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Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof

A technology of aryl acryl ketone and aryl acryloyl chloride, which is applied in the field of aryl acryl ketone compounds, can solve problems such as unclear active ingredients, and achieve the effect of simple product purification method, obvious biological activity, and low cost

Inactive Publication Date: 2010-07-14
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Stellera chamaejasme (Stellera chamaejasme L.) is a plant of the genus Stellera chamaejasme. A long time ago, people discovered that the root of Stellera chamaejasme can be used to make biological pesticides—plant insecticides, which have the functions of contact killing, stomach poisoning, and fumigation. It can effectively control cabbage caterpillar, aphid, soybean borer, cotton red spider, night thief, pine moth, pine caterpillar, pine sawfly, etc., but the active ingredients are not clear, and mainly focus on the research of ethanol extract

Method used

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  • Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof
  • Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof
  • Class of aryl-acrylketone compound containing 1,3,5-dioxazine heterocycle, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1, (2E)-3-(2,4-dichlorophenyl)-1-(5-isopropyl-4-nitroimino-1,3,5-oxadiazin-3-yl )-propenone (YSX-18) preparation.

[0030] In a 50mL three-necked flask, put 0.98g of 5-isopropyl-4-nitroimino-1,3,5-oxadiazine, 1.5g of piperidine and 15mL of acetonitrile, stir, and then add 1.20g of 2, The acetonitrile solution of 4-dichlorophenylacryloyl chloride was added dropwise and reacted 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 removing the solvent is directly subjected to chromatographic separation, the eluent is a mixed solution of ethyl acetate and petroleum ether (V:V=1:1), and the solvent is precipitated under reduced pressure to obtain 0.75 g of a white solid, which is (2E)-3-(2,4-Dichlorophenyl)-1-(5-isopropyl-4-nitroimino-1,3,5-oxadiazin-3-yl)-propenone (YSX-18), yield 60.7%. That 1 H NMR spectrum data are shown in Table 3.

[0031] Ot...

Embodiment 2

[0050] Embodiment 2, the biological activity of compound of the present invention to aphid

[0051] Positive control agent (E)-1,5-diphenyl-2-ene-1-pentanone (I) and the obtained compound sample of Example 1 were weighed 12mg ( 100%) compound sample, then take 2ml of acetone / methanol (1:1) mixed solvent with a 1-5ml pipette gun and add it to the weighing bottle. After it is fully dissolved, add 18ml of an aqueous solution containing 0.1% Tween-80, fully Mix well to obtain a 600 μg / mL assay solution. Select hibiscus leaves with aphids, leave 3-day-old nymphs, immerse the leaves with aphids in the liquid medicine for 5 seconds, record the number of insects after drying, put them into a petri dish with moisturizing filter paper, cover them and put them in (25± 1) In the light incubator at ℃. Each agent treats more than 30 heads. Check the results after 24 hours. The criteria for judging the death are: touch the insect body lightly, and the individual pests that cannot crawl n...

Embodiment 3

[0054] Embodiment 3, the biological activity of compound of the present invention to Plutella xylostella

[0055] Positive control agent (E)-1,5-diphenyl-2-ene-1-pentanone (I) and the compound sample obtained in Example 1 are respectively weighed 12mg in a 20ml weighing bottle with a ten-thousandth balance (100%) compound samples, then use a 1-5mL pipette gun to take 2mL of acetone / methanol (1:1) mixed solvent into the weighing bottle, after it is fully dissolved, add 18ml of aqueous solution containing 0.1% Tween-80, Mix well to obtain a 600 μg / mL assay solution. Spinosyn 10 μg / mL was prepared in the same way. Use a hole puncher to punch clean cabbage leaves into discs with a diameter of 2 cm, soak them in the liquid medicine for 5 seconds, put the leaves back up into a petri dish with a diameter of 6 cm with moisturizing filter paper, and insert 10 instar larvae of Plutella xylostella xylostella. Heads were covered and placed in a light incubator at (27±1)°C. Check the re...

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Abstract

The invention discloses a class of aryl-acrylketone compound (formula a) containing 1,3,5-dioxazine heterocycle, a preparation method and application thereof. The structural formula of the class of compound is shown as formula a in the specification, wherein, in formula a, Y is the formula showed in the specification, wherein R is H, F, Cl, Br, CH3O, C2H5O, 2,4-Cl2, NO2, CH3. In formula a, R1 is CH3, C2H5, and CH(CH3)2. The compound in the invention has simple structure and is easy to prepare. The compound in the invention has good activity on pests such as aphid, plutella xylostella, tetranychus cinnabarinus and the like, and the activity of the majority of the compound in the invention is superior to the effective components of natural Chinese stellera root, the invention can be applied practically in agricultural production.

Description

technical field [0001] The invention relates to a class of arylpropenone compounds containing 1,3,5-oxadiazine heterocycle, a preparation method thereof and the application of the compounds in preventing and controlling agricultural pests. Background technique [0002] Stellera chamaejasme (Stellera chamaejasme L.) is a plant of the genus Stellera chamaejasme. A long time ago, people discovered that the root of Stellera chamaejasme can be used to make biological pesticides—plant insecticides, which have the functions of contact killing, stomach poisoning, and fumigation. It can effectively control cabbage caterpillar, aphid, soybean borer, cotton red spider, night thief, pine moth, pine caterpillar, pine sawfly, etc., but the active ingredients are not clear, and the research mainly focuses on ethanol extract. In 2001, people such as Liu Shigui extracted daphnetin with n-hexane for the first time, and isolated two kinds of active compounds (E)-1,5-diphenyl-2-ene-1-pentanone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/04C07D413/06A01N51/00A01P7/04A01P7/02
Inventor 凌云杨绍祥杨新玲孙玉凤孙亮芦园园
Owner CHINA AGRI UNIV
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