CN1948256A - New compound possessing insecticidal bactericidal activity - Google Patents
New compound possessing insecticidal bactericidal activity Download PDFInfo
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- CN1948256A CN1948256A CN 200510112916 CN200510112916A CN1948256A CN 1948256 A CN1948256 A CN 1948256A CN 200510112916 CN200510112916 CN 200510112916 CN 200510112916 A CN200510112916 A CN 200510112916A CN 1948256 A CN1948256 A CN 1948256A
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- herba lycopi
- new compound
- bactericidal activity
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Abstract
The present invention provides a new compound-eupatoria C, its chemical name is 8 alpha-hydroxy-1-isopropyl-4,7-dimethyl-1,3,4,8 alpha-tetralyl-2,6-diketone. It belongs to a hemiterpene compound. Said invention also provides its physical and chemical properties and spectral data. Said compound can be used as high-effective mycocide and pesticide or repellent of some crops.
Description
Technical field
The present invention relates to a kind of new compound, belong to sesquiterpenoid with desinsection, anti-microbial activity.
Background technology
Hemp Eupatorium (Eupatorium adenophorum Spreng) is the perennial subshrub plant of composite family Eupatorium, originates in Central America Mexico, therefrom remote before and after the fifties in last century, in more the border import the Yunnan Province of China south into.This kind of plant has surprising fecundity, can form intensive single kind of advantage group in blocks, repels the growth of other plant.Over nearly 30 years, Hemp Eupatorium almost with annual 30 kilometers speed northwards, rapidly spread eastwards, distribution range has reached provinces and regions such as Yunnan, Guizhou, Guangdong, Guangxi, Sichuan, Tibet, only state, the Liangshan Mountain, Sichuan hazard area just reaches more than 670,000 hectares at present, herds sideline production for the agricultural that spread the district and has brought serious harm.
For fully fully utilizing this malignant weed, it is changed harmful to treasure.This case discloses new compound Herba Lycopi C and nematicide and anti-microbial activity first, for new approaches are opened up in the Hemp Eupatorium comprehensive utilization.
Summary of the invention
The purpose of this invention is to provide a kind of desinsection, antimicrobial new compound---Herba Lycopi C that has.
Herba Lycopi C provided by the invention is a kind of new compound, its chemistry 8 Alpha-hydroxies by name-1-sec.-propyl-4,7-dimethyl-1,3,4,8a-tetrahydrochysene how-2, and the 6-diketone belongs to sesquiterpenoids.
Physico-chemical property and the spectroscopic data of compound Herba Lycopi C are as follows:
1, colourless bulk crystals is soluble in acetone, chloroform;
2、Mp：156℃；[α]
D＝+64°(c＝0.45，CHCl
3)；EIMS(m/z)：248(M+，C
15H
20O
3，35)，230(65)，189(43)，178(100)，163(86)，150(97)；IR(KBr)max(cm
-1)：3320，1719，1666，1623，1387，1160，1995；
3, the X-single crystal diffraction crystal data of Herba Lycopi C sees Table 1:
The structural formula of compound Herba Lycopi C is:
The X-single crystal diffraction crystal data of table 1. Herba Lycopi C
| Empirical formula M T/K Wavelength/ Crystal system space group a/ b/ c/ β/° V/ 3 | C 15H 20O 3 248.31 293(2) 0.71073 Orthorhombic P2(1)2(1)2(1) 8.2082(16) 9.5889(19) 17.340(4) 90 1364.8(5) | Z D c/mg m -3 μ/mm -1 F(000) Reflections collected/unique Data/restraints/parameters Goodness-of-fit on F 2 Final R indices[I＞2sigma(I)] R indices(all data) | 4 1.208 0.083 536 7472/1757 1757/0/164 1.021 R 1＝0.0541，wR 2＝0.1689 R 1＝0.0611，wR 2＝0.1769 |
The affirmation of compound Herba Lycopi C:
By the X-single crystal diffraction, referring to accompanying drawing 1 (CCDC 283245), can confirm this structure for [I], and provide the real structure of compound by X-single crystal diffraction spectrum: 8 Alpha-hydroxies-1-sec.-propyl-4,7-dimethyl-1,3,4,8a-tetrahydrochysene how-2,6-diketone.The methyl of this compound and sec.-propyl are in same one side, and hydroxyl is at another side.To propose especially be sec.-propyl on this sesquiterpene C-1 position and the methyl on the C-4 position in same direction, hydroxyl connects on the C-8a position, why this structure can stable existence be because hydroxyl and carbonyl have formed intermolecular hydrogen bond, referring to accompanying drawing 1.
The extraction step of compound Herba Lycopi C is as follows:
1, get exsiccant Hemp Eupatorium leaf 1Kg, with 8 times of amounts of 95% industrial methanol, soaking at room temperature 48 hours, extract 3 times, filter the back merging filtrate, concentrating under reduced pressure filtrate gets total medicinal extract.
2, (medicinal extract: dissolving methyl alcohol=10: 1) adds water (methyl alcohol: water=2: 8) to total medicinal extract then with methyl alcohol.Use sherwood oil, chloroform, ethyl acetate extraction successively, concentrated extract gets sherwood oil medicinal extract (157g), chloroform medicinal extract (24g), ethyl acetate medicinal extract (230g) and residue respectively.
3, chloroform medicinal extract (24g) is through 200～300 order silica gel column chromatographies, with sherwood oil: 20: 1～5: 1 gradient elutions of acetone, adopt TLC to follow the tracks of and detect, every 250ml connects one bottle, merge same composition after, obtain 11 B component a～Bk.Be component silica gel column chromatography, use sherwood oil: acetone (10: 1) wash-out, collect Be1, Be2, Be3, Be4 component; Be2 component acetone recrystallization obtains colourless consolidated block compound Herba Lycopi C, Herba Lycopi C through the chloroform/methanol mixed solvent cultivate the monocrystalline of the alleged Herba Lycopi C of the present invention.
Activity and the beneficial effect of compound Herba Lycopi C
This compound has certain repellent action to bollworm, beet armyworm, and peanut Cercospora bacteria, botrytis cinerea, sickle-like bacteria are had restraining effect, referring to table 2,3.And be basic framework with this new sesquiterpenoid, by the discussion of further structure activity relationship, reasonable process is designed and developed high reactivity, low toxicity sterilant, sterilant or the repellent that makes new advances.
The nematicide effect of table 2. compound Herba Lycopi C
| 20g ± line insect number (head) | Dead borer population (head) | Mortality ratio (%) | Average mortality (%) | |
| Compound Herba Lycopi C compound Herba Lycopi C | 42 75 | 37 57 | 80.95 76.00 | 78.84 |
Table 3. compound Herba Lycopi C is to the inhibition determination of activity of Pyricularia oryzae
| Herba Lycopi C (mg/l) | Pathogenic bacteria colony diameter (cm) | Inhibiting rate (%) | ||||||
| I | II | III | On | |||||
| 2 | 3.1 | 3.3 | 3.3 | 3.3 | 3.4 | 3.3 | 3.28 | 76.59 |
| 1 | 3.4 | 3.3 | 3.3 | 3.2 | 3.0 | 3.1 | 3.22 | 77.72 |
Description of drawings
Accompanying drawing 1: the X monocrystalline of Herba Lycopi C
Accompanying drawing 2: the intermolecular formation hydrogen bond of Herba Lycopi C
Claims (1)
1, a kind of have desinsection, an antimicrobial new compound, belongs to sesquiterpenoid, it is characterized in that the structural formula of this compound is:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101129167A CN100387567C (en) | 2005-10-14 | 2005-10-14 | New compound possessing insecticidal bactericidal activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101129167A CN100387567C (en) | 2005-10-14 | 2005-10-14 | New compound possessing insecticidal bactericidal activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1948256A true CN1948256A (en) | 2007-04-18 |
| CN100387567C CN100387567C (en) | 2008-05-14 |
Family
ID=38017899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005101129167A Expired - Fee Related CN100387567C (en) | 2005-10-14 | 2005-10-14 | New compound possessing insecticidal bactericidal activity |
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| Country | Link |
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| CN (1) | CN100387567C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101525508A (en) * | 2008-03-06 | 2009-09-09 | 中国农业科学院植物保护研究所 | Application of Eupatorium adenophorum extract as anti-fouling paint antifoulant |
| CN101933533A (en) * | 2010-07-20 | 2011-01-05 | 华南农业大学 | Plant source preservative and preparation method and application thereof |
| CN101658192B (en) * | 2009-09-23 | 2012-11-07 | 云南农业大学 | Application of eupatorium adenophorum vinegar liquid as plant nematocide |
| CN104782676A (en) * | 2015-03-19 | 2015-07-22 | 陕西乾龙高科生态农业有限公司 | Plant protective agent and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1287786A (en) * | 2000-10-08 | 2001-03-21 | 四川九章生物化工科技发展有限公司 | Method for preparing biological broad spectrum insecticide |
-
2005
- 2005-10-14 CN CNB2005101129167A patent/CN100387567C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101525508A (en) * | 2008-03-06 | 2009-09-09 | 中国农业科学院植物保护研究所 | Application of Eupatorium adenophorum extract as anti-fouling paint antifoulant |
| CN101525508B (en) * | 2008-03-06 | 2013-07-24 | 中国农业科学院植物保护研究所 | Application of Eupatorium adenophorum extract as anti-fouling paint antifoulant |
| CN101658192B (en) * | 2009-09-23 | 2012-11-07 | 云南农业大学 | Application of eupatorium adenophorum vinegar liquid as plant nematocide |
| CN101933533A (en) * | 2010-07-20 | 2011-01-05 | 华南农业大学 | Plant source preservative and preparation method and application thereof |
| CN101933533B (en) * | 2010-07-20 | 2013-06-05 | 华南农业大学 | Plant source preservative and preparation method and application thereof |
| CN104782676A (en) * | 2015-03-19 | 2015-07-22 | 陕西乾龙高科生态农业有限公司 | Plant protective agent and preparation method thereof |
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| Publication number | Publication date |
|---|---|
| CN100387567C (en) | 2008-05-14 |
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