WO2003013243A1 - Insect repellents - Google Patents

Insect repellents Download PDF

Info

Publication number
WO2003013243A1
WO2003013243A1 PCT/GB2002/003369 GB0203369W WO03013243A1 WO 2003013243 A1 WO2003013243 A1 WO 2003013243A1 GB 0203369 W GB0203369 W GB 0203369W WO 03013243 A1 WO03013243 A1 WO 03013243A1
Authority
WO
WIPO (PCT)
Prior art keywords
insect repellent
fragrance
repellent fragrance
weight
product
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.)
Ceased
Application number
PCT/GB2002/003369
Other languages
French (fr)
Inventor
Richard Arthur Birch
Henk Helweg
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.)
Givaudan Nederland Services BV
Original Assignee
Quest International BV
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 Quest International BV filed Critical Quest International BV
Priority to AT02749049T priority Critical patent/ATE307482T1/en
Priority to BR0211177-2A priority patent/BR0211177A/en
Priority to EP02749049A priority patent/EP1414298B1/en
Priority to DE60206929T priority patent/DE60206929T2/en
Priority to US10/486,423 priority patent/US7455852B2/en
Publication of WO2003013243A1 publication Critical patent/WO2003013243A1/en
Anticipated expiration legal-status Critical
Ceased 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof

Definitions

  • the present invention relates to fragrances, particularly insect repellent fragrances, to products comprising such fragrances and to a method of repelling insects.
  • Insects have long been known to be a nuisance to humans, and for some insect genera, a health hazard.
  • cockroaches e.g. American cockroaches (periplaneta americana) and German cockroaches (blattella germanica)
  • cockroaches e.g. American cockroaches (periplaneta americana) and German cockroaches (blattella germanica)
  • chemical compounds e.g. N,N-diethyl-meta-toluamide, which are efficacious in repelling cockroaches.
  • Such chemical compounds are used in the household by applying or spraying them to surfaces of walls, floors, cabinets, containers, rugs, upholstery and carpeting, and in potential nesting places for these insects, such as inside walls and between floors.
  • Chemical compounds have been used together with hard surface cleaners (EP-A-0619363) and wax floor polishes (US-A-3018217).
  • WO 96/08147 describes an insect repellent composition comprising at least one active ingredient from the group of compounds consisting of: 1,2, 3a, 4, 5, 5a, 6, 7, 8, 9, 9a, 9b- dodecahydro-3a,6,6,9a-tetramethylnaphtho [2, 1-b] furan (AMBERLYNTM); 4-(tricyclo [5.2.1.0 2 6 ] decylidene-8) butanal (DUPICALTM); l-ethoxy-l-(2'-phenylethoxy) ethane (EFETAALTM); acetyl cedrene (LIXITONETM); and propylidene phthalide.
  • the compositions are described as preferably used to repel biting insects, such as mosquitoes, and in particular members of the genus Ae
  • American cockroaches periplaneta ame ⁇ cana
  • Ngoh S.P. et al. Pestic. Sci. , 1998, 54, p261
  • German cockroaches blattella germanica
  • JP 2207004 German cockroaches
  • it is difficult to formulate a complete fragrance which effectively repels cockroaches, particularly German cockroaches, and more particularly, repels both German and American cockroaches, possibly together with other crawling insects e.g. ants.
  • the present invention provides an insect repellent fragrance comprising;
  • insect repellent fragrance comprises at least 60% by total weight of the insect repellent fragrance of (a), (b) and (c).
  • the present invention is based on the appreciation that insect repellent fragrances of the invention surprisingly demonstrate effective repellency against cockroaches, particularly German cockroaches (blattella germanica), and more particularly against both German and American cockroaches (blattella germanica and periplaneta americana).
  • insect repellent fragrance as used herein is meant a fragrance comprising the specified fragrance ingredients generally (but not necessarily) having an odour that is considered pleasant or attractive, and which has an insect repellent effect.
  • One convenient procedure by which the insect repellent effect can be tested and measured involves incorporating the insect repellent fragrance into a liquid polish, with 3.0ml of the liquid polish being evenly applied to half the area (i.e.
  • insects which typically crawl e.g. cockroaches such as German cockroaches (blattella germanica) and American cockroaches (periplaneta americana) as well as ants e.g. from the genera lasius flavus, lasius niger and monomorium pharoanis.
  • cockroaches such as German cockroaches (blattella germanica) and American cockroaches (periplaneta americana) as well as ants e.g. from the genera lasius flavus, lasius niger and monomorium pharoanis.
  • fragrances in accordance with the present invention are used to repel cockroaches, particularly German cockroaches and more particularly both German and American cockroaches.
  • the insect repellent fragrance comprises at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate (PtBCHA), preferably at least two, more preferably at least three, and even more preferably at least four of these fragrance ingredients.
  • PtBCHA p-tertiary butyl cyclohexyl acetate
  • insect repellent fragrances as defined herein comprise at least 1 % linalol, at least 2% limonene, at least 2% and preferably greater than 3 % citronellal, at least 2% and preferably greater than 3% terpinolene, and at least 3% p-tertiary butyl cyclohexyl acetate by weight of the insect repellent fragrance.
  • the insect repellent fragrance may optionally be admixed with further excipients such as one or more further fragrance ingredients to obtain an overall pleasing fragrance with effective repellent activity, diluents, fixatives, and a further suitable solvent, or mixtures thereof.
  • excipients which may advantageously be present in the insect repellent fragrances in accordance with the invention are: aldehyde Cl l (undecylenic aldehyde); aldehyde iso Cl l (GIV); allspice oil; allyl cyclohexyl propionate; amyl salicylate; amylcinnamic aldehyde; anethole; anisic alcohol; anisic aldehyde; Applinal (Q) (Applinal is a Trade Mark); bay oil; benzyl acetate; benzyl benzoate; benzyl cinnamate; benzyl propionate; benzyl salicylate; Bourgeonal (Q) (Bourgeonal is a Trade Mark); brahmanol; camphor powder synthetic; cedarwood Virginian; cedrenol; cedryl acetate; Celestolide (IFF) (Celestolide is a Trade Mark); cineole; c
  • the insect repellent fragrance may optionally include other known insect repellents, and preferably known insect repellent fragrance ingredients.
  • Suitable known insect repellents for use herein include N,N-diethyl-rn-toluamide (DEET); N,N- diethylbenzamide; citronella; Tolu balsam; Peru balsam; Eucalyptus oil; Huon pine oil; camphor; cypress oil; galbanum; dibutyl phthalate; dimethyl phthalate; l ,2,3a,4,5,5a,6,7,8,9,9a,9b- dodecahydro- 3a,6,6,9a-tetramethylnaphtho[2,l-b] furan; 4-(tricyclo [5.2.1.0 ⁇ jdecyijdene- o ,) butanal; l-ethoxy-l-(2'-phenylethoxy)ethane; acetyl cedrene; propylidene
  • Insect repellent fragrances in accordance with the invention are preferably incorporated in products for application to a surface e.g. floors, walls, counters, sinks, cupboards, furniture or doors etc..
  • the invention in a further aspect therefore provides a product comprising an insect repellent fragrance in accordance with the invention.
  • Suitable and preferred products include for example, hard surface cleaners, pastes and polishes e.g. furniture polish, floor polish and floor paste in typically liquid or solid e.g. wax form.
  • a particularly preferred product is a floor polish.
  • the products defined herein above comprise between 0.01 % to 20% and more preferably 0.1 % to 10% by weight of the product of an insect repellent fragrance in accordance with the present invention.
  • the invention provides a product comprising an insect repellent fragrance, wherein the product comprises;
  • (c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; and wherein the product comprises at least 0.15% by total weight of the product of (a), (b) and (c).
  • the product will typically comprise further suitable adjuvants appropriate to the nature of the product.
  • suitable adjuvants may include wax e.g. paraffin, carnauba, ceresin wax etc. , resins, plasticizers, water, surfactants e.g. anionic, cationic, nonionic, amphoteric compounds, builders, fluorescent brighteners, antistatic agents, antibacterial agents, fungicides, foaming agents, anti-foams, flow promoters, suspending agents, and anti-gelling agents.
  • Insect repellent fragrances according to the present invention in their simplest form as a fragrance, or as part of a product, may be applied to a surface, including floors, furniture, walls etc. by spraying, for instance as an aerosol or by a pump action, by brushing, by wiping, for instance from an impregnated cloth or with an applicator, pouring etc. on the surface to be treated.
  • the invention provides a method of repelling insects from a surface comprising the step of applying to the surface an effective amount, typically from 0.001 to 1.000g/m 2 , of an insect repellent fragrance, preferably a product comprising from 0.01 % to 20% by weight of the product of an insect repellent fragrance, in accordance with the present invention.
  • the invention provides the use of an insect repellent fragrance in accordance with the present invention for repelling cockroaches, particularly German cockroaches (blattella germanica) and/or American cockroaches (periplaneta americana).
  • cockroaches particularly German cockroaches (blattella germanica) and/or American cockroaches (periplaneta americana).
  • Figure 1 is a schematic representation of the arrangement of a test area used to determine the repellency of a fragrance to insects of interest, the test area being divided into nine equal channels, with half of the total area treated with a fragrance (as shown by the spotted shading) and half untreated.
  • fragrances in accordance with the present invention particularly to German cockroaches (blattella germanica) and American cockroaches (periplaneta americana), was demonstrated as described below.
  • fragrances not in accordance with the present invention were also prepared and tested using the same protocol.
  • fragrances prepared were then incorporated into a self-shining liquid floor polish i.e. a floor polish which dries with a shiny finish and does not typically require buffing, the formulation of which is indicated below:
  • Each self-shining liquid floor polish comprising one of fragrances 1 to 7 was tested for its ability to repel German cockroaches (blattella germanica) and American cockroaches (periplaneta americana) according to the following protocol.
  • the test surface was vinyl flooring of 600mm x 600mm total area which was divided into an arena of nine equally sized channels each of 30mm x 600mm, as illustrated in Figure 1. 3.0ml of a polish was applied by syringe to the test surface and the polish distributed evenly with an applicator such that half of the total test surface area (300mm x 600mm) was treated with the polish, as represented by the spotted area in Figure 1, and half the total test surface area was untreated. The polish was left to dry for approximately one hour. Five cockroaches, periplaneta americana or blattella germanica, of mixed age and gender were placed in each channel and their behaviour monitored by video recorder.
  • the video recording commenced 10 minutes after introduction of the cockroaches to the channels and was stopped after 1 hour of recording. The cockroaches were then removed. After 24 hours, five cockroaches were returned to each of the channels and the recording process repeated. The video recording was played back and stopped at five minute intervals over an hour to obtain twelve readings. At each five minute interval, the number of cockroaches on the treated area was counted.
  • the repellency for the nine channels was calculated as follows:
  • Repellency (%) (270-N)/270 x 100
  • results are as indicated in the table below with the number representing the percentage of cockroaches of a particular species repelled from the treated area.

Landscapes

  • 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

The present invention provides an insect repellent fragrance comprising; (a) at least 10% by weight of the insect repellent fragrance of geraniol; (b) at least 10% by weight of the insect repellent fragrance of diethyl phthalate; and (c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; wherein the insect repellent fragrance comprises at least 60% by total weight of the insect repellent fragrance of (a), (b) and (c). The insect repellent fragrance surprisingly demonstrates effective repellency, particularly against cockroaches, and more particularly against both German and American cockroaches.

Description

Insect Repellents
Field of the Invention
The present invention relates to fragrances, particularly insect repellent fragrances, to products comprising such fragrances and to a method of repelling insects.
Background of the Invention
Insects have long been known to be a nuisance to humans, and for some insect genera, a health hazard.
Many common types of household insects such as cockroaches, e.g. American cockroaches (periplaneta americana) and German cockroaches (blattella germanica), are classified as pests and significant effort has been made to control or eradicate them. A variety of chemical compounds have been discovered, e.g. N,N-diethyl-meta-toluamide, which are efficacious in repelling cockroaches. Such chemical compounds are used in the household by applying or spraying them to surfaces of walls, floors, cabinets, containers, rugs, upholstery and carpeting, and in potential nesting places for these insects, such as inside walls and between floors. Chemical compounds have been used together with hard surface cleaners (EP-A-0619363) and wax floor polishes (US-A-3018217).
It is known in the art that essential oils and synthetic fragrance ingredients (also known as perfume materials) can repel insects. Further, use of these ingredients may be advantageous compared with the use of chemical compounds in terms of presenting lower toxicity to mammals. WO 96/08147 describes an insect repellent composition comprising at least one active ingredient from the group of compounds consisting of: 1,2, 3a, 4, 5, 5a, 6, 7, 8, 9, 9a, 9b- dodecahydro-3a,6,6,9a-tetramethylnaphtho [2, 1-b] furan (AMBERLYN™); 4-(tricyclo [5.2.1.02 6] decylidene-8) butanal (DUPICAL™); l-ethoxy-l-(2'-phenylethoxy) ethane (EFETAAL™); acetyl cedrene (LIXITONE™); and propylidene phthalide. The compositions are described as preferably used to repel biting insects, such as mosquitoes, and in particular members of the genus Aedes.
Perfume materials, or fragrances, with repellent properties to either American cockroaches (periplaneta ameήcana) e.g. as disclosed in WO 00/19822 and Ngoh S.P. et al. , Pestic. Sci. , 1998, 54, p261, or German cockroaches (blattella germanica) e.g. as disclosed in JP 2207004, are known. However, typically, it is difficult to formulate a complete fragrance which effectively repels cockroaches, particularly German cockroaches, and more particularly, repels both German and American cockroaches, possibly together with other crawling insects e.g. ants.
Summary of the Invention
In one aspect, the present invention provides an insect repellent fragrance comprising;
(a) at least 10% by weight of the insect repellent fragrance of geraniol;
(b) at least 10% by weight of the insect repellent fragrance of diethyl phthalate; and
(c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; wherein the insect repellent fragrance comprises at least 60% by total weight of the insect repellent fragrance of (a), (b) and (c).
The present invention is based on the appreciation that insect repellent fragrances of the invention surprisingly demonstrate effective repellency against cockroaches, particularly German cockroaches (blattella germanica), and more particularly against both German and American cockroaches (blattella germanica and periplaneta americana).
By "insect repellent fragrance" as used herein is meant a fragrance comprising the specified fragrance ingredients generally (but not necessarily) having an odour that is considered pleasant or attractive, and which has an insect repellent effect. One convenient procedure by which the insect repellent effect can be tested and measured involves incorporating the insect repellent fragrance into a liquid polish, with 3.0ml of the liquid polish being evenly applied to half the area (i.e. 300mm x 600mm) of a vinyl flooring test surface of total area 600mm x 600mm, which is then divided into nine channels (30mm x 600mm) so that half of each channel (30mm x 600mm) is treated and half is untreated, the liquid polish being allowed to dry for approximately one hour before at least five insects are introduced into each channel and allowed to acclimatise to the conditions for about ten minutes, after which, i.e. at t = 0 hours, the movements of the insects are measured by video recorder. An insect repellent fragrance initially, i.e. at t = 1 hour, preferably repels from the treated area at least 60% , more preferably at least 65%, most preferably at least 70%, of the insects.
The term "insect" as used herein is intended to encompass insects which typically crawl e.g. cockroaches such as German cockroaches (blattella germanica) and American cockroaches (periplaneta americana) as well as ants e.g. from the genera lasius flavus, lasius niger and monomorium pharoanis. Preferably, fragrances in accordance with the present invention are used to repel cockroaches, particularly German cockroaches and more particularly both German and American cockroaches.
Typically, the insect repellent fragrance comprises at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate (PtBCHA), preferably at least two, more preferably at least three, and even more preferably at least four of these fragrance ingredients. Conveniently, when present, insect repellent fragrances as defined herein comprise at least 1 % linalol, at least 2% limonene, at least 2% and preferably greater than 3 % citronellal, at least 2% and preferably greater than 3% terpinolene, and at least 3% p-tertiary butyl cyclohexyl acetate by weight of the insect repellent fragrance.
The insect repellent fragrance may optionally be admixed with further excipients such as one or more further fragrance ingredients to obtain an overall pleasing fragrance with effective repellent activity, diluents, fixatives, and a further suitable solvent, or mixtures thereof.
Other excipients which may advantageously be present in the insect repellent fragrances in accordance with the invention are: aldehyde Cl l (undecylenic aldehyde); aldehyde iso Cl l (GIV); allspice oil; allyl cyclohexyl propionate; amyl salicylate; amylcinnamic aldehyde; anethole; anisic alcohol; anisic aldehyde; Applinal (Q) (Applinal is a Trade Mark); bay oil; benzyl acetate; benzyl benzoate; benzyl cinnamate; benzyl propionate; benzyl salicylate; Bourgeonal (Q) (Bourgeonal is a Trade Mark); brahmanol; camphor powder synthetic; cedarwood Virginian; cedrenol; cedryl acetate; Celestolide (IFF) (Celestolide is a Trade Mark); cineole; cinnamic alcohol; cinnamic aldehyde; cinnamon leaf oil; cinnamyl acetate; cis-3- hexenol; citral; citronella oil; citronellol; citronellyl acetate; citronellyl oxyacetaldehyde; clove oil; coriander oil; coumarin; cuminic aldehyde; cyclamen aldehyde; decanal; 9-decenol; dibenzyl ether; dibutyl phthalate; dihydromyrcenol; dimethyl anthranilate; dimethyl phthalate; Dimycretol (IFF) (Dimycretol is a Trade Mark); diphenyl methane; diphenyl oxide; dimethyl benzyl carbinyl acetate; dodecanol; dodecanal; elemi oil; ethyl methyl phenyl glycidate; ethyl cinnamate; Ethyl Safranate (Q) (Ethyl Safranate is a Trade Mark); ethyl vanillin; eugenol; evergreen oils (pine oils etc.); gamma-nonalactone; gamma-undecalactone; geranium bourbon; geranyl acetate; geranyl formate; gum benzoin; heliotropin; Hercolyn D (HER) (Hercolyn D is a Trade Mark); hexyl benzoate; hexylcinnamic aldehyde; hexyl salicylate; hydratropic aldehyde dimethyl acetal; hydroxy citronellal; hydroxycitronellal dimethyl acetal; indole; iso bornyl acetate; isopropyl myristate; iso-cyclocitral (GIV, IFF); jasmacyclene; jasmin oil; lavandin abrialis; lavender oil; Lilial (GIV) (Lilial is a Trade Mark); linalyl acetate; menthol laevo; methyl anthranilate; methyl cedryl ketone; methyl dihydrojasmonate; methyl ionone; methyl myristate; methyl naphthyl ketone; methyl salicylate; moss treemoss; musk ketone; nerol; nerolin bromelia; neryl acetate; nonanal; oakmoss absolute; octanal olibanum resinoid; para-cresyl phenylacetate; para-methoxyacetophenone; patchouli oil; peppermint oil; petitgrain oil; 2-phenoxyethanol; phenoxy ethyl iso butyrate; phenylethylacetate; phenyethyl alcohol; phenylethyl butyrate; phenylethyl phenylacetate; pimento oil; pinene, alpha; resinoid benzoin siam; rose oil; rosemary oil; sandalwood oil; terpineol; tetrahydrolinalol; Tetrahydromuguol (IFF); thyme red; undecanal; vanillin; verbena oil; vetyvert bourbon; yara and ylang ylang.
Compounds are obtainable from the suppliers as indicated below: for those compounds labelled "(Q)", - Quest International; "(IFF)" - International Flavours & Fragrances, Inc. ; "(GIV)" - Givaudan; "(HER)" - Hercules B.V.
The insect repellent fragrance may optionally include other known insect repellents, and preferably known insect repellent fragrance ingredients. Suitable known insect repellents for use herein include N,N-diethyl-rn-toluamide (DEET); N,N- diethylbenzamide; citronella; Tolu balsam; Peru balsam; Eucalyptus oil; Huon pine oil; camphor; cypress oil; galbanum; dibutyl phthalate; dimethyl phthalate; l ,2,3a,4,5,5a,6,7,8,9,9a,9b- dodecahydro- 3a,6,6,9a-tetramethylnaphtho[2,l-b] furan; 4-(tricyclo [5.2.1.0 ^όjdecyijdene-o,) butanal; l-ethoxy-l-(2'-phenylethoxy)ethane; acetyl cedrene; propylidene phthalide; citral diethyl acetal available under the trade mark "CITRATHAL"; tricyclodecenyl allyl ether available under the trade mark "FLEUROXENE"; 2-(2-methylpropyl)-4-hydroxy-4- mefhyltetrahydropyran available under the trade mark "FLOROSA"; N-methyl-N-phenyl-2- methylbutanamide available under the trade mark "GARDAMIDE", 4-isobutyrate-3- methoxybenzaldehyde available under the trade mark "ISOBUTAVAN"; l-hydroxy-2- mefhoxy-4-propenyl benzene; 2,2,7,7-tetramethyltricyclo[6.2.1.0 l>6]undecan-5-one available under the trade mark "ISOLONGIFOLANONE"; 7-formyl-5-isopropyl-2- methylbicyclo(2.2.2)oct-2-ene available under the trade mark "MACEAL"; 3-methyl-5- phenylpentanal available under the trade mark "MEFRANAL"; alpha iso methyl ionone; myrcenyl acetate available under the trade mark "NEOBERGAMATE; 10-isopropyl-2,7- dimethyloxaspiro [4.5] 3,6-decadiene available under the trade mark "NEOCASPIRENE" ; tricyclo[5.2.1.0 2,6]cjec_4_en_8-yl 2,2-dimethylpropanoate available under the trade mark "PIVACYCLENE" ; 2-phenylethyl pivalate available under the trade mark "PIVAROSE" and 2,4-dimethyl-4-phenyltetrahydrofuran available under the trade mark "RHUBAFURAN" .
Insect repellent fragrances in accordance with the invention are preferably incorporated in products for application to a surface e.g. floors, walls, counters, sinks, cupboards, furniture or doors etc.. The invention in a further aspect therefore provides a product comprising an insect repellent fragrance in accordance with the invention.
Suitable and preferred products include for example, hard surface cleaners, pastes and polishes e.g. furniture polish, floor polish and floor paste in typically liquid or solid e.g. wax form. A particularly preferred product is a floor polish.
Preferably, the products defined herein above comprise between 0.01 % to 20% and more preferably 0.1 % to 10% by weight of the product of an insect repellent fragrance in accordance with the present invention. In an even further aspect, the invention provides a product comprising an insect repellent fragrance, wherein the product comprises;
(a) at least 0.025% by weight of the product of geraniol;
(b) at least 0.025% by weight of the product of diethyl phthalate; and
(c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; and wherein the product comprises at least 0.15% by total weight of the product of (a), (b) and (c).
The product will typically comprise further suitable adjuvants appropriate to the nature of the product. Suitable adjuvants may include wax e.g. paraffin, carnauba, ceresin wax etc. , resins, plasticizers, water, surfactants e.g. anionic, cationic, nonionic, amphoteric compounds, builders, fluorescent brighteners, antistatic agents, antibacterial agents, fungicides, foaming agents, anti-foams, flow promoters, suspending agents, and anti-gelling agents.
Insect repellent fragrances according to the present invention in their simplest form as a fragrance, or as part of a product, may be applied to a surface, including floors, furniture, walls etc. by spraying, for instance as an aerosol or by a pump action, by brushing, by wiping, for instance from an impregnated cloth or with an applicator, pouring etc. on the surface to be treated.
Thus, in an even further aspect, the invention provides a method of repelling insects from a surface comprising the step of applying to the surface an effective amount, typically from 0.001 to 1.000g/m2, of an insect repellent fragrance, preferably a product comprising from 0.01 % to 20% by weight of the product of an insect repellent fragrance, in accordance with the present invention.
In an even further aspect the invention provides the use of an insect repellent fragrance in accordance with the present invention for repelling cockroaches, particularly German cockroaches (blattella germanica) and/or American cockroaches (periplaneta americana). The invention is illustrated by way of the following non-limiting examples, and with reference to the accompanying drawing, in which:
Figure 1 is a schematic representation of the arrangement of a test area used to determine the repellency of a fragrance to insects of interest, the test area being divided into nine equal channels, with half of the total area treated with a fragrance (as shown by the spotted shading) and half untreated.
Examples
The repellency of fragrances in accordance with the present invention, particularly to German cockroaches (blattella germanica) and American cockroaches (periplaneta americana), was demonstrated as described below. For comparison, fragrances not in accordance with the present invention were also prepared and tested using the same protocol.
Fragrances 1 to 4 in accordance with the present invention, and comparative fragrances 5 to 7, were prepared in the proportions indicated in the table below. All percentages are by weight.
Figure imgf000008_0001
Figure imgf000009_0001
The fragrances prepared were then incorporated into a self-shining liquid floor polish i.e. a floor polish which dries with a shiny finish and does not typically require buffing, the formulation of which is indicated below:
Figure imgf000009_0002
LICOMER, BRONIDOX and LUTENSOL are all trade marks.
Each self-shining liquid floor polish comprising one of fragrances 1 to 7 was tested for its ability to repel German cockroaches (blattella germanica) and American cockroaches (periplaneta americana) according to the following protocol.
Each fragrance was tested against each species of cockroach, with one species of cockroach used per test.
The test surface was vinyl flooring of 600mm x 600mm total area which was divided into an arena of nine equally sized channels each of 30mm x 600mm, as illustrated in Figure 1. 3.0ml of a polish was applied by syringe to the test surface and the polish distributed evenly with an applicator such that half of the total test surface area (300mm x 600mm) was treated with the polish, as represented by the spotted area in Figure 1, and half the total test surface area was untreated. The polish was left to dry for approximately one hour. Five cockroaches, periplaneta americana or blattella germanica, of mixed age and gender were placed in each channel and their behaviour monitored by video recorder. The video recording commenced 10 minutes after introduction of the cockroaches to the channels and was stopped after 1 hour of recording. The cockroaches were then removed. After 24 hours, five cockroaches were returned to each of the channels and the recording process repeated. The video recording was played back and stopped at five minute intervals over an hour to obtain twelve readings. At each five minute interval, the number of cockroaches on the treated area was counted. The repellency for the nine channels was calculated as follows:
Total number of cockroach observations possible = 540 (12 times, 9 channels, 5 insects per channel)
Total number of cockroach observations on treated area if no effect = 540/2 = 270
Total number of cockroaches observed on treated area = N (total of 12 times for 9 channels)
Therefore, Repellency (%) = (270-N)/270 x 100
The results are as indicated in the table below with the number representing the percentage of cockroaches of a particular species repelled from the treated area.
Figure imgf000010_0001
Figure imgf000011_0001
The results show that only Fragrances 1, 2, 3 and 4 repel at least 60% of both species of cockroach (i.e. periplaneta americana and blattella germanica) initially. Whilst comparative fragrances 5 and 6 demonstrate effective repellency to cockroaches of the species periplaneta americana, they demonstrate poorer repellency to the blattella germanica species. Comparative fragrance 7 does not demonstrate effective repellency against either species of cockroach after 24 hours.

Claims

1. An insect repellent fragrance comprising;
(a) at least 10% by weight of the insect repellent fragrance of geraniol;
(b) at least 10% by weight of the insect repellent fragrance of diethyl phthalate; and
(c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; wherein the insect repellent fragrance comprises at least 60% by total weight of the insect repellent fragrance of (a), (b) and (c).
2. An insect repellent fragrance according to claim 1 , wherein the fragrance comprises at least two of linalol, limonene, citronellal, terpinolene, and p-tertiary butyl cyclohexyl acetate.
3. An insect repellent fragrance according to claim 1 or 2, wherein the fragrance comprises at least three of linalol, limonene, citronellal, terpinolene, and p-tertiary butyl cyclohexyl acetate.
4. An insect repellent fragrance according to any one of the preceding claims, wherein the fragrance comprises at least 1 % by weight of the insect repellent fragrance of linalol.
5. An insect repellent fragrance according to any one of the preceding claims, wherein the fragrance comprises at least 2% by weight of the insect repellent fragrance of limonene.
6. An insect repellent fragrance according to any one of the preceding claims, wherein the fragrance comprises at least 2% by weight of the insect repellent fragrance of citronellal.
7. An insect repellent fragrance according to any one of the preceding claims, wherein the fragrance comprises at least 2% by weight of the insect repellent fragrance of terpinolene.
8. An insect repellent fragrance according to any one of the preceding claims, wherein the fragrance comprises at least 3 % by weight of the insect repellent fragrance of p-tertiary butyl cyclohexyl acetate.
9. A product comprising an insect repellent fragrance in accordance with any one of the preceding claims.
10. A product comprising an insect repellent fragrance, wherein the product comprises;
(a) at least 0.025 % by weight of the product of geraniol;
(b) at least 0.025 % by weight of the product of diethyl phthalate; and
(c) at least one or more of linalol, limonene, citronellal, terpinolene and p-tertiary butyl cyclohexyl acetate; and wherein the product comprises at least 0.15% by total weight of the product of (a), (b) and (c).
11. A product according to claim 9 or 10, wherein the product is a hard surface cleaner, polish or paste, particularly a floor polish.
12. A method of repelling insects from a surface comprising the step of applying to the surface an effective amount of an insect repellent fragrance in accordance with any one of claims 1 to 8.
13. Use of an insect repellent fragrance in accordance with any one of claims 1 to 8 for repelling cockroaches, particularly German cockroaches (blattella germanica) and/or American cockroaches (periplaneta americana).
PCT/GB2002/003369 2001-08-11 2002-07-23 Insect repellents Ceased WO2003013243A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AT02749049T ATE307482T1 (en) 2001-08-11 2002-07-23 INSECT REPELLENT
BR0211177-2A BR0211177A (en) 2001-08-11 2002-07-23 Insect repellent fragrance, product, method for repelling insects from a surface, and use of an insect repellent fragrance
EP02749049A EP1414298B1 (en) 2001-08-11 2002-07-23 Insect repellents
DE60206929T DE60206929T2 (en) 2001-08-11 2002-07-23 INSECT REPELLENT
US10/486,423 US7455852B2 (en) 2001-08-11 2002-07-23 Insect repellents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0119660.9A GB0119660D0 (en) 2001-08-11 2001-08-11 Insect repellents
GB0119660.9 2001-08-11

Publications (1)

Publication Number Publication Date
WO2003013243A1 true WO2003013243A1 (en) 2003-02-20

Family

ID=9920256

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2002/003369 Ceased WO2003013243A1 (en) 2001-08-11 2002-07-23 Insect repellents

Country Status (10)

Country Link
US (1) US7455852B2 (en)
EP (1) EP1414298B1 (en)
CN (1) CN1310583C (en)
AT (1) ATE307482T1 (en)
BR (1) BR0211177A (en)
DE (1) DE60206929T2 (en)
ES (1) ES2249601T3 (en)
GB (1) GB0119660D0 (en)
WO (1) WO2003013243A1 (en)
ZA (1) ZA200400169B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1745772A3 (en) * 2005-07-20 2007-07-25 Beiersdorf AG Insect repellents with improved activity
EP2568814A4 (en) * 2010-05-14 2013-12-04 James J Messina Broad spectrum pest repellent compositions and pest management system
WO2015116306A1 (en) 2014-01-28 2015-08-06 Avon Products, Inc. Extended release fragrance compositions
US9271486B2 (en) 2011-11-10 2016-03-01 James J. Messina Combination animal repellents
US9693566B2 (en) 2008-08-13 2017-07-04 James Messina, Sr. Broad spectrum animal repellent and method

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0410491A8 (en) 2003-04-24 2017-10-24 Univ Vanderbilt COMPOSITIONS AND METHODS FOR INSECT CONTROL
US7622269B2 (en) 2004-03-19 2009-11-24 Tyratech, Inc. Methods of screening tyramine- and octopamine-expressing cells for compounds and compositions having potential insect control activity
US20080145462A1 (en) 2006-06-27 2008-06-19 Essam Enan Compositions and methods for treating parasitic infections
JP2009543870A (en) 2006-07-17 2009-12-10 タイラテック， インク． Compositions and methods for insect control
DE102007026049A1 (en) * 2007-05-31 2008-12-04 Beiersdorf Ag Repellents against wasps
US9924718B2 (en) * 2013-04-30 2018-03-27 Bedoukian Research, Inc. Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs
US20160029616A1 (en) * 2014-08-01 2016-02-04 Brandon Johnston Pest deterrent barrier
CN105613529A (en) * 2016-02-16 2016-06-01 烟台米罗卡化工科技有限公司 Insecticide for aedes albopictus
EP3503725A4 (en) * 2016-08-23 2020-05-13 Kittrich Corporation COMPOUNDS CONTAINING A MONOTERPENOID / PHENYLPROPANOID AND PROCESSES FOR THEIR PRODUCTION AND USE AS INSECTICIDE Baits
ES2674263B1 (en) * 2016-12-28 2019-04-02 Zobele Espana Sa Insect repellent product
CN107638313A (en) * 2017-09-04 2018-01-30 上海千紫香料有限公司 A kind of mosquito-repellent essential oil and preparation method thereof
CN108552212A (en) * 2018-06-05 2018-09-21 蚌埠市刘兴桃种植农民专业合作社 A kind of solid repellent and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5386021A (en) * 1976-12-10 1978-07-29 Ajinomoto Co Inc Cockroach repellent
JPH0267202A (en) * 1988-09-01 1990-03-07 Takara Kosan Kk Mothproofing molded product
EP0619363A1 (en) * 1993-04-08 1994-10-12 Colgate-Palmolive Company Liquid household cleaning composition with insect repellent
WO2000027197A1 (en) * 1998-11-10 2000-05-18 The Procter & Gamble Company A composition containing an insect repellent active blend

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5227163A (en) * 1991-01-18 1993-07-13 Clilco, Ltd. Lice-repellant compositions
US6001874A (en) * 1992-08-18 1999-12-14 Veierov; Dan Arthropod control composition for plant protection
US5439690A (en) * 1993-05-21 1995-08-08 Ecosmart, Inc. Non-hazardous pest control
WO2001060163A2 (en) * 2000-02-17 2001-08-23 Ecosmart Technologies, Inc. Plant essential oils cointaining pediculicidal compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5386021A (en) * 1976-12-10 1978-07-29 Ajinomoto Co Inc Cockroach repellent
JPH0267202A (en) * 1988-09-01 1990-03-07 Takara Kosan Kk Mothproofing molded product
EP0619363A1 (en) * 1993-04-08 1994-10-12 Colgate-Palmolive Company Liquid household cleaning composition with insect repellent
WO2000027197A1 (en) * 1998-11-10 2000-05-18 The Procter & Gamble Company A composition containing an insect repellent active blend

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
AM. LAB. (FAIRFIELD, CONN.) (1981), 13(10), 64, 66-9 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; INAZUKA, SHINICHI ET AL: "Monoterpenoids as cockroach repellent", XP002212226, retrieved from STN Database accession no. 90:17693 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; VERMA, M. ET AL: "A natural cockroach repellent in bay leaves", XP002212227, retrieved from STN Database accession no. 95:199004 *
DATABASE WPI Derwent World Patents Index; AN 1990-118678, XP002212228, IWASE COSFA: "Insect repellent resin mouldings -contains inorganic porous microcapsules enclosing repellent core" *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1745772A3 (en) * 2005-07-20 2007-07-25 Beiersdorf AG Insect repellents with improved activity
EP2119432A3 (en) * 2005-07-20 2010-03-17 Beiesrdorf Ag Insect repellents with improved activity
US9693566B2 (en) 2008-08-13 2017-07-04 James Messina, Sr. Broad spectrum animal repellent and method
EP2568814A4 (en) * 2010-05-14 2013-12-04 James J Messina Broad spectrum pest repellent compositions and pest management system
US9271486B2 (en) 2011-11-10 2016-03-01 James J. Messina Combination animal repellents
US9414603B2 (en) 2011-11-10 2016-08-16 James J. Messina Combination animal repellents
US9572348B2 (en) 2011-11-10 2017-02-21 James J. Messina Combination animal repellents
WO2015116306A1 (en) 2014-01-28 2015-08-06 Avon Products, Inc. Extended release fragrance compositions

Also Published As

Publication number Publication date
DE60206929D1 (en) 2005-12-01
EP1414298B1 (en) 2005-10-26
GB0119660D0 (en) 2001-10-03
ATE307482T1 (en) 2005-11-15
BR0211177A (en) 2004-08-10
EP1414298A1 (en) 2004-05-06
US7455852B2 (en) 2008-11-25
ES2249601T3 (en) 2006-04-01
US20040213822A1 (en) 2004-10-28
CN1310583C (en) 2007-04-18
CN1541062A (en) 2004-10-27
DE60206929T2 (en) 2006-07-27
ZA200400169B (en) 2005-03-29

Similar Documents

Publication Publication Date Title
EP1414298B1 (en) Insect repellents
US4933371A (en) Controlling ticks and fleas with linalool
JP5485337B2 (en) Composition having insect repellent properties
EP1119250B1 (en) Insect repellents
CN113905612B (en) Arthropod control composition
US20120171313A1 (en) Compositions and Methods for Applying and Manufacturing Biopesticides
CN101626689A (en) Pest repellent
EP1283673A2 (en) Soap based pesticides
CN113873884B (en) Arthropod control composition
WO1996028032A1 (en) Disinfectant/insecticide composition containing eucalyptus oil and australian tea tree oil
CZ82994A3 (en) Aqueous liquid detergent with repellent effect and process of cleaning solid surfaces
EP0934392B1 (en) Use of detergents comprising 3-(N-butylacetamino)-propionic ethyl ester as insect repellant agent.
JP2025535405A (en) Arthropod control composition
GB2163651A (en) Linalool pesticide
US20240057595A1 (en) Insect repellent compositions
CN115867139A (en) Arthropod control composition
EP4426116A1 (en) Arthropod control compositions
US20250113823A1 (en) Arthropod Control Compositions
WO2023199025A1 (en) Pest control composition and method of repelling insects
JP2025504445A (en) Arthropod control composition
JP2025504445A5 (en)
CN118450801A (en) Arthropod control composition
AU2007200923A1 (en) Composition Having Insect Repellent Characteristics

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VN YU ZA ZM

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG US

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2004/00169

Country of ref document: ZA

Ref document number: 200400169

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 2002749049

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 10486423

Country of ref document: US

Ref document number: 20028156943

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 1200400113

Country of ref document: VN

WWP Wipo information: published in national office

Ref document number: 2002749049

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 2002749049

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Ref document number: JP