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Application of a stilbene-like compound containing a thiazole ring as a fungicide

A stilbene, thiazole ring-containing technology, applied in the directions of fungicides, applications, biocides, etc., can solve problems such as structure and biological activity studies that have not been reported in literature

Active Publication Date: 2020-12-15
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The series of stilbene-like compounds containing thiazole rings designed and synthesized by the present invention have no literature reports on their structures and biological activities.

Method used

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  • Application of a stilbene-like compound containing a thiazole ring as a fungicide
  • Application of a stilbene-like compound containing a thiazole ring as a fungicide
  • Application of a stilbene-like compound containing a thiazole ring as a fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of Derivative Ia (R(n)=H):

[0030] Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 15 mL (86.8 mmol) of triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was complete after about 1 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 20 mL of DMF, benzaldehyde (1.3 g, 12 mmol) and sodium hydroxide (0.9 g, 22 mmol) to the obtained concentrated solution to react. The reaction process was detected by TLC, and the reaction was completed in about 3 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid precipitated, filtered, and then recrystallized with ethyl acetate to obtain 1.6 g of a yellow solid, which was (E)-4 -(2,6-difluorophenyl)-2-styrylthiazole, the calculated yield is 54.7%. m.p.: 79~80℃;

[0031] 1 H NMR (500 MHz, Chloroform- d ) δ 7.56 (d, J = 7.5 Hz, 2H), 7.50 –7.37 (m, 5H), 7.37 – 7.26 (m, 2H), 7.02 (t,...

Embodiment 2

[0033] Example 2 Synthesis of derivative Ib (R(n)=o-chloro):

[0034] Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 9.0 mL (50.0 mmol) of triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was completed after about 1.5 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 25 mL of DMF, o-chlorobenzaldehyde (1.4 g, 10 mmol) and sodium hydroxide (1.3 g, 32 mmol) to the obtained concentrated solution for reaction. The reaction process was detected by TLC, and the reaction was completed in about 3.5 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid was precipitated, filtered, and then recrystallized with ethanol to obtain 1.4 g of a yellow solid, which was (E)-4-( 2,6-difluorophenyl)-2-o-chlorostyrylthiazole, the calculated yield is 40.6%. m.p.: 87~89℃;

[0035] 1 H NMR (500 MHz, Chloroform- d ) δ 7.83 (d, J = 16.0 Hz, 1H), 7.74 –7.67 (dd, ...

Embodiment 3

[0037] Example 3 Synthesis of derivative Ic (R(n)=p-chloro):

[0038] Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 12 mL (69.5 mmol) of triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was completed after about 3 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 22 mL of DMF, p-chlorobenzaldehyde (2.8 g, 20 mmol) and sodium hydroxide (2.0 g, 50 mmol) to the obtained concentrated solution to react. The reaction process was detected by TLC, and the reaction was completed in about 2.5 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid was precipitated, filtered, and then recrystallized with n-hexane to obtain 1.9 g of a yellow solid, namely (E)-4- (2,6-difluorophenyl)-2-p-chlorostyrylthiazole, the calculated yield is 56.1%. m.p.: 91~93℃;

[0039] 1 H NMR (500 MHz, Chloroform- d ) δ 7.50 – 7.45 (m, 3H), 7.40 (d, J =16.0 Hz, 1H), 7.38 –...

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Abstract

The invention discloses an application of a distyrene-like compound containing thiazole ring as a sterilizing agent. A synthesized compound is subjected to antifungal activity testing as fusahum graminearum, mycosphaerella melonis, botrytis cinerea and thanatephorus cucumeris, testing structures can prove that (E)-4-(2,6-difluorophenyl)-2-substituted styryl thiazole compounds have certain inhibition activity for test targets, the inhibition rates of compounds Ic, If and Ii for fusahum graminearum are 50% or above, and the inhibition rates of compounds Id and Ii for mycosphaerella melonis are 55% or above, wherein the inhibition rate of the compound Id for mycosphaerella melonis is 61.6%, which shows medium inhibition activity.

Description

technical field [0001] The present invention relates to the use of stilbene-like compounds containing thiazole rings as fungicides. Background technique [0002] As phytoalexins, stilbene compounds widely exist in nature, such as Polygonaceae plants Veratrum, Polygonum multiflorum, Polygonum cuspidatum, Liliaceae Smilax plants Smilax, Cassia, mulberry roots, etc. Stilbene compounds from natural sources have a variety of biological activities and have attracted widespread attention. They play a very important role in the field of new drug research and development. For example, in the field of medicine, it has anti-tumor (Bioorgan Med Chem, 2008, 16(7): 3800-3808), anti-oxidation (JBiol Chem, 2001, 276(25): 22586-22594), anti-inflammatory (J Agr Food Chem , 2017, 65(51): 11179-11191), anti-HIV (J Pharm Sci, 2004, 93(10): 2448-2457) and other activities; it has insecticidal properties in the field of pesticides (ChemPharmBull, 1992, 40(5): 1130-1136), antifungal (Med Chem Res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/78A01P3/00
CPCA01N43/78
Inventor 翁建全徐雯秀周智勇周亮刘幸海
Owner ZHEJIANG UNIV OF TECH
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