[go: up one dir, main page]

WO1999021425A1 - Stimulateurs sensoriels et agents repulsifs d'animaux trigeminaux provenant de plantes - Google Patents

Stimulateurs sensoriels et agents repulsifs d'animaux trigeminaux provenant de plantes Download PDF

Info

Publication number
WO1999021425A1
WO1999021425A1 PCT/US1998/022537 US9822537W WO9921425A1 WO 1999021425 A1 WO1999021425 A1 WO 1999021425A1 US 9822537 W US9822537 W US 9822537W WO 9921425 A1 WO9921425 A1 WO 9921425A1
Authority
WO
WIPO (PCT)
Prior art keywords
species
alkylamide
extract
xanthoxylum
plants
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/US1998/022537
Other languages
English (en)
Inventor
Bruce P. Bryant
Igor A. Mezine
Gisela M. Epple
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.)
Monell Chemical Senses Center
Original Assignee
Monell Chemical Senses Center
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 Monell Chemical Senses Center filed Critical Monell Chemical Senses Center
Publication of WO1999021425A1 publication Critical patent/WO1999021425A1/fr
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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/36—Rutaceae [Rue family], e.g. lime, orange, lemon, corktree or pricklyash

Definitions

  • the present invention relates to sensory irritants and repellents in solvent extracts from certain plant species
  • sanshoamide from Xanthoxylum pipe ⁇ tum is described by Aihara, in Yakugaku Zasshi, 71 1112, 1951
  • the paper reports slight pungency ofthe alcohol solution ofthe compound, and does not report any pungency from the crystalline compound Sanshoamide was obtained from the non- volatile fraction of the ethereal extract of fresh, unripe, fruit collected in early summer.
  • the structure of sanshoamide is represented as N-2 ' -hydroxyl-2,4,8, 10-dodecatetraene- amide-1'.
  • 2, 6, 8, 10- dodecatetraenoic acid is an insecticidal compound isolated from Zanthoxylum species and Echinacea angustifolia roots.
  • the all-E form of this compound is commonly known as ⁇ -Sanshool, also an insect repellent. Dictionary of Natural Products. Vol. 2. D-F. p. 1939, Chapman & Hall, London, 1994. Also reported therein is 2, 4, 8, 10 -dodecatetraenoic acid from which sanshoamide is derived. Chapman & Hall, supra. Dube et al, Annals of Botany, 65:457 - 459, 1990 describe the antifungal and insect-repellent activity ofthe essential oil of Zanthoxylum a/atum. The insect- repellent activity ofthe essential oil was tested against Allacophora foveicollis Fabr.
  • Tachiyashiki et al. J. of Japanese Society of Nutrition and Food Science, 45(2): 123-128, April, 1992 describe the effects of the scent and/or appearance of kinome (Japanese pepper leaf, i.e., Zanthoxylum piper Hum) and lemon peel on human whole saliva secretion.
  • kinome Japanese pepper leaf, i.e., Zanthoxylum piper Hum
  • JP 58-213706 describes oral compositions for the prevention of dental plaque containing, inter alia, sanshool.
  • the compositions are reported to inhibit formation of deposits or detritus caused by bacteria. Amounts of 0.001-5 weight percent are indicated. Use in toothpaste, tooth powders, liquid dentrifices, mouthwashes, coating agents, and chewing gums are described
  • JP 01-294657 describes an anesthetic agent isolated from Zanthoxylum bungeanum which showed anesthetic activity when 610 mg were applied to the tongue.
  • the anesthetic compound is reported as having the formula 2'-hydroxy-N-isobutyl 2,4,5,11-tetradecatetraenamide.
  • the reference also describes the occurrence of hydroxy- ⁇ -sanshool in the extract.
  • JP 06-298659 describes topical preparations containing sanshool and sanshamide from Zanthoxylum piperitum to enhance sexual activity.
  • the preferred mixing ratio of extract from the Japanese pepper is indicated as 20-50 weight percent.
  • a crystalline compound isolated from Echinacea angustifolia, called echinacein, which produced excessive salivation and an intense, burning, paralytic effect on the tongue and on the mucous membranes ofthe lips and mouth in trace amounts has been described. J. Org. Chem., 32(5): 1646-7, 1967. The structure was reported to be identical to ⁇ -sanshool and neoherculin.
  • JP 07-090294 describes the use of essential oils rich in spilanthol for manufacturing toothpastes or other oral compositions
  • the structure for spilanthol is described as (2E,6Z,8E)-N-isobutyl-2,6,8-decatrienamide.
  • JP 6211675 and 6-211676 describe the use of sanshool extract from
  • Zanthoxylum piperitum in a composition for treating impotence preferably contains 5-90% of sanshool extract.
  • extracts from the genera Xanthoxylum and Echinacea have certain stimulatory effects in humans and, further, deterrent effects in other animals.
  • the structure of this compound is the same as that identified as hydroxy- ⁇ -sanshool discussed above.
  • the present invention relates to an additive for products for human consumption comprising alkylamide-containing extracts isolated from certain species of plants.
  • the present invention relates to an additive for products for human consumption comprising alkylamides isolatable from certain species of plants.
  • the present invention relates to an additive for oral-, hair- and skin-care products comprising an alkylamide-containing extract isolated from certain species of plants.
  • the present invention relates to an additive for oral-, hair- and skin-care products comprising alkylamides isolatable from certain species of plants.
  • the present invention relates to a method for enhancing the sensory effect of oral-, hair- or skin-care products comprising the addition of alkylamide-containing extracts isolated from certain species of plants.
  • the present invention relates to a method for enliancing the sensory effect of products for human consumption comprising the addition of alkylamide-containing extracts isolated from certain species of plants.
  • the present invention relates to a method for enhancing the sensory effect of oral-, hair- or skin-care products comprising the addition of alkylamides isolatable from certain species of plants. In a further aspect, the present invention relates to a method for enhancing the sensory effect of products for human consumption comprising the addition of alkylamides isolatable from certain species of plants.
  • the present invention relates to a method for repelling non-human animals comprising the application of alkylamide-containing extracts isolated from certain species of plants to materials susceptible to damage by these animals.
  • the present invention relates to a method for repelling non-human animals comprising the application of alkylamides isolatable from certain species of plants to materials susceptible to rodent damage.
  • the present invention relates to a method for stimulating certain thermal and/or mechanosensory neurons in the skin or mouth of an animal comprising the application of alkylamide-containing extracts from certain species of plants and, therefore, altering or inducing thermal or tactile sensation.
  • the present invention relates to a method for stimulating certain thermal and/or mechanosensory neurons in the skin or mouth of an animal comprising the application of alkylamides isolatable from certain species of plants and, therefore, altering or inducing thermal or tactile sensation.
  • Figure 1- Multiwavelength chromatogram of a semipurified extract of Xanthoxylum obtained from Nepal. Two of the peaks of the complex of 3 peaks at approximately 10 minutes are active in human sensory tests.
  • FIG. 2 Responses of cultured trigeminal sensory neurons to 15 seconds of stimulation with pentanoic acid (pH 7.0), pH 6.0 HEPES, zingerone (10 ⁇ M), capsaicin (100 nM), hydroxy- ⁇ -sanshool (4.8 ⁇ g/ml), and KC1 (50 mM).
  • pentanoic acid pH 7.0
  • pH 6.0 HEPES pH 6.0 HEPES
  • zingerone 10 ⁇ M
  • capsaicin 100 nM
  • hydroxy- ⁇ -sanshool 4.8 ⁇ g/ml
  • KC1 50 mM
  • neurons are differentially sensitive to capsaicin (Neuron 3) and hydroxy- ⁇ -sanshool (Neurons 1 and 2).
  • Neuron 1 and 2 one neuron is sensitive to both protons and hydroxy- ⁇ -sanshool.
  • Figures 3A-B Activation of sensory neurons by hydroxy- ⁇ -sanshool. Action potentials were recorded from the lingual branch of the trigeminal nerve of rat. The frequency of action potentials increases from panel A to B. The neuron (action potentials) indicated above was also sensitive to moderate cooling.
  • Figures 4A-B Effect of hydroxy- ⁇ -sanshool on tactile responses of trigeminal neurons. Light tactile stimuli are indicated by arrows. 4A. Action potentials before application of hydroxy- ⁇ -sanshool to the tongue. 4B. Action potentials approximately 4 minutes after application of hydroxy- ⁇ -sanshool to the tongue. The frequency of action potentials increased during each brief tactile stimulation.
  • Figures 5A-B Activation of a cold nociceptor (indicated by arrow) by hydroxy- ⁇ - sanshool, causing it to fire bursts of 2-4 action potentials at normal tongue temperature, 35 °C.
  • Panel A is before treatment of tongue with hydroxy- ⁇ -sanshool
  • panel B is 4 minutes after treatment.
  • novel sensations are elicited in the mouth by solvent extracts from species of Xanthoxylum, including, but not limited to, X. alatum and X. americanum, and Echinacea, including, but not limited to, E. angustifolia and E. purpurea, in humans, and have further identified the responsible compounds therein - alkylamides. It is expected that other plant species contain alkylamides similar to these, i.e. similar in effect.
  • the extracts can be prepared from the fruit, roots, leaves, and bark of the plants.
  • the solvent used is ethyl acetate, although other solvents can be used.
  • the extracts elicited sensations that are unlike the irritation produced by the commonly used sensory irritants - i.e., capsaicin, piperine, and zingerone.
  • Xanthoxylum and Echinacea extracts were tested by drying equal volumes of solvent extracts on filter paper and testing on several human subjects for the intensity and character of sensation. Separation of the substances in these extracts, using HPLC, yielded several active peaks that are active when sampled on the tongue or in the mouth when dissolved in ethanol. The sensations produced by the active substances are different than those produced by ethanol alone. While ethanol is characterized by sensations of heat and pain, substances in Xanthoxylum and Echinacea elicited sensations varyingly described as numbness, tingling, enhanced cooling on inspiration of air, a 'buzzing' type of irritation, and, in some subjects, pain.
  • Black-tailed deer (Odocoileus hemionus columbianus) were repelled from eating apples treated with extract. Their initial repulsion occurred without oral contact of the food/extract, suggesting that volatile compounds contained in the extract are repellent in this species.
  • the extracts were also found to be repellent in birds. Given the sensory nature of these extracts, we disclose their use, and the use of the active compounds therein, as human sensory stimuli, for, for example, increasing the sensory impact and/or adding "freshness" to oral-, hair-, or skin-care products, and products for human consumption.
  • Contemplated uses for oral-, hair-, and skin-care products include, but are not limited to, flavor modifiers or enhancers for use in dentrifices, dental floss, mouthwashes; additives for, for example, shampoos, preferably dandruff shampoos; and topical analgesic creams, and massage oils.
  • Contemplated uses for human consumption include, but are not limited to, breath mints, throat lozenges, confections (e.g. chewing gum, "fire” ball candies), ice creams, oral medications — e.g.. , those which require chewing or sucking - etc.
  • the extracts and compounds are included in these products to produce increased sensory impact and/or induce a novel feeling of freshness similar in effect, but distinctly different, from the pungency of pepper or the cooling of mint.
  • the tingling feeling disclosed herein produced by the extracts/compounds is distinct from an anesthetic effect (i.e., the lessening of a feeling) and is a desirable sensation for many oral-care products and some food items.
  • the extract of non-volatile compounds is preferably used to eliminate potentially odorous or bitter compounds that may have an undesirable impact.
  • Extracts containing both volatile and/or non-volatile compounds are suitable for such uses.
  • An amount of the extract or compound sufficient to enhance the sensory effect of the product to which it is added is to be used. Such an amount will stimulate thermal and/or mechanosensory neurons, without necessarily stimulating high threshold pain receptors, in the mouth or on the skin or scalp. This amount will be readily ascertainable by persons of skill in the art.
  • An exemplary amount for the extract is about 5 to about 50 microliters/gram of sample; an exemplary concentration range of the alkylamide is about 150 to about 500 micrograms/ 100ml H 2 O.
  • the volatile and non-volatile extracts are suitable.
  • the extracts and compounds can be used to reduce or eliminate depredation of materials generally susceptible to depredation including, but not limited to, crops, livestock feedlot, crops, seeds, seedlings, telephone cables, electrical cables, containers for discarded refuse, packaging, fabrics, and plastics.
  • depredation refers to contact an animal may have with materials which causes some destruction or diminution in value of said materials, including consumption.
  • An agent is repellent if it substantially reduces depredation of a material as compared to depredation of the same material in the absence of such repellent agent.
  • the value of a repellent is ultimately determined by the value of the material under depredation. For some valuable materials, a reduction of about 25 % in the rate of predation is considered substantial. Those of ordinary skill in the art will recognize methods of testing to determine the amount of compound which will provide the desired repellency effect.
  • extract refers to the material collected by extraction of plant matter using appropriate solvent(s).
  • isolated as used herein means separated from materials with which the compound is normally associated in the native state.
  • isolated by HPLC refers to a compound having the same, or substantially the same, structure as a compound obtained in the manner specified. Accordingly, synthetically produced compounds having the same, or substantially the same, structure are also contemplated and within the scope of the invention. By “substantially the same structure” is meant compounds having minor changes in structure, but retaining the effect described herein.
  • Example 1 Isolation of the active compounds from Xanthoxylum fruit
  • An ethyl acetate extract was obtained by extracting 60 grams of dried fruits 3x with 800 ml ethyl acetate, and then evaporating this material using a rotary evaporator (bath temperature 40°C) to give an oil-like, black-brown liquid with a characteristic aromatic odor, i.e. , the "ethyl acetate extract. " 10.7 grams of this liquid was obtained. This extract was substituted into ethanol and suspended in oil for testing of repellent properties against birds, deer, and voles.
  • the liquid extract was applied to a column (30x400 mm) packed with silica gel (Davisil grade 634 (Fisher), 100-200 mesh) and chromatographed in 5 % EtOH in hexane.
  • the collected fractions were analyzed by High Performance Thin Layer Chromatography ("HPTLC").
  • This material was re-chromatographed, using the same conditions as described above, to give a brown liquid (0.9 g) with almost no odor, i.e., the "alkylamide extract.”
  • This material was tested for repellent properties in rats after suspension in EtOH (5 ml) and vegetable oil (50 ml). Rat chow (Wayne Rodent Blocks) was soaked in the oil suspension until the food was saturated. The food absorbed 7.6% of its weight of oil suspension.
  • the alkylamide extract was further separated into individual compounds for structure determination and bioassay.
  • the alkylamide extract ( 0.9 g, above) was diluted in 90% EtOH (2 ml) and filtered through a C18 cartridge reparative size, Fisher). The filtrate was chromatographed (2x 1ml) using reverse-phase HPLC.
  • the conditions of HPLC separation were as follows: 1) Column: Zorbax C18 (21.2 x 250 mm), 2) mobile phase: 35 % iPrOH in water, 3) flow: 10 ml/min, and 4) detection: high speed scanning 200-360 nm.
  • HPLC High Pressure Liquid Chromatography
  • MS Mass Spectroscopy
  • Fragment 2 C(14)-C(10)-C(15), that is : (N or O)-C(Me) 2 -.
  • hydroxy- ⁇ -sanshool was determined by its ability to induce changes in intracellular calcium in characterized trigeminal sensory neurons, in vitro.
  • the measurement of intracellular calcium was performed as described in U.S. Patent Application No. 08/541 ,641 , incorporated herein by reference. Hydroxy- ⁇ - sanshool induced increases in calcium in neurons (high threshold pain receptors) that were sensitive to capsaicin, the pungent principle of the hot pepper and neurons that were insensitive to capsaicin. ( Figure 2).
  • Hydroxy- ⁇ - sanshool also increased the responses of tactile neurons to light touch (Figure 4).
  • hydroxy- ⁇ -sanshool activated a high threshold cold receptor (cold nociceptor) to fire bursts of action potentials ( Figure 5), an activity that is characteristic of cold- sensitive neurons that have been activated by very low (e.g., ⁇ 10-15 °C) temperature stimuli.
  • very low e.g., ⁇ 10-15 °C
  • Treated and untreated (control) dog food was presented to a wild population of magpies, Pica pica for 8 hours per day for 5 days.
  • Treated dog food was prepared using the ethyl acetate extract as described above. Significantly less treated food was consumed man control food (3-way, repeated measures, ANOVA, p ⁇ .01). This response indicates that the extract is repellent to magpies and, it is expected, repellent to birds in general.
  • man control food (3-way, repeated measures, ANOVA, p ⁇ .01).

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Botany (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Pest Control & Pesticides (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne de nouvelles utilisations de composés isolés du fruit d'espèces de Xanthoxylum et d'Echinacea, ainsi que des composés similaires provenant d'autres espèces d'épices et de fleurs, et les extraits d'huiles à partir desquels ils sont isolés. Les nouvelles utilisations comprennent des exhausteurs de goût, des additifs de produits de soins dentaires, capillaires et pour la peau, ainsi que des agents répulsifs d'animaux.
PCT/US1998/022537 1997-10-24 1998-10-23 Stimulateurs sensoriels et agents repulsifs d'animaux trigeminaux provenant de plantes Ceased WO1999021425A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95711297A 1997-10-24 1997-10-24
US08/957,112 1997-10-24

Publications (1)

Publication Number Publication Date
WO1999021425A1 true WO1999021425A1 (fr) 1999-05-06

Family

ID=25499083

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/022537 Ceased WO1999021425A1 (fr) 1997-10-24 1998-10-23 Stimulateurs sensoriels et agents repulsifs d'animaux trigeminaux provenant de plantes

Country Status (1)

Country Link
WO (1) WO1999021425A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807317A1 (fr) * 2000-04-10 2001-10-12 Indena Sa Compositions de soin capillaire
US6306443B1 (en) 2000-06-20 2001-10-23 Amway Corporation Method of increasing concentrations of caffeic acid derivatives and alkylamides and compositions containing the same
US6767560B2 (en) 2002-01-22 2004-07-27 Paul H Paek Fabrication method of oral care composition
JP2005533897A (ja) * 2002-07-25 2005-11-10 ジボダン エス エー 香り（Ｆｌａｖｏｕｒａｎｔ）化合物
WO2007092823A3 (fr) * 2006-02-07 2008-07-10 Whitehill Oral Tech Inc Enduits renfermant un sialagogue, pour dispositifs interproximaux
US8962057B2 (en) 2009-04-29 2015-02-24 The Procter & Gamble Company Methods for improving taste and oral care compositions with improved taste

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5401502A (en) * 1992-01-17 1995-03-28 Alfatec Pharma Gmbh Pellets containing plant extracts, process of making same and their pharmaceutical peroral or cosmetic use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5401502A (en) * 1992-01-17 1995-03-28 Alfatec Pharma Gmbh Pellets containing plant extracts, process of making same and their pharmaceutical peroral or cosmetic use

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807317A1 (fr) * 2000-04-10 2001-10-12 Indena Sa Compositions de soin capillaire
WO2001076539A1 (fr) * 2000-04-10 2001-10-18 Indena S.A. Compositions pour soins de cheveux
US6306443B1 (en) 2000-06-20 2001-10-23 Amway Corporation Method of increasing concentrations of caffeic acid derivatives and alkylamides and compositions containing the same
US6767560B2 (en) 2002-01-22 2004-07-27 Paul H Paek Fabrication method of oral care composition
JP2005533897A (ja) * 2002-07-25 2005-11-10 ジボダン エス エー 香り（Ｆｌａｖｏｕｒａｎｔ）化合物
WO2007092823A3 (fr) * 2006-02-07 2008-07-10 Whitehill Oral Tech Inc Enduits renfermant un sialagogue, pour dispositifs interproximaux
US8962057B2 (en) 2009-04-29 2015-02-24 The Procter & Gamble Company Methods for improving taste and oral care compositions with improved taste

Similar Documents

Publication Publication Date Title
US5466459A (en) Wax and capsaicin based pesticide
EP4382518A2 (fr) Composés et compositions insectifuges, et procédés associés
EP2405760B1 (fr) Extrait d&#39;euodia suaveolens scheff, compositions repulsives et leur utilisation
CN107518012A (zh) 一种高效驱蚊中药复方精油
Tuetun et al. Celery-based topical repellents as a potential natural alternative for personal protection against mosquitoes
Bharathi et al. Jasminum grandiflorum linn.-an update review
US9326520B2 (en) Pest repellent comprising geranylacetone
WO1999021425A1 (fr) Stimulateurs sensoriels et agents repulsifs d&#39;animaux trigeminaux provenant de plantes
CN107638313A (zh) 一种驱蚊精油及其制备方法
Epple et al. Zanthoxylum piperitum, an Asian spice, inhibits food intake in rats
Yabansabra et al. The effectiveness of Zodia leaves (Evodia suaveolens Scheff) oil as Aedes aegypti L mosquito repellent in Papua
Ogbuagu et al. Chromatographic, infrared spectral and anti-inflammatory studies of etthyl acetate and methanol extract of the seed of D. edulis
KR100754416B1 (ko) 모기 기피제 조성물
CN112219844B (zh) 一种植物源蚊虫驱避剂及其制备方法
KR20130030981A (ko) 모기 기피제
FI130620B (en) Insect repellent composition and method for controlling insects
Wairagu REPELLENCY AND TOXICITY OF Commiphora africana RESIN EXTRACT AND ITS CONSTITUENTS AGAINST Cimex lectularius AND CHARACTERIZATION OF ITS ACTIVE CONSTITUENTS
KR100391827B1 (ko) 양고추냉이로부터 추출한 양고추냉이 정유를 활성성분으로 함유하는 저장물 해충 방제제
YANIC COVID-19 CAMPHOR BAG DIY: Revealed: The Secret to Keep Covid-19 Breathing Symptoms at bay
KR20080101622A (ko) 모기 기피제 조성물
Bukowski et al. Tasty blueberries? Not this time: Everything about poisonous plants in Polish gardens and forests.
KR20080063015A (ko) 모기 기피제 조성물
VIJAYAN et al. 1. Department of Chemistry, University of Calicut, Khozhikode-673635 Kerala, India. 2. Department of Pharmacology, Government Medical College, Thrichur, Kerala, India
KR20060089208A (ko) 디히드로네페타락톤을 포함하는 방충제 조성물
KR20080063034A (ko) 모기 기피제 조성물

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

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)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA