KR101466615B1 - COMPOSITION FOR CONTROLLING PLANT DISEASES COMPRISING AN EXTRACT OF Loeseneriella cambodiana OR ACTIVE COMPONENT ISOLATED THEREFROM, AND METHOD FOR CONTROLLING PLANT DISEASES USING THE SAME - Google Patents

Abstract

Loeseneriella The present invention relates to a composition for controlling plant diseases, comprising a cambodiana extract or a lactam-based compound separated therefrom as an active ingredient, and a method for controlling plant diseases using the same. And exhibits high control activity against various plant diseases without inducing environmental pollution. Therefore, it can be useful for the development of environmentally friendly natural disinfectant and production of high value added organic agricultural products.

Description

FIELD OF THE INVENTION The present invention relates to a composition for controlling plant diseases, comprising a Loeseneriella cambodiana extract or an active ingredient isolated therefrom, and a method for controlling plant diseases using the same. BACKGROUND ART THE SAME}

The present invention relates to a composition for controlling plant diseases, comprising an extract of Loeseneriella cambodiana or an active ingredient isolated therefrom, and a method for controlling plant diseases using the same.

Humans have long been using synthetic pesticides as a way to protect crops from harmful organisms and have been able to increase yields by increasing the use of synthetic pesticides. However, due to the use of excessive synthetic pesticides, side effects such as adverse effects of toxicity, environmental pollution and natural ecosystem, tolerance to chemicals and resistance appeared, resulting in destruction of environmental ecosystem by polluting not only soil and river but also groundwater . In addition, some synthetic pesticides are estimated to be environmental hormones and are recognized as one of the major causes of ecosystem disturbance, so efforts to develop natural products to replace synthetic pesticides are increasing.

Biopesticides in Korea include microbial pesticides and biochemical pesticides. Biological pesticides are used to prevent pests by using substances derived from animals, plants, microorganisms, and natural products. Unlike chemical pesticides, they are safe for manure and ecosystem and produce agricultural products with high added value. In Korea, there are many microbial pesticides registered in the center of microbial pesticides. However, in case of biochemical pesticides using natural materials, there is no registered biochemical disinfectant even though registration regulations were established in 2005.

Milsana ( ^TM ) is one of the most popular disinfectant products on the market worldwide. This product is an eco-friendly disinfectant developed by using extract of Reynouria sachalinensis . It is known that it shows resistance to powdery mildew by inducing resistance to plants rather than direct lethal effects of plant pathogens. In addition, the cinnamaldehyde component, which is registered as a natural product fungicide, is extracted from the seeds of Cassia tora and has not only insecticidal activity, but also belongs to the genus Verticillium , Rhizoctonia , Pythium ) and fusarium mononitum var. Have been reported to have bactericidal activity against plant pathogens such as Fusarium moniliforme var. Subglutinans (canker disease: canker disease). Also, jojoba oil extracted from Jojoba ( Simmondsia califormica ) seeds has a fungicidal activity against powdery mildew as well as insecticidal activity. The Macleaya genus extract is an extract of Macleaya cordata . It is effective against mildew disease, Alternaria spp., And Septoria leaf spots. In addition, fatty acids containing oleic acid as a main component are also effective for powdery mildew.

Natural products are broad concepts that include plants, microorganisms and their metabolites in nature. Currently, plant resources are used not only as food and medicine but also as natural material disinfectant materials. In addition to medicines using plant materials, they also play an important role in the development of environmentally friendly pesticides. Therefore, if a new material is developed by searching for the active substance contained in the plant, the use value of the natural material fungicide may be further increased.

Accordingly, the present inventors have studied antibacterial activity from rare plant species native to Vietnam and searched for the development of natural materials. As a result, Loeseneriella cambodiana extract and the compounds isolated therefrom exhibited high controlling activity against various plant diseases To complete the present invention.

Accordingly, an object of the present invention is to provide an environmentally friendly plant disease controlling composition derived from a natural product, which is harmless to the human body and exhibits excellent controlling activity against various plant diseases without causing environmental pollution.

Another object of the present invention is to provide a method for controlling plant diseases using the plant disease control composition.

In order to achieve the above object, the present invention provides a composition for controlling plant diseases, which comprises a compound represented by the following general formulas (1) to (3) or a mixture thereof as an active ingredient.

[Chemical Formula 1]

(2)

(3)

The present invention also provides a composition for controlling plant diseases, which contains Loeseneriella cambodiana extract as an active ingredient.

In order to accomplish the above object, the present invention provides a method for controlling a plant disease by treating the composition for controlling a crop or soil.

The composition for controlling plant diseases according to the present invention is a plant derived from a natural product and is harmless to the human body and does not cause environmental pollution, and can be used for a variety of plants such as rice blast, rice sheath blight, tomato gray mold, tomato blight, It exhibits excellent controlling activity against fungal diseases, so it can be usefully used for the development of environmentally friendly natural material fungicide and production of high value-added organic agricultural products.

Figure 1 is a schematic illustration of the process of isolating and purifying the active ingredient from Loeseneriella cambodiana .
2 to 5 show EI-MS, GC-MS, < ¹ > H-NMR and ¹³ -diaza-cyclohexacosane- C-NMR, respectively.
6 and 7 1,14,27- triaza-bicyclo na tree Archon shots of -2,15,28- tree on (1,14,27-triazacyclononatricontane-2,15,28-trione ) EI-MS and ¹ ≪ 1 > H-NMR.
Figs. 8 and 9 show the control effects of 20% water- soluble agent prepared from Loeseneriella cambodiana extract against barley powdery mildew and wheat rust.

Hereinafter, the present invention will be described in detail.

The present invention provides a composition for controlling plant diseases, which comprises a compound represented by the general formulas (1) to (3) or a mixture thereof as an active ingredient.

The present invention also provides a composition for controlling plant diseases, which contains Loeseneriella cambodiana extract as an active ingredient.

The composition for controlling plant diseases according to the present invention is derived from a natural product and is harmless to the human body and does not cause environmental pollution, and exhibits high controlling activity against various plant diseases.

In the present invention, the plant disease is not limited to the rice blast, rice sheath blight, tomato gray mold, tomato blight, wheat red rust, barley powdery mildew, red pepper anthracnose, anthrax anthracis, ≪ / RTI > and combinations thereof.

In the present invention, the Loeseneriella cambodiana extract can be prepared by extracting the dried product of Loeseneriella cambodiana with an organic solvent, wherein the organic solvent is selected from the group consisting of C _1-7 lower alcohol or an aqueous solution thereof, hexane, ethyl acetate, methylene chloride, Can be used. Methanol can be preferably used.

In the present invention, for example, Loeseneriella cambodiana a extract is prepared by adding 1 L of methanol to 300 g of a dried sample of Loeseneriella cambodiana , filtering the methanol extract obtained at room temperature for 1 day using a filter paper, and concentrating it under reduced pressure to obtain a methanol extract , An organic solvent extract can be obtained by further extracting the methanol extract obtained above with another organic solvent. In the present invention, a fractionation process commonly used in the art may be performed.

In the present invention, 1,14-diazacyclohexacosane-2,15-dione represented by the general formula (2) is separated and purified from the organic solvent extract of Loeseneriella cambodiana by column chromatography Or may be obtained by purification. At this time, usable columns include a silica gel column, a C ₁₈ column or a sephadex column, and an organic solvent such as hexane, ethyl acetate, methylene chloride, acetone, C _1-7 lower alcohol and the like can be used.

According to one embodiment of the present invention, the dried product of Loeseneriella cambodiana is extracted with methanol, and the methanol extract obtained by concentration under reduced pressure is dissolved in 70% methanol, extracted with the same amount of n -hexane and concentrated under reduced pressure. Then, by separating and purifying the concentrated n -hexane layer by repeated HPLC with a silica gel column, C ₁₈ column or Sephadex column, 1,14-diazacyclohexaoxan-2,15-dione was extracted from Loeseneriella cambodiana extract (See FIG. 1).

Also, the 1,14-diazacyclohexacosane-2,15-dione is described in Gerald F. Koser, J. Org. Chem ., 43, 4393-4394, (1978)].

In the present invention, 1-aza-2-cyclotridecanone represented by the formula (1) and 1,14,27-triazacyclononatriacontan-2 represented by the formula (3) , And 15,28-trione (1,14,27-triazacyclononatricontane-2,15,28-trione) can be prepared by reacting a monomer and a trimer in the process of preparing the compound of Formula (2) . ≪ / RTI >

According to the present invention, the methanol extract of Loeseneriella cambodiana , or the compounds of the formulas (1) to (3), or a mixture thereof, can be used for the treatment of rice blast, rice sheath blight, tomato gray mold, tomato plague, wheat red rust, barley powdery mildew, It can exhibit the controlling activity against botanical diseases such as anthrax, bacterium, cucumber, and pepper. Therefore, the composition for controlling botanical disease which contains it as an active ingredient is a natural product which is harmless to the human body and does not cause environmental pollution It can be used effectively as a bactericide.

According to one embodiment of the present invention, the compounds of the general formulas (1) to (3) exhibit antifungal activity commonly against rice blast fungus and pepper anthracnose, and the compounds of general formulas (1) and (2) (See Table 5).

The composition for controlling plant diseases according to the present invention may further contain, in addition to the active ingredient, a substance contained in an insecticide or a bactericide commonly used in the art.

The composition for controlling plant diseases according to the present invention may be formulated into various formulations known in the field of agrochemicals, and any formulating method conventionally used in the field of agrochemicals may be used for formulation.

The plant disease controlling composition of the present invention can be formulated into a formulation preferably in the form of a wettable powder, a granule, a powder, an oil, a spray, a film, a capsule or a gel, It is preferably provided as a contact agent. In the present invention, it can be used in the form of a wetting agent, preferably a 20% wetting agent.

The composition for controlling plant diseases according to the present invention is useful for controlling diseases caused by diseases such as rice blast, rice sheath blight, tomato gray mold, tomato plague, wheat red rust, barley powdery mildew, pepper anthracnose, Persicaria anthracis, The composition of the present invention may contain Loeseneriella cambodiana extract as an active ingredient at a concentration of 50 to 3,000 占 퐂 / ml, preferably 500 to 1,000 占 퐂 / ml, The mixture may be contained at a concentration of 50 to 2,000 占 퐂 / ml, preferably 200 to 500 占 퐂 / ml, but it may be suitably adjusted in consideration of the kind of crop, the degree of growth, the cultivation environment, .

Further, the present invention provides a method for controlling a plant disease by treating the above composition for controlling a crop or soil.

The above method can be applied to a plant or an area where the plant disease control composition of the present invention is required to be treated in a plant or a region where the plant is required to be controlled, thereby preventing the occurrence of diseases such as rice blast, rice sheath blight, tomato gray mold, tomato blight, wheat blight, , Corynebacterium bacterium, cucumber sclerotinia, and pepper spp. Can be controlled. A preferred method is to apply the composition to direct contact with plant pathogens and to control them, and may be applied to the soil or directly sprayed on the crops.

[Example]

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

Example  One: Loeseneriella cambodiana  Extract In botanical bottles  Control activity against

Loeseneriella cambodiana extract of rice blast (Magnaporthe oryzae ), rice sheath blight ( Rhizoctonia solani ), tomato gray mold disease ( Botrytis cinerea), tomato late blight (Phytophthora infestans), wheat leaf rust (Puccinia recondita), wheat powdery mildew (Erysiphe graminis f. sp. hordei ) and red pepper anthracnose (7 kinds of in vivo (in a plant for the bottle of Colletotrichum coccodes) vivo) was investigated for the antimicrobial activity.

300 g of L. cambodiana (a Vietnamese native plant sample, Institute of Industrial Chemistry, Vietnam) was dissolved in 1 L of methanol (final concentration, 5%) and diluted in distilled water containing surfactant Tween 20 at 250 / / ml. At this time, distilled water containing 5% methanol and 250 占 퐂 / ml Tween 20 was used as the control. Two pots were used for each plant, and the prepared samples were sprayed on the leaf surface, air dried for 24 hours, and each plant pathogen was inoculated.

The rice, tomato, barley and wheat used in the experiment were filled with plastic pots with a diameter of 4.5 ㎝ in a volume of about 70% of the ground or horticultural soil, seeded and cultivated in a greenhouse at 25 ± 5 ℃ for 1 to 4 weeks.

The rice blast fungus is grown in the seedlings of 3 ~ 4th leaf stage by Magnaporthe oryzae, a spore suspension of the Korea Research Institute of Chemical ^{Technology) (5 × 10 5 spores /} ㎖) after spray inoculation, and seupsil processing for a day in a moist substance of 25 ℃ to, induce disease in 5 days incubation in thermostatic chamber of 25 ℃ .

Rhizoctonia solani ( Rhizoctonia solani , Korea Research Institute of Chemical Technology), which is a causative agent of sheath blight, was cultivated for 7 days in medium (90 g of bran, 15 g of rice hull and 100 ml of distilled water) The seedlings were inoculated, drought treated at 25 캜 for 4 days, and cultured in a constant temperature room at 25 캜 for 4 days to induce the disease.

The tomato gray mold was treated with a spore suspension (10 ⁶ spores / ml) of Botrytis cinerea (Korea Research Institute of Chemical Technology), a causative organism of gray mold, Actually, the onset was induced by culturing for 3 days.

Tomato blight was sprayed on tomato seedlings of 2 ~ 3 leaves after spraying of a suspension of kidney (3 × 10 ⁴ sporangia / ㎖) from Phytophthora infestans (Kangnung National University) On a wet condition for 2 days and cultured in a constant temperature and humidity room at 25 ° C for 1 day to induce onset.

Spore of Puccinia recondita (University of Incheon), a causative organ of rust, which is known as active parasitic organism, is suspended in 250 g / ml Tween 20 solution of 0.67 g spores / Treated in a wet condition at 20 ° C for one day, transferred to a constant temperature chamber at 20 ° C, and cultured for 6 days to induce the onset.

Barley powdery mildew was induced by inoculating the spores of Erysiphe graminis f. Sp. Hordei (Korea Research Institute of Chemical Technology), a causative organism of powdery mildew passaged in host plants, in a first seedling of barley , Lt; RTI ID = 0.0 > C < / RTI > for 7 days.

After 5 days of inoculation of rice blast, 7 days after inoculation of wheat red rust and barley powdery mildew, 8 days after inoculation of rice sheath blight, tomato gray mold and tomato blight were examined 3 days after inoculation.

In order to test the antiseptic activity against pepper anthracnose, a plastic pot with a diameter of 7.0 cm was filled with about 70% of the soil for horticulture, seeds were sown, and the seeds were cultivated in the greenhouse to 3-4 leaf stage. Then, the above-prepared Loeseneriella cambodiana The extract samples were sprayed on the leaves. After spraying the sample, it was dried at room temperature for 24 hours and sprayed with a spore suspension (4 × 10 ⁵ spores / ml) of Colletotrichum coccodes (Korea University), an anthrax ancestor of pepper. After 2 days of onset, it was allowed to stand in a constant temperature room at 25 ℃ for 1 day.

Using the percentage of lesion area obtained from the above, the control was calculated according to the following equation, and the results are shown in Table 1 below.

[Mathematical Expression]

sample Concentration (/ / ml) Control (%) Loeseneriella cambodiana methanol extract 1,000
RCB RSB TGM TLB WLR BPM PAN 29 100 94 98 67 25 0 RCB: rice blast; RSB: rice sheath blight; TGM: Tomato gray mold disease; TLB: tomato blight; WLR: wheat red rust; BPM: barley powdery mildew; PAN: pepper anthracnose

As shown in Table 1 above, Loeseneriella The methanol extracts of cambodiana showed more than 90% inhibitory activity against rice sheath blight, tomato gray mold and tomato blight.

Example  2: Separation and purification of antimicrobial substances

2-1: Loeseneriella cambodiana  Control activity of methanol extracts and fractions

The methanol extract of Loeseneriella cambodiana was purchased from the Korean plant extract bank of Daejeon Metropolitan City and used for the experiment. The same amount of the suspension was 25 g of the methanol extract of Loeseneriella cambodiana purchased from Korea plant extracts in methanol bank 1L n - hexane (n -hexane) was conducted by a fraction, the same amount of ethyl acetate to the remaining aqueous layer sample (ethyl acetate ) And butanol to obtain 370 mg of the n -hexane fraction, 260 mg of the ethyl acetate fraction, 590 mg of the butanol fraction and 780 mg of the water fraction, respectively.

The three organic solvent extracts and aqueous solution layers obtained above were concentrated under reduced pressure, and then the control activity against seven kinds of plant diseases was examined in the same manner as in Example 1, and the control values were calculated and the results are shown in Table 2 below .

sample Concentration (/ / ml) Control (%) RCB RSB TGM TLB WLR BPM PAN n -hexane layer 1,000 0 15 14 79 60 0 40 Ethyl acetate layer 1,000 98 100 98 90 93 72 30 Butanol layer 1,000 75 25 21 17 73 0 5 Aqueous solution layer 1,000 38 5 0 8 13 0 30 RCB: rice blast; RSB: rice sheath blight; TGM: Tomato gray mold disease;
TLB: tomato blight; WLR: wheat red rust; BPM: barley powdery mildew; PAN: pepper anthracnose

As a result, as shown in Table 2 above, the ethyl acetate fraction showed a high control effect against rice blast, rice sheath blight, tomato gray mold, tomato blight, wheat red rust and barley powdery mildew at the level of 1,000 ㎍ / . Therefore, it was found that the active substance was present in the ethyl acetate fraction, and the antimicrobial active substance was isolated and purified.

2-2: Isolation and purification of antimicrobial active substances

The active ingredient was separated from the ethyl acetate fraction (260 mg) prepared above using a mixture of methylene chloride: n -hexane: methanol (5: 5: 1, v / v / v) 20 column chromatography (1.5 cm column diameter × 80 cm column length, resin size 25-200 μm, resin weight 200 g, Sigma).

The eluate was fractionated and analyzed by thin layer chromatography (TLC: Kiesel gel 60 F254, 0.25 mm; Merck). The fractions were divided into five fractions according to the pattern of TLC. (2 x 90 cm, 25-200 [mu] m, 200 g; Sigma) in which 100% methanol was used as a developing solvent, and the same F2 fraction (120 mg) Lt; RTI ID = 0.0 > 5 < / RTI > fractions.

Among the five fractions, F23 (100 mg) was separated by preparative HPLC (HPLC), and the purity of the separated material was measured by HPLC analysis under the following conditions.

<HPLC Conditions>

Column: Luna 5 μC18 (2) 100 A (150 mm × 4.60 mm) column

Elution solvent: 100% acetonitrile gradient system with distilled water and 0.1% trifluoroacetic acid (TFA)

Flow rate: 1 ml / min

Injection volume: 10 μl

Detection wavelength: CAD

Loeseneriella The process of isolating and purifying the antimicrobial active substance from the cambodiana methanol extract is illustrated in FIG.

Example 3: Determination of structure of antimicrobial substance

Mass spectrometry and nuclear magnetic resonance analysis were performed to identify the structure of the antimicrobial active substance isolated in Example 2 above.

The molecular ion (M ⁺ ) was found at m / z 394 (Fig. 2) as a result of mass spectrometry (EI-MS) using an electron impact (EI) mode. The antimicrobial active substance was analyzed by gas mass analysis (GC-MS) according to the conditions shown in Table 3 below, and the analysis results were compared with those described in the mass spectrum library (FIG. 3).

GC system GC (JEOL QC5050) column DB-5 capillary column
(0.25 mm x 30 m, film thickness 0.25 m) Injector temperature 270 ℃ Interface temperature 250 ℃ Column temperature 120 占 폚 (5 minutes)? 270 占 폚 (25 占 폚)

As a result, although the antimicrobial active substance was represented by 1-aza-2-cyclotridecanone (12-aminododecanoic acid lactam) represented by the formula (1), since the mass analysis result was m / z 394, . Thus, ¹ H-NMR and ¹³ C-NMR spectra were obtained (FIGS. 4 and 5) for accurate identification of the structure of the antimicrobial active substance. As a result, the active substance was found to be 1,14-diazacyclohexaoxan- , 15-dione.

On the other hand, Gerald F. Koser, J. Org. Chem ., 43, 4393-4394, (1978)], 1,14-diazacyclohexanoic acid-2,15-dione was synthesized in the monomeric form of 1-aza- Compounds in the form of canon and trimer were obtained.

Mass analysis and nuclear magnetic resonance analysis were carried out in the same manner as above to identify the precise structure of the trimeric form of the compound obtained above. The molecular ion (M ⁺ ) was found at m / z 592 (FIG. 6). ¹ H-NMR spectrum was obtained for exact structure identification (Fig. 7). ¹ H-NMR spectral results showed 1-aza-2-cyclotridecanone, but mass spectrometric analysis of the antimicrobial substance revealed that it was present in the form of a trimer because m / z 592 was obtained. , 14,27-triazacyclononatriacontan. &Lt; / RTI &gt;

Example 4: Loeseneriella cambodiana Antimicrobial activity against plant pathogenic bacteria

The antimicrobial substances isolated and identified in Examples 2 and 3 were fungi of the rice blast fungus, rice sheath blight fungus, tomato gray mold fungus, Colletotrichum gloeosporioides (available from Korea Research Institute of Chemical Technology), Fusarium oxysporum f. sp. raphani , available from: Korea Research Institute of Chemical Technology), Sclerotinia sclerotiorum , Korea Research Institute of Chemical Technology) and Phytophthora capsici (available from: Korea Research Institute of Chemical Technology) were investigated for the growth inhibitory activity against 7 phytopathogenic fungi.

Each of the above antimicrobial substances was 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. As a test medium, the pathogens used were PDB (potato dextrose broth) medium.

The spores were harvested from rice blast fungus, tomato gray mold germ, anthracnose anthracnose bacterium, and non-anthracnose bacterium in a solid medium, and adjusted to 1 × 10 ⁴ spores / ml and 1 ml each was dispensed into a 48-well plate. The rice sheath blight and cucumber scarlet fungus were cultured for 7 days in PDB medium for 10 seconds with a blender and then inoculated 1% in sterilized PDB medium to prepare a suspension. The suspension was transferred to a 48-well plate Ml &lt; / RTI &gt;

Tomato germs and pepper spp. Were harvested and stored for 1 hour in a refrigerator. After germination, the juveniles were germinated, and the number of sporangia was adjusted to 1 × 10 ⁴ spores / ㎖.

Materials previously dissolved in DMSO were finally treated with 0.84, 2.5, 7, 6, 23, 67 and 200 ㎍ / ㎖, and DMSO was treated with 10 ㎕ per well in the control. The experiment was conducted with 3 replicates per each concentration. The inoculated well-plates were cultured at 25 ° C for 3 days to 5 days, and the minimum inhibitory concentration (MIC) was calculated. The results are shown in Table 4 .

Plant pathogen MIC ([mu] g / ml) 1-aza-2-cyclotridecanone 1,14-diazacyclohexanoic acid-2,15-dione 1,14,27-triazacyclononatriacontan-2,15,28-trione Rice blast ( M. grisea ) 400 100 200 Rice sheath blight ( R. solani ) 200 - - Tomato gray mold ( B. cinerea ) - - - Persimmon anthracnose fungus (C. gloeosporioides) 200 - - No chlorosis strain (F. raphani ) 200 200 - Cucumber sclerotiosis ( S. sclerotiorum ) - - - Pepper Station pathogens (P. capsici) 200 50 200

As shown in Table 4 above, it was confirmed that 1-aza-2-cyclotridecanone, 1,14-diazacyclohexacosane-2,15-dione and 1,14,27-triazacyclononatriacontan- , 15,28-trion showed antifungal activity in common against rice blast fungus and pepper spp., And monomeric and dimeric forms of fungicide showed common antifungal activity against non-causative bacteria. In addition, it was found that the trimer form of the compound had a somewhat lower antifungal activity than the monomer or dimer form of the compound.

Example 6: Loeseneriella cambodiana  Control efficacy of plant isolated from extracts

Loeseneriella cambodiana extract, 1-aza-2-cyclotridecanone obtained in Examples 2 and 3, 1,14-diazacyclohexacoxane-2,15-dione and 1,14,27-triazacyclonona The inhibitory effect on the in vivo bactericidal activity according to the structural difference of triacontan-2,15,28-trion was confirmed.

It was difficult to dissolve each substance, and 20% wadding agent (WP 20%) was prepared and its bactericidal activity was examined.

2 g of each sample was dissolved in a minimum amount of acetone, and then 1.5 g of synthetic hydrated silicon dioxide (white carbon; manufactured by Rhodia Asia Pacific Pte., Singapore) was added to prepare a 20% It was volatilized in the hood. The white carbon adsorbed on the sample was mixed with 0.5 g of sodium dodecylsulfate (CR-SDS; Yusen Chemical R & T Co., Ltd.) and 5.5 g of pyrophilite. Finally, the mixed sample was put into a blender and pulverized. Using the 20% wettable powders thus prepared, seven plant diseases such as rice blast, rice sheath blight, tomato gray mold, tomato blight, wheat rust, barley powdery mildew and red pepper anthracnose were tested as follows. Respectively.

Twenty 20 solution of 250 / / ml was added to each of the above 20% wettable powders, and the solution was adjusted to 500 times and 250 times. As a control group, a solution containing 250 占 퐂 / ml Tween 20 was used. 100 ppm of Benomyl, and 10 ppm of Flusilazole were used. Two pots were used for each plant, and the active ingredient samples were sprayed on the foliar surface, air dried for 24 hours, and inoculated with each plant pathogen. The inhibitory activity against these seven plant diseases was investigated according to the method described in Example 1, and the results are shown in Table 5 below.

Active ingredient density
(占 퐂 / ml) Control (%) RCB RSB TGM TLB WLR BPM PAN Loeseneriella cambodiana WP20% 500 0 65 46 21 83 25 0 250 72 75 81 36 100 80 0 1-aza-2-cyclotridecanone WP20% 500 92 35 26 64 60 8 42 250 98 45 46 91 83 17 75 1,14-diazacyclohexacosane-2,15-dione WP20% 500 80 15 8 0 13 8 8 250 92 35 15 50 87 50 25 1,14,27-triazacyclononatriacontan-2,15,28-trione WP20% 500 0 5 0 0 27 0 0 250 42 10 0 0 33 0 0 RCB: rice blast; RSB: rice sheath blight; TGM: Tomato gray mold disease; TLB: tomato blight; WLR: wheat red rust; BPM: barley powdery mildew; PAN: pepper anthracnose

As shown in Table 5 above, Loeseneriella cambodiana when the WP20% treatment showed 250 times the control effect of 100% for wheat leaf rust, rice blast, rice sheath blight showed, tomato gray mold and barley powdery mildew better control of more than 70% on their effectiveness. The control effect of Loeseneriella cambodiana WP20% against barley powdery mildew was compared with that of benomyl in Fig. 8, and the control effect against wheat red rust was compared with flucilazole in Fig.

1-aza-2-cyclotridecanone WP20% showed the best control effect in rice blast when treated with 250 times, 91% control effect against tomato blight, 83% against wheat red rust, And the control effect was confirmed.

When treated with 1,20-diazacyclohexanoic acid-2,15-dione WP20% at 250 times, it showed more than 50% control effect against rice blast, tomato blight, wheat rust and barley powdery mildew.

On the other hand, when treated with 1,20,28-fold of 1,14,27-triazacyclononatriacontan-2,15,28-trione WP20%, it was found to have a weak control effect against most plant diseases.

Claims (8)

A composition for controlling plant diseases, comprising an extract of Loeseneriella cambodiana or a compound represented by any one of the following formulas (1) to (3), or a mixture thereof, as an active ingredient.
[Chemical Formula 1]

(2)

(3)

delete The method according to claim 1,
Wherein the plant disease is caused by rice blast, rice sheath blight, tomato gray mold, tomato plague, wheat red rust, barley powdery mildew, red pepper anthracnose, anthrax anthracis, anthracnose bacterium, Wherein the composition is selected from the group consisting of plant extracts, plant extracts and plant extracts. The method according to claim 1,
Characterized in that the roe senerella cambodia extract is prepared using a C _1-7 lower alcohol or an aqueous solution thereof, a solvent selected from the group consisting of hexane, ethyl acetate, methylene chloride and a mixture thereof, . The method according to claim 1,
Wherein the plant disease controlling composition comprises a compound represented by any one of Chemical Formulas 1 to 3 or a mixture thereof in a concentration of 50 to 2,000 占 퐂 / ml. The method according to claim 1,
Wherein the composition for controlling plant diseases comprises a plant extract of Roesinerella cambodia at a concentration of 50 to 3,000 占 퐂 / ml. A method for controlling a plant disease, comprising treating a plant or plant disease controlling composition according to any one of claims 1 and 6 to a crop or soil. 8. The method of claim 7,
Wherein the plant disease is caused by rice blast, rice sheath blight, tomato gray mold, tomato plague, wheat red rust, barley powdery mildew, red pepper anthracnose, anthrax anthracis, anthracnose bacterium, &Lt; / RTI &gt; wherein the plant is selected from the group consisting of:

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