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Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof

A dihydro-agarwood and furan-type technology, applied in the field of preparation of antibacterial and insecticidal pesticides, can solve the problems of activity differences, no research reports on insecticidal and antibacterial activities, and non-existence

Active Publication Date: 2015-10-21
INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But the sesquiterpene compounds in the above plants do not contain 5-carboxy-N-methyl-2-pyridone (CNMP) group
The anesthetic and poisonous effects of dihydroagarfuran-type sesquiterpenes on pests are related to the position and type of substituents, and different substituents will cause significant activity differences[8]
The dihydroagarfuran-type sesquiterpenes linked to the CNMP group were only found in 5 plant species, namely maytansine Emarginatine A-H in Maytenus emarginata ( Maytenus emarginata ), China Emarginatinine from Maytenus emarginata (Willd.) D. Hou), Hippocrateine ​​I-III from Loeseneriella merrilliana , tall wings Compounds 1-5, 7-19 in vine (Hippocratea excelsa), and Reissantins A-C, F-H in plant (Reissantia buchananii), but none of them have been reported to kill Insect antibacterial activity[9]

Method used

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  • Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof
  • Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof
  • Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 5 kg of stems and leaves of the vine sesquiterpene were extracted with 90% ethanol at 60°C for 3 times, filtered and concentrated to obtain the extract, which was suspended in water and then extracted with ethyl acetate to obtain the ethyl acetate fraction. The ethyl acetate extract was chromatographed on D101 macroporous resin, and 50-80% alcohol eluted parts were collected, and then washed with C 18 Reverse-phase silica gel column, collect 70% of the elution fraction, and then use C 18 Prepare the liquid phase with a reversed-phase silica gel column, and collect 75% of the elution site to obtain compound 1 β -Acetyl-6 α -(5-carboxy-N-methyl-2-pyridinone)-8 β -Nicotinyl-9 α -Benzoyl- β - Dihydroagarfuran, the purity of which is greater than 98% as detected by HPLC-MS.

[0028] The structure of the compound can be resolved by combining the MS / MS data with the NMR spectrum. HR-ESI MS m / z673.2699[M+H] + , showing the molecular formula as C 37 h 40 N 2 o 10 , wi...

Embodiment 2

[0031] The preliminary toxicity determination of insecticides adopts the spray method.

[0032] (1) Preparation of medicines: The ethyl acetate part of the vine petals and the new sesquiterpene were prepared into an acetone solution of 1 mg / mL, then diluted 10 times with acetone, and set aside.

[0033] (2), test insect removal: take diamondback moth ( Plutella xylostella ) After the 3rd instar larvae were concentrated and mixed, they were brushed into the petri dish with a brush, and 10 larvae were treated each time, and repeated. Each treatment requires 15-30 test insects, and a blank control is required for each test. The temperature is generally 20-28°C, the relative humidity is 60-80%, and the ventilation is good.

[0034] (3) Spraying quality inspection: Use a 9cm white circular paper to check whether the size of the spray droplets and the spraying are uniform. If they do not meet the requirements, adjust the nozzle and position to make the spraying quality meet the ...

Embodiment 3

[0040] The contact activity of insecticides was determined by the drop method.

[0041] (1) Drug preparation: According to the preliminary toxicity test results, dilute the acetone mother liquor of 1mg / mL new sesquiterpene with acetone to 5 concentrations, each concentration is 5mL, and put it into a stoppered small test tube. And acetone was used as a control.

[0042] (2), Indoor tested pests: diamondback moth ( Plutella xylostella ),cabbage caterpillar( Pieris rapae L.), corn armyworm ( Mythimna separate a Walker), Spodoptera litura ( Prodenia litura F.), silver-leaved moth ( Plusia agnata Staudinger ), pea aphids ( Pea aphids ), rice stem borer ( Chilo suppressalis Walker), rice stem borer ( Tryporyza incertulas Walker), twenty-eight star ladybug ( Henosepilachna vigintioctopunctata ), the 3rd instar larvae with basically the same individual size were selected for the test.

[0043] (3) Spot treatment method: Pick neat 3rd instar larvae and put them...

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PUM

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Abstract

The invention discloses a dihydroagarofuran type sesquiterpene compound, the preparing method of the compound, and the application of the compound in preparing anti-microbial pesticides and relates to the field of medicinal chemistry. According to the application of the novel sesquiterpene compound in anti-microbial pesticides, the structure of the adopted sesquiterpene compound is shown in the figure of the abstract and is named 1beta-acetyl-6alpha-(5-carboxyl-N-methyl-2-pyridone)-8beta-nicotinoyl-9alpha-benzoyl-beta-dihydroagarofuran. The compound is characterized in that the stem leaves of the plant Monimopetalum Chinese Rehd. are used as raw materials, and then the compound is obtained through extraction and separation with the natural product chemistry method. As a pesticide, the compound has a remarkable resisting effect on pests including plutella xylostella, cabbage caterpillar, corn armyworm, prodenia litura, argyrogramma agnate, pea aphids, rice-stem borer, rice tryporyza incertulas and henosepilachna vigintioctomaculata. As a sterilant, the compound has a remarkable resisting effect on sclerotinia sclerotioru, rhizoctonia cereal, fusarium graminearum and botrytis cinerea person.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and discloses a new sesquiterpene compound, its preparation method and its application in the preparation of antibacterial, insecticidal and pesticides. Background technique [0002] China is a large agricultural country, with about 400 million hectares of crop diseases, insect pests and weeds occurring all year round, and 800,000 tons of pesticides are required to be produced and used every year. Pesticides have become an indispensable factor in agricultural production. Although the extensive use of pesticides has played an important role in the development of production, problems such as insect pests, disease resistance, environmental pollution, residues and accumulation in agricultural and livestock products, and damage to natural enemies have also emerged. phasing out and banning highly toxic pesticides are practical and effective management measures based on my country's national conditions...

Claims

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Application Information

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IPC IPC(8): C07D405/14A01N43/40A01P7/04A01P3/00
CPCA01N43/40C07D405/14
Inventor 印敏冯煦单宇管福琴王奇志陈雨赵友谊王鸣宋萍萍
Owner INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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