EP1496744A1 - Bekämpfung von parasiten bei tieren - Google Patents

Bekämpfung von parasiten bei tieren

Info

Publication number
EP1496744A1
EP1496744A1 EP03746283A EP03746283A EP1496744A1 EP 1496744 A1 EP1496744 A1 EP 1496744A1 EP 03746283 A EP03746283 A EP 03746283A EP 03746283 A EP03746283 A EP 03746283A EP 1496744 A1 EP1496744 A1 EP 1496744A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
optionally substituted
alkoxy
spp
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP03746283A
Other languages
German (de)
English (en)
French (fr)
Inventor
Andreas Turberg
Olaf Hansen
Venkata-Rangarao Kanikanti
Reinhold LÖHR
Dirk Mertin
Kirkor Sirinyan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer Healthcare AG
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 Healthcare AG filed Critical Bayer Healthcare AG
Publication of EP1496744A1 publication Critical patent/EP1496744A1/de
Withdrawn legal-status Critical Current

Links

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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N47/06—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 containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole

Definitions

  • the present invention relates to the systemic and non-systemic control of parasites in animals using phenylketoenol derivatives.
  • Phenylketoenols are known compounds. It is also known that these keto-enols have excellent ' insecticidal, acaricidal, herbicidal and fungicidal activity (EP-A-0528156, WO 98/05638 and WO 97/01535). *
  • these compounds are not necessarily suitable as arthopodicidal agents in the veterinary field.
  • biological effects against relevant ectoparasites and hygiene pests were surprisingly found in combination with certain dosage forms.
  • the compounds described are particularly suitable for use against single-host tick species, lice and
  • Mites on farm animals to control stable flies e.g. in the feed-through process and for combating flea, mite and tick populations in pet farming. Resistant species are also recorded.
  • X represents alkyl, halogen, alkoxy or haloalkyl
  • Y represents hydrogen, alkyl, halogen, alkoxy, haloalkyl
  • Z represents alkyl, halogen alkoxy
  • n represents a number from 0 to 3, or the radicals X and Z together with the phenyl radical to which they are attached, the naphthalene radical of the formula
  • a and B can be the same or different and are hydrogen, optionally substituted by halogen substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, optionally cycloalkyl interrupted by heteroatoms or optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, Aralkyl or hetaryl,
  • a and B together with the carbon atom to which they are attached form a saturated or unsaturated, optionally interrupted by heteroatoms and optionally substituted cycle,
  • D represents oxygen, sulfur or -NH-
  • E + represents a metal ion equivalent or an ammonium ion
  • L and M represent oxygen and / or sulfur
  • Rl for optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl.
  • R ⁇ represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or phenyl or benzyl which is optionally substituted by halogen,
  • R3, R4 and R ⁇ independently of one another for optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino.
  • R6 and R ⁇ independently of one another represent hydrogen, optionally alkyl substituted by halogen, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl,
  • R ⁇ and R ⁇ together represent an alkylene radical which may be interrupted by oxygen
  • A, B, D, E, L, M, X, Y, Z n , R 1 , R 2 , R 3 , R 4 , R 5 5 R 6 and R 7 have the meanings given above.
  • Y represents hydrogen, C ⁇ -Cg-alkyl, halogen, C ⁇ -Cg-alkoxy, C1-C3 -haloalkyl,
  • Z represents C 1 -Cg alkyl, halogen, C -Cg alkoxy,
  • n stands for a number from 0 to 3
  • a and B are identical or different and are hydrogen or straight-chain or branched C 1 -C 12 -alkyl which is optionally substituted by halogen, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, Ci-Cg-polyalkoxy-C2-Cg-alkyl, -C-C ⁇ o-alkylthio-C2-Cg-alkyl, cycloalkyl with 3 to 8
  • Ring atoms which can be interrupted by oxygen and / or sulfur or optionally aryl, hetaryl substituted by halogen, Ci-Cg-alkyl, C] -Cg-haloalkyl, C ⁇ -Cg-alkoxy, Ci-Cg-haloalkoxy, nitro or aryl-Ci-Cg-alkyl,
  • E + represents a metal ion equivalent or an ammonium ion
  • L and M represent oxygen and / or sulfur
  • R 1 for C1-C20-alkyl which is optionally substituted by halogen, C 2 -C20-alkenyl, kyl, -C-C8-polyalkoxy-C2-Cg-alkyl or cycloalkyl with 3 to 8 ring atoms, which can be interrupted by oxygen and / or sulfur atoms,
  • R 2 for C1-C20-alkyl which is optionally substituted by halogen, C1-C20-alkenyl, -C -C-alkoxy ⁇ C2-Cg-alkyl, Ci-Cg-polyalkoxy-
  • Ci-Cg-alkyl represents phenyl or benzyl optionally substituted by halogen, nitro, Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkyl,
  • R 3 , R 4 and R ⁇ independently of one another for Ci-Cg-alkyl optionally substituted by halogen, Ci-Cg-alkoxy, Ci-Cg-alkylamino, di- (C ⁇ -Cg -) - alkylamino, Ci-Cg- Alkylthio, C2-C5-alkenylthio, C2-C5-alkynylthio, C3-C7-cycloalkylthio, for optionally by halogen, nitro, cyano, -C-C4-alkoxy, -C-C4-haloalkoxy, C ⁇ ⁇ C4-alkylthio, C ⁇ -C4 -Halogenal- alkylthio, C1-C4- alkyl, -CC-C4-haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R6 and R 7 independently of one another for hydrogen, optionally substituted by halogen C1-C20-alkyl, C1-C20-alkoxy, C2-Cg-alkenyl, -C-C20-alkoxy-C ⁇ -C20-alkyl, for optionally by halogen, C ⁇ -C20 haloalkyl, -C-C20 ⁇ alkyl or C1-C20-alkoxy substituted phenyl for benzyl optionally substituted by halogen, C1-C20-alkyl, -C-C20-haloalkyl or -C-C20-alkoxy or together for an optionally interrupted by oxygen C2-Cg -Alkylene ring stand,
  • X represents C 1 -Cg-alkyl, halogen, C ⁇ -Cg-alkoxy or C ⁇ -C2-haloalkyl
  • Y represents hydrogen, Ci-Cg-alkyl, halogen, Ci-Cg-alkoxy, C ⁇ -C2-haloalkyl,
  • Z represents C1-C4-alkyl, halogen, C 1 -C 4 -alkoxy,
  • n stands for a number from 0 to 3
  • a and B are the same or different and represent hydrogen, optionally by
  • a and B together with the carbon atom to which they are attached, a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally by halogen, -C -C-alkyl, Ci-Cs-alkoxy, C ⁇ -C3-haloalkyl, C 1 -C 4 haloalkoxy, C 3 -C 3 alkyl thio or aryl substituted aryl substituted by halogen, alkyl, alkoxy substituted 3- to 8-membered ring,
  • E + stands for a metal ion equivalent or an ammonium ion
  • L and M each represent oxygen and / or sulfur
  • phenyl-C-C4-alkyl optionally substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C-C3-haloalkyl, C-C3-haloalkoxy,
  • Ci-Cg-alkyl stands for optionally substituted by halogen and C1-C4-alkyl-substituted phenoxy -CC-C5-alkyl
  • R2 C2-Cg-alkyl is optionally substituted by halogen, C ⁇ -Cig alkyl, C 2- C lg-alkenyl, C2-C ⁇ g-alkoxy-C2-Cg-alkyl, Ci-Cg-polyalkoxy,
  • R 3 , R 4 and R ⁇ independently of one another for Ci-Cg-alkyl optionally substituted by halogen, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (C ⁇ -Cg -) - alkylamino, Ci - Cg-alkylthio, C3-C4-alkenylthio, C2-C4-alkynylthio, C3-Cg-cycloalkylthio, for optionally by fluorine, chlorine, bromine, nitro, cyano, C ⁇ -C3 alkoxy, C ⁇ -C3-haloalkoxy, C ⁇ -C3 -Alkylthio, -C-C3-haloalkylthio, -C-C3-alkyl, C1-C3 -haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R6 and R 7 independently of one another for hydrogen, optionally substituted by halogen-C20 "alkyl, C1-C20-alkoxy, C2-Cg-alkenyl, -CC-C20" alkoxy-C ⁇ -C20- a lkylj for optionally by halogen, C 1 -C 5 haloalkyl, C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted phenyl, which represents benzyl optionally substituted by halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy,
  • X represents methyl, ethyl, propyl, i-propyl, fluorine, chlorine, bromine, methoxy, ethoxy and trifluoromethyl
  • Y for hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, tert-butyl,
  • Z represents methyl, ethyl, i-propyl, butyl, i-butyl, tert-butyl, fluorine, chlorine, bromine, methoxy and ethoxy,
  • n stands for a number from 0 to 3
  • a and B are the same or different and are hydrogen, optionally substituted by halogen, straight-chain or branched C 1 -C 6 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 6 -alkoxy-C2-C4-alkyl, C ⁇ -C4-poly-alkoxy-C2-C4-alkyl, C ⁇ l -CG-alkylthio-C2-C4-alkyl, cycloalkyl having 3 to 6 ring atoms, which may be interrupted by 1 to 2 oxygen and / or sulfur atoms or optionally aryl, pyridine, imidazole, pyrazole, triazole, indole, thiazole or aryl C1- substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, nitro C3
  • a and B together with the carbon atom to which they are attached, a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally by fluorine, chlorine, C1-C4-alkyl, -C-C4-alkoxy, trifluoromethyl, C ⁇ - C -alkylthio or aryl which is optionally substituted by fluro, chlorine, methyl, methoxy form a substituted 3- to 8-membered ring,
  • E + represents a metal ion equivalent or an ammonium ion
  • L and M each represent oxygen and / or sulfur
  • R 1 for optionally substituted by fluorine or chlorine Cj-C 14 alkyl, Ci-C 14 alkyl, C2-C 14 alkenyl, -C -C4 alkoxy-C2-Cg-alkyl,
  • phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, nitro,
  • R 2 for optionally substituted by fluorine or chlorine Ci -C 14 alkyl, C2-Ci4-alkenyl, -C-C4-alkoxy-C2-Cg-alkyl, -C -C4-polyalkoxy-
  • R 3 , R 4 and R5 independently of one another for C1-C4-alkyl, C1-C4-alkoxy, C 1 -C 4 -alkylamino, di- optionally substituted by fluorine or chlorine
  • R6 and R 7 independently of one another, optionally substituted by fluorine, chlorine, bromine, Ci-CiQ-alkyl, Cj-C 10- alkoxy, -C-C ⁇ o-alkoxy- (Cl-C ⁇ o) alkyl, for optionally by fluorine, chlorine, bromine C 1 -C 20 haloalkyl, C 1 -C 20 alkyl or C 1 -C 4 alkoxy substituted phenyl, for benzyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 alkoxy,
  • dihydrofuranone derivatives ie compounds of the formula (I) in which D represents oxygen, are used.
  • the other substituents can assume the meanings given above.
  • pyrrolidinedione derivatives i.e. Compounds of formula (I) in which D is -NH- is used.
  • the other substituents can assume the meanings given above.
  • compounds of the type Ilc can be used as particularly preferred. mentioned, which are disclosed in WO98 / 05638, in particular Examples Ilc-1 to llc-21. Compounds of the type Ilc which are disclosed in WO97 / 01535, in particular the examples Ilcl to Ilc-9, may also be mentioned as particularly preferred.
  • the active substances mentioned are suitable for favorable warm-blood toxicity for the systematic and / or non-systemic control of parasites which occur in animal husbandry and animal breeding in domestic and farm animals as well as zoo, laboratory, experimental and hobby animals. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive types of pests.
  • Parasites are particularly arthropods.
  • the preparations according to the invention are preferably used to control ectoparasites.
  • the above-mentioned ectoparasites include: tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • These parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp.
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • Livestock and breeding animals include mammals such as Cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer;
  • Fur animals such as Mink, chinchilla, raccoon; such as. Chickens, geese, turkeys, ducks.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the pets include dogs and cats.
  • the application can be prophylactic as well as therapeutic.
  • the active substances for systemic control of parasites are preferably used directly or in the form of suitable preparations enterally, parenterally, dermally or nasally, in particular orally, transdermally, by means of pour-on formulations or as an injection.
  • the enteral application of the active ingredients happens, for. B. orally in the form of powder, tablets, capsules, pastes, drinkers, granules, orally administrable solutions, suspensions and emulsions, boluses, medicated feed or drinking water.
  • the dermal application happens for. B. in the form of diving (dipping), spraying (spraying) or pouring (pour-on or spot-on).
  • Parenteral use happens e.g. B. in
  • Injection solutions are prepared by dissolving the active ingredient in a suitable solvent and possibly additives such as solubilizers, acids,
  • Bases can be added.
  • the solutions are sterile filtered and filled.
  • solvents which may be mentioned are: physiologically compatible solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone and mixtures thereof.
  • the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • solubilizers solvents which require the active ingredient to be dissolved in the main solvent or prevent it from precipitating out.
  • solvents which require the active ingredient to be dissolved in the main solvent or prevent it from precipitating out.
  • examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • preservatives examples include: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.
  • suitable preparations for oral administration are: tablets, homogeneous solutions, emulsions, suspensions. Oral solutions are applied directly. Concentrates are used orally after previous dilution to the application concentration. Oral solutions and concentrates are prepared as described above for the injection solutions, whereby sterile work can be dispensed with.
  • Suitable preparations for transdermal application are known to be active substance-containing solutions which may contain substances which promote resorption.
  • Resorption-promoting substances are, for example, DMSO (dimethyl sulfoxide), DMF (dimethylformamide), triglycerides and long-chain aliphatic fatty acid esters, azones and their derivatives, terpenes and essential oils, amino acid derivatives.
  • Said preparations contain the active ingredient in concentrations of 0.1 to 65% by weight, preferably from 1.0 to 40% by weight.
  • the dermal application happens e.g. in the form of bathing, diving (dipping), spraying (spraying), pouring on (pour-on or spot-on), washing, shampooing,
  • Suitable preparations are:
  • Emulsions and suspensions for dermal use and solid or semi-solid preparations Formulations in which the active ingredient is processed in an ointment base or in an oil in water or water in oil emulsion base;
  • 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 ingredient in a suitable solvent and possibly adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • solvents water, alkanols, glycols, polyethylene glycols, propylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkyl glycol alkyl ethers such as dipropylene glycol monomethyl ether, butyl glycol ether, diethylene glycol Acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2-pyrrolidone, 2-dimethyl-4-oxy-methylene-l, 3-dioxolane, 2- (l-No - nyl) -l, 3-dioxolane, transcutol, solketal, propylene carbonate, propylene glycol dia
  • the active ingredients can optionally also be dissolved in physiologically compatible vegetable or synthetic oils.
  • solubilizers solvents, the solution of the active ingredient in
  • polyvinyl pyrrolidone polyoxyethylated castor oil
  • polyoxyethylated sorbitan esters examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol. It may be advantageous to add thickeners when preparing the solutions. Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and metacrylates.
  • 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 ingredient being distributed over the surface of the body. Pour-on formulations are also conceivable in which the active ingredient penetrates the skin and has a systemic effect.
  • pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, further auxiliaries such as dyes, antioxidants, light stabilizers and adhesives are added. In the case of pour-on formulations which act systemically, substances which promote resorption can advantageously also be added.
  • Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Auxiliaries are also spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid,
  • Light stabilizers are, for example, substances from the class of benzophenones or novantisolic acid.
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Reso ⁇ tionsfördemde substances are such.
  • Emulsions can be used orally, dermally or as injections. They are either of the water in oil type or the oil in water type.
  • hydrophobic phase paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid bigylceride, triglyceride mixture with vegetable fatty acids of chain length C 8 . 12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids which may also contain hydroxyl groups, mono- and diglycerides of C 8 / CIO fatty acids.
  • 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 6 -C 8 , isopropyl myristate, isopropyl palmitate, caprylic / capric alcohol ester of the saturated fatty length 12 -C ⁇ g,
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase The following can be mentioned as the hydrophilic phase:
  • Alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
  • mpholytic 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 monoetl anolamine salt; cationic surfactants such as cetyltrimethylammonium chloride.
  • auxiliaries 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, polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, Waxes, colloidal silica or mixtures of the listed substances.
  • Suspensions can be used orally, dermally or as an injection. They are produced by suspending the active ingredient in a carrier liquid, optionally with the addition of further auxiliaries such as wetting agents, dyes, substances which promote absorption, preservatives, antioxidants or light stabilizers. All homogeneous solvents and solvent mixtures may be mentioned as carrier liquids.
  • the surfactants specified above may be mentioned as wetting agents (dispersants).
  • Semi-solid preparations can be administered orally or dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.
  • the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic substances are e.g. 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 ingredient in concentrations of 1 pp - 80 percent by weight, preferably from 0.01 - 65 percent by weight.
  • Preferred amounts of active ingredient are 1 to 50 percent by weight, particularly preferably 5 to 40 percent by weight.
  • Preparations which are diluted before use contain the active ingredient in concentrations of 0.5-90 percent by weight, preferably from 1 to 50 percent by weight.
  • Solid preparations include powders, premixes and concentrates, granules, pellets, tablets, boluses, capsules, aerosols and inhalants and molded articles.
  • the parasite control according to the invention is carried out non-systemically by means of dermal application.
  • Shaped bodies include Collars, pendants for collars
  • solid formulations according to the invention which release amounts of active ingredient from 10 to about 300 mg, preferably 20 to 200 mg, particularly preferably 25 to 160 mg, per kg of body weight of the animal to be treated over the course of at least three weeks, to apply to achieve good effectiveness.
  • Polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters which are sufficiently compatible with the abovementioned active ingredient may be mentioned as such.
  • the polymers must have sufficient strength and flexibility so that they do not crack or become brittle during molding. They have to be of sufficient durability to be resistant to normal wear and tear his. In addition, the polymers must allow sufficient migration of the active ingredient to the surface of the molded body.
  • the polyvinyl resins include polyvinyl halides such as polyvinyl chloride, polyvinyl chloride-vinyl acetate and polyvinyl fluoride; Polyacrylate and polymethacrylate esters, such as
  • Polymethyl acrylate and polymethyl methacrylate Polymethyl acrylate and polymethyl methacrylate; and polyvinylbenzenes such as polystyrene and polyvinyltoluene. Special mention should be made of polyvinyl chloride.
  • plasticizers which are usually used to plasticize solid vinyl resins are suitable for the production of the molded bodies based on polyvinyl resin.
  • the plasticizer to be used depends on the resin and its compatibility with the plasticizer.
  • Suitable plasticizers are, for example, esters of phosphoric acid, such as esters of phthalic acid, such as dimethyl phthalate and diocytyl phthalate, and esters of adipic acid, such as diisobutyl adipate.
  • esters such as the esters of azelaic acid, maleic acid, ricinoleic acid, myristic acid, palmitic acid, oleic acid, sebacic acid, stearic acid and trimellitic acid, as well as complex linear polyesters, polymeric plasticizers and epoxidized soybean oils can also be used.
  • the amount of plasticizer is about 10 to 50%, preferably about 20 to 45% by weight of the total composition.
  • the moldings may contain further constituents, such as stabilizers, lubricants, fillers and coloring materials, without changing the basic properties of the composition.
  • Suitable stabilizing agents are antioxidants and agents which protect the tapes from ultraviolet radiation and unwanted degradation during processing, such as extrusion.
  • stearates, stearic acid and low molecular weight polyethylenes can be used as lubricants.
  • These ingredients can be used in a concentration up to about 5% by weight of the total composition.
  • the various constituents are mixed by known processes and compression-molded by known extrusion or injection molding processes.
  • the choice of the processing method for the production of the shaped body depends fundamentally on the rheological properties of the strip material and the shape of the desired strip.
  • the processing methods can be set according to the processing technology or the type of shaping. In process technology, the processes can be subdivided according to the rheological conditions they run through. Then come for viscous tape materials
  • the moldings according to the invention can be produced by casting, dipping, pressing, injection molding, extruding, calendering, embossing, bending, deep drawing etc.
  • the polyurethanes used as the carrier material are prepared in a manner known per se by reacting polyisocyanates with higher molecular weight compounds having at least two groups which are reactive toward isocyanates, and optionally with low molecular weight chain extenders and / or monofunctional chain terminators.
  • Polyisocyanates containing isocyanurate groups as described, for example, in US Pat. No. 3,001,973, in DE Patents 1,022,789, 1,222,067 and 1,027,394 and in DE-OSes 1,929,034 and 2,004,048; Polyisocyanates containing urethane groups, as described, for example, in DE-PS 752261 or in US Pat. No. 3,394,164; Polyisocyanates containing acylated urea groups according to DE-PS 1 230 778; Polyisocyanates having biuret groups, as described, for example, in DE-PS 1 101 394, in US Pat. Nos.
  • distillation residues obtained in the industrial production of isocyanates and having isocyanate groups, optionally dissolved in one or more of the aforementioned polyisocyanates It is also possible to use any mixtures of the aforementioned polyisocyanates.
  • Preferred polyisocyanates are generally the tolylene diisocyanates and the diphenylmethane diisocyanates.
  • Addition products of alkylene oxides with phenol-formaldehyde resins or with urea-formaldehyde resins can also be used according to the invention.
  • the finished polyurethane should not be swellable in water.
  • the use of an excess of polyhydroxyl compounds with ethylene oxide units should therefore be avoided.
  • Thermoplastic materials are particularly emphasized for the production of the molded bodies
  • Elastomers These are materials that contain elastomeric phases in thermoplastically processable polymers either physically mixed in or chemically bound. A distinction is made between polymer blends in which the elastomeric phases are part of the polymeric structure. Due to the structure of the thermoplastic elastomers, hard and soft areas are side by side. The hard areas form a crystalline network structure or a continuous phase whose spaces are filled with elastomeric segments. Because of this structure, these materials have rubber-like properties.
  • thermoplastic elastomers There are 5 main groups of thermoplastic elastomers:
  • TPU Thermoplastic Polyurethanes
  • TPO Thermoplastic Polyolefins
  • Suitable copolyesters are composed, for example, of a large number of recurring, short-chain ester units and long-chain ester units which are combined by ester linkages, the short-chain ester units making up about 15-65% by weight of the copolyester and having the formula (II) ,
  • R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350
  • D represents a divalent radical of an organic diol that has a molecular weight of less than about 250.
  • the long-chain ester units make up about 35-85% by weight of the copolyester and have the formula (HI)
  • R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350
  • G represents a divalent residue of a long chain glycol which has an average molecular weight of about 350 to 6000.
  • Methods for the synthesis of such copolyesters are known from DOS 2 239 271, DOS 2 213 128, DOS 2449 343 and US Pat. No. 3,023,192
  • Suitable copolyesters are, for example, under the trade names ⁇ ⁇ ytrel from Du Pont,
  • Suitable polyether block amides are, for example, those which consist of polymer chains which are composed of repeating units corresponding to the formula (TV).
  • A is the polyamide chain derived from a polyamide with 2 carboxyl end groups by loss of the latter and
  • B is the polyoxyalkylene glycol chain derived from a polyoxyalkylene glycol with terminal OH groups by loss of the latter, and
  • n is the number of units forming the polymer chain.
  • the end groups here are preferably OH groups or residues of compounds which terminate the polymerization.
  • the dicarboxylic acid polyamides with the terminal carboxyl groups are obtained in a known manner, for example by polycondensation of one or more lactams or / and one or more amino acids, furthermore by polycondensation of a dicarboxylic acid.
  • bonic acid with a diamine in each case in the presence of an excess of an organic dicarboxylic acid, preferably with terminal carboxyl groups.
  • These carboxylic acids become part of the polyamide chain during the polycondensation and attach themselves in particular to the end of the chain, whereby an oc- ⁇ -dicarboxylic acid polyamide is obtained.
  • Fe dicarboxylic acid acts as a chain terminator, which is why it is also used in excess.
  • the polyamide can be obtained starting from lactams and / or amino acids with a hydrocarbon chain consisting of 4-14 C atoms, e.g. of caprolactam, oenantholactam, dodecalactam, undekanolactam, decanolactam, 11-amino-undecanoic or 12-aminododecanoic acid.
  • polyamides such as those formed by polycondensation of a dicarboxylic acid with a diamine
  • condensation products of hexamethylene diamine with adipic, azelaic, sebacic and 1,12-dodecanedioic acid are the condensation products of nonamethylene diamine and adipic acid.
  • those having 4-20 C atoms are suitable, in particular alkanedioic acids such as amber, adipic , Cork, azelaic, sebacic, undecanedioic or dodecanedioic acid, furthermore cycloaliphatic or aromatic dicarboxylic acid, such as terephthalic or isphthalic or cyclohexane-1,4-dicarboxylic acid.
  • the polyoxyalkylene glycols containing terminal OH groups are unbranched or branched and have an alkylene radical with at least 2 carbon atoms.
  • these are polyoxyethylene, polyoxypropylene and polyoxytetramethylene glycol, as well as copolymers thereof.
  • the average molecular weight of these OH group-terminated polyoxyalkylene glycols can be in a wide range, advantageously between 100 and 6000, in particular between 200 and 3000.
  • the proportion by weight of the polyoxyalkylene glycol, based on the total weight of the polyoxyalkylene glycol and dicarboxylic acid polyamide used to produce the PEBA polymer, is 5-85%, preferably 10-50%.
  • EP-S 0 095 893, DOS 2 712 987 and DOS 2 716 004 are known.
  • PEBA polymers which, in contrast to those previously described, have a statistical structure are particularly suitable.
  • Suitable and preferably suitable PEBA polymers are, for example, under the trade names ® PEBAX from Atochem, ® Vestamid
  • the application can be prophylactic as well as therapeutic.
  • the concentration of the active ingredients is preferably 1 to
  • the new formulations can additionally contain other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, etc.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenyl HA nscher, substances produced by microorganisms, etc.
  • the active substances mentioned can be in the liquid, solid preparations as well
  • Shaped bodies are present in a mixture with synergists or other active ingredients.
  • active ingredients include insecticides such as phosphorus-containing compounds, ie phosphoric or phosphonic acid esters, natural or synthetic pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic active ingredients.
  • the phosphoric or phosphoric acid esters include:
  • the carbamates include:
  • the synthetic pyrethroids include compounds of the formula I. in which
  • R 1 and R 2 represent halogen, optionally halogen-substituted alkyl, optionally halogen-substituted phenyl,
  • R 3 represents hydrogen or CN
  • R 4 represents hydrogen or halogen
  • R 5 represents hydrogen or halogen
  • R 1 represents halogen, in particular fluorine, chlorine, bromine,
  • R 2 represents halogen, in particular fluorine, chlorine, bromine, trihalomethyl, phenyl, chloro-phenyl,
  • R 3 represents hydrogen or CN
  • R 4 represents hydrogen or fluorine
  • R 5 represents hydrogen
  • R 2 represents chlorine, trifluoromethyl, p-chloro-phenyl
  • R J stands for CN
  • R> 4 represents hydrogen or fluorine
  • R 1 represents chlorine
  • R 2 represents chlorine or p-chlorophenyl
  • R 3 represents CN
  • R 4 represents fluorine in the 4-position
  • R, 5 represents hydrogen
  • amidines include:
  • Diaryl ether Diaryl ether, benzoyl urea 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 diphenylmethanes of the general formula I
  • 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 5 represents the radicals indicated for R 4 .
  • Het stands for optionally substituted heteroaryl which is not bound to the rest of the group via the heteroatom
  • X, Y independently of one another represent -O-, -S-
  • Z represents -O-, -S-, -CH 2 -, -CHCH 3 -, -C (CH 3 ) 2 -,
  • R 1 is hydrogen, methyl, trifluoromethyl, methoxy, trifluoromethoxy, chlorine, fluorine
  • R represents hydrogen
  • R> 3 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 fluorine, chlorine, methyl, NO 2 , methoxy, methylmercapto,
  • Z represents O, CH 2 or - (CH 3 ) 2 -
  • n 1,
  • n 1
  • Benzoylureas include compounds of the formula (V):
  • R represents halogen
  • R 2 represents hydrogen or halogen
  • R 3 represents hydrogen, halogen or CM-alkyl
  • R 4 represents halogen, 1-5-halogen-C M -alkyl, CM-alkoxy, 1-5-halogen-C M -alkoxy, C M -alkylthio, 1-5-halogen-C M -alkylthio, phenoxy or pyridyloxy which may optionally be substituted by halogen, C M - alkyl, 1-5 halogen C ⁇ .
  • Co-active substance and synergist concentrations can be varied widely in each case from 0.1 to 25% by weight, preferably from 1 to 10% by weight.
  • the following are also interesting: mixtures or combinations of the compounds of the formula (I) with a polyether antibiotic or a synthetically produced coccidiosis.
  • Monensin, salinomycin and maduramicin are preferred from this list.
  • the mixture with maduramicin should be particularly emphasized.
  • Ready-to-use preparations contain the active ingredients in concentrations of 10 ppm to 20 percent by weight, preferably 0.1 to 10 percent by weight.
  • Preparations which are diluted before use contain the active ingredient in concentrations of 0.5 to 90 percent by weight, preferably 1 to 50 percent by weight.
  • the active compounds according to the invention are present in a ratio of 1 to 0.1-10 to 1 to 1-10.
  • the ratio 1 to 5 is preferred.
  • the active ingredients can also be administered together with the animal's feed or drinking water.
  • Feed and food contain 0.01 to 250 ppm, preferably 0.5 to 100 ppm of the active ingredient in combination with a suitable edible material.
  • Such feed and food can be used for medicinal purposes as well as for prophylactic purposes.
  • Such feed or food is produced by mixing a concentrate or a premix which is 0.5 to 30%, preferably 1 to
  • Edible carriers are e.g. Corn meal or corn and soybean meal or mineral salts, which preferably contain a small amount of an edible dust control oil, e.g. Contain corn oil or soybean oil.
  • the premix obtained in this way can then be added to the complete animal feed before it is fed to the animals.
  • Chickens, ducks, geese and turkeys, 0.1 to 100 ppm, preferably 0.5 to 100 ppm, of an active ingredient are mixed with a suitable edible material, for example a nutritious feed. If desired, these amounts can be increased, especially if the active ingredient is well tolerated by the recipient. Accordingly, the administration can take place via the drinking water.
  • a suitable edible material for example a nutritious feed.
  • the administration can take place via the drinking water.
  • amounts of active compound of 0.5 to 100 mg / kg body weight are preferably administered daily in order to achieve the desired results.
  • the activity of the compounds according to the invention can e.g. in cage experiments with the following experimental arrangement, in which the animals are treated with the respective individual components and with the mixtures of the individual components.
  • An active ingredient-containing feed is prepared in such a way that the required amount of active ingredient with a nutritionally balanced animal feed, e.g. is thoroughly mixed with the chick feed specified under.
  • a concentrate or a premix is to be prepared, which is ultimately to be diluted in the feed to the values stated in the experiment, generally about 1 to 30%, preferably about 10 to 20% by weight of active ingredient with an edible organic or inorganic carriers, for example corn and soy flour or mineral salts, which contain a small amount of an edible defatting oil, for example corn oil or soybean oil, are mixed.
  • an edible organic or inorganic carriers for example corn and soy flour or mineral salts, which contain a small amount of an edible defatting oil, for example corn oil or soybean oil.
  • the premix thus obtained can then be added to the whole poultry feed prior to administration.
  • the following composition is an example of the use of the substances according to the invention in poultry feed.
  • feed grain meal namely: 40% corn, 12% wheat
  • Such feed contains 18% crude protein, 5% crude fiber, 1% Ca, 0.7% P and 1200 i.E. per kg. Vitamin A, 1200 i.E. Vitamin D3, 10 mg vitamin E, 20 mg zinc bacitracin.
  • the active ingredient is added to this feed in amounts of e.g. 1 to 20 ppm (w / w) mixed. Suitable dosages of the active ingredient are e.g. 1 ppm; 2.5 ppm; 5 ppm
  • Test animals Adult suckled females of Boophilus mico ⁇ lus (strain
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is added to the
  • the abdomen is injected, the animals are transferred to trays and stored in an air-conditioned room.
  • the effects are checked after 7 days on the laying of fertile eggs. Eggs whose fertility is not externally visible are kept in glass tubes until larvae hatch after about 24 days in a climate cabinet. An effect of 100% means that no tick has laid fertile eggs.
  • Compound A showed 100% activity at 100 ⁇ g (inhibition of the deposit of fertile eggs)
  • a capsule formulation 3 g of active ingredient are fed to 300 kg cattle for three consecutive days.
  • the first larval stages of Musca domestica are set up on dungpobes of the treated cattle and the development to adult flies is compared to the development on manure samples from an untreated control.
  • Such substances are assessed as effective that the
  • Compound A showed 50% efficacy until day 3 after treatment, then a long-lasting 100% efficacy.

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EP03746283A 2002-04-16 2003-04-03 Bekämpfung von parasiten bei tieren Withdrawn EP1496744A1 (de)

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HRP20041064A2 (en) 2006-02-28
DE10216737A1 (de) 2003-10-30
BR0309335A (pt) 2005-03-08
WO2003086075A1 (de) 2003-10-23
KR20040105876A (ko) 2004-12-16
CN1662140A (zh) 2005-08-31
MXPA04010208A (es) 2005-03-07
RU2004133661A (ru) 2005-06-27
AU2003226776A1 (en) 2003-10-27
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