Application of thiazole-ring-containing stilbene analogue as fungicide

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

Active Publication Date: 2019-11-12
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 thiazole-ring-containing stilbene analogue as fungicide
  • Application of thiazole-ring-containing stilbene analogue as fungicide
  • Application of thiazole-ring-containing stilbene analogue as fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0027]Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (2.5 g, 15 mmol) into a 100 mL three-necked flask, and heat to The reaction was carried out at 100°C, 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 5...

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, heat 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 ) 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)thiazole, the calculated yield is 47.3%. m.p.: 124~12...

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) into a 100 mL three-necked flask, and heat to The reaction was carried out at 130°C, 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 y...

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Abstract

The invention discloses application of a thiazole-ring-containing stilbene analogue as a fungicide. The structure of the stilbene analogue is shown as a formula (I). In the formula (I), H on a benzenering is monosubstituted, polysubstituted or unsubstituted by a substituent R; n is an integer of 0 to 2, and represents the number of the substituents R on the benzene ring; when the n is 0, H on thebenzene ring is not substituted; when the n is 1, the H on the benzene ring is monosubstituted by the substituent R; when the n is 2, H on the benzene ring are disubstituted by the substituent R, with the substituents R at different substation positions being same or different; the substituent R is hydrogen, C1-C4 alkyl, C1-C3 halogenated alkyl, alkoxy or halogen. The stilbene analogue has a particularly good inhibitory effect on fungi causing wheat scab and corn southern leaf blight.

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 Applications(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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