KR20130025532A - Acaricide using petroselinum sativum extract - Google Patents
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- KR20130025532A KR20130025532A KR1020110088894A KR20110088894A KR20130025532A KR 20130025532 A KR20130025532 A KR 20130025532A KR 1020110088894 A KR1020110088894 A KR 1020110088894A KR 20110088894 A KR20110088894 A KR 20110088894A KR 20130025532 A KR20130025532 A KR 20130025532A
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
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- B01D11/02—Solvent extraction of solids
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Abstract
Description
The present invention relates to acaricide using petroleum selinium extract. More specifically, essential oil extracted from petroleum selinium; Apiol, which is a refined substance of the essential oil; It relates to acaricides containing at least one selected from the group consisting of the apiol derivatives as an active ingredient.
House dust mites belonging to the family Pyrogliphidae are the most important antigens causing allergic diseases such as bronchial asthma, rhinitis and atopic dermatitis, and have a high detection rate of about 63-91% in house dust. Especially in house dust, Dermatophagoides farinae ) and vertical dust mites ( D. pteronyssinus ) occupy the dominant species.
House dust mite breeds rapidly under the conditions of temperature 20 ~ 30 ℃ and humidity 60 ~ 80%, and it is the main food for human keratin, dandruff and mold. Therefore, bedding, sofas, formatting can be both regular home anywhere, such as carpets, curtains, bears a close relationship to the human living environment (Spieksma, F. TH M. 1991. Domestic mites;... Their role in respiratory allergy Clin Exp . Allergy 21:. 655-660).
The occurrence of house dust mite allergens is the most important cause of feces and fillings with strong allergens. Also, the number of house dust mites and the amount of allergens are proportional. Sensitization of house dust mites begins when house dust mite concentrations are more than 100 per 1 g of dust. D., Chapman, MD 1991. Dust mite allergen and asthma: report of a second international workshop.The UCB Institute of Allergy. 11: 29).
Therefore, in order to efficiently remove the dust within the dust mites benzyl benzoate (Benzyl benzoate), dibutyl phthalate (Dibutyl phthalate), diethyl - m - toluamide (N, N-Diethyl- m -toluamide ; DEET) , such as Synthetic formulations were used. However, the method has a short control effect even if the acaricide activity is effective, there are problems such as the appearance of drug-resistant individuals and human safety.
In order to overcome this problem, the hygienic pest control method using a variety of plants have recently been studied. In particular, research is needed to develop natural acaricides that show excellent acaricide effects against house dust mites and are harmless to the environment and the human body.
Plants contain abundant physiologically active substances such as terpenoids, phenols and alkaloid compounds. These bioactives selectively act only on limited species and are biodegradable as non-toxic products, making them safer to apply than conventional synthetic acaricides (Lee, CH, Jeon, JH, Lee, SG, Lee, HS 2010. Insecticidal properties of euphorbiaceae: Sebastiania corniculata -derived 8-hydroxy quinoline and its derivatives against three plant hopper species (Hemiptera: Delphacidae). J Korean Soc Appl Biol Chem 53: 464-469).
Korean Patent Publication No. 10-0819691 discloses a composition having an acaricidal effect on house dust mites using cinnamic aldehyde and tea-tree oils containing about 70-90% in cinnamon extracts. It is described. Korean Unexamined Patent Publication No. 10-2005-0116215 describes a dust mite removal and repellent composition using a substance contained in the extract component of seaweed.
Plant Petroselinum sativum is a biennial plant of Umbelliflorae, known for its various effects such as antiperitants, diuretics, blood pressure lowering agents, stomach ulcers, neurostabilizers, and menstrual accelerators. However, no research has been conducted on the control of ticks using petroleum setinium.
It is an object of the present invention to provide an acaricide that is harmless to humans and has excellent acaricide activity by using the plant petroclinium sativabum extract to overcome the problems of the organic synthetic acaricide.
The present invention is essential oil extracted from Petroselinum sativum ; Apiol, which is a purified material of the extracted essential oil; And it provides an acaricide containing at least one selected from the group consisting of the apiol derivatives as an active ingredient.
In the present invention, the 'essential oil' includes an essential oil extracted from petroleum setiboom.
The apiol derivative is 3,4-methylenedioxybenzene, 1-aryl-3,4-methylenedioxybenzene, 1-aryl-5 1-allyl-5-methoxy-3,4-methylenedioxybenzene, 3,4-methylenedioxybenzo nitrile, 1-bro Parent-3,4-methylenedioxybenzene (1-bromo-3,4-methylenedioxybenzene) and 5-chloro-3,4-methylenedioxybenzene (5-chloro-3,4-methylenedioxybenzene) Can be.
The acaricide may have acaricide activity against any one or more of a large leg dust mite (D. farinae) and vertical patterned mite (D. pteronyssinus).
Petrocelinium sativaum essential oil, apiol or apiol derivative compounds of the present invention can be widely applied to insecticides, fungicides, quasi-drugs and the like. It is particularly effective in controlling house dust mites such as large leg mites and vertical patterned mites.
Hereinafter, the effect of the composition of the present invention will be described in detail. The plant screened by the present inventors is Petroselinum sativum , and various derivatives including its purified material were selected to assay the acaricidal activity against large-legged dust mites and vertical patterned mites.
The compound purified from petrocelinium sativam is apiol of the formula (1), and examples of the derivative thereof are 3,4-methylenedioxybenzene [Formula 2], 1-aryl -3,4-methylenedioxybenzene (Formula 3), 1-aryl-5-methoxy-3,4-methylenedioxybenzene (1-allyl-5-methoxy -3,4-methylenedioxybenzene [Formula 4], 3,4-methylenedioxybenzo nitrile [Formula 5], 1-bromo-3,4-methylenedioxybenzene (1 -bromo-3,4-methylenedioxybenzene (Formula 6) and 5-chloro-3,4-methylenedioxybenzene (Formula 7).
In the present invention, it is possible to obtain apiol as a single substance by separating and purifying from petrocelinium sativab, and derivatives thereof may be obtained by using a commercially available product. For example, the apiol derivatives may be purchased from Sigma, Aldrich, and Fluka.
In addition, apiol and 3,4-methylenedioxybenzene compounds which have excellent acaricide activity against house dust mites have higher acaricide activity by modifying the chemical structure based on the structure of each component and can be used as a lead compound. have. Therefore, acaricides using these parent nucleus compounds can be applied to various kinds of pest control.
The apiol and its derivatives used in the present invention may be used alone or in a mixture, and a method such as a fumigation treatment is preferable. In addition, the solvent used in the formulations useful for the application of acaricide is preferably a volatile solvent as the active ingredient is completely dissolved at a desired concentration, and more preferably, hexane and acetone are used. These solvents are volatile and do not leave residue on use.
The acaricide may be prepared and used in any formulation such as aerosol, liquid, gel, or powder, preferably an aerosol formulation. As the propellant, one type of component selected from liquefied natural gas, dimethyl ester, compressed air, and compressed nitrogen may be used, and it is preferable to contain about 30 to 70% by weight. There is this remaining problem.
Essential oil extracted from the plant petrocelinium sativaum according to the present invention; Apiol and its derivatives, which are purified products of the essential oils, show excellent acaricide activity against house dust mites, which are a major cause of allergic diseases. The acaricide of the present invention can be utilized as a natural acaricide that can compensate for the disadvantages of existing synthetic acaricides.
1 is an EI-MS graph showing that the acaricide of the petroleum selinium sativaum essential oil obtained in Example 3 of the present invention is an apiol of the formula (1).
2 is a 1 H-NMR graph showing that the acaricide of the petroleum selinium sativaum essential oil obtained in Example 3 of the present invention is an apiol of the formula (1).
FIG. 3 is a 13 C-NMR graph showing that the fertilizer of petroleum selinium petroleum essential oil obtained in Example 3 is apiol of formula (1). FIG.
Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. However, the following examples are illustrative of the present invention and are not intended to limit the scope of the present invention.
[ Example One] Petroselinium From Sativa Essential Oils Separation
Petrocelinium sativam was washed three times in 1000 ml of distilled water and crushed by drying in an experimental dryer for 48 hours. 150 g of the ground sample and 1500 ml of distilled water were mixed and stirred, followed by two consecutive distillations by a continuous distillation extraction method, and 300 ml of hexane was added to a solvent flask maintained at 40 ° C., followed by extraction. Anhydrous magnesium sulfate (MgSO 4 ) was added to separate the obtained water layer and the hexane layer after extraction, and the water layer was dehydrated and filtered. The filtered sample was concentrated under reduced pressure at 30 ° C. using a rotary vacuum rotary concentrator, and then used to obtain pure essential oil components.
[ Example 2] Salbi Active black
2-1: Mites used in acaricide test
Two kinds of house dust mites, large leg dust mites ( D. farinae ) and vertical pattern mites ( D. pteronyssinus ) used in the present invention were bred without any acaricide exposure, and filled with sodium chloride solution to maintain relative humidity and mites It prevented the departure of. 12.5 × 12.5 × 7.0 cm 2 was placed in a container and fed using a feed mixed with feed and bioeze 1: 1. Breeding conditions were used in a dark condition incubator of 25 ± 1 ℃, relative humidity 75%.
2-2: Test of Acaricide Activity of House Dust Mites
The acaricide activity assay for house dust mites was performed using a fumigant bioassay, a kind of indirect contact method. In the fumigation method, acetone having no effect on mites and samples was used as a treating solvent. Each sample was dissolved in 20 μl of acetone and 10 μl of the paper disc was treated. The paper disks treated with the samples were dried in a fume hood for 30 seconds, and then inserted into the tube stoppers, and 30 individuals of large-legged mites and vertically-patterned mites were inoculated. All bioassays were performed in three replicates. The agitation rate was analyzed by ANOVA and tested for significance. The post-test was performed using Scheffe's test ( p = 0.05) (SAS Institute, 1990). The results are shown in Table 1 below.
[Table 1]
According to Table 1, the petroleum setinium petroleum essential oil showed a 100% abundance in a low concentration treatment of 2.4 μg / ㎠ for a large leg dust mite, about 95% acaricidal activity even for vertical pattern dust mites It can be seen that represents. As shown in Table 1, the petroleum setinium petroleum essential oil showed excellent acaricide activity to a low concentration, it can be seen that as the concentration of the treatment decreased the acaricide activity.
Example 3 Separation and Purification of acaricide active substance
The acaricide active material contained in the petroleum selinium sativaum essential oil prepared in Example 1 was separated and purified.
3-1: First Silica Gel Chromatography
10 g of essential oil was separated and purified from petrocelinium sativaum, which showed excellent acaricide activity against two house dust mites. Silica gel column column chromatography was used for the gradation of hexane and ethyl acetate in the ratio of 9: 1, 8: 2, 6: 4, and the fractionation layer was SP1, SP2, SP3, SP4. Eluted.
3-2: Secondary Silica Gel Chromatography
Of the four fractions, the SP2 layer showed excellent acaricide activity against two house dust mites. Therefore, the SP2 layer was divided into SP21, SP22 and SP23 in the ratio of hexane and ethyl acetate, 8: 2. Tick killing activity according to each fractional layer is shown in Table 2 below. The results are shown in Table 2 below.
[Table 2]
As shown in Table 2, the result of the acaricide activity assay, the SP23 layer showed excellent acaricide activity of 100% for two house dust mites. Actual cost activity at this time was also assayed using Scheffe's test ( p = 0.05).
3-3: high speed liquid chromatography
The SP23 layer was partitioned into SP231, SP232, SP233, SP234 layers by high-performance liquid chromatography under the conditions of maximum absorption wavelength 257 nm,
[Table 3]
As shown in Table 3, SP2332 showed 100% acaricide activity against two house dust mites.
3-4: Structural Analysis of Active Material
The final material SP2332 purified in Example 3-3 was confirmed the molecular weight by mass spectrometry, the structure was identified using 1 H-NMR (600MH Z ) and 13 C-NMR (150MH Z ). Therefore, the finally separated material was confirmed to be apiol (apiol) (FIGS. 1 to 3).
EI-MS (70 eV) m / z (% relative intensity):
1 H-NMR (CDCl 3 , 600MH Z ): 6.277 (1H, s ), 5.861-5.936 (2H, d , J = 45 MHz), 5.828-5.856 (1H, d , J = 16.8 MHz), 5.002-5.025 (2H, t , J = 13.8 MHz), 3.286-3.852 (3H, d , J = 15.6 MHz), 3.776-3.801 (3H, d , 15 MHz), 3.280-3.290 (2H, d , 6 MHz)
13 C-NMR (CDCl 3 , 150MH Z ): 139.056 (C-5), 138.719 (C-2), 137.327 (C-3), 136.241 (C-11), 135.096 (C-4), 125.753 (C -1), 115.347 (C-12), 108.176 (C-6), 101.500 (C-7), 60.123 (C-8), 56.839 (C-9), 34.060 (C-10)
[Formula 1]
Example 4 Activity Comparison of Apiol and Its Derivatives
remind In Example 3, the acaricidal activity of two house dust mites using the purified substance apiol and its derivatives is shown as LD 50 (half lethal dose) value in Table 4 below. The apiol derivatives shown below were purchased from Sigma. Benzyl benzoate and mite killer (Aekyung Co., Ltd.), which are synthetic acaricides, were used as control compounds.
In Table 4 below, the 95% confidence range indicates that the results can be trusted with a 95% probability.
[Table 4]
The half lethal concentration of the petroleum selinium sativa oil was 1.88 µg / cm 2 for large-legged dust mites and 2.25 µg / cm 2 for longitudinal patterned mites after 24 hours of treatment. From the above results, it can be seen that the petroleum setinium petroleum essential oil shows excellent aggression power against two types of house dust mites.
In addition, in Table 4, the LD 50 values of the large-legged dust mites and the vertical-patterned dust mites of apiol, which are active substances of petroleum setibum, were 0.81 µg / cm 2 and 0.94 µg / cm 2, respectively.
In addition, as a result of obtaining the LD 50 values for the two house dust mites using the same method as those of the six compounds having the structure similar to apiol and the control, the 3,4-methylenedioxybenzonitrile was 0.04 ㎍ / ㎠ , 0.03 ㎍ / ㎠ showed very high acaricide activity. Next, 2.75 μg / cm 2 of 1-aryl-5-methoxy-3,4-methylenedioxybenzene, 4.75 μg / cm 2, 4.06 μg / cm 2 of 1-bromo-3,4-methylenedioxybenzene, 3.56 μg / cm 2, 5-chloro-3,4-methylenedioxybenzene is 5.75 μg / cm 2, 6.50 μg / cm 2, and Benzyl benzoate is 10.03 μg / cm 2, 9.58 μg / cm 2, 1-aryl-3,4-methylene Deoxybenzene 10.50 μg / cm 2, 14.50 μg / cm 2, 3,4-methylenedioxybenzene 18.64 μg / cm 2, 14.60 μg / cm 2 and tick killer showed 90.15 μg / cm 2 and 87.38 μg / cm 2, respectively. It was.
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| KR20220079513A (en) | 2019-12-09 | 2022-06-13 | 판게아 메이드 인크. | laminate |
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