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Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof

A technology containing oxadiazoles and thiadiazoles, which is applied in the field of oxadiazoles

Inactive Publication Date: 2014-07-02
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there is no synthesis of 2-(4-methyl-1,2,3-thiadiazol-5-yl)-5-(substituted alkylthio)-1,3,4-oxadiazole derivatives Literature reports on the study of its herbicidal activity

Method used

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  • Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof
  • Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof
  • Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 2-(2,4-dichlorobenzylthio)-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-oxadiazole 1

[0024] Yield 86%, melting point 85-86°C; 1 H NMR (CDCl 3 , 400MHz), δ: 3.06(s, 3H, Het-Me), 4.60(s, 2H, SCH 2 ), 7.22 (d, J=8.49Hz, 1H, ArH), 7.44 (s, 1H, ArH), 7.61 (d, J=8.27Hz, 1H, ArH). MS (ESI), m / z: 360 ( M+1).

Embodiment 2

[0026] 2-(3-Chlorobenzylthio)-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-oxadiazole 2

[0027] Yield d73.5%, melting point 88-89°C; 1 H NMR (CDCl 3 , 400MHz), δ: 3.06(s, 3H, Het-Me), 4.51(s, 2H, SCH 2 ), 7.30(s, 2H, ArH), 7.34-7.39(m, 1H, ArH), 7.47(s, 1H, ArH). MS(ESI), m / z: 326(M+1).

Embodiment 3

[0029] 2-(3-fluorobenzylthio)-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-oxadiazole 3

[0030] Yield 88%, melting point 63-64°C; 1 H NMR (CDCl 3 , 400MHz), δ: 3.06(s, 3H, Het-Me), 4.53(s, 2H, SCH 2 ), 7.04(t, J=7.46Hz, 1H, ArH), 7.19(d, J=9.27Hz, 1H, ArH), 7.29-7.35(m, 2H, ArH). MS (ESI), m / z: 309(M+1).

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Abstract

The invention discloses a thiadiazole-containing oxadiazole compound shown in a formula (I), a preparation method of the compound and application of the compound to control of barnyard grass and rape. The compound is a novel compound with herbicidal activity, and provides a foundation for research and development of novel pesticides.

Description

(1) Technical field [0001] The invention relates to a thiadiazole-containing oxadiazole compound, namely 2-(4-methyl-1,2,3-thiadiazol-5-yl)-5-(substituted alkylthio)-1, 3,4-oxadiazole derivatives and their preparation and application. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. 1,3,4-Oxadiazole compounds also have very important biological activities, including anti-inflammatory, anti-cancer, anti-viral, antibacterial and herbicidal activities. For example, the synthetic 2-substituted pyrazole-5-methylthio-1,3,4-oxadiazole exhibits good inhibitory activity against rice sheath blight at 100 mg / L; 2-methyl-5- Substituted benzylthio-1,3,4-oxadiazoles had better inhibitory effect on rapeseed at 100ppm. [0003] However, there is no synthesis of 2-(4-methyl-1,2,3-thiadiazol-5-yl)-5-(substituted alkylthio)-1,3,4-oxadia...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/828A01P13/00
CPCC07D417/04A01N43/82
Inventor 孙国香刘幸海陈松李永红曹耀艳
Owner YANCHENG INST OF TECH
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