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Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof

A technology of aryl acryl ketone and aryl acryloyl chloride, which is applied in the application field of pest control, can solve the problems of limited sources, limited practical application, and difficult synthesis, and achieves good activity, good chemical killing activity, and simple operation Effect

Inactive Publication Date: 2009-04-08
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limited sources of these two compounds and the difficulty of synthesis, their practical application in the control of aphids is limited. Therefore, the structural modification and modification of the active components in Daphne chamaejasma is expected to find compounds with practical value
[0004] Regarding the structural transformation of active ingredients (1) and (2) of Daphne chamaejasma, so far there is only one document publicly reported, that is, Hou taiping et al. (Synthesis and structure-activity study of botanical aphicides 1,5-diphenyl-1-pentanone analogues.Pesticide Biochemistryand Physiology, 2007,89:60~64), although this document involves the preparation of 1,5-diphenyl-1-pentanone (1) analogues, it is mainly limited to the carbon chain length The modification did not introduce heterocycles, and only tested the biological activity against aphids; in order to meet the requirements of pest control in the new situation, it is necessary to develop more analogs with simple structures and easy synthesis with obvious biological activities to reduce Drug synthesis difficulty and environmental pollution

Method used

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  • Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof
  • Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof
  • Nitrogen heterocyclic ring substituted arylpropenone compounds, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1. Preparation of (2E)-3-(4-fluorophenyl)-1-(2-cyanoimino-thiazolidin-3-yl)-propenone (A12)

[0031] In a 100 mL three-necked flask, put 1.27 g of 2-cyanoimino-thiazolidine, 1.5 g of piperidine and 30 mL of acetonitrile, stir, add 2.0 g of acetonitrile solution of 4-fluoro-phenylacryloyl chloride, dropwise After completion, the reaction was carried out at 40°C for 5h. The reaction solution was cooled to room temperature, and the solvent was removed under reduced pressure to obtain a red liquid. Then, the product after desolventizing was directly passed through a silica gel column for chromatographic separation, and the eluent was a mixture of ethyl acetate and petroleum ether (V:V=1:10), which was desolvated under reduced pressure to obtain 2.3 g of a white solid. , namely (2E)-3-(4-fluorophenyl)-1-(2-cyanoimino-thiazolidin-3-yl)-propenone (A12), with a yield of 85.0%. That 1 The H NMR spectral data are shown in Table 1.

[0032] Other thiazolidine-containin...

Embodiment 2

[0033] Example 2. Preparation of (2E)-3-(4-fluorophenyl)-1-(2-nitroimino-imidazolidine-1-yl)-propenone (A1)

[0034] Prepared according to the preparation method of Example 1, wherein, 2-nitroiminoimidazolidine is used as the reaction raw material to replace 2-cyanoimino-1,3-thiazolidine, the solvent used is DMF, and pyridine is used to replace piperidine, and the reaction temperature is 80°C, and the reaction time is 8h. The rest of the reaction operation steps are the same as in Example 1.

[0035] Purify the reacted product according to the purification method described in Example 1 to obtain 1.9 g of a white solid product, which is (2E)-3-(4-fluorophenyl)-1-(2-nitroimino-imidazole) Alk-1-yl)-propenone (A1) in 75% weight yield. That 1 See Table 1 for the H NMR spectrum.

[0036] Other substituted aryl acryl ketones containing imidazolidine were prepared in the same way.

Embodiment 3

[0037] Example 3. Preparation of (2E)-3-(4-fluorophenyl)-1-piperidinylpropenone (A23)

[0038] Prepared according to the preparation method of Example 1, wherein, piperidine is used as the reaction raw material to replace 2-cyanoimino-1,3-thiazolidine, the solvent used is toluene, the basic substance used is sodium hydroxide, and the reaction temperature is 100 ° C , the reaction time is 6h.

[0039] Purify the reacted product according to the purification method described in Example 1 to obtain 2.3 g of needle-like solid product, which is (2E)-3-(4-fluorophenyl)-1-piperidinylpropenone (A23) , the yield was 92.0%. That 1 The H NMR spectrum results are shown in Table 1.

[0040] Other piperidine-containing substituted aryl acryl ketones were prepared in the same way.

[0041]The structures, melting points, and hydrogen spectrum data of compounds of formula I are listed in Table-1 below, which were prepared according to various methods similar to those shown in the preceding...

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Abstract

The invention provides a nitrogen heterocyclic ring substituted aryl propenone compound (formula I), a preparation method and application thereof. The structural formula of the compound is shown in the formula I, wherein in the formula I, R in X (shown as formula on the right) is H, F, Cl, Br, CH3O, C2H5O, 2, 4-dichloro, NO2 and CH3; and in the formula I, Y is 2-nitroiminoimidazolidine, 2-cyanoimino-1, 3-thiazolidine, thiazolidine and other nitrogen heterocyclic rings. The compound has excellent chemical killing activity to aphid, tetranychus cinnabarinus, diamondback moth and other harmful pests, and biological activity of partial compound is equivalent to that of control insecticides. Furthermore, compared with effective constituents of natural Stellera chamaejasma L, the compound has the advantages that the compound has simple structure and easy acquisition, and can be actually applied to agricultural production.

Description

technical field [0001] The invention relates to a nitrogen-containing heterocyclic substituted aryl acryl ketone compound and a preparation method thereof, as well as the application of the compound in the prevention and control of harmful organisms. Background technique [0002] With the continuous emergence of new heterocyclic pesticides in recent years and the research progress in the fields of botanical pesticides, new ideas have been provided for the research and development of new pesticides; due to the extremely diverse chemical structures of botanical active substances, with the modernization of With the development of separation technology and spectral structure identification technology, it has become an effective way to find novel chemical structures from natural active substances and take this as a guide to design and develop new pesticides with unique modes of action and good environmental compatibility. [0003] Stellera chamaejasme L. is a genus of Stellera ch...

Claims

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Application Information

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IPC IPC(8): C07D233/52C07D277/18C07D295/182C07D307/54C07D333/24A01N51/00A01N47/40A01N43/40A01P7/00
Inventor 凌云康铁牛杨新玲李继德佘永红杨绍祥孙亮孙玉凤
Owner CHINA AGRI UNIV
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