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4-bromine-2-picolinamide compound containing diphenyl ether structure

A technology of pyridine amides and diphenyl ethers, applied in the field of new compounds, can solve the problems of reduced insecticidal and bacteriostatic effect, large chemical pollution and high toxicity and side effects, and achieves the effects of low toxicity, simple preparation method and high yield

Pending Publication Date: 2018-11-06
湖南博隽生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the above-mentioned compounds have relatively large chemical pollution and high toxicity during the application process, and may remain on the surface of plant leaves and stems
Due to long-term use, many insects have also undergone certain evolutionary variations, and the insecticidal and antibacterial effects on new varieties of diseases and insect pests have been significantly reduced. Therefore, it is necessary to find new compounds with low toxicity, green environmental protection, and dual functions of sterilization and deinsectization. increase crop yields

Method used

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  • 4-bromine-2-picolinamide compound containing diphenyl ether structure
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  • 4-bromine-2-picolinamide compound containing diphenyl ether structure

Examples

Experimental program
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Effect test

Embodiment 1

[0032] A preparation method of a 4-bromo-2-pyridine amide compound containing a diphenyl ether structure, comprising the steps of:

[0033] (1) Dissolve 2-phenoxynitrobenzene (0.215g, 1.0mmol) in 30ml ethanol, add 80% hydrazine hydrate (0.068g, 1.0mmol) under stirring, heat up to reflux, react for 6.0 hours, cool, and filter , to obtain a brown solid, the intermediate 2-phenoxyaniline, with a yield of 90%.

[0034] (2) Dissolve 2-phenoxyaniline (0.185g, 1.0mmol) and 4-bromo-2-pyridinecarboxylic acid (0.202g, 1.0mmol) generated in step (1) in 25ml of dichloromethane, add three Ethylamine (0.202g, 2.0mmol), under the condition of the catalyst DMAP, then added EDCI (0.287g, 1.5mmol), HOBt (0.20g, 1.5mmol), reacted at 25°C for 6 hours, TLC detected that the reaction was complete, and the reaction solution Washed three times with water, washed once with saturated brine, dried the organic layer with anhydrous sodium sulfate, desolvated, the crude product was column chromatographed ...

Embodiment 2

[0037] A preparation method of a 4-bromo-2-pyridine amide compound containing a diphenyl ether structure, comprising the steps of:

[0038] (1) Dissolve 2-phenoxynitrobenzene (0.246g, 1.0mmol) in 30ml ethanol, add 80% hydrazine hydrate (0.073g, 1.0mmol) under stirring, heat up to reflux, react for 6.5 hours, cool, and filter , to obtain a brown solid, the intermediate 2-phenoxyaniline, with a yield of 92%.

[0039] (2) Under nitrogen protection, 25ml of 4-bromo-2-pyridinecarboxylic acid (0.214g, 1.0mmol) was dissolved in acetonitrile, and 2-phenoxyaniline (0.196g, 1.0mmol) and DIEA (0.389g , 3.0mmol), the temperature was lowered to below 10°C, the temperature was controlled at 0-10°C, and HBTU (0.493g, 1.30mmmol) was added rapidly, and the temperature was raised to room temperature for 8.0 hours. TLC detected that the reaction was complete and the solution was removed. The crude product was obtained by flash column chromatography as a dark green solid, namely 4-bromo-2-pyridi...

Embodiment 3

[0042] A preparation method of a 4-bromo-2-pyridine amide compound containing a diphenyl ether structure, comprising the steps of:

[0043] (1) Dissolve 2-phenoxynitrobenzene (0.214g, 1.0mmol) in 30ml ethanol, add 80% hydrazine hydrate (0.054g, 1.0mmol) under stirring, heat up to reflux, react for 7.0 hours, cool and filter , to obtain a brown solid, the intermediate 2-phenoxyaniline, with a yield of 91%.

[0044](2) Dissolve 32ml of 2-phenoxyaniline (0.174g, 1.0mmol) and 4-bromo-2-pyridinecarboxylic acid (0.232g, 1.0mmol) in dichloromethane, and quickly add DCC (0.206g, 1.0mmol) and DMAP (0.012g, 0.10mmol), stirred and reacted at room temperature for 8.0 hours. After the reaction was completed, washed twice with 30ml of saturated saline, once with 30ml of water, dried over sodium sulfate, and precipitated. The crude product was obtained by flash column chromatography. Green solid, namely 4-bromo-2-pyridine amide compound containing diphenyl ether structure, m.p.63-65°C, yiel...

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Abstract

The invention relates to a 4-bromine-2-picolinamide compound containing a diphenyl ether structure. A target compound is synthesized by taking 2-phenoxyaniline and 4-bromine-2-picolinic acid as raw materials under the condition of alkali, a condensing agent and an organic solvent through one-step reaction. The compound has high bactericidal activity and herbicidal activity, the preparation methodis simple and convenient, and the yield is high.

Description

technical field [0001] The present invention relates to a class of novel compounds and uses thereof, in particular to 4-bromo-2-pyridine amide compounds containing a diphenyl ether structure and their application in the preparation of fungicides and herbicides. Background technique [0002] Pyridinamide compounds have a wide range of pharmaceutical and pesticide activities. Since the early 21st century, BASF has launched the first registered succinate dehydrogenase inhibitor (SDHI) fungicide in 2002. Boscalid is a broad-spectrum, internal Absorbing fungicides, which control diseases caused by Ascomycetes and Deuteromycetes on fruits, vegetables and other crops, had sales of $581 million in 2011. [0003] [0004] In recent years, boscalid derivatives have been reported in literature, and the series of compounds A reported by Hou Taiping have good inhibitory activity against plant pathogens. [0005] [0006] Fluonicamid (flonicamid) B is a new type of pyridine amide i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81A01N43/40A01P13/00A01P3/00
CPCA01N43/40C07D213/81
Inventor 李丽娟朱露晶万迎春
Owner 湖南博隽生物医药有限公司
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