1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative and preparation and application thereof

A technology of thiadiazole sulfide and benzamide, which is applied to 2-(trifluoromethyl)benzamide derivatives containing 1,3,4-thiadiazole sulfide (sulfone), its preparation and Application field

Active Publication Date: 2019-03-12
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there is no research report about 2-(trifluoromethyl)benzamide compounds containing 1,3,4-thiadiazole sulfide (sulfone) having both nematicidal and antibacterial effects

Method used

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  • 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative and preparation and application thereof
  • 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative and preparation and application thereof
  • 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: N-(2-((3-chloro-5-(trimethyl)pyridin-2-yl)sulfur)-1,3,4-thiadiazol-2-yl)-5-(tri The synthetic (compound number is A1) of fluoromethyl) benzamide comprises the following steps:

[0058] (1) Put thiosemicarbazide (10.0mmol), potassium hydroxide (15.0mmol) and absolute ethanol (60mL) as the solvent into a 100mL three-neck flask, stir continuously at room temperature until the solid dissolves and slowly add carbon disulfide ( 15.0mmol), and then heated to reflux for 8-10h. After the reaction was completed, the ethanol removed under reduced pressure was added to ice water, and the pH was adjusted to 3-4 with 5% hydrochloric acid, and then the solid was collected by filtration and recrystallized with absolute ethanol to obtain intermediate 2-amino-5-mercapto-1,3,4-thiadiazole;

[0059] (2) Put 2-amino-5-mercapto-1,3,4-oxadiazole (4.0mmol), potassium carbonate (6.0mmol) and DMF (2mL) as solvent into a 100mL three-necked flask, and keep stirring until After the sol...

Embodiment 2

[0061] Example 2: Synthesis of N-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-2-(trifluoromethyl)benzamide (compound number is A2), Include the following steps:

[0062] (1) with the (1) step of embodiment 1;

[0063] (2) Put 2-amino-5-mercapto-1,3,4-oxadiazole (4.0mmol), potassium carbonate (6.0mmol) and DMF (2mL) as solvent into a 100mL three-necked flask, and keep stirring until After the solid was dissolved, methyl iodide (4.0 mmol) was slowly added dropwise, and then stirred at room temperature for 2-6 h. After the reaction was completed, the solvent was removed under reduced pressure, ice water was added, and the solid was collected by filtration and recrystallized with absolute ethanol to obtain intermediate 2- Amino-5-methylmercapto-1,3,4-oxadiazole;

[0064] (3) 2-Amino-5-methylmercapto-1,3,4-oxadiazole (2.6mmol), potassium carbonate (3.9mmol) and toluene (20mL) were used as solvents, and put into a 100mL three-necked flask, and the solid After complete dissolution, add ...

Embodiment 3

[0065] Example 3: Synthesis of N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(trifluoromethyl)benzamide (compound number is A3), Include the following steps:

[0066] (1) with the (1) step of embodiment 1;

[0067] (2) Put 2-amino-5-mercapto-1,3,4-oxadiazole (4.0mmol), potassium carbonate (6.0mmol) and DMF (2mL) as solvent into a 100mL three-necked flask, and keep stirring until After the solid was dissolved, ethyl bromide (4.0 mmol) was slowly added dropwise, and then stirred at room temperature for 2-6 h. After the reaction was completed, the solvent was removed under reduced pressure, ice water was added, and the solid was collected by filtration and recrystallized from absolute ethanol to obtain intermediate 2 -Amino-5-ethylmercapto-1,3,4-oxadiazole;

[0068] (3) Put 2-amino-5-ethylmercapto-1,3,4-oxadiazole (2.6mmol), potassium carbonate (3.9mmol) and toluene (20mL) into a 100mL three-necked flask as solvent, and wait until the solid After complete dissolution, add 2-(trifl...

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Abstract

The invention discloses a 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative and preparation and application thereof. A general formula of the 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative is as shown in the description, wherein R1 is methyl or ethyl or 2-chloroethyl or 2-fluoroethyl or 2-bromomethyl or propyl or butyl or amyl or 4-cyanobenzyl or 4-chlorobenzyl or 2-fluorobenzyl or cyanomethyl or 2-cyanoethyl or 3-cyanopropy; X is S or -S(O)2-. The 1,3,4-thiadiazole thioether (sulfone)-containing 2-(trifluoromethyl)benzamide derivative can control compound infection of meloidogyne incognita and rice bacterial leaf blight, meloidogyne incognita and tobacco bacterial wilt, and meloidogyne incognita and citrus bacterial canker disease.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a class of 2-(trifluoromethyl)benzamide derivatives containing 1,3,4-thiadiazole sulfide (sulfone), and also to the 1-containing , the preparation method of 2-(trifluoromethyl)benzamide derivatives of 3,4-thiadiazole sulfide (sulfone), and the 1,3,4-thiadiazole sulfide (sulfone)-containing Application of 2-(trifluoromethyl)benzamide derivatives in nematicides and inhibition of crop bacterial diseases. Background technique [0002] Plant parasitic nematodes are widely distributed all over the world with a wide range of hosts. When host plants are infested by nematodes, they are often easily infected by pathogens such as bacteria and fungi, resulting in a complex infection system that seriously threatens the safe production of crops. Diseases caused by plant parasitic nematodes and bacteria in my country's agricultural production are characterized by high frequency, sev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135C07D417/12A01N43/824A01P1/00A01P5/00
CPCA01N43/82C07D285/135C07D417/12
Inventor 宋宝安陈吉祥易崇粉伍思凯王邵波何方成王艳菊魏成前胡德禹
Owner GUIZHOU UNIV
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