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2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their synthesis method and application

An oxadiazole-based and methylaniline-based technology is applied in the directions of botanical equipment and methods, applications, and drug combinations, and can solve problems such as few therapeutic agents, unsatisfactory control effects, and pesticide residues.

Active Publication Date: 2016-11-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the problems of traditional fungal disease control agents (such as dexazone, pentachloronitrobenzene, carbendazim, etc.) caused by long-term application have become increasingly prominent, such as increased drug resistance, decreased control efficiency, and pesticide residues.
The currently developed plant viruses (Virus A, Virus Bick, Jinyebao, Virus A, etc.) are mainly protective agents, with few therapeutic agents, and the control effect is not ideal (the control effect is generally lower than 60%)

Method used

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  • 2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their synthesis method and application
  • 2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their synthesis method and application
  • 2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Example 1: Preparation of 2-(methylthio)-5-anilino-1,3,4-oxadiazole (TM1)

[0094] (1) Preparation of ethyl anilinate intermediate:

[0095] Throw aniline (20 g, 0.21 mol), pyridine (17 g, 0.21 mol) and anhydrous dichloromethane (100 mL) into a 250 mL three-necked flask, and slowly add ethyl chloroformate (30 g, 0.27 mol) dropwise under ice cooling Afterwards, the reaction at room temperature was completed for 2 h. The reaction was quenched, washed with water, and desolvated under reduced pressure to obtain 35.1 g of ethyl anilinate with a yield of 86%.

[0096] (2) Preparation of anilinoformohydrazide intermediate

[0097] Throw ethyl anilinate (16 g, 0.18 mol) and 80% hydrazine hydrate (90 g, 1.80 mol) into a 100 mL three-necked round-bottomed flask, and heat up to reflux for 20 h to complete the reaction. After cooling, white crystals were precipitated, which were obtained by suction filtration to obtain anilinoformohydrazide, and recrystallized in absolute ethano...

Embodiment 2

[0103] Example 2: Preparation of 2-(4-methylbenzylthio)-5-anilino-1,3,4-oxadiazole (TM2)

[0104] Steps (1)-(4) are the same as in Embodiment 1.

[0105] (5) Add intermediate 2-mercapto-5-(anilino)-1,3,4-oxadiazole potassium salt (0.50g, 2.0 mmol), 15 mL water, potassium carbonate (0.28 g, 2.0 mmol), stirred, added (0.34 g, 2.5 mmol) iodomethane and KI (16.6 mg, 0.10 mmol). The reaction was stirred at room temperature (20 °C) for 5 h. The reaction solution was extracted with dichloromethane, concentrated, and separated by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a white solid: 0.224 g, yield 35.5%.

Embodiment 3

[0106] Example 3: Preparation of 2-(4-fluorobenzylthio)-5-(2-methylanilino)-1,3,4-oxadiazole (TM3)

[0107] Steps (1)-(4) are the same as in Embodiment 1.

[0108] (5) Add intermediate 2-mercapto-5-(2-methylanilino)-1,3,4-oxadiazole potassium salt (0.80 g, 3.3 mmol), 15 mL water, Potassium carbonate (0.45 g, 3.3 mmol), stirred, added (0.77 g, 4.1 mmol) 4-fluorobenzyl bromide and KI (27.1 mg, 0.16 mmol). The reaction was stirred at room temperature (20 °C) for 5 h. The reaction solution was extracted with dichloromethane, concentrated, and separated by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a white solid: 0.416 g, yield 40.4%.

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Abstract

The invention discloses a compound 2-substituent-5-substitued anilino-1,3,4-oxadiazole derivative with functions of resisting plant germs and plant viruses and a preparation method and an application thereof, wherein the structure of the compound is represented by the general formula (I). In the invention, the substituted arylamine is adopted as a start raw material, and a thioether compound is prepared by the steps of esterification, hydrazinolysis, salifying, ring closing and etherification; a sulfone compound is prepared by thioether oxidization. The compound disclosed by the invention has a good inhibiting effect on gibberella zeae, pepper fusarium wilt pathogen, valsa mali and tobacco mosaic virus and can be used for preparing medicines resisting plant germs and plant viruses.

Description

technical field [0001] The invention relates to chemical industry and pesticide, and the specific technology is 2-substituent-5-substituted anilino-1,3,4-oxadiazole derivatives and their preparation method and application. Background technique [0002] Fungal diseases are the largest category of plant diseases, and the proportion of plant virus diseases in plant diseases is second only to fungal diseases. These two diseases pose a serious threat to agricultural production and have become restrictions on my country's food security and agricultural reliability. important factor for sustainable development. However, the long-term use of traditional fungal disease control agents (such as dexamethasone, pentachloronitrobenzene, and carbendazim) has increasingly prominent problems such as increased bacterial resistance, decreased control efficacy, and pesticide residues. The currently developed plant viruses (Virus A, Virus Bick, Jinyebao, Virus A, etc.) are mainly protective agen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/113A01N43/824A61P3/00A61P1/00
CPCA01N43/82C07D271/113
Inventor 杨松邝继清邓华波薛伟吴志兵吴世喜张腾腾陈玉婷周青叶意强
Owner GUIZHOU UNIV
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