WO2003015522A1

WO2003015522A1 - Plant oil and chemical compound having acaricidal activity

Info

Publication number: WO2003015522A1
Application number: PCT/KR2002/001183
Authority: WO
Inventors: Hoi-Seon Lee
Original assignee: Individual
Current assignee: Individual
Priority date: 2001-08-16
Filing date: 2002-06-21
Publication date: 2003-02-27
Anticipated expiration: 2004-02-16

Abstract

The present invention relates to an acaricidal composition. In particular, the present invention relates to acaricidal composition, comprising plant oils extracted from member selected from at least one group consisting of Pimpinella anisum, Laurus nobilis, Melaleuca leucadendron, Elettaria cardamomum, Pseudotsuga menziesii, Foeniculum vulgare, Ferula galbaniflua, Pelargonium ordoratissimum, Pelagonium radens, Pelagonium capitatum, Helichrysum augustifolium, Andropogon muricatus, Lavendula officinalis, Origanum majorana, Milissa officinalis, Citrus aurantium, Melaleuca viridiflora, Ravensara aromatica, Sassafras albudum, Tagetes erecta, Tagetes patula, Verbena officinalis, Thujopsis dolabrata and monoterpene compounds selected at least one group consisting of carvacrol, (+)-fenchol, geraniol, linanol, (-)-cis-myrtanol, trans-myrtanol, (-)-myrtenal, (-)-myrtenol, thujone, cis-verbenol, (-)-verbenone, menthone, eugenol, menthol, and indoline. The present invention shows potent acaricidal activities against mites as well as superior effect to conventional synthetic acaricide, therefore, said plant oils and compounds are expected to be useful as acaricidal composition.

Description

PLANT OIL AND CHEMICAL COMPOUND HAVING ACARICIDAL ACTIVITY

Technical Field

The present invention relates to an acaricidal composition contarπing an extract of plant or a monoterpene compound isolated therefrom.

Background Art

Various allergens are known which are transported through the air to trigger a human reaction. For example, it has been known for a long time that house dust can trigger allergenic reactions in humans. It was reported, as early as 1928 that the mites in the dust were the primary source of the allergenic response, but it was only in the 1960's that researchers appreciated its significance. It is believed that the feces of the dust mite trigger the immune response of the body, thereby giving rise to well known allergenic symptoms, such as asthma and rhinitis (Maunsell, K. et al: Lancet 1, pl267-1270, 1968). The mite belonging to Pylogryphidae family inhabits in dust and Dermatophagoides pteronyssinus (known as Der-p), Dermatophagoides farinae (known as Der-f), Dermatophagoides microceras, Euroglyphus maynei et al. causes the human having physically atopic constitution to an asthma or eczema and the like disease (See Voorhorst, R. et al; Asthma, 10(6), p329-334, 1964: International Workshop Report. The Journal of Allergy and Clinical Immunology, 83, p416-427, 1989: and bid, 89_^ pl046-1060, 1992). The most of mites found in Korea are dust mites i.e., Def-p, Der-f species found in carpet, clothes, furniture, mats and bedclothes etc. (De Boer, R.; The acari: reproduction, development, and life history strategies, NY. Chapman and Hall, p517-518, 1991). The dust mites hate sunlight and require an appropriate temperature and humidity condition for proliferation of offspring and human corneous tissue detached from dried skin for a source of food. Therefore, to kill the mites, various methods comprising cleaning all the dust in room, sterilizing household goods, clothes, carpet and the like at the temperature of more than 70°C and controlling a temperature and humidity have been studied till now. But the above methods have lots of barrier and difficulty in obtaining complete exterminating spectrum for the mites.

The compounds having acaricidal activity are known as lindane, pirimiphos-methyl, benzyl benzoate, dibutyl phthalate and diethyl -toluamides (Hellet-Haupt A. and Busvine, J. R.; J. Med. Entomol, 2(5), p551-558, 1974). But the use of lindane compound as a household acaricide is limited because of its high toxicity although the compound has most effective acaricidal activity and consistency.

Chemical control using by insecticide has been conducted to get rid of mites, however, the control causes to drug tolerance for some species of the mites, for example, some mites belonging to Pyroglyphid family showing drug tolerance for DDT and lindane, are found (Bronsijk, J.E.M.H. et al; Res. Popul Ecol, 8, p67-79, 1971) Therefore, many attempts are tried to substitute the conventional acaricide in the world.

Especially, natural acaricide using by plant extract and aromatic compound has been studied extensively (Miyazaki, Y. et al; Jpn. J. Biometeor. 26 pl05-108, 1989; Watanabe, F. et al; Shoyakugaku Zasshi 43 pl63-168, 1989; Yatagai, M. and Morita, S.: J. Japan Wood Res. Soc. 37^345-351, 1991). The present inventors have endeavored to develop a plant extract and aromatic compounds showing high acaricidal activity, and have found that various plant extract and compounds show potent acaricidal activities against some species of mites.

Disclosure of Invention

An object of the present invention is therefore to provide an extract of plant having potent acaricidal activity.

Another object of the present invention is to provide a monoterpene compound having acaricidal activity.

In an embodiment of the present invention, there is provided an acaricidal composition comprising plant oils extracted from member selected from at least one group consisting of Pimpinella anisum, Laurus nobilis, Melaleuca leucadendron, Elettaria cardamomum, Pseudotsuga menziesii, Foeniculum vulgare, Ferula galbaniflua, Pelargonium ordoratissimum, Pelagonium radens, Pelagonium capitatum, Helichrysum augustifolium, Andropogon muricatus, Lavendula officinalis, Origanum majorana, Milissa officinalis, Melaleuca viridiflora, Ravensara aromatica, Sassafras albudum, Tagetes erecta, Tagetes patula, Verbena officinalis and Thujopsis dolabrata. In another embodiment of the present invention, there is also provided a process for preparing plant oil from above mentioned plants characterized in subjecting above plants to successive- vapor evaporation method.

For example, above plant is sliced and dried in the shade. Then, together with one to twenty times, preferably, three to ten times volumes of water or —Cs lower alcohol, preferably, methanol, ethanol or isopropanol and about 0.5 to 2 times, preferably, 0.6 to 1 time volumes of nonpolar solvent preferably, hexane, ethyl-acetate, acetone, more preferably, hexane solvent than the weight of dried plant (V/W) is added to the dried plant and the mixture is subjected to successive- vapor evaporation extraction, percolation extraction, ultra-sonication extraction, reflux-cooling extraction or soxhlet extraction, preferably, successive-vapor evaporation extraction for a period ranging from 1 hour to 48 hours, preferably from 5 hours to 24 hours, at a temperature ranging from 0 to 150°C, preferably 10 to 100 °C. The extract is filtered, dried with drying agent, preferably, anhydrous magnesium sulfate, anhydrous calcium sulfate, anhydrous potassium sulfate, anhydrous silica gel, more preferably, anhydrous magnesium sulfate, concentrated under a reduced pressure at temperature ranging from 0 to 40°C, preferably, from 4 to 20 °C and the concentrates is sealed and kept in refrigerator. hi another embodiment, the compositions of the present invention include at least one terpene. Non-limiting examples of terpenes, which can be found in the compositions of the present invention, include cavacrol, (+)-fenchol, geraniol, linanol, (-)-cώ-myrtanol, trans- myrtanol, (-)-myrtenal. (-)-myrtenol, thujone, cis-verbenol, (-)-verbenone, menthone, eugenol, menthol and indoline, which can be isolated from said plant extract or purchased at any market place. The monoterpenes and the sesquiterpenes are the main components of essential oils.

Monoterpenes, derived from 2 isoprene units, are 10-carbon compounds (C, 0) and the sesquiterpenes, derived from 3 isoprene units are 15-carbon compounds (C, 5). Both mono and sesquiterpenes belong to the steam distillate fraction i.e. essential oils, because of their low boiling point. These compounds are known to be present in fragrant, volatile, essential oils of many plants including mints, pine, cedar, citrus, eucalyptus and spices.

The acaricidal composition of present invention comprises said plant oils or monoterpene compounds in an amount of 0.01 to 40 % (w/w), preferably, 0.1 to 20 % (w/w) with a sole or mixture type in the amount of total composition. However, the amount of said oil or compound could be modified according to the preparation of insecticide, spreading method, the area of spreading and the species of insecticide.

The inventive composition is used wherein mite inhabits, the preferable application methods are spreading treatment, decoction treatment, fumigation treatment and the hke, the dosage of application is the amount of conventional dosage of insecticide. The preferable formulations of said composition are liquid, emulsion, smoke, fumigation, spray, granule, solid and the like types.

The inventive composition may additionally comprise conventional carrier in accordance with a using method. It is preferable that said carrier is used as a appropriate substance according to the usage and application method.

The inventive composition comprises an insecticidal composition having acaricidal activity specifically against mite.

Specifically, the inventive composition is effective in Der-p or Der-f.

Additionally, it is preferable that said composition is applied as a form of volatile toxicant or fumigate.

Best Mode for Carrying Out the Invention

The following Example and Test Example are intended to further illustrate the present invention without limiting its scope.

Example 1: Isolation of plant oils from plants having acaricidal activity

Acaricidal plants i.e., of Pimpinella anisum, Laurus nobilis, Melaleuca leucadendron,

Elettaria cardamomum, Pseudotsuga menziesii, Foeniculum vulgare, Ferula galbaniflua, Pelargonium ordoratissimum, Pelagonium radens, Pelagonium capitatum, Helichiysum augustifolium, Andropogon muricatus, Lavendula officinalis, Origanum majorana, Milissa officinalis, Melaleuca viridiflora, Ravensara aromatica, Sassafras albudum, Tagetes erecta, Tagetes patula, Verbena officinalis and Thujopsis dolabrata were cropped in USA, Australia and Korea. The 23 species of plants were dried in the shade, minced with a slice and weighed at 300g respectively. 2000 ml of distilled water and 200 ml of hexane were poured to the sliced plants and the mixture was subjected to successive- vapor evaporation extraction with SDE apparatus (Nickerson & Likens) at 100 °C, for 6 hours. The extract was dried with anhydride magnesium sulfate, concentrated under a reduced pressure, sealed and kept in refrigerator.

Example 2: Preparation of monoterpene compounds having acaricidal activity

Acaricidal compounds i.e., carvacrol (catalog No. 22051), (+)-fenchol (cataog No. 46198), geraniol (catalog No. 48798 or 48799), (-)-cώ-myrtanol (catalog No. 70154), trans- myrtanol (catalog No. 70117 or 70155), (-)-myrtenal (catalog No. 70119 or 70125), (-)- myrtenol (catalog No. 70158), thujone (catalog No. 89230), cz^'s-verbenol (catalog No., 94879), (-)-verbenone (catalog No. 94882), menthone (catalog No. 63680), eugenol (catalog No. 35995 or 46100), menthol (catalog No., 63670 or 63671) and indoline (catalog No. 57240) were purchased from Fluka Co. located in Switzerland and linanol (Fluca: catalog No. 62140, Wako: catalog No. 126-00993) was purchased from Wako Co. located in Japan.

Test Example 1: Acaricidal activities of the plant oils in example 1.

The acaricidal activities of the plants oil in example 1 against various mites were determined by the procedure described in a literature (Watanabe, F. et al; Shoyakugaku Zasshi 4 , pl63-168, 1989; Yatagai, M. and Morita, S.; J. Japan Wood Res, Soc. 37, p345-351, 1991).

The preparation of Mites

Two species of mites, i.e., European house dust mite (Dermatophagoides pteronyssinus) and American house dust mite (Dermatophagoides farinae) were bred in breeding room mamtaining at relative humidity (75+5%) and temperature (25+1 °C) and the rnixture feed of fry feed and complex vitamin (Ebiose^® , Samil Pharm) was fed in a vessel (12.5 x 10.5 x 5 cm) and an appropriate saline solution was poured at the bottom of another vessel (17.5 x 17.5 x 17.5 cm). The mites were bred without exposing any insecticide.

The determination of acaricidal activity

Most important point among screening steps to identify biologically active compounds is setting an initial concentration of sample. In present invention, since the characteristic of mite is microscopic, the concentration was determined 1 mg of sample per 2 ml of microtube through repeated preliminary experiments. Various concentrations of plant oils (1.0, 0.5, 0.25, 0.125 and 0.062 mg each) were dissolved in 40 μi of methanol, each solution was poured in 2 ml of colorless microtube and the tube was stirred in order to the solution containing each sample can be spread and adhered to wall and tip of the tube thoroughly. And then, the methanol was removed in freeze dryer for 1 hour. 25 numbers of mites were added to each tube and tested at the temperature of 25±1°C. The mites were selected from observing the activities of mites with microscope. The result was tested after 24 hours by microscopic examination (x 20) and determined by the criteria that motionless mites were regarded as dead one when stimulating appendage and body by minute brush. All test were repeated at 5 times and the comparison of average value between acaricidal rates was calculated by formula of Scheffe' test (SAS Institute, 1996). Control group was treated with same procedure without plant oil.

The acaricidal rate of plant oils in example 1 was shown in Table 1 and 2, wherein identical letter i.e., "a" and "b" means that the average showed no significant difference statistically (P = 0.05, Sheffe' test) and the rate of insecticide was shown by transforming to arcsine square root.

[Table 1] Acaricidal activities of the plant oils against Dermatophagoides pteronyssinus

[Table 2] Acaricidal activities of the plant oils against Dermatophagoides farinae

As can be seen in Table 1 showing the result of acaricidal activities tested in Dermatophagoides pteronyssinus, all the 23 plant oils in Example 1 showed 100% of acaricidal rate at the concentration of each 1 mg and 0.5 mg, in the concentration of 0.125 mg, the plant oils from Pimpinella anisum, Laurus nobilis, Elettaria cardamomum, Ferula galbaniflua, Pelargonium ordoratissimum, Pelagonium radens, Pelagonium capitatum, Helichrysum augustifolium, Andropogon muricatus, Lavendula officinalis, Citrus aurantium, Melaleuca viridiflora, Sassafras albudum, Tagetes erecta, Tagetes patula, Verbena officinalis and Thujopsis dolabrata showed more than 70% of acaricidal rate. However, in the concentration of 0.062 mg, the plant oils from Laurus nobilis, Pelargonium ordoratissimum, Andropogon muricatus, Verbena officinalis and Ωiujopsis dolabrata only showed more than 50% of acaricidal rate.

As can be seen in Table 2 showing the result of acaricidal activities tested in

Dermatophagoides farinae, all the 23 plant oils in Example 1 showed 100% of acaricidal rate all the concentration of 1 mg and 0.5 mg, in the concentration of 0.062 mg, the plant oils from Laurus nobilis, Pelargonium ordoratissimum, Andropogon muricatus, Verbena officinalis and Thujopsis dolabrata only showed more than 50% of acaricidal rate.

Test Example 2: Acaricidal activities of the monoterpene compounds in example 2.

The acaricidal activities of the monoterpene compounds in example 2 against various mites were determined as follows.

The determination of acaricidal activity

Identical determination methods with those of Test Example 1 were subjected to the monoterpene compounds i.e., carvacrol, (+)-fenchol, geraniol, linanol, (-)-cts-myrtanol, trans- myrtanol, (-)-myrtenal, myrtenol, thujone, cώ-verbenol, (-)-verbenone, menthone, eugenol, menthol and indoline in Example 2.

Table 3 showed acaricidal activities of monoterpene compounds in Example 1 against American house dust mite (Dermatophagoides farinae) and Table 4 showed European house dust mite (Dermatophagoides pteronyssinus) respectively.

[Table 3] Acaricidal activities of monoterpene compounds against Dermatophagoides pteronyssinus

As can be seen in Table 3, all the 15 compounds from Example 2 showed 100%) of acaricidal activities in Dermatophagoides pteronyssinus at the concentration of 0.5 mg, 0.33 mg and 0.25 mg. At the concentration of 0.010 mg, carvacrol, geraniol, linanol, thujone, eugenol and menthol showed acaricidal activities 73.8%, 76.7%, 36.2%, 35.3%, 23.4%, and 43.3%, respectively. These facts proved the monoterpene compounds have superior effect to control groups, i.e., benzyl benzoate and dibutyl phtalate.

[Table 4] Acaricidal activities of monoterpene compounds against Dermatophagoides farinae

As can be seen in Table 4, all the 15 compounds from Example 2 showed 100% of acaricidal rate in Dermatophagoides farinae at the concentration of 0.5 mg, 0.33 mg and 0.25 mg. At the concentration of 0.010 mg, carvacrol, geraniol, hnanol, eugenol and menthol showed acaricidal activities 76.7%, 83.3%, 43.2%, 36.6%, 34.1%, respectively. However, the control groups, i.e., benzyl benzoate and dibutyl phtalate did not show any significant acaricidal activities at the concentrations of less than 0.050 mg.

Industrial Applicability As mentioned above, the plant oils and monoterpene compounds of present invention showed potent acaricidal activities against mite as well as superior effect to conventional synthetic acaricide, therefore, said plant oils and compounds are expected to be useful as acaricidal composition.

While the invention has been described with respect to the above specific embodiments, it should be recognized that various modifications and changes may be made to the invention by those skilled in the art which also fall within the scope of the invention as defined in the appended claims.

Claims

1. An acaricidal composition comprising plant oils extracted from member selected from at least one group consisting of Pimpinella anisum, Laurus nobilis, Melaleuca leucadendron, Elettaria cardamomum, Pseudotsuga menziesii, Foeniculum vulgare,

Ferula galbaniflua, Pelargonium ordoratissimum, Pelagonium radens, Pelagonium capitatum, Helichrysum augustifolium, Andropogon muricatus, Lavendula officinalis, Origanum majorana, Milissa officinalis, Citrus aurantium, Melaleuca viridiflora, Ravensara aromatica, Sassafras albudum, Tagetes erecta, Tagetes patula, Verbena officinalis and Thujopsis dolabrata.

2. An acaricidal composition comprising monoterpene compounds selected from at least one group consisting of carvacrol, (+)-fenchol, geraniol, linanol, (-)-cts-myrtanol, trans- myrtanol, (-)-myrtenal, (-)-myrtenol, thujone, cts-verbenol, (-)-verbenone, menthone, eugenol, menthol and indoline.

3. The acaricidal composition of claim 1 or 2, wherein the composition comprises said plant oils or monoteφene compounds in an amount of 0.01 to 40 % (w/w) in the amount of total composition.

4. The acaricidal composition of claim 3, wherein the composition comprises said plant oils or monoteφene compounds in an amount of 0.1 to 20 % (w/w) in the amount of total composition.

5. The acaricidal composition of claim 1 or 2, wherein the composition has acaricidal effect against mite.

6. The acaricidal composition of claim 5, wherein said mite is Dermatophagoides pteronyssinus or Dermatophagoides farinae.

7. The acaricidal composition of claim 1 or 2, wherein said composition is applied as a form of volatile toxicants or fumigate.