CN106135205B - A kind of purposes of isoflavan class natural products DTMI - Google Patents

A kind of purposes of isoflavan class natural products DTMI Download PDF

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Publication number
CN106135205B
CN106135205B CN201610348621.8A CN201610348621A CN106135205B CN 106135205 B CN106135205 B CN 106135205B CN 201610348621 A CN201610348621 A CN 201610348621A CN 106135205 B CN106135205 B CN 106135205B
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dtmi
purposes
pesticide
natural products
wheat
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CN106135205A (en
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高坤
李广达
李亚
朱绪新
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Lanzhou University
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Lanzhou University
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses the purposes of isoflavan class natural products DTMI a kind of, DTMI is applied to prepare the purposes of novel plant source pesticide.The present invention provides possibility for the application of DTMI, provides new approach for the exploitation of new pesticide.

Description

A kind of purposes of isoflavan class natural products DTMI
Technical field
The present invention relates to a kind of purposes of isoflavan class natural products, in particular to a kind of isoflavan class natural products DTMI Purposes.
Background technique
For a long time, chemical pesticide is crops are antibacterial, play an important role in terms of sterilization, but is easy to produce anti- Pharmacological property causes natural ecosystems worsening, and as masses are to the pay attention to day by day of health and environmental problem, chemical pesticide is because of it The problems such as residual, environmental pollution, is queried by people.The food of people's health is especially directly affected, countries in the world are carried out " Green Trade Barrier ", limits the residual quantity of chemical pesticide.Therefore, seek to substitute chemical pesticide progress plant guarantor The advanced subject at our times various countries researcher is protected.Studying more successful substitute is biological pesticide, plant source Pesticide is the critically important research direction of biological pesticide.
Both at home and abroad to the main purpose of botanical pesticide research, first is that by screening to pesticide activity component in plant and Structural Identification, synthesizing botanical pesticide active constituent as commercially available agricultural chemical, or with the active constituent using organic synthesis means is Lead compound, by reasonable structure of modification, the new commercially available agricultural chemical of analog synthesis.Second is that passing through pesticidal active substance in plant Extracting and developing and screening, direct appliable plant development of resources plant source novel pesticide.External agricultural chemicals enterprise is with the former mostly It is main, because such approach must be premised on powerful manpower, fund, technology and good study condition, and research cycle It is too long；And China is then abundant because of plant resources, the period of botanical pesticide research and development is shorter, and cost is also relatively smaller, technology The reasons such as level requirement is low, mostly based on the latter.
Stripe rust of wheat is one of wheat rust.Wheat rust is commonly called as " jaundice ", slitting rust, stem rust, leaf rust 3 Kind, it is that distribution is wide in Wheat in China production, it is fast to propagate, the big important disease of hazard area.Wherein occurred most with stripe rust of wheat It is universal and serious.Occur mainly in Hebei, Henan, Shaanxi, Shandong, Shanxi, Gansu, Sichuan, Hubei, Yunnan, Qinghai, Xinjiang Etc. ground.Stripe rust of wheat is routinely using commercial fungicide triadimefon.However, due to using triadimefon for years (Triadimefon) etc. triazole bactericidal agents, the drug resistance that crop disease fungal pathogens generate it just enhance year by year, largely On affect the validity of chemical prevention.
Isoflavan class natural products 7,5'- dihydroxy -2', 3', 4'- trimethoxy isoflavan (7,5'-dihydroxy- 2',3',4'-trimethoxyisoflavan；It DTMI is) from high-quality legume forage alfalfa (name: Medicago earliest Sativa L., English name alfalfa) in it is isolated, referring to document: Phytochemistry, 1991,30 (12), 4147- 4149.But so far there are no any report inhibited to crop disease fungal pathogens in relation to DTMI, also have without any Close the report in terms of the other bioactivity of DTMI.
Summary of the invention
The purpose of the present invention is to provide the new applications of isoflavan class natural products DTMI a kind of, provide for the application of DTMI Possibility, for the exploitation of new pesticide provides new approach.
The technical solution adopted by the present invention to solve the technical problems is:
A kind of purposes of isoflavan class natural products DTMI, DTMI are applied to prepare the purposes of novel plant source pesticide.
The chemical structure of DTMI is as follows:
Preferably, DTMI is applied to the purposes that preparation inhibits the novel plant source pesticide of wheat fungal diseases.As excellent Choosing, the wheat fungal diseases are the true of puccinia striiformis (Puccinia striiformis.f.sp.tritici) initiation Fungus diseases.
The prior art there is not yet DTMI any active report, the present invention provides prepare plant source agriculture with DTMI Medicine, to inhibit the method for crop disease fungal pathogens.Inventors be surprised to learn that DTMI is directed to stripe rust of wheat (Stripe rust) Disease fungus have preferable bacteriostasis, develop its new application as pesticide, provided for the exploitation of new pesticide New approach.
The beneficial effects of the present invention are: the application for DTMI provides possibility, provided newly for the exploitation of new pesticide Approach.
Specific embodiment
Below by specific embodiment, technical scheme of the present invention will be further explained in detail.
In the present invention, if not refering in particular to, used raw material and equipment etc. are commercially available or commonly used in the art. Method in following embodiments is unless otherwise instructed the conventional method of this field.
Embodiment:
DTMI pure strain used in the present invention is extracted from the alfalfa for having infected rust (Uromyces striatus) , extraction process is as follows:
After being crushed from the alfalfa aerial part 6kg for the rubiginose that Gansu Province Qingyang City acquires, with 95% ethyl alcohol Soak extraction 3 times at room temperature 7 days every time, are concentrated under reduced pressure to give total medicinal extract 264g, soluble in water, are then extracted with ethyl acetate. Ethyl acetate portion is concentrated under reduced pressure to give 117.6g medicinal extract；Medicinal extract uses macroporous resin column chromatography depigmentation after being dissolved with ethyl alcohol, pure After water balance, ethanol/water system 30%, 50%, 80% is successively eluted, and three parts are obtained；80% part (12.4g) adds It is segmented after methanol dissolution with MCI column chromatography, methanol/water system 10%-90% is successively eluted, and Fr.1-Fr.9 nine is obtained Part；Fr.6 (1.552g) is solidifying through silica gel column chromatography (petroleum ether/acetone 10:1,5:1,2:1,1:1 is successively eluted) and glucan Plastic column chromatography (Sephadex LH-20；The elution of pure methanol) purifying obtains the compound (27.3mg), and confirming through Structural Identification should Compound is DTMI, and Structural Identification is as follows:
White amorphous powder, mass spectrum (ESI-MS) provide its molecular ion peak [M+H]+M/z=333, in conjunction with13C NMR And DEPT, it may be determined that the molecular formula of the compound is C18H20O6, degree of unsaturation 9.The compound1H NMR shows different Huang 5 diagnostic protons signal δ of alkyl compoundH2.89 (2H, m), 3.57 (1H, m), 3.99 (1H, dd, J=10.0, 10.8Hz), 4.28 (1H, dd, 10.4,3.2,2.4Hz) and 1 ABX spin coupling system δH6.37 (1H, d, J= 2.4Hz), 6.41 (1H, dd, J=8.0,2.4Hz), 6.95 (1H, d, J=8.0Hz), 1 unimodal proton signal δH6.47(1H, S), 3 methoxyl group signal δH3.82 (3H, s), 3.94 (3H, s), 3.95 (3H, s) and the active hydrogen signal δ of 2 hydroxylsH4.85 (1H, s), 5.53 (1H, s), thus it is speculated that the compound is an isoflavan class compound, and there are 2 hydroxyls and 3 methoxies in molecule Base, thereby increases and it is possible to be replaced in 7,2', 3', 4', 5'；133 features of the C NMR in addition to showing isoflavan class compound Carbon signal δCOutside, there are also 12 aryl carbon signals and 3 methoxyl group carbon letters by 70.33 (C-2), 31.73 (C-3), 31.39 (C-4) Number, further demonstrate supposition in front；By consulting literatures, the spectral data and 7 of the compound, 5'- dihydroxy-are found The wave spectrum number of 2', 3', 4'- trimethoxy isoflavan (7,5'-dihydroxy-2', 3', 4'-trimethoxyisoflavan) According to completely the same.So far, the structure of product determined (white amorphous powder,1H NMR and131) C NMR data is shown in Table.
1. compound DTMI's of table1H NMR and13C NMR data (400MHz, CDCl3)
Measurement of the compound DTMI to phytopathogen inhibitory activity:
1. test plant pathogen: puccinia striiformis (Puccinia striiformis.f.sp.tritici)；Potting Testing wheat breed is inscription virtuous 169.
2. test method: compound DTMI tests the living body measurement of phytopathogen inhibiting effect using greenhouse pot culture Method, bibliography: fourth cloth is to the Chinese agronomy notification of the inhibiting effect [J] of puccinia striiformis, 2006,22 (6), 324-326.
15 plants or so will be planted for potting after the disinfection of examination wheat seed, seed soaking, vernalization, every basin；DTMI is matched with sterile water It is 0.5mg/ml (adding 0.1%Tween20) that concentration, which is made,；Clear water and triadimefon processing are set simultaneously (adds 0.1% as control Tween20), each processing is repeated 3 times.
When first leaf of wheat seedling is fully deployed, resistant determination experiment is carried out.When protective effect measures, spray-on process is used After application for 24 hours, then with connection is swept connect bacterium moisturizing for 24 hours, be then transferred to Routine Management, to clear water control sufficiently after the onset of, carry out disease Sentiment is looked into；Therapeutic effect method for measuring and protective effect are essentially identical, and therapeutic effect first connects bacterium when measuring, after moisturizing for 24 hours again Application.
Stripe rust of wheat Seriousness gradation standard: 0 grade=wheat leaf blade is not fallen ill；1 grade=1%~5%；3 grades=6%~ 25%；5 grades=26%~50%；7 grades=51%~75%；9 grades=75% or more.
Bibliography: China State Bureau of Quality and Technical Supervision's national standard: pesticide field efficacy medicine test criterion
(1) Beijing [M]: China Standards Press, 2000:437-440.
3. test result: in Seedling Stage, compound DTMI the results are shown in Table 2 to the preventive effect of stripe rust of wheat, and blank control is Clear water, positive control are triadimefon.
2. compound DTMI of table is in Seedling Stage to the prevention and treatment result of stripe rust of wheat
Indoor pot the experimental results showed that, under 0.5mg/ml concentration, compound DTMI has Seedling Stage stripe rust of wheat Apparent protection and therapeutic effect, and protective effect is greater than therapeutic effect, but control efficiency is not as good as commercial fungicide triadimefon.So And due to using triazole bactericidal agents, crop disease fungal pathogens such as triadimefon (Triadimefon) to generate it for years Drug resistance just enhances year by year, largely affects the validity of chemical prevention.In this context, DTMI etc. has Thinking can be provided for the exploitation of novel plant source bactericide by having the isoflavan class compound of certain fungistatic effect.
Above-mentioned embodiment is only a preferred solution of the present invention, not the present invention is made in any form Limitation, there are also other variations and modifications on the premise of not exceeding the technical scheme recorded in the claims.

Claims (1)

1. a kind of purposes of isoflavan class natural products DTMI, it is characterised in that: DTMI is applied to preparation and inhibits wheat fungal The purposes of harmful botanical pesticide；The wheat fungal diseases are the fungal disease that puccinia striiformis causes.
CN201610348621.8A 2016-05-23 2016-05-23 A kind of purposes of isoflavan class natural products DTMI Active CN106135205B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5063244A (en) * 1990-07-30 1991-11-05 Development Center For Biotechnology Process for the isolation of antifungal agents (5-methoxy-7-hydroxyflavan) from dragon's blood resin and its use in agriculture
CN102357092A (en) * 2011-09-01 2012-02-22 兰州大学 Use of flavanone natural product 7,3'-dyhydroxy-2',4'-dimethoxy-isoflavane (DDIF)
CN102726195A (en) * 2012-07-11 2012-10-17 福建省农业科学院畜牧兽医研究所 Method for inhibiting grass by means of allelopathic effect of alfalfa leaves

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5063244A (en) * 1990-07-30 1991-11-05 Development Center For Biotechnology Process for the isolation of antifungal agents (5-methoxy-7-hydroxyflavan) from dragon's blood resin and its use in agriculture
CN102357092A (en) * 2011-09-01 2012-02-22 兰州大学 Use of flavanone natural product 7,3'-dyhydroxy-2',4'-dimethoxy-isoflavane (DDIF)
CN102726195A (en) * 2012-07-11 2012-10-17 福建省农业科学院畜牧兽医研究所 Method for inhibiting grass by means of allelopathic effect of alfalfa leaves

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