Thiophene chalcone semicarbazone Schiff base compounds, and preparation method and applications thereof

A technology for thiophene chalcone semicarbazide and compound is applied in the field of thiophene chalcone semicarbazide Schiff base compounds and preparation thereof, and achieves the effects of easy synthesis, novel structure and simple structure

Active Publication Date: 2016-03-02
ZONGYANG COUNTY ZHONGBANG TECH INFORMATION CONSULTING CO LTD
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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 thiophenechalcone semicarbazone Schiff base compounds as agricultural fungicides

Method used

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  • Thiophene chalcone semicarbazone Schiff base compounds, and preparation method and applications thereof
  • Thiophene chalcone semicarbazone Schiff base compounds, and preparation method and applications thereof
  • Thiophene chalcone semicarbazone Schiff base compounds, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] compound (C 14 h 12 ON 3 SF) preparation

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

[0035] (2) Synthesis of the target compound

[0036] Dissolve 0.015 mol of semicarbazide in 20 mL of 90% ...

Embodiment 2

[0039] compound (C 20 h 17 ON 3 S) Preparation

[0040] (1) Synthesis of intermediate 1-(4-biphenyl)-3-(2-thienyl)-2-propen-1-one

[0041] Dissolve 0.02 mol of biphenyl monoethyl ketone 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-biphenyl)-3-(2-thienyl)-2-propen-1-one.

[0042] (2) Synthesis of the target compound

[0043] Dissolve 0.015 mol of semicarbazide in 20 mL of 90% etha...

Embodiment 3

[0046] compound (C 14 h 12 ON 3 Preparation of SCl)

[0047] (1) Synthesis of intermediate 1-(3-chlorophenyl)-3-(2-thienyl)-2-propen-1-one

[0048] 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.

[0049] (2) Synthesis of the target compound

[0050] Dissolve 0.015 mol of semicarbazide in 20 mL of ...

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Abstract

The invention provides thiophene chalcone semicarbazone Schiff base compounds, and a preparation method and applications thereof. Structure general formula of the thiophene chalcone semicarbazone Schiff base compounds is represented by a formula I in the invention, wherein R is used for representing single substitution or double substitution, and is used for representing fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, methyl, methoxyl, or phenyl. The thiophene chalcone semicarbazone Schiff base compounds are simple and novel in structure, are convenient to be synthesized, and possess excellent control effects on plant pathogenic fungi. The thiophene chalcone semicarbazone Schiff base compounds are taken as plant pathogenic fungi inhibitors for the first time.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a thienchalcone semicarbazone Schiff base compound and a preparation method and application thereof. Background technique [0002] Schiff base refers to a class of organic compounds with >C=N- structure formed by the condensation reaction of primary amines with aldehydes or ketones. A large number of studies have shown that Schiff base compounds play a very important role in the fields of medicine, catalysis, analytical chemistry, corrosion and photochromism. At the same time, Schiff base compounds also have good biological activities, such as insecticidal, antifungal, antibacterial, anticancer, antiparasitic, weeding and so on. Therefore, the research and development of Schiff base compounds will have a broad space. [0003] Thiophene is an important member of heterocyclic compounds and plays a very important role. The research on thiophene derivatives also plays a very...

Claims

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Application Information

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IPC IPC(8): C07D333/22A01N43/10A01P3/00
CPCA01N43/10C07D333/22
Inventor 唐孝荣杨建高素美刘辉高扬徐志宏李唯一曾义张燕王玲
Owner ZONGYANG COUNTY ZHONGBANG TECH INFORMATION CONSULTING CO LTD
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