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Semicarbazone compound and preparation method and application thereof

A technology of semicarbazides and compounds, which is applied in the field of pesticides, can solve the problems of no semicarbazone compounds, etc., and achieve the effects of simple structure, good control effect, and easy synthesis

Active Publication Date: 2016-03-30
TONGLING FENGDAN PLANTING TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there is no report on the use of semicarbazone compounds as agricultural fungicides

Method used

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  • Semicarbazone compound and preparation method and application thereof
  • Semicarbazone compound and preparation method and application thereof
  • Semicarbazone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] compound (C 14 h 12 o 2 N 3 F) Preparation

[0033] (1) Synthesis of intermediate 1-(4-fluorophenyl)-3-(2-furyl)-2-propen-1-one

[0034] Dissolve 0.02 mol of 4-fluoroacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-fluorophenyl)-3-(2-furyl)-2-propen-1-one.

[0035] (2) Synthesis of the target compound

[0036] Dissolve 0.015 mol of semicarbazide in 20 mL of 90% ethanol, and add 1.5 mL of glacial aceti...

Embodiment 2

[0039] compound (C 14 h 12 o 2 N 3 Cl) Preparation

[0040] (1) Synthesis of intermediate 1-(4-chlorophenyl)-3-(2-furyl)-2-propen-1-one

[0041] Dissolve 0.02 mol of 4-chloroacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-Chlorophenyl)-3-(2-furyl)-2-propen-1-one.

[0042] (2) Synthesis of the target compound

[0043] Dissolve 0.015 mol of semicarbazide in 20 mL of 90% ethanol, and add 1.5 mL of glacial acet...

Embodiment 3

[0046] compound (C 14 h 12 o 2 N 3 Br) preparation

[0047] (1) Synthesis of intermediate 1-(4-bromophenyl)-3-(2-furyl)-2-propen-1-one

[0048] Dissolve 0.02 mol of 4-bromoacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-bromophenyl)-3-(2-furyl)-2-propen-1-one.

[0049] (2) Synthesis of the target compound

[0050] Dissolve 0.015 mol of semicarbazide in 20 mL of 90% ethanol, and add 1.5 mL of glacial acetic ...

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Abstract

The invention provides a semicarbazone compound and a preparation method and application thereof. The structural general formula of the compound is shown in the description, wherein the R represents fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, methyl, methoxy or nitro in the general formula (I). The compound is simple and novel in structure and easy to synthesize and has a better prevention and control effect on plant pathogenic fungi. The compound has not been reported in an existing plant pathogenic fungus inhibitor.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a semicarbazone compound and a preparation method and application thereof. Background technique [0002] Semicarbazide, also known as carbamohydrazide, is an important fine chemical and an important intermediate in the daily chemical, pharmaceutical and pesticide industries. It is used to prepare photochromic dyes on thermal recording paper, and to produce nitrofurazone, Adrenochrome hydrazone, hydroprednisone, hydrocortisone and other drugs are also widely used in the manufacture of other medicines, pesticides and other products. [0003] As we all know, the furan ring is an electron-rich system, and it is easy to form intermolecular hydrogen bonds with various biological enzymes. Therefore, some compounds containing furan rings, whether natural or synthetic, have a broad spectrum of biological activities. Bacteria, anti-virus, anti-tumor, insecticide and weed control etc. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52A01P3/00
CPCA01N47/34C07D307/52
Inventor 唐孝荣杨建高素美刘辉高扬徐志宏曾义张燕杜泉王玲
Owner TONGLING FENGDAN PLANTING TECH DEV
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