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Thiosemicarbazone derivatives, preparation method and applications thereof

A technology of thiosemicarbazone and its derivatives, which is applied in the field of pesticides to achieve good control effect, simple structure and easy synthesis

Active Publication Date: 2016-03-09
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 thiosemicarbazone derivatives as agricultural fungicides

Method used

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  • Thiosemicarbazone derivatives, preparation method and applications thereof
  • Thiosemicarbazone derivatives, preparation method and applications thereof
  • Thiosemicarbazone derivatives, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] compound (C 14 h 12 N 3 S 2 Br) preparation

[0034] (1) Synthesis of intermediate 1-(4-bromophenyl)-3-(2-thienyl)-2-propen-1-one

[0035] Dissolve 0.02 mol of 4-bromoacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under ice-bath stirring, the mixture of 0.02mol 2-thiophenecarbaldehyde and 20mL of absolute ethanol was slowly dropped into the above-mentioned mixed solution with a constant pressure dropping funnel, reacted at 0-5°C, and was tested with a thin-layer silica gel plate (TLC ) to check that 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-thienyl)-2-propen-1-one.

[0036] (2) Synthesis of the target compound

[0037] Dissolve 0.015 mol of thiosemicarbazide in 20 mL of...

Embodiment 2

[0040] compound (C 14 h 12 N 3 S 2 Cl) Preparation

[0041] (1) Synthesis of intermediate 1-(3-chlorophenyl)-3-(2-thienyl)-2-propen-1-one

[0042] Dissolve 0.02 mol of 3-chloroacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under ice-bath stirring, the mixture of 0.02mol 2-thiophenecarbaldehyde and 20mL of absolute ethanol was slowly dropped into the above-mentioned mixed solution with a constant pressure dropping funnel, reacted at 0-5°C, and was tested with a thin-layer silica gel plate (TLC ) to check that 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 -(3-Chlorophenyl)-3-(2-thienyl)-2-propen-1-one.

[0043] (2) Synthesis of the target compound

[0044] Dissolve 0.015 mol of thiosemicarbazide in 20 mL...

Embodiment 3

[0047] compound (C 14 h 11 N 3 S 2 Preparation of FBr)

[0048] (1) Synthesis of intermediate 1-(4-fluorophenyl)-3-(5-bromo-2-thienyl)-2-propen-1-one

[0049] Dissolve 0.02 mol of 4-fluoroacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. While stirring in an ice bath, slowly drop a mixture of 0.02mol 5-bromo-2-thiophenecarbaldehyde and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and use a thin layer Silica gel plates (TLC) were used to check the completion of the reaction. 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-(5-bromo-2-thienyl)-2-propen-1-one.

[0050] (2) Synthesis of the target compound

[0051] Dissolve 0.015 mol of thiosemicarbaz...

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Abstract

The invention provides thiosemicarbazone derivatives, a preparation method and applications thereof. The structural formula of the derivatives is represented in the description. In the formula (I), the R1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a methoxyl group, or a nitro group; and the R2 represents a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group. The provided derivatives have a simple and novel structure, are easy to synthesize, and has a good control effect on plant pathogenic fungi. At present, the provided derivatives have not been used to prepare a plant pathogenic fungus inhibitor.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a thiosemicarbazone derivative and a preparation method and application thereof. Background technique [0002] Thiosemicarbazide is an important fine chemical, which can be used to determine chromium, identify aldehydes, ketones, sugars, and prepare 1,2,4-triazoles, etc. It is also an important pharmaceutical and pesticide intermediate. Thiosemicarbazide derivatives have good biological activities, such as antifungal, antibacterial, antiviral, herbicide and plant growth regulator. At the same time, they also show good application prospects in the field of supramolecular chemistry such as molecular recognition and self-assembly. Therefore, research on thiosemicarbazide derivatives has been very active in recent years. [0003] Thiophene is an important member of heterocyclic compounds and plays a very important role. The research on thiophene derivatives also plays a very im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22A01P3/00
CPCC07D333/22
Inventor 唐孝荣杨建高素美刘辉高扬李唯一曾义徐志宏张燕王玲
Owner TONGLING FENGDAN PLANTING TECH DEV
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