WO2018050211A1 - Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée - Google Patents

Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée Download PDF

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Publication number
WO2018050211A1
WO2018050211A1 PCT/EP2016/071593 EP2016071593W WO2018050211A1 WO 2018050211 A1 WO2018050211 A1 WO 2018050211A1 EP 2016071593 W EP2016071593 W EP 2016071593W WO 2018050211 A1 WO2018050211 A1 WO 2018050211A1
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WO
WIPO (PCT)
Prior art keywords
cyclodextrin
insect repellent
formulation
oil
formulation according
Prior art date
Application number
PCT/EP2016/071593
Other languages
German (de)
English (en)
Inventor
Ingo Jeschke
Markus Sailer
Original Assignee
Wacker Chemie 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 Wacker Chemie Ag filed Critical Wacker Chemie Ag
Priority to PCT/EP2016/071593 priority Critical patent/WO2018050211A1/fr
Publication of WO2018050211A1 publication Critical patent/WO2018050211A1/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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system

Definitions

  • the invention relates to a cyclodextrin-containing formulation for controlling and repelling insects having an improved activity, which can be used for application to the skin of humans or animals, as well as for the treatment of surfaces, in particular of textiles.
  • Many insects will be ⁇ seeks as pests for humans and animals because they are regarded as vectors for disease transmission. In addition, they can cause damage to agricultural products and can sometimes be viewed as a massive annoyance when staying outdoors. These insects are ants, bedbugs, sand fleas, dust mites, fleas,
  • mosquitoes Flies, lice, termites, wasps and especially mosquitoes are counted. Many mosquitoes can transmit life-threatening diseases as so-called vectors.
  • Aedes aegypti is a vector for dengue fever and yellow fever, Anopheles for malaria, Glossina for sleeping sickness and Culex for West Nile disease.
  • One way to prevent mosquito bites is to apply insect repellents to the skin.
  • insect repellents and insect repellents can be applied to textiles and mosquito nets to shield people from insects that protect themselves with these textiles. Finally, these substances are also applied to surfaces for deterring and eliminating insects, such as house walls.
  • the active ingredient DEET (N, -diethyl-m-toluamide) is used as an extremely effective insect repellent, which still serves as a golden standard and is used in concentrations of up to 50%.
  • DEET -diethyl-m-toluamide
  • insect repellents based on DEET are preferably used with the lowest possible active substance concentration. Unfortunately, the protection time decreases with a decrease in the active ingredient ⁇ concentration sometimes very strong.
  • Examples of alternatives to DEET are Icaridin (1- (1-methylpropoxycarbonyl) -2- (2-hydroxyethyl) piperidine), which is synthesized from the plant compound piperidine.
  • the protective agent IR3535 (Ethylbutylacetylaminopropio- nat) is used, which, however, compared to the first two drugs mentioned has a much lower protection time.
  • natural insect repellents are becoming increasingly popular, which mainly uschhe ⁇ innovative oils include. Many oils such as citronella oil, camphor oil or thymol have a very low protection time due to their high volatility.
  • Citriodiol® or PMD (p-menthane-3, 8-diol) mentioned which was originally obtained from the leaves of the lemon eucalyptus and hay ⁇ te is also produced synthetically. It can be achieved with PMD about the same protective effect, as with low DEET concentrations.
  • volatile pyrethrins or pyrethroids are used both for defense and control of insects.
  • Representatives of these volatile pyrethroids may include, for example, the following substances: empenthrin, profuthrin, transfluthrin, furamethrin, metofluthrin, allethine, prallethrin, phenothrin or permethrin.
  • Cyclodextrins are cyclic oligosaccharides which contain six ( ⁇ -), seven ( ⁇ -) or eight ( ⁇ -) linked D- glucopyranose units via ⁇ - (1,4) bonds and which are obtained enzymatically from starch. Due to their ring-shaped molecular structure with a hydrophobic cavity, cyclo- dextrins reversible complexes with hydrophobic guest molecules bil ⁇ the. Due to the hydrophilic surface of the water solubility of cyclodextrins hydrophobins ⁇ ben substances can be greatly improved with their help.
  • cyclodextrin complexes Prerequisite for the formation of cyclodextrin complexes are a suitable size and geometry of the guest molecule, so that they at least partially fit into the cavity of the cyclodextrin to form intermolecular interactions can. Lent additional must hydrophobic molecular areas aufwei ⁇ sen the guest molecules.
  • cyclodextrin derivatives have been proposed, which can be attached to textiles by means of the reactive group of a derivatization, in order then to be loaded with insect repellents, such as the DEET (Angelo Marco Ranaldo, 2005, EP
  • the cyclodextrin is used in a molar excess, which only led to an unzu ⁇ reaching improvement in insect repellent activity and as insect repellent.
  • the object of the invention was to improve formulations containing insect repellents or insect repellents together with cyclodextrins in such a way that an increase in the efficacy can be made possible.
  • This object is achieved by a formulation containing an insect repellent or an insect repellent, and a cyclodextrin or cyclodextrin derivative, characterized in that the cyclodextrin or cyclodextrin derivative is present in a significant molar deficit against the insect repellent or the insect repellent.
  • the cyclodextrin must be applied either equimolar or in excess in relation to the active ingredients in order to achieve the fullest possible complexation of the active ingredients. It turned out that the application of this principle in the case of insects ⁇ protection products and insect repellents did not result in significant improvement in efficacy.
  • the majority of the active ingredients are applied to the components by an equimolar use of the cyclodextrins or an excess of the cyclodextrins Surface bound that too low an active ingredient content can be released into the ambient air, so as to cause an effect on the presence of insects.
  • a clear deficit of cyclodextrin is applied, a sufficiently large proportion of the active substance can be released into the ambient air immediately after the application of the agent in order to be able to show an effect on insects.
  • the proportion of cyclodextrin complex additionally contained in the deficit leads to a continuous release of further active substance, so that the duration of action can be significantly prolonged compared to the pure active substance.
  • the ratio of the insect repellent or insect repellent ⁇ agent to the cyclodextrin or the cyclodextrin derivative is preferably in the range between 1: 0.01 and 1: 0.4 (mole:
  • the cyclodextrin is preferably a natural cyclodextrin selected from the group consisting of .alpha.-cyclodextrin, .beta.-cyclodextrin and .gamma.-cyclodextrin, and mixtures thereof or a cyclodextrin derivative selected from the group consisting of hydroxypropyl .alpha.-cyclodextrin, Acetyl-a-cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, hydroxypropyl-y-cyclodextrin, acetyl- ⁇ -
  • the cyclodextrin is particularly preferably a-cyclodextrin, .beta.-cyclodextrin or .gamma.-cyclodextrin and mixtures thereof and the cyclodextrin derivative is hydroxypropyl-.alpha.-cyclodextrin, hydroxypropyl-.beta.-cyclodextrin, methyl-.beta. Cyclodextrin or hydroxypropyl-y-cyclodextrin and mixtures thereof.
  • the active ingredient comes from the group of the following substances and mixtures thereof: azadirachtin, carpromine, 1,8-cineole, citral, citronellal, citronellol, ethylbutylacetylaminopropionate, eugenol, eucalyptus oil, geraniol, I-caridine, camphor oil, lavender oil, limonene , Linalool, clove oil, nepetalactone, N, -diethyl-m-toluamide, peppermint oil, p-menthane-3,8-diol, ⁇ -terpinene, thymol, vanillin, cinnamon oil and citrusgrass oil.
  • azadirachtin carpromine, 1,8-cineole, citral, citronellal, citronellol, ethylbutylacetylaminopropionate, eugenol, eucalyptus oil, geraniol
  • insects protective properties of each active ingredient can be used that kills ⁇ Due to its chemical nature insects.
  • the insect repellent is preferably a volatile insect repellent. Under preferential ⁇ example is understood to be “volatile” means that the insect repellent has a vapor pressure of greater than 1.0 ⁇ * 10 -7 Pa at 20 ° C.
  • the active ingredient is from the group of pyrethrins and pyrethroids and mixtures thereof: empenthrin, esfenfalerate, fenpropathrin, profuthrin, tefluthrin, transfluthrin, furemathrin, metofluthrin, allethrin, prallethrin, phenothrin and permethrin.
  • the preparation of the insecticidal composition is carried out in a manner known per se by combining the stated components in the stated amounts into a formulation.
  • insect repellent or insect-protecting agents can be either in the form of a physical mixture with used cyclodextrin or used as a combination of cyclodextrin complex and physical mixture.
  • the cyclodextrin complexes are preferably prepared by the co-precipitation process, the melting-in process or the paste process.
  • the insecticide is dissolved in a solvent and added in said ratio to an aqueous solution of the cyclodextrin or cyclodextrin derivative heated to 20 to 70 ° C, preferably to 50 ° C.
  • the solution is stirred for a period of 16 hours and then the solvent is removed.
  • the residue is dried at 40.degree.
  • the solvent is preferably acetone, methanol or ethanol.
  • the cyclodextrin or cyclodextrin derivative is initially charged in water and heated to 20 to 70 ° C, preferably 50 ° C.
  • the insecticide is added in portions and stirred for 16 hours at said temperature.
  • Not complexed x jewes insecticide is filtered and the complex by freeze-drying Ge ⁇ isolated.
  • the cyclodextrin or the cyclodextrin derivative are mixed together with the insecticide in the desired ratio and water added in an amount of 30 weight percent ⁇ the two components.
  • the resulting paste is held for a period of eight hours at 70 ° C in a closed glass vessel and mixed hourly by means of a spatula. After the eight hours, the paste is dried and ground for further use.
  • the preparation of the formulation according to the invention is carried out by combining said components in the stated amounts to formulate a formulation.
  • a formulation for this purpose, either the insulating th cyclodextrin complexes or the pure cyclodextrins incorporated together with the active ingredients by stirring in a solvent mixture that consists of water and alcohol.
  • additional formulation ingredients such as preservatives, fragrances or else as moisturizing components can be incorporated as desired.
  • these are usually used in insect repellants or insect repellents components in the usual amounts.
  • the invention further relates to a method for protection against insects which is characterized in that the invention shown SSE formulation is applied to a surface. ⁇ preference as it is at the surface of a skin surface or wall of a house or a textile surface or other
  • the application of the formulation can be done for example by spraying or brushing.
  • the method according to the invention makes it possible to defend and combat insects by significantly prolonging the duration of action of the insect repellents and volatile insect repellents, which is made possible by the use of certain cyclodextrins in excess in relation to the active substances. This ensures that some of the active ingredients are released into the ambient air with a delay, which significantly extends the duration of the active ingredients.
  • EXAMPLE 1 Preparation of an Insect Repellent Formulation Based on DEET (N, N-Diethyl-m-Toluamide) and the Hydroxypropylated Beta-Cyclodextrin (HP- ⁇ -CD)
  • DEET N, N-Diethyl-m-Toluamide
  • HP- ⁇ -CD Hydroxypropylated Beta-Cyclodextrin
  • Example 3 Preparation of an insect repellent formulation based on DEET (N, N-diethyl-m-toluamide) and beta-cyclodextrin ( ⁇ -CD)
  • Example 4 Preparation of an insect repellent formulation based on DEET (N, N-diethyl-m-toluamide) and alpha-cyclodextrin (a-CD)
  • DEET N, N-diethyl-m-toluamide
  • a-CD alpha-cyclodextrin
  • Example 5 Results of mosquito tests A cage test was carried out to examine the formulations for their insect repellent effect.
  • cages were used with closable openings at the bottom, which were each occupied by 30-40 female mosquitoes (Aedes aegypty) in Al ⁇ ter from 5-8 days.
  • the room temperature during the test was 22.4 ° C ( ⁇ 0.2 ° C) and the humidity was 53% ( ⁇ 3%).
  • All formulations were tested on two subjects.
  • 200 ⁇ of the formulation was applied to a skin area of about 100 cm 2 .
  • the skin was pre-cleaned with isopropanol.
  • the first test was started.
  • the treated skin surface was held to the cage opening for 2 minutes and all landings and stings documented.
  • the active ingredient was considered effective until the second sting. If no abort criterion was present, the test was repeated every 30 minutes.
  • Example 6 Preparation of the cyclodextrin complex of DEET (N, N-diethyl-m-toluamide) with alpha-cyclodextrin ( ⁇ -CD) after melting
  • a-CD (20 g) is dissolved in 180 ml of water and at 50 ° C. heated.
  • DEET N, -diethyl-m-toluamide
  • 15.72 g is added portionwise to the cyclodextrin solution.
  • the solution is stirred for 16 hours at 50 ° C and then filtered off the cyclodextrin complex formed.
  • the precipitate is analytically examined under ⁇ .
  • Example 7 Preparation of an insect repelling formulation based on the cyclodextrin complex formed in Example 6
  • Example 8 Preparation of the cyclodextrin complex of DEET (N, N-diethyl-m-toluamide) with the hydroxypropylated beta-cyclodextrin (HP- ⁇ -CD) according to the melting in process HP-jss-CD (10 g) is dissolved in 90 ml of water and heated to 50 ° C ⁇ . DEET (N-diethyl-m-toluamide) (3.27 g) is added dropwise to the portions ⁇ cyclodextrin added. The solution is stirred for 16 hours at 50 ° C. and then the cyclodextrin complex formed is filtered off. The precipitate is analyzed analytically.
  • Example 9 Preparation of an insect repelling formulation based on the cyclodextrin complex formed in Example 8. To prepare an insect repellent formulation, 9.89 g of the cyclodextrin complex mentioned in Example 1 are mixed together with 52.6 g of ethanol and 40.0 g of water.
  • Example 10 Preparation of the cyclodextrin complex of PMD (p-menthane-3,8-diol) with beta-cyclodextrin ( ⁇ -CD) after melting
  • ⁇ -CD beta-cyclodextrin
  • ⁇ -CD beta-cyclodextrin
  • Example 11 Preparation of an insect repelling formulation based on the cyclodextrin complex formed in Example 10 To prepare an insect repellent formulation, 10.0 g of the cyclodextrin complex mentioned in Example 10 are mixed together with 52.6 g of ethanol and 40.0 g of water.

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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 une formulation contenant un répulsif à insectes ou un agent de protection contre les insectes, ainsi qu'une cyclodextrine ou un dérivé de cyclodextrine, cette formulation étant caractérisée en ce que la cyclodextrine ou le dérivé de cyclodextrine est présent dans une quantité molaire nettement inférieure à celle du répulsif à insectes ou de l'agent de protection contre les insectes.
PCT/EP2016/071593 2016-09-13 2016-09-13 Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée WO2018050211A1 (fr)

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PCT/EP2016/071593 WO2018050211A1 (fr) 2016-09-13 2016-09-13 Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108378081A (zh) * 2018-04-28 2018-08-10 湖北民族学院 一种天然中草药驱蚊凝胶剂及其制备方法
CN111213679A (zh) * 2020-02-27 2020-06-02 无锡迈莱博生物科技有限公司 植物除螨抑菌液及其制备方法和应用
EP3763212A1 (fr) 2019-07-11 2021-01-13 SanderStrothmann GmbH Composition répulsive pour arthropodes
CN113967266A (zh) * 2021-11-12 2022-01-25 北京斯瑞朗文生物科技有限公司 N,n-二乙基-2-羟基-2-苯乙酰胺环糊精包合物及其制备方法与应用
WO2022105987A1 (fr) 2020-11-17 2022-05-27 Wacker Chemie Ag Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs
WO2022156882A1 (fr) 2021-01-19 2022-07-28 Wacker Chemie Ag Formulations contenant de la cyclodextrine et des acides gras pour combattre et repousser les insectes ayant un effet amélioré
CN115590016A (zh) * 2022-10-26 2023-01-13 中南大学湘雅三医院（Cn） 一种肿瘤样本保存装置
WO2023006190A1 (fr) 2021-07-28 2023-02-02 Wacker Chemie Ag Formulations contenant de la cyclodextrine pour des substances volatiles avec des additifs afin de maintenir une libération constante

Citations (4)

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US3846551A (en) * 1972-11-20 1974-11-05 Teijin Ltd Insecticidal and acaricidal composition and process for controlling pests
DE202004014465U1 (de) * 2004-09-15 2004-12-30 Ahrenshof Vermögensverwaltungs GmbH Repellentien zum Schutz gegen Insekten
WO2006077604A1 (fr) * 2005-01-19 2006-07-27 Pointex S.P.A. Complexe d'inclusion entre un derive de cyclodextrine et une substance a activite repulsive contre les insectes nuisibles et/ou genants, formulations et utilisations associees
WO2009090140A1 (fr) * 2008-01-17 2009-07-23 Wacker Chemie Ag Émulsion aqueuse contenant un dérivé de cyclodextrine, une substance odorante et un polysorbate

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US3846551A (en) * 1972-11-20 1974-11-05 Teijin Ltd Insecticidal and acaricidal composition and process for controlling pests
DE202004014465U1 (de) * 2004-09-15 2004-12-30 Ahrenshof Vermögensverwaltungs GmbH Repellentien zum Schutz gegen Insekten
WO2006077604A1 (fr) * 2005-01-19 2006-07-27 Pointex S.P.A. Complexe d'inclusion entre un derive de cyclodextrine et une substance a activite repulsive contre les insectes nuisibles et/ou genants, formulations et utilisations associees
WO2009090140A1 (fr) * 2008-01-17 2009-07-23 Wacker Chemie Ag Émulsion aqueuse contenant un dérivé de cyclodextrine, une substance odorante et un polysorbate

Non-Patent Citations (2)

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Title
PRONIUK STEFAN ET AL: "Topical formulation studies with DEET (N,N-diethyl-3-methylbenzamide) and cyclodextrins", JOURNAL OF PHARMACEUTICAL SCIENCES, AMERICAN PHARMACEUTICAL ASSOCIATION, WASHINGTON, US, vol. 91, no. 1, 1 January 2002 (2002-01-01), pages 101 - 110, XP009191964, ISSN: 0022-3549 *
USHA RASHMI BHASKARA-AMRIT ET AL: "APPLICATIONS OF [beta] -CYCLODEXTRINS IN TEXTILES", AUTEX RESEARCH JOURNAL, vol. 11, no. 4, 1 December 2011 (2011-12-01), pages 94 - 101, XP055308823 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108378081A (zh) * 2018-04-28 2018-08-10 湖北民族学院 一种天然中草药驱蚊凝胶剂及其制备方法
EP3763212A1 (fr) 2019-07-11 2021-01-13 SanderStrothmann GmbH Composition répulsive pour arthropodes
WO2021005206A1 (fr) 2019-07-11 2021-01-14 Sanderstrothmann Gmbh Composition répulsive d'arthropodes
US11503831B2 (en) 2019-07-11 2022-11-22 Sanderstrothmann Gmbh Arthropoda repellent composition
CN111213679A (zh) * 2020-02-27 2020-06-02 无锡迈莱博生物科技有限公司 植物除螨抑菌液及其制备方法和应用
WO2022105987A1 (fr) 2020-11-17 2022-05-27 Wacker Chemie Ag Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs
WO2022156882A1 (fr) 2021-01-19 2022-07-28 Wacker Chemie Ag Formulations contenant de la cyclodextrine et des acides gras pour combattre et repousser les insectes ayant un effet amélioré
WO2023006190A1 (fr) 2021-07-28 2023-02-02 Wacker Chemie Ag Formulations contenant de la cyclodextrine pour des substances volatiles avec des additifs afin de maintenir une libération constante
CN113967266A (zh) * 2021-11-12 2022-01-25 北京斯瑞朗文生物科技有限公司 N,n-二乙基-2-羟基-2-苯乙酰胺环糊精包合物及其制备方法与应用
CN115590016A (zh) * 2022-10-26 2023-01-13 中南大学湘雅三医院（Cn） 一种肿瘤样本保存装置

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