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Disulfide derivatives containing 1,3,4-oxa(thia)diazole, its preparation method and application

A technology of bissulfides and thiadiazoles, which is applied in the field of preparation of disulfide derivatives, can solve problems such as instability of sulfone compounds, difficulty in practical application, and increased cost, and achieve simple structure, low production cost, The effect of simple preparation process

Active Publication Date: 2019-06-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In 2014, Jin Linhong, Su Shihu, Liao Guoping (including phenoxymethyl sulfone derivatives and their synthesis and application[P]. CN 104045605 A, 2014-09-17) disclosed phenoxymethyl sulfone derivatives, and the results of biological activity tests showed that the target compounds A1, A3, A6, A8, A10, and A12 had good inhibitory effects on the tested fungi and bacteria. However, due to the instability of sulfone compounds, it is difficult to be practically applied. In addition, the use of potassium permanganate to oxidize and synthesize the target substance increases the cost and leads to a large amount of three wastes
[0008] So far, there is no research report on the nematicidal effect of 1,3,4-oxa(thia)adiazole sulfide compounds

Method used

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  • Disulfide derivatives containing 1,3,4-oxa(thia)diazole, its preparation method and application
  • Disulfide derivatives containing 1,3,4-oxa(thia)diazole, its preparation method and application
  • Disulfide derivatives containing 1,3,4-oxa(thia)diazole, its preparation method and application

Examples

Experimental program
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Embodiment 1

[0056] The synthesis of embodiment 1, 2-((4-fluorophenylthio)methyl)-5-ethylthio-1,3,4-oxadiazole (compound number is A1), comprises the following steps:

[0057] Step 1: Put substituted 4-fluorothiophenol and potassium carbonate into a 100mL three-necked round-bottomed flask, use absolute ethanol as solvent, stir for 5 minutes, then add ethyl chloroacetate dropwise, then react at room temperature for 6-8 h, TLC tracking the reaction process, after the raw material point disappeared, 80% hydrazine hydrate was added dropwise, and then refluxed for 6-8 h (molar ratio: 4-fluorothiophenol: potassium carbonate: ethyl chloroacetate: hydrazine hydrate=1 :1.4:1:2), reflux reaction, TLC to follow the reaction process, after the disappearance of the raw material point, stop the reaction, distill the ethanol off under reduced pressure, cool and stand still, wash with water and filter with suction to obtain white crystals, which are recrystallized with ethanol to obtain 4 - Fluorophenylth...

Embodiment 2

[0060] Example 2, the synthesis of 2-((4-fluorophenylthio)methyl)-5-methylthio-1,3,4-oxadiazole (compound number is A2), comprises the following steps:

[0061] Put the intermediate 2-mercapto-5-(4-fluorophenylthio)methyl-1,3,4-oxadiazole and sodium hydroxide obtained in the second step of Example 1 into a 100mL three-necked round-bottomed flask , and water as a solvent, after the solid is completely dissolved, add dropwise dimethyl sulfate (molar ratio: 2-mercapto-5-(4-fluorophenylthio)methyl-1,3,4-oxadiazole : sodium hydroxide: dimethyl sulfate = 1:1.3:1), then stirred at room temperature, followed the reaction process by TLC, after the disappearance of the raw material point, stopped the reaction, extracted with dichloromethane (30 mL×3), combined the organic layers, Dry with anhydrous magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain a yellow transparent oily liquid, which is purified by column chromatography (V 石油醚 :V 乙酸乙酯 =3:1) to ob...

Embodiment 3

[0062] Example 3, the synthesis of 2-((4-fluorophenylthio)methyl)-5-benzylthio-1,3,4-oxadiazole (compound number is A3), comprises the following steps:

[0063] Put the intermediate 2-mercapto-5-(4-fluorophenylthio)methyl-1,3,4-oxadiazole and sodium hydroxide obtained in the second step of Example 1 into a 100mL three-necked round-bottomed flask , and water as a solvent, after the solid is completely dissolved, benzyl chloride (molar ratio: 2-mercapto-5-(4-fluorophenylthio)methyl-1,3,4-oxadiazole:hydrogen Sodium oxide: benzyl chloride = 1:1.3:1), then stirred at room temperature, followed the reaction process by TLC, stopped the reaction after the disappearance of the raw material point, extracted with dichloromethane (30 mL×3), combined the organic layers, and washed with anhydrous sulfuric acid Dried over magnesium, filtered, evaporated the solvent under reduced pressure to obtain a solid, filtered and dried, and recrystallized with absolute ethanol to obtain 2-((4-fluorophe...

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Abstract

The invention discloses a disulfide derivative containing 1,3,4-oxa(thia)diazole and a preparation method and application of the derivative. The disulfide derivative has the following general formula (as shown in the specification), wherein R1 is selected from 4-chlorphenyl, 4-fluoro-phenyl, benzyl, 4-chloro-benzyl and other substituent groups; R2 is selected from methyl, ethyl, benzyl, 4-chloro-benzyl, ethyl acetate and other substituent groups; X is O or S. The disulfide derivative disclosed by the invention can serve as a medicine or agent for killing nematodes and inhibiting crop bacterium diseases.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and specifically relates to a disulfide derivative containing 1,3,4-oxa(thia)diazole, and to the 1,3,4-oxa(thia)diazole-containing The preparation method of the bissulfide derivatives, and the application in nematicides and inhibition of crop bacterial diseases. Background technique [0002] Nematodes are widely distributed all over the world and have a wide range of hosts. When host plants are infected by nematodes, they are often easily infected by the pathogens they carry, causing serious plant damage. Globally, agricultural losses due to plant-parasitic nematodes exceed $50 billion annually. Plant parasitic nematode diseases and bacterial diseases in my country's agricultural production have the characteristics of high frequency, serious damage, wide occurrence range, and difficulty in prevention and control. Crop bacterial diseases caused by bacteria are a major crop disease, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/113C07D285/125A01N43/824A01P5/00A01P1/00
CPCA01N43/82C07D271/113C07D285/125
Inventor 宋宝安陈吉祥杨松曾松贺呜田平义周大贵易崇粉李明伟王燕娇李向阳
Owner GUIZHOU UNIV
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