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Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof

A technology of stilbene and its derivatives, which is applied in the field of pesticide chemistry and fine chemicals, can solve the problems of narrow application range, harsh synthesis conditions, and inconspicuous effects of a single active structural unit, and achieve significant insect growth and development inhibitory activity, synthetic Easy operation and environment-friendly effect

Inactive Publication Date: 2011-08-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although 1,3,4-oxadiazole derivatives have a variety of biological activities, their synthesis conditions are generally harsh, requiring higher temperatures, and corrosive dehydrating agents, etc., and post-treatment is more difficult. In addition, 1, The single active structural units of 3,4-oxadiazole and stilbene have a narrow application range and the effect is not obvious

Method used

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  • Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof
  • Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof
  • Stilbene derivative with 1,3,4-oxadiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of 2-phenyl-5-(4-(3,4-dichlorostyryl)phenyl)-1,3,4-oxadiazole (Ⅰ)

[0035]

[0036] (I)

[0037] (1) Dissolve 30.0g (0.20mol) of p-toluylhydrazide in 700ml of absolute ethanol, add 21.2g (0.20mol) of benzaldehyde, heat and stir under reflux for 0.5h to obtain a reaction solution, cool and filter the reaction solution, and dry the filter cake to obtain 42.0g white solid; weigh 23.8g (0.10mol) of the white solid and dissolve it in 500ml absolute ethanol, then add 85g (0.30mol) chloramine T, heat and reflux and stir for 3h to obtain the intermediate reaction solution , the remaining solid after ethanol was evaporated was washed with distilled water and filtered 4 times, and the filter cake was dried, and the resulting dry filter cake was recrystallized with a mixed solution of distilled water and acetone with a volume ratio of 1:1 to obtain 15.75g 2-phenyl-5- (4-Benzyl)-1,3,4-oxadiazole, its yield: 66.7%. Melting point: 129°C. Proton NMR structu...

Embodiment 2

[0041] Example 2 Synthesis of 2-phenyl-5-(4-(2,4-dichlorostyryl)phenyl)-1,3,4-oxadiazole (Ⅱ)

[0042]

[0043] (II)

[0044] Reaction steps (1), (2), (3) are the same as in Example 1, and the recrystallization product of step (3) gained is the same as that of Example 1;

[0045] (4) 1.0 g (2.69 mmol) of 4-(5-phenyl-1,3,4-oxadiazol-2-yl) benzyl phosphonate prepared in step (3) and 0.47 g ( 2.69mmol) 2,4-dichlorobenzaldehyde was dissolved in 10ml N,N-dimethylformamide to obtain a solution, then in the solution, dropwise added anhydrous potassium tert-butoxide with a mass percentage of 20%. 6ml of ethanol solution, stirred and reacted at 60°C for 5 h to obtain a reaction solution, cooled and filtered the reaction solution, and the resulting filter cake was recrystallized with a mixture of dimethyl sulfoxide and ethanol at a volume ratio of 7:1 to obtain the final product. Yield: 91.2%. Melting point: 213.8°C. Proton NMR structural characterization data: 1H NMR (400 MHz, ...

Embodiment 3

[0047] Example 3 Synthesis of 2-(2,4-dichlorophenyl)-5-(4-styrylphenyl)-1,3,4-oxadiazole (Ⅲ)

[0048]

[0049] (Ⅲ)

[0050] (1) Dissolve 15.0g (0.10mol) of p-toluylhydrazide in 300ml of absolute ethanol, add 17.5g (0.10mol) of 2,4-dichlorobenzaldehyde, heat and stir under reflux for 1 hour to obtain a reaction solution, and cool And filter the reaction solution, dry the filter cake to obtain 29.5g white solid; weigh 29.0g (0.095mol) white solid and dissolve it in 500ml absolute ethanol, then add 136g (0.48mol) chloramine T, heat, stir and reflux for 5h The intermediate reaction solution was obtained, and the remaining solid was washed with distilled water and filtered 5 times after the ethanol was evaporated, and the obtained filter cake was dried, and the dried product was recrystallized with a mixed solution of distilled water and acetone with a volume ratio of 1:2 to obtain 15.59 g of 2- (2,4-Dichlorophenyl)-5-(4-benzyl)-1,3,4-oxadiazole. Yield: 53.9%. Melting poi...

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Abstract

The invention provides a stilbene derivative with 1,3,4-oxadiazole and a preparation method and application thereof. The preparation method of the stilbene derivative with 1,3,4-oxadiazole comprises four specific reaction steps, namely oxidation cyclization reaction, NBS (N-bromosuccinimide) bromination reaction, triethyl phosphite esterification reaction and Wittig-Honner reaction. The stilbene derivative with 1,3,4-oxadiazole disclosed by the invention can be used to obviously inhibit the growing activities of Lepidopteron such as beet armyworm and cabbage looper and have important application value in the developments of environmentally friendly, efficient and new pesticides.

Description

technical field [0001] The invention relates to the field of pesticide chemistry and fine chemicals, in particular to a stilbene derivative containing 1,3,4-oxadiazole, a preparation method and application thereof. Background technique [0002] 1,3,4-Oxadiazole derivatives have a variety of biological activities: such as insecticidal, bactericidal, anticancer, anti-inflammatory and so on. The reason why such derivatives have so many biological activities mainly depends on the basic skeleton with oxadiazole ring in the molecule. 2,5-disubstituted 1,3,4-oxadiazoles exhibit a wide range of biological activities such as insecticidal, herbicidal, and bactericidal depending on the 2,5-position substituents. A large number of research results show that a certain Some 2,5-disubstituted 1,3,4-oxadiazole derivatives have good insect growth inhibitory activity. Foreign companies have successively developed pesticides containing 1,3,4-oxadiazole structure such as the herbicide oxadiaz...

Claims

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Application Information

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IPC IPC(8): C07D271/107A01N43/824A01P7/04
Inventor 何道航李新伟
Owner SOUTH CHINA UNIV OF TECH
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