JPS58116686A - Octane derivatives, their production methods and their uses - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] law and agricultural fungicides containing the same as an active ingredient.

As the producing microorganism of the novel antibiotic Snee 4228 of the present invention, a microorganism that accumulates a sufficient amount of the antibiotic in its culture is used. There is a strain of Streptomyces sp. 814228 isolated from the forest in Miyakonojo City. The orchidological properties of this strain are shown below.

■ Morphology (11 Branching method of spore-forming hyphae Simple branching (2) Morphology of spore-forming hyphae Straight (3) Number of spores 10 or more spores Chained (41 Surface chain of spores Smooth (5) Size of spores 075μ?lIX1.25μ
m (6) Flagellated spores None (7) Spore paste None (8) Gradual position of sporophyte On aerial hyphae (9) Sclerotium formation None ■1 Growth status on each Yuzu medium (1) Nutrient agar medium Growth: somewhat rapid, The back side is pale yellow at the periphery (2.5 y,
as/s), transparent sterile hyphae in the center: no settlement, soluble pigment: not produced 4-(2) Growth on glycerin/asparagine agar medium: somewhat poor, back side light reddish brown (10R).

2) Aerial mycelium grows in powder form on the two surfaces and is slightly reddish gray (
5YR, 6 people) Soluble pigment: Not produced (3) Growth on sucrose/nitrate agar medium: Normal growth, dark brown on the back side (7.5R, /, 5)
Bright reddish brown in the center (7.5 R, /6
) Aerial mycelium: sparsely attached, but relatively good on the periphery, slightly reddish gray (25YR, 7/2) Soluble pigment: pale reddish brown (4) Glutose/asparagine agar medium Growth: rather poor, back side is ocher (10Y11.

5/6) Aerial fungi: A powdery, slightly reddish gray color (
5yRt /2) Soluble pigment: Not produced (5) Starch/inorganic agar medium Growth: Normal growth, ivory color (5yRt/2) around back ti1
yt F'5/6>r White aerial mycelia in the center, aquatic powdery on the knee surface, grayish white (111R).

8/1) Soluble pigment: Produced (6) Growth on tyrosine agar medium: Normal growth, the underside is brown (2,5YR, /
2) Aerial mycelium actively grows on the knee surface and is gray (10B).

5/1), velvety soluble pigment: light brown (7) #mother/malt agar medium growth: normal growth is L, m is ocher (10YRI
/6) Aerial bacteria: Scaly, but relatively well settled in the peripheral areas, gray (IOYR, /1) Soluble pigment: Pale yellow (8) Oatmeal agar medium W: Normal growth, Yellow ocher (75
(Y
t'/1) Soluble pigment: pale yellow ■Physiological properties (1) Growth temperature range Growth temperature = 20-45°C2 Suitable growth temperature = 55-42°C
(Both bacterial cells and medium are yellow at around 40°C) (2) Liquefaction of gelatin Liquefaction (3) Hydrolysis of starch Strong decomposition (4) Coagulation of skim milk, peptonization No coagulation, no peptonization ( (5) Production of melanin-like pigment Both peptone yeast, iron agar medium, and tyrosine agar medium turn black ■ Assimilable carbon source Growth Carbon source Growth L-arabinose 廿 Inositol 廿 - Xylose 廿L-rhamnose
廿11 D-Dulcose 廿 Raffinose
廿D-7lactose + D-mannitol 廿Sucrose 廿No addition
The mycological properties of the Streptomyces sp. S. 4228 strain described above are summarized as follows.

0) Gray aerial hyphae are attached (2) Aerial hyphae are single-line branched and target-shaped (3) Spore plane is smooth (4) Spores are linked with 10 or more spores (5) Melanin-like Produces pigment (61 #R fat raw milk does not coagulate and does not peptonize (7
) It decomposes starch well (8) It does not produce any characteristic pigments such as light yellow or pale brown pigments (9) It is known as a known strain of Streptococcus that has the following properties: Mrs-7 Eoplubreus (5tre tomcesp
haeopurpureus, Internationali
onal Journal of Systemati
c Bactθr-1o10g7, Volume 5, Page 35, 1968). However, oatmeal, glycerin.

On the asparagine, sucrose, nitrate, and other occlusive media, the underside of the Snee 4228 strain is pale yellow or pale brown, whereas the underside of Streptomyces pheopulpureus is reddish brown. In addition, the pigment produced on the above medium is pale yellow to pale brown for the Snee 4228 strain, while Streptomyces pheopurupuleus is pale brown to reddish brown.

Therefore, based on these facts, the Snee 4228 strain is considered to be a strain of 4 Nostreptomyces and 7 Eoburupres, but it is considered to be an unidentified species. Therefore, the present inventor developed this strain of Streptomyces sp.
It was named 8 stocks. This strain is Streptomyces sp. S. 422a strain and 17, which have been deposited at the Institute of Technology.
Its accession number is FEBM P-6198.

In the present invention, the antibiotic E3
Anything capable of producing -4228 can be used.

The novel antibiotic Snee 4228 can be obtained by culturing the above-described antibiotic Snee 4228-producing bacteria and collecting the antibiotic from the culture.

Cultivation is carried out using a medium containing nutrients that can be utilized by the microorganisms, such as glucose, sucrose, starch, starch syrup, dextrin, glycerin, etc., can be used as carbon sources. Further, as the nitrogen source, ammonium nitrate, ammonium sulfate, meat extract, corn steep liquor, peptone, dried yeast, corn gluten, soy flour, and other organic or inorganic nitrogen compounds can be used. Other inorganic salts such as salt, phosphates, calcium, zinc, magnesium, and iron may be added as necessary, and substances unnecessary for the production of 1-t% Antibiotic S-4228 may be added to promote the growth of microorganisms. It can be added as appropriate.

Cultivation is carried out under aerobic conditions and usually
The accumulation of antibiotic isany 228 reaches a maximum of 1 by carrying out the treatment at a temperature of 64°C, preferably 28-52°C, for 6-10 days, preferably tj: 4-6 days.

Antibiotic SI-4228 is not only accumulated in the cultured serum, but also accumulated in the bacterial cells.

Since the antibiotic Snee 4228 of the present invention has the 1°11 chemical properties described below, extraction and purification are carried out in consideration of these properties. That is, 1) an organic solvent such as ethyl acetate is added to the culture to perform extraction, and the resulting extract is concentrated by an appropriate means and then transferred using benzene. Next, the filtrate of the culture is subjected to ion exchange resin or activated carbon adsorption, followed by elution, fractional purification with a silica gel column as described above, and further gel filtration. Antibiotic Snee 4228 purified by methods such as crystallization can be obtained.

The antibiotic Snee 4228 thus obtained has all the following physical and chemical properties.

(a) Elemental analysis value 0: 62.1%, H near, 4%, N: 0% (b) Molecular weight 4
80@3σEitJ, solvent: chlorophor → (c)
Infrared absorption spectrum As shown in Figure 1.

b) Ultraviolet absorption spectrum as shown in Figure 2.

(e) Nuclear magnetic resonance spectrum As shown in Figure 5.

11- Soluble in ethyl, benzene, ether, chloroform, carbon tetrachloride, insoluble in water, n-hexane ←) Neutral (by lt gas phoresis) (IJ) Color reaction Ferric chloride, 2,4 - Characteristic for dinitrophenylhydrazine, negative for ninhydrin (nu)MIII points 114
~116°C) Color of the substance The minimum inhibitory concentration for various microorganisms determined by the multiple dilution method using a potato gluten agar medium for the white needle-shaped antibiotic Qh quality Snee 4228 is as follows.

Escherichia coli 〉100 (Each
erichia coli ) Bacillus subtilis 〉100 (Bacillus
5ubtilia) Erwinia Aloidea
〉100()Grwinia ar
oidea ) 12- Table 2 (Continued) Satucharomyces cerevisiae 100
(IPusarium oxysporum) No.
Table 2 (Continued) Antibiotic of the present invention Snee422s&J: Useful as an agricultural fungicide, medicine, etc., and is effective against gray mold on bamboo.

It shows a sufficient control effect against charcoal disease, sheath blight, and rice blast disease at a dosage of IJ-(drug) compared to the existing fungicides in W4.

Even when the antibiotic S-422B, which has the above-mentioned physicochemical properties and biological properties, is compared with the known substance 'L, there is no corresponding comparison, and the actual product is a new antibiotic.

Next, examples of the present invention will be shown.

□ Glucose 3% adjusted to PH Otsu 0g, polypeptone 0
, / %, NaC, eθ, θg%, K2T(PO4(
')-/, 10β of a medium containing 2% Corn Stape Liquor and Dachi was dispensed into 700 Meyer flasks each having a volume of 0θml, and sterilized at 20°C for minutes. In this medium, Streptomyces sp.
r-11,228 strain (FERM, P-Otsu/9 g) was inoculated from the whole slant culture medium/loop. After inoculation, the culture was incubated with rotary shaking at 32°C for 9 hours (rotation speed: 200 r, pom, l). This culture was collected, and ethyl acetate was added to the culture for 2 hours.
After stirring for 0 minutes, the ethyl acetate layer was collected. Anhydrous sulfuric acid (IJ) was added to the ethyl acetate layer for dehydration, and the mixture was concentrated to dryness under reduced pressure at θ°C.

1/1 of benzene was added to the concentrate, and insoluble materials were removed by filtration. The solution was concentrated under reduced pressure to 3 ml.

Benzene was added to 30 g of silica gel (manufactured by Merck & Co., Ltd.), and the mixture was packed into a glass column of 100 mL, and the concentrate was placed on the top end of the column to be adsorbed. Next, a solution of n-hexane:acetone (/, ff:/) was poured into the flask, and a fraction collector was used to collect a 15-minute fraction eluted with a 2:1 g substance. Both portions were concentrated under reduced pressure at 0°C to dryness, and then 3 ml of chloroborm was added and dissolved.

On the other hand, after being dispersed in Sephatex LH-20't chloroform, it was packed into a glass column with a diameter of 15 m and a height of 7 m. A chloroform solution containing 8-12 g of the substance was placed on the top of the column, and purification using molecular sieves was carried out using chloroform as a developing solution.

SI-II, the fraction containing 22 g of substance was collected using a horn collector, concentrated to dryness, a small amount of acetone was added, and further n-hexane was added, and the mixture was left indoors for several days. Needle-shaped crystals were obtained. This substance had the physicochemical properties described above.

Example λ PH4, gK adjusted glucose 4%, polypeptone θ
,/%, yeast extract θ, Sti, Na(J θ, θg
Chi, K2HPO40, / gchi, Corn Steep
Medium 3θ containing 0% liquor! After sterilization, the seed culture (Streptomyces sp. ST-
1122g, FERvp-Otsu/9g) 200
rnl', c-contact 15 types were made. After inoculation, sterile air was aerated at 30°C/min at 32°C, and agitation culture was performed at ly 00 r-plm for qt hours.

Culture crest, sterilized f solution filled with ion exchange resin Amberlite
Passed through a 7m long column to absorb the active ingredients.
.

At the edge, the adsorbed active ingredient was eluted by flowing 20β acetone. The eluate was reduced at θ° C. and concentrated under pressure to obtain a solid substance with a yield of 7.27. Chloroborum was added to the solid, and both the dissolved parts were collected and concentrated to dryness at 140°C to obtain 62 g of a solid.

On the other hand, Sephadex LH-2θ was dispersed in chloroform and packed into a 7.5 m long glass column. Place a small amount of the solid dissolved in chloroform on the top of the column, add chloroborm as a developing solution, and collect the fraction:
collected. Both fractions were concentrated, and the purification using Sephadex LH-no-θ was repeated seven times in the same manner.
．． 2g? The I-containing fractions were collected. Both components were concentrated to dryness, then a small amount of acetone was added to dissolve them, and n-hexane was added and left indoors for λ days: 2.
．． Needle-shaped crystals of 20 In9 were obtained.

Example 3 (Emulsion) FiT-11, 2, 2g material 0 years ago! Tsu, Kishi L・
Mix and dissolve the Ng S part, the bottle 30θ, and the Dx (J1! manufactured by Kuniyoshi Kogyo Co., Ltd.)/Yube. The basic rule is diluted with water ρ, ton 00 to lIo, o o o times and sprayed. .

Example 5 (Irrigation agent) Sl-ll Muba substance/θ part, Tetarsient Otsu θ (manufactured by Lion Corporation) 0.9 parts, Tsurupol g00A (Toho Chemical Industry Co., Ltd. ff) /, g part, Zeekrite (Zikrite) (manufactured by Kogyosha) g'7. ,? Mix and grind the parts.

The main formula is diluted 500~/θ, 000 times with water and sprayed.

Test Example / Preventive effect test against botrytis gray mold of fH-l122g' rostrum Green beans on the 30th day of sowing (variety: Keystone).

Spray a chemical containing the test compound at a predetermined concentration on 3 plants (potted plants), and spray Rntritis C1nere on the ridge for 2'1 hour after spraying.
Spore suspension of a (/X/06 pieces/ml)
paper disks with a diameter of g fins were placed on the surface of leaves of 7 French bean plants. For comparison, bacteria were inoculated using the same method on a strain to which no chemicals were sprayed.

The green beans were kept in a constant temperature and humidity tank with a temperature of 200 parts and a humidity of 10θ, and after 5 days, the major axis of necrosis formed on the leaf surface was measured from the underside of the leaf, and the disease severity was calculated using the following method. .

Table 3 shows the test results.

n: Long axis of the lesion in the test collection (■) 11: Unsprayed leaves 〃 Table 3 Test example Preventive effect test on Konas gray mold and green pepper gray mold Three plants each of green pepper (potted plant) and green pepper (variety Ninuace, potted plant) were sprayed with the chemical at a predetermined concentration, and the mycelium of Botritis C1nerea, which had been grown in advance on a special celestial medium, was grown to a diameter of 1 liter.
Two leaves per seven plants were punched out with IIIllI cork polar. Thereafter, a test was conducted in the same manner as in Test Example.

The results are shown in Tables G, D, and D.

Test Example 3 Preventive effect test on Kirari charcoal scar chest A drug containing the test compound at a predetermined concentration was sprayed on 3 Kirari (variety: Ochiai, potted plants) plants on the 7th day of sowing.
om spore suspension (/× 706 spores/me). For comparison, bacteria were also sprayed using the same method on strains that were not sprayed with chemicals.

Thereafter, they were kept in a constant temperature, separate room tank at a temperature of 23° C. and a humidity of 700% for 9 days, and the degree of disease susceptibility was calculated by the following method. The results are shown in Table B.

+, b, c, d each score θ) leaf description, tsu: no disease symptoms/: disease symptoms less than 10%, 2: disease symptoms 70% or more, SO less than 3: disease symptoms, ta 0 More than 1, less than 75%: Disease symptoms are 7S% or more = 23- Test example - Preventive effect test against sheath blight A chemical solution of a prescribed concentration was sprayed on the cut leaves of Japanese bean / θ S weeks after sowing. It was placed in a greenhouse at G'O and left for 2 hours.

Meanwhile, on potato glucose agar medium, 2 g
Rice sheath blight fungus (Pell 1 cu.
l-arja 8asakjil bacterial flora periphery to diameter 11
Punch out with wn1 cork polar, spray the above chemical solution, 2
After 1 hour, inoculate ten broad bean leaves and inoculate 2 g of S in a greenhouse at ℃℃.
The condition of the lesions was observed after holding for several days. The results are shown in Table 7.

Table 7 Test against sheath blight 5x-11, :), 2g substance 100
0 (emulsion) Otsu00 30 / /ta 3 Validamycin, Otsu0 /30
3 Test Example S 24-- Preventive effect test against rice blast disease Rice at the leaf stage (variety Norin No. 29) 4'H (/planted 10 pots)
A chemical solution with a predetermined concentration of K was sprayed and air-dried. After air drying, Pyriculhrja aryzae
After spraying a spore suspension (5 ? The control value was calculated relative to the area. The results are shown in Table g.

Table g Test drugs against rice blast disease Agent Concentration a,) Control value 5T-lI
-, 22g substance 700 9g, 2(
Emulsion) Da0 9'1.3 no θ
7 Otsu, λ Hinosan 3θθ 9,? Patent Applicant Idemitsu Kosan Co., Ltd. Agent Patent Attorney Kubo 1) Fujibe Procedural Amendment (Method) (Voluntary) January 12, 1980 Commissioner of the Japan Patent Office Shima 1) Haruki Tono 1. Indication of the case and its Relationship with the case of a person amending agricultural fungicide i as an active ingredient Patent applicant: Idemitsu Kosan Co., Ltd. 4, Agent: 1-10 Kyobashi, Chuo-ku, Tokyo 104 List of documents attached to the application Also, Drawing 6 and the contents of the amendment are corrected as shown in the attached document.

(2) Submit an engraving of the drawings (with no changes to the contents).

Inventory of Z salary documents T11 Request for correction 1 copy (2) Drawings 1 copy (or more) Procedural amendment (voluntary) January 12, 1980 Commissioner of the Japan Patent Office Shima 1) Haruki End- 1. Indication of the case Showa Patent Review 2 filed on December 29, 1956, Name of Invention: New Antibiotic S-4228 Substance, Its Manufacturing Method, and Agricultural Paste Fungicide Using the Substance as an Active Ingredient 5 Relation to the Amendment Case. Akito Idemitsu, Kosan Co., Ltd. 4, Agent 10-5, Kyobashi 1-1, Chuo-ku, Totobu 104, Sen 1 of the claims of the specification subject to amendment 1 Detailed description of the invention and drawings Brief explanation (1) Correct the claims uH as shown in the attached sheet.

+2+light n++sho g 5 gekkokara 5 row no rcz,
5 y, a5/6)” to [(2,5Y, EL
5/6, Munsell Book of C
By olor. (The same applies hereinafter)".

(31, page 91, line 4 from the bottom, page 1, page 55) is corrected to ``page 1, 558''.

(4) r+7sJ on the second line from the bottom of page 12 is 1+4°
” is corrected.

(5) 5th line from the bottom of the 14th member “Bilicularia ■
L anus) (poryzae) (6)
In the 7th line from the bottom of No. 15, "charcoal spasm" is corrected to "disease."

(7) The 16th line of the 16th line, 11th line, the first bond was stirred, and then it was corrected to ``11 was pressed.''

(8) 1-Amberlight XA on page 18, lines 4-5
D-2,8/! , J[Amberlight XAD~2,8
Corrected to tJ.

1- (9) Botritis O1, page 20, bottom line
n@rea J [Botrytis 01nerea
Correct J by 1.

(IQ IW) 1 spore suspension (IX 10'/+nl) of the second spore with a paper disk of 8 diameter attached to -1
) attached to a paper disk with a diameter of 8 mm.
Correct.

011 4th line from the 21st nobleman [Botritis
01nerea hyphae” to “Botrytia 01n
Correct to bacterial flora J of area.

Roka, page 25, line 4, “Ineimochi disease fungus (1 mouthful” 1-
Pyricularia oryzae) J [Pyricularia oryzae]
Correct to J.

O; ri, page 25, line 9 Correct to.

04) Added the following sentence next to Table 8 of Section 250 2
− Do.

[4. Brief description of the drawings Figure 1: Infrared absorption spectrum of FiS11228 material, Figure 2: Ultraviolet absorption spectrum of Snee 4228 material, Figure 6: Nuclear magnetic resonance spectrum of Snee 4228 material. ] (Above) Attachment Claim 1 Novel antibiotic Snee 4228゜(
b) Elemental analysis value 0:62.1%, H near, 4%, N:
0% (b) molecule Mt 4800 d king
(c) Infrared absorption filter As shown in Figure 1.

(d) Ultraviolet absorber as shown in Figure 2.

(e) Nuclear magnetic resonance spectrum As shown in Figure 6. .

(to) ratio light river [α] 25-±a (c=t
o, methanol) ()) Solubility Methanol, ethanol, acetone + ml? Ethyl, benzene, ether.

Chloroform, dissolved in carbon tetrachloride, water.

Insoluble in n-hexane (1) Neutral (by ?4i pneumophoresis) (1 color reaction, 1 (easy) to ferric chloride, 2,4-dinitrophenylhydrazine (easy, 13 to ninhydrin) FA point 114-116° CQ Color: white needle-like crystals 2, an antibiotic that belongs to the genus Streptomyces and has the following properties: (a) Elemental analysis value: 0:62.1%, Hnia, 4% , N
: 0% (b) Molecular mass 480ω, solvent: chloroform) (c) Infrared IN UN yield spectrum shown in Figure 1].

b) Ultraviolet absorption spectrum as shown in Figure 2.

(e) Nuclear Magnetic Resonance Stroke This is the trace shown in Figure 5.

(to) specific rotation luminosity [α 5-” two (c=t
o, methanol) ()) # Solution Methanol, ethanol, acetone.

Soluble in ethyl acetate, benzene, ether, chloroform, carbon tetrachloride, insoluble in water, n-hexane (e) Neutral (by electrophoresis) (Color reaction agglomerated ferric, 2,4- Melting point: 114-116°C Color: White 1. Method for producing parent pile biological material Snee 4228.

5 Streptomyces, sp.
-6l98) The method according to claim 2d.

4. New antibiotic with the following properties% 5I-4228
(a) Elemental analysis value +3: 62.1%, H near, 4%,
N; 0% (b) Molecule Elbow 480α Elbow σ111
(1) Solvent: chloroform) (c) Infrared absorption filter As shown in Figure 1.

(d) Ultraviolet absorption spectrum As shown in Figure 2.

(e) Nuclear magnetic resonance system As shown in Figure 5.

(to) Specific rotation luminosity [α piece 6 = +4° (0 = 1
．． 0. Methanol () Solubility Methanol, ethanol, acetone.

Soluble in ethyl acetate, benzene, ether, chloroform, carbon tetrachloride, insoluble in water, n-hexane) Neutral (by electrophoresis) (S) Color reaction pressure, ferric chloride, 2, Lid K to 4-dinitrophenylhydrazine, negative to ninhydrin 2-(1)) Melting point: 114-116°C Color of substance: An agricultural fungicide containing white needle-like crystals as an active ingredient.

5. The industrial fungicide C according to item 4, which is a gray mold control agent.

6. The agricultural fungicide according to claim 4, which is a fungicide for controlling fungus.

The agricultural fungicide according to claim 4, which is a Z sheath blight control agent.

8. The agricultural fungicide according to claim 4, which is a blast control agent.

Procedural amendment (method) May 26, 1980 Haru Shimada, Commissioner of the Japan Patent Office, 1, Indication of the case Patent application 1982-214547 2 Title of the invention Novel antibiotic 5I-4228 substance, its manufacturing method and its effectiveness Agricultural fungicide as an ingredient 5 Relationship with the case of the person making the amendment Patent applicant Idemitsu Kosan Co., Ltd. 4, Agent 1-1-10-5 Kyobashi, Chuo-ku, Tokyo 104 Date of amendment order April 1980 April 27, 1982 (shipping date) 6 Column Z for the title of the invention in the specification to be amended Contents of the amendment Name of the invention in lines 5 to 4 of page 1 of the specification box [New Antibiotics 5I -4228, its production method and agricultural fungicide containing it as an active ingredient -1 New antibiotic Snee 4228
Substances, manufacturing methods thereof, and agricultural fungicides containing the same as active ingredients] H1 is corrected.

(hereinafter "-) = 1- Procedural amendment (voluntary) January 1981, I! Kazuo Wakasugi, Commissioner of the Patent Office on the 7th, 1, Patent Application No. 55-214547 1. Title of the invention: Novel antibiotic S-4228 substance, its manufacturing method, and agricultural fungicide containing it as an active ingredient. 5. Person making the amendment. Relationship to the case Patent application filed by Idemitsu Kosan Co., Ltd. 4, Osamu Fushi Publication 04 5, 1-1-10, Kyobashi, Chuo-ku, Tokyo Column 1 of the scope of the manufacturing license request in the specification subject to amendment Explanation column 2
Brief description of drawings and Drawing 1-2-6 Contents of amendment (1) The scope of claims (refer to the written amendment submitted on January 12, 1980) is corrected as shown in the attached sheet.

(2) [[α)”= in the second line from the bottom of page 12 of the specification
+4° (c = 1.0, methanol)” (see procedural amendment submitted on January 12, 1981) to “[α]
=+54 (0=0.1.methanol)".

(3) The text added next to Table 8 on page 25 ([
(See section I of the amendment in the procedural amendment submitted on January 12, 1657) [4. Brief explanation of the drawings Figure 1 is... 4. Brief explanation of the drawings Figure 1 is the infrared absorption spectrum of Snee 4228 material by KBr method, Figure 2 is the ultraviolet 1 absorption spectrum of Snee 4228 material in methanol, fIX3 is the Snee 4228 material. This is the nuclear magnetic resonance spectrum of substance 4228 in heavy chloroform.''

(4) Figure 2 is corrected as follows.

(hereinafter referred to as "2") Claim 1: A novel antibiotic Snee 4228. having the following properties.
, (a) Elemental analysis value C: 62.1%, H near, 4%,
N: 0% (b) Molecular weight 480 (by vapor pressure method, solvent: chloroform) (c) Infrared absorption spectrum
As shown in FIG.

2) Shiyu (line absorption spectrum) as shown in Figure 2.

0-) Nuclear magnetic resonance spectrum As shown in FIG.

()) Solubility Methanol, ethanol, acetone.

Ethyl acetate, benzene〉, ether, Loloform, soluble in carbon tetrachloride, water.

Insoluble in n-hexane) Neutral (by electrophoresis) Color reaction Positive for ferric chloride and 2,4-dinitrophenylhydrazine, negative for dihydrin) Melting point 114~ 116°C (color of paste substance white needle-like crystals 2, antibiotic W 5I-4228 that belongs to the genus Streptomyces and has the following properties (a) elemental analysis value 0: 62.1%, Hnia, 4%, N
: 0% (b) Molecular weight 480 (by vapor pressure method,
Molten tofu: Chloroform) Q → Infrared 1 slope yield spectrum
As shown in Figure 1).

←) Ultraviolet absorption spectrum as shown in Figure 26. (e) Nuclear magnetic resonance spectrum as shown in Figure 6.

(g) Solubility Methanol, ethanol, acetone.

Ethyl acetate, ben±〉, ether, Loloform, soluble in carbon tetrachloride, water.

Insoluble in n-hexane) Neutral (by electrophoresis) ('J) M color reaction Positive for ferric chloride, 2,4-dinitrophenylhydrazine, negative for ninhydrin R (negative) Melting point 114-116℃ Q Color of Substance A new antibiotic whose characteristic is to culture microorganisms capable of producing white gold monocrystals and collect the upper antibiotic from the culture material I. IJ construction method.

5. kA L to Streptomyces genus, antibiotics υ'7
A microorganism capable of producing f3 nee 4228 or Streptomyces sp.
P-6198). The method according to claim 2.

4 Novel antibiotic Snee 4228 (
b) Elemental analysis values C: 62.1%, H near, 4%, N:
0% (b) Molecular weight 480 (by vapor pressure method,
Solvent: Chloroform) (c) Infrared 1 acquisition spectrum
As shown in FIG.

b) Ultraviolet absorption spectrum as shown in Figure 2.

(e) Nuclear magnetic resonance spectrum As shown in Figure 3.

(g) Solubility Methanol, ethanol, acetone.

Ethyl acetate, benzene, ether, Loloform, soluble in carbon tetrachloride, water.

Insoluble in n-hexane (a) Neutral (according to electrophoresis) (Positive to ferric chloride, 2,4-dinitrophenylhydrazine, negative to ninhydrin) Melting point: 114-116°C color of matter
A fungicide for the potato industry that contains white needle-shaped crystals as an active ingredient.

5. The agricultural fungicide according to claim 4, which is a gray mold control agent.

6. The agricultural fungicide according to item 4, which is a charcoal-producing disease control agent.

7. A fungicide for agricultural use as described in item 4 of the scope of the herbicide, which is a sheath blight control agent.

a. The agricultural fungicide according to claim 4, which is a rice blast control agent.

Claims (1)

[Claims] 1. Novel antibiotic SI-4228 having the following properties
゜0) Elemental analysis value C: 62-1%, H near, 4
%, N: 0% (b) Molecular weight 48
0 ■ By removing atmosphere E, solvent: chloroform → (c) infrared m
Series spectrum As shown in Figure 1. b) Ultraviolet absorption spectrum as shown in Figure 2. (e) Nuclear magnetic resonance spectrum As shown in Figure 3. (to) Specific rotation [α 5 = +73
(C = 1.0, methanol → (g) solubility
methanol, ethanol, acetone. Soluble in ethyl acetate, benzene, ether, chloroform, carbon tetrachloride, water. Insoluble in n-hexane (E) Neutral (by electrophoresis) (S) Color reaction Positive for enriched ferric iron, 2,4-dinitrophenylhydrazine, negative for ninhydrin) Melting point 114-116°CQ Color of the substance White needle-like crystals 2 Antibiotics belonging to the genus Streptomyces and having the following properties (a) Elemental analysis values a: 62.1%, Hnia, 4%, 11: 0% (Ro) ) molecule fit
480 G Asada R Koyoru, Solvent: Chloroform (c) Infrared absorption spectrum As shown in FIG. b) Ultraviolet absorption spectrum as shown in Figure 2. (c) Nuclear magnetic resonance spectrum As shown in Fig. (to) Specific rotation W (afo' -17
5 (0=1.0. yt tano-4(g) solubility
methanol, ethanol, acetone. Soluble in ethyl acetate, benzene, ether, chloroform, carbon tetrachloride, water. Insoluble in n-hexane) Neutral (according to electrophoresis method) (Positive color reaction for ferric cyclization, 2,4-dinitrophenylhydrazine, negative for ninhydrin) Melting point 114-116°C) Substance A novel antibiotic S characterized by culturing a microorganism capable of producing white cylindrical crystals and collecting the above-mentioned antibiotic from the culture.
Method for manufacturing knee 4228. 5 Streptomyces, antibiotics Snee 4228
3. The method according to claim 2, wherein the microorganism is Streptomyces sp. S. 4228 (IRMP-6198). 4. Novel antibiotic Qjit substance Snee 42 with the following properties
28 (a) Elemental analysis value 0:62.1%, H near, 4%, N: 0% (b) Molecular fence
480ω\M'm, solvent: chlorophor → (c) Infrared absorption spectrum As shown in FIG. b) Ultraviolet absorption spectrum as shown in Figure 2. (e) Nuclear magnetic resonance spectrum As shown in Figure 5. (to) Specific optical rotation [α)'','-+73
(0=1.0.methanol-→()) Solubility Methanol, ethanol, acetone. Soluble in ethyl acetate, benzene, ether, chloroform, carbon tetracarbon, water. Insoluble in n-hexane (neutral (according to electrophoresis) (color reaction positive for ferric chloride, 2,4-dinitrophenylhydrazine, negative for ninhydrin); melting point 114-116°C) An agricultural fungicide containing white needle-shaped crystals as an active ingredient. -5. Agricultural fungicide according to item 4 of Hansho Seishu, which is a gray mold control agent. 6. The agricultural fungicide according to claim 4, which is a fungicide for controlling fungus. The agricultural fungicide according to claim 4, which is a Z sheath blight control agent. & The agricultural fungicide according to claim 4, which is a blast control agent.