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Trichodermin derivatives and application thereof in preventing and controlling pathogenic bacteria

A technology of trichoderma and phytopathogenic fungi, applied in the direction of chemicals, biocides, and applications for biological control, can solve the problems of chemical fungicide resistance environment, food cumulative pollution, etc., and achieve excellent results, active effect

Inactive Publication Date: 2010-07-28
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] The specific reaction process is as follows:

[0040] 4.0 g (13.7 mmol) of trichoderma (structural formula II), 2.0 g (18.0 mmol) of selenium dioxide and 80 mL of chloroform were added to the reaction flask, heated to reflux, and stirred for 0.5 h. The reaction solution was washed three times with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain 3.5g of solid product, which is separated by silica gel column chromatography (eluting solvent is ethyl acetate:petroleum ether=1:5, volume ratio) to obtain 0.8g of compound 1 and 2.1g of compound of formula III.

[0041] Structural data for 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, ...

Embodiment 2

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

[0045]

[0046] 1.0 g (3.2 mmol) of the compound of formula III obtained by the method in Example 1, 0.6 g (6.0 mmol) of triethylamine and 80 mL of dichloromethane were added to the reaction flask at room temperature (10-30 °C), and then 664 mg (4.0 mmol) of dichloromethane were added dropwise. mmol) phenylacryloyl chloride, and the reaction was stirred for 0.5 h. 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 1.38g of solid product, which is separated and purified by silica gel column (eluent is ethyl acetate:petroleum ether=1:10) to obtain 1.09g of compound 2.

[0047] Structural data for compound 2: 1 H-NMR (500MHz, CDCl 3 , δppm): 7.729-7.697 (1H, d, Ph-CH=CH-), 7.545-7.394...

Embodiment 3

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

[0049]

[0050] 1.0 g (3.2 mmol) of the compound of formula III obtained by the method in Example 1, 0.6 g (6.0 mmol) of triethylamine and 80 mL of dichloromethane were added to the reaction flask at room temperature (10 to 30 ° C), and 0.40 g ( 4.3 mmol) propionyl chloride, and the reaction was stirred for 0.5 h. 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 1.22g of solid product, which is separated and purified by silica gel column (eluent is ethyl acetate:petroleum ether=1:10) to obtain 0.96g of compound 4.

[0051] Structural data for 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 (1H, m, -COOC...

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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, relates to a series of novel trichoderma derivatives, and also relates to the inhibitory effect of active ingredients 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 improves the effect of fungicides in controlling plant diseases. However, some chemical fungicides have problems such as drug resistance and cumulative pollution to the environment and food. Therefore, the research and development of biological pesticides, especially the search and development of new fungicides from natural plant...

Claims

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Application Information

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Patent Type & Authority Applications(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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