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1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound and preparation method thereof and insecticidal activity application

A compound, pentadiene technology, applied in the field of pesticides, can solve problems such as uninvolved, and achieve the effects of good control effect and good insecticidal effect

Active Publication Date: 2011-02-16
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous studies, Li Shaobo et al [Li Shaobo, Hu Deyu, Song Baoan. Synthesis and antibacterial activity of new 1,5-diphenyl-1,4-pentadiene-3-ketoxime esters[J ]. Organic Chemistry, 2008, 28 (2): 311-316] etc. splice the two, and the obtained 1,5-diphenyl-1,4-pentadiene-3-ketoxime ester derivatives have Fungicidal properties, but not related to 1,5-diphenyl-1,4-pentadiene-3-ketoxime ether derivatives and their use in insecticidal activity

Method used

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  • 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound and preparation method thereof and insecticidal activity application
  • 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound and preparation method thereof and insecticidal activity application
  • 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound and preparation method thereof and insecticidal activity application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Example 1, 2-chloro-5-methylpyridine-1-(2-benzyloxyphenyl)-5-(4-methoxyphenyl)-1,4-pentadien-3-one oxime Ether (compound number is A):

[0101] (1) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one

[0102] Add 2-hydroxybenzaldehyde (20.0mmol), 24mL acetone, and 10mL water successively in a 100mL three-necked flask, stir at room temperature until the solids are completely dissolved, and add a solution of sodium hydroxide (24mmol)+20mL water drop by drop, and the reaction solution consists of light The yellow clear liquid turns into a wine-red clear liquid, the reaction is complete, the acetone is removed by rotary evaporation, 70mL hot water is added to the residual liquid until the red solid is completely dissolved, and carbon dioxide is introduced for about 30 minutes until the reaction liquid no longer changes color, and a light yellow solid appears , filtered, washed with water, dried, and recrystallized with acetone / water to obtain a light yellow solid with a yield o...

Embodiment 2

[0111] Example 2. Benzyl-1-[2-(4-methoxy)benzyloxyphenyl]-5-(4-methoxyphenyl)-1,4-pentadiene-3-one oxime Ether (compound number is D):

[0112] (1) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one

[0113] Synthesize as in Example 1 (1) method and conditions.

[0114] (2) Synthesis of 1-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-1,4-pentadien-3-one

[0115] Synthesize as in Example 1 (2) method and conditions.

[0116] (3) Synthesis of 1-[2-(4-methoxy)benzyloxyphenyl]-5-(4-methoxyphenyl)-1,4-pentadien-3-one

[0117] Into a 250mL three-necked flask, add 1-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-1,4-pentadien-3-one (23mmol), potassium iodide (0.23mmol) in sequence , potassium carbonate (26mmol), 100mL acetone, stirred at room temperature, then added dropwise 4-methoxybenzyl chloride (26mmol), heated to reflux, when the color of the solution changed from red to dark yellow, the reaction was complete, filtered while hot to remove excess Potassium iodide and potassium carbonate, and th...

Embodiment 3

[0123] Embodiment three, 4-methoxybenzyl-1-(4-benzyloxyphenyl)-5-(4-methoxyphenyl)-1,4-pentadiene-3-ketoxime ether ( Compound number is N):

[0124] (1) Synthesis of 4-(4-hydroxyphenyl)-3-buten-2-one

[0125] Add 4-hydroxybenzaldehyde (20.0mmol), 24mL acetone, and 10mL water successively in a 100mL three-necked flask, stir until the solids are completely dissolved, then add a solution of sodium hydroxide (24mmol)+20mL water dropwise, and the reaction solution changes from light yellow to The clear liquid turns into a wine-red clear liquid, the reaction is complete, the acetone is removed by rotary evaporation, 70mL of hot water is added to the residual liquid until the red solid is completely dissolved, and carbon dioxide is introduced for about 30 minutes until the reaction liquid no longer changes color, and a light yellow solid is produced. Filtrate, wash with water, dry, and recrystallize with acetone / water to obtain a light yellow solid with a yield of 84% and a melting ...

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Abstract

The invention discloses a 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound (I) and a preparation method thereof and insecticidal activity application. In the formula, Ar is aryl and can be substituted by one or more groups, and R1O can be in o, m and p positions. R1 and R2 are respectively C1-6 alkyl, C2-6 chain alkenyl or C2-6 chain alkynyl, benzyl, acyl and heterocyclic ring radical and can be substituted by one or more groups, wherein n is 0-3. In the invention, a series of novel curcumin derivatives 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether prepared by the oxime ether structure based on the structure of curcumin derivative 1,5-disubstituted aryl-1,4-pentadiene-3-ketone is prepared and the compounds and preparations have the function of preventing and treating crop pests, in particular a highly preventing and treating effect for plutella xylostella, nilaparvata lugens, snout moth's larva, sogatella furcifera, cnaphalocrocis medinalis, cabbage caterpillar, beet armyworm and aphid.

Description

technical field [0001] The invention belongs to the field of pesticides, and relates to a novel 1,5-disubstituted aryl-1,4-pentadiene-3-ketoxime ether compound and a preparation method thereof. Background technique [0002] Curcumin is a yellow pigment in the turmeric rhizome of Zingiberaceae Curcuma, which has a variety of biological activities, such as anti-cancer, anti-inflammatory, anti-oxidation, antibacterial, insecticidal, etc. It is also widely used in food additives, industrial dyes, cosmetics, and medicine. Curcumin derivatives have the advantages of low toxicity to the human body and wide range of biological activities, and have become a research hotspot in the field of medicine. Among them, 1,5-disubstituted aryl-1,4-pentadien-3-one derivatives It is one of the research hotspots. [0003] In terms of anticancer activity, Ligeret et al. (Ligeret H, Barthelemy S, Zini R, Tiliement J P.Effecfs of curcumin and curcumin derivatives on mitochondrial permeability tran...

Claims

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Application Information

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IPC IPC(8): C07D213/61A01N43/78C07D277/32A01N43/56C07D417/14A01P7/04C07C251/52C07C249/08C07C249/12C07C251/40C07D417/12A01N43/40C07D231/16A01N35/10C07D401/12C07C251/54
Inventor 宋宝安吴剑薛伟陈鹏丽杨松曾松胡德禹王贞超徐维明
Owner GUIZHOU UNIV
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