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Compound 2-hydroxyl-3-fluoro-5-nitro-1-phenylbutanone and its preparation method and agricultural biological activity

A technology for phenylbutanone and compounds, which is applied in the preparation of nitro compounds, botanical equipment and methods, and chemicals for biological control, etc., can solve the problems of low utilization rate of mixed acid, low atom utilization rate, and increased cost. , to achieve the effect of few reaction steps, high inhibitory effect, and efficient bactericidal activity

Inactive Publication Date: 2018-01-02
QINGDAO AGRI UNIV
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  • Summary
  • 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-hydroxyl-3-fluoro-5-nitro-1-phenylbutanone and its preparation method and agricultural biological activity
  • Compound 2-hydroxyl-3-fluoro-5-nitro-1-phenylbutanone and its preparation method and agricultural biological activity
  • Compound 2-hydroxyl-3-fluoro-5-nitro-1-phenylbutanone and its preparation method and agricultural biological activity

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

A compound 2 种 hydroxyl ‑3‑3‑5‑5‑ nitrate ‑1‑1‑ phenobarne and its preparation methods and agricultural biological activity.Add nitric acid, ethylamine and methanol to the reactor. After stirring for a period of time, cool down the reactor to 0 to 20 ° C, add 2‑ hydroxyl ‑3‑l fluorinel phenobarne, and add water to the reaction mixture for a period of timeThen add acetate to extract multiple times to obtain a target compound from the organic phase.This compound has a high inhibitory effect on apple rot, cabbage gray mold, citrus anthrax, cotton wither, and wheat complication.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/45C07C201/08A01N33/22A01P3/00
Inventor 杜春华
Owner QINGDAO AGRI UNIV
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