WO2001090075A1 - Compositions combattant les ectoparasites des animaux - Google Patents

Compositions combattant les ectoparasites des animaux Download PDF

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Publication number
WO2001090075A1
WO2001090075A1 PCT/JP2001/004330 JP0104330W WO0190075A1 WO 2001090075 A1 WO2001090075 A1 WO 2001090075A1 JP 0104330 W JP0104330 W JP 0104330W WO 0190075 A1 WO0190075 A1 WO 0190075A1
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group
optionally substituted
atom
composition
alkyl
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PCT/JP2001/004330
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English (en)
Japanese (ja)
Inventor
Sadanori Mizukoshi
Masayuki Morita
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Ishihara Sangyo Kaisha, Ltd.
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Priority to AU58822/01A priority Critical patent/AU5882201A/en
Publication of WO2001090075A1 publication Critical patent/WO2001090075A1/fr

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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to a composition for controlling ectoparasites of animals, which contains a specific pyridine compound or a salt thereof as an active ingredient.
  • flea adults are parasitized in mammals and birds, especially pets such as cats, and inhabit by sucking their blood for nutrients.
  • fleas infest a pet irritation and itching can make the pet frustrated, and may cause allergic dermatitis and anemia. It can also transmit a variety of pathogens.
  • it can also parasitize the owner, causing redness and rashes, with severe itching, and may cause allergies such as atopic dermatitis. Therefore, the present invention aims to provide a composition for controlling animal ectoparasites such as fleas.o
  • Y is a haloalkyl group
  • m is 0 or 1
  • Q is
  • X is an oxygen atom or a sulfur atom
  • R 1 and R 2 are each independently a hydrogen atom
  • R 12 and R 13 are each independently a hydrogen atom, an optionally substituted alkyl A alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted or a heterocyclic group which may be substituted;
  • the present invention relates to a composition for controlling ectoparasites in animals.
  • a haloalkyl group such as CH 2 CF 3, CF 2 CF have CHB r There CH 2 B r, are included.
  • a haloalkyl group having 1 to 2 carbon atoms and 1 to 5 halogen atoms is desirable, and a trifluoromethyl group is more desirable.
  • Q 1 group RR 2 , RR 4 , 7 R 80 contained in the group (hereinafter referred to as Q 1 group)
  • a secondary substituent of the optionally substituted cycloalkyl group defined as 2 , R 3 or R 4 a halogen atom; an alkoxy group; an alkylthio group; a trialkylsilyl group; a phenyl group; A phenyl group substituted with nitro or haloalkyl; a phenyl group substituted with phenoxy which may be substituted with alkoxy or alkylthio; a phenoxy group; a phenylthio group; an amino group; Cyc
  • a cycloalkyl group; an imino group; —C (W 2 ) R 14 group W 2 is an oxygen atom or a sulfur atom, and R 14 is a hydrogen atom; an amino group; an amino group substituted with one or two alkyl groups; An alkyl group; an alkoxy group; an alkylthio group; or an aryl group)
  • R 15 is an aryl group substituted with an alkyl or haloalkyl); or an alkylsulfonyl group.
  • R 15 is an aryl group substituted with an alkyl or haloalkyl
  • alkylsulfonyl group When the above substituent is an imino group, it may form an amidino group or an imidate group together with an amino group or an alkoxy group.
  • substituent of the optionally substituted alkyl group defined as R 1 or R 2 included in the group Q 1 in the general formula (I) include, for example, 4-haloalkyl-1-pyridinecarboxamido. Group, N-methyl-4-haloalkyl-13-pyridine lipoxamide group, 4-haloalkyl-13-pyridinecarboxamide N-alkylenoxy group, etc. are also included.
  • the chemical structural formulas of the general formula (I) containing these substituents are exemplified.
  • R 2 is as described above, A is — (CH 2 ), one group or one (CH 2 ) q -0- (CH 2 ) q group, and 1 is an integer of 1 to 4. And q is 1 or 2)
  • the above compound is a dimer of the compound of the general formula (I) linked by an alkylene chain or the like.
  • the active ingredient of the composition of the present invention includes a trimer based on such an idea.
  • R 4 , R 8 , R 9 , R 10 , R ′′, R 12 or R 13 included in the Q 1 group in the general formula (I)
  • the following substituents include a halogen atom; an alkyl group; an alkoxy group; a haloalkoxy group; an alkylthio group; a phenyl group which may be substituted with halogen, alkyl, alkoxy, nitro, haloalkyl or phenoxy; a phenoxy group; Groups; cycloalkyl groups; cycloalkoxy groups and the like.
  • the alkyl group or alkyl moiety contained in the group Q 1 in the general formula (I) has 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group Those having 3 or more carbon atoms may be straight-chain or branched-chain structural isomers.
  • the alkenyl group contained in the Q 1 group in the general formula (I) includes those having 2 to 6 carbon atoms, such as ethenyl, propenyl, butenyl, pentenyl, and hexenyl groups. And those having 3 or more carbon atoms may be linear or branched structural isomers.
  • Examples of the alkynyl group contained in the Q 1 group in the general formula (I) include those having 2 to 6 carbon atoms, such as an ethynyl group, a propynyl group, a petynyl group, a pentynyl group, and a hexynyl group. Those having 4 or more carbon atoms may be straight-chain or branched-chain structural isomers.
  • Examples of the cycloalkyl group included in the Q 1 group in the general formula (I) include those having 3 to 8 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.
  • R 1 and R 2 contained in the Q 1 group in the general formula (I) may be joined together to contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom.
  • Examples of the aryl group included in the Q ] group of the formula (I) include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzochenyl group, a benzofuranyl group, and a quinolinyl group.
  • the heterocyclic moiety of the optionally substituted heterocyclic group included in the Q 1 group in the general formula (I) includes a pyridyl group, a cyenyl group, a furyl group, a pyrazinyl group, a pyrimidinyl group, a tetrahydrofuranyl group, a thiazolyl group Group containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur such as isooxazolyl, quinolyl, pyrazolyl, oxazolyl, oxdiazolyl, thiadiazolyl, and triazolyl And a 7-membered monocyclic group or a phenyl-fused cyclic group.
  • the heterocyclic moiety of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes 2 to 3 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom.
  • Preferred is a 7-membered monocyclic group, specifically, a bilazolyl group, an oxazolyl group
  • 5-membered monocyclic groups such as thiazolyl, oxaziazolyl, thiadiazolyl, and triazolyl;
  • the secondary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes a halogen atom, a nitro group, an optionally substituted alkyl group, an optionally substituted alkenyl group An optionally substituted alkynyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted cycloalkyl group, a hydroxyl group, an optionally substituted alkoxy group, and an optionally substituted Alkenyloxy group, optionally substituted alkynyloxy group, optionally substituted aryloxy group, optionally substituted heterocyclic oxy group, optionally substituted cycloalkoxy group, mercapto group, optionally substituted Good alkylthio group, optionally substituted arylthio group, optionally substituted arylthio group, optionally substituted alkynylthio group, optionally substituted Riruchio group, a substituted heterocyclic ring which
  • those that may be substituted include halogen atoms; cyano groups; halogen groups that may be substituted with halogen, haloalkyl, cyano, alkoxy, aryl, and alkoxy groups that may be substituted with halogen and aryl.
  • the secondary or tertiary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I) has an alkyl group or an alkyl moiety having 1 to 6 carbon atoms, for example, Examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a hexyl group, and those having 3 or more carbon atoms may be those having a linear or branched structural isomer.
  • alkenyl group examples include those having 2 to 6 carbon atoms, such as ethenyl group, propyl group, butenyl group, pentenyl group, and hexenyl group, and those having 3 or more carbon atoms are straight or branched. It may have a structural isomer of the chain.
  • Alkynyl groups include those having 2 to 6 carbon atoms, for example, ethynyl group, propynyl group, butynyl group, pentynyl group and hexynyl group, and those having 3 or more carbon atoms are linear or branched.
  • Examples of the cycloalkyl group include those having 3 to 8 carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.
  • Examples of the aryl group include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzophenyl group, a benzofuranyl group, and a quinolinyl group.
  • heterocyclic group examples include 1 to 3 hetero atoms selected from nitrogen, oxygen and sulfur such as pyridyl, phenyl, phenyl, virazinyl, thiazolyl, isoxazolyl, and quinolyl. And a 5- or 6-membered monocyclic group or a phenyl-fused cyclic group.
  • the compound of the general formula (I) may form a salt with an acidic substance or a basic substance, and the salt with the acidic substance may be a salt such as hydrochloride, hydrobromide, phosphate, sulfate, or nitrate.
  • the salt with a basic substance may be an inorganic or organic base salt such as a sodium salt, a potassium salt, a calcium salt, an ammonium salt or a dimethylamine salt.
  • the compound of the general formula (I) or a salt thereof is described in Japanese Patent No. 2994182, JP-A-10-195072, JP-A-11-180957, W098 / 57969, W00 / 35285, W00 / 35912, W00 It can be manufactured according to the method described in / 35 913, W01 / 9104, TO01 / 14373 and the like.
  • the composition of the present invention includes: fleas; mites; lice such as lice, lice, lice, and lice; lice such as lice and lice; and lice such as lice. Although it is effective for those living on the body surface of succulent host animals, it is particularly effective in controlling fleas and mites. It is also effective against blood-sucking dipteran pests such as flies, brassicae, buyo, and sand flies.
  • Host animals for which the composition of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, egrets, ferrets, and birds (e.g., pigeons, horses, myna birds, fowls, parakeets, parakeets, And pets such as black pine, canary, etc .; livestock such as porcupines, pomas, pigs and higgies; and poultry such as ducks and chickens.
  • the compositions of the present invention are particularly effective on pets, especially dogs and cats. External parasites inhabit the host animal in the back, armpits, lower abdomen, inner thighs, etc.o
  • the above-mentioned fleas refer to ectoparasitic wingless insects belonging to the order Flea (Siphonaptera), specifically fleas belonging to the family Flea (Pulliedae), the family Flea (Ceratephyl lus) and the like.
  • the fleas belonging to the flea family include the flea (Ctenocephal i des can is), the non-flea (Ctenocephal ides lei is), the flea (Pulex irritans), the newt flea (Echidnophaga gal l inacera), and the noptosyl horre is), Yamato flea flea (Monosyl lus anisus), ⁇ ⁇ ⁇ ⁇ ° flea flea (Nosopsvl lus fasciatus) and the like.
  • the composition of the present invention is excellent in controlling fleas belonging to the family Flea among fleas, and particularly excellent in controlling fleas mainly parasitic on dogs and cats such as fleas and cats.
  • composition of the present invention includes, among the above-mentioned mites, Haemaphvsal is longicornis, Haemaphvsal is longicornis, Haemaphysa l is i apon i ca), Dermacentor ret iculatus, Dermacentor taiwanesi tick, It is especially good at controlling ticks such as Haemaphvsal is f lava), Ixodes ovatus, Ixodes persuicatus and Boophi lus micro lus.
  • the compound of the general formula (I) may be used as it is, but it can be used in the form of powders, granules, tablets, powders, capsules, premixes, liquids, emulsions, etc. together with a suitable carrier.
  • suitable carriers include those normally used in feed drugs, such as lactose, sucrose, glucose, starch, wheat flour, corn flour, Examples include soybean meal, defatted rice bran, calcium carbonate, and other commercially available feed ingredients.
  • the compound of the general formula (I) may be used together with a carrier together with various vitamins and minerals.
  • the compound of the general formula (I) can be mixed with or used in combination with other animal drugs such as antibacterial agents, nutritional agents, anthelmintic agents, fungicides, anticoccidial agents, etc., if necessary. In some cases, it has excellent effects.
  • animal drugs such as antibacterial agents, nutritional agents, anthelmintic agents, fungicides, anticoccidial agents, etc., if necessary. In some cases, it has excellent effects.
  • the following are preferred as other animal drugs that can be used in combination or in combination.
  • the composition for controlling ectoparasites in animals containing the compound of the general formula (I) and benzoyl pereas as active ingredients is a ectoparasite that can be theoretically expected when each active ingredient is mixed and used together. This is because not only does it exhibit a controlling effect (additive effect), but it also exhibits an external parasite controlling effect (synergistic effect) that cannot be predicted theoretically at a specific compounding ratio.
  • the compounding ratio of the compound of the general formula (I) to the benzoyl pereas is generally 1:60 to 60: 1, preferably 1:20 to 20: 1, more preferably 10: 1 to 1:10, Most preferably, the ratio is 5: 1 to 1: 5, and particularly preferably, the ratio is 2: 1 to 1: 2. Further, among the benzoyl perreas which can be used in combination with or used in combination with the compound of the general formula (I), it is more preferable to use them in combination with or in combination with the benzoyl pereas listed in the above (E).
  • Nzoyl 1 N, 1 [3,5-dichloro 1-41 (3-chloro 1-5-trifluoromethyl-2-pyridyloxy) phenyl] ⁇ Rarely mixed and used most preferably.
  • the dose of the compound of the general formula (I) varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually from 0.01 mg to 100 g, preferably from 0. 1 mg to 1 kg body weight of the host animal. It is appropriate to administer at a rate of lmg to 10g. Administration to the host is performed orally or parenterally.
  • the oral administration method include a method in which the compound of the general formula (I) is mixed with the host animal and administered together with the feed, or a tablet, solution, capsule containing the compound of the general formula (I) , Wafers, biscuits, minced meat and the like.
  • a compound of the formula (I) may be formulated into an appropriate formulation, and then administered intravenously, intramuscularly, intradermally, subcutaneously, or treated with spot-on.
  • Examples thereof include a method in which the compound is taken into the body by treatment or the like, and a method in which a resin piece containing the compound of the general formula (I) is implanted under the host animal.
  • composition for controlling ectoparasites in animals according to the present invention will be exemplified below, but the present invention is not limited thereto.
  • composition for controlling ectoparasites in animals comprising a pyridine compound or a salt thereof as an active ingredient.
  • R 1 and R 2 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, A cycloalkyl group, -C (W R 3 groups, -S (0) n R 5 groups, 1 NHR 6 groups,
  • One C (R 8 ) ⁇ ⁇ —R 9 group, or R 1 and R 2 together form C (R 1 Q ) R 11 group, or a nitrogen atom or oxygen together with an adjacent nitrogen atom may form a 5-membered or 6-membered heterocyclic group may 4-5 carbon atoms include atoms, R 3,
  • R 5 , R 6 , Z, R 7 , R 8 , R 9 , R 10 , 11 , W 1 and n are as described above).
  • X is an oxygen atom or a sulfur atom
  • X is an oxygen atom or a sulfur atom
  • R 1 is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, or an optionally substituted A cycloalkyl group, an aryl group which may be substituted, or -C (wherein R 3 is a R 3 group, and R 3 , R 4 and W 1 are as described above).
  • R 1 is a hydrogen atom
  • R 2 is a —C (R 8 ) 2 NO—R 9 group
  • R 8 and R 9 are as described above. object.
  • R 1 and R 2 are linked to form a 2 C (R 10 ) 1 N (R 12 ) R 13 group, R ) 0 is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted heterocyclic group, and R 12 and R 13 are as defined above (2)
  • R 1 is a hydrogen atom
  • X is an oxygen atom
  • R 1 and R 2 are each independently a hydrogen atom, alkyl group, alkoxyalkyl group, alkylaminoalkyl group, C 2 _ 6 cyclic Aminoa alkyl group, hydroxyalkyl group, Shianoarukiru group A thiocarbamoylalkyl group, an alkylcarbonyloxyalkyl group, an alkylcarbonyl group, an arylcarbonyl group, a trifluoromethyl-substituted arylcarbonyl group, an alkoxythiocarbonyl group or an alkoxycarbonyl group, or R 1 And R 2 together form a 2 C (R 1 "! ⁇ 1 group, and R 1G and R 11 are an alkoxy group and an alkylthio group, respectively.
  • the compound represented by the general formula (I) is N-cyanomethyl-41-trifluoromethyl-13-pyridinecarboxamide (Compound No. 1), N-ethyl-41-trifluoromethyl-13-pyridinepyridine (Compound No.
  • the compound represented by the general formula (I) is ⁇ -cyanomethyl-4-1-trifluoromethyl-13-pyridine lipoxamide, ⁇ -ethyl-14-trifluoromethyl-3-pyridincarboxamide, 4-trifluoro Oromethyl-1-pyridinecarboxamide
  • composition for controlling ectoparasites according to the above (1) which is at least one selected from the group consisting of 1-oxide and 4-trifluoromethyl-3-pyridinepyruboxamide.
  • the heterocyclic group moiety is selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the heterocyclic group moiety is selected from a nitrogen atom, an oxygen atom and a sulfur atom.
  • R 16 is an alkyl group.
  • (23) A composition for controlling ectoparasites in animals, comprising a compound of the formula (I) and another animal drug as active ingredients.
  • Other animal drugs include (A) phosphate or phosphate ester, (B) carbamate compounds, (C) pyrethroids, (D) amidines, (E) benzoylureas, (F) Neonicotinoids (G) The composition for controlling ectoparasites of animals according to (23), which is at least one animal drug selected from the group consisting of arylpyrazoles.
  • Benzoylpereas are N- (2,6-difluorobenzoyl) -1-N, 1- [3,5-dichloro-14- (3_chloro-5-trifluoromethyl-2-pyridyloxy) phenyl ] ⁇ Rare, 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea, 1- [2,5-dichloro-1- 4- (1,1,2,3) , 3,3-hexafluoropropoxy) phenyl] —3— (2,6-difluorobenzoyl) ⁇ rea, 1 _ (2-chlorobenzoyl) 1-3— (4-trifluoromethoxyphenyl) ⁇ rea, 1 [ ⁇ - (4-chloro-1-cyclopropylbenzylideneaminooxy) 1 ⁇ -tolyl] 1 3- (2,6-difluorobenzoyl) ⁇ rea, 1-[4-( 2-Ch
  • Benzoylpereas are ⁇ — (2,6-difluorobenzoyl) — ⁇ , 1- [3,5-dichloro-4 _ (3 chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] (4)
  • composition according to (1) or (23) acts on ectoparasites of animals.
  • the ticks are the ticks of the tick, the tick, the tick, The method according to the above (35), which is Ivan ticks, Tick ticks, Ixodid ticks, Schulce ticks, or Tick ticks.
  • Pets are dogs, cats, mice, rats, hamsters, guinea pigs, squirrels
  • test conjugate (Compound No. 1 or Compound No. 4) 1 OragZkg was filled into a gelatin capsule and administered once by oral gavage with about 10 ml of water. The dose was calculated from the body weight immediately before administration.
  • the dogs were bred in cages, fed tap water freely, and fed a predetermined amount of dog feed (DEQ, Oriental Yeast Co., Ltd.) once a day.
  • the cat flea non-blood-sucking adults within 3 days after emergence are released on the back coat of dogs (beagle male, 8 months old, weighing 9.0 kg) and parasitized.
  • Four days after the first parasitism of the first fleas collect the fleas using a flea comb and check the number of fleas colonized. Flea infestation is performed twice at weekly intervals.
  • test compound compound No. 1 or compound No. 4
  • Areas prepared in amorphous form are each filled into gelatin capsules by 15 mgZkg, and about 10 ml of water With a single oral gavage.
  • the dose can be calculated from the body weight immediately before administration. Dogs are kept in cages, fed with tap water freely, and given a predetermined amount of dog feed (DEQU, Oriental Yeast Co., Ltd.) once a day.
  • Four days after the second artificial flea parasitism fleas were collected using a flea comb, and the number of fleas settled was checked. Is obtained.
  • test compound compound ⁇ ⁇ 1 or compound No. 4 O mg / kg is orally administered to investigate the status of mite colonization and blood sucking. After that, the condition of molting, spawning and hatching will be investigated. It can be seen that each of the survey items has an excellent acaricidal effect as compared to the non-administered group.
  • Test compound (Compound No. 1 or Compound No. 4) and N— (2,6-difluorobenzoyl) -N, 1- [3,5-dichloro-4-1 (3-chloro-5-trifluoromethyl-2-) Pyridyloxy) phenyl] urea was formulated as amorphous Each of them is orally administered at a dose of 3 O mg / kg, and the status of mite colonization and blood sucking are investigated. After that, the condition of molting, spawning and hatching will be investigated. It can be seen that each of the survey items has an excellent acaricidal effect compared to the non-medicated group. Industrial applicability
  • a specific pyridine compound can be provided as an animal ectoparasite control agent.

Abstract

L'invention porte sur des compositions combattant les ectoparasites des animaux contenant comme principe actif des composés de pyridine de formule générale (I) ou leurs sels. Dans la formule (I): Y est haloalkyle; m est 0 ou 1; et Q est un groupe de formule générale (II) ou un groupe hétérocyclique facultativement substitué.
PCT/JP2001/004330 2000-05-25 2001-05-23 Compositions combattant les ectoparasites des animaux WO2001090075A1 (fr)

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Cited By (2)

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WO2003097604A1 (fr) * 2002-05-16 2003-11-27 Bayer Cropscience Gmbh Derives de pyridine carboxamide et leur utilisation en tant que pesticides
WO2004032629A1 (fr) * 2002-10-11 2004-04-22 Meiji Seika Kaisha, Ltd. Compositions melangees de lutte contre les insectes parasites

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JPH11180957A (ja) * 1997-12-24 1999-07-06 Sumitomo Chem Co Ltd アミジン誘導体、その製造法及びそれを有効成分とする有害動物防除剤

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Publication number Priority date Publication date Assignee Title
EP0580374A1 (fr) * 1992-07-23 1994-01-26 Ishihara Sangyo Kaisha, Ltd. Amides de pyridines et leurs sels, procédé pour leur préparation et des compositions les contenant
JPH0710841A (ja) * 1993-06-21 1995-01-13 Ishihara Sangyo Kaisha Ltd ４−トリフルオロメチルピリジン−３−カルボキサミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤
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JPH11180957A (ja) * 1997-12-24 1999-07-06 Sumitomo Chem Co Ltd アミジン誘導体、その製造法及びそれを有効成分とする有害動物防除剤

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WO2003097604A1 (fr) * 2002-05-16 2003-11-27 Bayer Cropscience Gmbh Derives de pyridine carboxamide et leur utilisation en tant que pesticides
JP2005537230A (ja) * 2002-05-16 2005-12-08 バイエル クロップサイエンス ゲーエムベーハー ピリジンカルボキサミド誘導体および農薬としてのその使用
CN100378076C (zh) * 2002-05-16 2008-04-02 拜尔作物科学有限公司 吡啶甲酰胺衍生物及其作为杀虫剂的用途
WO2004032629A1 (fr) * 2002-10-11 2004-04-22 Meiji Seika Kaisha, Ltd. Compositions melangees de lutte contre les insectes parasites

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