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Thiophene allyl alcohol compound as well as preparation method and application thereof

A technology of thiophene allyl alcohol and compound, which is applied in the field of pesticides to achieve the effect of novel structure, good control effect and simple structure

Active Publication Date: 2016-03-23
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] However, so far, there is no report on the use of thiophene allyl alcohols as agricultural fungicides

Method used

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  • Thiophene allyl alcohol compound as well as preparation method and application thereof
  • Thiophene allyl alcohol compound as well as preparation method and application thereof
  • Thiophene allyl alcohol compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] compound (C 13 h 11 OSF) preparation

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

[0035] Add 0.01mol of 4-fluoroacetophenone and 10mL of absolute ethanol into a 50mL three-necked flask, and then add 5mL of 10% NaOH solution into it. While stirring in an ice bath, slowly drop the mixture of 0.01mol 2-thiophenecarbaldehyde and 10mL absolute ethanol into a three-necked flask with a constant pressure dropping funnel, react at 0-5°C, and use 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.

[0036] (2) Synthesis of the target compound

[0037] Add 0.005mol of self-made intermediate and 30mL of absolute ethano...

Embodiment 2

[0040] compound (C 13 h 10 Preparation of OSClBr)

[0041] (1) Synthesis of intermediate 1-(4-chlorophenyl)-3-(5-bromo-2-thienyl)-2-propen-1-one

[0042] Add 0.01mol of 4-chloroacetophenone and 10mL of absolute ethanol into a 50mL three-necked flask, and then add 5mL of 10% NaOH solution into it. While stirring in an ice bath, slowly drop the mixture of 0.01mol 5-bromo-2-thiophenecarbaldehyde and 10mL of absolute ethanol into a three-necked flask 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-Chlorophenyl)-3-(5-bromo-2-thienyl)-2-propen-1-one.

[0043] (2) Synthesis of the target compound

[0044] Add 0.005mol of self-m...

Embodiment 3

[0047] compound (C 13 h 10 OSBr 2 ) preparation

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

[0049] Add 0.01mol of 4-bromoacetophenone and 10mL of absolute ethanol into a 50mL three-necked flask, and then add 5mL of 10% NaOH solution into it. While stirring in an ice bath, slowly drop the mixture of 0.01mol 5-bromo-2-thiophenecarbaldehyde and 10mL of absolute ethanol into a three-necked flask 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-bromophenyl)-3-(5-bromo-2-thienyl)-2-propen-1-one.

[0050] (2) Synthesis of the target compound

[0051] Add 0.005mol of self-made ...

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PUM

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Abstract

The invention provides a thiophene allyl alcohol compound. A general structural formula of the thiophene allyl alcohol compound is shown in the specification, wherein in the general formula (I), R1 is a hydrogen atom, a chlorine atom, a bromine atom, methyl or methoxy; and R2 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, methyl, methoxy or nitro. The thiophene allyl alcohol compound provided by the invention has a simple and novel structure, is easy to synthesize, is low in cost, has better control effects on plant pathogenic fungi and is 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 thiophene allyl alcohol compound and a preparation method and application thereof. Background technique [0002] Allyl alcohol, also known as allyl alcohol, is an important fine chemical. It is also an important intermediate in the daily chemical, pharmaceutical and pesticide industries for the production of epichlorohydrin, glycerin, 1,4-butanediol, glycerin allyl ether, allyl glycidyl ether, glycidol, olefin Chemical products such as propylamine and allyl ester polymerized monomers are also widely used in the manufacture of other pharmaceuticals, pesticides and flavors. [0003] Thiophene is an important member of heterocyclic compounds and plays a very important role. The research on thiophene derivatives also plays a very important role in medicine and pesticide chemistry. Thiophene derivatives have various biological activities, such as antibacterial, antiviral, anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/16C07D333/28A01N43/10A01P3/00
CPCA01N43/10C07D333/16C07D333/28
Inventor 唐孝荣高扬杨建刘辉高素美徐志宏张燕李唯一杜泉王玲
Owner 铜陵博锋实业有限公司
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