WO2005013694A1 - Allomones insectifuges - Google Patents

Allomones insectifuges Download PDF

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Publication number
WO2005013694A1
WO2005013694A1 PCT/EP2004/009167 EP2004009167W WO2005013694A1 WO 2005013694 A1 WO2005013694 A1 WO 2005013694A1 EP 2004009167 W EP2004009167 W EP 2004009167W WO 2005013694 A1 WO2005013694 A1 WO 2005013694A1
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Prior art keywords
allomone
composition
cyclohexane
propanoic acid
cyclopentane
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PCT/EP2004/009167
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English (en)
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WO2005013694B1 (fr
Inventor
Patrick Pageat
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Fideline
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Publication of WO2005013694B1 publication Critical patent/WO2005013694B1/fr

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    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives 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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/10—Animals; Substances produced thereby or obtained therefrom

Definitions

  • the present invention relates to a composition comprising an- allomone that can be used to repel insects. More specifically the present invention relates to a composition comprising cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid. The present invention also relates to methods to repulse insects in various environments, such as around outdoor tables, which may contain food, around pools, around flower beds, as well as beach environments, using the composition of the present invention. BACKGROUND AND PRIOR ART Insect repellent compositions have been around for many years and generally are made up of specific chemicals or mixtures thereof. For instance, in German Patent No.
  • 2 036 880 describes the use of a nitrophenylcarbonic acid to combat mollusks and water inhabiting microorganisms. Also the use of naphthalene as a moth repellant and insecticide was known, but the use is decreasing due to the introduction of chlorinated compounds such as p-dichlorobenzene into the atmosphere. However, there is still a need in this art to formulate an insect repellant that is natural, safe, easy to use and repels, not only known insect pests such as ants and mosquitoes, but other insect pests as well. The secretions produced by different glands that can intervene in a chemical communication are known as chemical signals.
  • pheromones are substances released by the body that cause a predictable reaction by another individual of the same species, which substance may serve, for example, as a specific attractant, social communicator, sexual stimulant and the like.
  • a number of different glands are known to produce pheromones in male mammals such as the submaxillary salivary glands, the parathyroid glands and the sebaceous glands.
  • pheromones are described, for example, in U.S. Patent Nos.
  • allelochemical signals are generally divided into two subgroups and their function affects the relationship between the emitter of the signal and the receiver of the message.
  • the subgrouping is known as an allomone.
  • an allomone is a hormone or substance produced by one species that has an effect upon another species, especially so as to benefit the emitting species. For example, the attractive allomones emitted by certain flowers can attract various insects that can pollinate these flowers.
  • a kairomone is a pheromone or substance that can attract other species and sometimes even natural enemies.
  • the kairomones are notably implicated in locating a particular host by a parasite.
  • lactic acid that is emitted by the human skin is a kairomone known for a number of Culicidae. It is known that certain mammals of the family Mustelidae or the family Ursidae are fond of larvae from the order of Hymenoptera and of honey.
  • the present invention provides an allomone composition that repels insects which is isolated from secretions obtained from a mammal.
  • the present invention provides an allomone composition comprising one or more of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid, derivatives thereof and isomers thereof as well as mixtures of one or more of the above cyclic compounds with one or more derivative and/or one or more isomer; in an acceptable delivery vehicle.
  • It is another yet aspect of the present invention to provide an allomone composition that comprises at least two of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid.
  • cyclopentane propanoic acid cyclohexane acetic acid
  • cyclohexane propanoic acid cyclohexane propanoic acid
  • cyclopentane propanoic acid Mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more derivatives and/or one or more isomers of cyclopentane propanoic acid, cyclohexane acidic acid and cyclohexane propanoic acid are also encompassed by the present invention. It is another aspect of the present invention to provide a method for repelling insects, said method comprising placing in the environment a composition comprising an allomone composition derived from the jugale secretions of a badger.
  • the present invention provides an allomone composition
  • an allomone composition comprising one or more of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid or derivatives thereof or isomers thereof, as well as mixtures of one or more of the above cyclic compounds with one or more derivative and/or one or more isomer; in an acceptable delivery vehicle.
  • compositions that comprises at least two of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid or derivatives thereof or isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more derivatives and/or one or more isomers of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid, which composition repels insects.
  • the present invention provides a method for repelling insects, said method comprising placing in the environment a composition comprising an allomone composition derived from the jugale secretions of a badger. It is yet another aspect of the present invention to provide a method for repelling insects, said method comprising placing in the environment a composition that comprises one or more of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid or derivatives thereof or isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more derivatives and/or one or more isomers of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid.
  • Fig. 1 is a schematic representation of a box used in the insect experiments.
  • Fig. 2 is a mass spectroscopy chromatograph of secretions around the zygomatic bone of badgers (Meles meles L.).
  • Fig. 3 is a chromatograph identifying three major components from secretions around the zygomatic bone of badgers (Meles meles L.).
  • Fig. 4 is a chromatograph identifying three major components from secretions around the zygomatic bone of badgers (Meles meles L.).
  • Fig. 5 is a schematic representation of an apparatus using for testing the order Hymenoptera.
  • Fig. 1 is a schematic representation of a box used in the insect experiments.
  • Fig. 2 is a mass spectroscopy chromatograph of secretions around the zygomatic bone of badgers (Meles meles L.).
  • Fig. 3 is a chromatograph identifying three major components from secretions around the zygomatic bone of badger
  • Fig. 6 are graphs and tables illustrating the statistical analysis of the screening of Diptera Nematocera.
  • Fig. 7 are graphs and tables illustrating the statistical analysis of the screening of Diptera Nematocera.
  • Fig. 8 are graphs and tables illustrating the statistical analysis of the screening of Diptera Nematocera.
  • Fig. 9 is a schematic representation of an experiment used for applying the insect repulsive allomone around a pool.
  • allomone means a hormone or chemical substance produced by one species that has an effect upon another species, especially so as to benefit the emitting species.
  • repel means to drive back and/ or to keep away.
  • the insects when they are repelled they are driven back, for example, from about 1.5 meters to about 10 meters.
  • the distance in which the insects are repelled depends upon the concentration of the allomone composition that is used, as well as the form in which the allomone is delivered. For example, when the allomone composition is used in a diffuser, it has been observed that the insects are repelled from a distance of about 5 meters to about 10 meters. When the allomone composition is placed in a candle or a less concentrated spray, it has been observed that the insects are repelled at a distance of about 1.5 meters to about 2 meters.
  • insects includes all insects in the Class INSECTA under the phylum Arthropoda and includes, but is not limited to, the orders Collembola, Protura, Diplura, Thysanura, Ephimerida, Odonata, Orthoptera, Dermaptera, Embiara, Pformicidae, Fulgoromorpha, lchneumonidae, Isopetra, Lectoptera, Trichoptera, Zoraptera, Corrondentia, Mallophaga, Anoplura, Thysanoptera, Hemiptera, Neuroptera, Coleoptera, Hymenpotera, Mecoptera, Siponaptera, Diptera, Trichoptera and Lepidoptera.
  • the term "encapsulated” means to enclose or become enclosed in. This definition does not mean that the allomone being encapsulated is 100% encapsulated; the amount of encapsulation may range from 5% to 95%.
  • the term “environment” means surroundings. These surroundings are generally in the vicinity of about 1.5 to about 10 meters. By “about” is meant ⁇ 0.1 % (w%).
  • enhancer composition is meant an active composition that is species-specific in insects and which can be used to enhance or act synergistically with the allomone composition to increase the effectiveness in specific species of the composition.
  • the composition can include, for example only, cyclohexane acetic acid and an alcohol derivative of cyclohexane propanoic acid and an isomer of an amide derivative of cyclopentane propanoic acid.
  • the derivatives and isomers referred to herein have the exact same weight percentages as referred to by their chemical counterparts.
  • the derivatives and isomers of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid all have the concentration which ranges from about 5% to about 35% (w%/w%) cyclopentane propanoic acid or between about 25% to about 60% (w%/w%) cyclohexane acetic acid or between about 28% to about 65% (w%/w%) cyclohexane propanoic acid.
  • the term "acceptable delivery vehicle” means that the allomone composition can be formulated in any kind of material such as liposomes, gels, creams, aerosols, towelettes, sprays and solvents.
  • the allomone composition can also be encapsulated, placed in a diffuser or in a slow release matrix, or can be placed in molded or extruded polymers, which can be used to make collars or blocks, impregnated in resins or candles.
  • the allomone composition can also be formulated in insect repellant wrist bands, in tablecloths, tissue and clothes. Any type of pleasing scent can be added to the formulations disclosed herein . such as lavender, cedar, rose, lemon and the like.
  • plaque in the environment means placing the allomone composition in surroundings in which the insects may be present.
  • the term "mammal” encompasses any group of vertebrates the females of which have milk-secreting glands, including man. Examples of mammals include, but are not limited to cats, humans, dogs, pigs, rats, cattle, horses, apes, chimpanzees and the like. More specifically, the present invention provides a composition that repels insects which contains an allomone that was derived from secretions around the jugale area of a badger. The present invention, however, is not limited to obtaining allomones from only badgers.
  • compositions of the present invention comprise allomones that are cyclic acid compounds and are used as an insect repellant in various formulations. More specifically, the compositions of the present invention comprise cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid. These three compounds were identified, as illustrated in the following examples, from the secretions of badgers obtained from the jugale area.
  • the present invention provides an allomone composition
  • an allomone composition comprising one or more of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid, derivatives thereof or isomers thereof as well as mixtures of one or more of the above cyclic compounds with one or more derivative and/or one or more isomer; in an acceptable delivery vehicle.
  • the compositions of the present invention also comprise at least two of the following cyclic compounds of cyclohexane acetic acid, cyclohexane propanoic acid and cyclopentane propanoic acid, as well as derivatives or isomers thereof.
  • cyclopentane propanoic acid is present in a range of between about 5% to about 35% (w%/w%).
  • the cyclohexane acetic acid is present in the above-described allomone compositions in a range between about 25% to about 60% (w%/w%).
  • the cyclohexane propanoic acid is present in the above-described allomone compositions in a range between about 28% to about. 65% (w%/w%).
  • the allomone composition comprises one or more of the following cyclic compounds: about 12% to 26% (w%/w%) cyclopentane propanoic acid from about 34% to about 49% (w%/w%) cyclohexane acetic acid and from about 32% to 51%(w%/w%) cyclohexane propanoic acid or derivatives or isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more of their derivatives and/or one or more of their isomers thereof; in an acceptable delivery vehicle.
  • the allomone composition comprises at least two of the following cyclic compounds: about 12% to 26% (w%/w%) cyclopentane propanoic acid from about 34% to about 49% (w%/w%) cyclohexane acetic acid and from about 32% to 51% (w%/w%) cyclohexane propanoic acid or derivatives or isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more of their derivatives and/or one or more of their isomers thereof.
  • Derivatives of these cyclic acids described above can also be utilized in the composition such as esters, aldehydes, ketones, amides, alcohols or salts of these compositions
  • An enhancer composition containing between 5% to 35% (w%/w%) can also be added to the allomone composition, if desired.
  • This enhancer composition comprises volatile organic compounds and mixtures of these compounds.
  • This enhancer compound may be species-specific in nature and may vary according to the insect species for which the composition is used.
  • the compounds that can be used in the enhancer composition include, but are not limited to, amines, fatty acids from indolic derivatives, esters of these amines and fatty acids, ketones such as acetone, alcohols, sterols and the like.
  • Nontoxic fillers can also be added to the composition, which include fatty acids, alcohols, amines, squalene and glycerol.
  • the cyclic propanoic acids and acetic acids are generally liquid in nature and can be diluted in various solvents in which these compounds are miscible. These solvents include, for example, ethanol, benzene, propyl alcohol, propylene glycol, isopropanol, chloroform, absolute ethanol, volatile oils, paraffin and the like.
  • the solutions, containing the allomone compositions described above, can then be formulated in sprays or aerosols.
  • the solutions can be microencapsulated, can be placed in liposomes, can be placed in microparticles, polymers, gels or in a slow release matrix.
  • the insect repellant solution can be placed in candles or can be released through an electronic vaporisation or diffuser. More specifically, the solutions containing the allomone composition at a concentration between about 1 % to about 5% (w%/w%) can be formulated in liquid paraffin and used in an electric diffuser. These diffusers are known in the art as illustrated, for example, in the product DAP diffuser, which works like a plug in air refreshener, continuously releasing the composition into the environment. In another aspect the present invention provides a non-electric diffuser, which slowly disperses the allomone composition of the present invention.
  • the allomone solution is dispersed in a resin such as polyolefins acrylic resins, MATERBI®, any resins and the like, at a concentration between about 2% to about 10% (w%/w%) and forms a solid material that can be further shaped in the form of blocks, circles, ovals etc.
  • concentration of the allomone solution can be formulated in paraffin which solidifies forming a candle.
  • a liquid dispensing device is also part of the present invention such as those disclosed in U.S. Patent 5,242,111. In this formulation between about 2% to about 10% (w%/w%) of the allomone solution of the present invention is used in such a device.
  • a spray aerosol under pressure with a mechanism that can be programmed to spray a specific amount of the allomone solution also .forms another aspect of the present invention.
  • the concentration of the allomone solution is between about 1 % to about 4% (w%/w%) .
  • the allomone solutions can also be formulated in cosmetic products such as in creams, lotions, gels, bath gels, as towelettes, soap and shampoos.
  • the allomone solution of the present invention is combined with surfactants such as ammonium lauryl sulfate, triethanolamine lauryl sulfate, as well as other ingredients such as thickeners, preservatives, emulsifiers and the like to produce shampoos.
  • surfactants such as ammonium lauryl sulfate, triethanolamine lauryl sulfate, as well as other ingredients such as thickeners, preservatives, emulsifiers and the like.
  • Gels and shower/bath gels can be obtained by combining between about 0.05% to about 2%(w%/w%) of the allomone solution of the present invention with either a surfactant and carboxy polymethylene (carbomer) for the bath gel or only carbomer for the gel.
  • An aqueous spray can be prepared by combining between about 0.05% to about 2% (w%/w%) of the allomone solution, water and a surfactant.
  • Creams are also encompassed by the present invention and are obtained by combining between about 0.05% to about 2% (w%/w%) of the allomone solution of the present invention in an emulsion.
  • the allomone solution of the present invention can be formulated with an alcohol to be used in a lotion or placed on a towelette.
  • the lotion is formulated with ethanol and water and can be used also as a spray and in this embodiment the allomone solution is generally in a concentration of between about 0.01 % to about 1.5% (w%/w%).
  • the allomone solution For impregnating the allomone solution on a towelette, generally between about 0.05% to about 3% (w%/w%) of the allomone solution of the present invention is used.
  • the allomone solution of the present invention can also be formulated in a polymer or impregnated in a resin and can be molded or extruded into a variety of shapes and objects such as collars for animals, granules for use in containers, thin layers that can be encased with, for example, plastic or cardboard.
  • a molded, extruded or resin impregnated polymer any polymer can be used in this formulation that can retain the desired shape and emit into the atmosphere the allomone composition of the present invention.
  • a combination of polyvinyl chloride and polyurethane polymer is used, the polymer is molded and the concentration of the allomone solution added to the polymer is between about 0.05% to about 3% (w%/w%).
  • the polymer is extruded and the concentration of the allomone solution added to the polymer is between about 0.05% to 3% (w%/w%).
  • a resin impregnated with between about 0.5% to about 10% (w%/w%) of the allomone solution of the present invention is also encompassed by the present invention.
  • the polymer composition is polyvinyl chloride, MATER-BI®, which is a starched based polymer is used and the composition is granulated.
  • the present invention encompasses microencapsulated sprays that can be used outdoors, around pools and patios. This spray is composed of water, surfactant and microcapsules and contains between about 5% to about 20% (w%/w%) of the allomone solution of the present invention.
  • the present invention can also be formulated for veterinary use.
  • the allomone solution is formulated with a skin absorption enhancer such as azone, oleic acid, ethanol, glycols such as propylene glycols, DPPG, fatty acids and esters such as Labrasol, Labrafil®, Hydrophile and transcutol.
  • the allomone solution is generally present in a concentration of between about 0.005% to about 1 %(w%/w%).
  • the allomone product for veterinary use can be placed in an applicator and used as a spot-on, line-on or a liquid that can be poured onto the animal. It can be also in the form of a spray or in a liquid form that can be used as a dip.
  • composition of the present invention can also be encapsulated, using methods known in the art such as via spray cooling, coacervation, polymerization, phase separation, solvent evaporation, coextrusion, fluidized bed, disk and the like.
  • the composition can be encapsulated using hexadecanol, gelatin and gum, a polysachharide such as Chitosan® or silicate.
  • the solutions of the present invention can be simply diluted in a solvent and applied to various areas manually such as with a brush, or sponge. Different scents can be added to the above formulations such as lavender, cedar, rose lemon and the like.
  • the compositions of the present invention can be used to repel insects in a variety of environmental surroundings.
  • the present invention concerns a method to repel insects the method comprising placing in the environment a composition comprising an allomone derived from a badger.
  • the allomone is a composition comprising one or more of the following cyclic compounds of cyclopentane propanoic acid, cyclohexane acetic acid, cyclohexane propanoic acid and/or derivatives and/or isomers thereof.
  • the present invention provides a method of repelling insects, said method comprising placing in an environment an allomone composition comprising one or more of the following cyclic compounds: cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid or derivatives thereof or isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more derivatives and/or one or more isomers of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid, which composition repels insects, wherein said cyclic compounds, derivatives or isomers thereof are each present in a concentration of 5% to about 35% cyclopentane propanoic acid (w%/w%) or between about 25% to about 60% (w%/w%) cyclohexan
  • the present invention provides a method for repelling insects comprising placing in the environment a composition comprising one or more of the following cyclic compounds: between about 12% to about 26% (w%/w%) cyclopentane propanoic acid, between about 34% to about 49% (w%/w%) cyclohexane acetic acid, between about.32% to about 51 % (w%/w%) cyclohexane propanoic acid and derivatives and isomers thereof, as well as mixtures of cyclopentane propanoic acid, cyclohexane acetic acid and cyclohexane propanoic acid with one or more isomers or derivatives thereof.
  • the method comprises encapsulating at least one of the above-mentioned compositions and placing the encapsulated composition in the environment to repel insects.
  • the method comprises electronically diffusing at least one of the above-mentioned compositions in the environment to repel insects.
  • the present invention relates to a method of repelling insects wherein a candle containing at least one of the above- mentioned compositions is placed in the environment to repel insects.
  • a method for repelling insects by placing on a mammal at least one of the above- mentioned allomone compositions
  • Example 2-Testinq of the Secretions This test was performed using the various secretions obtained from the different parts of the badgers in Example 1 and used Polistes wasps such as Polistes nimpha Christ., Polistes gallicu sL., and Polistes sp.
  • Polistes wasps such as Polistes nimpha Christ., Polistes gallicu sL., and Polistes sp.
  • a group of 10 insects was placed in a clear box having the dimensions of 70 cm in height, 70 cm. in width and 70 cm. in length. In the center of the box a small bowl was placed which contained a mixture of pieces of melon and honey, which was used as the bait. See, Figure 1 for a schematic representation of the box used in this experiment. The insects were left to eat for two minutes before the compress soaked with one of the secretions obtained in Example 1 was left just next to the bowl that contained the bait.
  • the compresses were placed in glass flasks containing 10 . ml of acetonitrile that was the solvent used for desorption. The use of acetonitriie also prevented bacterial growth and the samples could be stored for a long time.
  • the samples were analyzed individually for each secretion obtained. If the sample revealed that one composition was not really concentrated in the sample and directly identifiable, the samples were then pooled. Each sample was then evaporated under a stream of azote to achieve a volume of 2 ml. 2.0 ⁇ l samples were injected and then analyzed using a GC/MS chromatograph GC 8000® of Fisions Instruments. The mass spectroscopy was performed on a Fisons Instruments VG Quattro®.
  • Example 4-Screenin ⁇ of the Insect or Wasp Repulsive Allomone After establishing the main components of the insect or wasp repulsive allomone, as represented in Table 3, further screening was undertaken to establish what species were sensitive to this wasp repulsive allomone composition.
  • the order Hymenoptera was first tested relying on the heliotropism of these particular insects. It was well known that Hymenoptera insects are attracted by a source of light that is situated over them. Also a bee placed in a tube has a tendency to climb the tube, even if the sole opening is underneath. Therefore, a source of light that is placed above a tube has an attractive effect.
  • the apparatus used for this example is set forth in Figure 7.
  • Example 3 It is a cage of 40 cm that is lined with Plexiglas to reduce the incoming light. At two opposite and opposing ends an orifice of 1.5 cm was made to which two tubes of transparent glass were inserted at an angle of 45°. At each end of these tubes a light source was placed. The insect or wasp repulsive allomone in Example 3 was applied with a tweezer on the inside of one of the two tubes. To eliminate any prejudice of one light source from the other, the test was run using the insect or wasp repulsive allomone altering between one light source and the other. The insects were introduced in a group of 10 in the apparatus and lodged for a period of 10 minutes.
  • the test consisted solely of introducing at the exit of the cage a circle of 30 cm in diameter outlined with a solution of the insect or wasp repulsive allomone of Example 3 or a placebo which was a solvent. Twenty (20) ants were placed in the central of the cage and observed. The ants resting in the circle or leaving the circle were noted within a 30 minute time period.
  • the solution of the insect or wasp repulsive allomone that was used in this experiment was in a solution of ethanol titrated with 2% of the insect or wasp repulsive allomone.
  • the formula used was the following: 40% (w%) cyclohexyi acetic acid; 20% (w%) cyclopentane propanoic acid and 40% (w%) cyclohexyi propanoic acid.
  • the species utilized in this example were the following: Family of Vespidae: Polistes gallicus (and Polistes sp.) Vespula vulgaris L. Vespula sylvestris Scopoli Vespulus gemanica Fabr. Vespa crabro L.
  • Example 5 screening of other Insects Other orders of insects were then screened.
  • the order of Diptera which are true flies and mosquitoes were then tested including the species Nematocera (mosquitoes and blood sucking flies) and part of Brachycera (flies and gad flies, breezes and horse-flies).
  • Example 5 A- Protocol used for testing Brachycera
  • the species Calliphoridae (beef flies) and Muscidae (free flies) were the object of this experiment.
  • This method utilized the measurement of frequenting a bait of various meat that is situated next to an electric diffuser containing the insect or wasp repulsive allomone of Example 3.
  • the bait was placed next to the diffuser and a video camera was placed such as to film the insects present on the bait.
  • the insects were counted each minute for 10 minutes after the diffuser was placed nearby.
  • the insects were placed in the sun for 20 minutes prior to repeating the test using the diffuser containing the insect or wasp repulsive allomone.
  • Table 6 Table 6
  • Example 5 B-Protocol used for Testing Nematocera A panel of white squares of 30 centimeters were placed next to each other and covered with sticky paper (ribbon type that snares flies)and were placed in the proximity of a bush situated in the environment of these insects. Halogen projectors were hung on each panel. The panels were set in place 18 hours to 8 hours the next day. Each night, a part of the panel was treated with a spray containing an alcoholic solution of the insect or wasp repulsive allomone of Example 3 titrated at 5% (w%). The location of the panels which were treated and nontreated were changed each day and each site was treated two times with and without the insect or wasp repulsive allomone.
  • the non-treated panel was sprayed with the 90% ethanol solvent used to dilute the insect or wasp repulsive allomone. Each day the sticky paper was collected and placed to settle in dichloromethane (DCM). This permitted the solubilization of the glue. The liquid that was obtained was then filtered and the insects that were obtained were rinsed with new DCM and then placed in a beaker to examine and identify the species. Also the product of each trap for each night was assembled onto a glass slide. The results are shown in Figures 6 and 7. The insect or wasp repulsive allomone has a very significant activity on the Phlebotomus insects and a significant activity towards Culex and Theobaldia. The activity was nonsignificant for the Culicoides.
  • DCM dichloromethane
  • Example 6- Screening at Meal time It is known that wasps are attracted to certain food such as roast beef, pasta, melon and fresh cut fruit.
  • This example illustrates the use of the insect or wasp repulsive allomone to repel wasps from tables during meals.
  • Three different media were utilized. The first media that was chosen was a simple paraffin candle. The paraffins that were chosen had a fusion point between 52° C and 56° C. The particular paraffins were chosen such that the insect or wasp repulsive allomone was not altered in its chemical content.
  • the diameter of the candle was not inferior to 5 centimeters and thus permitted the vaporization of the insect or wasp repulsive allomone at a sufficient distance from the flame and thus limited the destruction of the active principal in the cone of the flame.
  • the candles that were tested contained 1%, 2%, 4% and 10% (all w%) of the insect or wasp repulsive allomone of Example 3.
  • the second media that was chosen was solid in form.
  • the insect or wasp repulsive allomone of Example 3 was adsorbed in a resin called Mater Bi®. The resin was charged with 2.4 % to 8 % (w%) of the insect or wasp repulsive allomone.
  • the granules were contained in a container that was perforated and placed beneath a ventilator.
  • the third media was a classic system of diffusion for insects in the home.
  • the electric diffusors that were utilized were made by the company ZOBELE ( reference LMH04).
  • the insect or wasp repulsive allomone of Example 3 was placed in a solution of petroleum (ISOPAR*) at the concentrations of 5% and 10% (w%).
  • the reservoir of each diffuser contained 36 grams of the solution.
  • a piece of hot roasted chicken and a piece of ripe melon were placed on two white plates.
  • the bait of this type was placed at 50 cm, 70 cm, 1 m and 1.5 m from the system that emitted the insect or wasp repulsive allomone.
  • the test lasted 60 minutes and the number of wasps was counted on each plate during this test.
  • Table 7 The results are set forth in Table 7 below:
  • Example 7-Testing of Olfactive Mask Since the insect or wasp repulsive allomone has a particular odor that may be offensive to some people, an oleofactive mask was investigated that did not alter the efficacy of the insect or wasp repulsive allomone.
  • Four different aromas were tested on a panel of 10 people. These aromas were an essence of tamarin, an essence of lemon, an essence of lavender and an essence of cedar wood.
  • a mixture of Mater-Bi, 9% (w%)of the insect or wasp repulsive allomone of Example 3 and 1 % (w%) of the essence was utilized. The 10 people judged the smell of each of the products.
  • Example 6 The mixtures containing the essence of tamarin and the cedar wood were deemed to be agreeable. The product containing the cedar wood was deemed to be the most agreeable. The same test as in Example 6 was redone using the formula stated in this example with cedar wood. The results were the same as those obtained in Example 6, Table 7.
  • Example 8-Testing in a Pool Environment It is known that the odors of pools and the beach often attract insects. The problem with using the insect or wasp repulsive allomone near these places is obvious; i.e., the atmosphere is often quite humid and it requires continuous application to repulse the insects. Moreover, the water in a pool contains chlorine that is susceptible to degrade the insect or wasp repulsive allomone. To overcome the above problems, the insect or wasp repulsive allomone of Example 3 was encapsulated in various media.
  • the following procedure was followed using the technique of nebulization or spray cooling (according to Report * No. 971806 of MICROLITHE (June 1997_ SA MICROLITHE, BP 115-13075 LA CIOTAT CEDEX).
  • the allomone of Example 3 was mixed with the fatty acid of either paraffin or hexadecanol and melted.
  • the mixture was then transferred to another reservoir that had a thermostat placed underneath a nozzle that feeds by the venturi effect and gravity.
  • the nozzle was heated at 55°C.
  • the air of pulverization was at an ambient temperature.
  • the highest fall of the drops was 3 meters in ambient air.
  • the microspheres that were obtained had a size between 50 ⁇ and 300 ⁇ .
  • the products encapsulated in paraffin were adjusted by adding powdered silicate..
  • the product obtained contained 15% (w%) allomone and 85% (w%)hexadecanol.
  • the allomone was diluted 50% (w%) in a neutral oil and emulsified in a solution diluted with a flower scented gelatin at a temperature of 40° C.
  • a solution of acacia gum was added to lower the pH of the mixture just at the moment when coacervation commenced.
  • the products obtained by this method contained: 7.65% (w%) allomone, 1.5% (w%) gelatin and gum and 83.5% (w%) of a water suspension.
  • the following procedure was used to encapsulated by coacervation using the polysaccharide Chitosome®. Like the previous procedure the allomone was diluted in a solution of Chitosome® to form an emulsion.
  • the product obtained by this process had 10% (w%) allomone of Example 3 and 90% (w%) silicate.
  • the two suspension forms were tested using the same procedure.
  • a surface of 1 m 2 situated at the border of a pool was treated by applying 20 ml with a paint brush.
  • the zones that were treated were surrounded by non- treated boundary zones of 2 m by 1 m (2 m 2 ) as shown in Figure 10. All of the surfaces were sprayed 20 times per day with water from the pool.
  • the number of wasps that were present on the borders of the pool were counted each day at 9:00 a.m., 12 (noon), 15:00 p.m. and 18:00 p.m. in this experiment that started at the beginning of June.
  • the criteria of efficacy and the significant differences were 5% with the non-treated zones.
  • microencapsulated insect or wasp repulsive allomone in gelatin was also active 6 days after application.
  • the allomone composition of the present invention is tested on other insects from orders of Collembola, Protura, Diplura, Thysanura, Ephimerida, Odonata, Orthoptera, Dermaptera, Embiara, Pformicidae, Fulgoromorpha, lchneumonidae, Isopetra, Lectoptera, Trichoptera, Zoraptera, Corrondentia, Mallophaga, Anoplura, Thysanoptera, Hemiptera, Neuroptera, Coleoptera, Hymenpotera, Mecoptera, Siponaptera, Trichoptera and Lepidoptera according to at least one of Examples 4 to 6 set forth above.
  • the allomone composition of the present invention also repulses insects from these orders.

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  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

La présente invention concerne une composition permettant de repousser les insectes, laquelle composition contient une allomone provenant des sécrétions jugales d'un blaireau. Cette composition à base d'allomones comprend de l'acide cyclopentanepropanoïque, de l'acide cyclohexanacétique, de l'acide cyclohexanepropanoïque ou des dérivés ou des isomères de ceux-ci. La présente invention concerne également des procédés permettant de repousser des insectes dans divers environnements, y compris autour de la nourriture et de l'eau.
PCT/EP2004/009167 2003-07-30 2004-07-28 Allomones insectifuges WO2005013694A1 (fr)

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EP03291899 2003-07-30
EP03291899.7 2003-07-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016142775A1 (fr) * 2015-03-06 2016-09-15 Institut de Recherche en Semiochimie et Ethologie Appliquee Compositions sémiochimiques pour empêcher des insectes diptères hématophages de se poser sur des animaux et de mordre ces derniers
CN107691449A (zh) * 2017-11-12 2018-02-16 王龙 一种生物诱导的长效驱虫的组合材料，制备方法和用途

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"The Combined Chemical Dictionary", 2004, XP002308144, 1 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1950, APPLEWHITE, K.H.; SMITH, CARROLL N.: "Field test with mosquito and sand-fly repellents in Alaska", XP002308113, accession no. 1950:58105 Database accession no. 44:11008C-F *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1950, SMITH CARROLL N. ET AL.: "Investigations of tick repellent at Camp Bullis, Texas, 1948", XP002308116, accession no. 1950:8452 Database accession no. 44:8452 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1952, GOUCK, HARRY K. ET AL.: "Effects of some organic compounds and mineral oil on corn earworm eggs", XP002308115, accession no. 1952:33857 Database accession no. 46:5777C-E *
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1957, GOUCK, HARRY K. ET AL: "Repellency of homologous series of cyclohexane aliphatic acids and amides", XP002308114, accession no. 1957:68482 Database accession no. 51:68482 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016142775A1 (fr) * 2015-03-06 2016-09-15 Institut de Recherche en Semiochimie et Ethologie Appliquee Compositions sémiochimiques pour empêcher des insectes diptères hématophages de se poser sur des animaux et de mordre ces derniers
CN107529747A (zh) * 2015-03-06 2018-01-02 信息化学和应用神经研究所 用于防止吸血双翅目昆虫着地和叮咬动物的化学信息素组合物
CN107691449A (zh) * 2017-11-12 2018-02-16 王龙 一种生物诱导的长效驱虫的组合材料，制备方法和用途

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