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1-(2-furyl)-1,3-pentadiene compound and its preparation method and application

The technology of a compound, pentadiene, is applied in the field of pesticides to achieve good control effect, simple structure and easy synthesis

Active Publication Date: 2018-12-04
铜陵博锋实业有限公司
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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 1-(2-furyl)-1,3-pentadiene compounds as agricultural fungicides

Method used

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  • 1-(2-furyl)-1,3-pentadiene compound and its preparation method and application
  • 1-(2-furyl)-1,3-pentadiene compound and its preparation method and application
  • 1-(2-furyl)-1,3-pentadiene compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] compound (C 16 h 14 o 2 N 3 Br) preparation

[0033] (1) Synthesis of intermediate 1-(4-bromophenyl)-5-(2-furyl)-2,4-pentadien-1-one

[0034] Dissolve 0.02 mol of 4-bromoacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. While stirring in an ice bath, slowly drop the mixture of 0.02mol 2-furan acrolein 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 plate to (TLC) 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-bromophenyl)-5-(2-furyl)-2,4-pentadien-1-one.

[0035] (2) Synthesis of the target compound

[0036] 0.015 mol of semicarbazide was dissolved in 20 mL of 90% ethanol, and 1.5 ...

Embodiment 2

[0039] compound (C 22 h 19 o 2 N 3 ) preparation

[0040] (1) Synthesis of intermediate 1-(4-biphenyl)-5-(2-furyl)-2,4-pentadien-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. While stirring in an ice bath, slowly drop the mixture of 0.02mol 2-furan acrolein 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 plate to (TLC) 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-biphenyl)-5-(2-furyl)-2,4-pentadien-1-one.

[0042] (2) Synthesis of the target compound

[0043] 0.015 mol of semicarbazide was dissolved in 20 mL of 90% ethanol, and 1.5 mL...

Embodiment 3

[0046] compound (C 16 h 14 o 2 N 3 Br) preparation

[0047] (1) Synthesis of intermediate 1-(3-bromophenyl)-5-(2-furyl)-2,4-pentadien-1-one

[0048] Dissolve 0.02 mol of 3-bromoacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. While stirring in an ice bath, slowly drop the mixture of 0.02mol 2-furan acrolein 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 plate to (TLC) 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 -(3-bromophenyl)-5-(2-furyl)-2,4-pentadien-1-one.

[0049] (2) Synthesis of the target compound

[0050] 0.015 mol of semicarbazide was dissolved in 20 mL of 90% ethanol, and 1.5 ...

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Abstract

The invention provides 1-(2-furyl)-1,3-pentadiene compounds as well as a preparation method and an application thereof. The general structural formula of the compounds is represented in the specification, wherein R in the general formula (I) represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, methyl, methoxyl, nitryl or phenyl and is substituted or di-substituted. The compounds are simple and novel in structure and easy to synthesize, have better control effect on plant pathogenic fungi, and are not reported in currently known plant pathogenic fungus inhibitors.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a 1-(2-furyl)-1,3-pentadiene compound and a preparation method and application thereof. Background technique [0002] Pesticide resistance has always been an unavoidable problem in the control of agricultural diseases and insect pests. After a period of use of pesticides, pests or pathogenic bacteria will develop resistance to them, especially for some pesticides with strong targets, the resistance will develop faster. Therefore, in the face of this problem, there is a constant need to invent new and improved compounds and compositions with insecticidal or fungicidal activity in the control of agricultural diseases and insect pests. At the same time, along with people's increasing demand for agricultural and livestock products and increasing emphasis on environmental protection, new pesticides with lower cost and environmental friendliness are always required. [0003] As we...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/52A01P3/00
CPCA01N47/34C07D307/52
Inventor 唐孝荣杨建高素美刘辉高扬张燕徐志宏曾义李唯一王玲
Owner 铜陵博锋实业有限公司
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