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4-substituted alpha-pyrone derivative as well as preparation method and application thereof

A pyrone and methyl technology, which is applied in the field of 4-substituted alpha-pyranone derivatives and their preparation, can solve the problem that 6-pentyl-dihydropyran-2-one cannot be stably synthesized and inoculants cannot be Stable performance of disease control activity, less types of pyrone derivatives, etc., to achieve the effects of easy industrial production, low cost, and high bacteriostatic rate

Active Publication Date: 2015-04-22
ECOLOGY INST SHANDONG ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 6-pentyl-2H-pyran-2-one is mainly synthesized in soil by using Trichoderma, but because the live bacterial agent is easy to die in the form of preparation, and the growth and reproduction of the bacterial body in the soil is subject to various Due to the influence of physical, chemical and ecological conditions, 6-pentyl-dihydropyran-2-one cannot be stably synthesized at the plant rhizosphere and other action sites, so the bacterial agent often cannot stably show the control activity against diseases
At present, there are few types of pyrone derivatives with pathogenic fungal antibacterial activity reported at home and abroad, and there is a lot of room for research on this type of active compounds

Method used

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  • 4-substituted alpha-pyrone derivative as well as preparation method and application thereof
  • 4-substituted alpha-pyrone derivative as well as preparation method and application thereof
  • 4-substituted alpha-pyrone derivative as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Example 1 Synthesis of 6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione (Formula 2)

[0045] Suspend 52 grams of maleic acid powder in 60 milliliters of acetic anhydride, cool the system with water, add 1.5 milliliters of concentrated sulfuric acid while stirring, slowly add 40 milliliters of acetone to the above solution, and keep the temperature at 20-25 degrees (cooling is required). After reacting for 2 hours, the reaction bottle was placed in a refrigerator at 3-5°C overnight, filtered with suction, the crystals were fully washed with ice water three times, and dried to obtain 35 g of crude compound 1. The compound was dissolved in 70 ml of acetone, and an appropriate amount of water (about 140 ml) was added for crystallization to obtain 25 g of pure 6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione, mp. 95-96°C. The structural formula is as follows:

[0046]

Embodiment 24

[0047] Synthesis of embodiment 24-hydroxyl-6-methyl-2-pyrone (formula 3)

[0048] 14.4 g (0.1 mol) of 6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione prepared by the method in Example 1, 35 milliliters of dichloromethane and 15 milliliters of chlorobenzene Place in a reaction bottle, cool to below 5°C under stirring, add 10.1g (0.1mol) triethylamine and 10.1g (0.12mol) diketene in turn, slowly warm up to room temperature after addition, and continue stirring for 2 hours. The reaction solution was washed with 5% hydrochloric acid at 3-8°C, dried over anhydrous sodium sulfate and filtered to remove most of the dichloromethane. The remaining solution was heated to reflux for 2 hours, and yellow crystals precipitated out. Cool to crystallize, filter with suction and wash the crystals with a small amount of ether, and dry to give 10.1 g of 4-hydroxy-6-methyl-2-pyrone, yield 82%, mp.188~189°C. 1H NMR (CDCl 3 ) chemical shift: 2.245 (s, 3H, CH 3 ),5.484(d,1H,CH),5.885(s,1H,CH),1.557(s...

Embodiment 3

[0050] Example 3 Synthesis of 4-methoxyl-6-methyl-2-pyrone (5a)

[0051] Add 4-hydroxy-6-methyl-2-pyrone 3 (0.8g, 0.0063mol) solid, 0.55ml of bromomethane (0.0095mol) solution and 2ml of triethylamine (0.019mol) solution to a 50ml round bottom Add about 20ml of acetonitrile solution into the flask, stir to dissolve, and react in an oil bath at 40°C for 2 hours. Most of the solvent was removed by a rotary evaporator, and the product 4-methoxy-6-methyl-2-pyrone was obtained by direct column chromatography separation. The mobile phase ratio is about E:P=1:5, and it is a single fluorescent point under the ultraviolet lamp, with a small amount of raw material remaining at the origin (basically no fluorescence). Remove the treatment solvent, the product is a solid, the yield is about 50-70%, mp.88-89 ° C. H-NMR (300MHz, CDCl 3 ):2.205 (s,3H,CH 3 ), 3.790 (s,3H,CH 3 ),

[0052] 5.407(d,1H,CH),5.774(q,1H,CH).

[0053] HR-MS (ESI) m / z: 141.0553 (M+H + ,100%). The structural for...

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Abstract

The invention relates to a 4-substituted alpha-pyrone derivative as well as a preparation method and an application thereof. The 4-substituted alpha-pyrone derivative is expressed as general formula (I), wherein R represents OH, CH3O, CH3CH2O, CH3(CH2)3O, Cl, CH3(CH2)2NH, CH3(CH2)3NH or Ar. The method further relates to the preparation method or the application of the compound. The 4-substituted alpha-pyrone derivative disclosed by the invention has a high bacterium inhibiting rate on rhizoctonia solani and fusariummoniliforme sheld, and has a remarkable bioactivity.

Description

technical field [0001] The invention relates to a 4-substituted α-pyrone derivative and its preparation method and application, belonging to the technical field of agricultural fungicides. Background technique [0002] α-Pyrone is a kind of substances with coconut fragrance produced by Trichoderma viride, Trichoderma harzianum, Trichoderma korningen and other fungi, which can be used as antibiotics, antimycotics, cytotoxins, neurotoxins, phytotoxins, etc. Among them, 6-pentyl-2H-pyran-2-one (6PP) has good inhibitory effect on Sclerotium rolfsii Saccardo, Rhizoctonia bataticola, Macrophomina phaseolina, Botrytis cinerea and other plant pathogenic bacteria. Chen Kai et al. used the hyphae rate method to measure the inhibitory effect of 5,6-dihydro-6-pentyl-pyran-2-one on 11 kinds of plant pathogenic fungi at a concentration of 20 μg / ml, and all showed good results. Control effect (Chen Kai, Li Jishun, Yang Contract, et al. Control effect of 0.2% α-pyrone WP on plant pathogeni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/38C07D405/04A01N43/16A01N43/40A01P3/00
Inventor 孔学陈贯虹王加宁郑立稳黄玉杰
Owner ECOLOGY INST SHANDONG ACAD OF SCI
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