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Trichodermin derivant and uses thereof

A technology of trichoderma and derivatives, applied in the directions of biocides, chemicals for biological control, applications, etc., can solve the problems of no synthesis and application related reports, etc., and achieve the effect of good activity

Active Publication Date: 2009-05-13
ZHEJIANG DAYANG BIOTECH GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] According to the search of the applicant's information, the series of derivatives of the present invention are all synthetic new compounds, and there are no relevant reports on their synthesis and application

Method used

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  • Trichodermin derivant and uses thereof
  • Trichodermin derivant and uses thereof
  • Trichodermin derivant and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1, a kind of synthetic method of trichodermalin derivative a-1, its reaction formula is:

[0053]

[0054] Concrete reaction process is as follows:

[0055] Add 4.0g (16.0mmol) Trichoderma hydrolyzate (structural formula II), 6.0g (60.0mmol) triethylamine and 80mL dichloromethane in the reaction flask under ice-water bath, then add dropwise 3.6g (19.3mmol) dimethyl Chrysanthemum acid chloride, stirred at room temperature (0-30°C) for 0.5h.

[0056] The reaction solution was washed three times with 1% hydrochloric acid, and then washed with saturated NaHCO 3 The solution was washed twice, and finally washed twice with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain 6.5 g of solid product, which is recrystallized from ethanol and separated by filtration to obtain 5.8 g of product a-1, Y=90.6%. 1 H-NMR (500MHz, CDCl 3 , δppm): 5.596-5.573 (1H, m, -COOCH-), 5.411-5.398 (1H, m, -C=CH-), 4.898-4.877 (1H, m, Me 2 C=CH-), 3.830-3.819 (1H, m, -O-CH-C...

Embodiment 2

[0057] Embodiment 2, a kind of synthetic method of trichomycin derivative c-2, its reaction formula is:

[0058]

[0059] Add 4.0g (16.0mmol) Trichoderma hydrolyzate (structural formula is II), 6.0g (60.0mmol) triethylamine and 80mL dichloromethane in the reaction bottle under ice-water bath, add dropwise 3.28g (19.3mmol) 2- Bromopropionyl chloride, stirred and reacted at room temperature (0-30°C) for 0.5h.

[0060] The reaction solution was washed three times with 1% hydrochloric acid, and then washed with saturated NaHCO 3 The solution was washed twice, and finally washed twice with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain 6.13 g of solid product, which is recrystallized from ethanol and separated by filtration to obtain 5.25 g of product c-2, Y=85.5%. 1 H-NMR (500MHz, CDCl 3 , δppm): 5.589-5.563 (1H, m, -COOCH-), 5.412-5.403 (1H, d, -C=CH-), 4,442-4.393 (1H, m, Br-CH-), 3.853- 3.836 (1H, m, -O-CH-CH 2 -), 3.596-3.585 (1H, d, -C=C-CH-O-), 3.132-3.124...

Embodiment 3

[0061] Embodiment 3, a kind of synthetic method of Trichoderma derivative c-5, its reaction formula is:

[0062]

[0063] Add 4.0g (16.0mmol) Trichoderma hydrolyzate (structural formula is II), 6.0g (60.0mmol) triethylamine and 80mL dichloromethane in the reaction bottle under ice-water bath, then add dropwise 2.0g (19.3mmol) 3, 3-Dimethylbutyryl chloride, stirred and reacted at room temperature (0-30°C) for 6h.

[0064] The reaction solution was washed three times with 1% hydrochloric acid, and then washed with saturated NaHCO 3 The solution was washed twice, and finally washed twice with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain 5.67 g of solid product, which is recrystallized from ethanol and separated by filtration to obtain 4.86 g of product c-5, Y=95.05%. 1 H-NMR (500MHz, CDCl 3 , δppm): 7.036-6.963 (H, m, -CH=CH-CH 3 ), 5.903-5.862 (H, dd, -CH=CH-CH 3 ), 5.630-5.615 (1H, m, -COOCH-), 5.419-5.405 (1H, m, -C=CH-), 3.837-3.827 (1H, d, -O-CH-CH 2 -)...

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Abstract

The invention discloses a trichodermin derivative, and a structural general formula of the trichodermin derivative is shown as the right. The trichodermin derivative is used for killing plant pathogenic fungi such as Botrytis cinerea, Pythium ultinum Trow, fusarium, leafmold, Rhizoctonia solani, Fusarium oxysporum, Magnaporthe grisea and so on.

Description

technical field [0001] The invention belongs to the field of new pesticide creation, relates to a series of new trichoderma derivatives, and also relates to the inhibitory effect of the active components of the series of compounds on plant pathogenic fungi. Background technique [0002] According to the national "Eleventh Five-Year" development plan, pesticide innovation and creation is the key research content. At present, the discovery of new pesticides or lead substances is mainly based on analogous synthesis and natural active substance models. [0003] Biological pesticides are the category of natural active substances and an important way to create new pesticides. Because of its low toxicity to humans and animals, good environmental compatibility, and the resistance of harmful organisms, it meets the requirements of modern society for agricultural production and pesticides. This situation will also promote the rapid development of biological pesticides. [0004] Agri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A01N43/90A01P3/00
Inventor 程敬丽赵金浩周勇王国平章初龙林福呈朱国念
Owner ZHEJIANG DAYANG BIOTECH GROUP
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