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1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof

A phosphite, pentadiene technology, applied in botanical equipment and methods, chemicals for biological control, applications, etc., to achieve good inhibitory activity

Active Publication Date: 2018-11-23
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In summary, compounds containing 1,4-pentadien-3-one and phosphite have good biological activity, but there is no introduction of phosphite into the structure of pentadienone, and the test for inhibition Related reports on the activity of plant bacteria

Method used

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  • 1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof
  • 1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof
  • 1,4-pentadiene-3-one derivative containing phosphite ester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of (4-((1E,4E)-5-(3-nitrophenyl)-3-oxopent-1,4-dien-1-yl)phenyl) diethyl phosphate (Compound No. is A1), including the following steps:

[0032](1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: 4-hydroxybenzaldehyde (6.1g) was added to 60mL of acetone, after stirring for about 15min, the reaction system was ice-bathed for about After 30 min, add about 100 mL of 5% NaOH solution to the system, after the dropwise addition is complete, remove the ice bath, and stir 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 68%.

[0033] (2) Synthesis of 1-(3-nitrophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: 4-(hyd...

Embodiment 2

[0036] Synthesis of dimethyl(4-((1E,4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenyl)phosphite (compound number A2), Include the following steps:

[0037] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0038] (2) Synthesis of 1-(4-phenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is that benzene formaldehyde as raw material.

[0039] (3) Synthesis of dimethyl (4-((1E, 4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl) phenyl) phosphite: as in the examples 1 Step (3). The difference is that 1-(4-phenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one and H-methyl phosphite are used as raw materials.

Embodiment 3

[0041] Synthesis of diethyl (4-((1E,4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenyl)phosphate (compound number A3), including the following step:

[0042] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0043] (2) Synthesis of 1-(phenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is that benzaldehyde is used as raw material.

[0044] (3) Synthesis of (4-((1E, 4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenyl) diethyl phosphate: as in Example 1 (3) step. The difference is that 1-(4-phenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one and H-ethyl phosphite are used as raw materials.

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Abstract

The invention discloses a 1,4-pentadiene-3-one derivative containing phosphite ester as well as a preparation method and application thereof. According to the 1,4-pentadiene-3-one derivative containing phosphite ester, the general formula (I) of the 1,4-pentadiene-3-one derivative containing phosphite ester is as shown in the formula (I) in the specification, wherein R1 is a phenyl group, a substituted phenyl group or a substituted aromatic heterocyclic group, R2 is an alkyl group of C1-C6, the substituted phenyl group of the R1 is one or more methoxy group, nitro group, methyl group, trifluoromethyl group or halogen atom contained in ortho-, meta- and para- on a benzene ring or two positions of the ortho-, meta- and para- on the benzene ring, and the substituted aromatic heterocyclic group of R1 is a furan group, a pyridyl group, a thienyl group, a pyrrolyl group, a thiazolyl group, a 2-chloropyridine group or a 2-chlorothiazolyl group. The 1,4-pentadiene-3-one derivative as well as the preparation method and application thereof have the advantages that the activity of plant bacteria can be inhibited, the raw materials are easily available, the reaction conditions are mild, the post-treatment is simple, and the yield is high. The formula (I) is shown in the description.

Description

technical field [0001] The present invention relates to the technical field of chemical engineering, in particular to a phosphite-containing 1,4-pentadien-3-one derivative, and also to the phosphite-containing 1,4-pentadiene-3-one derivative. The preparation method of 3-ketone derivatives, and the application of the phosphite-containing 1,4-pentadien-3-one derivatives in inhibiting the activity of plant bacteria. 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-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-oxidati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/48C07F9/547A01N57/22A01N57/24A01P1/00
CPCA01N57/22A01N57/24C07F9/4875C07F9/5475
Inventor 薛伟陈丽娟汤旭陈英夏榕娇张橙郭涛蒋仕春王一会贺鸣
Owner GUIZHOU UNIV
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