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Chalcone derivatives containing 1,2,4-triazine and production method and application thereof

A derivative, the technology of chalcone, which is applied in the application field of inhibiting the activity of plant bacteria, can solve the problem that there is no relevant report on the activity of inhibiting plant bacteria, and achieve a good effect of inhibiting activity

Active Publication Date: 2019-06-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, chalcones have certain inhibitory activity on plant bacteria, and 1,2,4-triazine has various biological activities such as anti-cancer, anti-α-glucosidase and anti-platelet body, etc. Bacterial activity has not been reported

Method used

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  • Chalcone derivatives containing 1,2,4-triazine and production method and application thereof
  • Chalcone derivatives containing 1,2,4-triazine and production method and application thereof
  • Chalcone derivatives containing 1,2,4-triazine and production method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-3-(2-methoxy Phenyl)-2-propylene-1-one (compound number is X1) comprises the following steps:

[0033](1) Synthesis of 4-(hydroxyphenyl)-3-(2-methoxyphenyl)-2-propen-1-one: 4-hydroxyacetophenone (2.5g) and 2-methoxy Benzaldehyde (3.0g) was added to absolute ethanol, after stirring for about 15 minutes, after the reaction system was ice-bathed for about 30 minutes, 15 mL of 4mol / L NaOH solution was slowly added to the system, and after the NaOH solution was added dropwise, remove In an ice bath, stir at room temperature for about 24 hours. 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 (1:3) was recrystallized to obtain a yellow solid wit...

Embodiment 2

[0038] (E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-3-(2,4-di Methoxyphenyl)-2-propene-1-one (compound number is X2) comprises the following steps:

[0039] (1) Synthesis of 4-(hydroxyphenyl)-3-(2,4-dimethoxyphenyl)-2-propene-1-one: as in the first (1) step of Example 1, the difference is that 2 , 4-dimethoxybenzaldehyde as raw material.

[0040] (2) Synthesis of 1-(4-(2-bromoethoxy)phenyl-3-(2,4-dimethoxyphenyl)-2-propene-1-one: as in Example 1 ( 2) step.

[0041] (3) Synthesis of 5,6-diphenyl-1,2,4-triazine-3-mercaptool: as in step (3) of Example 1.

[0042] (4)(E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-3-(2, The synthesis of 4-dimethoxyphenyl)-2-propene-1-ketone, as the first (4) step of embodiment 1, difference is to use 1-(4-(2-bromoethoxy) phenyl-3 -(2,4-dimethoxyphenyl)-2-propen-1-one as starting material.

Embodiment 3

[0044] (E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-3-phenyl-2-propene -1-keto (compound number is X3) comprises the following steps:

[0045] (1) Synthesis of 4-(hydroxyphenyl)-3-phenyl-2-propen-1-one: as in step (1) of Example 1, the difference is that benzaldehyde is used as a raw material.

[0046] (2) Synthesis of 1-(4-(2-bromoethoxy)phenyl-3-phenyl-2-propen-1-one: as in step (2) of Example 1.

[0047] (3) Synthesis of 5,6-diphenyl-1,2,4-triazine-3-mercaptool: as in step (3) of Example 1.

[0048] (4)(E)-1-(4-(2-((5,6-diphenyl-1,2,4-triazine-3-mercaptoethoxy)phenyl)-3-phenyl- The synthesis of 2-propen-1-one is as in the step (4) of embodiment 1, the difference is that 1-(4-(2-bromoethoxy) phenyl-3-phenyl-2-propene-1- Ketones as raw materials.

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Abstract

The invention discloses chalcone derivatives containing 1,2,4-triazine and a production method and application thereof. A general formula of the chalcone derivatives containing the 1,2,4-triazine is as shown in the description, wherein n=2,3,4, R is phenyl or substituted phenyl or substituted aromatic heterocycte, and R1 is phenyl or substituted phenyl or alkyl of C1-C6. The chalcone derivatives containing the 1,2,4-triazine have good activity of inhibiting xanthomonas oryzae, xanthomonas citri and tobacco ralstonia solanacearum, raw materials are easy to obtain, reaction conditions are mild,post-treatment is simple, and the yield is high.

Description

technical field [0001] The present invention relates to the field of chemical engineering, in particular to a chalcone derivative containing 1,2,4-triazine, and also to the chalcone derivative containing 1,2,4-triazine The preparation method of the chalcone derivatives, and the application of the chalcone derivatives containing 1,2,4-triazine in inhibiting the activity of plant bacteria. Background technique [0002] Xanthomonas oryzae, X. citrus and R. solanacearum are three of the most difficult plant pathogens to control, causing billions of dollars in economic losses worldwide each year. At present, Thiodiazole-copper and Bismerthiazol are mainly used as commercial agents for control, but the effect is not obvious. [0003] Chalcone is a natural organic compound. Chalcone and its derivatives are widely used in agriculture because of their good bactericidal, antiviral, insecticidal and other biological activities. [0004] In 2011, Liu Xiaofang et al. (Eur.J.Med.Chem, 2...

Claims

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Application Information

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IPC IPC(8): C07D253/07C07D405/12C07D409/12A01P1/00
Inventor 薛伟汤旭苏时军贺军陈梅夏榕娇郭涛陈英吴佳祥王俊
Owner GUIZHOU UNIV
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