WO1997046101A1 - Agents de lutte contre les parasites a base de polysiloxanes cycliques - Google Patents

Agents de lutte contre les parasites a base de polysiloxanes cycliques Download PDF

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Publication number
WO1997046101A1
WO1997046101A1 PCT/EP1997/002622 EP9702622W WO9746101A1 WO 1997046101 A1 WO1997046101 A1 WO 1997046101A1 EP 9702622 W EP9702622 W EP 9702622W WO 9746101 A1 WO9746101 A1 WO 9746101A1
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WO
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Prior art keywords
spp
alkyl
methyl
stands
halogen
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PCT/EP1997/002622
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German (de)
English (en)
Inventor
Jochen Kalbe
Andreas Turberg
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU30914/97A priority Critical patent/AU3091497A/en
Publication of WO1997046101A1 publication Critical patent/WO1997046101A1/fr

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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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

  • the present invention relates to pesticides based on cyclic polysiloxanes mixed with arthropodicidal active ingredients
  • Cyclic polysiloxanes with 4 and 5 siloxane units of insecticide were known to be effective. It was also known that polysiloxanes can be used to spray insects by spraying (US Pat. No. 4,654,328). However, these active compounds do not show any lasting action
  • the invention therefore relates to the following mixtures and agents
  • R for identical or different radicals of the group methyl, ethyl,
  • n stands for integers from 3 to 6
  • R for identical or different radicals of the group methyl, ethyl,
  • n stands for integers from 3 to 6
  • Preferred arthropodicidal agents for the agents according to the invention are preferred.
  • insects especially parasiticides for use on animals.
  • the insecticides include agonists or antagonists of the nicotinergic acetylcholine receptors of insects, ivermectins and avermectins as well as phosphorus-containing compounds such as phosphoric or phosphonic acid esters, natural and synthetic pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic
  • the agonists or antagonists of the nicotinergic acetylcholine receptors of insects include the compounds known from the following publications:
  • R represents hydrogen, optionally substituted radicals from the group acyl, al yl, aryl, aralkyl, heteroaryl or heteroarylalkyl;
  • E represents an electron withdrawing group
  • Atom can be linked to the radical Z;
  • Z for a monofunctional group from the series alkyl, -OR, -SR, RN stands for a bifunctional group that is associated with the
  • Radical A or the radical X is linked
  • R represents hydrogen and also optionally substituted radicals from the
  • alkyl which may be mentioned are C 1 -C 4 -alkyl, in particular C 4 -C 4 alkyl
  • Phenyl, naphthyl, in particular phenyl, may be mentioned as aryl
  • Phenylmethyl and phenethyl may be mentioned as aralkyl
  • heteroaryl alkyl examples include heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, in particular N, as heteroatoms
  • Optionally substituted alkylene with 1-4, in particular 1-2, carbon atoms may be mentioned, the substituents listed above being the substituents and the alkylene groups being heteroatoms from the series N, O, S can be interrupted
  • a and Z together with the atoms to which they are attached, form a saturated or unsaturated heterocyclic ring.
  • the heterocyclic ring may contain a further 1 or 2 identical or different hetero atoms and / or hetero groups.
  • Oxygen is preferably a hetero atom , Sulfur or nitrogen and, as hetero groups, N-alkyl, alkyl of the N-alkyl group preferably containing 1 to 4, in particular 1 or 2, carbon atoms.
  • the heterocych ring contains 5 to 7, preferably 5 or 6 ring members
  • Examples of the heterocyclic ring are pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-l, 3,5-triazione, morpholine, which may optionally be substituted by methyl
  • E stands for an electron-withdrawing radical, in particular NO 2 , CN, haloalkylcarbonyl such as 1,5-halogeno-carbonyl, in particular COCF
  • Z stands for optionally substituted radicals alkyl, -OR, -SR, -NRR, where
  • R and the substituents preferably have the meaning given above
  • the heterocychic ring can contain a further 1 or 2 identical or different heteroatoms and / or hetero groups.
  • the hetero atoms are preferably oxygen, sulfur or nitrogen and as
  • the alkyls are methyl, ethyl, n- and l-propyl and n-, I- and t-butyl
  • the heterocych ring contains 5 to 7, preferably 5 or 6 ring members
  • heterocyclic ring examples include pyrrolidine, piperidine,
  • n 1 or 2
  • the phosphoric or phosphoric acid esters include:
  • the carbamates include
  • R 1 and R 2 represent halogen, optionally halogen-substituted alkyl, optionally halogen-substituted phenyl,
  • R ' represents hydrogen or CN
  • R represents hydrogen or halogen
  • R 1 represents hydrogen or halogen
  • R 2 for halogen in particular fluorine, chlorine, bromine, t ⁇ halomethyl
  • R ⁇ represents hydrogen or CN
  • R 4 represents hydrogen or fluorine
  • R "1 represents hydrogen
  • R 1 represents chlorine
  • R 2 represents chlorine, trifluoromethyl, p-chlorophenyl
  • R * stands for CN
  • R 4 represents hydrogen or fluorine
  • R- stands for hydrogen
  • R 1 represents chlorine
  • R 2 represents chlorine or p-chlorophenyl
  • R 4 represents fluorine in the 4-position
  • R 5 represents hydrogen
  • amidines include:
  • Juvenile hormones or juvenile hormone-like substances include substituted diaryl ethers, benzoyl ureas and triazine derivatives. Juvenile hormones and juvenile hormone-like substances include in particular compounds of the following formulas:
  • the substituted diaryl ethers include, in particular, substituted alkoxydiphenyl ethers or diphenyl methanes of the general formula VI
  • R 1 represents hydrogen, halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, dioxyalkylene, dioxyhalogenalkylene, CN, NO 2 , alkenyl, alkynyl, alkoxyalkyl, alkoxyalkoxy, hydroxyalkoxy,
  • R 2 represents the radicals specified for R 1 ,
  • R 3 represents the radicals specified for R 1 ,
  • R 4 represents hydrogen, alkyl, haloalkyl or halogen
  • R -1 represents the radicals specified for R 4 .
  • Het stands for optionally substituted heteroaryl, which does not have the
  • Hetero atom is bound to the rest of the rest
  • X, Y independently of one another represent -O-, -S-
  • Z represents -O-, -S-, -CH 2 -, -CHCH 3 -, -C (CH 3 ) 2 -,
  • n and n independently of one another represent 0, 1, 2, 3 but their sum is equal to or greater than 2.
  • R 1 is hydrogen, methyl, trifluoromethyl, methoxy, trifluoromethoxy, chlorine, fluorine R ⁇ stands for hydrogen
  • R 1 represents hydrogen, fluorine, chlorine, methyl
  • R 4 represents hydrogen or methyl
  • R 5 represents methyl, ethyl, trifluoromethyl or hydrogen
  • Het is pyridyl or pyridazinyl which are optionally substituted by
  • Z represents O, CH 2 or -C (CH 3 ) 2 -
  • n 1,
  • n 1
  • Benzoylureas include compounds of the formula VII
  • R represents halogen
  • R 1 represents hydrogen or halogen
  • R 3 represents hydrogen, halogen or C 1 -C 4 -alkyl
  • the triazines include compounds of the formula (VIII)
  • R represents cyclopropyl or isopropyl
  • R- hydrogen, halogen, C ] -C 12 alkylcarbonyl ; Cyclopropylcarbonyl, C, -C p - alkyl carbamoyl, C, -C p alkylthiocarbamoyl or C 2 -C 6 alkenyl carbamoyl means, and
  • R 3 for hydrogen, C r C 12 alkyl, cyclopropyl, C 2 -C 6 alkenyl, C, -C ] 2 alkylcarbonyl, cyclopropylcarbonyl, C j -Cp alkylcarbamoyl, C r C p alkylthio carbamoyl or C 2 -C -alkenylcarbamoyl and their acid addition salts, which are non-toxic to warm-blooded animals.
  • arthropodicidal active ingredients with the comnon names Propoxur, Cyfluth ⁇ n, Flumeth ⁇ n, Py ⁇ proxyfen, Methoprene, Diazinon, Amitraz, Fenthion, Imidaclop ⁇ d, Ti 435, AKD 1022, Ti 304, T ⁇ flumuron, Ivermectin, Avermectin
  • the active substances are present in the compositions in m concentrations of 0.1 to 20% by weight, preferably between 1 to 10% by weight.
  • the agents according to the invention have considerable practical advantages. Their action on pests is immediate, that is, the consumer sees them
  • control measure is carried out directly
  • compositions according to the invention are suitable for controlling animal pests, preferably arthropods, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are resistant to normally sensitive and resistant species and to all or some of them Developmental stages effective
  • animal pests preferably arthropods, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are resistant to normally sensitive and resistant species and to all or some of them Developmental stages effective
  • the pests mentioned above include arthropods, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are resistant to normally sensitive and resistant species and to all or some of them Developmental stages effective
  • the pests mentioned above include
  • Isopoda for example Oniscus asellus, Armadillidium vulgare,
  • Diplopoda e.g. Blaniulus guttulatus From the order of the Chilopoda eg Geophilus carpophagus, Scutigera spec
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp,
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lamgerum, Hyalopterus arundinis,
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp, Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp, Sitophilus spp, Otiorrhynchus Sulcatushidpphidpphidispphppisidpphidisidpphidispphidispphidispphcpphc, spp spp, Lyctus spp., Meligethes aeneus, Ptinus spp,
  • Niptus hololeucus Gibbium psylloides, Tribolium spp, Tenebno mohtor, Agriotes spp, Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica
  • Hymenoptera e.g. Diprion spp, Hoplocampa spp, Lasius spp, Monomorium pharaonis, Vespa spp
  • Dacus oleae Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopis
  • Ceratophyllus spp From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans From the order of the Aca ⁇ na z B Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllivoraopilil, Phyllivoraopil
  • the agents are suitable for controlling animal pests, such as arthropods, preferably insects, arachnids, which occur in livestock farming and animal breeding in farm animals, breeding, zoo, laboratory, experimental and hobby animals. They are against all or individual stages of development of the pests and against resistant and normally sensitive types of
  • the pests include:
  • Eomenacanthus spp. Menacanthus spp., Trichodectes spp., Felicola spp.,
  • Hydrotaea spp. Muscina spp., Haematobosca spp., Haematobia spp., Stomoxys spp., Fannia spp., Glossina spp., Lucilia spp., Calliphora spp., Auchmeromyia spp.,
  • Oestrus spp. Rhinoestrus spp., Melophagus spp., Hippobosca spp.
  • Siphonaptera e.g. Ctenocephalides spp., Echidnophaga spp., Ceratophyllus spp.
  • Domestic and farm animals include mammals such as cattle, sheep, goats, "horses, pigs, dogs, cats, camels, water buffalo, donkeys, rabbits, Fallow deer, reindeer, fur animals such as mink, chinchilla, raccoon, birds such as chickens, turkeys, pheasants, geese, ducks.
  • Laboratory and experimental animals include e.g. Mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • Hobby animals include e.g. Dogs and cats.
  • the agents according to the invention can also be used in closed rooms such as apartments, halls or the like. deploy. They are particularly suitable for controlling animal pests and nuisances that occur in the household.
  • agents according to the invention are used directly or in the form of suitable preparations dermally or by treating their environment.
  • the dermal application happens e.g. in the form of bathing, diving (dipping), spraying (spraying), pouring on (pour-on or spot-on), washing, shampooing, watering, powdering.
  • Suitable preparations are:
  • Emulsions and suspensions for dermal use and semi-solid preparations are Emulsions and suspensions for dermal use and semi-solid preparations
  • Solid preparations such as powder or dusts, also through microencapsulation of the liquid ingredients. In addition to use on animals, these preparations can also be used in the home, in hygiene or in agriculture
  • Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on, sprayed on or applied by dipping (dipping), bathing or washing
  • the solutions are prepared by dissolving the active ingredients in the cyclic silicones and / or suitable solvents and possibly adding additives such as solubilizers, acids, bases, buffer salts, antioxidants and preservatives
  • Alcohols such as ethanol, butanol, benzyl alcohol, glycols, hydrocarbons, propylene glycol, polyethylene glycols, N-methyl-pyrrohdon, and mixtures thereof
  • the active ingredients can optionally also be dissolved in physiologically acceptable vegetable or synthetic oils
  • Solvents which may be mentioned are solvents which require the active ingredient to be dissolved in the main solvent or prevent it from precipitating out. Examples are polyvinylpyrrohdon, polyoxyethylated castor oil, polyoxyethylated sorbitan esters
  • Preservatives are benzyl alcohol, chlorobutanol, p-hydroxybenzoic acid ester, n-butanol
  • Thickeners are inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers.
  • Gels that are applied or spread on the skin are produced by adding enough thickening agent to solutions that have been prepared as described above to produce a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners
  • pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredients being distributed over the surface of the body
  • Pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredients in suitable solvents or solvent mixtures that are compatible with the skin.
  • Solvents which may be mentioned are water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol and glycol monoethyl ether , Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2-dimethyl-4-oxy-methylene-1, 3-d ⁇ oxolan
  • Dyes are all dyes approved for use on animals, which can be dissolved or suspended
  • Excipients are also spreading oils such as isopropyl mypstat, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherol
  • Light stabilizers are, for example, substances from the class of the benzophenones or
  • Novantisol acidic Adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Emulsions are either water in oil or oil in water.
  • Emulsifiers and optionally other auxiliaries such as dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances, homogenized with the solvent of the other phase
  • hydrophobic phase paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C 16 -C 18 , isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohol the chain length Cp-C ) 8 , isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as dibutyl phthalate, diisopropyl adipate, the latter related ester mixtures including fatty alcohols such as isotridecyl alcohol alcohol, 2-octyl alcohol alcohol, 2-octyl alcohol alcohol
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase water, alcohols, e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • nonionic surfactants for example polyoxyethylated ⁇ castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, Pol yoxy ethyl stearate, alkylphenol; ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin,
  • anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt, cationic surfactants such as cetyl methyl methyl ammonium chloride
  • auxiliaries which may be mentioned are substances which increase viscosity and stabilize the emulsion, such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrodone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, silica glycols, waxes, polyethylene glycols, waxes, polyethylene glycols, waxes, polyethylene glycols, waxes, polyethylene glycols, waxes, and ethylene glycols or mixtures of the listed substances
  • Suspensions are produced by suspending the active ingredients in a carrier liquid, optionally with the addition of further auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers
  • surfactants specified above may be mentioned as wetting agents (dispersants)
  • the active ingredients are mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape
  • suitable carriers if appropriate with the addition of auxiliaries
  • All physiologically compatible solid inert substances may be mentioned as carrier substances. All such serve inorganic and organic substances.
  • Inorganic substances are, for example, table salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above
  • auxiliaries are lubricants and lubricants such as magnesium stearate, stearic acid, talc, bentonite
  • Ready-to-use preparations contain the active ingredients in concentrations of
  • Preparations which are diluted before use contain the active compounds in concentrations of 0.5 to 90 percent by weight, preferably from 1 to 50 percent by weight
  • Agents according to the invention in which the arthropodicidal active ingredient is present in solution in the cyclic polysiloxane are particularly preferred

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des agents de lutte contre les parasites à base de polysiloxanes cycliques et de principes actifs arthropodicides.
PCT/EP1997/002622 1996-06-03 1997-05-22 Agents de lutte contre les parasites a base de polysiloxanes cycliques WO1997046101A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30914/97A AU3091497A (en) 1996-06-03 1997-05-22 Pesticides based on cyclic polysiloxanes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19622190.0 1996-06-03
DE1996122190 DE19622190A1 (de) 1996-06-03 1996-06-03 Schädlingsbekämpfungsmittel auf Basis cyclischer Polysiloxane

Publications (1)

Publication Number Publication Date
WO1997046101A1 true WO1997046101A1 (fr) 1997-12-11

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PCT/EP1997/002622 WO1997046101A1 (fr) 1996-06-03 1997-05-22 Agents de lutte contre les parasites a base de polysiloxanes cycliques

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DE (1) DE19622190A1 (fr)
WO (1) WO1997046101A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1393056B1 (it) * 2008-09-22 2012-04-11 Bio Lo Ga Srl Uso di vitamina e o suoi derivati per il controllo di artropodi

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2829388A1 (de) * 1977-07-27 1979-02-01 Dow Corning Emulsion auf basis eines siloxan- oxalkylen-copolymers und eines organischen oberflaechenaktiven mittels
EP0191543A1 (fr) * 1985-01-15 1986-08-20 Ventec Laboratories, Inc. Toxiques de silicone contre les insectes
US4654328A (en) * 1984-11-13 1987-03-31 Shin-Etsu Chemical Co., Ltd. Method for controlling sanitary and agricultural pests
EP0249409A2 (fr) * 1986-06-07 1987-12-16 Coopers Animal Health Limited Formulations liquides
JPS63316706A (ja) * 1987-06-19 1988-12-26 Osaka Seiyaku:Kk 常温揮散性液剤
JPH07206615A (ja) * 1993-11-25 1995-08-08 Dainippon Jochugiku Co Ltd 防虫剤組成物
EP0682869A1 (fr) * 1994-05-20 1995-11-22 Bayer Ag Lutte non-systhémique contre les parasites

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2829388A1 (de) * 1977-07-27 1979-02-01 Dow Corning Emulsion auf basis eines siloxan- oxalkylen-copolymers und eines organischen oberflaechenaktiven mittels
US4654328A (en) * 1984-11-13 1987-03-31 Shin-Etsu Chemical Co., Ltd. Method for controlling sanitary and agricultural pests
EP0191543A1 (fr) * 1985-01-15 1986-08-20 Ventec Laboratories, Inc. Toxiques de silicone contre les insectes
EP0249409A2 (fr) * 1986-06-07 1987-12-16 Coopers Animal Health Limited Formulations liquides
JPS63316706A (ja) * 1987-06-19 1988-12-26 Osaka Seiyaku:Kk 常温揮散性液剤
JPH07206615A (ja) * 1993-11-25 1995-08-08 Dainippon Jochugiku Co Ltd 防虫剤組成物
EP0682869A1 (fr) * 1994-05-20 1995-11-22 Bayer Ag Lutte non-systhémique contre les parasites

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Week 8906, 5 April 1989 Derwent World Patents Index; AN 89-043652, XP002040701 *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Week 9544, 15 December 1995 Derwent World Patents Index; AN 95-339186, XP002040702 *

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DE19622190A1 (de) 1997-12-04
AU3091497A (en) 1998-01-05

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