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 an external antiparasitic device, in particular a collar, for pets, in particular for dogs and cats, active against ectoparasites of these animals, in particular fleas and ticks.
• the invention relates mainly to fleas of the genus Ctenocephalides, in particular C. felis and C. canis, and ticks, in particular of the genus Rhipicephalus, in particular sanguineus, as well as chiggers (Trombicula automnalis), which are mites attacking mainly hunting dogs.
• Collars have long been produced for the elimination of common ectoparasites from dogs and cats.
• These necklaces consist of a matrix, usually a plastic matrix, incorporating between 5 and 40% of active substance and capable of releasing it over time. These collars are therefore theoretically intended to provide lasting protection.
• the collars do not have the effectiveness required in the field to ensure the actual elimination of these parasites.
• the cause may be the low activity of the active substance included in the matrix.
• Another cause may be the accelerated degradation of these active substances under the influence of climatic factors, such as light, heat, rain.
• the control of the release of the active substance from the matrix is greatly overestimated.
• the release is generally difficult and variable, it can depend strongly on the manufacturing conditions which may vary from one batch to another, and the conditions of use, in particular climatic variations and in particular the humidity and temperature, etc.
• only a relatively small amount of the active ingredient incorporated is actually released and it proves difficult to want to control and optimize the release.
• Patent applications WO-A-87/03781 and EP-A-0295 117 have proposed insecticides from the N-phenylpyrazole family. These substances are described as being active against a very large number of parasites encountered in various fields, namely agriculture, public health, human and veterinary medicine. In the latter area, these substances can act in particular against fleas and ticks from pets, such as cats and dogs. These substances can be applied in different ways, namely by the oral, parenteral, percutaneous or topical route.
• EP-A-0 295 117 and EP-A-0 500 209 propose a composition for slow release which can be put in the form of a necklace or ear loops to fight against harmful insects.
• Such a formulation may comprise from 0.5 to 25% of active material, from 75 to 99.5% of polyvinyl chloride and a catalytic amount of a plasticizer, dioctyl phthalate.
• French patent application FR-A-2 713 889 describes a pesticidal composition containing an insect growth regulator and an N-aryldiazole derivative chosen from derivatives 4- (2-bromo-1,2,2,2- tetrafluoroethyl) -1- (3 ⁇ chloro-5-trifluoromethylpyridine-2-yl) -2-methylimidazole, 5-amino-3-cyano-1- (2, 6-dichloro-4-trifluoromethylphenyl) -4- trifluoro ethylsulfinylpyrazole and 5-amino-3-cyano-l- (2,6-dichloro - 4 - trifluor ome thylpheny l) - 4 - trifluoromethylthiopyrazole.
• compositions target a large number of insects in different fields, and various types of formulations.
• the dog flea and the cat flea are targeted.
• this document lists the resinous preparations which can be put in the form of pesticide collars for animals.
• the compounds according to the invention very lipophilic and with high vapor pressure (low volatility) have a very strong affinity for the sebum which usually covers the animal's coat (skin and hair) so that this compound, upon release, is taken up by this sebum, as a result of which there is a translocation phenomenon ensuring distribution of active substance throughout the body of the animal.
• these active substances are concentrated in the sebaceous glands which become a reservoir ensuring a very long efficiency and making it possible to compensate for the absence of the collar, by releasing the active substance by passive diffusion.
• the present invention therefore relates to a collar or other external flea and anti-tick device for pets, in particular for dogs and cats, made of a matrix in which is incorporated from 0.1 to 40% by weight. , with respect to the collar, of an active substance against ectoparasites such as fleas and ticks, formed of at least one compound corresponding to the following formula (I):
• R L 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 5 and R 6 independently represent the hydrogen atom or an alkyl, haloalkyl, C (O) alkyl, alkoxycarbonyl, S (0) 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 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 1X and R 12 represent, independently of one another, a hydrogen or halogen atom, or optionally CN or N0 2 ;
• R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S (0) q CF 3 or SF 5 group ; m, n, q, r represent, independently of one another, an integer equal to 0, 1 or 2;
• Ri 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 (0) 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 radical. or haloalkyl
• 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) q CF 3 or SF S 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; with the proviso that, when R x is methyl, then R 3 is haloalkyl, R t is NH 2 , R u is Cl, R 13 is CF 3 , and X is N.
• R x is CN.
• R u is a halogen atom as well as those in which R 13 is haloalkyl, preferably CF 3 .
• 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 and R 12 are independently one on the other a halogen atom, and / or
• R 13 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) very particularly preferred in the invention is l- [2,6-Cl 2 4-CF 3 phenyl] 3-CN 4- [SO-CF 3 ] 5-NH 2 pyrazole, hereinafter referred to as -after compound A.
• the compound (I) and in particular the compound A is present in the collar at a rate of 2 to 6% by weight, more particularly from 2, 5 to 5% by weight.
• any other insecticide which we deem useful can be presented in the same matrix as the compound according to the invention.
• dies usually used for making collars can be used.
• matrices based on PVC polyvinyl chloride
• the plasticizers can in particular be chosen from adipates, phthalates, phosphates and citrates.
• plasticizers will preferably be added to the PVC, in particular chosen from the following compounds: - diethyl phthalate
• a PVC matrix will be used in the presence of a residual primary plasticizer and a secondary plasticizer, in particular according to EP-A-0 539 295 and EP-A-0 537 998.
• a secondary plasticizer in particular according to EP-A-0 539 295 and EP-A-0 537 998.
• the secondary plasticizers can quote the following products:
• external device in the sense of this invention means any device that can be attached externally to the animal to perform the same function as the collar.
• collars or other external devices By acting on the concentration and / or the composition of the matrix, it is possible to produce collars or other external devices according to the invention ensuring effective and long-lasting protection against fleas.
• collars or other external devices By acting on the concentration and / or the composition of the matrix, it is possible to produce collars or other external devices according to the invention ensuring effective and long-lasting protection against ticks.
• the present invention also relates to a method of eliminating ectoparasites, in particular fleas and ticks, from pets such as dogs and cats, in which at least one collar or other external device is attached to the animal in accordance with the invention and the animal is provided with effective long-term protection against these parasites, even in the event of removal of the collar or other external device.
• the duration indications have been given above.
• the collar or external device after its first application, remains on the animal for at least 24 hours so that enough active substance is passed over the animal and that the sebaceous glands may have stored this active substance.
• the objective of this method is non-therapeutic and in particular relates to the cleaning of animal hair and skin by elimination of the parasites which are present as well as their residues and excrements. The treated animals thus present a more pleasant coat to the eye and to the touch.
• the invention also relates to such a method for therapeutic purposes, intended to treat and prevent parasitic diseases having pathogenic consequences.
• the present invention also relates to the use of a compound corresponding to formula I for the production of a collar or other external device intended to be attached to a pet, in particular dogs and cats, capable of ensuring a prevention and treatment of fleas and ticks with a high degree of effectiveness and over a period exceeding 6 months against fleas and 3 months against ticks, the efficacy preferably being maintained for several weeks in the event of withdrawal or loss of the collar or external device or variation in release of compound (I) from the collar or external device.
• the devices described above are targeted.
• the compound of formula I is incorporated in an amount of 0.1 to 40% by weight, preferably from 1 to 15% by weight, in a matrix intended to form the collar or other external device.
• this compound will be incorporated in an amount of 1.25 to 10% by weight, in particular from 2 to 6% and more preferably still from 2.5 to 5%.
• the use according to the invention aims to produce collars or external devices having, against fleas, an efficiency greater than 95%, or even greater than 98 or 99%.
• the desired efficiency exceeds 80% or 90%.
• the use according to the invention aims, against fleas, to obtain a long-term efficacy greater than or equal to 12 months and even 18 months.
• this duration is more than 12 months, or even more than 15 months.
• the use according to the invention aims to the production of collars or other external devices making it possible to obtain an efficiency maintained in the absence of the collar or external device over a period ranging from 2 to 3 months, or more, against fleas and from 1 to 2 months, or more, against ticks.
• Formulation 1 PVC 50.0% stabilizer 0.5% epoxidized soybean oil ... 5.0% diiso octyl adipate 34.5% compound A 10.0%
• Formulation 2 PVC 50.0% stabilizing 0.5% epoxidized soybean oil .... 5.0% 2-ethylhexyldiphenyl .... phosphate 34.5% compound A 10.0% (% by weight).
• Dogs Collar with 10% of compound A - formulation 2. Dogs are infested with approximately 100 + 10 cat fleas Ctenocephalides felis (Unfed cat fleas in English) and 50 + 2 ticks Rhipicephalus sanguineus (Brown dog tick in English).
• the treatment follows the following general scheme: DAY -2 infestation with fleas and ticks. 0 fitting necklaces. 2 comb count of fleas and ticks.
• the collars were removed on D 149 on dogs 363 and 289, on D 177 for dogs 87 and 300 and on D 205 for dogs 256 and 335.
• the concentrations on the hairs of active substance according to the invention obtained at times J 205 and J 261 are presented in Tables 1 and 2 respectively, in ⁇ g / g of hair.
• the active substance concentrations are still detectable 16 weeks after removing the collar and are still effective at this time.
• Tables 3, 4 and 5 allow a correlation, concentration / activity.
• the minimum effective concentrations (on the coat) against fleas and ticks are determined at approximately: - 20 micrograms per gram of coat for ticks - 1 microgram per gram of coat for fleas.
• Control group collar without active substance.
• the necklaces were produced with the same ingredients as formulation 2 of Example 1, with the addition of a pigment (titanium dioxide).
• Tables 6 and 7 show the average efficacy results.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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• 1997
  • 1997-03-17 GR GR970100097A patent/GR1002899B/el not_active IP Right Cessation
  • 1997-03-24 IE IE970230A patent/IE970230A1/en not_active IP Right Cessation
  • 1997-03-25 AR ARP970101179A patent/AR013061A1/es not_active Application Discontinuation
  • 1997-03-26 AT AT0900297A patent/AT503494A1/de not_active Application Discontinuation
  • 1997-03-26 BR BRPI9702151-2A patent/BR9702151B1/pt active IP Right Grant
  • 1997-03-26 AU AU25128/97A patent/AU2512897A/en not_active Abandoned
  • 1997-03-26 HU HU9900833A patent/HU228751B1/hu unknown
  • 1997-03-26 FR FR9703707A patent/FR2746586B1/fr not_active Expired - Lifetime
  • 1997-03-26 JP JP53294197A patent/JP3553609B2/ja not_active Expired - Lifetime
  • 1997-03-26 CH CH02789/97A patent/CH694420A5/fr not_active IP Right Cessation
  • 1997-03-26 WO PCT/FR1997/000540 patent/WO1997036484A1/fr active IP Right Grant
  • 1997-03-26 GB GB9724482A patent/GB2316871B/en not_active Expired - Lifetime
  • 1997-03-26 SK SK1602-97A patent/SK283234B6/sk not_active IP Right Cessation
  • 1997-03-26 CN CNB971902828A patent/CN1225167C/zh not_active Expired - Lifetime
  • 1997-03-26 DE DE19780441T patent/DE19780441B3/de not_active Expired - Lifetime
  • 1997-03-26 NZ NZ329123A patent/NZ329123A/xx not_active IP Right Cessation
  • 1997-03-26 IL IL12210197A patent/IL122101A/xx not_active IP Right Cessation
  • 1997-03-26 CZ CZ0351197A patent/CZ296848B6/cs not_active IP Right Cessation
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  • 1997-03-27 BE BE9700273A patent/BE1010476A3/fr active
  • 1997-03-28 IT IT97TO000269A patent/IT1291702B1/it active IP Right Grant
  • 1997-04-14 TW TW086104769A patent/TW491701B/zh not_active IP Right Cessation
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  • 1997-11-25 MX MX9709093A patent/MX9709093A/es unknown
  • 1997-11-26 LU LU90175A patent/LU90175B1/fr active
  • 1997-11-27 FI FI974349A patent/FI121843B/fi not_active IP Right Cessation
  • 1997-11-27 NO NO19975471A patent/NO323971B1/no not_active IP Right Cessation
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