WO1997036486A1 - Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins - Google Patents
Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins Download PDFInfo
- Publication number
- WO1997036486A1 WO1997036486A1 PCT/FR1997/000542 FR9700542W WO9736486A1 WO 1997036486 A1 WO1997036486 A1 WO 1997036486A1 FR 9700542 W FR9700542 W FR 9700542W WO 9736486 A1 WO9736486 A1 WO 9736486A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- haloalkyl
- radical
- compound
- formula
- Prior art date
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
Definitions
- the present invention relates to a skin solution for direct deposition, containing an antiparasitic product and intended to be applied topically to cattle and sheep.
- the main ones are ticks of the genus Boophilus, among which we can cite the species microplus (in English cattle tick), decoloratus and anulatus.
- the other main parasites of cattle and sheep are listed in descending order of importance:
- - myases such as Dermatobia hominis (called Berne in Brazil), and Cochlyomia hominivorax (butchery lucilia); sheep myases, such as Lucilia sericata, Lucilia cuprina (called blowfly strike in Australia, New Zealand, South Africa). These are flies for which the larva constitutes the parasite of the animal.
- Ticks especially Boophilus microplus, are very closely related to the pasture where they live and are particularly difficult to control.
- WO-A-87/3781, EP-A-295 117 and EP-A-500 209 describe a class of insecticides which are derivatives of N-phenyl-pyrazoles. These compounds are said to have activity against a very large number of parasites, including Boophilus microplus, in fields as varied as agriculture, public health and veterinary medicine.
- Topical administration includes in particular oral formulations, baits, dietary supplements, skin solutions (pour-on), spray solutions (sprays), baths, showers, jets, powders, greases, shampoos, creams, etc.
- Pour-on type skin solutions are intended for percutaneous administration.
- Examples 9 of EP-A-295 117 and 291 of EP-A-500 209 describe a skin solution of the pour-on type containing 15% insecticide and 85% dimethyl sulfoxide, for percutaneous administration of the insecticide.
- EP-A-296 381 also describes pyrazole compounds with insecticidal activity in the field of agriculture, public health and veterinary medicine. Boophilus microplus is one of the many targets cited. Again, the forms of administration are very numerous and include, for example, solutions, emulsions, suspensions, powders, pastes, granules, aerosols.
- the problem is to find an effective way perfectly suited to the fight against parasites of cattle and sheep, in particular ticks, especially Boophilus microplus, in cattle and in particular lice and blowfly in sheep, under the conditions of breeding of these animals.
- Boophilus microplus for cattle by means of a particular topical formulation. She also found that this formulation was effective against lice in sheep and so-called "bowfly" flies in sheep.
- the present invention therefore aims to provide a new composition which is perfectly effective against Boophilus microplus and also against all of the other parasites described above, such as in particular lice and "bowfly" of sheep, a composition which is perfectly suited to the fight against these parasites under the conditions of breeding of these animals.
- Another object of the invention is to provide such a formulation which has a long duration of effectiveness, preferably greater than or equal to two months.
- Another objective of the invention is to provide such a formulation which is simple and rapid to use, perfectly compatible with use on herds comprising a large number of animals.
- Another objective of the invention is to provide such a formulation which is particularly suitable for extensive breeding in pasture and in use intended to protect the animals during the grouping and finishing period (Feed Lot in the USA), namely the final breeding period in which a large number of animals are grouped together in a small area enclosure over an average period of two months before slaughter.
- the present invention therefore relates to a skin solution for direct deposition, intended for the elimination of parasites from cattle and sheep, especially ticks, in particular from Boophilus microplus in cattle and lice and blowfly in sheep, comprising 0.05 to 25% w / v, based on the total solution, of a compound of formula (I)
- R is CN or methyl or a halogen atom
- R 2 is S (0) n R 3 or 4, 5-dicyanoimidazol 2-yl or haloalkyl;
- R 3 is alkyl or haloalkyl;
- R s and R 6 independently represent the hydrogen atom or an alkyl, haloalkyl, C (O) alkyl, alkoxycarbonyl, S (O) r CF 3 radical; or R 5 and R 6 may together form a divalent alkylene radical which may be interrupted by one or two divalent heteroatoms, such as oxygen or sulfur;
- R 7 represents an alkyl or haloalkyl radical
- R 8 represents an alkyl or haloalkyl radical or a hydrogen atom
- R represents an alkyl radical or a hydrogen atom
- R 10 represents a phenyl or heteroaryl group optionally substituted by one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano, or alkyl;
- R u and R 12 represent, independently of one another, a hydrogen or halogen atom, or optionally CN or N0 2 , -
- R, 3 represents a halogen atom or a haloalkyl, haloalkoxy, S (0) q CF, or SF 5 group ; m, n, q, r represent, independently of one another, an integer equal to 3, 1 or 2;
- R L is CN or methyl;
- R 2 is S (0-) n R 3 ;
- R 3 is alkyl or haloalkyl
- R 5 and R 6 independently represent the hydrogen atom or an alkyl, haloalkyl, C (O) alkyl, S (O) r CF 3 radical; or R 5 and R s may together form a divalent alkylene radical which may be interrupted by one or two divalent heteroatoms, such as oxygen or sulfur;
- R 7 represents an alkyl or haloalkyl radical;
- R 8 represents an alkyl or haloalkyl radical or a hydrogen atom
- R 9 represents an alkyl radical or a hydrogen atom
- R 10 represents a phenyl or heteroaryl group optionally substituted by one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano, or alkyl;
- R u and R 12 represent, independently of one another, a hydrogen or halogen atom
- R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S (0), - CF 3 or SF 5 group ; m, n, q, r represent, independently of one another, an integer equal to 0, 1 or 2;
- X represents a trivalent nitrogen atom or a C- R 12 radical, the other three valences of the carbon atom being part of the aromatic ring; provided that when R ⁇ is methyl, then R 3 is haloalkyl, R 4 is NH ,, R. t . is Cl, R 13 is CF 3 , and X is N.
- low concentrations of 0.05 to 10% weight / volume, more particularly from 0.1 to 2%. Optimally, it is between 0.25 and 1.5%, especially around 1%.
- skin solution for deposit means a ready-to-use solution intended to be applied topically locally on the animal, preferably on the back of the animal and at several points or in along the back line, and applied in low volume, preferably from 5 to 20 ml per 100 kg, preferably of the order of 10 ml per 100 kg, with a total volume of 10 to 150 ml per animal, preferably limited to 50 ml.
- the compound acts by simple contact, the parasite impregnating the compound on contact with the hairs and the skin.
- the solution according to the present invention is applied topically, in low volume, on the back of the animal.
- the dose of compound of formula (I) is preferably between 0.1 and 2 mg / kg (animal weight), preferably between 0.25 and 1.5 mg / kg and in particular of the order of 1 mg / kg.
- R L is CN.
- R u is a halogen atom as well as those in which R 13 is haloalkyl, preferably CF 3 .
- the compounds combining two or more of these characteristics will advantageously be retained.
- a preferred class of compounds of formula (I) consists of the compounds such that R x is CN, R 3 is haloalkyl, preferably CF 3 , or ethyl, R 4 is NH 2 , R n and R 12 are independently the on the other a halogen atom and / orRp is haloalkyl.
- the alkyl radicals of the definition of the compounds of formulas (I) generally contain from 1 to 6 carbon atoms.
- the ring formed by the divalent alkylene radical representing R 5 and R 6 as well as the nitrogen atom to which R 5 and R 6 are attached, is generally a 5, 6 or 7-membered ring.
- a compound of formula (I) which is very particularly preferred in the invention is l- [2,6-Cl a 4-CF 3 phenyl] 3-CN 4- [SO-CF 3 ] 5-NH 2 pyrazole, hereinafter referred to as after compound A.
- This compound A will be used in particular at a rate of 0.1 to 2% by weight, more particularly of the order of 1%, relative to the total solution.
- the solutions according to the invention advantageously oily generally comprise a diluent or vehicle and also a solvent (organic solvent) of the compound of formula (I) if the latter is not soluble in the diluent.
- organic solvent which can be used in the invention, mention may in particular be made of: acetyltributyl citrate, fatty acid esters such as dimethylester, diisobutyl adipate, acetone, acetonitrile, benzyl alcohol, butyldiglycol, dimethylacetamide, dimethylformamide, n-butyl ether of dipropylene glycol, ethanol, isopropanol, methanol, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, monomethylacetamide, monomethyl ether of dipropylene glycol, liquid polyoxyethylene glycols, propylene glycol, 2-pyrrolidone, in particular N-methyl pyrrolidone, diethyleneglycol monoe
- vehicle or diluent there may be mentioned in particular: vegetable oils such as soybean, peanut, castor oil, corn, cotton, olive, grape seed, sunflower oil, etc. ; mineral oils such as petrolatum, paraffin, silicone, etc. ; aliphatic or cyclic hydrocarbons, or even for example medium chain triglycerides (C8 to C12 in particular).
- vegetable oils such as soybean, peanut, castor oil, corn, cotton, olive, grape seed, sunflower oil, etc.
- mineral oils such as petrolatum, paraffin, silicone, etc.
- aliphatic or cyclic hydrocarbons or even for example medium chain triglycerides (C8 to C12 in particular).
- An emollient and / or spreading and / or film-forming agent preferably chosen from:
- polyvinylpyrrolidone polyvinyl alcohols, copolymers of vinyl acetate and vinylpyrrolidone, polyethylene glycols, benzyl alcohol, mannitol, glycerol, sorbitol, polyoxyethylenated sorbitan esters; lecithin, sodium carboxymethylcellulose, silicone oils, polydiorganosiloxane oils, in particular polydimethylsiloxane oils (PDMS), for example silanol or 45V2 oil functionalities, anionic surfactants such as alkaline stearates, especially sodium, potassium or ammonium; calcium stearate, triethanolamine stearate sodium abietate; alkyl sulfates, especially sodium lauryl sulfate and sodium cetyl sulfate; sodium dodecylbenzenesulfonate, sodium dioctylsulfosuccinate; fatty acids, especially those derived from coconut oil, -
- nonionic surfactants such as sorbitan esters, optionally polyoxyethylenes, in particular Polysorbate 80, polyoxyethylenated alkyl ethers; polyoxypropylated fatty alcohols such as polyoxypropylene-15-stearyl ether; polyethylene glycol stearate, polyoxyethylenic castor oil derivatives, polyglycerol esters, polyoxyethylenated fatty alcohols, polyoxyethylenated fatty acids, copolymers of ethylene oxide and propylene oxide, - amphoteric surfactants such that the substituted lauryl compounds of betaine; or a mixture of at least two of them.
- sorbitan esters optionally polyoxyethylenes, in particular Polysorbate 80, polyoxyethylenated alkyl ethers; polyoxypropylated fatty alcohols such as polyoxypropylene-15-stearyl ether; polyethylene glycol stearate, polyoxyethylenic castor oil derivatives
- the solvent will be used in proportion to the concentration of compound I and its solubility in this solvent.
- compound A has a solubility of 4.3% w / V in acetyl tributyl citrate. We will try to have the lowest possible volume.
- the vehicle is the 100% complement.
- the emollient is preferably used at a rate of 0.1 to 10%, in particular 0.25 to 5% by volume.
- the present invention also relates to a process for eliminating parasites from cattle and sheep, in particular from Boophilus microplus, using a skin solution for direct deposition according to the present invention, so as to obtain a long-term effectiveness. duration and broad spectrum, the solution being applied to the back of the animal, preferably following the back line or at several points.
- the method consists in applying the solution to the animals in the pasture and / or before their entry into the pasture, the application being preferably renewed every month, preferably every two months.
- the method consists in applying the solution to the animals before they enter the "Feed Lot", this application possibly being the last before the animals are slaughtered.
- the method can also consist in combining these two embodiments, namely the first follow-up of the second.
- the efficiency advantageously makes it possible to stop any application from 1 to 3 months before slaughter, in particular between 1.5 and 2.5 months, more particularly approximately 2 months before slaughter.
- the solutions according to the invention can be applied using any means known per se, preferably using an applicator gun or a dosing bottle.
- the aim of the method is non-therapeutic and in particular to clean the skin and the hair of the animals by eliminating the parasites which are present there as well as their residues and excrements. As a result, the animals are no longer stressed by the parasites and their bites, which has positive consequences for example on their growth and on the use of their food ration.
- Another object of the invention is a therapeutic method using the external device according to the invention, intended for the treatment and prevention of parasitoses having pathogenic consequences.
- the present invention also relates to the use of compounds I, in particular compound A, for the manufacture of a skin solution for direct deposition comprising the compound (I) in a small volume and designed to release the compound (I) on the skin and hair for a contact action against parasites of cattle and sheep, in particular ticks of cattle, such as Boophilus microplus, and Bowfly and lice of sheep.
- the use according to the invention aims at the production of skin solutions as described above.
- FIG. 1 is a graph showing the effectiveness, against Boophilus microplus, of skin solutions according to the invention, loaded at 0.25%, 0.5% and 1%, relative to a control, this graph comprising, in abscissa, the time in day after application of the skin solutions and, on the ordinate on the left the number of ticks counted on the animals to which the skin solutions according to the invention are applied and, on the ordinate on the right, the number of ticks counted in the controls ;
- FIG. 2 is a graph showing the tick population in the animals having received the placebo according to the example
- Compound A is dissolved in the solvent before being mixed with the other ingredients.
- a placebo was produced, differing from the skin solutions according to the invention by the absence of compound A.
- the dose volume was applied to the back line of the animal, from the head to the base of the tail.
- the following table indicates the values recorded, the weight of the animals and the dose of skin solution or placebo which will be applied to each of these animals.
- a dose-dependent effect is obtained with an efficiency of 100% for the skin solution according to the invention with 1% of compound A.
- the less concentrated solutions nevertheless give remarkable results.
- Table 2 below indicates, for each group the weight of the animals, the dose of skin solution received and the dose of active substance applied.
- composition of these solutions is the same as for the previous examples.
- the cattle were previously infested so as to present all the stages of Boophilus microplus (infestation with 5,000 larvae, 22 days, 15 days and 8 days before application of the skin solution).
- the cattle After application of the skin solutions, the cattle are still infested with the larvae from week to week, for 13 weeks, in order to determine the effectiveness of the three concentrations.
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9702162A BR9702162A (pt) | 1996-03-29 | 1997-03-26 | Solução cutánea para aplicação direta para utilização antiparasit ria em bovinos e ovinos |
GB9725003A GB2318512B (en) | 1996-03-29 | 1997-03-26 | Direct pour-on skin solution for antiparasitic use in cattle and sheep |
DE19780396T DE19780396B3 (de) | 1996-03-29 | 1997-03-26 | Direkt auf die Haut aufzubringende Lösung zur Parasitenbekämpfung bei Rindern und Schafen |
CA002222675A CA2222675C (fr) | 1996-03-29 | 1997-03-26 | Solution pour application directement sur la peau a usage anti-parasitaire chez les bovins et ovins |
AT0900497A AT504042A1 (de) | 1996-03-29 | 1997-03-26 | Direkt auf die haut aufzubringende lösung zur parasitenbekämpfung bei rindern und schafen |
AU25130/97A AU2513097A (en) | 1996-03-29 | 1997-03-26 | Solution for direct application on the skin for controlling cattle and sheep parasites |
SE9704303A SE523761C2 (sv) | 1996-03-29 | 1997-11-24 | Oljelösning för lokal applicering i liten volym på huden hos nötboskap eller får för eliminering av parasiter samt användning därav |
LU90177A LU90177B1 (fr) | 1996-03-29 | 1997-11-26 | Solution cutanée pour dépôt direct à usage anti-parasitaire chez les bovins et ovins |
NO19975473A NO324071B1 (no) | 1996-03-29 | 1997-11-27 | Opplosning for direkte pahelling pa huden for a kontrollere kveg- og saueparasitter og anvendelse derav. |
FI974353A FI119042B (fi) | 1996-03-29 | 1997-11-27 | Suoraan iholle levitettävä liuos käytettäväksi loisia vastaan nautakarjalla ja lampailla |
DKPA199701363A DK177400B1 (da) | 1996-03-29 | 1997-11-27 | Opløsning af og anvendelse af 1-[2,6-C12-4-CF3-phenyl]-3-CN-4-[SO-CF3]-5-NH2-pyrazol til fremstilling af opløsningen til direkte anbringelse på huden til eliminering af parasitter fra kvæg og får |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR96/04209 | 1996-03-29 | ||
FR9604209A FR2746595B1 (fr) | 1996-03-29 | 1996-03-29 | Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins |
US69217896A | 1996-08-05 | 1996-08-05 | |
US08/692,178 | 1996-08-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997036486A1 true WO1997036486A1 (fr) | 1997-10-09 |
Family
ID=26232632
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1997/000542 WO1997036486A1 (fr) | 1996-03-29 | 1997-03-26 | Solution cutanee pour depot direct a usage anti-parasitaire chez les bovins et ovins |
Country Status (20)
Country | Link |
---|---|
AT (2) | AT504042A1 (fr) |
AU (1) | AU2513097A (fr) |
BE (1) | BE1010483A5 (fr) |
BR (1) | BR9702162A (fr) |
CA (1) | CA2222675C (fr) |
CH (1) | CH692894A8 (fr) |
DE (1) | DE19780396B3 (fr) |
DK (1) | DK177400B1 (fr) |
ES (1) | ES2143389B1 (fr) |
FI (1) | FI119042B (fr) |
FR (1) | FR2747015B1 (fr) |
GB (1) | GB2318512B (fr) |
GR (1) | GR1002910B (fr) |
IE (1) | IE970215A1 (fr) |
IT (1) | IT1291699B1 (fr) |
LU (1) | LU90177B1 (fr) |
NL (1) | NL1005673C2 (fr) |
NO (1) | NO324071B1 (fr) |
SE (1) | SE523761C2 (fr) |
WO (1) | WO1997036486A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6075043A (en) * | 1996-12-05 | 2000-06-13 | Pfizer Inc. | Parasiticidal pyrazoles |
WO2001040446A1 (fr) * | 1999-12-02 | 2001-06-07 | Lilly Co Eli | Formulations de deversement |
WO2001095723A1 (fr) * | 2000-06-15 | 2001-12-20 | Ssl International Plc | Composition parasiticide |
WO2002050042A2 (fr) * | 2000-12-21 | 2002-06-27 | Bayer Aktiengesellschaft | Utilisation d'oximes de pyrazole pour lutter contre les parasites |
US7435753B2 (en) | 2003-12-18 | 2008-10-14 | Pfizer Limited | Substituted arylpyrazoles |
US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006061537A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
Citations (6)
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EP0045424A1 (fr) * | 1980-08-02 | 1982-02-10 | Bayer Ag | Formulations "pour-on" actives contre les tiques |
EP0295117A1 (fr) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Dérivés de N-phénylpyrazoles |
EP0296381A1 (fr) * | 1987-06-12 | 1988-12-28 | Bayer Ag | Méthylamino-5-aryl-1 pyrazoles substitués |
EP0412849A2 (fr) * | 1989-08-10 | 1991-02-13 | AgrEvo UK Limited | Azoles comme pesticides |
EP0500209A1 (fr) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | 1-(2-Pyridyl)pyrazoles pesticides |
WO1996016544A2 (fr) * | 1994-11-30 | 1996-06-06 | Rhone-Poulenc Agrochimie | Composition emulsionnable destinee a la lutte contre les insectes |
Family Cites Families (4)
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GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
DE4414333A1 (de) * | 1994-04-25 | 1995-10-26 | Bayer Ag | Substituierte Pyridylpyrazole |
-
1997
- 1997-03-20 IE IE970215A patent/IE970215A1/en not_active IP Right Cessation
- 1997-03-26 DE DE19780396T patent/DE19780396B3/de not_active Expired - Lifetime
- 1997-03-26 WO PCT/FR1997/000542 patent/WO1997036486A1/fr active IP Right Grant
- 1997-03-26 AT AT0900497A patent/AT504042A1/de not_active Application Discontinuation
- 1997-03-26 GR GR970100110A patent/GR1002910B/el not_active IP Right Cessation
- 1997-03-26 CH CH02791/97A patent/CH692894A8/fr not_active IP Right Cessation
- 1997-03-26 CA CA002222675A patent/CA2222675C/fr not_active Expired - Lifetime
- 1997-03-26 AU AU25130/97A patent/AU2513097A/en not_active Abandoned
- 1997-03-26 GB GB9725003A patent/GB2318512B/en not_active Expired - Lifetime
- 1997-03-26 ES ES009750029A patent/ES2143389B1/es not_active Expired - Fee Related
- 1997-03-26 FR FR9703708A patent/FR2747015B1/fr not_active Expired - Lifetime
- 1997-03-26 BR BR9702162A patent/BR9702162A/pt active IP Right Grant
- 1997-03-27 NL NL1005673A patent/NL1005673C2/nl not_active IP Right Cessation
- 1997-03-27 IT IT97TO000260A patent/IT1291699B1/it active IP Right Grant
- 1997-03-27 BE BE9700276A patent/BE1010483A5/fr active
- 1997-11-24 SE SE9704303A patent/SE523761C2/sv not_active IP Right Cessation
- 1997-11-26 LU LU90177A patent/LU90177B1/fr active
- 1997-11-27 DK DKPA199701363A patent/DK177400B1/da not_active IP Right Cessation
- 1997-11-27 NO NO19975473A patent/NO324071B1/no not_active IP Right Cessation
- 1997-11-27 FI FI974353A patent/FI119042B/fi not_active IP Right Cessation
-
2009
- 2009-09-04 AT ATA1395/2009A patent/AT506843B1/de not_active IP Right Cessation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0045424A1 (fr) * | 1980-08-02 | 1982-02-10 | Bayer Ag | Formulations "pour-on" actives contre les tiques |
EP0295117A1 (fr) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Dérivés de N-phénylpyrazoles |
EP0296381A1 (fr) * | 1987-06-12 | 1988-12-28 | Bayer Ag | Méthylamino-5-aryl-1 pyrazoles substitués |
EP0412849A2 (fr) * | 1989-08-10 | 1991-02-13 | AgrEvo UK Limited | Azoles comme pesticides |
EP0500209A1 (fr) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | 1-(2-Pyridyl)pyrazoles pesticides |
WO1996016544A2 (fr) * | 1994-11-30 | 1996-06-06 | Rhone-Poulenc Agrochimie | Composition emulsionnable destinee a la lutte contre les insectes |
Non-Patent Citations (1)
Title |
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"EXTENDED EFFICACY SPECTRUM OF AZOLE PESTICIDES", RESEARCH DISCLOSURE, no. 380, 1 December 1995 (1995-12-01), pages 802, XP000549823 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6075043A (en) * | 1996-12-05 | 2000-06-13 | Pfizer Inc. | Parasiticidal pyrazoles |
US6268509B1 (en) | 1996-12-05 | 2001-07-31 | Pfizer Inc | Parasiticidal pyrazoles |
WO2001040446A1 (fr) * | 1999-12-02 | 2001-06-07 | Lilly Co Eli | Formulations de deversement |
WO2001040446A3 (fr) * | 1999-12-02 | 2002-01-17 | Lilly Co Eli | Formulations de deversement |
WO2001095723A1 (fr) * | 2000-06-15 | 2001-12-20 | Ssl International Plc | Composition parasiticide |
WO2002050042A2 (fr) * | 2000-12-21 | 2002-06-27 | Bayer Aktiengesellschaft | Utilisation d'oximes de pyrazole pour lutter contre les parasites |
WO2002050042A3 (fr) * | 2000-12-21 | 2002-11-28 | Bayer Ag | Utilisation d'oximes de pyrazole pour lutter contre les parasites |
US7435753B2 (en) | 2003-12-18 | 2008-10-14 | Pfizer Limited | Substituted arylpyrazoles |
US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
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