S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof

A technology for furanthiocarboxylic acid and ester compounds, which is applied in the field of synthesis of heterocyclic compounds, and achieves the effects of high yield, expanded application prospects, and novel structures

Active Publication Date: 2016-10-12
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The 1,3,4-thiadiazole fungicides such as Dicumazole and Bis-ADTA used to be effective agents for the control of rice bacterial blight, a refractory disease of rice, but due to the serious teratogenic effect and the growing problem of drug resistance

Method used

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  • S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof
  • S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof
  • S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof

Examples

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Embodiment 1

[0053] Example 1: S-1,3,4-thiadiazole-5-(4-chlorophenyl)-2-furan thiocarbamate (I-1-1) and S-(5-methyl- Preparation of 1,3,4-thiadiazole)-5-(4-chlorophenyl)-2-furan thiocarbamate (I-1-2)

[0054]

[0055] Add 15mmol 1,3,4-thiadiazole-2-thiol (or 5-methyl-1,3,4-thiadiazole-2-thiol) and 10ml di Chloromethane, add 10% (wt.) sodium hydroxide aqueous solution containing 15 mmol sodium hydroxide at room temperature, control the rate of addition, and keep the temperature at room temperature. After this was completed, a dichloromethane solution containing 7.5 mmol of 5-(4-chlorophenyl)-2-furoyl chloride was added dropwise. Control the rate of addition so that both are added at the same time. After the dropwise addition, slowly raise the temperature to 50°C, and react at 50°C for 3-10 hours. After the reaction was completed, filter to remove the precipitate, and rotate the filtrate to remove the solvent to obtain a light yellow solid. Use a silica gel column (eluent: V petroleum...

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Abstract

The invention discloses an S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, a preparation method and application thereof. The compound has a structural general formula shown as formula I. The S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound has an obvious control effect on potato late blight, cucumber fusarium wilt, Botrytis cinerea Pers, Pepper Phytophthora blight, rice sheath blight, wheat scab, Colletotrichum musae, asparagus stem blight and the like, and can be used as an agricultural fungicide in control of plant diseases. At the same time, the compound has an inhibitory effect on HL-60 human leukemia cells, MCF-7 human breast cancer cells, BGC-823 human gastric cancer cells, Bel-7402 human hepatocellular carcinoma cells, and KB human nasopharyngeal carcinoma cells, etc., and has application prospects in the aspect of anti-tumor activity. (formula I).

Description

technical field [0001] The invention belongs to the field of synthesis of heterocyclic compounds, in particular to S-(5-substituted-1,3,4-thiadiazole)-(5-substituted phenyl)-2-furan thiocarboxylate compounds and preparation methods thereof and apply. Background technique [0002] In recent years, with the research of heterocyclic compounds with biological activity and novel structure, more and more researchers have devoted themselves to the design and synthesis of various heterocyclic compounds. Among them, people have more and more researches on 1,3,4-thiadiazoles, and many 1,3,4-thiadiazoles have been commercialized and put into use in pesticides. [0003] (1) Agricultural fungicides [0004] The 1,3,4-thiadiazole fungicides such as Dicumazole and Bis-ADTA used to be effective agents for the control of rice bacterial blight, a refractory disease of rice, but due to the serious teratogenic effect and the growing problem of drug resistance. Later, it was reported that th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N43/824A01P3/00A61K31/433A61P35/00A61P35/02
CPCA01N43/82C07D417/12
Inventor 崔紫宁田浩胡德坤李亚胜宋高鹏刘星宇
Owner SOUTH CHINA AGRI UNIV
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