KR20110044818A - Composition for controlling plant diseases which comprises polyacetylenic acids or Prunella vulgaris L. extract containing them, and method for controlling plant diseases using the same - Google Patents

Abstract

PURPOSE: A composition containing Prunella vulgaris L. extract for preventing plant diseases is provided to prevent plant diseases without environmental pollution. CONSTITUTION: A composition for preventing plant diseases contains a compound of chemical formula 1 or 2 as an active ingredient. The compound is isolated from Prunella vulgaris L. The Prunella vulgaris L. extract is isolated using low alcohol of 1-7 carbon atoms, solution thereof, hexane, acetone, ethyl acetate, methylene chloride, or mixture thereof. The plant diseases are tomato late blight, mill red rust, or red pepper epidemic or sheath blight.

Description

Composition for controlling plant diseases which comprises polyacetylenic acids or Prunella vulgaris L. extract containing them, and method for controlling plant diseases using the same}

The present invention relates to a polyacetylenic acid compound isolated from Prunella vulgaris L. and to an environmentally friendly plant disease control composition containing the same as an active ingredient.

Since the 1960s, agriculture has faced the urgent task of securing food due to exponentially increasing population, and as a way to solve this problem, steadily increasing food production by using pests, weed control technology, breeding, and improving soil fertility. come. Among them, synthetic pesticides have become an indispensable factor in increasing agricultural production and have increased the use of synthetic pesticides as one of the solutions to increase yields. However, synthetic pesticides have contributed much to humankind through increased yields. However, side effects such as toxicity, environmental pollution and adverse effects of natural ecosystems, resistance to drugs, and resistance to chemicals caused by excessive use of synthetic pesticides can affect soil, rivers, and groundwater. Pollution has resulted in the destruction of environmental ecosystems. The residual toxicity and pesticide poisoning of agricultural products have a direct adverse effect on human health.

In order to solve the above problems, the development of low toxicity pesticides, low residual pesticides, and pesticides that are not harmful to natural enemies is being rushed, while many researchers are actively researching biological pesticides.

In Korea, biopesticides include microbial and biochemical pesticides. Biopesticides prevent pests by using substances derived from animals, plants, microorganisms, and natural products. Unlike chemical pesticides, biopesticides can produce high value-added agricultural products because they are safe for human beings and ecosystems. Instead, it is possible to increase the production of safe crops and to solve the problems caused by misuse of synthetic pesticides.

However, in Korea, there are many microbial pesticides registered and researched on microbial pesticides, but biochemical pesticides using natural products have not yet registered biochemical fungicides even though registration regulations were established in 2005.

Prunellae Herba is a perennial Prunella belonging to Labiatae. vulgaris L. Above ground outpost. The main components of the vinegar are triterpenoid, saponin, ursolic acid, hyperoxide, tannin and caffeic acid, rutin, alkaloid, vitamin B1, vitamin C, vitamin It contains K and potassium salts. Its medicinal effects are known to be effective in interpolation, purulent mastitis, breast cancer, diuresis, cough, hemostasis, mental anxiety, and nominal.

In addition, the physiological activity of the hyacinth has been reported for anti-HIV activity, anti-inflammatory activity, anti-allergic activity, anti-HSV activity, anti-mutant activity, and polysaccharide simple herpes virus (herpes simplex virus) isolated from the Although activity against type and type 2 is known, antifungal activity against plant diseases has not been reported yet.

Accordingly, the present inventors have tried to develop a natural fungicide that is harmless to the human body and is environmentally friendly. As a result, the vinegar extract and the polyacetylenic acid compound isolated therefrom exhibited high control against various plant diseases, The present invention was completed by confirming that it can be used as a natural product disinfectant for bottle control.

An object of the present invention is to provide an environmentally friendly plant disease control composition derived from natural products that is harmless to the human body and exhibits excellent control against various plant diseases such as rice blast, tomato late blight or pepper anthrax without causing environmental pollution. .

An object of the present invention is to provide a method for controlling plant diseases using the composition for controlling the above.

In order to achieve the above object, the present invention provides a composition for controlling plant diseases containing at least one compound selected from the compound of formula 1 and the compound of formula 2 as an active ingredient.

In addition, the present invention provides a method for controlling various plant diseases by treating the control composition to crops or soil.

Hereinafter, the present invention will be described in detail.

The present invention is derived from natural products, harmless to the human body and does not cause environmental pollution, and contains as an active ingredient one or more compounds selected from the compounds of the formula (1) and the compound of the formula (2) exhibiting high control against various plant diseases It provides a composition for controlling plant diseases.

Plant extract used in the present invention is a Prunella ( Prunella) to produce a control active ingredient of the compound of Formula 1 and Formula 2 vulgaris L.), and the vinegar extract ( Prunella vulgaris L.) is characterized in that it is extracted using a solvent selected from the group consisting of lower alcohols having 1 to 7 carbon atoms and aqueous solutions thereof, hexane, acetone, ethyl acetate, methylene chloride and mixtures thereof.

As a specific example, methanol was added to 3 kg of ultra dry samples, and the methanol extract obtained by extracting at room temperature for 1 day was filtered using a filter paper, and then the methanol extract obtained by concentrating the filtrate under reduced pressure was further extracted with another organic solvent. Obtain an organic solvent extract. In the present invention, it is also possible to perform the fractionation process commonly used in the art.

The compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 according to the present invention may preferably be separated, purified or chemically synthesized from Prunella vulgaris L ..

Specifically, the compounds represented by Chemical Formulas 1 and 2 according to the present invention are Prunella vulgaris L.) can be prepared by a method comprising the step of separating and purifying the organic solvent extract by column chromatography, wherein the usable columns include silica gel column, C ₁₈ column or Sephadex column, etc. An organic solvent such as hexane, ethyl acetate, methylene chloride, acetone, lower alcohol, etc. may be used. See FIG. 1.

In a preferred embodiment of the present invention, the dried vinegar is extracted with methanol and concentrated under reduced pressure, the methanol extract obtained by dissolving in 70% methanol and then extracted with the same amount of n -hexane and concentrated under reduced pressure, concentrated n -hexane layer Separation and purification of a repetitive silica gel column, a C ₁₈ column, or a Sephadex column by separation HPLC to purely separate octadeca-9,11,13-triynoic acid and trans -octadec-13-ene-9,11-diynoic acid do.

The composition for controlling plant diseases containing at least one compound selected from the compound of Formula 1 and the compound of Formula 2 according to the present invention as rice active, tomato blight, tomato blight, wheat red rust, pepper anthrax, pepper blight and rice It is characterized by controlling any one or more selected from leaf blight blight.

Specifically, the compounds of the formula (1) and the compound of the formula (2) according to the present invention was tested for the control activity against a total of four plant diseases, such as rice blast, tomato blight, wheat red rust and pepper anthrax, the compound of formula (1) And all compounds of Formula 2 showed high activity against rice blast, tomato late blight and pepper anthrax, in In vitro , in addition to the three phytopathogenic pathogens effectively inhibited the mycelial growth of rice leaf blight blight and pepper blight bacteria. See Tables 4-6.

Therefore, the composition containing the compound of Formula 1 and at least one compound selected from the compound of Formula 2 as an active ingredient is harmless to humans and does not cause environmental pollution, rice blast, tomato blight, wheat red rust, pepper anthrax, It can be usefully used as a natural fungicide showing excellent control against rice leaf blight blight and pepper blight.

The control composition of the present invention may further include a substance contained in a commonly used insecticide or fungicide, and in addition to the active ingredient, a pharmaceutically acceptable solid carrier, liquid carrier, liquid diluent, liquefied gas diluent as an excipient , Solid diluents, or other suitable auxiliaries such as emulsifiers, dispersants or foaming agents. The composition for controlling the active ingredient and the excipients may be formulated into various formulations known in the pesticide field. For formulation, any formulation method commonly used in the pesticide field may be used.

The control composition of the present invention may preferably be formulated in a hydrated, granulated, powdered, emulsified, sprayed, smokescreen, capsule and gelled formulation and contacted through a formulation such as a donut for buoyancy of the formulation. Preferably provided as.

In order to effectively control rice blast, tomato late blight and red pepper anthrax, the composition for controlling the present invention comprises a vinegar extract at a concentration of 50 to 2,000 ㎍ / ml in the composition for controlling plant diseases, and is an active ingredient of the present invention. The compound of Formula 1 and at least one compound selected from the compound of Formula 2 is preferably included in the composition for controlling plant diseases at a concentration of 50 to 1,000 ㎍ / ㎖, which is the type of crop, the degree of growth, the environment of cropland, plant diseases It can be appropriately adjusted in consideration of the degree of onset.

By treating the control composition of the present invention formulated as described above to plants or areas that require control, rice blast, tomato late blight, wheat red rust, pepper blight and pepper anthrax can be controlled. The preferred method is to apply the control composition so as to be in direct contact with the plant pathogens to control, the most preferred is a method of mixing the soil or spraying directly to the crop.

According to the present invention, the composition for control of the present invention using the extract of Hagocho as an active ingredient is derived from natural products and is harmless to the human body without causing environmental pollution, rice blast, tomato late blight, wheat red rust, chill blight and chill anthrax. Since it exhibits control activity against plant fungal diseases, it can be useful for the development of environmentally friendly natural product disinfectants and for the production of high value-added organic products.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

[ Example  One] Hagocho  Extract In plant diseases  Control activity

Extracts, Fractions and Isolated Materials of Magnaporthe grisea ), Rhizoctonia solani ), tomato gray mold ( Botrytis cinerea ), barley powdery mildew ( Erysiphe graminis f. sp. hordei ), tomato plague ( Phytophthora infestans ), wheat rust ( Puccinia recondita ) and pepper anthrax ( Colletotrichum) coccodes ) for seven plant diseases in In vivo antimicrobial activity was investigated. Each material was dissolved in methanol (final concentration, 5%) and then diluted in distilled water containing surfactant Tween 20 at a level of 250 μg / ml. At this time, the control group was used distilled water containing 5% methanol and 250 μg / ㎖ Tween 20. Two pots were used for each plant disease, and the active ingredient samples were spray-sprayed on the foliar and air-dried for 24 hours before inoculating each plant pathogen.

Rice, tomatoes, barley and wheat used in the experiment were filled with water or clay for horticulture 70% in plastic pots with a diameter of 4.5 cm, and then seeded and grown in a greenhouse at 25 ± 5 ℃ for 1 to 4 weeks.

Rice blasts are sprayed with 3-4 leaf seedlings inoculated with a spore suspension (5 × 10 ⁵ spores / ml) of Magnaporthe grisea (Korea Research Institute of Chemical Technology), the causative agent of blast disease, and sprayed at 25 ° C. per day. After the wet treatment, the incubation was induced by incubation for 5 days in a constant temperature room at 25 ℃.

Rice leaf blight is Rhizoctonia , a causative agent of leaf blight. solani (Korea Research Institute of Chemical Technology) was incubated for 7 days in a medium (90 g of wheat bran, 15 g of chaff and 100 ml of distilled water), inoculated into 5 leaf seedlings and wet-treated in a humidified environment at 25 ° C. for 4 days. Incubation was induced by incubation in a constant temperature room at 25 ° C. for 4 days.

Tomato late blight was sprayed with 2 to 3 leaf tomato seedlings inoculated with the suspension of the distilled sap from the juvenile sac (3 × 10 ⁴ sporangia / ml) of Phytophthora infestans (Gangneung University), the causative agent of late blight . The treatment was induced for 2 days in a wet room and incubated in a constant temperature and humidity room at 25 ° C. for 1 day.

Tomato gray mold disease was treated with spore suspension (10 ⁶ spores / ml) of Botrytis cinerea (Korea Research Institute of Chemical Technology), a causative agent of gray mold disease, in tomato seedlings of 2-3 leaves. In fact, 3 days incubation was induced to induce.

Wheat rust is sprayed by suspending spores of Puccinia recondita (University of Incheon), the causative agent of rust, known as biolactic bacteria, in a single-leaf seedling, suspended in an amount of 0.67 g spores / ℓ, a 250 µg / ml Tween 20 solution. After treatment for one day in a 20 ℃ humid room and transferred to a 20 ℃ constant temperature room was incubated for 6 days to induce the onset.

Barley powdery mildew ( Erysiphe ) is the causative agent of powdery mildew, which is passaged from host plants to seedlings of barley. graminis f. sp. hordei (Korea Research Institute of Chemical Technology) spores were inoculated and inoculated and cultured in a constant temperature room at 20 ° C for 7 days to induce the onset. After 5 days of inoculation of rice blast, 7 days of inoculation of wheat rust and wheat powdery mildew, 8 days of inoculation of rice leaf blight, and 3 days of inoculation of tomato ash and tomato late blight were investigated.

On the other hand, for the control activity test for pepper anthracnose, 70% of horticultural soil is filled in a plastic pot with a diameter of 7.0 cm, sowing seeds, growing them in a greenhouse to 3 to 4 leaves, and then prepared methanol extract of Hagocho prepared above. Samples were foliarly sprayed. After spraying the sample, dried at room temperature for 24 hours and then Colletotrichum ( choletotrichum) spore suspension (4 × 10 ⁵ spores / ml) of coccodes , Korea University). After 2 days of invasion in a humid room, it was left in a constant temperature room at 25 ° C. for 1 day, and the lesion area ratio was examined after 3 days of inoculation.

Using the lesion area ratio obtained from the above, the control value was calculated according to the following equation.

As shown in Table 1, the methanol extract of Hagocho showed high control activity against rice blast, tomato blight, wheat red rust and pepper anthrax among seven plant diseases.

Example 2 Isolation and Purification of Antimicrobial Substances

7 L of methanol was added to 3 kg of a high ultrahigh dry sample, and the methanol extract obtained by extracting at room temperature for 1 day was filtered using filter paper, and the filtrate was concentrated under reduced pressure. The ethanol methanol extract was dissolved in 2 L of 70% methanol, extracted twice with the same amount of n-hexane, and the hexane layer and the aqueous layer were concentrated under reduced pressure. The concentrated aqueous layer was again dissolved in 2 L of distilled water and extracted twice with the same amount of ethyl acetate and butanol. The three organic solvent extracts and the aqueous solution layer obtained above were concentrated under reduced pressure, and the control activities for the seven plant diseases were investigated in the same manner as in Example 1.

As a result, as shown in Table 2, the n -hexane (hexane) layer showed the highest overall control activity against the seven plant diseases, the hexane layer was used for the separation and purification of the active control component separately.

Silica gel column chromatography (3 × 60 cm, using n -hexane layer: acetone mixture (9: 1, v / v) as a developing solvent to separate the active ingredient from the n -hexane layer (25 g), Kiesel gel 60, 70-230 mesh, 400 g: Merck). The eluate obtained therefrom was separated and analyzed by thin layer chromatography (TLC: Kiesel gel 60 F254, 0.25 mm; Merck). Depending on the pattern of TLC, divided into nine fractions, and three fractions of F1 to F3 having similar activities and having the same Rf value were again developed with a chloroform: methanol mixture (97: 3, v / v). Silica gel column chromatography (2 × 40 cm, Kiesel gel 60, 230-400 mesh, 50 g: Merck) was analyzed and divided into seven fractions. Among them, F57 was subjected to Sephadex LH-20 column chromatography using methylene chloride: n -hexane: methanol (5: 5: 1, v / v / v) as a developing solvent, and HPLC was performed for separation. Is as follows.

The column is Capcell Pak C ₁₈ (20 mm × 250 mm), acetonitrile gradient system with distilled water-0.1% trifluoroacetic acid as eluent, flow rate 10 ml / min, detection wavelength 210 nm and 254 nm. Under the conditions, substance 1 eluted between 42.2 and 42.8 minutes, substance 2 was eluted between 43.2 and 43.8 minutes, and the eluate was concentrated under reduced pressure to separate substance 1 (60 mg) and substance 2 (120 mg).

In order to investigate the purity of the separated material, the column is Cosmosil C ₁₈ (2) (150 mm × 4.6 mm), the acetonitrile gradient system with distilled water -0.1% trifluoroacetic acid as the eluent, the flow rate is 1 ml. The injection amount was 10 μl / min and the detection wavelength was analyzed by HPLC under the conditions of 210 nm and 254 nm.

[ Example  3] Determination of structure of antimicrobial substance

In order to identify the structures of the two active substances isolated in Example 2, mass spectrometry and nuclear magnetic resonance analysis were performed. In substance 1, the molecular ion peak was observed at m / z 272 in the EI-MS spectrum, and the main segment ion was found at m / z 244, 230, 199, 185, 169, 157, and 141 (base peak).

(One) octadeca -9,11,13- triynoic acid Structure determination (substance 1)

¹³ C-NMR, ¹ H-NMR, DEPT135 ^o , HSQC, ¹ H- ¹ H COSY and HMBC analysis were performed to determine the exact structure of material 1. ^{In 13} C-NMR and DEPT135 ^o , six quaternary carbon signals were observed at d 60.8, d 60.9, d 66.2, d 66.2, d 80.1 and d 80.1. In addition, 10 methylene carbon signals were observed at d 19.5, d 19.7, d 22.9, d 26.0, d 29.1, d 29.7, d 29.8, d 30.0, d 31.3, and d 34.8, and one carboxyl carbon signal and d at 177.7. In 13.8 the presence of terminal methyl group carbon was confirmed. Were determined for each of the hydrogen attached to the carbon via a HSQC, it could be connected to a partial structure a partial structure for the ¹ H- ¹ H COSY through a determined lower limit, and then, finally HMBC. Thus, NMR data of the material 1 is shown in Table 3.

As can be seen in Table 3 below, substance 1 was determined as 18 octadeca-9,11,13-triynoic acid having three triple bonds and one carboxyl group, which was Kanokmedhakul et al. (2007: Bioactive constituents of the roots of Polyalthia cerasoides , J. Nat . Prod . 70: 1536-1538). Kanokmedhakul (2007) reported that octadeca-9,11,13-triynoic acid exhibits antimalarial and antimycobacterial activity. However, activity against microorganisms such as fungi has not been reported yet.

(2) trans - octadec -13- ene -9,11- diynoic acid Structure determination (substance 2)

Molecular ion peaks were observed in m / z 274 in the EI-MS spectrum of substance 2, and the major segment ions were m / z 245, 231, 217, 201, 187, 164, 145, 129, 115 (base peak) Etc. were observed. ¹³ C-NMR, ¹ H-NMR, DEPT135 ^o , HSQC, ¹ H- ¹ H COZY and HMBC analysis were performed to determine the exact structure of material 2. Four quaternary carbon signals were observed at d 66.2, d 73.6, d 74.6 and d 83.9 at ¹³ C-NMR and DEPT135 ^o , and double bonds were observed at d 109.7 and d 149.0. . In addition, 10 methylene carbon signals were observed at d 19.7, d 23.2, d 25.9, d 29.4, d 29.7, d 29.8, d 30.0, d 31.9, d 33.8, d 34.9, and one carboxyl carbon signal and d at 177.7. In 14.1 the presence of terminal methyl group carbon was confirmed. Through the HSQC was determined the hydrogen attached to each carbon, it was determined the partial structure for the ¹ H- ¹ H COSY, could finally connect the parts structure for the HMBC. Thus, NMR data of the material 2 is shown in Table 3 below.

As can be seen in Table 3 below, substance 2 was determined to be 18 carbon trans -octadec-13-ene-9,11-diynoic acid having two triple bonds, one double bond and one carboxyl group. It was found to be consistent with the substances reported by Jaber et al. (2003). There is no report on the biological activity of this substance, and the first reported reports of antimicrobial activity.

Example 4 Antimicrobial Activity of Phytopathogens of Substances Isolated from Prunella vulgaris

The inhibitory effect of mycelial growth on various phytopathogenic fungi of the substances isolated and identified in Example 3 was investigated. Each material was dissolved in dimethyl sulfoxide (DMSO) at a level of 0.084, 0.25, 0.76, 2.3, 6.7, 20 / and used in the experiment. Rice Blight Bacteria (Magnaporthe grisea), Rice leaf blightRhizoctonia solani), Tomato late blight (Phytophthora infestans), Tomato gray mold fungus (Botrytis cinerea), Persimmon anthrax (Colletotrichum gloeosporioides), Radish germ (Fusarium oxysporumf. sp.raphani), Cucumber bacteriaSclerotinia sclerotiorum), Pepper blight (Phytophthora capsiciGrowth inhibitory activity against 8 phytopathogenic fungi, etc. was investigated. As a test medium, tomato blight was used as V8 juice medium, and the remaining pathogens were PDB (potato dextrose broth) medium. The rice blast bacteria, tomato gray fungus bacteria, persimmon anthrax bacteria and radish gastric bacterium harvest spores from solid medium to obtain 1 × 10⁴ Spoons / ml were dispensed in 1 ml aliquots in 48-well plates. Rice leaf herbaceous fungus and cucumber fungal nucleus were cultured in PDB medium for 7 seconds with a blender, and then pulverized for 10 seconds. A suspension prepared by inoculating 1% in sterile PDB medium was dispensed in a 1-mL 48-well plate. Tomato blight and pepper blight are harvested and stored refrigerated for 1 hour, then germinate the sprouts to increase the number of strains.⁴ Dispense at spores / ml. The two materials dissolved in DMSO were finally treated to levels 0.84, 2.5, 7,6, 23, 67, and 200 μg / ml. The untreated section was treated with 10 DMSO per well.

The experiment was repeated three times per treatment concentration, and the inoculated well plate was expressed as minimum inhibitory concentration (MIC) after 25 to 3 days incubation.

As confirmed in Table 4, the two types of substances isolated and identified in Example 3 showed high antimicrobial activity against rice blast bacterium, rice leaf blight, tomato blight, and pepper blight, respectively. The bacterium showed a slightly lower inhibitory effect.

[ Example  5] From hagocho  Antibacterial Activity of Phytopathogenic Bacteria from Isolated Substances

The inhibitory effect on the growth of various phytopathogenic bacteria was investigated for the substances isolated and identified in Example 3. The two kinds of materials were dissolved in dimethyl sulfoxide (DMSO) at 0.084, 0.25, 0.76, 2.3, 6.7, and 20 mg / ml, respectively, and then used in the experiment.

Acidovorax konjaci ), Agrobacterium tumefaciens , Burkholderia glumae ), Pectobacterium carotovora subsp . carotovora ), Pseudomonas bacillus syringae pv . lachrymans ), red pepper bacterium ( Xanthomonas) euvesicatoria ) The growth inhibitory activity of the six phytopathogenic bacteria was investigated using 96-well platite. All bacteria were inoculated in nutrient broth (NB), incubated at 30, and then adjusted to 10 ⁴ cells / mL using 0.9% sterile NaCl solution, followed by 1.5 μl of 150 μl NB medium. The wells were inoculated. Three materials dissolved in DMSO were finally treated to 0.84, 2.5, 7,6, 23, 67, and 200 μg / ml levels. The untreated section was treated with 1 DMSO per well. The experiment was repeated three times for each concentration, and inoculated well plates were incubated at 30 to 1 to 4 days. Turbidity was determined at 600 nm after incubation, and compared to the mulberry. The results were expressed as minimum inhibitory concentrations (MICs).

As confirmed in Table 5, the two types of substances isolated and identified in Example 3 showed a weak antibacterial activity with a minimum growth inhibitory concentration value of 200 µg / ml only for red pepper beetle bacteria, but no other bacteria at all. There was no activity.

[ Example  6] From hagocho  Of the separated substances In plant diseases  Control activity

Example 3 is separated from the second extract and the materials of the two kinds of identification that is, octadeca-9,11,13-triynoic acid, and trans -octadec-13-ene-9,11 -diynoic acid in vivo (in vivo In order to investigate the bactericidal activity, four plant diseases, such as rice blast, tomato late blight, wheat red rust and pepper anthrax, were tested as follows.

After dissolving the two kinds of substances identified from the above Hagocho extract in methanol, respectively, the final concentration was adjusted to 150, 250, 500 µg / ml by adding 250 µg / ml Tween 20 solution, and the final methanol concentration of all samples. Set to 5%. At this time, a solution containing 5% methanol and 250 μg / ml Tween 20 was used as a control. Two pots were used for each plant disease, and the active ingredient samples were spray-sprayed on the foliar and air-dried for 24 hours before inoculating each plant pathogen. Control activities against the four plant diseases were investigated according to the method described in Example 1, and the results are shown in Table 6 below.

As can be seen in Table 6 and Figures 2 to 4, the two types of substances isolated and identified from Hagocho extract in Example 3 showed an excellent control effect against rice blast, tomato blight and pepper anthrax. Octadeca-9,11,13-triynoic acid showed 87%, 86%, 93% control effect on rice blast, tomato late blight and red pepper anthrax when treated at a concentration of 500 ㎍ / ㎖, and the concentration of 250 ㎍ / ㎖ When treated with, it showed effects of 63%, 75% and 96%, respectively. In addition, the treatment of rice blast and pepper anthrax showed high control effects of 80% and 82%, respectively.

In addition, trans -Octadec-13-ene-9,11-diynoic acid also showed high activity against rice blast, tomato late blight and pepper anthrax, and had an activity spectrum similar to that of octadeca-9,11,13-triynoic acid. It was confirmed.

Figure 1 is a schematic of the separation and purification of the active ingredient from the haechocho extract according to the present invention,

Figure 2 is a view showing the control effect against rice blast of the active ingredient isolated from the edible extract according to the present invention,

(a: Octadeca-9,11,13-triynoic acid, b: trans -Octadec-13-ene-9,11-diynoic acid, CK: untreated, 150, 250 and 500 μg / ml, Ba: Blasticidin-S 50 Μg / ml)

Figure 3 is a view showing the control effect against the late blight of tomato control active ingredient isolated from Haechocho extract according to the present invention,

(a: Octadeca-9,11,13-triynoic acid, b: trans -Octadec-13-ene-9,11-diynoic acid, CK: untreated, 150, 250 and 500 μg / ml, Flu: Fludioxonil 50 μg / Ml)

Figure 4 is a view showing the control effect on the pepper anthrax of the control active ingredient isolated from the extract of Hagocho according to the present invention.

(a: Octadeca-9,11,13-triynoic acid, b: trans -Octadec-13-ene-9,11-diynoic acid, CK: untreated, 500, 250 and 150 μg / ml, Di: Dithianon 50 μg / Ml).

Claims (6)

A composition for controlling plant diseases, which contains at least one compound selected from a compound of Formula 1 and a compound of Formula 2 as an active ingredient.

The method of claim 1, The compound of Formula 1 and the compound of Formula 2 is a composition for controlling plant diseases, characterized in that extracted from Prunella vulgaris L .. 3. The method of claim 2, Prunella extract ( Prunella) vulgaris L.) is a composition for controlling plant diseases, characterized in that extracted using a solvent selected from the group consisting of lower alcohols having 1 to 7 carbon atoms and an aqueous solution thereof, hexane, acetone, ethyl acetate, methylene chloride and mixtures thereof . The method of claim 1, The active ingredient is a composition for controlling plant diseases, characterized in that contained in a concentration of 50 to 1,000 ㎍ / ㎖ relative to the composition for controlling plant diseases. The method of claim 1, The plant disease is a plant disease control composition, characterized in that at least one selected from rice blast, tomato blight, wheat red rust, pepper anthrax, pepper blight and rice leaf blight blight. A method of controlling plant diseases, comprising treating the crop or soil with the composition for controlling plant diseases according to any one of claims 1 to 5.

Images