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Trichodermin derivatives and application thereof in preventing and controlling pathogenic bacteria

A technology of trichoderma and phytopathogenic fungi, which is applied in the directions of chemicals, biocides, and applications for biological control, can solve the problems of chemical fungicides-resistant environment, food accumulation pollution, etc., and achieves excellent results, active effect

Inactive Publication Date: 2012-02-29
ZHEJIANG DAYANG BIOTECH GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some chemical fungicides have problems such as drug resistance, cumulative pollution to the environment and food, so the development and research of biological source pesticides, especially finding and developing new fungicides from natural plants, animals and microorganisms is a current research hotspot

Method used

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  • Trichodermin derivatives and application thereof in preventing and controlling pathogenic bacteria
  • Trichodermin derivatives and application thereof in preventing and controlling pathogenic bacteria
  • Trichodermin derivatives and application thereof in preventing and controlling pathogenic bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, a kind of synthetic method of trichoderma derivatives (compound 1), its reaction formula is:

[0038]

[0039] Concrete reaction process is as follows:

[0040] Add 4.0g (13.7mmol) trichodermain (structural formula II), 2.0g (18.0mmol) selenium dioxide and 80mL chloroform into the reaction flask, heat to reflux, and stir for 0.5h to react. The reaction solution was washed three times with water, anhydrous Na 2 SO 4 It was dried and concentrated to obtain 3.5 g of solid product, which was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:5, volume ratio) to obtain 0.8 g of compound 1 and 2.1 g of compound of formula III.

[0041] Structural data of compound 1: 1 H-NMR (500MHz, CDCl 3 , δppm): 9.537 (1H, s, -CHO), 6.612-6.598 (1H, m, -C=CH-), 5.611-5.588 (1H, d, -COOCH-), 3.891-3.880 (2H, m, -O-CH-CH 2 -&-C=C-CH-O-), 3.126-3.118 (1H, d, -O-CH 2 ), 2.857-2.849 (1H, d, -O-CH 2 ), 2.600-2.554 (1H, m, -COOCH-CH 2 ...

Embodiment 2

[0044] Embodiment 2, a kind of synthetic method of trichomycin derivative (compound 2), its reaction formula is:

[0045]

[0046] At room temperature (10~30 ℃), add 1.0g (3.2mmol) compound of formula III, 0.6g (6.0mmol) triethylamine and 80mL dichloromethane that embodiment 1 method gained in reaction bottle, dropwise add 664mg (4.0mL) mmol) phenylacryloyl chloride, stirred and reacted for 0.5h. 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 It was dried and concentrated to obtain 1.38 g of solid product, which was separated and purified by silica gel column (eluent: ethyl acetate:petroleum ether=1:10) to obtain 1.09 g of compound 2.

[0047] Structural data of compound 2: 1 H-NMR (500MHz, CDCl 3 , δppm): 7.729-7.697 (1H, d, Ph-CH=CH-), 7.545-7.394 (5H, m, Ph-H 5 ), 6.458-6.426 (1H, d, Ph-CH=CH-), 5.615-5.604 (1H, m, ...

Embodiment 3

[0048] Embodiment 3, a kind of synthetic method of trichomycin derivative (compound 4), its reaction formula is:

[0049]

[0050] Add 1.0g (3.2mmol) of the compound of formula III, 0.6g (6.0mmol) of triethylamine and 80mL of methylene chloride obtained in the method of Example 1 into the reaction flask at room temperature (10-30°C), and then add dropwise 0.40g ( 4.3mmol) propionyl chloride, stirred and reacted for 0.5h. 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 It was dried and concentrated to obtain 1.22 g of solid product, which was separated and purified through a silica gel column (eluent: ethyl acetate:petroleum ether=1:10) to obtain 0.96 g of compound 4.

[0051] Structural data of compound 4:

[0052] 1 H-NMR (500MHz, CDCl 3 , δppm): 5.571-5.554 (1H, m, -COOCH-), 5.538-5.515 (1H, m, -C=CH-), 5.378-5.345 (1...

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PUM

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Abstract

The invention discloses trichodermin derivatives, which have a structural general formula, wherein in the formula, R1 is -Me, and R2 is R3COO-; or R1 is -CHO, and R2 is H or R3COO-. The invention also discloses application of the trichodermin derivatives in killing plant pathogenic fungi which comprise sclerotinia scleotiorum, rice blast, rice false smut, rice sheath blight and the like.

Description

technical field [0001] The invention belongs to the field of new pesticide creation, and relates to a series of novel trichoderma derivatives, and also relates to the inhibitory effect of the active components of the series of compounds on plant pathogenic bacteria. Background technique [0002] Plant diseases cause huge losses to crop yields every year. Although there are various methods and measures to control plant diseases, fungicides still play an important role in the integrated control of plant diseases. Many chemical fungicides commonly used at present have the characteristics of broad spectrum, high efficiency and low toxicity, which significantly improve the effect of fungicides on controlling plant diseases. However, some chemical fungicides have problems such as drug resistance, cumulative pollution to the environment and food, so the development and research of biological source pesticides, especially finding and developing new fungicides from natural plants, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10A01N43/90A01N47/20A01N53/04A01P3/00
Inventor 赵金浩程敬丽周勇徐旭辉王国平章初龙林福呈朱国念
Owner ZHEJIANG DAYANG BIOTECH GROUP
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