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Phloroglucinol acetyl derivative and its synthesis method and uses

A kind of phloroglucinol acetyl, base phloroglucinol technology, applied in the field of phloroglucinol acetyl derivatives and synthesis thereof, can solve problems such as no report on biological activity test

Inactive Publication Date: 2007-02-14
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 on the synthesis method and biological activity test of the product modified by diacetylphloroglucinol in the relevant literature

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2-Acetyl-4-propionylphloroglucinol, the molecular formula is:

[0018]

[0019] Synthesis of 2-acetyl-4-propionylphloroglucinol:

[0020] In a 250ml three-neck flask equipped with a stirring device and a reflux condenser, add 10g (0.060mol) 2-acetylphloroglucinol, and slowly add 9.2ml (0.071mol, 9.30g) propionic anhydride dropwise under nitrogen protection, Add 22.6ml (25.5g) boron trifluoride-diethyl ether solution dropwise under stirring conditions, including 0.18mol of boron trifluoride. After the dropwise addition, add 10ml of anhydrous diethyl ether. The reaction system is stirred and reacted in an ice-water bath for 24h . After the reaction, 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 and the reaction solution, distill off the solvent under reduced pressure, and recrystallize the obtained solid with 60% ethanol / water The crude product was obtained, ...

Embodiment 2

[0023] 2-Acetyl-4-butyrylphloroglucinol, the molecular formula is:

[0024]

[0025] Synthesis of 2-acetyl-4-butyrylphloroglucinol:

[0026] In a 250ml three-necked flask equipped with a stirring device and a reflux condenser, add 5g (0.03mol) of 2-acetylphloroglucinol, and place the three-necked flask in an ice-salt bath so that the reaction temperature is not higher than 5°C, slowly Add 5.8ml (0.036mol, 5.65g) of butyric anhydride, then add 13.1ml (14.79g) of boron trifluoride-ether solution, in which boron trifluoride is 0.104mol, after the dropwise addition, add 10ml of anhydrous ether to make the reaction The substance was completely dissolved, and the reaction temperature was kept at -2-2°C and stirred for 24 hours. After the reaction, add 15ml of distilled water, stir vigorously, then add 30ml of 1:1 methanol / water, carefully add 10gK 2 CO 3 , to make the solution pH = 7-8, then add 10ml of 1:1 methanol / water, stir at room temperature for 6h, add 10% hydrochloric ...

Embodiment 3

[0029] As described in Example 1, the difference is that 0.060 mol of 2-acetylphloroglucinol, 0.085 mol of propionic anhydride, and 0.24 mol of boron trifluoride (diethyl ether solution) were added. The crude product yield was 82.4%, and the crude product was separated to obtain a pure product yield of 68%.

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PUM

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Abstract

Disclosed is phloroglucinol acetyl derivative and its synthesis method and uses, wherein the derivative has the 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-acetyl 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 acetyl derivative and its synthesis method and application, belonging to the technical field of biological antibiotic phloroglucinol acetyl 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 the 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, Vol. 37, 175-196, 1999 (Bender, C.L., et.al.1999. Polyketide production by plant-associated Pseudomonas. Ann. Rev. Phytopathol. 37: 175-196); Wang Ye, Antibiotic Production 2, Isolation ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/78A01N35/04
Inventor 高永超孔学杨合同王加宁陈贯虹聂玉敏
Owner BIOLOGY INST OF SHANDONG ACAD OF SCI
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