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Benzofuranol-based oxadiazole derivative and preparation method and application thereof

A compound and pharmaceutical technology, applied in the field of oxadiazole derivatives and their preparation, can solve the problems of low herbicidal activity, complicated preparation method and the like, and achieve the effects of simple preparation method, easy popularization and application, and high yield

Active Publication Date: 2019-07-16
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned 1,3,4-oxadiazole compounds are either complex in preparation method or have low herbicidal activity. Therefore, it is necessary to develop new 1,3,4-oxadiazole compounds for use in the herbicidal field

Method used

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  • Benzofuranol-based oxadiazole derivative and preparation method and application thereof
  • Benzofuranol-based oxadiazole derivative and preparation method and application thereof
  • Benzofuranol-based oxadiazole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of ethyl-2-((2,2-dimethyl-2,3-2,3-dihydrobenzofuran-7-yl)oxy)ethyl acetate (compound B):

[0026]

[0027] Dissolve compound A in anhydrous DMF, add K 2 CO 3 Stir at room temperature until dissolved, add ethyl chloroacetate, catalytic amount KI, stir and heat at 60°C for 6-8h, TLC detection. After the reaction, add a small amount of water and stir for 5 minutes, extract with ethyl acetate, and use anhydrous NaSO for the organic phase 4 To dry, spin dry. Petroleum ether: ethyl acetate = 40:1 column chromatography, the pure intermediate product B was obtained as a yellow viscous liquid with a yield of 90%. The molar ratio of compound A to ethyl chloroacetate is 1:1.5; MS-ESI, m / z 273.28[M+Na] + .HR-MS-EI m / z calcd for C 14 h 18 o 4 [M+H] + 250.2925, found 250.2940; 1 H NMR (600MHz, CDCl 3 )δ6.80(d,J=7.1Hz,1H),6.75–6.68(m,2H),4.71(s,2H),4.24(q,J=7.1Hz,2H),3.01(s,2H), 1.50(s,6H),1.28(t,J=7.1Hz,3H); 13 C NHR (150MHz, CDCl 3 )δ 169.34, 147.66, 142.65...

Embodiment 2

[0029] Synthesis of 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetohydrazide (compound C):

[0030]

[0031] The intermediate product B was dissolved in absolute ethanol, and hydrazine hydrate (80% mass fraction) was added dropwise under ice-bath conditions, and stirred for 5 min under ice-bath conditions. Stir and heat at 60°C for 2h, monitored by TLC. After the reaction, dichloromethane was extracted, the solvent was spin-dried, and water was added, crystals were precipitated, and the mixture was suction-filtered. Recrystallization from ethanol gave intermediate product C as white crystals with a yield of 93%. The molar ratio of intermediate product B to hydrazine hydrate is 1:2.5; MS-ESI, m / z 259.26[M+Na] + .HR-MS-EI m / z calcd for C 12 h 16 N 2 o 3 [M+H] + 236.2695,found 236.2710; 1 H NMR (600MHz, CDCl 3 )δ8.13(s,1H),6.86(d,J=7.2Hz,1H),6.77(t,J=7.7Hz,1H),6.73(d,J=8.0Hz,1H),4.65(s, 2H), 3.90(s,2H), 3.05(s,2H), 1.52(s,6H).

Embodiment 3

[0033]Preparation of (E)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N'-(4-fluorobenzylidene)acetylhydrazide :

[0034]

[0035] 2.4mmol of 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetohydrazide was dissolved in 50ml of ethanol, stirred and dissolved, then added 2.88mmol of p-fluorobenzaldehyde, oil Heat and stir the bath at 60°C for 6-8h, monitor by TLC. After the reaction is complete, filter with suction and spin-dry to obtain 0.74g of the crude product of light yellow viscous solid, which is subjected to column chromatography (V 二氯甲烷 :V 甲醇 =160:1), to obtain (E)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N'-(4-fluorophenylene Methyl) acetylhydrazide 0.54g. m.p.145.9-146.5℃, yield 90.1%, 1 H NMR (600MHz, CDCl 3 )δ9.92(s,1H),8.13(s,1H),7.63(d,J=8.4Hz,2H),7.30(d,J=8.4Hz,2H),6.84–6.79(m,1H), 6.73 (d, J=6.3Hz, 2H), 4.67 (s, 2H), 2.99 (s, 2H), 1.46 (s, 6H).

[0036] Preparation of 2-(((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)methyl)-5-(4-fluorophe...

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Abstract

The present invention provides a benzofuranol-based oxadiazole derivative represented by a formula (I) shown in the specification, and a preparation method and application thereof. In the formula, R is selected from 4-CN-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 3-F-C6H4, 3-Br-C6H4, 4-NO2-C6H4, 3-NO2-C6H4, 2-Br-C6H4, 3-CH3-C6H4, 4-CH3-C6H4, 4-OMe-C6H4, 3-OMe-C6H4, 2-OMe-C6H4, phenyl, isopropyl, cyclohexyl, styryl, furyl, thienyl or naphthyl. The compound of the invention and pharmaceutically acceptable salts thereof exhibit high inhibitory activity against weeds such as Echinochloa crusgalli without causing damage to crops, and provide a new choice for eliminating weeds.

Description

technical field [0001] The invention relates to a compound, its preparation method and application, in particular to a furanol-based oxadiazole derivative and its preparation method and application. Background technique [0002] my country is a big country in grain production and consumption in the world, and increasing grain yield per unit area is a very important way to ensure food security in our country. Weeds are one of the main factors leading to crop yield reduction. The development and large-scale application of organic chemical herbicides can greatly reduce the agricultural economic losses caused by weeds. There are more than 500 varieties of existing herbicides, but due to long-term repeated use, many weeds have developed resistance to various types and varieties of herbicides in recent years. Therefore, it is imperative to develop new herbicides. must do. [0003] 1,3,4-Oxadiazole is a five-membered heterocyclic ring containing O and N atoms, which has a wide ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D413/14A01N43/824A01P13/00
CPCC07D413/12C07D413/14A01N43/82
Inventor 李婉李胜男武世杰朱华结田胜尼冯珂曹飞李龙飞
Owner HEBEI UNIVERSITY
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