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1,4-Pentadiene-3-ketone derivative with thiophene sulphonate and preparation method and application of derivative

A technology of thiophene sulfonate and pentadiene, which is applied in the direction of botany equipment and methods, chemicals for biological control, applications, etc., can solve problems that have not been seen, and achieve good inhibitory activity, high yield, Post-processing simple effects

Active Publication Date: 2019-06-28
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2011, Wu Qin introduced the benzenesulfonate group into 1,4-pentadien-3-one and tested the anti-tumor activity, but did not work on the pesticide activity
[0012] In summary, compounds containing 1,4-pentadien-3-one and thiophene sulfonate have good biological activity, but there is no introduction of thiophene sulfonate into 1,4-pentadiene -3-ketone structure, and test related reports on the activity of inhibiting plant bacteria

Method used

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  • 1,4-Pentadiene-3-ketone derivative with thiophene sulphonate and preparation method and application of derivative
  • 1,4-Pentadiene-3-ketone derivative with thiophene sulphonate and preparation method and application of derivative
  • 1,4-Pentadiene-3-ketone derivative with thiophene sulphonate and preparation method and application of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of (4-((1E,4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenylthiophene-2-sulfonate (compound number is A1), Include the following steps:

[0026] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: 4-hydroxybenzaldehyde (5.0g) was added to 50mL of acetone, after stirring for about 20min, the reaction system was ice-bathed for about After 30 min, about 80 mL of 5% NaOH solution was added to the system. After the dropwise addition was completed, the ice bath was removed, and stirred at room temperature for about 24 h. After the reaction is over, transfer the system to a 500mL beaker and add an appropriate amount of ice water, and then use 5% dilute hydrochloric acid solution to adjust the pH of the system to about 5-6. After a large amount of yellow solids precipitate, extract the solids, and finally use ethanol to / water system recrystallized to obtain a yellow solid with a yield of 70%.

[0027] (2) Synthesis of 1-(4-phenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: ...

Embodiment 2

[0030] Synthesis of (4-((1E,4E)-5-(4-chlorophenyl)-3-oxopent-1,4-dien-1-yl)phenylthiophene-2-sulfonate (compound numbered A2), including the following steps:

[0031] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0032] (2) Synthesis of 1-(4-(4-chlorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, The difference is that 4-chlorobenzaldehyde is used as raw material.

[0033] (3) (4-((1E,4E)-5-(4-chlorophenyl)-3-oxopent-1,4-dien-1-yl)phenylthiophene-2-sulfonate Synthesis: as in step (3) of Example 1.

Embodiment 3

[0035] Synthesis of (4-((1E,4E)-5-(2-chlorophenyl)-3-oxopent-1,4-dien-1-yl)phenylthiophene-2-sulfonate (compound numbered A3), including the following steps:

[0036] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0037] (2) Synthesis of 1-(4-(2-chlorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, The difference is that 2-chlorobenzaldehyde is used as raw material.

[0038] (3) (4-((1E,4E)-5-(2-chlorophenyl)-3-oxopent-1,4-dien-1-yl)phenylthiophene-2-sulfonate Synthesis: as in step (3) of Example 1.

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Abstract

The invention discloses a 1,4-pentadiene-3-ketone derivative with thiophene sulphonate. The derivative is characterized in that the general formula of the derivative is shown in the following formula,wherein R is substituted phenyl or a substituted aromatic heterocyclic group. According to the derivative, 1-(4-hydroxy phenyl)-5-(substituted aryl)-1,4-pentadiene-3-ketone and thiophene sulphonate with good biological activity react to generate the 1,4-pentadiene-3-ketone derivative with the thiophene sulphonate, and when the concentration is 100 mcg / mL and 50 mcg / mL, the plant bacterium inhibition activity of a target compound is measured. It is proved through a bacterium inhibition activity testing result that at the experiment testing concentration, most compounds have good inhibition activity on xanthomonas oryzae, ralstonia solanacearum and xanthomonas citri and can be applied to preparation of an agent for inhibiting plant bacteria.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a 1,4-pentadien-3-one derivative containing thiophene sulfonate, and also to the 1,4-pentanediene derivative containing thiophene sulfonate The preparation method of en-3-one derivatives and the application of the 1,4-pentadien-3-one derivatives containing thiophene sulfonate in inhibiting the activity of plant bacteria and viruses. Background technique [0002] Natural products and their biomimetic pesticides are environmentally friendly, have unique action sites and high selectivity, and play an increasingly important role in the control of plant diseases. Curcumin, a polyphenolic compound derived from turmeric, is widely used as a spice, food preservative, monosodium glutamate, and dye. 1,4-Pentadien-3-one compound, as an important curcumin derivative, has broad-spectrum biological properties such as insecticidal, antibacterial, antiviral, anticancer, anti-inflammat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/34C07D409/12A01N43/10A01N43/40A01P1/00
Inventor 薛伟郭涛夏榕娇苏时军贺军陈梅蒋仕春汤旭陈英
Owner GUIZHOU UNIV
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