Fluoroquinolone amino derivatives and use thereof in prevention and control of citrus diseases

An amino and alkyl technology, applied in the field of fluoroquinolone amino derivatives, can solve problems such as lack of research and accumulation, lack of technical reserves and systematic research, and no effective and reliable control technology

Active Publication Date: 2018-03-23
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Citrus brown spot disease is a new disease in my country, and there is a lack of corresponding technical reserves and systematic research, especially the lack of research and accumulation on the types of p...

Method used

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  • Fluoroquinolone amino derivatives and use thereof in prevention and control of citrus diseases
  • Fluoroquinolone amino derivatives and use thereof in prevention and control of citrus diseases
  • Fluoroquinolone amino derivatives and use thereof in prevention and control of citrus diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add raw materials gatifloxacin (GAT) 1mmol, NaHCO 3 2.5mmol, DCM 5mL, add dropwise a mixed solution of chloroacetyl chloride 2mmol and DCM 2mL under ice-cooling. After dropping, the reaction was continuously stirred under ice bath, and the reaction progress was monitored by TLC. After the reaction, add a little ice-cold saturated NaCl solution to dissolve the solid, adjust the pH to 4-5 with ice-cold 2N HCl solution, stir evenly, transfer to a separatory funnel for liquid separation, extract twice with DCM, combine the organic phases, and wash with saturated NaCl solution. Water Na 2 SO 4 Dry and remove the solvent by rotary evaporation. The pure product was obtained by recrystallization or column chromatography, dried and weighed to obtain the product, [M+H] + 453.1342.

Embodiment 2

[0059] Into a 100mL round bottom flask, add raw materials GAT 1mmol, NaHCO 3 2.5mmol, DCM 5mL, add dropwise a mixed solution of chloropropionyl chloride 2mmol and DCM 2mL under ice-cooling. After dropping, the reaction was continuously stirred under ice bath, and the reaction progress was monitored by TLC. After the reaction, add a little ice-cold saturated NaCl solution to dissolve the solid, adjust the pH to 4-5 with ice-cold 2N HCl solution, stir evenly, transfer to a separatory funnel for liquid separation, extract twice with DCM, combine the organic phases, and wash with saturated NaCl solution. Water Na 2 SO 4 Dry and remove the solvent by rotary evaporation. The pure product was obtained by recrystallization or column chromatography, dried and weighed to obtain the product, [M+H] + 467.1453.

Embodiment 3

[0061] Into a 100mL round bottom flask, add raw materials GAT 1mmol, NaHCO 3 2.5mmol, DCM 4mL, add dropwise a mixed solution of 4-chlorobutyryl chloride 2.5mmol and 2mL DCM under ice-cooling. After dropping, the reaction was continuously stirred under ice bath, and the reaction progress was monitored by TLC. After the reaction, add a little ice-cold saturated NaCl solution to dissolve the solid, adjust the pH to 4-5 with ice-cold 2N HCl solution, stir evenly, transfer to a separatory funnel for liquid separation, extract twice with DCM, combine the organic phases, and wash with saturated NaCl solution. Water Na 2 SO 4 Dry and remove the solvent by rotary evaporation. Recrystallized to obtain pure product, dried, weighed to obtain product, [M+H] + 481.1679.

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PUM

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Abstract

Citrus canker and brown spot are common diseases of citrus. At present, few drugs are available to prevent and control the two diseases and have certain defects. Amino groups at the 7th positions of fluoroquinolone drugs are linked with an active fragment by means of a connecting structure so as to obtain compounds shown in a formula I or a formula II. Experiments prove that the compounds providedby the invention have effects of preventing and controlling the citrus canker and the brown spot and have very good application prospect.

Description

technical field [0001] The invention relates to fluoroquinolone amino derivatives and uses thereof, in particular to the use of fluoroquinolone amino derivatives in preventing and treating citrus canker and citrus brown spot. Background technique [0002] As the world's largest fruit, citrus has a dominant position in the whole fruit tree industry due to its output and economic value. In recent years, my country's citrus industry has developed rapidly and has gradually become an important pillar industry to promote the development of the country's rural economy and ensure farmers' income. However, citrus fruits are often susceptible to infection by diseases and insect pests during the process of growth, storage and transportation, and produce and accumulate various biotoxins, which seriously affect the yield and quality of citrus, and greatly reduce the economic value of citrus. [0003] Citrus canker is a widespread bacterial disease caused by Xanthomonas axonopodis pv. H...

Claims

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Application Information

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IPC IPC(8): C07D215/56C07D401/12C07D401/04C07D401/14C07D417/14A01N43/60A01N43/713A01N47/34A01N43/653A01N43/56A01N43/78A01N43/824A01N43/52A01P1/00A01P3/00
CPCA01N43/52A01N43/56A01N43/60A01N43/653A01N43/713A01N43/78A01N43/82A01N47/34C07D215/56C07D401/04C07D401/12C07D401/14C07D417/14
Inventor 胡军华杨大成范莉龙艳玲冯计周黄敏王帆刘文刘洁陈菲菲刘晋宇张泽朝杨真张金坤谌阳陈思雅
Owner SOUTHWEST UNIVERSITY
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