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Pentadienone compound containing triazine, and preparation method and application of pentadienone compound

A kind of ketone compound, pentadiene technology, applied in 1 field

Active Publication Date: 2019-08-02
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, there are no related reports on introducing triazine into the structure of 1,4-pentadien-3-one and testing the antibacterial properties

Method used

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  • Pentadienone compound containing triazine, and preparation method and application of pentadienone compound
  • Pentadienone compound containing triazine, and preparation method and application of pentadienone compound
  • Pentadienone compound containing triazine, and preparation method and application of pentadienone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] (1E,4E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-5-(2-thiophene )-5-substituted-1,4-pentadien-3-one (target compound A1):

[0078]

[0079] The preparation method comprises the following steps:

[0080] (1) Preparation of 5,6-diphenyl-1,2,4-triazine-3-mercaptool (intermediate 1):

[0081] Benzil (1.5g) and 35mL of glacial acetic acid were added to a 100mL three-necked flask, and then thiosemicarbazide (0.65g) was dissolved in 25mL of hot water, and the mixed system was added to the three-necked flask. Stir at ℃ for 4 h, and after the reaction is completed, filter while heating to obtain a yellow solid with a yield of 78%.

[0082] (2) Preparation of 4-(hydroxyphenyl)-3-buten-2-one (intermediate 2):

[0083] 4-Hydroxybenzaldehyde (6.1g) is added in the acetone of 60mL, after stirring for about 15min, after ice-bathing the reaction system for about 30min, add about 100mL of 5% NaOH solution in the system, after the dropwise addition is complete...

Embodiment 2

[0091] (1E, 4E)-1-(2-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-5-(4-chloro Phenyl)-1,4-pentadien-3-one (target compound A2):

[0092]

[0093] The target compound A2 was prepared by selecting corresponding raw materials in the steps similar to Example 1, and the yield was 56%.

Embodiment 3

[0095] (1E, 4E)-1-(2-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-5-(4-nitro phenyl)-1,4-pentadien-3-one (target compound A3):

[0096]

[0097] The target compound A3 was prepared by selecting corresponding raw materials according to the steps similar to Example 1, and the yield was 35%.

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PUM

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Abstract

The invention relates to a pentadienone compound containing triazine, and a preparation method and an application of the pentadienone compound. The compound is shown as formula A as shown in the specification. X selected from O; R is phenyl, substituted phenyl or substituted heterocyclyl; R1 is a hydrogen atom or methoxyl; and R2 is phenyl, substituted phenyl or C1-C6 alkyl. The compound has a better prevention and control effect on pseudomonas solanacearum, xanthomonas citri and xanthomonas campestris pv. oryzae.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a triazine-containing 1,4-pentadiene-3-one derivative, and also to the triazine-containing 1,4-pentadiene-3- A preparation method of ketone derivatives, and the application of the triazine-containing 1,4-pentadien-3-one derivatives in antibacterial activity. Background technique [0002] Natural active molecules and their derivatives have the characteristics of unique structure, novel mode of action, low toxicity to humans and animals, and environmental friendliness, which play a decisive role in the discovery of pesticide lead compounds. Curcumin, a polyphenolic compound derived from turmeric, is widely used as a spice, food preservative, monosodium glutamate, and dye. 1,4-pentadienone compound, as an important curcumin derivative, has broad-spectrum biological activities such as insecticidal, antibacterial, anti-plant virus, anti-cancer, anti-inflammatory and anti-ox...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D253/07C07D401/12C07D405/12A01N43/707A01P1/00A01P3/00
CPCC07D409/12C07D253/07C07D401/12C07D405/12A01N43/707
Inventor 薛伟汤旭陈梅贺军苏时军吴佳祥柳立伟贺鸣王俊
Owner GUIZHOU UNIV
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