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Compound 2-hydroxy-3-fluoro-5-nitro-1-phenyl butanone and preparation method and agricultural biological activity thereof

A technology of phenylbutanone and compounds, which is applied to the preparation of nitro compounds, botany equipment and methods, chemicals for biological control, etc., can solve the problems of low atom utilization rate, low mixed acid usage rate, poor selectivity, etc. , to achieve high inhibitory effect, less reaction steps and simple operation

Inactive Publication Date: 2015-02-04
QINGDAO AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The nitration reaction generally uses mixed acids such as nitric acid and sulfuric acid as the nitration reagent, which has poor selectivity, low utilization rate of atoms, low utilization rate of mixed acid, and post-processing will increase the cost

Method used

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  • Compound 2-hydroxy-3-fluoro-5-nitro-1-phenyl butanone and preparation method and agricultural biological activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1: Weigh 0.196 g (0.005629 mol) of fuming nitric acid and 0.583 g of acetic anhydride in a reaction flask, stir at 30°C for 1 h, transfer the reaction flask to an ice bath, and add in 5 batches within 1 hour 2-Hydroxy-3-fluoro-1-phenylbutanone 0.512 g. During the reaction process, the reaction progress was judged by thin-layer chromatography. After the reaction was completed, add distilled water and ethyl acetate to the reaction bottle, separate the liquids, extract twice with ethyl acetate, combine the organic phases, remove water with anhydrous sodium sulfate, and evaporate under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography. Pale yellow crystals were obtained with a yield of 67%.

Embodiment 2

[0013] Example 2: Weigh 0.196 g (0.005629 mol) of fuming nitric acid and 0.583 g of acetic anhydride in a reaction flask, stir at 30°C for 1 h, transfer the flask to a 20°C water bath, and add in 5 batches within 1 hour 2-Hydroxy-3-fluoro-1-phenylbutanone 0.512 g. During the reaction process, the reaction progress was judged by thin-layer chromatography. After the reaction was completed, add distilled water and ethyl acetate to the reaction bottle, separate the liquids, extract twice with ethyl acetate, combine the organic phases, remove water with anhydrous sodium sulfate, and evaporate under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography. Pale yellow crystals were obtained with a yield of 59%.

[0014] Characterization of the target compound 2-hydroxy-3-fluoro-5-nitro-1-phenylbutanone

[0015] Mass spectrometry analysis showed that the molecular weight of the obtained compound was 227.2, which was consistent with the the...

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Abstract

Disclosed are a compound 2-hydroxy-3-fluoro-5-nitro-1-phenyl butanone and a preparation method and an agricultural biological activity thereof. The preparation method comprises the steps: adding nitric acid, acetic anhydride and methanol in a reactor, after stirring for a period of time, cooling the reaction liquid to 0-20 DEG C, adding 2-hydroxy-3-fluoro-1-phenyl butanone, carrying out a reaction for a period of time, adding water into the reaction mixture, then adding ethyl acetate, extracting for multiple times, and thus obtaining the target compound from an organic phase. The compound has relatively high inhibitory effects on apple rot, Chinese cabbage grey mould, citrus anthrax, cotton fusarium wilt, wheat take-all and other plant pathogenic bacteria.

Description

technical field [0001] The invention relates to compound 2-hydroxy-3-fluoro-5-nitro-1-phenylbutanone, its preparation method and agricultural biological activity, and specifically relates to the fields of organic compounds, organic synthesis and agricultural sterilization. Background technique [0002] Phenolic compounds are important secondary metabolites produced by plants such as ginkgo, onion, bitter bark vine, Scutellaria barbata, rhubarb, etc. They often show biological activities such as antibacterial, insecticidal, and herbicidal, which provide a forerunner for the development of botanical pesticides compound. We isolated several carbonyl-containing phenolic compounds (ie, hydroxyaromatic ketones) from Scutellaria barbata, and found that they had certain bactericidal effects. We planned to modify these compounds by biomimetic synthesis. Due to the large electronegativity and small radius of the fluorine atom, the bond energy of the formed C-F bond is much larger tha...

Claims

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Application Information

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IPC IPC(8): C07C205/45C07C201/08A01N33/22A01P3/00
Inventor 杜春华
Owner QINGDAO AGRI UNIV
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