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1,2,3-thiadiazole-containing benzoyl hydrazone derivative as well as preparation method and application thereof

A technology for benzoylhydrazone derivatives, applied in the field of organic chemical synthesis, can solve the problems of rare research literature on benzoylhydrazone derivatives, and achieve the effects of high inhibitory activity, low cost and high yield

Inactive Publication Date: 2016-03-30
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many research literatures on acylhydrazone derivatives containing thiadiazole rings

Method used

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  • 1,2,3-thiadiazole-containing benzoyl hydrazone derivative as well as preparation method and application thereof
  • 1,2,3-thiadiazole-containing benzoyl hydrazone derivative as well as preparation method and application thereof
  • 1,2,3-thiadiazole-containing benzoyl hydrazone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation and structure identification of 4-butyl-1,2,3-thiadiazole-5-methanol (V-05)

[0037] Weigh 8.56g (0.04mol) of ethyl 4-butyl-1,2,3-thiadiazole-5-carboxylate into a 100ml three-neck flask, add 30mL of ethanol to dissolve, then place in an ice-salt bath and cool to 0°C Next, slowly add 2.28g (0.06mol) sodium borohydride, remove the ice-salt bath and heat up to 25°C, react at room temperature for 5 hours, add dilute hydrochloric acid to the reaction system until the solution is acidic, extract with dichloromethane, and use Wash with saturated sodium bicarbonate solution and saturated sodium chloride solution, dry the organic phase with anhydrous sodium sulfate, filter with suction, and concentrate the filtrate to obtain 6.31 g of yellow liquid, which is the intermediate V-05 of the present invention, with a yield of 91.7%.

[0038] V-01~V-04 were successfully prepared according to the same method as that used to prepare compound V-05. The physical and...

Embodiment 2

[0039]Example 2: Preparation and structure identification of intermediate 4-butyl-1,2,3-thiadiazole-5-carbaldehyde (II-05)

[0040] Weigh 10.63g (0.05mol) of PCC into a 100ml three-neck flask, add 40ml of dichloromethane and stir to dissolve, then slowly add 6.02g (0.035mol) of 4-butyl-1,2,3-thiadiazole-5-methanol The dichloromethane solution was monitored by TLC until the reaction was complete. Stop the reaction, filter with suction, wash the filtrate with saturated sodium bicarbonate solution and saturated sodium chloride solution respectively, dry the organic phase with anhydrous sodium sulfate, filter with suction, and concentrate the filtrate to obtain 5.39 g of yellow liquid, which is intermediate II of the present invention -05, yield 90.6%.

[0041] According to the same method as the preparation of compound II-05, II-01~II-04 were successfully prepared, and their physical and chemical data and structural identification data are shown in Table 1. From the relevant dat...

Embodiment 3

[0046] Example 3: Preparation and structure identification of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde-2-bromo-benzoylhydrazone (No. I-01)

[0047] Add 20mL of methanol and 0.32g (2.5mmol) of the compound 4-methyl-1,2,3-thiadiazole-5-carbaldehyde shown in formula II to a 50mL three-necked flask, stir, and add 0.6mg (0.01mmol) in one go Acetic acid is activated, and then the compound shown in 0.43g (2mmol) formula III (R 2 2-substituted bromo) 2-bromo-benzohydrazide was dissolved in methanol, slowly added to the above-mentioned three-necked flask, heated to 78°C and refluxed for 6 hours to stop the reaction. The solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized from ethanol to obtain 0.56 g of a white solid with a yield of 87%. The appearance and fusing point of this white solid product are shown in Table 2, and its 1 HNMR spectrum data are shown in Table 3. It can be seen from Table 3 that the product has a correct structure and ...

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Abstract

The invention belongs to the field of organic compound synthesis and particularly relates to a 1,2,3-thiadiazole-containing benzoyl hydrazone derivative as well as a preparation method and application thereof. The structure of the compound is shown by a formula I in the specification. In the invention, the synthesis method of the compound shown by the formula I is easy to operate, the raw materials are easily available, the production of toxic by-products is avoided, and the yield is relatively high. According to biological activity tests, the compound shown by the formula I shows excellent bactericidal activity, can be used for preventing controlling apple rot, rice sheath blight, pythium aphanidermatum, botrytis cinerea, alternaria solani and bakanae disease in agricultural production and has relatively good value in application and development.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a benzoylhydrazone derivative containing 1,2,3-thiadiazole, a preparation method thereof, and an application of the compound in sterilization. Background technique [0002] Heterocyclic compounds have become the mainstream field of research and development of new pesticides, and nitrogen-containing heterocycles are the focus of research. According to statistics, about 70% of ultra-efficient pesticides are nitrogen-containing heterocycles (Chen, Q. et. al. Eur. J. Med. Chem. 2008, 43, 595.). Among them, 1,2,3-thiadiazole has a unique structure, good environmental compatibility and a wide range of biological activities, and is more and more favored by researchers, and reports on its biological activities are increasing day by day. 1,2,3-Thiadiazole derivatives have bactericidal, herbicidal, insecticidal, anti-cancer, and disease-resistant activities (Zuo, X.et...

Claims

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Application Information

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IPC IPC(8): C07D285/06A01N43/828A01P3/00
CPCA01N43/82C07D285/06
Inventor 杨新玲张景朋凌云秦耀果段红霞杜少卿李文浩
Owner CHINA AGRI UNIV
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