KR20140033709A - Novel mannosyl lipid derivatives derived from simplicillium lamellicola krict3 and composition containing the same for control plant diseases or insects - Google Patents

Abstract

The present invention relates to an agrochemical composition for plant disease control or pest control containing a novel mannosyl lipid derivative derived from Simplicillium lamellicola KRICT3 or its agrochemically acceptable salt as an active ingredient, and a method for preparing the same. The composition for plant disease control or pest control containing an extract or a novel mannosyl lipid derivative derived from Simplicillium lamellicola KRICT3 as an active ingredient has very excellent pesticidal, anti-bacterial, and anti-fugal activities. In addition, a plant disease control agent using the same can exhibit an effect on plant disease control even using its small quality and thus can improve marketability and productivity of crops. Further, Simplicillium lamellicola KRICT3 is a microorganism growing naturally in Korea, and the novel mannosyl lipid derivative according to the present invention derived therefrom has a great economic substitution effect, and thus the agrochemical composition containing the novel mannosyl lipid derivative as an active ingredient is useful as an insecticide, an anti-bacterial type plant disease control agent, or anti-fungal type plant disease control agent. [Reference numerals] (AA) Disease severity (0-5); (BB) Days after vaccination (day)

Description

TECHNICAL FIELD [0001] The present invention relates to a novel mannosyl lipid derivative derived from Simplicillium lamellicola KRICT3, and a plant disease or insect control composition containing the same as an effective ingredient. or insects}

The present invention relates to the use of Simplicillium < RTI ID = 0.0 > lamellicola (KCTC 11765BP) extract or a novel mannosyl lipid derivative derived therefrom as an active ingredient, and a method for producing the same.

Recent deterioration of global ecosystems due to weather changes has had a great impact on existing agricultural ecosystems, and this change has had a negative impact on sustainable food production. Crops face a number of environmental stresses, including wind and water damage during cultivation. Food crops depend on how well they control not only physical factors due to weather changes but also disease, pests and weeds, which are biological factors.

To date, chemical protection systems based on organic synthetic pesticides have been the mainstay for the protection of crops. However, adverse effects on pesticide abuse, toxicity, environmental pollution and natural ecosystem and decrease in drug efficacy due to the emergence of drug resistance have increased have.

On the other hand, interest in organic produce for a natural and healthy life is getting hotter as the term "well being" or "Lifestyle of Health and Sustainability".

The proportion of environmentally friendly agricultural products is expected to grow by an average of 14.6% per year, and the production and use of biologic pesticides, which are essential for the cultivation of environmentally friendly agricultural products such as organic cultivation, is also increasing every year. Therefore, it is required to develop a biocidal pesticide which is excellent in the control of plant diseases to replace synthetic pesticides for the production of environmentally friendly agricultural products.

Biopesticides are products made by selecting natural products, natural enemies and beneficial microorganisms derived from natural environment for agricultural use in order to remove diseases, insects and weeds that occur in crops. Biochemical pesticides include microbial pesticides (Miocrobial biopesticide) and biochemical biopesticides. Microbial pesticides are developed using microorganisms such as bacteria, fungi, viruses and nematodes. Biochemical pesticides are derived from plants or microorganisms Which is developed using natural products.

Commercialization of the developed bio-pesticides is more important than commercialization, commercialization, economics, and quantity and price of additives.

Therefore, in the development of biological control agents, the separation of useful microorganisms with excellent antagonism, the efficient delivery technology of microbial drugs, the securing of efficient mass production technology, the enhancement of active material production ability by introducing advanced genetic engineering technology, More research and development is needed for the development of the

R & D on biological pesticides began in earnest in the early 1970s and has been performed mainly in government institutes, universities, and businesses.

Previously known studies include cultivation of Streptomyces sp. SH09, a strain of actinomycetes isolated from soil, and methods for controlling powdery mildew and various phytopathogenic fungi of crops using the cultures, (Patent Document 1).

Next, a new microcysticin, Xylogone , which has a growth inhibitory effect against a phytopathogenic fungus including Pepper rot fungi, ganodermophthora ) and studies on a Pseudomonas maltophilia AG-12 strain, which has excellent antimicrobial activity, have been known (Patent Documents 2 to 3).

Moreover, Bacillus spp Chuo ringen cis kusu Taki (Bacillus having insecticidal and growth inhibitory effects on the phytopathogenic fungi of the order Lepidoptera pests at the same time thuringiensis subsp. The present invention relates to a process for the production of antifungal substances, insecticides and chitin degradation inhibiting substances, and a culture solution of the strains in a starch, a crude protein and a rock powder, (Patent Document 4 to Patent Document 7) have been disclosed.

However, the above-mentioned conventional invention has a problem that the antifungal and insecticidal activity is inferior, the antifungal and insecticidal activity is not maintained when stored at low temperature, the environmental preservation ability is lowered, and the growth promotion effect of the crop is not great.

Accordingly, the inventors of the present invention have been studying to develop new substances that can environmentally control various plant diseases such as gray mold disease and powdery mildew. Among them, Simplicillium < RTI ID = 0.0 > it was confirmed that the material isolated from the culture filtrate of the lamellicola KRICT3 strain (Accession No .: KCTC 11765BP) exhibits excellent insecticidal and antibacterial activity, thus completing the present invention.

Korea Patent Publication No. 2006-0017101 Korea Patent Publication No. 2011-0055458 Korean Patent Publication No. 1995-0018444 Korea Patent Publication No. 2005-0004719 Korean Patent Publication No. 2005-0018766 Korean Patent Publication No. 2005-0018767

It is an object of the present invention to provide a Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) extract for plant disease or pest control.

Another object of the present invention is to provide a method for producing the above extract.

It is still another object of the present invention to provide a plant disease or insect pest control composition containing the extract as an active ingredient.

Another object of the present invention is to provide a Mannosyl lipid derivative derived from the extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP).

It is still another object of the present invention to provide a method for producing the mannosyl lipid derivative.

Another object of the present invention is to provide a plant disease or insect pest control composition containing the Mannosyl lipid derivative as an active ingredient.

The present invention provides a Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) extract for plant disease or pest control.

In addition, the present invention relates to a method of culturing Simplicillium lamellicola KRICT3 (KCTC 11765BP) (step 1); And

The culture of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultivated in the step 1 is cultivated in one or more organic solvents selected from the group consisting of methanol, ethanol, acetone, butanol, chloroform and ethyl acetate (KCTC 11765BP) extract comprising a step (step 2) of extracting the extract of Simplicillium lamellicola KRICT3.

Furthermore, the present invention provides a plant disease or pest control composition containing an extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP) as an active ingredient.

The present invention also provides a Mannosyl lipid derivative represented by the following Formula 1 derived from an extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP).

[Formula 1]

(In the above formula 1, R < 1 _> And R < ₂ > are as defined herein.

Further, the present invention relates to a method for culturing Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) (step 1);

The culture of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultivated in the step 1 is cultivated in one or more organic solvents selected from the group consisting of methanol, ethanol, acetone, butanol, chloroform and ethyl acetate Extracting the extract to prepare an extract (step 2);

Performing column chromatography on the extract extracted in step 2 to obtain a fraction (step 3); And

And a step (step 4) of purifying the fraction obtained in step 3 by performing high performance liquid chromatography (HPLC) (step 4).

[Formula 1]

(In the above formula (1), R ₁ and R ₂ are as defined in the present specification.)

The present invention also provides a plant disease or insect control composition comprising Mannosyl lipid derivative represented by the following general formula (1) as an active ingredient.

[Formula 1]

(In the above formula (1), R ₁ and R ₂ are as defined in the present specification.)

The present invention relates to a method for controlling insecticidal or antimicrobial plant diseases comprising an extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) or a novel mannosyl lipid derivative derived therefrom as an active ingredient according to the present invention The present invention relates to a method for controlling a plant disease or an insect pest and a method for controlling a plant disease or an insect pest, Can be increased. In addition, the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) is a microorganism native to Korea, and the novel mannosyl lipid derivative according to the present invention extracted therefrom has an economical substitute effect The composition containing it as an active ingredient can be usefully used as an insecticide, an antibacterial plant disease control agent or an antifungal plant disease control agent.

Figure 1 is a simple florisil Solarium la mellitic coke KRICT3 strain (KCTC 11765BP) LAL Stony Oh solar nasae ahreom of the extract (Ralstonia solanacearum ) against tomato blight disease.
The symbols shown in Fig. 1 are as follows.
SLE: Tomato seedlings treated with Simplicillium lamellicola KRICT3 (KCTC 11765BP) extract.
SS: Tomato seedlings treated with a positive control (tryptomycin sulfate).
CK: Tomato seedlings treated with negative control.
Fig. 2 is a graph showing the effect of Rhizoctonia ( Rhizoctonia < RTI ID = 0.0 > solani ) strain of the present invention.
Figure 3 is a graphical representation of the Mannosyl lipid derivatives derived from the Simillis radiculichora KRICT3 strain (KCTC 11765BP), Rhizoctonia < RTI ID = 0.0 > solani ) strain of the present invention.

Hereinafter, the present invention will be described in detail.

The present invention provides an extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) for plant disease or pest control.

Simplicillium KRICT3 ( Simplicillium lamellicola KRICT3) strain (KCTC 11765BP) was isolated from gray mold ( Botrytis cinerea ), and it is a natural microorganism in Korea. Since the strain is easy to handle, the extract obtained therefrom is excellent in economical substitution effect.

The above Simplicillium KRICT3 The lamellicola KRICT3 strain (KCTC 11765BP) extract can be obtained by a manufacturing method comprising the following steps.

Simplicillium KRICT3 ( Simplicillium culturing the lamellicola KRICT3 strain (KCTC 11765BP) (step 1); And

The culture of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultivated in the step 1 is cultivated in one or more organic solvents selected from the group consisting of methanol, ethanol, acetone, butanol, chloroform and ethyl acetate (Step 2).

In the following, Simplicillium < RTI ID = 0.0 > lamellicola KRICT3) strain (KCTC 11765BP) is described step by step.

First, step 1 is a step of liquid culture of a strain to prepare an extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP).

At this time, it is preferable to use the strain obtained from the microorganism resource center in Korea Biotechnology Research Institute (Daejeon, Korea) (KCTC 11765BP).

The strains thus obtained can be cultured by adjusting the incubation period as necessary. Preferably, the strain can be cultured for several days to several tens of days, more preferably for five to ten days. In case of culturing for less than 5 days, there is a problem that the effect of controlling is insufficient due to insufficient generation of antifungal substances, and in case of culturing for more than 10 days, the production effect is lower than the increase in production cost.

In addition, the strain may be cultured by adjusting the temperature at which the cells can be cultured. Preferably, the strain can be cultured at 20 ° C to 30 ° C, more preferably at 25 ° C to 28 ° C. If the incubation temperature is lower than 20 ° C, the initial growth rate is slow and it takes a long time to cultivate the strain. When the incubation temperature exceeds 30 ° C, the growth is stopped and the strain may die. have.

Further, for the liquid culture of the strain, potato dextrose broth (PDB) medium, Czapek's Dox broth (CDB) medium, malt extract broth (MEB) medium, (MB) medium or Oatmeal broth (OB) medium, and the like, but the present invention is not limited thereto.

The step 1 according to the present invention is characterized in that Simplicillium lamellicola KRICT3 KRICT3) strain (KCTC 11765BP), the step (1-1) of adding the acetone to the culture medium and allowing the medium to stand.

The acetone added in the step 1-1 plays a role of effectively removing the polymer substance present in the medium.

Next, step 2 according to the present invention is a step of extracting the cultured Simplicillium lamellicola KRICT3 (KCTC 11765BP) culture solution with organic solvent.

At this time, there is no particular limitation on the organic solvent that can be used, but methanol, ethanol, acetone, butanol, chloroform or ethyl acetate can be used, and ethyl acetate is particularly preferably used.

Furthermore, the present invention provides a plant disease or pest control composition containing an extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP) as an active ingredient.

According to the experiment for measuring the insecticidal effect against the extract of Simplexylum lamellicola KRICT3 strain (KCTC 11765BP) according to the present invention, it has an insecticidal effect on peach aphid ( Myzus persicae ) (see Experimental Example 1) In order to evaluate the antimicrobial effect against tomato seedlings, the tomato seedlings treated with the strain extract were identified as Ralstonia solanacearum ) strain in a dose-dependent manner. In particular, when treated at a concentration of 1000 μg / ml or more, the antimicrobial activity was superior to that of tryptic sulfate triacylglycerol (200 μg / ml), which is conventionally used as an antibacterial agent for control purposes (see Experimental Example 2). In addition, according to the experiment for measuring the antifungal effect, there is an antifungal activity against various plant pathogens. In particular, the IC ₅₀ value for Rhizoctonia solani strain was 11.11 / / ml, and Rhizoctonia solani (see Experimental Examples 3 to 4).

Accordingly, the composition containing the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) according to the present invention as an active ingredient may be useful as a pesticide or an antimicrobial herbicide.

The present invention relates to the use of Simplicillium < RTI ID = 0.0 > (Mannosyl lipid) derivative represented by the following general formula (1) derived from a lamellicola KRICT3 strain (KCTC 11765BP).

[Formula 1]

In Formula 1,

R ₁ is hydrogen or an acetyl group; And

또는

이다.
R ₂ is hydrogen,

or

to be.

Preferably, the derivative of formula (1) is a compound represented by the following formula (2) to (4).

(2)

(3)

[Chemical Formula 4]

The above Simplicillium KRICT3 The compound represented by the following formula (1) derived from the lamellicola KRICT3 strain (KCTC 11765BP) can be obtained by a production method comprising the following steps.

Simplicillium KRICT3 ( Simplicillium culturing the lamellicola KRICT3 strain (KCTC 11765BP) (step 1);

The culture of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultivated in the step 1 is cultivated in one or more organic solvents selected from the group consisting of methanol, ethanol, acetone, butanol, chloroform and ethyl acetate Extracting the extract to prepare an extract (step 2);

Performing column chromatography on the extract extracted in step 2 to obtain a fraction (step 3); And

Purifying the fraction obtained in step 3 by performing high performance liquid chromatography (HPLC) (step 4).

[Formula 1]

(Wherein R ₁ and R ₂ are as defined in Formula 1).

In the following, Simplicillium < RTI ID = 0.0 > The method for producing Mannosyl lipid derivatives derived from the lamellicola KRICT3 strain (KCTC 11765BP) is described step by step.

First, step 1 is a step of liquid culture of a strain to prepare an extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP).

At this time, it is preferable to use the strain obtained from the microorganism resource center in Korea Biotechnology Research Institute (Daejeon, Korea) (KCTC 11765BP).

The strains thus obtained can be cultured by adjusting the incubation period as necessary. Preferably, the strain can be cultured for several days to several tens of days, more preferably for five to ten days. In case of culturing for less than 5 days, there is a problem that the effect of controlling is insufficient due to insufficient generation of antifungal substances, and in case of culturing for more than 10 days, the production effect is lower than the increase in production cost.

In addition, the strain may be cultured by adjusting the temperature at which the cells can be cultured. Preferably, the strain can be cultured at 20 ° C to 30 ° C, more preferably at 25 ° C to 28 ° C. If the culture temperature is less than 20 ° C., the initial growth rate is slow and it takes a long time to cultivate the strain. If the culture temperature exceeds 30 ° C., the growth is stopped and the strain is killed.

Further, for the liquid culture of the strain, potato dextrose broth (PDB) medium, Czapek's Dox broth (CDB) medium, malt extract broth (MEB) medium, (MB) medium or Oatmeal broth (OB) medium, and the like, but the present invention is not limited thereto.

The step 1 according to the present invention may further comprise the step of adding acetone to the culture medium (step 1-1) after culturing the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP).

The acetone added in the step 1-1 plays a role of effectively removing the polymer substance present in the medium.

Next, step 2 according to the present invention is a step of extracting the cultured Simplicillium lamellicola KRICT3 (KCTC 11765BP) culture solution with organic solvent.

At this time, there is no particular limitation on the organic solvent that can be used, but methanol, ethanol, acetone, butanol, chloroform or ethyl acetate can be used, and ethyl acetate is particularly preferably used.

Further, step 3 according to the present invention comprises performing column chromatography on the extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP) extracted KRCT3 to obtain a fraction containing the compound represented by formula (1) to be.

In the above-mentioned strain extract, silica gel may be used as a stationary phase, but the present invention is not limited thereto in order to obtain fractions using column chromatography.

The elution solvent used for fractionation using column chromatography was ethyl acetate / methanol / distilled water = 80/10/5 in ethyl acetate / methanol / distilled water / Fraction of distilled water / acetic acid = 80/10/8/1, methylene chloride / methanol / distilled water = 60/40/10.

Next, the step 4 according to the present invention is a step of purifying the fractions obtained in the step 3 by high performance liquid chromatography (HPLC) with the compounds 2 to 4 represented by the general formulas (2) to (4).

The high performance liquid chromatography (HPLC) for purification can use C18 column (5 탆, 20 mm x 250 mm), but is not limited thereto.

In addition, the concentration gradient of high performance liquid chromatography (HPLC) on the eluting solvent can be adjusted depending on the amount of the fraction to be separated or the column size and kind of high performance liquid chromatography (HPLC). Preferably, after the start of the purification, the concentration of methanol, which is an eluting solvent, is changed from 45% to 100% for up to 30 minutes, and then fixed with 100% methanol for 10 minutes.

Further, in high performance liquid chromatography (HPLC) purification, the UV measurement wavelength is preferably measured at 204, 215 and 254 nm.

The present invention provides a plant disease or insect pest control composition comprising a mannosyl lipid derivative represented by the following general formula (1) as an active ingredient.

[Formula 1]

(Wherein R ₁ and R ₂ are as defined in formula (1)).

Experiments measuring the insecticidal effects against the compounds 2 to 4 represented by the general formulas (2) to (4) according to the present invention show that the insecticidal effect of the peach aphid is remarkably excellent. Further, according to the experiment for evaluating the antibacterial effect on the compounds represented by the formulas (2) to (4), the compounds 2 to 4 represented by the formulas (2) to (4) have antibacterial effect on various plant pathogenic bacteria In particular, in the case of the compound 2 represented by the general formula (2), Acidovorax konjaci ) strain, Agrobacterium tumefaciens strain, Burkholderia < RTI ID = 0.0 > glumae strain, Ralstonia & lt ; RTI ID = 0.0 > solanacearum ) strain and Santomonas xanthomonas euvesicatoria ) and the like (see Experimental Example 5). In addition, according to the experiment for measuring the antifungal effect, there is an antifungal activity against various plant pathogens. In particular, Rhizoctonia solani) if the IC ₅₀ value for the strain of the compound 2 represented by Formula 2, 3.22 ㎍ / ml, Compound 3 represented by Formula 3, 1.13 ㎍ / ml, for compound 4 of the formula (4), 1.67 / / Ml , the antifungal activity against Rhizoctonia solani strain was remarkably excellent (see Experimental Example 3).

Accordingly, the composition containing the compound represented by formulas (2) to (4) according to the present invention as an active ingredient can be usefully used as an insecticide or an antimicrobial plant disease control agent.

In accordance with the present invention, Simplicillium < RTI ID = 0.0 > KRICT3 < a composition containing an extract of lamellicola KRICT3 strain (KCTC 11765BP) or a mannosyl lipid derivative derived from a strain represented by the formula (1) as an active ingredient is useful for preventing and / or preventing diseases such as konnyaku, Diptera, Rice blast fungus, rice blast fungus, rice blast fungus, rice blast fungus, tomato gray mold fungus, tomato blight, wheat red rust, barley powdery mildew, red pepper fungus spot blight, rice sheath blight, Or pepper anthracnose.

In addition, the composition containing the Mannosyl Lipid Derivative derived from the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) extract or the strain represented by the formula (1) as an active ingredient according to the present invention is not limited to the Ashido vulcanic cone Acidovorax konjaci , Agrobacterium tumefaciens , Burkholderia < RTI ID = 0.0 > glumae ), Pectobacterium carotovora subsp. carotovora ( Pectobacterium carotovora subsp. carotovora , Pseudomonas sp. syringae pv. lachrymans , Ralstonia, solanacearum , Xanthomonas euvesicatoria , Rhizoctonia < RTI ID = 0.0 > solani , Magnaporthe oryzae , Botrytis < RTI ID = 0.0 > cinerea , Phytophthora infestans , Puccinia < / RTI > recondita ), blue mariamgrenis f.sp. Blumeria graminis f.sp. hordei ) or colletotrichum cocodes ( Colletotrichum coccodes , and the like. Therefore, it can be effectively used as a composition for controlling antimicrobial plant diseases for controlling the plant diseases.

Hereinafter, the present invention will be described more specifically with reference to Examples and Experimental Examples.

However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the present invention is not limited to the following Examples and Experimental Examples.

< Example  1> Simplicillium Ramelicola  KRICT3 ( Simplicillium lamellicola  (KRICT3) strain (KCTC 11765BP)

(KRCT 11765BP) was cultivated in a potato dextrose broth (PDB) medium (Becton, Dickinson and Co., Sparks, MD, USA) containing a rotary shaker . At this time, shaking culture was carried out at 25 rpm for 10 days at 150 rpm. The culture was centrifuged at 10,000 rpm for 10 minutes, and the supernatant was collected. The same amount of acetone as that of the aliquot was added to the aliquots and left for 24 hours. Thereafter, the mixture was filtered using filter paper, and the filtered filtrate was concentrated under reduced pressure to remove acetone. The concentrated aqueous solution was extracted with an equal volume of ethylacetate and the extracted organic layer was washed with sodium sulfate (Na ₂ SO ₄ ), then the solvent was removed at 40 ° C., An extract of cola KRICT3 strain (KCTC 11765BP) was obtained.

< Example  2> Mannosil  Geology ( Mannosyl lipid ) &Lt; / RTI &gt;

Step 1: Simplicillium Ramelicola KRCICT3  Of the strain (KCTC 11765BP) Fraction  Produce

The extract (2.5 g) obtained in the above step 1 was purified by column chromatography (silica gel, 100 g Kiesel gel 60 (230-400 mesh), 3.4 cm x 40 cm) with a volume ratio of ethyl acetate / methanol / distilled water of 80/10/2 (200 ml, elution solvent B) in which the volume ratio of ethyl acetate / methanol / distilled water / ethyl acetate / methanol / distilled water / acetic acid was 80/10/5, starting from 200 ml of the eluting solvent (A) (500 ml, elution solvent D) in which the volume ratio of methylene chloride / methanol / distilled water was 60/40/10 was sequentially used as a solvent (ABE1 to ABE15 / 10/8 / 15 fractions.

Step 2: Mannosil  Preparation of lipid derivatives

The fractions obtained in the above step 1 were aliquoted and the separated fractions were added to Ralstonia &lt; RTI ID = 0.0 &gt; solanacearum ) was added at a concentration of 100 μl / ml, and the changes were observed using thin-layer chromatography (Kiesil gel 60GF 254, 0.25 mm layer thickness; E. Merck, Damstadt, Germany). ABE5 to Lal Stony Ah Solar nasae ahreom in fractions of ABE8 (Ralstonia solanacearum ), and thin film chromatography patterns of ABE5 to ABE8 were similarly observed. ABE5 to ABE8 with antimicrobial activity were concentrated and then purified by high performance liquid chromatography (HPLC) to obtain the compounds 2 to 3 represented by Formulas 2 to 3 (Compound 2: 85 mg, Compound 3: 23 mg) . Further, the fraction ABE13 was purified by thin layer chromatography (ethyl acetate / methanol / distilled water / acetic acid = 80/10/8/1, v / v / v / v) to obtain the compound 4 (12 mg) . The gradient of the mobile phase was adjusted from 45 minutes to 45 minutes using a Capcell Pak C18 UG120 Å column (5 ㎛, 20 mm × 250 mm; Shiseido Co., Tokyo, Japan) The concentration was changed to 100% methanol and then fixed with 100% methanol for 10 minutes. The UV measurement wavelength was measured at 204, 215 and 254 nm. The ¹ H NMR and ¹³ C NMR spectra of the compounds 2 to 4 obtained by the purification were measured and are shown in Table 1 below.

Compound 2 Compound 3 Compound 4 Mannoza ¹³ C ¹ H ¹³ C ¹ H ¹³ C ¹ H One' 101.18 4.61 brs 101.23 4.61 brs 100.7 4.66 brs 2' 72.76 3.83 m 72.70 3.83 m 72.71 3.87 m 3 ' 75.27 3.44 m 75.25 3.43 m 75.21 3.44 m 4' 68.56 3.53 m 68.60 3.52 m 68.55 3.53 m 5 ' 78.27 3.22 m 78.29 3.2 m 78.44 3.22 m 6 ' 62.97 3.71 m; 3.82 m 62.99 3.69 m; 3.83 m 62.93 3.69 m; 3.84 m One 173.06 173.14 173.06 2 41.83 2.57 m; 2.85 m 42.10 2.36 m; 2.48 m 37.76 2.76 m; 2.84 m 3 74.93 4.21 m 74.94 4.17 m 78.01 4.67 m 4 39.84 1.74-1.92 m 39.82 1.82 - 1.91 m 36.63 1.64 -1.73 m 5 72.84 5.03 m 72.80 5.03 m 70.83 4.40 m 6 35.41 1.60 brs 35.39 1.59 brs 33.75 1.62 brs 7 25.97 1.31 brs 25.94 1.29 brs 25.65 1.34 brs 8 32.83 1.31 brs 32.79 1.29 brs 32.77 1.34 brs 9 23.71 1.31 brs 23.62 1.29 brs 23.61 1.34 brs 10 14.44 0.89 t (7.01) 14.42 0.89 t (7.06) 14.41 0.91 t (6.9) CH3CO 21.24 2.02 s 21.29 2.02 s CH3 CO 172.61 172.65 One 172.47 173.06 2 40.76 2.43-2.49 m 43.19 2.38-2.48 m 3 66.77 4.09 m 66.76 3.54 m 4 42.11 1.72-1.78 m 42.22 1.72-1.79 m 5 73.71 5.05 m 73.13 5.07 m 6 35.10 1.61 brs 35.11 1.59 brs 7 25.91 1.31 brs 25.94 1.29 brs 8 32.78 1.31 brs 32.79 1.29 brs 9 23.60 1.31 brs 23.62 1.29 brs 10 14.37 0.89 t (7.01) 14.42 0.89 t (7.06) One 172.63 175.69 2 43.57 2.48-2.51 m 43.55 2.38-2.48 m 3 70.02 5.28 m 66.85 3.54 m 4 39.30 1.81 m 42.36 1.72-1.79 m 5 72.61 4.93 m 72.86 5.04 m 6 35.14 1.61 brs 35.11 1.59 brs 7 25.91 1.31 brs 25.94 1.29 brs 8 32.82 1.31 brs 32.79 1.29 brs 9 23.66 1.31 brs 23.62 1.29 brs 10 14.40 0.89 t (7.01) 14.42 0.89 t (7.06) CH3CO 21.24 2.01 s CH3 CO 172.47 One 173.16 2 43.55 2.43-2.48 m 3 66.82 4.09 m 4 42.37 1.72-1.78 m 5 72.84 5.03 m 6 35.06 1.61 brs 7 25.91 1.31 brs 8 32.72 1.31 brs 9 23.59 1.31 brs 10 14.36 0.89 t (7.01)

< Experimental Example  1> Simplicillium Lamella Coke  KRICT3 ( Simplicillium lamellicola KRICT3) strain (KCTC 11765BP) and Mannosil  Geology ( Mannosyl lipid ) Derivatives

The following experiment was conducted to evaluate the insecticidal effect of the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) and the mannosyl lipid derivative according to the present invention.

In order to examine the insecticidal effect on peach lycopodium aphid, the insecticidal effect of Simplexylum laminolica KRICT3 strain (KCTC 11765BP) prepared in Example 1 and the compounds 2 to 3 prepared in Example 2 was evaluated. A homogeneous secondary peach aphid ( Myzus persicae ) Ten larvae were placed in a 1.5 × 1.5 cm size chopped cabbage leaf with a soft brush and then moistened with distilled water. 6 &lt; / RTI &gt; filter paper. Plates with aphids were placed at 25 ° C and 70% humidity. Twelve hours after the seeding, 10 μl of the insecticidal activity sample obtained above was spread evenly on aphids using a micropipette. At this time, the untreated group was treated with the same amount as a mixed solvent of 10% (v / v) dimethyl sulfoxide (methanol = 4: 1, v / v). Also, Dirhamnolipid, which is known to have a high aphid insecticidal activity, was treated as a positive control. The insecticidal efficiency was investigated 24 hours after the treatment according to Abbott (1925) method in consideration of live aphid and insecticidal water as follows. All experiments were repeated 3 times. The mortality rate was calculated using the following formula (1). The results are shown in Table 2 below.

In the above equation (1), A represents the number of living organisms in the control group, and B represents the number of living organisms in the treated group.

density Insecticide rate Simplicillium lamellicola strain extract 12 ug / ml 29.6 ± 3.9 Simplicillium lamellicola strain extract 37 / / ml -15.9 + 38.6 Simplicillium lamellicola strain extract 111 / / ml 45.5 ± 28.9 Simplicillium lamellicola strain extract 333 ug / ml 68.2 ± 38.8 Simplicillium lamellicola strain extract 1000 / / ml 79.6 ± 18.0 Compound 2 12 ug / ml 2.67 ± 10.88 Compound 2 37 / / ml 29.6 ± 23.9 Compound 2 111 / / ml 70.5 ± 20.8 Compound 2 333 ug / ml 100.00 ± 0.00 Compound 2 1000 / / ml 100.00 ± 0.00 Compound 3 12 ug / ml 15.9 ± 14.2 Compound 3 37 / / ml 86.4 ± 11.8 Compound 3 111 / / ml 100.00 ± 0.00 Compound 3 333 ug / ml 100.00 ± 0.00 Compound 3 1000 / / ml 100.00 ± 0.00 Untreated group 0 ㎍ / ml 0.00 ± 0.00 Positive control group 100 [mu] g / ml 100.00 ± 0.00

As shown in Table 2, the extract of Simplicillium lamellicola (KCTC 11765BP) prepared in Example 1 according to the present invention has an insecticidal effect. In addition, the compound 2 produced in Example 2 exhibited a remarkably excellent insecticidal effect against peach aphid at a concentration of 111 / / ml and a concentration of 37 ㎍ / ml or higher. Compared with Dirhamnolipid isolated from the conventionally used Pseudomonas sp . EP-3 strain used as a positive control, the compounds 2 to 3 prepared in Example 2 had similar insecticidal activity .

From these results, it can be seen that the compounds 2 to 3 derived from the extracts of Simplicillium lamellicola strain (KCTC 11765BP) according to the present invention and the Simplicillium lamellicola strain (KCTC 11765BP) are excellent in insecticidal effect.

Therefore, the compound represented by the formula (1) derived from the extract of Simplicillium lamellicola strain (KCTC 11765BP) according to the present invention or the strain Similisium lamellicola (KCTC 11765BP) has excellent insecticidal effect, The present invention can be effectively used as a composition for controlling plant diseases by insecticides and insect pests.

< Experimental Example  2> Simplicillium Ramelicola  KRICT3 ( Simplicillium lamellicola Evaluation of the antibacterial effect of KRICT3 strain (KCTC 11765BP) extract

In order to evaluate a simple florisil Solarium la mellitic coke antibacterial effect of KRICT3 strain (KCTC 11765BP) extract according to the present invention in vivo (in vivo experiments were performed as follows.

The extract prepared in Example 1 was dissolved in methanol (2 ml) to give 25, 50 and 100 mg / ml. Then, the extract was dissolved in distilled water (98 ml) in which tween 20 (250 占 퐂 / ml) To prepare diluted solutions of extracts having final concentrations of 500, 1000 and 2000 占 퐂 / ml. Next, in a triptic soy agar (TSA) medium petri dish, Ralstonia &lt; RTI ID = 0.0 &gt; Solanacearum strains were cultivated at 30 ° C for 48 hours and washed with distilled water. The washed strain culture solution was adjusted to an OD ₆₀₀ of 0.1 (about 1.5 × 10 ⁸ cells / ml) with distilled water to prepare a hospital strain solution. After that, 20 ml of a diluted solution of Simplexylum laminaria coli KRICT3 strain (KCTC 11765BP) prepared for each concentration in a tomato seedlings grown on a horticultural soil in a 0.5 L plastic flowerpot was inoculated. After 3 hours, 20 ml of the prepared strain was inoculated, and after 5 days, a diluted solution of Simplexilium laminycorrhiza KRICT3 (KCTC 11765BP) strain prepared by concentration was again used. As a positive control, distilled water supplemented with tween 20 (250 占 퐂 / ml) as a negative control group was added to tryptomycin sulfate (200 占 퐂 / ml), which is widely used as an antimicrobial agent for gram-positive bacteria and gram- Tomato seedlings. The treated plants were grown in a constant temperature humidifier at 85% humidity, 28 &lt; 0 &gt; C temperature and 12 hours photoperiod. During the growth, no additional nutrition was provided and only water needed for growth was supplied. After 15 days of inoculation of the pathogen, plant disease incidence was measured in units of 0 to 5. In this case, 0 means that the plant leaves are not dried, 1 means that one of the plant leaves shows partial blotting, 2 means that 1 or 2 plant leaves are dry, 3 means 2 to 3 Four plant leaves show that four or more plant leaves are dry. Finally, 5 indicates that the plant itself has died. This experiment was carried out twice for each of five extracts or control groups sprayed on tomato seedlings, and the results are shown in Fig.

As shown in FIG. 1, the tomato seedlings treated with the extract of Simplexilium lamellicola KRICT3 strain (KCTC 11765BP) according to the present invention were obtained from Ralstonia solanacearum ) strain, it can be seen that no blight was observed. In particular, in the case of treating the extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) prepared in Example 1 with 500 μg / ml, the sulfuric acid tryptomycin sulfate and the negative control group, which were conventionally used as a positive control group, It can be observed that the blight was developed similarly to the distilled water in which the twin 20 was dissolved, but when the extract of Simplexylum lamellicola KRICT3 strain (KCTC 11765BP) was treated at 1000 to 2000 占 퐂 / ml, the blight was prevented Able to know. From this, the extract of Simplexyl Lamellicola KRICT3 strain (KCTC 11765BP) prepared in Example 1 according to the present invention was obtained from Ralstonia &lt; RTI ID = 0.0 &gt; solanacearum ) strain of the present invention.

Therefore, the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) according to the present invention is superior in antibacterial activity to sulfur triptomycin sulfate, which is conventionally used as a Gram-positive bacterium and a Gram-negative bacterium as an antibacterial agent, And can be effectively used as a composition for controlling an anti-bacterial agent or an anti-bacterial plant disease.

< Experimental Example  3> Simplicillium Ramelicola  KRICT3 ( Simplicillium lamellicola Evaluation of antifungal effect of KRICT3 strain (KCTC 11765BP) extract

In vitro In order to evaluate the simple florisil Solarium la mellitic coke antifungal effect of KRICT3 strain (KCTC 11765BP) extract according to the present invention (in vitro ) experiments were performed as follows.

The extract of Simplicillium lamellicola KRICT3 (KCTC 11765BP) prepared in Example 1 was dissolved in methanol, and then the methanol (100 μl) was dissolved in a potato dexrose agar (PDA , 9900 [mu] l) and dispensed in 2 ml portions and dispensed into sterile 6-wells of 3.5 cm in diameter and fixed. At this time, the final concentration of the extract fixed to the wells was adjusted to 0, 1, 10, 100, and 1000 / / ml, and a mixed solution obtained by dissolving 1% methanol in the potato agar medium sterilized with the untreated group was used. A 5 mm diameter agar piece was removed from Rhizoctonia solani cultures grown on potato agar medium and inoculated into each well treated with compound. The mycelial growth was measured at the time when the hypha of the untreated group reached the edge of the well at 25 DEG C, and the result was shown in Fig.

As shown in FIG. 2, the extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) according to the present invention is a Rhizoctonia solani solani ) was increased, and Rhizoctonia ( Rhizoctonia &lt; RTI ID = 0.0 &gt; IC ₅₀ for solani) strain is found to be 20.3 ㎍ / ml. From this, the extract of Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) prepared in Example 1 according to the present invention is a Rhizoctonia solani ) strain of the present invention has excellent antifungal activity.

Therefore, the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) according to the present invention has excellent antifungal activity against various plant pathogenic strains, and in particular, Rhizoctonia solani ), it is useful as an antifungal agent or an antifungal agent for controlling plant diseases.

< Experimental Example  4> Simplicillium Ramelicola  KRICT3 ( Simplicillium lamellicola KRICT3) strain (KCTC 11765BP) In botanical bottles  Evaluation of anti-inflammatory activity

In order to evaluate the effect of simple florisil Solarium la mellitic coke KRICT3 strain (KCTC 11765BP) of the plant extract disease control according to the present invention in vivo (in vivo experiments were performed as follows.

The extracts obtained in Example 1 were tested for the production of Magnaporthe oryzae , Rhizoctonia solani , Botrytis cinerea , Blumeria graminis f. sp. hordei , tomato blight ( Phytophthora infestans ), wheat red rust ( Puccinia recondita ) and pepper anthracnose ( Colletotrichum coccodes ) in vivo vivo antimicrobial activity was investigated. The methanol extract was dissolved in methanol (final concentration, 5%), and then the surfactant Tween 20 was diluted with distilled water containing 250 μg / ml to adjust the final concentration of the methanol extract to 1,000 μg / ml. The control group was distilled water containing 5% methanol and 250 占 퐂 / ml Tween 20. Two pots were used per plant, and the extracts were sprayed on the leaves, air dried for 24 hours, and each plant pathogen inoculated. In case of rice, 250 ug / ml solution of tween was pre-sprayed 4 hours before spraying the culture solution to improve the adhesion strength, and then dried at room temperature.

The rice, tomato, wheat and barley used in the experiment were filled with plastic pots with a diameter of 4.5 cm at a ratio of 70%, and the seeds were sown and cultivated in a greenhouse at 25 ± 5 ° C for 1 to 4 weeks. The rice blast fungus is grown in 3 to 4 leaf stage seedlings by Magnaporthe oryzae, Korea spore suspension of the Research Institute of Chemical Technology) ⁽⁵ × 10 5 and then spraying the spores / ml) inoculation and seupsil processing for a day in a moist substance of 25 ℃, led to the onset to five days incubation in thermostatic chamber of 25 ℃ . The rice sheath blight is caused by Rhizoctonia solani , Korea Research Institute of Chemical Technology) were cultured for 7 days in medium (90 g of wheat bran, 15 g of rice hull and 100 ml of distilled water), inoculated in 5-leaf stage seedlings, treated for 4 days in a wet condition at 25 ° C, Lt; RTI ID = 0.0 &gt; C &lt; / RTI &gt; for 4 days. Tomato blight is caused by the presence of Phytophthora (5 × 10 ⁴ sporangia / ml) of the infant suspension (5 × 10 ⁴ sporangia / ml) of the infant, infestans , and Kangnung Univ.) were inoculated by spraying at 25 ° C for 2 days in a wet condition and incubated for 1 day in a constant temperature and humidity room at 25 ° C Respectively. The tomato gray mold disease is caused by the presence of Botrytis cinerea, a causative organism of gray mold, spore suspension of the cinerea, Korea Research Institute of Chemical Technology) (after treatment with ^{5 × 10 5 spores / ml)} , led to the onset and for 3 days in a moist substance of 20 ℃. The spore of Puccinia recondita (University of Incheon), a causative organism of rust, which is known as active parasitic bacteria, was suspended in 250 μg / ml Tween 20 solution in an amount 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 observed in the blueberry germinis f. sp. Blumeria graminis f. sp. hordei , Korea Research Institute of Chemical Technology) were inoculated and incubated for 7 days in a constant temperature chamber at 20 ° C to induce the onset. After 7 days of inoculation, 8 days after inoculation of rice sheath blight, and 3 days after inoculation with tomato gray mold and tomato blight,

In order to test the antiseptic activity against pepper anthracnose, a plastic port having a diameter of 7.0 cm was filled with about 70% of the horticultural soil, and the best pepper seeds were sown. The seeds were raised in the greenhouse to the third or fourth leaf stage. The sample was sprayed on the leaf surface. After spraying the sample, it was dried at room temperature for 24 hours, and then colletotrichum coccodes , Korea University) were inoculated by spraying with a spore suspension (4 × 10 ⁵ spores / ml). After 2 days of onset, it was allowed to stand in a constant temperature room at 25 ℃ for 1 day. (%) Was calculated according to the following equation (2) using the lesion area ratio obtained from the above, and the results are shown in Table 3.

Active ingredient Concentration (/ / ml) Control (%) RCB RSB TGM TLB WLR BPM PAN Strain
extract 3000 56 100 46 98 100 42 56 1000 38 25 31 7 53 0 25

In Table 3 above,

RCB: rice blast, RSB: rice sheath blight, TGM: tomato gray mold, TLB: tomato plague, WLR: wheat red rust, BPM: barley powdery mildew, PAN: pepper anthracnose.

As shown in the above Table 3, when the extract of Simplexylum lemicolor KRICT3 (KCTC 11765BP) is exposed to the above-mentioned seven plant diseases, it can be known that there is an effect of controlling the extract, When the concentration of the extract of KRICT3 (KCTC 11765BP) was 3000 ㎍ / ml, the control value against rice blast, tomato gray mold, barley powdery mildew and red pepper anthracnose was about 42% to 56%, and rice sheath blight, The control for wheat red rust was more than 98%. From this, it can be seen that the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) according to the present invention has excellent control effect against various plant diseases, and in particular, it has excellent antifungal effect against rice sheath blight, tomato blight, It can be seen that the effect is excellent.

Accordingly, the extract of Simplexylum lamellicola KRICT3 (KCTC 11765BP) according to the present invention is excellent in insecticidal effect against pests, and exhibits remarkably excellent antimicrobial activity against various plant pathogenic strains. Therefore, Can be effectively used as a plant disease or antifungal plant disease control composition.

< Experimental Example  5> Mannosil  Evaluation of Antibacterial Effect of Lipid Derivatives

In vitro (in order only in accordance with the invention to assess the antibacterial effect of the lipid derivative nosil vitro ) experiments were performed as follows.

Antibacterial assays were performed on 96-well microtiter plates based on the broth microdilution method. The Ralstonia solar nacre arum used in the experiment solanacearum ) was cultured in TSB medium, and Acidovorax konjaci ) strain, Agrobacterium tumefaciens strain, Burkholderia &lt; RTI ID = 0.0 &gt; glumae strains, Pectobacterium carotovora subsp. carotovora strains, Pseudomonas sp . strains, Pseudomonas sp. syringae pv. lachrymans) strain and Pseudomonas Santo Juve Brassica thoria (Xanthomonas euvesicatoria ) were cultured in NB medium. Subsequently, the reference solutions were prepared by dissolving the compounds 2 to 4 (1000 μl / ml, respectively) prepared in Example 2 in methanol, and the prepared reference solutions were added to the TSB medium and NB And diluted to a concentration of 0.39 to 100 mu l / ml in the medium. Each bacterial strain (50 μl) cultured at 2 × 10 ⁶ cells / ml was inoculated into each of diluted solutions (2 μl to 4 μl) of Compound 2 to Compound 4 to make 100 μl of the final solution. In the positive control group, tryptic sulfate sulfate was treated with the diluted solution prepared at the concentration of 0.039 to 100 / / ml in the same manner as above, and the negative control was treated with diluted 1% methanol. Wells treated with the positive control, negative control and compounds 2 to 4 according to the present invention were stirred at 300 rpm for 20 minutes and then cultured at 30 ° C for 48 hours. After incubation, the degree of fungal culture in each well was evaluated by measuring the optical density (OD) at a wavelength of 600 nm with a microplate reader (Bio-Rad, Benchmark Plus, CA, USA) . At this time, the reference solutions of the compounds 2 to 4 were diluted in the TSB medium and the NB medium to prepare a diluted solution, and the diluted solution was injected into the wells to measure optical density, and the optical density of the wells treated with the compound and the negative control . The experiment was conducted at least three times to obtain the average value. (De La Fuente et al., 2006), and the growth inhibition rate (%) according to the concentration was probit analyzed to calculate the IC ₅₀ Value. This is shown in Table 4 below.

Strain name IC ₅₀ (95% CI) Compound 2 Compound 3 Compound 4 A. konjaci 22.5
(8.5-59.9) > 100 > 100 Agrobacterium tumefaciens ( A. tumefaciens ) 1.58
(0.91-2.74) 1.49
(0.18-2.95) 24.8
(16.9-36.4) B. glumae 33.2
(18.9-58.4) > 100 NI P. carotovora subsp . Carotovora ) > 100 > 100 NI Pseudomonas syllin variant Lacrimans
( P. syringae pv . lachrymans ) > 100 > 100 > 100 R. solanacearum ( R. solanacearum ) 73.8
(41.1-106.1) 75.8
(44.3-107.4) > 100 Santo Monas Yubeshkatoria
( X. euvesicatoria ) 72.1
(40.6-103.6) > 100 > 100

95% CI: 95% confidence interval

NI: No Suppression Effect

As shown in the above Table 4, it was confirmed that the Simplicillium &lt; RTI ID = 0.0 &gt; (KRICT3) &lt; / RTI &gt; prepared in Example 2 according to the present invention Compounds derived from the lamellicola KRICT3 strain (KCTC 11765BP) were found to be antibacterial to plant pathogenic bacteria. Particularly, Compound 2 is an Acidovorax konjaci ) strain, Agrobacterium tumefaciens strains and Burkholderia &lt; RTI ID = 0.0 &gt; glumae) had a IC ₅₀ value represents the growth inhibitory activity against strains appeared to be the 22.5, 1.58 and 33.2 ㎍ / ml, LAL Stony Oh solar nasae ahreom (Ralstonia solanacearum) and the strain Pseudomonas Santo Juve Brassica thoria (Xanthomonas IC ₅₀ values for euvesicatoria) strain is found to be 73.8 and 72.1 ㎍ / ml. In the case of Compound 3, Agrobacterium tumefaciens strain and Ralstonia &lt; RTI ID = 0.0 &gt; Solanacearum strains showed IC ₅₀ values of 1.49 and 75.8 μg / ml. In the case of Compound 4, the IC ₅₀ value of the Agrobacterium tumefaciens strain was found to be 24.8 μg / ml. From this, it can be seen that the compound represented by the formula (I) derived from the Simplexylum lemericola KRICT3 strain (KCTC 11765BP) according to the present invention has an antibacterial activity against various plant pathogenic bacteria.

Therefore, the compounds represented by the formula (I) derived from the Simplexylum lemicolor KRICT3 strain (KCTC 11765BP) according to the present invention are excellent in antibacterial activity, and therefore, they can be used as an antibacterial agent or an anti- And the like.

< Experimental Example  6> Mannosil  Evaluation of antifungal effects of lipid derivatives

In vitro (in order only in accordance with the invention to assess the anti-fungal effect of the lipid derivative nosil vitro ) experiments were performed as follows.

Simplicillium KRICT3 ( Simplicillium was carried out in the same manner as in the step 2 of Experimental Example 3, except that Compound 2 to Compound 4 prepared in Example 2 were used instead of the lamellicola KRICT3 strain (KCTC 11765BP). The results are shown in Fig.

As shown in FIG. 3, the compounds 2 to 4 derived from the simpleisylium lamellicola KRICT3 strain (KCTC 11765BP) according to the present invention are Rhizoctonia solani ), and it is found that the growth inhibiting effect is dependent on the concentration of the compound 2 to the compound 4. [ Further, it was confirmed that the compounds of the compounds 2 to 4 prepared in Example 2 according to the present invention, Rhizoctonia IC ₅₀ values for the solani) strain is found to be 3.22, 1.13 and 1.67 ㎍ / ml, respectively. From this, compounds 2 to 4 according to the present invention can be used as Rhizoctonia solani ) strain of the present invention has excellent antifungal activity.

Therefore, the compounds 2 to 4 represented by the formulas (2) to (4) derived from the Simplexylum lamellicola KRICT3 strain (KCTC 11765BP) according to the present invention are excellent in the antifungal activity, so that the antifungal or antifungal And can be usefully used as a composition for controlling plant diseases.

Claims (10)

Simplicillium lamellicola KRICT3 strain (Accession No .: KCTC 11765BP) extract for plant diseases or pest control.
Simplicillium KRICT3 ( Simplicillium culturing the lamellicola KRICT3 strain (KCTC 11765BP) (step 1); And
The culture solution of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultured in step 1 is selected from the group consisting of methanol, ethanol, acetone, butanol, chloroform and ethyl acetate as one or more organic solvents. A method of preparing an extract of claim 1, simplicity lamelicola KRICT3 strain (KCTC 11765BP) comprising the step (step 2).
Simplicillium KRICT3 ( Simplicillium Lamellicola KRICT3) A composition for controlling plant diseases or pests containing the extract (KCTC 11765BP) as an active ingredient.
Mannosyl lipid derivatives represented by Formula 1 below:
[Chemical Formula 1]

(In the formula 1,
R ₁ is hydrogen or an acetyl group; And
R ₂ is hydrogen,

or

to be).
Simplicillium KRICT3 ( Simplicillium culturing the lamellicola KRICT3 strain (KCTC 11765BP) (step 1);
The culture solution of the Simplicillium lamellicola KRICT3 strain (KCTC 11765BP) cultured in step 1 was extracted with one or more organic solvents selected from the group consisting of methanol, acetone, butanol, chloroform and ethyl acetate. Preparing an extract (step 2);
Performing column chromatography on the extract extracted in step 2 to obtain a fraction (step 3); And
Method of preparing a mannosyl lipid derivative represented by the following formula 1, comprising the step (step 4) of purifying the fraction obtained in step 3 by performing high performance liquid chromatography (HPLC):
[Chemical Formula 1]

(In Formula 1, R ₁ and R ₂ are as defined in claim 4).
6. The method of claim 5,
The column chromatography in the above step 3 was carried out using ethyl acetate / methanol / distilled water (80/10/2, v / v / v), ethyl acetate / methanol / distilled water (80/10/5, v / v / (80/10/8/1, v / v / v), methylene chloride / methanol / distilled water (60/40/10, v / v / v) Wherein the mannosyl lipid derivative is at least one of the following.
6. The method of claim 5,
Wherein the high performance liquid chromatography of step 4 is performed by changing the concentration of methanol from 45% to 100% for up to 30 minutes after the start of the purification.
A composition for controlling plant diseases or pests containing a mannosyl lipid derivative represented by Formula 1 as an active ingredient:
[Chemical Formula 1]

(In Formula 1, R ₁ and R ₂ are as defined in claim 4).
The method according to claim 3 or 8,
The plant disease is acidovorax konjaci), Agrobacterium-to-mepae sense (Agrobacterium tumefaciens ), Burkholderia glumae , Pectobacterium carotobora Subspecies carotobora ( Pectobacterium) carotovora subsp. carotovora ), Pseudomonas syringae pv.lachrymans , Ralstonia solanacearum , Xanthomonas euvesicatoria ), Rhizoctonia solani , Magnaporthe oryzae ), Botrytis cinerea , Phytophthora infestans ), Puccinia recondita , Blue Maria graminis f.sp. Holiday ( Blumeria graminis f.sp. hordei) and sat Collet tree glutamicum coco des (Colletotrichum coccodes) a plant disease, characterized in that caused by a fungus of one selected from the group consisting or pest control composition.
The method according to claim 3 or 8,
The pest is a plant disease or pest control composition characterized by peach aphids ( Myzus persicae ).

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