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Phloroglucinol propionyl derivative and its synthesis method and uses

A technology of phloroglucinol and propionylphloroglucinol, which is applied in the field of phloroglucinol propionyl derivatives and their synthesis, and can solve the problems of unreported biological activity testing

Inactive Publication Date: 2006-02-08
BIOLOGY INST OF SHANDONG ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report about the synthesis method and biological activity test of propionylphloroglucinol derivatives in the relevant literature

Method used

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  • Phloroglucinol propionyl derivative and its synthesis method and uses
  • Phloroglucinol propionyl derivative and its synthesis method and uses
  • Phloroglucinol propionyl derivative and its synthesis method and uses

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The molecular formula of 2,4-dipropionylphloroglucinol:

[0025]

[0026] Synthesis of 2,4-dipropionylphloroglucinol:

[0027] In the 250ml there-necked flask equipped with stirring device and reflux condenser, add 20g (0.16mol) phloroglucinol, at room temperature, under nitrogen protection, slowly add 42.9ml (0.33mol, 43.37g) propionic anhydride and 110ml ( 123.92 g) boron trifluoride-diethyl ether solution, wherein boron trifluoride is 0.87 mol, after the dropwise addition, keep the reaction temperature at 26-30°C and stir for 24 hours. After the reaction, add 400ml distilled water, stir for 5-10min, remove BF 3 , separated the reaction solution, the water layer was washed with 100ml ethyl acetate, the ester layer was combined with the reaction solution and the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with 60% ethanol / water to obtain the crude product, and after multiple recrystallizations, 2 , 4-dipropionylphlo...

Embodiment 2

[0030] The molecular formula of 2-propionyl-4-butyrylphloroglucinol:

[0031]

[0032] Synthesis of 2-propionyl-4-butyrylphloroglucinol:

[0033]In a 250ml three-neck flask equipped with a stirring device and a reflux condenser, add 5g (0.027mol) 2-propionylphloroglucinol, and under nitrogen protection, slowly add 5.4ml (0.033mol, 5.22g) butyric anhydride and 12.1 ml (13.65g) of boron trifluoride-diethyl ether solution, in which boron trifluoride is 0.096mol, and 10ml of anhydrous diethyl ether is added, and the above reactants are stirred and reacted in an ice-salt water bath for 24h. After the reaction is over, add 100ml of distilled water, stir for 5-10min, separate the reaction solution, extract the water layer with 50ml of ethyl acetate, combine the ester layer with the reaction solution, distill off the solvent under reduced pressure, and recrystallize the obtained solid with 60% ethanol / water The crude product was obtained. Crude yield was 77%. Using a developer o...

Embodiment 3

[0036] As described in Example 1, the difference is that 0.16 mol of phloroglucinol, 0.085 mol of propionic anhydride, and 0.94 mol of boron trifluoride (ether solution) were added. The crude product yield was 67.2%. The crude product was recrystallized to obtain a pure product yield of 59.2%.

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PUM

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Abstract

Disclosed is a phloroglucinol propionyl derivative, its synthesizing process and use, wherein the derivative has a general formula disclosed in the specification, wherein R1 is -CH2CH3 or -CH2CH2CH3. The compound is prepared through one step alkylation reaction at the presence of Friedel catalyst by using phloroglucinol or 2-propionyl phloroglucinol as raw material. The compound provided by the invention can be used for the prevention and treatment of plant diseases including cotton soreshin, Rhizoctonia cerealis, chloranemia, apple ring spot, grape botrytis bunch rot and blight, wilt, Leuconostoc, black rot, and drechslera teres (sacc.) shoemaker.

Description

(1) Technical field [0001] The invention relates to a phloroglucinol propionyl derivative and its synthesis method and application, belonging to the technical field of biological antibiotic phloroglucinol propionyl derivatives. (2) Background technology [0002] 2,4-Diacetylphloroglucinol is a polyketide antibiotic with broad-spectrum bactericidal effect produced by Pseudomonas fluorescens. It has strong killing activity against bacteria, fungi, viruses and worms, and is also effective against higher Plants have certain toxicity, see patent "Pseudomonas fluorescens, bacterial agent for disease prevention and preservation of fruits and vegetables and its production process", announcement number 1403568; Bender et al., polyketide antibiotics produced by Pseudomonas fluorescens , Acta Phytopathol, Volume 37 175-196, 1999 (Bender, C.L.et.al.1999.Polyketide production by plant-associated Pseudomonas.Ann.Rev.Phytopathol.37:175-196); Wang Ye, producing antibiotics 2, Isolation and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/76A01N35/04
Inventor 孔学高永超杨合同王加宁陈贯虹聂玉敏
Owner BIOLOGY INST OF SHANDONG ACAD OF SCI
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