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Synthesis method of nicotinoyl hydrazone Schiff base compound as well as application of compound to bactericide

A technology of nicotinyl hydrazone Schiff base and synthesis method, which is applied in the direction of fungicides, botanical equipment and methods, applications, etc., and can solve the problem that the mechanism of acylhydrazone and its complexes is poorly understood, and the relationship between structure and activity is not very clear and other problems, to achieve the effects of easy industrialized large-scale application, easy separation, and low requirements for production equipment

Inactive Publication Date: 2018-11-20
HUAIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A large number of studies have shown that the biological activity of acylhydrazones increases compared with the corresponding ligands after the formation of complexes, but little is known about the biological activity mechanism of acylhydrazones and their complexes. The relationship between is not very clear, so further research work in this area is needed

Method used

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  • Synthesis method of nicotinoyl hydrazone Schiff base compound as well as application of compound to bactericide
  • Synthesis method of nicotinoyl hydrazone Schiff base compound as well as application of compound to bactericide
  • Synthesis method of nicotinoyl hydrazone Schiff base compound as well as application of compound to bactericide

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Embodiment 1

[0034] The synthetic method of the cinnamaldehyde nicotinyl hydrazone of the present embodiment, the method comprises the following steps:

[0035] (1) Synthesis of intermediate nicotinic acid hydrazide: 10 mL of hydrazine hydrate with a mass fraction of 80 wt % (0.165 mol) was dissolved in 50 mL of absolute ethanol, transferred to a 150 mL three-necked flask, and mixed uniformly. Add 20 mL (0.147 mol) of ethyl nicotinate dropwise through the dropping funnel (control the drop rate to 1 drop per second). Control the reaction temperature to 80°C, reflux and stir the reaction, and track it with TCL. After the reaction is over, let it stand and cool to room temperature. A white solid precipitates out and is filtered with suction to obtain the crude product 1. The crude product 1 is recrystallized with absolute ethanol. , vacuum-dried to obtain 12.658 g of white needle-shaped crystals (nicotinic acid hydrazide), with a yield of 79%.

[0036](2) Synthesis of the target compound: Di...

Embodiment 2

[0048] The synthetic method of the 1-naphthaldehyde nicotinyl hydrazone of the present embodiment, described method comprises the steps:

[0049] (1) Synthesis of intermediate nicotinic acid hydrazide: 10 mL of hydrazine hydrate with a mass fraction of 80 wt % (0.165 mol) was dissolved in 50 mL of absolute ethanol, transferred to a 150 mL three-necked flask, and mixed uniformly. Add 20 mL (0.147 mol) of ethyl nicotinate dropwise through the dropping funnel (control the drop rate to 1 drop per second). Control the reaction temperature to 80°C, reflux and stir the reaction, TCL tracking, after the reaction, let it stand and cool to room temperature, a white solid precipitates out, filter with suction to obtain the crude intermediate product, and recrystallize the crude product with absolute ethanol, After vacuum drying, 12.658 g of white needle-shaped crystals (nicotinic acid hydrazide) were obtained, with a yield of 79%.

[0050] (2) Synthesis of the target compound: Dissolve ...

Embodiment 3

[0062] The synthesis method of the pyridine-4-formaldehyde nicotinyl hydrazone of the present embodiment, the method comprises the following steps:

[0063] (1) Synthesis of intermediate nicotinic acid hydrazide: 10 mL of hydrazine hydrate with a mass fraction of 80 wt % (0.165 mol) was dissolved in 50 mL of absolute ethanol, transferred to a 150 mL three-necked flask, and mixed uniformly. Add 20 mL (0.147 mol) of ethyl nicotinate dropwise through the dropping funnel (control the drop rate to 1 drop per second). Control the reaction temperature to 80°C, reflux and stir the reaction, TCL tracking, after the reaction, let it stand and cool to room temperature, a white solid precipitates out, filter with suction to obtain the crude intermediate product, and recrystallize the crude product with absolute ethanol, After vacuum drying, 12.658 g of white needle-like crystals (nicotinic acid hydrazide) were obtained with a yield of 79%.

[0064] (2) Synthesis of the target compound: D...

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Abstract

The invention relates to a synthesis method of a nicotinoyl hydrazone Schiff base compound as well as application of the compound to bactericide, and relates to the technical field of organic synthesis. The synthesis method of the nicotinoyl hydrazone Schiff base compound comprises two steps of synthesizing an intermediate nicotinoylhydrazine and synthesizing a target product, wherein the nicotinoylhydrazine is prepared by carrying out a refluxing stirring reaction among raw materials such as hydrazine hydrate, ethyl nicotinate and absolute ethanol, carrying out a reaction under the conditionof 80 DEG C for synthesis, and performing aftertreatment; the target product is prepared by performing refluxing stirring reaction on the prepared intermediate nicotinoylhydrazine as well as a small amount of glacial acetic acid and aldehyde compound under the condition of 65 DEG C, performing suction filtration and performing recrystallization. The synthesis reaction is simple to operate and theyield of products is high; furthermore, the synthesis method is low in equipment requirement, low in production cost and easy in industrialized large-scale application. In addition, the synthesized nicotinoyl hydrazone Schiff base compound can serve as the bactericide to selectively kill germs, and the prevention effect on wheat powdery mildew can reach to 83.1 percent.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, and relates to a synthesis method and application of acylhydrazone compounds, more specifically, the present invention relates to a synthesis method of nicotinyl hydrazone Schiff base compounds and their application in fungicides . Background technique [0002] Nitrogen-containing compounds have a very close relationship with medical science, life science, material science, etc. In recent years, more and more studies have been conducted. Acylhydrazone compounds are a type of nitrogen-containing compounds that contain CONHN=C active units in their molecules. The special structural unit makes the acylhydrazone compounds exhibit a wide range of biological activities, such as insecticidal, bactericidal, herbicidal, anti-tumor, etc., and is widely used in the fields of pesticides and medicines. For example, metaflumizone (metaflumizone) is a commercial product. It is a kind of acylh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/88C07D409/12A01P3/00A01N43/40
CPCA01N43/40C07D213/88C07D409/12
Inventor 林红卫刘益林李元祥
Owner HUAIHUA UNIV
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