WO2007093296A2 - Formulations d'huile exemptes d'eau servant à lutter contre les arthropodes et les plathelminthes - Google Patents

Formulations d'huile exemptes d'eau servant à lutter contre les arthropodes et les plathelminthes Download PDF

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Publication number
WO2007093296A2
WO2007093296A2 PCT/EP2007/000954 EP2007000954W WO2007093296A2 WO 2007093296 A2 WO2007093296 A2 WO 2007093296A2 EP 2007000954 W EP2007000954 W EP 2007000954W WO 2007093296 A2 WO2007093296 A2 WO 2007093296A2
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WO
WIPO (PCT)
Prior art keywords
oil
formulation according
mixtures
acid
formulation
Prior art date
Application number
PCT/EP2007/000954
Other languages
German (de)
English (en)
Other versions
WO2007093296A3 (fr
Inventor
Thomas Gernot
Petra Krebs
Friedrich Koch
Nikolaus Müller
Beate Tombeux
Original Assignee
Saltigo Gmbh
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 Saltigo Gmbh filed Critical Saltigo Gmbh
Publication of WO2007093296A2 publication Critical patent/WO2007093296A2/fr
Publication of WO2007093296A3 publication Critical patent/WO2007093296A3/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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring

Definitions

  • the present invention relates to a formulation for Arthropoden- and Plathelminthen- defense based on piperidine derivatives in anhydrous oil formulations.
  • ethanol propanol, isopropanol, n-butanol, sec-butanol, propylene glycol, polypropylene glycol, ethylene glycol, polyethylene glycol, ethylene or propylene oxide based copolymeric polyether polyols (both block copolymers and random copolymers), 2-ethyl-1,3 Hexanediol, glycerin, trimethylolpropane, etc.
  • solubility series is given from a ternary system (icaridine, alcohol, water). These mixtures give each stable lotions.
  • the viscosity of the formulations was determined in accordance with DIN 53019 of November 1983:
  • anhydrous oil formulations have become established in the pharmaceutical and cosmetic industries. They consist essentially of ternary systems of an oil component (for example a hydrocarbon mixture, mineral oil, cyclomethicone, linseed oil, apricot kernel oil, oleic acid, pine oil, olive oil, silicone oils, Tallow, Tung OiI, Mink OiI, oleic acid, etc.), a suitable mediating component in the form of one surfactant, for example an emulsifier or emulsifier system, and the actual active ingredient.
  • an oil component for example a hydrocarbon mixture, mineral oil, cyclomethicone, linseed oil, apricot kernel oil, oleic acid, pine oil, olive oil, silicone oils, Tallow, Tung OiI, Mink OiI, oleic acid, etc.
  • a suitable mediating component in the form of one surfactant, for example an emulsifier or emulsifier system, and the actual active ingredient.
  • Insect repellent formulations based on the active ingredient N, N-diethyl-m-toluamide (DEET) are already known.
  • DEET N-diethyl-m-toluamide
  • US 5,916,541 A1 describes emulsions containing an insect repellent, a sunscreen and a film former.
  • US 5,989,529 Al describes emulsions which include a block polmer, a sunscreen agent and optionally a repellent.
  • US 5,980,871 A1 describes emulsions containing an insect repellent, an inorganic sunscreen and an anionic emulsifier.
  • the invention is therefore based on the object to provide stable anhydrous oil formulations which have a low solvent / alcohol content and optionally a high viscosity.
  • the formulations are clear and stable.
  • “Anhydrous” in the sense of the invention means that the formulations contain ⁇ 5.0 wt .-% water, preferably ⁇ 1, 0 wt .-% water, most preferably ⁇ 0.2 wt .-% water.
  • the formulation preferably has a viscosity of> 20 mPas measured according to DIN 53019 from November 1983.
  • the formulation preferably additionally contains from 0.1% to 20% by weight of N-methylpyrrolidone, phenethyl alcohol, benzyl alcohol, an aliphatic alcohol, aliphatic ethers, aliphatic polyethers and / or mixtures thereof. This can increase the stability.
  • the formulation preferably additionally contains 0.1 to 20% by weight of ethanol, propanol, isopropanol, n-butanol, sec-butanol, propylene glycol, polypropylene glycol, ethylene glycol, polyethylene glycol, copolymeric polyether polyols based on ethylene or propylene oxide, 2-ethyl-1, 3-hexanediol, glycerol, trimethylolpropane and / or mixtures thereof.
  • repellent is preferably a piperidine derivative of the general formula:
  • Ri 'and R 2 ' are independently alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloalkoxy, cycloalkeneoxy and cycloalkynoxy, and
  • n 0 or 1 or mixtures thereof are used.
  • a piperidine derivative of the general formula is used where Ri 'and R 2 ' independently of one another for Ci-Ci 2 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, Ci-Ci 2 hydroxyalkyl, C 3 -C 20 hydroxyalkenyl, C 3 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 3 -C 20 cycloalkynyl, C 3 -C 20 cycloalkoxy, C 3 -C 20 cycloalkenoxy and C 3 - C 20 is cycloalkynoxy, and n is 0 or 1, or mixtures thereof.
  • the repellent used is preferably 1-piperidinecarboxylic acid 2-hydroxyethyl-1-methylpropyl ester (icaridine) and 1- (3-cyclohexen-1-ylcarbonyl) -2-methylpiperidine both as a racemic mixture and as a chiral compound, for example (1S, 2'S).
  • 1- (3-cyclohexen-1-ylcarbonyl) -2- used methylpiperidine very particular preference is given to 1-piperidinecarboxylic acid 2-hydroxyethyl-1-methylpropyl ester (icaridine).
  • oils are preferably mineral oils, polycyclic aromatic hydrocarbons, paraffin oils, silicone oils such as polysiloxane, cyclosiloxane, methicone, animal oils such as mink oil, fish oils, natural vegetable oils such as olive oil, sesame oil, linseed oil, palm oil, sunflower oil, peanut oil, rapeseed oil, soybean oil, coconut oil, palm kernel oil, peach kernel oil , Almond oil, castor oil, dehydrated castor oil, pine oil, tall oil and / or mixtures thereof.
  • mineral oils polycyclic aromatic hydrocarbons, paraffin oils, silicone oils such as polysiloxane, cyclosiloxane, methicone, animal oils such as mink oil, fish oils, natural vegetable oils such as olive oil, sesame oil, linseed oil, palm oil, sunflower oil, peanut oil, rapeseed oil, soybean oil, coconut oil, palm kernel oil, peach kernel oil , Almond oil, castor oil, dehydrated castor oil, pine oil
  • aliphatic ester preferably synthetic triglycerides such as caprylic / capric be klarebiglycerid, triglyceride mixtures with vegetable fatty acids of chain length C 8 -i 2 or other natural fatty acids, specifically selected, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also hydroxyl group, mono- and diglycerides of the Cg / io fatty acids , Fatty acid esters such as ethyl stearate, di-n-butyl adipate, hexyl laurate, dipropylene glycol pelargonat, esters of a medium-chain branched fatty acid with saturated fatty alcohols of chain length Ci ⁇ -i ⁇ , isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols of chain length C] 2 I g, isopropyl stearate, isopropyl palmitate, capry
  • Particularly preferred is a formulation containing as a mixture of 1-piperidinecarboxylic acid ethyl-1-methylpropyl, paraffin-based medicinal white oil, isopropyl myristate and propylene glycol.
  • Particularly preferred is a formulation containing 1-piperidinecarboxylic acid-2-hydroxyethyl-1-methylpropyl ester, paraffin-based medicinal white oil and isopropyl palmitate as mixture.
  • the formulation preferably also uses components to produce a UV filter effect.
  • components for producing a UV filter effect are particularly preferred oxybenzone, sulisobenzone (2-hydroxy-4 'methyl benzophenone-5-sulfonic acid), dioxy Benzon (2,2'-dihydroxy-4-methoxybenzophenone), menthyl anthranilate, avobenzone, para aminobenzoic acid , Octylmethoxycinnamate, octocrylene, drometrizoltrisiloxane, octylsalicylate, Homomenthyl salicylate, octyldimethyl-PABA, TEA-salicylate, titanium dioxide, zinc oxide, butylmethoxydibenzoylmethane, methylbenzylidene cameral, octyltriazone, terephthalyldendibandisulfonic acid, ethyl-PABA, hydroxymethylphenyl
  • biocides are preferably additionally used.
  • Particularly preferred biocides are benzyl alcohol, trichlorobutanol, o-phenylphenol, para-hydroxybenzoic acid methyl ester, para-hydroxybenzoic acid ethyl ester, para-hydroxybenzoic acid propyl ester, butyl para-hydroxybenzoate, n-butanol, propanol, isopropanol, ethanol and / or mixtures thereof.
  • antioxidants preference is given to using butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), tocopherol, sulfites, metabisulfites, such as potassium metabisulfite, ascorbic acid, and / or mixtures thereof.
  • Thickening agents are preferably additionally used in the formulation.
  • Particularly preferred thickeners are carboxymethylcellulose, hydroxyethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, polyvinyl acetate, vinyl acetate-crotonic acid copolymer, alginates, gelatin, pectin, casein, agar-agar, gum arabic, aloe vera, polyvinylpyrrolidone, polyvinyl alcohol , Copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, polypropylene glycols, block and / or random copolymer of propylene and ethylene glycol units, waxes, and / or mixtures thereof used.
  • dyes or color pigments it is particularly preferred to use all dyes approved for human or animal use in dissolved or suspended form and as pigments all pigments approved for human or animal use in dissolved or suspended form, and / or mixtures thereof.
  • fragrances are preferably used in addition.
  • Fragrances used are particularly preferably perfume oils and other low-boiling substances which are approved for use on humans or animals, and / or mixtures thereof.
  • the invention also encompasses the use of the formulations for expelling arthropods and / or platelet mints.
  • the formulation is preferably used to ward off harmful or annoying sucking and biting arthropods, preferably insects, ticks and mites used.
  • the invention also encompasses a process for the preparation of the formulation, which comprises 1 to 40% by weight of a repellent
  • the sucking insects mainly include the mosquitoes (for example Aedes aegypti, Aedes vexans, Aedes taeniorhynchus, Aedes albopictus, Culex pipiens fatigans, Culex quinquefasciatus, Culex tarsalis, Anopheles albimanus, Anopheles dirus, Anopheles gambiae, Anopheles sinensis, Anopheles stephensi, Mansonia titillans), butterfly mosquitoes (for example Phlebotomus papatasii, Phlebotomus duboscqi), biting midges (for example Culicoides furens, Culicoides minimctatus), blackflies (for example Simulium damnosum, Simulium venustum), biting flies (for example Stomoxys calcitrans), tsetse flies (for example Glossina mors
  • bugs for example Cimex lectularius, Rhodnius prolixus, Triatoma infestans
  • lice for example Pediculus humanis, Haematopinus suis, Damalina ovis
  • fleas for example Pulex irritans , Xen
  • the biting insects include, essentially, cockroaches (for example, Blattella germanica, Periplaneta americana, Blatta orientalis, Supella longipalpa), beetles (for example, Sitiophilus granarius, Tenebrio molitor, Dermestes lardarius, Stegobium paniceum, Anobium punctatum, Hylotrupes bajulus), termites (e.g.
  • Example Reticulitermes lucifugus ants (for example Lasius niger, Monomorium pharaonis), wasps (for example Vespula germanica) and larvae of moths (for example Ephestia elutella, Ephestia cautella, Plodia interpunctella, Hofmannophila pseudospretella, Tineola bisselliella, Tinea pellionella, Trichophaga tapetzella ).
  • ants for example Lasius niger, Monomorium pharaonis
  • wasps for example Vespula germanica
  • larvae of moths for example Ephestia elutella, Ephestia cautella, Plodia interpunctella, Hofmannophila pseudospretella, Tineola bisselliella, Tinea pellionella, Trichophaga tapetzella ).
  • the other arthropods include ticks (eg Ixodes ricinus, Ixodes scapularis, Argas reflexus, Ornithodorus moubata, Ripicephalus sanguineus, Boophilius microplus, Amblyomma hebraeum) and mites (for example Sarcoptes scabiei, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermanyssus gallinae, Acarus siro) ,
  • ticks eg Ixodes ricinus, Ixodes scapularis, Argas reflexus, Ornithodorus moubata, Ripicephalus sanguineus, Boophilius microplus, Amblyomma hebraeum
  • mites for example Sarcoptes scabiei, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermanyssus gallinae, A
  • the formulations are preferably used against plathelminths, in particular against infectious stages of plathelminths.
  • the formulation is preferred for repelling platelet minneses such as Schistosomahaematobium, Schistosoma japonicum, Trichobilharzia spp. and Ornithobilharzia spp., but also Echinostoma spp. used.
  • the formulations are preferably used by applying to the skin of humans or animals by means of dripping, brushing, rubbing, spraying, by dipping / dipping, bathing or washing.
  • the formulations are preferably used to impregnate a carrier or encapsulation / microencapsulation in a shell of liposomes and / or ureas, or to fill a permeable package or container for later use on the body of a subject.
  • the systems thus obtained can then be used on the body of a living being.
  • the carrier used is preferably tissue, nonwoven, gel and / or polyacrylate.
  • the viscosity is determined according to DIN 53019 of November 1983.
  • the stability of the formulation was determined by the centrifuge microwave assay.
  • the test serves to evaluate the structure of disperse systems. The test method looks like this:
  • test sample of the formulation to be tested is acclimated after preparation for about 2 days at room temperature. Approximately 10 g of product are weighed from the test sample into a centrifuge tube (25 ml nominal volume).
  • the centrifuge tube 1 is 14 (corresponding to an average power of 75 watts) irradiated 75 seconds with stage 1 of the apparatus AEG Micromat ® in the microwave. Subsequently, this sample is acclimated for one hour at room temperature and centrifuged for 11 minutes at 4350 revolutions / minute in an Eppendorf centrifuge 5403.
  • the test of the sample is done visually by the laboratory technician.
  • the sample is examined for homogeneity of the formulation. Differing appearance to the untreated sample, for example occurring phase separation or bubbles in the centrifuge tube are described.
  • a water-free oil formulation of the following composition is prepared:
  • a water-free oil formulation of the following composition is prepared:
  • An anhydrous oil formulation of the following composition is used:
  • An anhydrous oil formulation of the following composition is used:

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

Abstract

L'invention concerne une formulation servant à lutter contre les arthropodes et les plathelminthes, à base de dérivés de pipéridine dans des formulations d'huile exemptes d'eau.
PCT/EP2007/000954 2006-02-16 2007-02-05 Formulations d'huile exemptes d'eau servant à lutter contre les arthropodes et les plathelminthes WO2007093296A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006007544.7 2006-02-16
DE200610007544 DE102006007544A1 (de) 2006-02-16 2006-02-16 Wasserfreie Öl-Formulierung zur Arthropoden- und Plathelminthen-Abwehr

Publications (2)

Publication Number Publication Date
WO2007093296A2 true WO2007093296A2 (fr) 2007-08-23
WO2007093296A3 WO2007093296A3 (fr) 2008-11-27

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DE (1) DE102006007544A1 (fr)
WO (1) WO2007093296A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2010275768B2 (en) * 2009-07-24 2015-07-23 G. Pohl-Boskamp Gmbh & Co. Kg Means for controlling ectoparasites

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012206961A1 (de) 2012-04-26 2013-10-31 Robert Bosch Gmbh Pumpe mit Elektromotor

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993016594A1 (fr) * 1992-02-27 1993-09-02 Perycut-Chemie Ag Insectifuge
WO2002043489A1 (fr) * 2000-11-28 2002-06-06 Avon Products, Inc. Composition repulsive anhydre pour insectes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993016594A1 (fr) * 1992-02-27 1993-09-02 Perycut-Chemie Ag Insectifuge
WO2002043489A1 (fr) * 2000-11-28 2002-06-06 Avon Products, Inc. Composition repulsive anhydre pour insectes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2010275768B2 (en) * 2009-07-24 2015-07-23 G. Pohl-Boskamp Gmbh & Co. Kg Means for controlling ectoparasites

Also Published As

Publication number Publication date
WO2007093296A3 (fr) 2008-11-27
DE102006007544A1 (de) 2007-08-30

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