JPH05286955A - Physiologically active substance nk-04000p, nk-04000q, their production, and herbicide containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To provide the new physiologically active substance useful as a herbicide for agriculture and for non-cultivated lands. CONSTITUTION:The compound of the formula [R1 is -CH2C(=CH2)CH3, -CH2CH (CH3)2; R2 is -(CH2)5CH(CH3)2]. The compound is obtained by culturing a strain belonging to the genus Streptomyces and having an ability to produce the NK-04000P and the NK-04000Q in a proper medium (e.g. sucrose/nitrate salt/ agar) under an aerobic condition, separating the product by a method such as centrifugal method and subsequently purifying the separated product. The substance can be used as an agricultural and horticultural germicide, insecticide, plant growth regulating agent, and acaricide. The dose thereof is 1 to 300g per 100 area expressed in terms of effective ingredient.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a novel antibiotic NK-04.
000P, NK-04000Q, a method for producing the same, and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art As a substance related in structure to the compound of the present invention, there is an antitumor substance BU-3862T described in JP-A-2-72167 (the compound is EP or EP).
ONE CIN as The Journal of Antibioti
It was also published in cs 43 (1) 8-18, 1990. However, the substance of the present invention is different from this. Further, no herbicidal substance whose structure is related to the compound of the present invention is known.

[0003]

In place of synthetic herbicides that have been mainly used in the past, new herbicides obtained as metabolites of microorganisms have been desired for both agricultural and non-agricultural fields.

[0004]

Means for Solving the Problems As a result of carrying out a screening for the herbicidal activity of microbial metabolites, the present inventors have found that one strain belonging to the genus Streptomyces has novel bioactive substances NK-04000P and NK-04.
It has been found that it produces 000Q and that the antibiotic has excellent herbicidal activity. That is, the present invention is: formula

[0005]

[Chemical 4]

(In the formula, R ₁ is —CH ₂ C (═CH ₂ ) CH ₃
Or indicates _{-CH 2 CH (CH 3) 2} , R 2 is - (CH
₂ ) A physiologically active substance represented by ₅ CH (CH ₃ ) ₂ ) 2. formula

[0007]

[Chemical 5]

The physiologically active substance NK-04000 represented by
P 3. formula

[0009]

[Chemical 6]

The physiologically active substance NK-04000 represented by
Q 4. A strain belonging to the genus Streptomyces and having an ability to produce NK-04000P and / or NK-04000Q is cultivated aerobically in an appropriate medium, and from the culture, the formula (2)
And physiologically active substance NK-04000 represented by (3)
A process for producing NK-04000P and NK-04000Q, which comprises obtaining P and / or NK-04000Q.

5. 5. The method according to 4 above, wherein the strain producing the physiologically active substances NK-04000P and NK-04000Q is Streptomyces sp. NK4000 (Mikikoken Co., Ltd. No. 12749) or a mutant or mutant thereof. Physiologically active substance NK-040 represented by formula (2)
A method for producing a physiologically active substance NK-04000Q represented by the formula (3), characterized by reducing 00P

7. Physiologically active substance N represented by formula (1)
The present invention relates to a herbicide containing K-04000P and NK-04000Q as an active ingredient, either alone or in a mixture.

The above novel physiologically active substance NK-04000P
And NK-04000Q, culturing NK-04000P and NK-04000Q-producing bacteria belonging to the genus Streptomyces to obtain physiologically active substances NK-04000P and NK.
-04000Q was produced and accumulated, and the physiologically active substances NK-04000P and NK-04000Q were collected from this culture.
It is obtained by collecting. Physiologically active substance NK-04
A representative example of a 000P and NK-04000Q producer has the following mycological and physiological properties.

1. Morphological properties As a result of observing after 2 weeks at 27 ° C, the aerial hyphae are simply branched and their tips are helical. No formation of sporangia or crusty silk is observed. The spore surface is rough or smooth,
Spores are cylinder type, size 0.7-0.9 × 0.9
Is about 1.2 μm. In addition, 20 or more chains are formed to form spores. 2. Growth in various media Table 1 below shows the growth conditions after 2 weeks at 27 ° C on various media.

[00015]

[Table 1] Media Growth Aerobic hyphae Basal hyphae Soluble pigment Sucrose / Nitrate Moderate Moderate, bright ash Colorless ~ No agar medium ~ Light brown ash Light yellow Glucose / aspara Medium rich, bright ash ~ Gin agar medium Black pale Brown brown (high-glossy) Glycerin / aspara moderately rich, brown-white to black Light brown brown ginger agar medium (high-glossic) Starch / inorganic salt agar Moderate, light ash to light-brown brown medium Bright brown ash Tyrosine agar medium Moderately abundant, brown-white to black, light brown, brownish (high-glossic) Nutrient agar medium Moderate, white, colorless to None, pale yellow, medium, growth, aerial mycelia, basal mycelia, soluble pigment, yeast / malt agar medium, good, moderate to brown-white Black Light brown Plain (high-glossic) Oatmeal agar Medium Good Abundant, Brown White to black Colorless (High (Groscopic) Peptone yeast iron Moderately poor, white, pale yellow, agar medium

3. Physiological properties Appropriate growth range: 20-37 ° C Nitrate reduction: Positive Liquefaction of gelatin (on glucose / peptone / gelatin medium at 20 ° C): Positive Hydrolysis of starch (starch / inorganic salt agar medium): Positive 3. Coagulation of skim milk: negative Peptonization of skim milk: positive Formation of melanin-like pigment: negative 4. Utilization of carbon source (on Pridham Godleybe agar medium) L-arabinose + D-xylose + D-glucose + D-fructose + sucrose + inositol + L-rhamnose + raffinose + D-mannitol +

5. Diaminopimelic acid in the cell wall LL-diaminopimelic acid. To summarize the above,
This strain has a cell wall of LL-diaminopimelic acid, and according to the method of the International Streptomyces genus project (abbreviated as ISP), the morphology of sporulating hypha belongs to section spirals and the spore surface is rough. Alternatively, the smooth, mature hyphae are gray color series and do not produce melanin-like pigments. Also, almost no pigment is produced in the medium. The color of basal hyphae is light brown or light yellow. L-arabinose, D-glucose, D-fructose, sucrose, inositol, L-rhamnose, raffinose, D-mannose, D-mannitol and D-xylose are used as carbon sources.

Based on the above properties, Bergey's Manual of Determinative Bacte, edited by R. E. Buffanan and N. Gibbons.
riology) 8th edition, 1974, and as a result of the search, it was found that the above strain NK04000 belongs to the genus Streptomyces. Therefore, this strain was named Streptomyces sp. NK04000. The strain has been deposited with the Institute of Microbial Technology, National Institute of Advanced Industrial Science and Technology, as Micromachine Research Institute No. 12749.

The physiologically active substance of the present invention is the above-mentioned NK040.
It can be advantageously produced using strain 00. In general, actinomycetes are naturally or artificially susceptible to mutation in their properties, and the physiologically active substance of the present invention can be produced by using a mutant strain of NK04000 strain. It can also be produced by using various known bacteria belonging to the genus Mrs.

According to the invention, NK-04000P and NK
To produce 0400Q, the strain is first aerobically cultivated in a medium containing nutrients that actinomycetes can utilize.
As the nutrient source, known ones that have been conventionally used for culturing actinomycetes can be used.For example, as the carbon source, glucose, fructose, glycerin, sucrose, dextrin, galactose, an organic acid or the like alone or in combination. Can be used. Inorganic and organic nitrogen sources include ammonium chloride, ammonium sulfate, urea, ammonium nitrate, sodium nitrate, peptone, meat extract, yeast extract, dry yeast, corn steep liquor, soybean powder, cottonseed oil residue, casamino acid, pact soyton, soluble, vegetable , Protein, oatmeal and the like can be used alone or in combination. In addition, inorganic salts such as sodium chloride, calcium carbonate, magnesium sulfate, copper sulfate, iron sulfate, zinc sulfate, manganese chloride, and phosphate can be added as required, as well as organic substances such as amino acids, vitamins, nucleic acids and inorganic substances. Can be added appropriately. Liquid culture method,
Particularly, the deep agitation culture method is most suitable. Culture temperature is 20
It is desirable to carry out the culture at ˜45 ° C. and at a slightly acidic or slightly alkaline pH. In liquid culture, when the culture is generally performed for 1 to 5 days, the NK-04000P and NK-04000Q substances are produced and accumulated in the culture medium. When the production amount in the culture solution reaches the maximum, the culture is stopped, and the target product is purified and isolated from the culture solution obtained by filtering the cells.

NK-04000P and N from culture
For purification and isolation of K-04000Q, a method for separation and purification generally used for isolating a microbial metabolite from its culture solution is used. For example, the culture is separated into a filtrate (supernatant) and a precipitate by a centrifugation method or a filtration method. The filtrate is adsorbed on the porous polymer resin, the resin is washed with water and then eluted with acetone, and the precipitate is extracted with a water-soluble solvent such as acetone or methanol, and the obtained solution is used as it is or after concentration with water. Dissolves in general organic solvents that are difficult to mix,
By concentrating under reduced pressure, an oily substance containing NK-04000P and NK-04000Q is obtained. The crude substance is a known method usually used for purification of a fat-soluble substance,
That is, purification is performed by appropriately combining solvent distribution, chromatography using silica gel, gel filtration method, high performance liquid chromatography and the like. As a suitable example for purification, the above crude material is partitioned with hexane and acetonitrile, the acetonitrile layer is concentrated, and the concentrated residue is subjected to silica gel chromatography using hexane-acetone as an eluent. The obtained active fraction was concentrated and, if necessary, subjected to silica gel chromatography again, and the obtained active fraction was concentrated to give Sephadex LH-
The thus obtained active fraction was concentrated through a 20-molecular sieve column, and fractionated by reverse phase high performance liquid chromatography using an ODS column to obtain NK-04000.
P and NK-04000Q can be obtained alone and / or as a mixture.

NK-04000Q is also NK-0400
It can also be obtained by reducing 0P. For example, NK-04000P is catalytically hydrogenated by using a suitable catalyst such as 5 to 20% Pd-C under a hydrogen stream at room temperature and under normal pressure, if necessary, by heating and pressurizing to obtain N.
K-04000Q can be obtained.

NK-0400 obtained as described above
The physicochemical properties of 0P and NK-04000Q are shown below.

NK-04000P: (1) Appearance Colorless sticky oil (2) Specific irradiance [α] _D ²⁴ + 26 ± 3 ° (c0.1 MeOH) (3) High resolution mass spectrum (FABMS method) MH ⁺ Actual value 413.2666 Calculated value 413.2652 (as C ₂₁ H ₃₇ N ₂ O ₆ ) (4) Molecular formula C ₂₁ H ₃₆ N ₂ O ₆ (5) Ultraviolet absorption spectrum (in methanol) 202 ± 3 nm (6) Red external absorption spectrum (KCl) (Fig. 1) showing the main absorption wave numbers (cm ^-1 ) 3301, 2928, 1722, 1644, 1536,
1462, 1382, 1249, 1050, 899

(7) ¹³ C-nuclear magnetic resonance spectrum (1
00 MHz) in deuterated chloroform (Fig. 3) (8) 1H-nuclear magnetic resonance spectrum (400 MHz) in deuterated chloroform (Fig. 5) (9) Solubility Easy dissolution: methanol, acetonitrile, acetone, chloroform, ethyl acetate, sparingly soluble: Water (10) Thin layer chromatography Silica gel thin layer (Kiesel Gel 60F254 0.5
mm Merck), n-hexane: acetone (1:
When developed using 1), the Rf value is around 0.3. (11) Color reaction Positive when heated to vanillin-sulfuric acid.

NK-04000Q: (1) Appearance Colorless sticky oil (2) Specific irradiance [α] _D ²⁴ + 34 ± 3 ° (c0.1 MeOH) (3) High resolution mass spectrum (FABMS method) MH ⁺ Actual value 415.2793 Calculated value 415.2808 (as C ₂₁ H ₃₉ N ₂ O ₆ ) (4) Molecular formula C ₂₁ H ₃₈ N ₂ O ₆ (5) Ultraviolet absorption spectrum (in methanol) 202 ± 3 nm (6) Red external absorption spectrum (KCl) (Fig. 2) showing main absorption wave numbers (cm ^-1 ) 3292, 2956, 1718, 1645, 1540,
1465, 1386, 1048, 914

(7) ¹³ C-nuclear magnetic resonance spectrum (1
00 MHz) in deuterated chloroform (Fig. 4) (8) 1H-nuclear magnetic resonance spectrum (400 MHz) in deuterated chloroform (Fig. 6) (9) Solubility: Soluble: methanol, acetonitrile, acetone, chloroform, ethyl acetate, sparingly soluble: Water (10) Thin layer chromatography Silica gel thin layer (Kiesel Gel 60F254 0.5
mm Merck), n-hexane: acetone (1:
When developed using 1), the Rf value is around 0.3. (11) Color reaction Positive when heated to vanillin-sulfuric acid.

Chemical structure: The novel physiologically active substances NK-04000P and NK-04000Q according to the present invention have the chemical structural formulas shown in the above formulas (2) and (3). These chemical structural formulas were determined as follows. N
NK-0400 according to the proton nuclear magnetic resonance spectrum, carbon-13 nuclear magnetic resonance spectrum, infrared absorption spectrum, and ultraviolet absorption spectrum of K-04000P.
0P is the known substance Eponemycin (the journal of an
tibiotics 43 (1) 8-18, 1990). From the high resolution mass spectrum, the molecular formula was determined to be C ₂₁ H ₃₆ N ₂ O ₆ . This molecular formula has one more methylene group (CH2) than Eponemycin, and its position is determined by the various spectra and H-H COSY.
It was determined by the two-dimensional NMR spectrum as shown in formula (2). The structure of NK-04000Q was determined to be C ₂₁ H ₃₈ N ₂ O ₆ by a high resolution mass spectrum, and NK-04000P was determined by a proton nuclear magnetic resonance spectrum, a carbon 13 nuclear magnetic resonance spectrum, an infrared absorption spectrum and an ultraviolet absorption spectrum. Was determined to be the structure of formula (3), which was found to be the dihydro form of the reduced form of endomethylene of formula (2).

Physiologically active substance NK-04000P of the present invention
When using NK-04000Q as a herbicide for agricultural and horticultural use, a plant growth regulator, and a fungicide, in the field of agrochemical production, it may be used as it is or in combination with an agrochemical adjuvant in order to promote or stabilize the effect. Depending on the commonly used method, powders, fine granules, granules, wettable powders, flowables, microcapsules, oils, aerosols, fumigants for heating (mosquito coils, electric mosquito coils, etc.), fog, etc. It can be used in any formulation form such as an agent, a non-heating fumigant, and a poison bait. These various formulations can be used directly as they are in actual use, or can be diluted with water to a desired concentration and used. In addition, these preparations contain the physiologically active substance NK-04 of the present invention as an active ingredient.
000P and NK-04000Q from 0.1 to 99.9
%, Preferably 0.2 to 80%, is adjusted according to a usual formulation method.

The above-mentioned pesticide auxiliary agent is a carrier (diluent)
And other auxiliary agents such as spreading agents, emulsifying agents, wetting agents, dispersing agents, fixing agents, disintegrating agents and the like.
Among the carriers, liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, and methylnaphthalene. , Cyclohexane, animal and vegetable oils, fatty acids, fatty acid esters, and petroleum fractions such as kerosene and light oil.

Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina and sawdust. As the emulsifier or dispersant, a surfactant is usually used, and examples thereof include anionic surfactants such as higher alcohol sodium sulfate, stearyl tolylmethylammonium chloride, polyoxyethylene alkylphenyl ether, and ularyl betaine, and cationic surfactants. Examples thereof include an activator, a nonionic surfactant, and a zwitterionic surfactant.

Examples of the spreading agent include polyoxyethylene nonylphenyl ether and polyoxyethylene uralyl ether, and examples of the wetting agent include polyoxyethylene nonylphenyl ether dialkylsulfosuccinate and the like. Examples thereof include carboxymethyl cellulose and polyvinyl alcohol, and examples of the disintegrator include sodium lignin sulfonate and sodium lauryl sulfate. Not only can each of the formulations be used alone, but also other agricultural and horticultural fungicides,
It can also be used as a mixture with an insecticide, a plant growth regulator and an acaricide.

NK-04000P and NK- of the present invention
When 04000Q is applied as a herbicide for agricultural and horticultural use, a plant growth regulator, and a fungicide, the application amount is usually 1 to 300 g, preferably 15 to 200 g per 10 ares as an active ingredient amount.
Is used. The application concentration is preferably 0.001 to 0.4% when diluted with water such as a wettable powder or a liquid preparation and applied. Further, in the case of powders, granules, fine granules, etc., it may vary depending on the dosage form, method of use, timing and other conditions, and the concentration may be changed without increasing or decreasing the above range.

[0034]

EXAMPLES Examples of the present invention will be shown below, but these are merely examples and do not limit the present invention in any way, and various modifications are possible.

Production Example 1 Glycerin 2%, soluble starch 2%, soybean flour 2%, salt 0.3% in a 500 ml Erlenmeyer flask for rotary shaker.
100 ml of the medium (pH 7.0) was dispensed at 120 ° C for 2
It was autoclaved for 0 minutes. This is NK04000
Inoculate 1 platinum loop of the strain (Microtech Lab. No. 12749),
It was shaken at 27 ° C., 220 rpm for 2 days. Separately, in a 500 ml Erlenmeyer flask for rotary type shaker, glycerin 2%, soluble starch 2%, soybean flour 2%, salt 0.3.
% Medium (pH 7.0) 100ml, 120 ℃,
2 ml each of the above culture solution was transferred to 98 flasks autoclaved for 20 minutes, and shake-cultured at 27 ° C. under 220 rpm for 4 days. The culture was filtered. The culture solution is filtered and separated into a filtrate and cells, and the filtrate is DIAION HP-
20 (Mitsubishi Kasei Kogyo Co., Ltd.), and after washing with 5 liters of water followed by 3 liters of 50% acetone water,
It was eluted with 4 liters of acetone. Approximately 300 eluate
Concentrate to ml and extract with 2 liters of ethyl acetate. The extract is washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 0.8 g of crude substance (1). The cells were extracted with 10 liters of acetone and filtered to remove the cells,
The filtrate is concentrated to about 3 liters, extracted with 6 liters of ethyl acetate, the organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated residue was partitioned with hexane and acetonitrile, and the acetonitrile layer was concentrated to obtain 4.2 g of a crude substance (2). Crude material (1)
And silica gel 60 (Merck)
Hexane-acetone was applied to the column chromatography using as a solvent. 0.43 g of the obtained active fraction was applied to a column of Sephadex LH-20 (Pharmacia) with methanol as an eluent. The obtained active fraction (0.34 g) was dissolved in methanol, and the mixture was fractionated little by little by reverse phase liquid chromatography. The column used is W
aters μBondasphare 5C18 19 × 150, solvent conditions are methanol: distilled water 70:30, flow rate 9.6 ml
/ Min. UV212nm with refractometer or UV meter
Alternatively, the peak detected at UV 220 nm is collected.
NK-04000P is eluted at an elution time of 12 minutes, and NK-04000Q is eluted at about 14.3 minutes. The elution time varies depending on the lot of the column and the condition of use. Separately collect each peak component under the same conditions,
35 mg of NK-04000P and 1 of NK-04000Q
7 mg was obtained.

Production Example 2 NK-04000P (5 mg) was reacted in methanol in a hydrogen stream at room temperature in the presence of 20% Pd / C for 10 hours at atmospheric pressure, filtered to remove the catalyst, and the filtrate was obtained. After concentration under reduced pressure, the residue was applied to a Sephadex LH-20 column, and then fractionated by the high performance liquid chromatography shown in Production Example 1 to obtain NK-04000B (1 mg).

Formulation Example 1 Agro-horticultural wettable powder 20 parts of the present invention NK-04000P, 75 parts of kaolin, 3 parts of higher alcohol sodium sulfate and 2 parts of sodium polyacrylate are mixed and ground to obtain a wettable powder. Formulation Example 2 Agricultural and Horticultural Emulsion 30 parts of NK-04000Q of the present invention was dissolved in 53 parts of xylene, and 17 parts of a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzene sulfonate (8: 2) was mixed and dissolved to form an emulsion. To do. This product is diluted with water and used as an emulsion.

Formulation Example 3 Powder for agricultural and horticultural use NK-04000P of the present invention 1 part of 97 parts of a mixture of talc and calcium carbonate (1: 1) was added and mixed and ground to be sufficiently evenly dispersed, and then silicic acid anhydride was added. Add 2 parts,
Mix and pulverize to make powder. Disperse this product as it is before use. Formulation Example 4 Agricultural and Horticultural Granules 2 parts of the present invention NK-04000Q is mixed with 48 parts of bentonite fine powder, 48 parts of talc, and 2 parts of sodium lignin sulfonate, and then water is added and kneaded until uniform.
Next, the mixture is granulated through an injection molding machine and passed through a granulator and a dryer to obtain granules having a particle size of 0.6 to 1 mm. This product is used by directly sprinkling it on paddy fields and soil surfaces. Next is NK
The biological activity of −04000P and NK-04000Q is described.

Test Example 1 Herbicidal effect of NK-04000P and NK-04000Q Test method Weeds, corn and soybean seeds were sown in plastic pots with a diameter of 10 cm and a depth of 12 cm, respectively. NK-04000P and N
A predetermined amount of the diluted solution of K-04000Q was sprayed over the entire foliage. In the investigation, 12 days after the treatment, the herbicidal effect was observed and investigated using an index of 6 levels from 0 to 5. The results are shown in Table 2. Herbicidal effect of NK-04000P

[0040]

[Table 2]

Herbicidal effect 5 100% mortality 2 40% mortality 4 80% mortality 1 20% mortality 2 60% mortality 0 No effect Herbicidal effect of NK-04000Q

[0042]

[Table 3]

Herbicidal effect 5 100% dead 2 40% dead 4 80% dead 1 20% dead 2 60% dead 0 No effect

[0044]

According to the present invention, the physiologically active substance NK-040
00P and NK-04000Q are provided, and the bioactive substance has excellent herbicidal activity.

[Brief description of drawings]

FIG. 1 shows an infrared absorption spectrum (KCl method) of NK-04000P.

FIG. 2 shows an infrared absorption spectrum (KCl method) of NK-04000Q.

FIG. 3 shows a ¹³ C-nuclear magnetic resonance spectrum of NK-04000P (in CDCl ₃ ).

FIG. 4 shows a ¹³ C-nuclear magnetic resonance spectrum (in CDCl ₃ ) of NK-04000Q.

FIG. 5 shows the ¹ H-nuclear magnetic resonance spectrum (in CDCl ₃ ) of NK-04000P.

FIG. 6 shows the ¹ H-nuclear magnetic resonance spectrum (in CDCl ₃ ) of NK-04000Q.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Internal reference number FI technical display location C12R 1: 465) (72) Inventor Tatsumi Hayaoka 1039 Kamiochiai, Yono City, Saitama Prefecture (72) Inventor Nakagawa Taizo 4-671-3 Mitsuhashi, Omiya City, Saitama Prefecture

Claims (7)

[Claims] 1. The formula: (In the formula, R ₁ is —CH ₂ C (═CH ₂ ) CH ₃ or —CH
₂ CH (CH ₃₎ shows the _2, R ₂ is _{- (CH 2) 5 CH (} C
H ₃ ) ₂ ) which represents a physiologically active substance. 2. The formula: The physiologically active substance NK-040 according to claim 1
00P. 3. The formula: The physiologically active substance NK-040 according to claim 1
00Q. 4. NK-0400 belonging to the genus Streptomyces
A strain capable of producing 0P and / or NK-04000Q is aerobically cultured in an appropriate medium, and the culture is expressed by the formulas (2) and (3) according to claims 2 and 3. NK-0, which is characterized by obtaining a physiologically active substance NK-04000P and / or NK-04000Q
Production method for 4000P and NK-04000Q. 5. Bioactive substances NK-04000P and N
The method according to claim 4, wherein the strain producing K-04000Q is Streptomyces sp. NK04000 or a mutant or mutant thereof. 6. A physiologically active substance represented by the formula (3) according to claim 3, which reduces the physiologically active substance NK-04000P represented by the formula (2) according to claim 2. N
K-04000Q manufacturing method. 7. A physiologically active substance NK-04000P and / or NK-0400 represented by the formula (1) according to claim 1.
A herbicide containing 0Q as an active ingredient.