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CA2538363A1 - Insect repellent compositions comprising dihydronepetalactone - Google Patents

Insect repellent compositions comprising dihydronepetalactone Download PDF

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Publication number
CA2538363A1
CA2538363A1 CA002538363A CA2538363A CA2538363A1 CA 2538363 A1 CA2538363 A1 CA 2538363A1 CA 002538363 A CA002538363 A CA 002538363A CA 2538363 A CA2538363 A CA 2538363A CA 2538363 A1 CA2538363 A1 CA 2538363A1
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CA
Canada
Prior art keywords
composition
dihydronepetalactone
insects
group
stereoisomers
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.)
Granted
Application number
CA002538363A
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French (fr)
Other versions
CA2538363C (en
Inventor
David L. Hallahan
Leo E. Manzer
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EIDP Inc
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Individual
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Publication of CA2538363A1 publication Critical patent/CA2538363A1/en
Application granted granted Critical
Publication of CA2538363C publication Critical patent/CA2538363C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • 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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen as the 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pest Control & Pesticides (AREA)
  • Epidemiology (AREA)
  • Plant Pathology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Fats And Perfumes (AREA)

Abstract

Dihydronepetalactone, a minor natural constituent of the essential oil of catmints (Nepeta spp.) such as Nepeta cataria, has been identified as an effective insect repellent compound. Synthesis of dihydronepetalactone may be achieved by hydrogenation of nepetalactone, the major constituent of catmint essential oils. This compound, which also has fragrance properties, may be used commercially for its insect repellent properties.

Claims (25)

1. A composition of matter that repels insects when applied to a human, animal or inanimate host comprising a dihydronepetalactone, or a mixture of dihydronepetalactone stereoisomers, represented by the general formula:

2. The composition of Claim 1 wherein the dihydronepetalactone stereoisomers are (9S)-dihydronepetalactone stereoisomers derived from (7S)-nepetalactones.
3. The composition of Claim 1 which comprises 1S,9S,5R,6R-5,9-dimethyl-3-oxabicyclo[4.3.0]nonan-2-one.
4. The composition of Claim 1 which comprises dihydronepetalactone in an amount of from about 0.001% to about 80% by weight of the total weight of the composition.
5. The composition of Claim 1 which comprises dihydronepetalactone in an amount of from about 0.01% to about 30% by weight of the total weight of the composition.
6. The composition of Claim 1 which comprises one or more of the members of the group consisting of an adjuvant, a carrier and an insect repellent compound that is not a dihydronepetalactone.
7. The composition of Claim 6, wherein the adjuvant is selected from the group consisting of thickeners, buffering agents, chelating agents, preservatives, fragrances, antioxidants, gelling agents, stabilizers, surfactants, emolients, coloring agents, aloe vera, waxes, and therapeutically or cosmetically active ingredients.
8. The composition of Claim 6, wherein the carrier is selected from the group consisting of silicone, petrolatum, lanolin, liquid hydrocarbons, agricultural spray oils, paraffin oil, tall oils, liquid terpene hydrocarbons and terpene alcohols, aliphatic and aromatic alcohols, esters, aldehydes, ketones, mineral oil, higher alcohols, finely divided organic and inorganic solid materials.
9. The composition of Claim 6, wherein the carrier comprises an aerosol composition adapted to disperse the dihydronepetalactone into the atmosphere by means of a compressed gas.
10. The composition of Claim 6, wherein the non-hydronepetalactone insect repellent is selected from the group consisting of: benzil, benzyl benzoate, 2,3,4,5-bis(butyl-2-ene) tetrahydrofurfural, butoxypolypropylene glycol, N-butylacetanilide, normal-butyl-6,6-dimethyl-5,6-dihydro-1,4-pyrone-2-carboxylate, dibutyl adipate, dibutyl phthalate, di-normal-butyl succinate, N,N-diethyl-meta-toluamide, dimethyl carbate, dimethyl phthalate, 2-ethyl-2-butyl-1,3-propanediol, 2- ethyl-1,3-hexanediol, di-normal-propyl isocinchbmeronate, 2-phenylcyclohexanol, p-methane-3,8-diol, and normal-propyl N, N- diethylsuccinamate.
11. The composition of Claim 1 which is repellent to insects comprising biting insects, wood-boring insects, noxious insects, and household pest insects.
12. The composition of Claim 1 which is repellent to one or more of mosquitoes, stable flies and ticks.
13. The composition of Claim 1 which is in the form of a cologne, a lotion, a spray, a cream, a gel, an ointment, a bath or shower gel, a foam product, makeup, a deodorant, shampoo, a hair lacquer or rinse or a personal soap.
14. The composition of Claim 1 which is in the form of an insect repellent article of manufacture.
15. The article of Claim 14 which is selected from the group consisting of air freshener, a candle, a scented articles, a fiber, a sheets, cloth, paper, paint, ink, clay, wood, furniture, carpeting, sanitary goods, a plastic, and a polymer.
16. A composition of matter that repels one or more insects selected from the group consisting of bees, black flies, chiggers, fleas, green head flies, mosquitoes, stable flies, ticks, wasps, wood-boring insects, houseflies, cockroaches, lice, roaches, wood lice, flour and bean beetles, dust mites, moths, silverfish; and weevils, comprising a dihydronepetalactone, or a mixture of dihydronepetalactone stereoisomers, represented by the general formula:

17. A composition of matter that has a mean complete protection time that is statistically indistinguishable from that of N,N-diethyl-m-toluamide comprising a dihydronepetalactone, or a mixture of dihydronepetalactone stereoisomers, represented by the general formula:

18. A method of repelling insects from a human, animal or inanimate host comprising exposing the insects to a dihydronepetalactone, or a mixture of dihydronepetalactone stereoisomers, represented by the general formula:
19. The use of a dihydronepetalactone, or a mixture of dihydronepetalactone stereoisomers, represented by the general formula:

to repel insects from a human, animal or inanimate host.
20. A process for the production of a dihydronepetalactone of formula (XVI) comprising hydrogenating a nepetalactone of formula (XV) according to the following scheme:
in the presence of palladium supported on a catalyst support that is not SrCO3.
21. The process as recited in Claim 20 wherein the catalyst support is selected from the group consisting of carbon, alumina, silica, silica-alumina, titanic, titanic-alumina, titanic-silica, barium, calcium, compounds thereof, and combinations thereof.
22. The process as recited in Claim 20 wherein the catalyst support is carbon.
23. The process as recited in Claim 20 wherein the palladium content is from about 0.1% to about 20%.
24. The process as recited in Claim 20 which is effected in the presence of a metal promoter.
25. The process as recited in Claim 20 which is performed at a temperature of about 25°C to about 250°C and a pressure of about 0.1 MPa to about 20 MPa.
CA2538363A 2003-09-18 2003-09-18 Insect repellent compositions comprising dihydronepetalactone Expired - Fee Related CA2538363C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2003/029344 WO2005034626A1 (en) 2003-09-18 2003-09-18 Insect repellent compositions comprising dihydronepetalactone

Publications (2)

Publication Number Publication Date
CA2538363A1 true CA2538363A1 (en) 2005-04-21
CA2538363C CA2538363C (en) 2012-01-10

Family

ID=34434203

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2538363A Expired - Fee Related CA2538363C (en) 2003-09-18 2003-09-18 Insect repellent compositions comprising dihydronepetalactone

Country Status (8)

Country Link
EP (1) EP1681925A4 (en)
JP (1) JP2007521240A (en)
CN (2) CN1838881A (en)
AU (1) AU2003270748A1 (en)
BR (1) BR0318501A (en)
CA (1) CA2538363C (en)
IL (1) IL173903A0 (en)
WO (1) WO2005034626A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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US9878464B1 (en) 2011-06-30 2018-01-30 Apinee, Inc. Preservation of cellulosic materials, compositions and methods thereof

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JP2008519050A (en) * 2004-11-03 2008-06-05 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Insect repellent composition comprising dihydronepetalactone, alcohol, and ester
US7407922B2 (en) 2005-10-13 2008-08-05 S.C. Johnson & Son, Inc. Deodorizing compositions
US7261742B2 (en) 2005-10-13 2007-08-28 S.C. Johnson & Son, Inc. Method of deodorizing a textile
EP2040555A2 (en) * 2006-05-10 2009-04-01 E.I. Du Pont De Nemours And Company Formulated tick and insect repellent compositions
ES2498667T3 (en) * 2006-12-21 2014-09-25 E. I. Du Pont De Nemours And Company Hydrogenation of nébeda oil
US8765975B2 (en) 2006-12-21 2014-07-01 E I Du Pont De Nemours And Company Production of dihydronepetalactone
DE102007026051A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Insect repellent with reduced stickiness
DE102007026049A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Repellents against wasps
DE102007026050A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Insect repellent and thickener
DE102007026048A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Insect repellent and perfume
DE102007026053A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Insect repellent with good skin compatibility
DE102007026052A1 (en) 2007-05-31 2008-12-04 Beiersdorf Ag Insect repellents on an emulsion basis
JP5805099B2 (en) * 2009-11-11 2015-11-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ Methods to improve recovery of catnip oil
US20150201615A1 (en) * 2012-06-28 2015-07-23 Tyratech, Inc. Insect repellent surface composition
DE102013217239A1 (en) 2013-08-29 2015-03-05 Beiersdorf Ag Emulsifier-free, skin-conditioning cosmetic or dermatological preparation with repellents
KR101709114B1 (en) * 2015-03-30 2017-02-22 김수학 A aqua bead Insect Repellent and Its Production Method
KR101800227B1 (en) * 2017-01-24 2017-11-24 김수학 A Insect Repellent Using Aagar Powder and Its Production Method
CN109497101A (en) * 2018-11-28 2019-03-22 湖州世轩丝绸进出口有限公司 A kind of spray and preparation method thereof preventing fabric moth
CN114324645B (en) * 2021-12-24 2023-10-24 广州白云山汉方现代药业有限公司 Method for rapidly identifying Tibetan schizonepeta herb

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US4663346A (en) * 1984-05-30 1987-05-05 Angus Chemical Company Insect repellent
DE60322340D1 (en) * 2002-01-23 2008-09-04 Du Pont fragrance CONNECTION
US20030235601A1 (en) * 2002-03-20 2003-12-25 Hallahan David L. Insect repellent compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9878464B1 (en) 2011-06-30 2018-01-30 Apinee, Inc. Preservation of cellulosic materials, compositions and methods thereof

Also Published As

Publication number Publication date
IL173903A0 (en) 2006-07-05
BR0318501A (en) 2006-09-12
CN101396020B (en) 2014-10-29
AU2003270748A1 (en) 2005-04-27
EP1681925A4 (en) 2008-07-02
CN1838881A (en) 2006-09-27
CA2538363C (en) 2012-01-10
EP1681925A1 (en) 2006-07-26
WO2005034626A1 (en) 2005-04-21
JP2007521240A (en) 2007-08-02
CN101396020A (en) 2009-04-01
AU2003270748A2 (en) 2005-04-27

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Effective date: 20210920