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Heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazole-5-radical) and application thereof

A technology for heterocyclic compounds and oxadiazoles, which is applied in the fields of chemical industry and pesticides, can solve problems such as unreported synthesis of bisoxadiazoles, and achieve the effects of good inhibitory activity, good control effect and broad application prospects.

Active Publication Date: 2014-06-18
GAUNGXI TIANYUAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, many such compounds have been developed as pesticides and medicines, but the synthesis of compounds with bisoxadiazole sulfones has not been reported so far

Method used

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  • Heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazole-5-radical) and application thereof
  • Heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazole-5-radical) and application thereof
  • Heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazole-5-radical) and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Preparation of bis(2-hydrocarbylsulfonyl-1,3,4-oxadiazol-5-yl)benzene and its substitutes

[0060] (1) Synthesis of substituted dimethyl phthalate intermediate

[0061] Add 0.10 mol of substituted phthalic acid indicated by the general formula in a round bottom flask, dissolve in 150 mL of methanol, add 15 mL of concentrated sulfuric acid, and reflux for 24 hours. Pour into 500mL of water, separate, wash with water, and dry to obtain dimethyl substituted phthalate.

[0062] (2) Synthesis of Substituted Phthalohydrazide Intermediates

[0063]Add 0.07 mol of substituted dimethyl phthalate and 150 mL of methanol into a round bottom flask, add 100 mL of hydrazine hydrate, reflux for 24 hours, cool to room temperature, let stand for 5 hours, filter, wash with water, and dry to obtain substituted phthalic hydrazide.

[0064] (3) Synthesis of substituted 1,3-bis(2-mercapto-1,3,4-oxadiazol-5-yl)benzene intermediate

[0065] Add 0.03mol of substituted phthalohydrazide to the ...

Embodiment 2

[0085] Preparation of bis(2-hydrocarbylsulfonyl-1,3,4-oxadiazol-5-yl)biphenyl and its substitutes

[0086] (1) Synthesis of substituted dimethyl diphenylcarboxylate

[0087] Add 0.10 mol g of the substituted biphenyl dicarboxylic acid indicated in the general reaction formula to a round bottom flask, dissolve it in 150 mL of methanol, add 15 mL of concentrated sulfuric acid, and reflux for 24 hours. Pour into 500mL of water, separate, wash with water, and dry to obtain dimethyl substituted biphenyl dicarboxylate.

[0088] (2) Synthesis of substituted biphenyl dicarboxylic hydrazides

[0089] Add 0.07 mol of dimethyl substituted biphenyl dicarboxylate and 150 mL of methanol into a round bottom flask, add 100 mL of hydrazine hydrate, reflux for 24 hours, cool to room temperature, let stand for 5 hours, filter, wash with water, and dry to obtain substituted biphenyl dicarboxylic acid hydrazide .

[0090] (3) Synthesis of substituted bis(2-mercapto-1,3,4-oxadiazol-5-yl)biphenyl...

Embodiment 3

[0104] Example 3: Preparation of 2,6-bis(2-methylsulfonyl-1,3,4-oxadiazol-5-yl)-naphthalene

[0105] (1) Synthesis of dimethyl 2,6-naphthalene dicarboxylate

[0106] Add 20 g of 2,6-naphthalene dicarboxylic acid to a round bottom flask, dissolve it in 150 mL of methanol, add 15 mL of concentrated sulfuric acid, and reflux for 24 hours. Pour into 500mL of water, precipitate for 2 hours, filter, wash with water, and dry to obtain 20g of dimethyl 2,6-naphthalene dicarboxylate, with a yield of 89%.

[0107] (2) Synthesis of 2,6-naphthalene dicarboxylic acid hydrazide

[0108] Add 15g of dimethyl 2,6-naphthalene dicarboxylate and 150mL of methanol into a round bottom flask, add 80mL of hydrazine hydrate, reflux for 24 hours, cool to room temperature, let stand for 5 hours, filter, wash with water, and dry to obtain 2,6-naphthalene dicarboxylate Formic hydrazide 12.5g, yield 83%.

[0109] (3) Synthesis of 2,6-bis(2-mercapto-1,3,4-oxadiazol-5-yl)naphthalene

[0110] Add 5 g of 2,...

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Abstract

The invention belongs to the field of chemical engineering and pesticides, and particularly relates to a heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazole-5-radical) and application thereof. The structure of the heterocyclic compound is shown in the specification. In a general formula, R is hydrogen, C1-C5 alkyl radicals, C1-C5 halogenated alkyl radicals, C2-C5 alkenyl, and ester, benzyl or substituted benzyl of C2-C5, and Z is hydrocarbyl or substituted hydrocarbon thereof, phenyl, substituted phenyl, biphenylyl, substituted biphenylyl, naphthyl, substituted naphthyl, diphenyl hydrocarbyl, substituted diphenyl hydrocarbyl, and diphenyl ether or substituted diphenyl ether. The heterocyclic compound has very good inhibitory activity on rhizoctonia solani, fusarium asiaticum, borrytis cinerea, physalospora piricala, helminthossporium oryzae, tobacco bacterial wilt and rice brown blotches, can be applied to prevention and control of plant diseases and has wide application prospect.

Description

technical field [0001] The invention belongs to the fields of chemical industry and pesticides, in particular to a heterocyclic compound containing bis(2-substituted sulfonyl-1,3,4-oxadiazol-5-yl) and its application. Background technique [0002] With the improvement of living standards, people have higher and higher requirements for the agricultural products they eat, and agriculture has higher and higher requirements for pesticides. On the one hand, pesticides pollute the environment, on the other hand, the resistance of the control objects is getting stronger and stronger. . About 80% of plant diseases in the world are caused by bacteria and fungi. Plant bacterial and fungal diseases not only reduce crop yield and quality, but also cause greater damage and losses during the storage, processing and transportation of agricultural products. Some can also produce mycotoxin contamination. It is imminent to develop a new generation of high-efficiency, low-toxic new green fun...

Claims

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Application Information

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IPC IPC(8): C07D271/113A01N43/824A01P3/00
CPCA01N43/82C07D271/113
Inventor 张青李卫国李现玲
Owner GAUNGXI TIANYUAN BIOCHEM
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