-26 | 2014-08-26 | ДАУ АГРОСАЙЕНСИЗ, ЭлЭлСи | Stable insecticidal compositions on the basis of sulfoximine |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
-
1983
- 1983-06-21 AU AU16113/83A patent/AU1611383A/en not_active Abandoned
- 1983-06-22 GB GB08316960A patent/GB2122902B/en not_active Expired
- 1983-06-28 NZ NZ20473583A patent/NZ204735A/en unknown
- 1983-06-30 WO PCT/GB1983/000166 patent/WO1984000095A1/en not_active Ceased
- 1983-06-30 EP EP19830902112 patent/EP0112878A1/en not_active Withdrawn
- 1983-07-01 IE IE154683A patent/IE55205B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0112878A1 (en) | 1984-07-11 |
| WO1984000095A1 (en) | 1984-01-19 |
| AU1611383A (en) | 1984-01-05 |
| IE831546L (en) | 1984-01-02 |
| GB2122902B (en) | 1985-05-01 |
| GB8316960D0 (en) | 1983-07-27 |
| GB2122902A (en) | 1984-01-25 |
| NZ204735A (en) | 1986-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |