JPH02275898A - Novel antibiotic substance kt-6291a and kt-6291b, microorganism capable of producing the same, its production and plant disease injury controlling agent - Google Patents
Novel antibiotic substance kt-6291a and kt-6291b, microorganism capable of producing the same, its production and plant disease injury controlling agentInfo
- Publication number
- JPH02275898A JPH02275898A JP24026989A JP24026989A JPH02275898A JP H02275898 A JPH02275898 A JP H02275898A JP 24026989 A JP24026989 A JP 24026989A JP 24026989 A JP24026989 A JP 24026989A JP H02275898 A JPH02275898 A JP H02275898A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- hydrolysis
- substance
- molecular weight
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 102220305863 rs1015663503 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 235000013547 stew Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Peptides Or Proteins (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Description
【発明の詳細な説明】
[発明の目的]
(産業上の利用分野)
本発明は、新規抗生物質KT−6291A及びKT−6
291B、それらを生産する微生物及び製法並びにそれ
らを有効成分とする植物病害防除剤に関するものである
。Detailed Description of the Invention [Object of the Invention] (Industrial Application Field) The present invention provides novel antibiotics KT-6291A and KT-6.
291B, microorganisms that produce them, production methods, and plant disease control agents containing them as active ingredients.
更に詳しくは、本発明の新規抗生物質KT−6291A
及びKT−6291Bは、バチルス・sp・KB−29
1菌株を培養して、その培養液から採取することにより
得られる。More specifically, the novel antibiotic KT-6291A of the present invention
and KT-6291B is Bacillus sp. KB-29
It can be obtained by culturing one strain of bacteria and collecting it from the culture solution.
(従来の技術及び発明が解決しようとする課題)従来、
バチルス属に属する微生物により生産される抗生物質と
して、多くのペプチド系抗生物質が知られているが、本
発明の抗生物質KT−6291A及びKT−6291B
は、その理化学的性質において、いずれの既知抗生物質
とも異なり、新規である。(Prior art and problems to be solved by the invention) Conventionally,
Many peptide antibiotics are known as antibiotics produced by microorganisms belonging to the genus Bacillus, and the antibiotics KT-6291A and KT-6291B of the present invention
is novel and different from any known antibiotic in its physicochemical properties.
[発明の構成]
(課題を解決するための手段及び作用)以下に、本発明
の新規抗生物質KT−629LA及びKT−6291B
並びにその製造法について詳述する。[Structure of the invention] (Means and effects for solving the problems) The novel antibiotics KT-629LA and KT-6291B of the present invention will be described below.
and its manufacturing method will be explained in detail.
本発明において使用されるバチルス属に属するKT−6
291A及びKT−6291Bを生産する菌としては、
本発明者らによって、茨城系の空中浮遊菌より新たに分
離されたバチルス・エスピー・KB−291(Baci
llussp、KB−291)株(以下rKB−291
株」という、)が挙げられる0本菌株の菌学的性状を示
すと、次の通りである。KT-6 belonging to the genus Bacillus used in the present invention
The bacteria that produce 291A and KT-6291B include:
Bacillus sp. KB-291 (Bacillus sp. KB-291) was newly isolated from an airborne bacterium of the Ibaraki family by the present inventors.
llussp, KB-291) strain (rKB-291
The mycological properties of the 0 bacterial strains listed below are as follows.
A、形態
(1)形及び大きさ:桿菌
0.5〜1.OX2.O〜3.0μ
(2)多形性ニ一連又は二連
(3)運動性:有り(周毛性ペン毛)
(4)胞子の有無:有り
胞子の形:楕円
胞子の形成部位:中心
(5)ダラム染色性:陽性
(6)抗酸性:無し
B、生育状態
(1)肉汁寒天平板培養
僅かに生育、不定形又は拡散状、不透明で乳白色
(2)肉汁寒天斜面培養
表面に僅かに生育、不透明で乳白色
(3)肉汁液体培養
僅かに生育、培養日数の経過とともに、僅かに混濁し菌
体は乳色を呈す。A. Morphology (1) Shape and size: Bacillus 0.5-1. OX2. O ~ 3.0 μ (2) Polymorphic double or double series (3) Motility: Yes (peritrichous pen hairs) (4) Presence or absence of spores: Yes Spore shape: Oval spore formation site: Center ( 5) Durham staining: Positive (6) Acid-fastness: None B, Growth status (1) Slight growth on gravy agar plate culture, amorphous or diffuse, opaque and milky white (2) Slight growth on gravy agar slant culture surface , Opaque and milky white (3) Meat juice liquid culture Slightly grows, and as the culture days pass, it becomes slightly cloudy and the bacterial cells take on a milky color.
(4)肉汁+1%グルコース培養
平板培養、斜面培養ともに生育良好0表面は隆起し内容
は不透明で乳白色を呈
す、液体培養は生育良好、培養日数の経過とともに、混
濁し菌体は乳白色を呈する。(4) Meat juice + 1% glucose culture Both plate culture and slant culture have good growth. The surface is raised and the contents are opaque and milky white. Growth is good in liquid culture. As the culture days pass, the bacteria become cloudy and the bacterial cells become milky white.
(5)バレイショ切片 生育良好、褐色のコロニー形成 (6)リドマスミルク ペプトン化し、乳糖はピンク色を呈する。(5) Potato section Good growth, brown colonies formed (6) Ridmus milk When peptonized, lactose takes on a pink color.
(7)肉汁ゼラチン穿刺
穿刺部位に生育する。特に表面に良く生育し層状に液化
する。(7) Grows at the puncture site of meat juice gelatin puncture. It grows particularly well on the surface and liquefies in layers.
C8生理学的性質
(1)硝酸塩の還元:有り
(2)脱窒反応:無し
く3)MRテスト:陰性
(4)VPテスト:陽性
(5)インドールの生成;無し
く6)硫化水素の生成:無し
く7)デンプンの加水分解:陽性
(8)クエン酸の加水分解:無し
く9)硝酸塩の利用:有り
(10)色素の生成
:ポテト・シュークロース・寒天培地において不溶性黄
色色素産生
(11)ウレアーゼ:無し
く12)ケトクロムオキシダーゼ:陰性(13)カゼイ
ンの分解:陽性
(14)ゼラチンの分解:陽性
(15)生育pH:pH5〜8、至適pH6〜7(16
)生育温度:18〜42℃、
至適温度:28〜32℃
(17)酸素に対する態度二通性嫌気性(18)塩化ナ
トリウム耐性=5%で生育せず(19)O−Fテスト
:グルコースより発酵的に酸を生成す
る。C8 Physiological properties (1) Nitrate reduction: Yes (2) Denitrification reaction: No 3) MR test: Negative (4) VP test: Positive (5) Indole formation; No 6) Hydrogen sulfide formation: None 7) Starch hydrolysis: Positive (8) Citric acid hydrolysis: None 9) Nitrate utilization: Yes (10) Pigment production: Insoluble yellow pigment production in potato, sucrose, agar medium (11) Urease: None 12) Ketochrome oxidase: Negative (13) Casein decomposition: Positive (14) Gelatin decomposition: Positive (15) Growth pH: pH 5-8, optimum pH 6-7 (16)
) Growth temperature: 18-42℃, Optimum temperature: 28-32℃ (17) Attitude towards oxygen Bifacult anaerobic (18) Sodium chloride tolerance = 5% does not grow (19) O-F test: Glucose Produces acid more fermentatively.
(20)カタラーゼ:陽性
(21)チロシンの分解:陰性
り、炭素源からの酸の生成の有無
L−アラビノース +
D−キシロース +
D−グルコース +
D−マンノース +
D−フラクトース +
D−ガラクトース +
マルトース +
スクロース +
ラクトース +
トレハロース +
D−ソルビット
D−マンニット +
イノジット
グリセリン +
デンプン +
基礎培地組成’ (N H4) * HP 041
g、塩化カリウム0.2g、硫酸マグネシウム0.2g
、酵母エキス0.2g、各種糖5g、寒天15g、ブロ
ムクレゾールパープルo、008g及び蒸留水1000
HI。(20) Catalase: Positive (21) Tyrosine decomposition: Negative, presence or absence of acid production from carbon source L-arabinose + D-xylose + D-glucose + D-mannose + D-fructose + D-galactose + maltose + Sucrose + Lactose + Trehalose + D-Sorvit D-Mannit + Inosit Glycerin + Starch + Basal medium composition' (NH4) * HP 041
g, potassium chloride 0.2g, magnesium sulfate 0.2g
, yeast extract 0.2g, various sugars 5g, agar 15g, bromcresol purple o, 008g and distilled water 1000g
H.I.
KB−291株の菌学的性質を、バーシーズ・マニュア
ル・オン・ディターミネーティブ・バクテリオロジー(
第8版)の記載に照合すると、菌学的性状、生理学的性
質及び炭素源からの酸の生成の特徴から、KB−291
株はバチルス属に属する一菌株と認められる0本菌株は
バチルス・エスピー−KB−291(Bacillus
sp、 KB −291)として工業技術院微生物
工業技術研究所に微工研菌寄第10395号として寄託
されている。The mycological properties of the KB-291 strain were determined using the Bersey's Manual on Determinative Bacteriology (
According to the description of KB-291 (8th edition), based on its mycological properties, physiological properties, and characteristics of acid production from carbon sources,
The strain is Bacillus sp. KB-291 (Bacillus sp. KB-291).
sp, KB-291) and has been deposited with the Institute of Microbial Technology, Agency of Industrial Science and Technology, as Fiber Science and Technology Research Institute No. 10395.
また、本発明の微生物としては、KB−291株は、自
然的及び人工的変異株は勿論、バチルス属に属する菌種
で、後述の抗生物質KT−・629IA及びKT−62
91Bの生産能を有する微生物は、すべて本発明の微生
物に含まれる。In addition, as the microorganism of the present invention, the KB-291 strain is a bacterial species belonging to the genus Bacillus, as well as natural and artificial mutant strains, and the antibiotic KT-629IA and KT-629, which will be described later,
All microorganisms capable of producing 91B are included in the microorganisms of the present invention.
本発明を実施するに当っては、バチルス属に属する抗生
物質KT−6291A及びKT−6291B生産菌を、
抗生物質を生産する通常の方法で培養することができる
。工業的に有利に生産するには該生産前を好気的条件下
で各種栄養物質を含む培地で通気撹拌培養を行えばよい
。In carrying out the present invention, antibiotic KT-6291A and KT-6291B-producing bacteria belonging to the genus Bacillus,
It can be cultured using conventional methods for producing antibiotics. For industrially advantageous production, aerobic agitation culture may be performed in a medium containing various nutrients under aerobic conditions before production.
培養条件及び培地の組成は、一般の抗生物質の製造に用
いられるものより選択すればよい、即ち、培地は炭素源
、窒素源、無機塩を含み、必要に応じてビタミン類、先
駆物質などを加えてもよい、炭素源としては、例えば、
グルコース、スクロース、澱粉、糖蜜、馬鈴薯などが、
単独で又は混合物として使用され、窒素源としては、例
えば、アンモニウム塩、硝酸塩、ペプトン、大豆粉、コ
ーン・スチーブ・リカー、麦芽抽出物など又はこれらの
混合物が用いられる。また、必要に応じて、シリコーン
油、大豆油、界面活性剤等の消泡剤を加えてもよい。The culture conditions and composition of the medium may be selected from those used in the production of general antibiotics. That is, the medium contains a carbon source, a nitrogen source, inorganic salts, and vitamins, precursors, etc. as necessary. Examples of carbon sources that may be added include:
Glucose, sucrose, starch, molasses, potatoes, etc.
Used alone or as a mixture, nitrogen sources include, for example, ammonium salts, nitrates, peptone, soybean flour, corn stew liquor, malt extract, etc., or mixtures thereof. Further, if necessary, an antifoaming agent such as silicone oil, soybean oil, or surfactant may be added.
培地は液体培地が好ましく、培地のpHは5.0〜8,
0がよく、培養温度は18〜42℃に調節するのがよい
、培養期間は通常2〜7日である。なお、これらの培養
条件は使用する生産菌の特性に応じてそれぞれ最適の条
件を選択すればよい。The medium is preferably a liquid medium, and the pH of the medium is 5.0 to 8.
The culture temperature is preferably adjusted to 18 to 42°C, and the culture period is usually 2 to 7 days. Note that the optimum culture conditions may be selected depending on the characteristics of the producing bacteria used.
培養終了後、培養液から抗生物質KT−6291A及び
KT−6291Bを分離・採取する方法は、通常の抗生
物質を培養物から分離・採取する方法に準じて行なえば
よい、即ち、各種有機溶媒による抽出法、各種活性吸着
剤によるクロマトグラフィーなどを適宜組み合せて、抗
生物質KT−6291A及び/またはKT−6291B
を採取する。After completion of the culture, the antibiotics KT-6291A and KT-6291B can be separated and collected from the culture solution in accordance with the usual method for separating and collecting antibiotics from the culture, i.e., by using various organic solvents. Antibiotics KT-6291A and/or KT-6291B can be obtained by appropriately combining extraction methods, chromatography using various active adsorbents, etc.
Collect.
(発明の実施例)
以下、実施例により本発明を更に詳細に説明するが、こ
の実施例は本発明の範囲を何ら制限するものではない。(Examples of the Invention) Hereinafter, the present invention will be explained in more detail with reference to Examples, but these Examples are not intended to limit the scope of the present invention in any way.
実施例
バチルス・エスピー・KB−291株を種培地、即ち、
可溶性澱粉2%、シュクロース1%、酵母エキス0.5
%及びペプトン0.5%を含有する培地(pH7,0)
に28℃で24時間培養し、得られた培養液を発酵培地
、即ち、可溶性澱粉2%、シュクロース1%及び酵母エ
キス0.5%を含有する培地(pH7,0)に接種し、
28℃で4日間培養した。Example Bacillus sp. KB-291 strain was used as a seed medium, i.e.
Soluble starch 2%, sucrose 1%, yeast extract 0.5
% and peptone 0.5% (pH 7,0)
Cultured at 28°C for 24 hours, the resulting culture solution was inoculated into a fermentation medium (pH 7.0) containing 2% soluble starch, 1% sucrose and 0.5% yeast extract,
The cells were cultured at 28°C for 4 days.
得られた培養液II2にn−ブタノールを加久撹拌抽出
し、n−プクノール抽出区分を得た。n−ブクノール抽
出区分を減圧濃縮乾固した後、メタノールに溶解し、セ
ファデックスLH−20のカラムに付し、100%メタ
ノールで溶出した。活性両分を減圧濃縮乾固し、粉末1
50mgを得た。N-butanol was extracted with stirring into the obtained culture solution II2 to obtain an n-pukunol extraction section. The n-buknol extracted fraction was concentrated to dryness under reduced pressure, then dissolved in methanol, applied to a Sephadex LH-20 column, and eluted with 100% methanol. Both active components were concentrated to dryness under reduced pressure to form powder 1.
50 mg was obtained.
得られた粉末をメタノールに溶解し、YMC−Pack
D−ODS−7(登録商標、山村化学研究所槽)を充填
した中圧カラムクロマトに付し、70%メタノールで溶
出することにより、抗生物質KT−62918,KT−
6291Aの順に溶出された。The obtained powder was dissolved in methanol and YMC-Pack
Antibiotics KT-62918, KT-
It was eluted in the order of 6291A.
かくして得られた抗生物質KT−6291Aは、以下に
述べるとおりの理化学的性質を有する新規な抗生物質で
ある。The antibiotic KT-6291A thus obtained is a novel antibiotic having the physicochemical properties described below.
(1)分子量:882 (FABマス・スペクトルによ
る)
(2)組成式:C41H14N10011(高分解能F
ABマス・スペクトルによる)
(3)融点:170℃から次第に褐変
(4)比旋光度: [α]乙’=+9.4’(C=0.
5、メタノール)
(5)物質の色:白色
(6)紫外線吸収スペクトル
二ん;:=”=210nm
第1図に示す。(1) Molecular weight: 882 (according to FAB mass spectrum) (2) Compositional formula: C41H14N10011 (high resolution F
(according to AB mass spectrum) (3) Melting point: Gradual browning from 170°C (4) Specific optical rotation: [α] Otsu' = +9.4' (C = 0.
5. Methanol) (5) Color of substance: white (6) Ultraviolet absorption spectrum: 210 nm Shown in FIG.
(7)赤外線吸収スペクトル
:シュ2Ham−’ 3300,2940゜2860
.1740,1660゜
1630.1550,1450゜
1380.1210.1140゜
840、 800. 720
第2図に示す。(7) Infrared absorption spectrum: 2Ham-' 3300, 2940°2860
.. 1740, 1660°1630.1550,1450°1380.1210.1140°840, 800. 720 shown in Figure 2.
(8)溶剤に対する溶解性
:メタノール、ブタノール、ジメチルスルホキシドに易
溶、酢酸エチル、クロ
ロホルム、ヘキサンに不溶
(9)呈色反応
:ドラーゲンドルフ反応、ライドンスミス反応に陽性、
坂口試薬に陽性、ニン
ヒドリン反応に陰性
(10)酸性、中性、塩基性の区別:塩基性(11)プ
ロトン核磁気共鳴スペクトル:第3図に示す。(8) Solubility in solvents: Easily soluble in methanol, butanol, dimethyl sulfoxide, insoluble in ethyl acetate, chloroform, hexane (9) Color reaction: Positive for Dragendorff reaction, Lydon-Smith reaction,
Positive for Sakaguchi's reagent, negative for ninhydrin reaction (10) Distinction between acidic, neutral, and basic: Basic (11) Proton nuclear magnetic resonance spectrum: Shown in Figure 3.
(12)C−13核磁気共鳴スペクトル:第4図に示す
。(12) C-13 nuclear magnetic resonance spectrum: Shown in FIG.
(13)Rf値 :シリカゲル薄層クロマトグラフィー (メルク社製HPTLCキーゼルゲ ル60) n−ブタノール:酢酸:水(65 10:25) Rf値 0.50 (14)酸加水分解 二6規定塩酸で16時間加水分解する と、アスパラギン酸、バリン、スレ オニン、アロスレオニン、アラニン を1:2:l:l:lのモル比で含 む物質である。(13) Rf value :Silica gel thin layer chromatography (HPTLC Kieselge manufactured by Merck & Co., Ltd. 60) n-butanol:acetic acid:water (65 10:25) Rf value 0.50 (14) Acid hydrolysis Hydrolyze with 26N hydrochloric acid for 16 hours and aspartic acid, valine, and thread. Onine, allothreonine, alanine in a molar ratio of 1:2:l:l:l. It is a substance that
同時に加水分解初期には末端にグア ニジル基をもつ分子量315のβ− ヒドロキシ脂肪酸を与え、加水分解 終了時には、脱水して末端にグアニ ジル基をもつ分子量297α、β− 不飽和脂肪酸を与える物質であ る。At the same time, in the early stage of hydrolysis, guar is present at the terminal. β- with a molecular weight of 315 and a nidyl group Gives hydroxy fatty acids and hydrolyzes them At the end, it dehydrates and leaves guani at the end. Molecular weight 297 α, β- with zyl group It is a substance that provides unsaturated fatty acids. Ru.
さらに上記の理化学的性状およびスペクトル解析の結果
から新規抗生物質KT−6291Aの化学構造を下記の
ように同定した。Furthermore, based on the results of the above-mentioned physicochemical properties and spectral analysis, the chemical structure of the new antibiotic KT-6291A was identified as follows.
かくして得られた抗生物質KT−6291Bは、以下に
述べるとおりの理化学的性質を有する新規な抗生物質で
ある。The antibiotic KT-6291B thus obtained is a novel antibiotic having the physicochemical properties described below.
(1)分子量: 946 (FABマス・スペクトルに
よる)
(2)組成式: C4sH,4N 100□(高分解能
FABマス・スペクトルによる)
(3)融点:160℃から次第に褐変
(4)比旋光度: [α]D25=+18.2゜(C=
0.5、メタノール)
(5)物質の色:白色
(6)紫外線吸収スペクトル
: LH::’= 212nm、 228nm、 27
8nm第5図に示す。(1) Molecular weight: 946 (according to FAB mass spectrum) (2) Compositional formula: C4sH,4N 100□ (according to high-resolution FAB mass spectrum) (3) Melting point: Gradual browning from 160°C (4) Specific optical rotation: [α]D25=+18.2°(C=
0.5, methanol) (5) Color of substance: white (6) Ultraviolet absorption spectrum: LH::'= 212 nm, 228 nm, 27
8 nm as shown in FIG.
(7)赤外線吸収スペクトル
:シ二’i: cm−’ 3300.2900゜28
60.1740,1660゜
1520.1200.1140
800、 720
第6図に示す。(7) Infrared absorption spectrum: cm-' 3300.2900°28
60.1740,1660°1520.1200.1140 800, 720 Shown in Figure 6.
(8)溶剤に対する溶解性
:メタノール、ブタノール、ジメチルスルホキシドに易
溶、クロロホルム、ヘ
キサンに不溶
(9)呈色反応
:ドラーゲンドルフ反応、ライドンスミス反応に陽性、
バウリ試薬及び板目試
薬に陽性、ニンヒドリン反応に陰性
(10)酸性、中性、塩基性の区別:塩基性(11)プ
ロトン核磁気共鳴スペクトル:第7図に示す。(8) Solubility in solvents: Easily soluble in methanol, butanol, dimethyl sulfoxide, insoluble in chloroform and hexane (9) Color reaction: Positive for Dragendorff reaction, Lydon-Smith reaction,
Positive for Bauli reagent and Itame reagent, negative for ninhydrin reaction (10) Distinction between acidic, neutral, and basic: Basic (11) Proton nuclear magnetic resonance spectrum: Shown in FIG.
(12)C−13核磁気共鳴スペクトル;第8図に示す
。(12) C-13 nuclear magnetic resonance spectrum; shown in FIG.
(13)Rf値 :シリカゲル薄層クロマトグラフィー (メルク社製HPTLCキーゼルゲ ル60) n−ブタノール:酢酸:水(65 10:25) Rf値 0.57 (14)酸加水分解 =6規定塩酸で16時間加水分解する と、アスパラギン酸、バリン、スレ オニン、アロスレオニン、アラニ ン、チロシンをl:1:1:l:1 のモル比で含む物質である。(13) Rf value :Silica gel thin layer chromatography (HPTLC Kieselge manufactured by Merck & Co., Ltd. 60) n-butanol:acetic acid:water (65 10:25) Rf value 0.57 (14) Acid hydrolysis = Hydrolyzed with 6N hydrochloric acid for 16 hours and aspartic acid, valine, and thread. Onin, Allothreonine, Arani and tyrosine l:1:1:l:1 It is a substance containing in a molar ratio of .
同時に加水分解初期には末端にグア ニジル基をもつ分子量315のβ− ヒドロキシ脂肪酸を与え、加水分解 終了時には脱水して末端にグアニジ ル基をもつ分子量297のα、β− 不飽和脂肪酸を与える物質である。At the same time, in the early stage of hydrolysis, guar is present at the terminal. β- with a molecular weight of 315 and a nidyl group Gives hydroxy fatty acids and hydrolyzes them At the end, it is dehydrated and guanidine is added to the end. α,β- with a molecular weight of 297 It is a substance that provides unsaturated fatty acids.
さらに上記の理化学的性状およびスペクトル解析の結果
から新規抗生物質KT−6291Bの化学構造を下記の
ように同定した。Furthermore, based on the results of the above-mentioned physicochemical properties and spectral analysis, the chemical structure of the new antibiotic KT-6291B was identified as follows.
次に、抗生物質KT−6291A及びKT−6291B
の生物学的活性について説明する。抗生物質KT−62
91A及びKT−6291Bは、一部の酵母菌、ダラム
陽性菌及び糸状菌に対し強い生育阻止作用を示す、最小
発育阻止濃度(MIC)の測定は、抗生物質KT−62
91AまたはKT−6291Bを含有する寒天平板稀釈
法によった。Next, antibiotics KT-6291A and KT-6291B
Describe the biological activity of Antibiotic KT-62
91A and KT-6291B show a strong growth inhibitory effect on some yeast bacteria, Durum-positive bacteria, and filamentous fungi.The measurement of the minimum inhibitory concentration (MIC) was performed using the antibiotic KT-6291B.
Agar plate dilution method containing 91A or KT-6291B was used.
以下に結果を示す。The results are shown below.
匠夏1辺1月 最小発育阻止濃度(77m1)に
T−6291A
KT−6291B
lagenariuml
aeruginosa IFO−3923)IFO−3
5131
抗°生物質KT−6291A及びKT−6291Bは、
各種植物病原菌、特に糸状菌に対して、優れた抗菌作用
を示すことにより、農業用殺菌剤として使用することが
できる。Takumi Summer 1st January Minimum Inhibitory Concentration (77ml) T-6291A KT-6291B lagenarium aeruginosa IFO-3923) IFO-3
5131 Antibiotics KT-6291A and KT-6291B are
It can be used as an agricultural fungicide because it exhibits excellent antibacterial activity against various plant pathogenic bacteria, especially filamentous fungi.
KT−6291A及びKT−6291Bを農業用殺菌剤
として使用する場合は、通常当該技術分野において知ら
れている農薬製剤と同様に適当な固体担体、乳化分散剤
等を用いて粒剤、粉剤、乳剤、水和剤、錠剤、油剤、噴
霧剤、煙霧剤等の任意の剤型番ご製剤化することができ
る。固体担体としては、クレー、カオリン、ベントナイ
ト、酸性白土、珪藻土、炭酸カルシウム、ニトロセルロ
ース、デンプン、アラビアゴム等が使用できる。また、
液体担体として、水、メタノール、エタノール、ジメチ
ルホルムアミド、エチレングリコール等が使用できる。When KT-6291A and KT-6291B are used as agricultural fungicides, they can be prepared into granules, powders, or emulsions using appropriate solid carriers, emulsifying dispersants, etc. in the same way as agricultural chemical formulations known in the art. It can be formulated into any formulation such as wettable powders, tablets, oils, sprays, atomizers, etc. As the solid carrier, clay, kaolin, bentonite, acid clay, diatomaceous earth, calcium carbonate, nitrocellulose, starch, gum arabic, etc. can be used. Also,
Water, methanol, ethanol, dimethylformamide, ethylene glycol, etc. can be used as liquid carriers.
また、製剤上、一般に使用される補助剤、例えば、高級
アルコールの硫酸エステル、ポリオキシエチレンアルキ
ルアリールエーテル及びそのスルホン酸塩、アルキルア
リールソルビクンモノラウレート、アルキルアリールス
ルホン酸塩、アルキルアリールポリエチレングリコール
エーテル、ジナフチルメタンジスルホン酸ナトリウムの
ホルマリン縮合物、アルキルジメチルベンジルアンモニ
ウムクロリド等を適宜配合することができる。In addition, adjuvants commonly used in formulations, such as sulfuric esters of higher alcohols, polyoxyethylene alkylaryl ethers and their sulfonates, alkylaryl sorbicune monolaurate, alkylaryl sulfonates, alkylaryl polyethylene glycols, etc. Ether, formalin condensate of sodium dinaphthylmethane disulfonate, alkyldimethylbenzyl ammonium chloride, etc. can be appropriately blended.
また、本発明の薬剤は、他の殺菌剤、除草剤、殺虫剤、
肥料、土壌改良剤と適宜混合して使用することができる
。In addition, the drug of the present invention may be used with other fungicides, herbicides, insecticides,
It can be used by appropriately mixing it with fertilizers and soil conditioners.
以下に本発明を製造例によって具体的に説明するが、本
発明はこれに限定されるものではない。The present invention will be specifically explained below using manufacturing examples, but the present invention is not limited thereto.
なお、製剤例中「部」は重量部を表わす。In addition, "parts" in the formulation examples represent parts by weight.
製剤例1(水和剤)
抗生物質KT−6291AまたはKT−6291B10
部、ポリオキシエチレンアルキルアリールエーテルスル
ホン酸塩10部、ジナフチルメタンジスルホン酸ナトリ
ウムのホルマリン縮合物2部、クレー78部を混合粉砕
して水和剤100部を得た。Formulation example 1 (hydrating powder) Antibiotic KT-6291A or KT-6291B10
10 parts of a polyoxyethylene alkylaryl ether sulfonate, 2 parts of a formalin condensate of sodium dinaphthylmethane disulfonate, and 78 parts of clay were mixed and ground to obtain 100 parts of a wettable powder.
製剤例2(液剤)
抗生物質KT−6291AまたはKT−6291BlO
部、ジメチルホルムアミド20部、エチレングリコール
10部、アルキルジメチルベンジルアンモニウムクロリ
ド10部、メタノール50部を混合溶解して液剤100
部を得た。Formulation example 2 (liquid) Antibiotic KT-6291A or KT-6291BIO
20 parts of dimethylformamide, 10 parts of ethylene glycol, 10 parts of alkyldimethylbenzyl ammonium chloride, and 50 parts of methanol were mixed and dissolved to make a solution of 100 parts.
I got the department.
製剤例3(水和剤)
前記に示す本実施例の培養液lI2にn−ブタノールを
加え撹拌抽出し、得られたn−ブタノール区分をセファ
デックスLH−20のカラムに付し、その活性画分を減
圧濃縮乾固し、KT−6291AとKT−6291Bと
の混合物[KT−6291A/KT−6291B (重
量比=10:1)]を1150mgた。Formulation example 3 (hydrating powder) N-butanol was added to the culture solution lI2 of this example shown above and extracted with stirring, and the obtained n-butanol fraction was applied to a column of Sephadex LH-20, and the active fraction was The mixture was concentrated to dryness under reduced pressure to obtain 1150 mg of a mixture of KT-6291A and KT-6291B [KT-6291A/KT-6291B (weight ratio = 10:1)].
この混合物10部、ポリオキシエチレンアルキルアリー
ルエーテルスルホン酸塩10部、ジナフチルメタンジス
ルホン酸ナトリウムのホルマリン縮合物2部、クレー7
8部を混合粉砕して水和剤100部を得た。10 parts of this mixture, 10 parts of polyoxyethylene alkylaryl ether sulfonate, 2 parts of formalin condensate of sodium dinaphthylmethane disulfonate, 7 parts of clay
8 parts were mixed and ground to obtain 100 parts of a wettable powder.
次に、試験例により本発明殺菌剤による各種植物病防除
効果を具体的に説明する。Next, the effect of controlling various plant diseases by the fungicide of the present invention will be specifically explained using test examples.
試験例1
(キュウリ灰色かび病に対する防除試験)キュウリ(品
種:ときわ光3号P型)の発芽後、10日間生育した幼
苗を茎部より切り取り、子葉面にキュウリ灰色かび病菌
(Botrytiscinerea )の胞子懸濁液を
304置いた。胞子懸濁液の上に抗生物質検定用ペーパ
ーディスク〔直径8mm)をのせ、製剤例1に準じて調
製した水和剤9ON!を滴下した0次いで、子葉を20
℃、相対湿度90%の条件下に放置し、3日後に子葉裏
面の病斑進展の程度を調べた。Test Example 1 (Control test against gray mold of cucumber) After germination of cucumber (variety: Tokiwa Hikari No. 3 P type), young seedlings grown for 10 days were cut from the stem, and spores of the gray mold of cucumber (Botrytiscinerea) were added to the cotyledon surface. The suspension was placed at 304 ml. A paper disk for antibiotic assay (diameter 8 mm) was placed on top of the spore suspension, and the hydrating powder 9ON! prepared according to Formulation Example 1 was added. 0 and then 20 cotyledons.
The plants were left under conditions of 90% relative humidity and 90% relative humidity, and the degree of lesion development on the underside of the cotyledons was examined after 3 days.
なお、病斑進展阻止は次の方法により算出した。In addition, the inhibition of lesion progression was calculated by the following method.
病斑進展阻止率(%)= × 100 (り製剤の代りに水を置いたもの この結果を以下に示す。Lesion progression inhibition rate (%) = × 100 (Water is placed in place of the preparation) The results are shown below.
KT−6291A 100 100
なし50 1(1(l なし25
75 なし
KT−62918100100なし
50 100 なし
2530 なし
ベンレート 250 −100 なし試
験例2
(キュウリ炭痘病に対する防除試験)
直径6cmの合成樹脂製ポットに1ポット当り1粒のキ
ュウリ(品種:ときわ光3号P型)種子を植え温室内で
生育させる。1〜2葉期に生育したポットに製剤例1に
準じて調製した水和剤を1株当り1011d!スプレー
ガンを用いて散布した。風乾後、キエウリ炭痘病菌(C
olletotrichumlagenarium)胞
子懸濁液(l−当り胞子濃度が1.2xlO’個)を噴
霧接種し、相対湿度90%、温度25℃、暗黒下に2日
放置した後、温室内に移し、5日後、葉上の病斑を調査
し次式により防除価を求めた。KT-6291A 100 100
None 50 1 (1 (l None 25
75 None KT-62918100100 None 50 100 None 2530 None Benlate 250 -100 None Test Example 2 (Cucumber anthracnose control test) One cucumber per pot in a synthetic resin pot with a diameter of 6 cm (variety: Tokiwa Hikari No. 3) P type) seeds are planted and grown in a greenhouse. A hydrating powder prepared according to Formulation Example 1 was added to a pot grown at the 1-2 leaf stage at a dose of 1011 d per plant! Sprayed using a spray gun. After air-drying, anthrax Bacillus chieuri (C
olletotrichumlagenarium) spore suspension (1.2xlO' spores per liter) was spray-inoculated and left in the dark at a relative humidity of 90% and a temperature of 25°C for 2 days, then transferred to a greenhouse, and after 5 days, The lesions on the leaves were investigated and the control value was calculated using the following formula.
防除価(%)= この結果を以下に示す。Control value (%) = The results are shown below.
にT−6291A 100 92
なし5080 なし
KT−6291B 100 96
なし5075 なし
ダコニフル Ioo(191ナシ
試験例3
(イネいもち病に対する防除試験)
水稲籾(品種:こしひかり)を直径6cmの合成樹脂製
ポットに直播しく10株/ポット)、4葉期において製
剤例1に準じて調製した水和剤を所定濃度に希釈したも
のを1ポツト当たり50mfをスプレーガンで補体に散
布した。風乾後、イネいもち病菌(Pyricular
ia oryzae)の胞子懸濁液(顕微鏡100倍視
野当たり胞子30個)を噴霧接種し、相対湿度90%、
温度25℃、暗黒下に1日放置した後、温室内に移し、
5日後、葉上の病斑を調査し、試験例2で示した式によ
り防除価を求めた。T-6291A 100 92
None 5080 None KT-6291B 100 96
None 5075 None Daconiflu Ioo (191 Pear Test Example 3 (Control test against rice blast) Rice paddy (variety: Koshihikari) was sown directly into synthetic resin pots with a diameter of 6 cm, 10 plants/pot), and Formulation Example 1 was applied at the 4-leaf stage. A hydrating powder prepared according to the method was diluted to a predetermined concentration and sprayed onto the complement at 50 mf per pot using a spray gun. After air-drying, rice blast fungus (Pyricular
Ia oryzae) spore suspension (30 spores per 100x microscope field) was spray-inoculated, and the relative humidity was 90%.
After leaving it in the dark at a temperature of 25℃ for one day, it was transferred to a greenhouse.
After 5 days, lesions on the leaves were investigated, and the control value was determined using the formula shown in Test Example 2.
この結果を以下に示す。The results are shown below.
KT−6291A 100 95
なし5070 なし
ラブサイド 500 98 なし
上記の結果より、本発明の抗生物質KT−6291Aを
有効成分として含有する薬剤は、各種植物病害に対して
、極めて高い防除価を示し、かつ薬害が認められないな
ど、農業用殺菌剤として有効であることが明らかにされ
た。KT-6291A 100 95
None 5070 None Loveside 500 98 None From the above results, the drug containing the antibiotic KT-6291A of the present invention as an active ingredient shows an extremely high control value against various plant diseases, and no phytotoxicity is observed. It has been shown that it is effective as an agricultural fungicide.
試験例4
製剤例1に準じて調製した水和剤に代えて、製剤例3に
準じて調製した水和剤を用いたほかは、試験例1と同様
にして病斑進展阻止率を求めた。Test Example 4 The lesion progression inhibition rate was determined in the same manner as Test Example 1, except that a hydrating powder prepared according to Formulation Example 3 was used instead of the hydrating powder prepared according to Formulation Example 1. .
この結果を以下に示す。The results are shown below.
KT−6291A、B 100. 10
0 なしく混合物) 50 1
00 なし2575 なし
ベンレート 250 100 な
し上記の結果より、本発明の抗生物質KT−6291A
及び/またはKT−6291Bを有効成分として含有す
る薬剤は、各種植物病害に対して、極めて高い防除価を
示し、かつ薬害が認められないなど、農業用殺菌剤とし
て有効であることが明らかにされた。KT-6291A, B 100. 10
0 mixture) 50 1
00 None 2575 None Benlate 250 100 None From the above results, the antibiotic KT-6291A of the present invention
It has been clarified that drugs containing KT-6291B as an active ingredient are effective as agricultural fungicides, showing extremely high control value against various plant diseases and causing no phytotoxicity. Ta.
[発明の効果]
本発明によれば、各種植物病原糸状菌に対して優れた作
用を示す新規抗生物質KT−6291A及びKT−62
91Bを提供することができる。[Effects of the Invention] According to the present invention, novel antibiotics KT-6291A and KT-62 exhibit excellent effects against various plant pathogenic filamentous fungi.
91B can be provided.
第1図、第2図、第3図及び第4図は、それぞれ抗生物
質KT−6291Aの紫外線吸収スペクトル、赤外線吸
収スペクトル、プロトン核磁気共鳴スペクトル及びC−
13核磁気共鳴スペクトルを示し、第5図、第6図、第
7図及び第8図は、それぞれ抗生物質KT−6291B
の紫外線吸収スペクトル、赤外線吸収スペクトル、プロ
トン核磁気共鳴スペクトル及びC−13核磁気共鳴スペ
クトルを示す。
手続補正書(方式]
平成
1月24日Figures 1, 2, 3 and 4 respectively show the ultraviolet absorption spectrum, infrared absorption spectrum, proton nuclear magnetic resonance spectrum and C-
13 nuclear magnetic resonance spectra, and FIGS. 5, 6, 7, and 8 respectively show the antibiotic KT-6291B.
The ultraviolet absorption spectrum, the infrared absorption spectrum, the proton nuclear magnetic resonance spectrum, and the C-13 nuclear magnetic resonance spectrum are shown. Procedural amendment (formality) January 24, 1999
Claims (1)
91A ▲数式、化学式、表等があります▼( I ) 2、下記の理化学的性質を有する新規抗生物質KT−6
291A物質 (1)分子量:882 (2)組成式:C_4_1H_7_4N_1_0O_1
_1(3)融点:170℃から次第に褐変 (4)比旋光度:[α]D^2^5=+9.4°(C=
0.5、メタノール) (5)物質の色:白色 (6)紫外線吸収スペクトル :λ^M^e^O^H_m_a_x=210nm(7)
赤外線吸収スペクトル :ν^K^B^r_m_a_xcm^−^13300、
2940、2860、1740、1660、 1630、1550、1450、 1380、1210、1140、 840、800、720 (8)溶剤に対する溶解性 :メタノール、ブタノール、ジメチルス ルホキシドに易溶、酢酸エチル、クロ ロホルム、ヘキサンに不溶 (9)呈色反応 :ドラーゲンドルフ反応、ライドンスミ ス反応及び坂口試薬に陽性、ニンヒド リン反応に陰性 (10)酸性、中性、塩基性の区別:塩基性(11)R
f値 :シリカゲル薄層クロマトグラフィー (メルク社製HPTLCキーゼルゲ ル60) n−ブタノール:酢酸:水(65: 10:25) Rf値0.50 (12)酸加水分解 :6規定塩酸で16時間加水分解する と、アスパラギン酸、バリン、スレ オニン、アロスレオニン、アラニン を1:2:1:1:1のモル比で含む 物質である。 同時に加水分解初期には末端にグア ニジル基をもつ分子量315のβ− ヒドロキシ脂肪酸を与え、加水分解 終了時には脱水して末端にグアニジ ル基をもつ分子量297のα,β不 飽和脂肪酸を与える物質である。 3、構造式(II)で示される新規抗生物質KT−629
1B ▲数式、化学式、表等があります▼(II) 4、下記の理化学的性質を有する新規抗生物質KT−6
291B物質 (1)分子量:946 (2)組成式:C_4_5H_7_4N_1_0O_1
_2(3)融点:160℃から次第に褐変 (4)比旋光度:[α]D^2^5=+18.2°(C
=0.5、メタノール) (5)物質の色:白色 (6)紫外線吸収スペクトル :λ^M^e^O^H_m_a_x=212nm、22
8nm、278nm(7)赤外線吸収スペクトル :ν^K^B^r_m_a_xcm^−^13300、
2900、2860、1740、1660、 1520、1200、1140、 800、720 (8)溶剤に対する溶解性 :メタノール、ブタノール、ジメチルス ルホキシドに易溶、クロロホルム、ヘ キサンに不溶 (9)呈色反応 :ドラーゲンドルフ反応、ライドンスミ ス反応に陽性、バウリ試薬及び坂口試 薬に陽性、ニンヒドリン反応に陰性 (10)酸性、中性、塩基性の区別:塩基性(11)R
f値 :シリカゲル薄層クロマトグラフィー (メルク社製HPTLCキーゼルゲ ル60) n−ブタノール:酢酸:水(65: 10:25) Rf値0.57 (12)酸加水分解 :6規定塩酸で16時間加水分解する と、アスパラギン酸、バリン、スレ オニン、アロスレオニン、アラニ ン、チロシンを1:1:1:1:1 のモル比で含む物質である。 同時に加水分解初期には末端にグア ニジル基をもつ分子量315のβ− ヒドロキシ脂肪酸を与え、加水分解 終了時には、脱水して末端にグアニ ジル基をもつ分子量297のα,β −不飽和脂肪酸を与える物質であ る。 5、バチルス属に属する抗生物質KT− 6291A及びKT−6291B生産性を有するバチル
ス・sp・KB−291菌株。 6、バチルス属に属するKT−6291A及びKT−6
291B物質生産菌を培養し、その培養物からKT−6
291A及び/またはKT−6291B物質を採取する
ことを特徴とするKT−6291A及び/またはKT−
6291Bの製造法。 7、抗生物質KT−6291A及び/またはKT−62
91Bを有効成分として含有する植物病害防除剤。[Claims] 1. Novel antibiotic KT-62 represented by structural formula (I)
91A ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (I) 2. KT-6, a new antibiotic with the following physical and chemical properties
291A substance (1) Molecular weight: 882 (2) Compositional formula: C_4_1H_7_4N_1_0O_1
_1 (3) Melting point: Gradually browns from 170℃ (4) Specific optical rotation: [α]D^2^5=+9.4° (C=
0.5, methanol) (5) Color of substance: white (6) Ultraviolet absorption spectrum: λ^M^e^O^H_m_a_x=210nm (7)
Infrared absorption spectrum: ν^K^B^r_m_a_xcm^-^13300,
(8) Solubility in solvents: Easily soluble in methanol, butanol, dimethyl sulfoxide, ethyl acetate, chloroform, hexane Insoluble (9) Color reaction: Positive for Dragendorff reaction, Lydon-Smith reaction and Sakaguchi reagent, negative for ninhydrin reaction (10) Distinction between acidic, neutral and basic: Basic (11) R
f value: Silica gel thin layer chromatography (HPTLC Kieselgel 60 manufactured by Merck & Co.) n-butanol:acetic acid:water (65: 10:25) Rf value 0.50 (12) Acid hydrolysis: Hydrolysis with 6N hydrochloric acid for 16 hours Then, it is a substance containing aspartic acid, valine, threonine, allothreonine, and alanine in a molar ratio of 1:2:1:1:1. At the same time, it is a substance that gives a β-hydroxy fatty acid with a molecular weight of 315 with a guanidyl group at the end at the initial stage of hydrolysis, and dehydrates to give an α, β unsaturated fatty acid with a molecular weight of 297 and a guanidyl group on the end after hydrolysis. 3. Novel antibiotic KT-629 represented by structural formula (II)
1B ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (II) 4. KT-6, a new antibiotic with the following physical and chemical properties
291B substance (1) Molecular weight: 946 (2) Compositional formula: C_4_5H_7_4N_1_0O_1
_2 (3) Melting point: Gradually browning from 160℃ (4) Specific optical rotation: [α]D^2^5 = +18.2° (C
=0.5, methanol) (5) Color of substance: white (6) Ultraviolet absorption spectrum: λ^M^e^O^H_m_a_x=212 nm, 22
8nm, 278nm (7) Infrared absorption spectrum: ν^K^B^r_m_a_xcm^-^13300,
2900, 2860, 1740, 1660, 1520, 1200, 1140, 800, 720 (8) Solubility in solvents: Easily soluble in methanol, butanol, dimethyl sulfoxide, insoluble in chloroform and hexane (9) Color reaction: Dragendorff Reaction, positive for Lydon-Smith reaction, positive for Bauli reagent and Sakaguchi reagent, negative for ninhydrin reaction (10) Distinction between acidic, neutral, and basic: basic (11) R
f value: Silica gel thin layer chromatography (HPTLC Kieselgel 60 manufactured by Merck) n-butanol:acetic acid:water (65: 10:25) Rf value 0.57 (12) Acid hydrolysis: Hydrolysis with 6N hydrochloric acid for 16 hours Then, it is a substance containing aspartic acid, valine, threonine, allothreonine, alanine, and tyrosine in a molar ratio of 1:1:1:1:1. At the same time, in the early stage of hydrolysis, it gives a β-hydroxy fatty acid with a molecular weight of 315, which has a guanidyl group at the end, and at the end of hydrolysis, it dehydrates to give an α,β-unsaturated fatty acid with a molecular weight of 297, which has a guanidyl group at the end. be. 5. Bacillus sp. KB-291 strain having productivity of antibiotics KT-6291A and KT-6291B belonging to the genus Bacillus. 6. KT-6291A and KT-6 belonging to the genus Bacillus
291B substance-producing bacteria were cultured, and KT-6 was obtained from the culture.
KT-6291A and/or KT-291A and/or KT-291A and/or KT-6291B substances are collected.
6291B manufacturing method. 7. Antibiotic KT-6291A and/or KT-62
A plant disease control agent containing 91B as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24026989A JPH02275898A (en) | 1989-01-10 | 1989-09-18 | Novel antibiotic substance kt-6291a and kt-6291b, microorganism capable of producing the same, its production and plant disease injury controlling agent |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1-2102 | 1989-01-10 | ||
JP210289 | 1989-01-10 | ||
JP24026989A JPH02275898A (en) | 1989-01-10 | 1989-09-18 | Novel antibiotic substance kt-6291a and kt-6291b, microorganism capable of producing the same, its production and plant disease injury controlling agent |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02275898A true JPH02275898A (en) | 1990-11-09 |
Family
ID=26335425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP24026989A Pending JPH02275898A (en) | 1989-01-10 | 1989-09-18 | Novel antibiotic substance kt-6291a and kt-6291b, microorganism capable of producing the same, its production and plant disease injury controlling agent |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02275898A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0591869A (en) * | 1991-10-02 | 1993-04-16 | Yuukishitsu Hiryo Seibutsu Kassei Riyou Gijutsu Kenkyu Kumiai | Plant pathogenic fungus-inhibiting microorganism and its utilization |
US5869038A (en) * | 1992-03-26 | 1999-02-09 | The Minister Of Agriculture, Fisheries And Food In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Biological control of fungal post harvest diseases with bacteria |
WO2005019245A1 (en) * | 2003-08-25 | 2005-03-03 | Keio University | Heptadepsin |
WO2005029962A1 (en) * | 2003-10-02 | 2005-04-07 | Chimac-Agriphar S.A. | Composition and method for treating banana trees |
WO2006016558A1 (en) * | 2004-08-09 | 2006-02-16 | Kaken Pharmaceutical Co., Ltd. | Novel strains belonging to the genus paenibacillus and method of controlling plant disease by using these strains or culture thereof |
CN108913622A (en) * | 2018-07-06 | 2018-11-30 | 四川农业大学 | The preparation and application of a kind of bacillus megaterium BM22 and its gemma pulvis |
-
1989
- 1989-09-18 JP JP24026989A patent/JPH02275898A/en active Pending
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0591869A (en) * | 1991-10-02 | 1993-04-16 | Yuukishitsu Hiryo Seibutsu Kassei Riyou Gijutsu Kenkyu Kumiai | Plant pathogenic fungus-inhibiting microorganism and its utilization |
US5869038A (en) * | 1992-03-26 | 1999-02-09 | The Minister Of Agriculture, Fisheries And Food In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Biological control of fungal post harvest diseases with bacteria |
WO2005019245A1 (en) * | 2003-08-25 | 2005-03-03 | Keio University | Heptadepsin |
WO2005029962A1 (en) * | 2003-10-02 | 2005-04-07 | Chimac-Agriphar S.A. | Composition and method for treating banana trees |
WO2006016558A1 (en) * | 2004-08-09 | 2006-02-16 | Kaken Pharmaceutical Co., Ltd. | Novel strains belonging to the genus paenibacillus and method of controlling plant disease by using these strains or culture thereof |
US7935335B2 (en) | 2004-08-09 | 2011-05-03 | Kaken Pharmaceutical Co., Ltd. | Strains belonging to the genus Paenibacillus and method of controlling plant disease by using these strains or culture thereof |
CN108913622A (en) * | 2018-07-06 | 2018-11-30 | 四川农业大学 | The preparation and application of a kind of bacillus megaterium BM22 and its gemma pulvis |
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