1,4-pentadiene-3-ketone derivative containing benzotriazinone as well as preparation method and application of 1,4-pentadiene-3-ketone derivative

A technology of benzotriazinone and pentadiene, which is applied in the fields of botanical equipment and methods, chemicals for biological control, biocides, etc., can solve the problems of human harm, long residual time and high residual amount, achieve good inhibitory effect

Active Publication Date: 2018-01-19
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high acute toxicity of most organophosphorus pesticides and the high residues in plant foods, especially fruits and vegetables, the residue time is long, which has great harm to the human body

Method used

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  • 1,4-pentadiene-3-ketone derivative containing benzotriazinone as well as preparation method and application of 1,4-pentadiene-3-ketone derivative
  • 1,4-pentadiene-3-ketone derivative containing benzotriazinone as well as preparation method and application of 1,4-pentadiene-3-ketone derivative
  • 1,4-pentadiene-3-ketone derivative containing benzotriazinone as well as preparation method and application of 1,4-pentadiene-3-ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]Synthesis of 1-(4-(3-chloromethylbenzotriazin-4-one)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one (Compound No. for II-1), including the following steps:

[0040] (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 65%.

[0041] (2) Synthesis of 1-(2-thienyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: 4-(hyd...

Embodiment 2

[0047] Synthesis of 1-(4-(3-chloromethylbenzotriazin-4-one)phenyl)-5-(4-methylphenyl)-1,4-pentadien-3-one( Compound number is II-2), comprises the following steps:

[0048] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0049] (2) Synthesis of 1-(4-methylphenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is With 4-methylbenzaldehyde as raw material.

[0050] (3) Synthesis of 3-chloromethylbenzotriazin-4-one: as in step (5) of Example 1.

[0051] (4) Synthesis of 1-(4-(3-methylbenzotriazin-4-one)phenyl)-5-(4-methylphenyl)-1,4-pentadien-3-one : As in Example 1 (6) step, the difference is that 1-(4-methylphenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one is used as raw material.

Embodiment 3

[0053] Synthesis of 1-(4-(3-methylbenzotriazin-4-one)phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one (compound number is II -3), including the following steps:

[0054] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0055] (2) Synthesis of 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is that pyridine -3-formaldehyde as raw material.

[0056] (3) Synthesis of 3-chloromethylbenzotriazin-4-one: as in step (5) of Example 1.

[0057] (4) Synthesis of 1-(4-(3-methylbenzotriazin-4-one) phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one: as Step (6) of Example 1, the difference is that 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one is used as raw material.

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Abstract

The invention discloses a 1,4-pentadiene-3-ketone derivative containing benzotriazinone. The 1,4-pentadiene-3-ketone derivative containing benzotriazinone is characterized by having the general formula as shown in the specification, wherein R1 is phenyl, substituted phenyl (p-fluorophenyl, p-chlorophenyl, o-chlorophenyl, 2-methyoxyphenyl, 4-methyoxyphenyl, 4-methylphenyl, 2,4-dimethyoxyphenyl, 3,4-dimethyoxyphenyl, cinnamaldehyde group, 3-nitrophenyl, 2-chloro-5-nitrophenyl and the like), heterocyclic group (furyl, thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrryl and the like) or substituted aromatic heterocyclic group (5-methyl thiazole, 5-methyl-2-thienyl, 4-bromo-2-thienyl and the like), and R2 is a hydrogen atom, methyl (ethyl), methoxyl (ethyoxyl) and the like. The compound disclosedby the invention has relatively high inhibiting activity for citrus canker bacteria, ralstonia solanacearum and tobacco mosaic viruses so as to be used for preparing an agricultural bactericide and anantiviral agent.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a preparation method of a benzotriazinone-containing 1,4-pentadien-3-one derivative and its application in antibacterial and antiviral activities. Background technique [0002] Curcumin is a pigment extracted from turmeric, a plant of the ginger family, and is also present in other plants of the ginger family. Modern studies have found that curcumin has various biological activities such as insecticidal, antibacterial, antiviral, anti-inflammatory, anti-oxidant, anti-cancer, anti-rheumatoid, etc. However, the presence of β-diketone structure and active methylene in its molecule makes it It is unstable under neutral or basic conditions (pH>6.5). The curcumin analog 1,5-disubstituted-1,4-pentadien-3-one compound has better stability, and like curcumin, has various biological activities and has less toxic and side effects. Using curcumin as the lead compound to mod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/08C07D409/12C07D401/12C07D405/12A01N43/707A01P1/00A01P3/00
Inventor 薛伟张菊平张橙陈丽娟王一会李普李琴阮祥辉王晓斌吴小琼王俊
Owner GUIZHOU UNIV
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