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Application of a stilbene analog containing a thiazole ring structure as a fungicide

A technology containing thiazole rings and analogs, applied in the direction of fungicides, applications, biocides, etc., can solve the problems of structure and biological activity research that have not been reported in the literature, and achieve the effect of simple preparation and good antibacterial activity

Active Publication Date: 2022-02-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The series of stilbene analogs containing thiazole ring structure designed and synthesized by the present invention have no literature reports on their structure and biological activity research

Method used

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  • Application of a stilbene analog containing a thiazole ring structure as a fungicide
  • Application of a stilbene analog containing a thiazole ring structure as a fungicide
  • Application of a stilbene analog containing a thiazole ring structure as a fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of Compound Ia (R(n)=H):

[0027]In a 100mL three-necked flask, add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10mmol), triethyl phosphite (2.5g, 15mmol), heat to 100 The reaction was carried out at ℃, and the progress of the reaction was detected by TLC, and the reaction was completed after about 3 hours. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (2.9 g, 40 mmol), benzaldehyde (1.1 g, 10 mmol) and sodium hydroxide (0.4 g, 10 mmol) to the resulting concentrated solution React at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 4 hours. Then, the reaction solution was poured into ice water (120 mL), stirred, and a solid was precipitated, filtered, and the filter cake was recrystallized with ethyl acetate to obtain 1.9 g of a yellow solid, which was (E) -5-bromo-4-(4-fluorophenyl)-2-styrylthiazole, the calculated yield is 53.2%. m.p.:...

Embodiment 2

[0030] The synthesis of embodiment 2 compound Ib (R (n)=o-chloro):

[0031] Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (3.3 g, 20 mmol) into a 100 mL three-necked flask, and heat to The reaction was carried out at 120°C, and the progress of the reaction was detected by TLC, and the reaction was completed after about 1.5 h. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (4.0 g, 55 mmol), o-chlorobenzaldehyde (1.4 g, 10 mmol) and sodium hydroxide (1.3 g, 32 mmol) to the resulting concentrated solution ) react at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 4.5 hours. Then, the reaction solution was poured into ice water (130 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with n-hexane to obtain 1.86 g of a yellow solid, which was (E) -2-(2-chlorostyryl)-5-bromo-4-(4-fluorophenyl)thiazol...

Embodiment 3

[0034] Example 3 Synthesis of Compound Ic (R(n)=p-chloro):

[0035] Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (2.8 g, 17 mmol) in a 100 mL three-necked flask, heat to 130 The reaction was carried out at ℃, and the progress of the reaction was detected by TLC, and the reaction was completed after about 1 h. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (3.7g, 50mmol), p-chlorobenzaldehyde (1.7g, 12 mmol) and sodium hydroxide (0.9 g, 22 mmol) to the resulting concentrated solution ) react at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 4 hours. Then, the reaction solution was poured into ice water (185 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with n-hexane to obtain 2.4 g of a yellow solid, namely (E)- 2-(4-chlorostyryl)-5-bromo-4-(4-fluorophenyl)thiazole, the calculated yield w...

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Abstract

The invention discloses the application of a Stilbene analog containing a thiazole ring structure as a fungicide. The structural formula of the Stilbene analog containing a thiazole ring structure is shown in formula (I): in formula (I), the H on the benzene ring is The substituent R is mono-substituted, di-substituted or unsubstituted; n is an integer from 0 to 2, and n represents the number of substituent R on the benzene ring; when n=0, it means that the H on the benzene ring is not substituted; n= When 1, it means that the H on the benzene ring is monosubstituted by the substituent R; when n=2, it means that the H on the benzene ring is disubstituted by the substituent R, and the substituents R on different substitution positions are the same or different; the substituents R is hydrogen, C1~C4 alkyl, C1~C3 haloalkyl, methoxy or halogen. The Stilbene analog containing the thiazole ring structure of the present invention has a good inhibitory effect on wheat head blight and maize spot fungus.

Description

technical field [0001] The invention relates to the application of a Stilbene analogue containing a thiazole ring structure as a fungicide. Background technique [0002] Stilbene compounds are a general term for a class of compounds with stilbene as the structural core. They exist widely in nature as phytoalexins, such as Maimaiteng, Liliaceae veratrum, Liaceae Polygonum cuspidatum, Polygonum multiflorum, and Mulberry Mulberries, Grapes, etc. Stilbene compounds have good properties such as antibacterial and anti-inflammatory (J. Agric. Food Chem, 2017, 65(51): 11179-11191), antioxidant (Chem. Pharm. bull, 1987, 35(2): 887-890. ), anti-cancer (Mol. Nutr. & Food Res, 2005, 49(5): 452-461.), anti-tumor (Anticancer Res, 2004, 24(5A): 2783-2840.) and other pharmaceutical and physiological activities, Therefore, it has received extensive attention in the field of medical and health products. Compared with its medicinal activity, its pesticide activity has received less attentio...

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 翁建全叶飞霞朱亚波刘幸海
Owner ZHEJIANG UNIV OF TECH
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