JPH01197488A - Physiologically active substance ksb-1939 compound and production thereof - Google Patents
Physiologically active substance ksb-1939 compound and production thereofInfo
- Publication number
- JPH01197488A JPH01197488A JP2254388A JP2254388A JPH01197488A JP H01197488 A JPH01197488 A JP H01197488A JP 2254388 A JP2254388 A JP 2254388A JP 2254388 A JP2254388 A JP 2254388A JP H01197488 A JPH01197488 A JP H01197488A
- Authority
- JP
- Japan
- Prior art keywords
- ksb
- compound
- substance
- active substance
- physiologically active
- 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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- 239000003463 adsorbent Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 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
- 150000002596 lactones Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- BBLGCDSLCDDALX-LKGBESRRSA-N piericidin A Chemical compound COC=1NC(C\C=C(/C)C\C=C\C(\C)=C\[C@@H](C)[C@@H](O)C(\C)=C\C)=C(C)C(=O)C=1OC BBLGCDSLCDDALX-LKGBESRRSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013587 production medium Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は殺虫、殺ダニ、駆虫作用を示す新規生理活性物
質ＫＳＢ−１９３９Ｓ、及びその製造法に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel physiologically active substance KSB-1939S exhibiting insecticidal, acaricidal and anthelmintic effects, and a method for producing the same.
（従来の技術）
農業用薬剤は、高い収穫を安定的に確保する上で必要不
可欠なものであることは言及の余地のないことであるが
、作物及び土壌への残留を通して人体に体する毒性や環
境汚染の問題等を引き起こす可能性も否定出来ず、更に
安全性の高い農業用薬剤の開発が望まれている１本発明
者らは、より安全なＱ業を開発すべく、微生物生産物に
着目して研究を行なった。(Prior art) It goes without saying that agricultural chemicals are indispensable for stably securing high yields, but they are toxic to humans through their residue in crops and soil. The possibility of causing environmental pollution problems cannot be denied, and the development of even safer agricultural chemicals is desired.1 In order to develop safer Q-products, the inventors of the present invention The research focused on.
これまでに微生物を起源とする殺虫性物質には、糸状菌
の生産する環状ペプチドであるデストルキシン〔アグリ
カルチュラル・アンド・バイオロジカル・ケミストリイ
（ＡＨｒｉｃｕｌｔｕｒａｌ ａｎｄ Ｂｉｏｌｏ
ｇｉｃａｌ Ｃｈｅｍｉｓｔｒｙ） 第２６巻、
第３６頁（１９６２年）〕、バチルス屈細菌の生産する
結晶性蛋白質であるデルタ−エンドトキシン〔ａ業と園
芸第４７巻。So far, insecticidal substances originating from microorganisms include destruxin, a cyclic peptide produced by filamentous fungi [AHricultural and Biolo
(Gical Chemistry) Volume 26,
36 (1962)], delta-endotoxin, a crystalline protein produced by Bacillus bacteria [A-Kyo to Horiku Vol. 47.
第１１号、第１５０７頁（１９７２年）〕、放線菌の生
産するピロン系のピエリシジン〔アグリカルチュラル・
アンド・バイオロジカル・ケミストリイ第３０巻、第５
１７頁（１９６６年）〕、ピロリドンを母核とする電子
伝達１１ｆｌ害物質マクロテトロライド群にはいるテト
ラナクチン〔ジャーナル・アンチバイオチフス（Ｊｏｕ
ｒｒ＋ｎｌ Ａｎｔｉｂｉｏｔｌｃｓ）第２４Ａ巻、第
４１８頁（１９７１年）〕１本発明化合物に橘造が類似
したマクロライド系のミルベマイシン〔ザ・ジャーナル
・オン・アンチバイオチフス（Ｔｈａ Ｊｏｕｒｎａｌ
ｏｆ Ａｎｔｉｂｉｏｔｉｃｓ）第２９巻、第７６頁
（１９７６年〕〕、アバメクチン類〔アンチミクロバイ
アル・エイジェンツ・アンド・ケモゼラビイ（Ａｎｔｉ
ｓｉｃｒｏｂｉａｌ Ａｇｅｎｔｓ ａｎｄ Ｃｈａｍ
ｏｔｈａｒｐｙ）第１５巻、ｊ＠３６１頁（１’Ｊ７９
年））、ＬＬ−Ｆ２８２４９α〔ジャーナル゛オンケミ
カル°ソサイアテイ・ケミカル・コミニュケーション（
Ｊｏｕｒｎａｌ ｏｆ Ｃｈａ廁１ｃａｌ ５ｏｃｉｅ
ｔｙ Ｃｈａ會１ｃａｌＣｏ＋＋ｗｕｎ１ｃａｔ１ｏｎ
）第４０２頁（１９８７年）〕が知られている。No. 11, p. 1507 (1972)], pyrone series piericidin produced by actinomycetes [Agricultural
and Biological Chemistry Volume 30, No. 5
17 (1966)], tetranactin, which belongs to the macrotetrolide group of electron transport 11fl harmful substances with pyrrolidone as the mother nucleus [Journal Antibiotic Fever (Jou
rr+nl Antibiotlcs) Volume 24A, Page 418 (1971)] 1 Milbemycin, a macrolide similar to the compound of the present invention by Tachibana [The Journal on Antibiotyphoid Fever (The Journal
of Antibiotics, Volume 29, Page 76 (1976)], Abamectins [Antimicrobial Agents and Chemotherapy (1976)]
ciclobial agents and cham
otharpy) Volume 15, j@361 pages (1'J79
)), LL-F28249α [Journal on Chemical Society Chemical Communication (
Journal of Cha 1cal 5ocie
ty Chakai1calCo++wun1cat1on
), page 402 (1987)] is known.
（発明が解決しようとするｍ１ｌｌ）
本発明は、新規な天然生理活性物質を提供することを目
的とする。(M1ll to be Solved by the Invention) An object of the present invention is to provide a novel natural physiologically active substance.
（課題を解決するための手段）
本発明者らは、新規な微生物生産生理活性物質の探索を
目的に種々の土壌から菌株を分離し、その生産する代謝
産物について研究を続けた結果、土壌より新たに分離し
たＫＳＢ−１９３９株の培養物中に強力な殺虫、殺ダニ
及び駆虫作用を示す活性物質が生産されることを見い出
し、その生理活性物質を単層、採取することに成功した
。(Means for Solving the Problems) The present inventors isolated bacterial strains from various soils for the purpose of searching for novel physiologically active substances produced by microorganisms, and as a result of continuing research on the metabolites produced by the strains, they found that We discovered that an active substance exhibiting strong insecticidal, acaricidal, and anthelmintic effects was produced in a culture of the newly isolated KSB-1939 strain, and succeeded in collecting a monolayer of the physiologically active substance.
すなわち１本発明の生理活性物質は 式 にて示される。That is, one physiologically active substance of the present invention is formula It is shown in
本発明の生理活性物質をＫＳＢ−１９３９Ｓ、と称する
。The physiologically active substance of the present invention is referred to as KSB-1939S.
本発明のＫＳＢ−１９３９Ｓ、は、下記の理化学的性質
を有する。KSB-1939S of the present invention has the following physical and chemical properties.
■物質の色 ：無色
■元素分析値：Ｃ：６９．３８％
Ｉｆ ８．１３％
０：２２．５０％
■分子式 ： Ｃｓ ｔ Ｈｓ ｘ Ｏ−■分子量
： ６４０ （ＦＡＢＭＳ）■紫外線吸収スペクトル
：第１図に示す。■Color of substance: Colorless ■Elemental analysis value: C: 69.38% If 8.13% 0:22.50% ■Molecular formula: Cs t Hs x O- ■Molecular weight
: 640 (FABMS) ■Ultraviolet absorption spectrum: Shown in FIG.
■赤外線吸収スペクトル：第２図に示す。■Infrared absorption spectrum: Shown in Figure 2.
■核磁気共鳴スペクトル：第３図に示す。■Nuclear magnetic resonance spectrum: Shown in Figure 3.
■呈色反応 ニジリカゲル簿層上で
ヨウ素反応 ＋、硫酸反応 ＋、ニンヒドリン反応 −
。■Color reaction Iodine reaction +, sulfuric acid reaction +, ninhydrin reaction - on the Nijirica gel layer
.
アニスアルデヒド反応 −９塩化化第銑鉄応 −５２，
４−ジニトロフェニルヒドラジン反応 十■溶解性
：水に不溶、メタノール、アセトン、酢酸エチル、クロ
ロホルム、ヘキサンに可溶。Anisaldehyde reaction -9 Pig iron chloride reaction -52,
4-dinitrophenylhydrazine reaction
: Insoluble in water, soluble in methanol, acetone, ethyl acetate, chloroform, hexane.
［相］塩基性、ａ性、中性の区分：中性法にＫＳＢ−１
９３９Ｓ、の構造解析について説明する。[Phase] Basic, a-based, neutral classification: KSB-1 for neutral method
The structural analysis of 939S will be explained.
実施例に従って得られたＫＳＢ−１９３９Ｓ、の理化学
的性質、特に紫外線吸収スペクトル、プロトン及びカー
ボン核磁気共鳴スペクトルの解析から、この物質は１６
員マクロライド系物質であり１ｇｔ量分析データ（Ｅ’
Ｉ及びＦＡＢ）で確Ｕされた分子量６４０に該当する既
知のマクロライド物質はなくその新規性が推察できた。From the analysis of the physical and chemical properties of KSB-1939S obtained according to the examples, especially the ultraviolet absorption spectrum, proton and carbon nuclear magnetic resonance spectra, this substance is 16
It is a member macrolide substance, and the 1gt amount analysis data (E'
There is no known macrolide substance that corresponds to the molecular weight of 640 determined by I and FAB), and its novelty can be inferred.
本発明化合物と悶造的に近縁と考えられるミルベマイシ
ン類、アバメクチン類、ＬＬ−Ｆ２８２４９α等は、何
れもストレプトミセスに屑する放線菌の生産する殺虫性
マクロライドと称する物質であり、これらの構造解析に
関して、ミルベマイシンについては、アブストラクト・
ベーバーズ（Ａｂａｓｔｒａｃｔ ｐａｐｅｒｓ）第３
０９〜３１６頁〔第１８回シンポジウム・ケミカル・ナ
チュラル・プロダクツ・キヨウト（Ｓｙｖｐｏｓｉｕｎ
Ｃｈａｍｌｃａｌ Ｎａｔｕｒａｌ Ｐｒｏｄｕｃｔ
ｓ＋ Ｋｙｏｔｏ） （１９７４年１０月１７〜１９
日開催）〕及びテトラヒドロン・レターズ（Ｔａｔｒａ
ｈｅｄｒｏｎ Ｌａｔｔｅｒｓ）第７１１−７１４頁（
１９７５年）に、アバメクチンレこついて、はジャーナ
ル・オン・アメリカン・ケミカル・ソサＩティ（Ｊｏｕ
ｒｎａｌ ｏｆ ＡｍｅｒｉｃａｎＣｈａｍｉｃａｌ
５ｏｅｉａｔｙ）第１０３６．第４２１６−４２２１頁
（１９８１年）に、また、ＬＬ−Ｆ２８２４９について
は、前述の文献に記載されている。Milbemycins, abamectins, LL-F28249α, etc., which are thought to be closely related to the compounds of the present invention, are all substances called insecticidal macrolides produced by actinomycetes that are common to Streptomyces. Regarding analysis, for milbemycin, abstract
Babers (Abstract papers) No. 3
Pages 09-316 [18th Symposium Chemical Natural Products Kiyoto (Syvposiun)
Chamlcal Natural Product
s+ Kyoto) (October 17-19, 1974)
)] and Tetrahydrone Letters (Tatra
hedron latters) pages 711-714 (
In 1975), Abamectin was used in the Journal of the American Chemical Society.
rnal of american chemical
5oeiaty) No. 1036. 4216-4221 (1981), and LL-F28249 is described in the above-mentioned literature.
本発明のＫＳＢ−１９３９５，の諸データを、これら文
献に示された構造解析データを参考にして検討した結果
。The results of examining the various data of KSB-19395 of the present invention with reference to the structural analysis data shown in these documents.
■基本骨格は、ザ・ジャーナル・オン・アンチバイオチ
フス第３３巻、第１１２１頁（１９８０年）に記載のラ
クトン環をもった前述の式（１）で示されるものである
こと、■マクロライド環の１３位には、アバメクチンに
みられる糖側鎖が存在しないこと。■The basic skeleton is one shown by the above formula (1) with a lactone ring as described in The Journal on Antibiotics, Volume 33, Page 1121 (1980), ■Macrolide There is no sugar side chain found in abamectin at the 13th position of the ring.
■スビラ環上の２４位にメチル基及び２５位にエチル基
を有していること、
■ＫＳＢ−１９３９Ｓ５の特徴は５４位の炭素につなが
る側鎖にあり、マクロライド環４位の炭素に３−メチル
−２＝ブテノイルオキシメチル基が連結していること、
が解析でき、前述の式（１）で示される新規物質と決定
した。■KSB-1939S5 has a methyl group at the 24th position and an ethyl group at the 25th position on the subira ring. ■The characteristics of KSB-1939S5 are the side chain connected to the 54th carbon, and the 3rd carbon at the 4th position of the macrolide ring. -Methyl-2=butenoyloxymethyl group is connected,
could be analyzed and determined to be a new substance represented by the above-mentioned formula (1).
本発明のＫＳＢ−１９３９ｓ、の生産菌の一例としては
。An example of a producing strain of KSB-1939s of the present invention is:
本発明者らによって和歌山系新宮市街の土壌から分離さ
れた放線菌ＫＳＢ−１９３９株がある。ＫＳＢ−１９３
９株の菌学的性質は１次の通りである。There is an actinomycete KSB-1939 strain that was isolated from the soil of Shingu City in the Wakayama region by the present inventors. KSB-193
The mycological properties of the nine strains are as follows.
本菌株の同定は１国際ストレプトミセス計画（Ｉ Ｓ
Ｐ）の方法とワックスマン氏の方法により、その記載は
ＩＳＰの例に準じて行なった。The identification of this strain was carried out by the International Streptomyces Project (IS).
The description was made according to the example of ISP using the method of P) and Mr. Waxman's method.
（１）形態的性質
双生菌糸は、分岐しながら生長し、菌糸の分断は、観察
されない、気中菌糸は、グルコース・アスパラギン寒天
培地、オートミール寒天培地等で旺盛に着生し胞子形成
も良好である。気中菌糸は１分岐しながら空中に伸長し
短い主軸又は分枝上に胞子鎖を車軸分岐する。胞子鎖は
２通常コイル状螺旋を呈する。長期間培養すると、胞子
鎖先端が黒粘貿塊化し。(1) Morphological properties Twin hyphae grow while branching, and hyphal division is not observed.Aerial hyphae adhere vigorously on glucose-asparagine agar medium, oatmeal agar medium, etc., and have good sporulation. be. Aerial hyphae extend into the air while branching, and the spore chains are branched onto short main axes or branches. The spore chains exhibit two usually coiled helices. When cultured for a long period of time, the tip of the spore chain turns into a black clay mass.
更に進んだ部分は、気中菌糸全体が黒褐色粘質塊化する
（グルコース・アスパラギン寒天培地、オートミール寒
天培地）。In further advanced areas, the entire aerial mycelium becomes a blackish-brown sticky mass (glucose-asparagine agar medium, oatmeal agar medium).
胞子鎖の幅は２０．５ないし０．８ミクロン、胞子表面
は、シワ状（Ｖａｒｔｙ）を呈し胞子の区切りが不鮮明
なため、詳しい個々の胞子の形状及び連結数は、不明で
あるが１０胞子以上の連結が詔められる。また胞子は、
運動性を示さず、胞子嚢、菌核等は、ＩＩｌ祭されない
。The width of the spore chain is 20.5 to 0.8 microns, and the spore surface is wrinkled and the divisions between the spores are unclear, so the detailed shape of each spore and the number of connections are unknown, but there are about 10 spores. The above connections are recommended. Also, the spores are
Sporangia, sclerotia, etc. are not motile and are not cultivated.
（２）ジアミノピメリン酸分析
全菌体加水分解物のＬＬ−ジアミノピメリン酸が認めら
れ細胞壁タイプＩ型である。(2) Diaminopimelic acid analysis LL-diaminopimelic acid was observed in the whole bacterial cell hydrolyzate, indicating cell wall type I.
（３）各種培地における生育状態 培養３Ａ間目の生育状態は、第１表に示す通りである。(3) Growth status in various media The growth status of the 3A period of culture is as shown in Table 1.
（４）生理的性質
■生育温度範囲 ２０〜４０℃最適温度範囲
２５〜３５℃■ゼラチンの液化
十
■Ｒ粉の加水分解 十
■脱脂牛乳の凝固 十
ペプトン化 十
■メラニン様色素の生成
チロシン寒天培地 −ペプトン・イ
ースト・鉄寒天培地 −トリプトン・イースト・ブ
ロス −■硝酸塩の還元
十（５）各炭素源の同化性
（プリドハム・ゴドリーブ寒天培地上）Ｌ−アラビノー
ス、Ｄ−キシロース、Ｄ−グルコース、Ｄ−フラクトー
ス、シュクロース、Ｌ−ラムノース、ラフィノース、Ｄ
−マンニトール、Ｌ−イノシトールの全ての炭素源を同
化する。(4) Physiological properties ■ Growth temperature range 20-40℃ Optimum temperature range 25-35℃ ■ Liquefaction of gelatin
10 ■ Hydrolysis of R flour 10 ■ Coagulation of skim milk 10 Peptonization 10 ■ Production of melanin-like pigment Tyrosine agar medium - Peptone yeast iron agar medium - Tryptone yeast broth - ■ Reduction of nitrates
(5) Assimilation of each carbon source (on Pridham-Godelieve agar medium) L-arabinose, D-xylose, D-glucose, D-fructose, sucrose, L-rhamnose, raffinose, D
-Assimilates all carbon sources of mannitol, L-inositol.
上記の菌学的性質をインターナショナル・ジャーナル・
オン・システマチック・バクテリオロジー（■ｎｔｅｒ
ｎａｔｉｏｎａｌＪｏｕｒｎａｌ ｏｆ Ｓｙｓｔｉｍ
ａｔｉｃ Ｂａｃｔｅｒｉｏｌｇｙ）第２２巻、第３０
７〜３１１頁（１９７２年）の記載を参照し同定を行っ
た結果。The above mycological properties were published in the International Journal
On Systematic Bacteriology (■nter
National Journal of System
atic Bacteriology) Volume 22, No. 30
Results of identification with reference to the description on pages 7-311 (1972).
ＫＳＢ−４９３９株は、シュクロース、ラフィノースの
同化の点で僅かに差を詔めるものの、基本性状（形態及
び各種培地での生育状態）がストレプトミセス・バイグ
ロスコピカス（Ｓｔｒｅｐｔｏｍｙｃｅｓ ｈｙｇｒｏ
ｓｃｏｐｌｃｕｓ） とよく一致することから。Although there are slight differences in the assimilation of sucrose and raffinose, the KSB-4939 strain has basic properties (morphology and growth status on various media) that are similar to Streptomyces hygroscopicus.
scoplcus).
ストレプトミセス・バイグロスコピカス ＫＳＢ−１９
３９と命名しｆ：、ＫＳ［３−１９３９株は、Ｈａ相和
６２年６月２日付で微工研菌寄第９４３６号（ＦＥＲＭ
Ｐ−９４３６）として寄託されている。尚、ＫＳＢ−１
９３９株は、他の放線菌の場合にみられるように、その
性状が変化しやすい０例えば、ＫＳ［３−，１９３９株
又はこの株に出来する突然変異株（自然発生又は誘発性
）、形質融合体又は遺伝子組換え体であっても、ＫＳｎ
−１９３９株にその形質起源を依存しＫＳＢ−１９３Ｏ
Ｓ、を生産するものは総て本発明に使用出来る。Streptomyces vigroscopicus KSB-19
39, f:, KS [3-1939 strain was published in Ha-Aiwa on June 2, 1962, as published in FERM
P-9436). Furthermore, KSB-1
The 939 strain is susceptible to changes in its properties, as seen in the case of other actinomycetes. Even if it is a fusion or genetically recombinant, KSn
KSB-193O depends on the -1939 strain for its trait origin.
All those that produce S can be used in the present invention.
また１本発明の製造法は、ＫＳＢ−１９３９株の培養と
培養物からの生理活性物質のＪｌｌ＋出、希製からなる
。The production method of the present invention comprises culturing the KSB-1939 strain, extracting and diluting a physiologically active substance from the culture.
すなわち、培養に当ってＫＳＢ−１９３９株を通常の微
生物が利用しうろ栄養物を含有する培地で培養する。栄
養源としては、従来放線菌の培養に利用されている公知
のものが使用できろ６例えば、炭素源として、グルコー
ス、グリセリン、マルトース、ラクトース、水＆＋、デ
キストリン、澱粉、動植物油等を使用できる。またｇ素
源としては、ビースト、大豆粉、／ＪＸ麦胚芽、コーン
ステイープリカー、落花生粉、綿実粉。That is, during culturing, strain KSB-1939 is cultured in a medium containing nutrients used by ordinary microorganisms. As the nutrient source, known ones that have been conventionally used for culturing actinomycetes can be used.6 For example, as the carbon source, glucose, glycerin, maltose, lactose, water &+, dextrin, starch, animal and vegetable oils, etc. can be used. . In addition, the g sources include beast, soybean flour, /JX wheat germ, cornstarch liquor, peanut flour, and cottonseed flour.
ペプトン、肉エキス、酵母エキス、硫酸アンモニウム、
硝酸ソーダ、９素等が使用できる。その他、必要に応じ
て、ナトリウム、カリウム、カルシウム、マグネシウム
、コバルト。Peptone, meat extract, yeast extract, ammonium sulfate,
Sodium nitrate, 9 elements, etc. can be used. In addition, sodium, potassium, calcium, magnesium, and cobalt as required.
塩！＋１ＡＭ、硫酸及びその他のイオンを生成すること
が出来る無機塩類を添加することも有効である。また菌
の発育を助け、ＫＳＢ−１９３９Ｓ、の生産を促進する
ような有機物及び無機物を適男に添加することも出来る
。salt! It is also effective to add inorganic salts capable of producing +1 AM, sulfuric acid and other ions. It is also possible to add organic and inorganic substances to the mixture that aid the growth of bacteria and promote the production of KSB-1939S.
培養法としては、好気的条件下での培養法、特に深部タ
ンク培養法が最も適している。培養に適当な温度は、１
５〜３７℃であるが、多くの場合、２６〜３０℃付近で
培養する。The most suitable culture method is a culture method under aerobic conditions, especially a deep tank culture method. The appropriate temperature for culturing is 1
The temperature is 5 to 37°C, but in many cases it is cultured at around 26 to 30°C.
ＫＳＢ−１９３９ｓ、の生産は、培地や培養条件により
異なるが、浸透培養、タンク培養とも５〜１０日の間で
その培養が最高に達する。The production of KSB-1939s varies depending on the medium and culture conditions, but the culture reaches its maximum within 5 to 10 days in both infiltration culture and tank culture.
このようにして生産されたＫＳＢ−１９３９Ｓ、はその
理化学的性質に従って培養物から抽出、精製することが
可能であるが、特に以下の方法により効率的に抽出、精
製出来る。KSB-1939S produced in this manner can be extracted and purified from the culture according to its physicochemical properties, and in particular can be efficiently extracted and purified by the following method.
すなわち、ＫＳＢ−１９３９５ｓの大部分は培養菌体中
に生産されるので、培養物は濾過又は遠心分離によって
菌体を分離し、菌体を分離し、菌体をアセトン又はアル
コールで抽出し、抽出液を減圧濃縮後、酢酸エチル、ク
ロロホルムのような転溶性溶剤に転溶させるか、いきな
り培養物又は濃縮液を前述のような転溶性溶剤にて抽出
する。転溶液を濃縮乾燥させるとＫＳＢ−１９３９５，
を含む粉末又は油状の粗製品を得ることが出来る。That is, since most of KSB-19395s is produced in cultured bacterial cells, the cultured cells are separated by filtration or centrifugation, the bacterial cells are separated, and the bacterial cells are extracted with acetone or alcohol. After concentrating the liquid under reduced pressure, it is dissolved in a transferable solvent such as ethyl acetate or chloroform, or the culture or concentrate is immediately extracted with a transferable solvent such as those described above. When the inverted solution is concentrated and dried, KSB-19395,
It is possible to obtain a powder or oily crude product containing.
粗製品は、ＫＳＢ−１９３９Ｓ、を含む複数の殺虫性Ｉ
！１＃物質の混合物として得られるため、脂溶性物質の
精製に通常用いられる公知の方法１例えばシリカゲル、
アルミナ等の担体を用いたカラムクロマトグラフィーに
より分画精製することが必要である。このクロマトグラ
フィーの条件の選択により本発明のＫＳＢ−１９３９Ｓ
５を高収率でかつ高純度で得ることが出来るが、更に、
純化界を採取する場合には、精製品のＭｙ！Ｊ又は逆層
カラムを用いた高速液体クロマトグラフィーによる分画
が有効である。この他にゲル濾過法、吸着剤を用いた分
画法、結晶化等の方法の採用も可能である。The crude product contains several insecticidal compounds, including KSB-1939S,
! 1 # Known methods commonly used for purification of fat-soluble substances because they are obtained as a mixture of substances 1 For example, silica gel,
It is necessary to carry out fractional purification by column chromatography using a carrier such as alumina. By selecting these chromatography conditions, the KSB-1939S of the present invention
5 can be obtained in high yield and high purity, but furthermore,
When collecting purified world, use the purified product My! Fractionation by high performance liquid chromatography using a J or reverse phase column is effective. In addition, it is also possible to employ methods such as gel filtration, fractionation using an adsorbent, and crystallization.
次に、実施例を挙げて具体的に説明するが本物質の製造
法はこれに限定されるものではない。Next, the present substance will be specifically explained with reference to examples, but the method for producing this substance is not limited thereto.
実施例 Ｉ
ＫＳＢ−１９３９株の継代スラントからその１片を、麦
芽エキス１．０％、酵母エキス０．４％、グルコース０
．４％。Example I One piece from the subculture slant of KSB-1939 strain was treated with 1.0% malt extract, 0.4% yeast extract, and 0 glucose.
．． 4%.
脱脂大豆０．２％の組成からなる種培養培地１００ｍＱ
を入れた５００ｍＡ三角フラスコに移し、振どう培養機
にて、２８℃で３日１１１１種培養を行った１次にｌｉ
ｔ粉３％、酵母エキス０゜５％、コーンスチーブリ力−
０．５％、燐酸二カリウム０．２％、硫酸マグネシュウ
ム０．０５％、プロナール５０２（１２逍：東邦化学工
業株式会社）０．０５％の組成からなる２゜Ｑの生産用
培地をジャーファーメンタ−に入れ、滅菌冷却後、１１
Ｍ述の種培養液を接種し、通気量２０１２／毎分１、培
養温度２８℃１回転数１５０回転／毎分の条件にて９日
間培養を行った。培養終了後、セライトを助剤として吸
引濾過を行い、菌体を集めた。ａ菌体を１０Ｑのアセト
ンに分散させ、１時間撹拌して抽出を行った後、濾過に
より清澄なアセトン液を回収した１次いで減圧濃縮にて
アセトンを除去し、水２００ｍａにて残留物を洗い集め
た後、酢酸エチル５００ｍＱにて２回転溶抽出を行った
。酢酸エチル転溶成約１αに無水硫酸ナトリウム５０ｇ
を加えて脱水し、減圧濃縮して酢酸エチルを外し油状物
質的６ｇを回収した。クロロホルム９５重量部に重量５
部のアセトンを加えた展開液少量に油状物質を溶解し。Seed culture medium 100mQ consisting of 0.2% defatted soybean
1111 seeds were cultured for 3 days at 28°C in a shaking incubator.
T-flour 3%, yeast extract 0.5%, cornstarchy
A 2°Q production medium consisting of 0.5% dipotassium phosphate, 0.2% magnesium sulfate, 0.05% magnesium sulfate, and 0.05% Pronal 502 (12th grade: Toho Chemical Industry Co., Ltd.) was used in Jafar. Place in a mentor, sterilize and cool, then
The seed culture solution described in M was inoculated and cultured for 9 days under the conditions of an aeration rate of 2012/min, a culture temperature of 28°C, and a rotation speed of 150 revolutions/min. After the culture was completed, the cells were collected by suction filtration using Celite as an auxiliary agent. Disperse the bacterial cells in 10Q acetone, stir for 1 hour for extraction, and collect the clear acetone solution by filtration.1 Next, remove the acetone by vacuum concentration, and wash the residue with 200mA of water. After collection, elution extraction was performed twice with 500 mQ of ethyl acetate. 50g of anhydrous sodium sulfate to about 1α of ethyl acetate
was added to remove the ethyl acetate and concentrated under reduced pressure to recover 6 g of oily substance. 95 parts by weight of chloroform and 5 parts by weight
Dissolve the oily substance in a small amount of developing solution with acetone added.
内径５０ｍｍ、高さ６５０ｍｍのカラムを用いてシリカ
ゲルクロマトグラフィーを行った。２Ｏｍｊｌずつに分
取したフラクションの活性画分を集め、減圧乾燥を行う
ことによりＫＳＢ−１９３９５，の２２％を含有する混
合粗精製粉末９０ｍｇを採取した。Silica gel chromatography was performed using a column with an inner diameter of 50 mm and a height of 650 mm. The active fractions were collected in 20 mjl fractions and dried under reduced pressure to obtain 90 mg of mixed crude powder containing 22% of KSB-19395.
実施例 ２
実施例 １に記載した粗製品５０ｍｇを２ｍｆｉのアセ
トニトリルに溶解し、内径２０ｍｍ、長さ２５０ｍｍの
ＯＤＳカラムをセットした分取用高速液体クロマトグラ
フィーに注入した。８０％アセトニトリル１０ｍ１１／
毎分を溶出液として流し、２４０ｍｍの紫外部吸収によ
り検出してＫＳＢ−１９３９Ｓ、の活性画分を採取し１
分画液を濃縮乾固することにより純度６５％のＫＳＢ−
１９３９Ｓ５含有物１５ｍｇを得た。更に、内径２０ｍ
ｍ、長さ２５０ｍｍのシリカゲルカラムをセットし九分
取用液体クロマトグラフィーにＫＳＢ−１９３９Ｓ、の
６５％含有物をヘキサン１ｍｊｌに溶解注入しヘキサン
及びイソプロピルアルコールの混合液（９８：２）で展
開してＫＳＢ−１９３９５，画分を集め減圧乾燥するこ
とにより純化界８．５ｍｇを採取した。Example 2 50 mg of the crude product described in Example 1 was dissolved in 2 mfi acetonitrile and injected into a preparative high performance liquid chromatography equipped with an ODS column with an inner diameter of 20 mm and a length of 250 mm. 80% acetonitrile 10ml/
The active fraction of KSB-1939S was collected every minute as an eluent and detected by ultraviolet absorption at 240 mm.
By concentrating the fraction to dryness, KSB-
15 mg of 1939S5-containing material was obtained. Furthermore, the inner diameter is 20m
A silica gel column with a length of 250 mm was set and a 65% content of KSB-1939S was dissolved in 1 mjl of hexane and injected into a preparative liquid chromatography system, and developed with a mixture of hexane and isopropyl alcohol (98:2). KSB-19395 was collected, and the fractions were collected and dried under reduced pressure to obtain 8.5 mg of purified product.
以下余白
本発明化合物を殺虫殺ダニ剤として使用するには１本発
明化合物それ自体で用いてもよいが、通常は担体、界面
活性剤、分散剤又は補助剤等を配合して常法により、粉
剤、水和剤。To use the compound of the present invention as an insecticide and acaricide, the compound of the present invention may be used by itself, but it is usually mixed with a carrier, a surfactant, a dispersant, or an auxiliary agent, etc., and then used in a conventional manner. Powders, hydrating agents.
乳剤、微粒剤又は粒剤等に製剤して使用する。担体とし
ては。It is used in formulations such as emulsions, microgranules, or granules. As a carrier.
タルク、ベントナイト、クレー、カオリン、珪藻土、ホ
ワイトカーボン、バーミュライト、消石灰、珪砂、ｍ安
、尿素等の固体担体及びトルエン、メチルエチルケトン
、メチルナフタリン、イソプロピルアルコール、キシレ
ン、シクロヘキサノン等の散体担体が挙げられる。界面
活性剤及び分散剤としては１例えば、ジナフチルメタン
ジスルホン酸塩、アルコール硫酸エステル塩、アルキル
アリールスルホン酸塩、リグニンスルホン酸塩、ポリオ
キシエチレングリコールエーテル。Solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermulite, slaked lime, silica sand, ammonium, urea, etc., and powder carriers such as toluene, methyl ethyl ketone, methyl naphthalene, isopropyl alcohol, xylene, cyclohexanone, etc. It will be done. Examples of surfactants and dispersants include dinaphthylmethane disulfonate, alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, and polyoxyethylene glycol ether.
ポリオキシエチレンアルキルアリールエーテル、ポリオ
キシエチレンソルビタンモノアルキレート等が挙げられ
る。補助剤としてカルボキシメチルセルロース、ポリエ
チレングリコール、アラビアゴム等が挙げられる。これ
らの製剤は、適宜な一度に希釈して散布するか、又はｉ
ｉ！接施用する。Examples include polyoxyethylene alkylaryl ether and polyoxyethylene sorbitan monoalkylate. Examples of adjuvants include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. These preparations can be diluted and applied at any suitable time, or i.
i! apply.
次に本発明の製剤例を挙げて具体的に説明する。下記製
剤例中の％は１重量百分率を示す。Next, the present invention will be specifically explained with reference to formulation examples. % in the following formulation examples indicates 1 weight percentage.
製剤例１ 粉 剤
ＫＳＢ−１９３９５，０，５％、珪藻土５％及びクレー
９４゜５％を均一に混合し粉砕して粉剤とした。Formulation Example 1 Powder KSB-19395, 0.5%, diatomaceous earth 5% and clay 94.5% were uniformly mixed and pulverized to obtain a powder.
製剤例２ 水和剤
ＫＳＢ−１９３９３，２％、珪藻±５３％、クレー４０
％、ジナフチルメタンジスルホン醜ナトリウム２％及び
リグニンスルホン酸ナトリウム３％を均一に混合し粉砕
して水和剤とした。Formulation example 2 Wettable powder KSB-19393, 2%, diatom ±53%, clay 40
%, 2% sodium dinaphthylmethanedisulfonate, and 3% sodium ligninsulfonate were uniformly mixed and pulverized to prepare a wettable powder.
製剤例３ 乳 剤
ＫＳＢ−１９３９Ｓ、５％、キシレン３０％、ポリオキ
シエチレンアルキルアリールエーテル１１％、アルキル
ベンゼンスルホン酸カルシウム４％及びメチルナフタリ
ン５０％を均一に溶解して乳剤とした。Formulation Example 3 Emulsion An emulsion was prepared by uniformly dissolving 5% KSB-1939S, 30% xylene, 11% polyoxyethylene alkylaryl ether, 4% calcium alkylbenzenesulfonate, and 50% methylnaphthalene.
製剤例４ 粒 剤
ＫＳＢ−１９３９Ｓ５０，５％、ラウリルアルコール硫
酸エステルのナトリウム塩２％、リグニンスルホン酸ナ
トリウム５％、カルボキシメチルセルロース
％を均一に混合粉砕する．この混合物１００重量部に水
２０重量部を加えて練合し、押出式造粒機を用いて１４
〜３２メツシユの粒状に加工したのち、乾燥して粒剤と
した。Formulation Example 4 Granules 50.5% of KSB-1939S, 2% of sodium salt of lauryl alcohol sulfate, 5% of sodium lignin sulfonate, and % of carboxymethyl cellulose are uniformly mixed and ground. Add 20 parts by weight of water to 100 parts by weight of this mixture, knead it, and use an extrusion type granulator for 14 parts by weight.
After processing into granules of ~32 meshes, they were dried to form granules.
（発明の効果）
本発明化合物は，農業用殺虫殺ダニ剤，殺虫性医薬品，
家畜・ペット用駆虫剤，防虫・防蟻剤，衛生ｍ殺虫殺ダ
ニ剤として有用である．本発明化合物は，構造の類似し
た公知物質であるアパメクチンと比較しても優れた殺虫
活性を示すものである。(Effects of the invention) The compounds of the present invention can be used as agricultural insecticides, acaricides, insecticidal pharmaceuticals,
It is useful as a dewormer for livestock and pets, an insect repellent/termite repellent, and a sanitary insecticide and acaricide. The compound of the present invention exhibits superior insecticidal activity compared to apamectin, a known substance with a similar structure.
次に本発明化合物の奏する効果を試験例を挙げて具体的
に説明する。Next, the effects of the compounds of the present invention will be specifically explained using test examples.
試験例１ ナミハダニ殺成虫試験
径５５ｍｍのポリエチレン製カップに水を注ぎ、中心に
径１０ｍｍの穴を開けた蓋をし、蓋の穴から脱脂綿を垂
らして水を吸い上げるようにした後、蓋の上にろ紙をの
せ、その上にインゲンのリーフディスクを２枚置き，デ
ィスクに常に水が供給されるようにした．毛筆を用いて
リーフディスク当り１０頭のナミハダニ雌成虫を接種し
，２４時間後に異常虫を取り除き、製剤例２に準じて調
製した水和剤を所定１度に希釈し，薬液が２ｍｇ／ａｍ
’相当量となるように散布した。Test example 1 Two-spotted spider mite adult insecticidal test Pour water into a polyethylene cup with a diameter of 55 mm, cover with a lid with a hole of 10 mm in diameter in the center, drop absorbent cotton from the hole in the lid to absorb the water, and place on the lid. A filter paper was placed on top of the filter paper, and two green bean leaf disks were placed on top of the filter paper to ensure that water was constantly supplied to the disks. Using a brush, 10 adult female two-spotted spider mites were inoculated per leaf disk, and after 24 hours, the abnormal insects were removed, and the wettable powder prepared according to Formulation Example 2 was diluted to a predetermined degree, so that the chemical solution was 2 mg/am.
'It was sprayed in a considerable amount.
試験は，２連にて行い，薬剤処理２日後に実体顕微鏡に
てダニの生死を判定し．下記の計算式により補正死出率
を算出した．尚、アバメクチンは．Ｃ−０７６−Ｂｌａ
（８０％以上）及びＣ−０７６−Ｂｉｂ （２０％以
下）の混合物を比較剤として供試した．結果を第２表に
示す。The test was conducted in duplicate, and two days after the drug treatment, the survival of the mites was determined using a stereomicroscope. The corrected mortality rate was calculated using the formula below. Furthermore, abamectin is... C-076-Bla
(80% or more) and C-076-Bib (20% or less) was used as a comparison agent. The results are shown in Table 2.
試験例２ トビイロウンカ殺虫試験
製剤例２に準じて調製した水和剤を所定濃度に水で希釈
ル・これに稲茎葉を浸漬し風乾した後，試験管に入れた
．その中にトビイロウンカ幼虫１０１７ｊ［を放ち，脱
脂綿で詮をして２５℃の恒温にて５日間飼育した．試験
は，２連にで行い．飼育後の死出率を算出した．結果を
第３表に示す。Test Example 2 Brown Planthopper Insecticide Test A wettable powder prepared according to Preparation Example 2 was diluted with water to a specified concentration. Rice stalks and leaves were immersed in this solution, air-dried, and then placed in a test tube. Brown planthopper larvae 1017j were released into the larvae, and the larvae were covered with absorbent cotton and kept at a constant temperature of 25°C for 5 days. The test was conducted in two series. The mortality rate after rearing was calculated. The results are shown in Table 3.
試験例３ ニカメイチュウ殺虫試験
製剤例２に準じてＦＩＩＩＩした水和剤を所定濃度に水
で希釈し。Test Example 3 A wettable powder prepared according to Preparation Example 2 was diluted with water to a predetermined concentration.
これに稲芽出し籾を浸漬し風乾した後，径５５ｍｍのポ
リエチレン製カップに入れた．その中にニカメイチュウ
３齢幼虫１０１？［を放ち、２５℃の恒温にて５日間飼
育した．試験は、２連にて行い．飼育後の死出率を算出
した．結果を第４表に示す。The sprouted paddy was soaked in this, air-dried, and then placed in a polyethylene cup with a diameter of 55 mm. Is there 101 3rd instar nymphs among them? [] and reared at a constant temperature of 25°C for 5 days. The test was conducted in two series. The mortality rate after rearing was calculated. The results are shown in Table 4.
第１図は．ＫＳＢ−１９３９Ｓ５の紫外線吸収スペクト
ルを、第２図は、ＫＳＢ−１９３９５，の赤外線吸収ス
ペクトルを，第３図は、ＫＳＢ−１９３９Ｓ．のプロト
ン核磁気共鳴スペクトルを示す。Figure 1 is. Figure 2 shows the ultraviolet absorption spectrum of KSB-1939S5, Figure 3 shows the infrared absorption spectrum of KSB-19395, and Figure 3 shows the infrared absorption spectrum of KSB-1939S. This shows the proton nuclear magnetic resonance spectrum of .
Claims (1)
＿５化合物の生産菌を培養し、培養物から当該化合物を
採取することを特徴とする当該化合物の製造法。[Claims] (1) A KSB-1939S_5 compound represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. are available. (4) KSB-1939S belonging to the genus Streptomyces
_5 A method for producing a compound, which comprises culturing a producing bacterium and collecting the compound from the culture.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2254388A JPH01197488A (en) | 1988-02-02 | 1988-02-02 | Physiologically active substance ksb-1939 compound and production thereof |
| EP88110715A EP0298423A3 (en) | 1987-07-07 | 1988-07-05 | Antibiotic ksb-1939 compounds and production process thereof as well as pesticidal agents containing same |
| AU18698/88A AU615921B2 (en) | 1987-07-07 | 1988-07-05 | Antibiotic ksb-1939 compounds and production process thereof as well as pesticidal agents containing same |
| BR8803371A BR8803371A (en) | 1987-07-07 | 1988-07-06 | PESTICIDE COMPOUND, PROCESS FOR ITS PRODUCTION AND PESTICIDE AGENT |
| CN88104219A CN1030790A (en) | 1987-07-07 | 1988-07-07 | KSB-1939 compound, its method for making of antibiosis arranged and contain the sterilant of this compounds |
| KR1019880008427A KR890002163A (en) | 1987-07-07 | 1988-07-07 | Antimicrobial KSB-1939 compound and preparation method thereof and pesticide containing the same |
| US07/216,128 US4939166A (en) | 1987-07-07 | 1988-07-07 | Antibiotic KSB-1939 compounds as well as pesticidal agents containing same |
| US07/512,126 US5091311A (en) | 1987-07-07 | 1990-04-17 | The production of ksb-1939 macrolides using str eptomyces hygroscopicus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2254388A JPH01197488A (en) | 1988-02-02 | 1988-02-02 | Physiologically active substance ksb-1939 compound and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01197488A true JPH01197488A (en) | 1989-08-09 |
Family
ID=12085737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2254388A Pending JPH01197488A (en) | 1987-07-07 | 1988-02-02 | Physiologically active substance ksb-1939 compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01197488A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008191A (en) * | 1986-12-11 | 1991-04-16 | Sankyo Company Limited | Macrolide compounds, their preparation and their use |
| US5212322A (en) * | 1986-12-11 | 1993-05-18 | Sankyo Company, Limited | Macrolide compounds, their preparation and their use |
-
1988
- 1988-02-02 JP JP2254388A patent/JPH01197488A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008191A (en) * | 1986-12-11 | 1991-04-16 | Sankyo Company Limited | Macrolide compounds, their preparation and their use |
| US5212322A (en) * | 1986-12-11 | 1993-05-18 | Sankyo Company, Limited | Macrolide compounds, their preparation and their use |
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