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Ultrasonic synthesis and application for oxime ester derivatives based on oxazinonepyrazole skeleton

A technology of oxazinone-based pyrazoles and oxime esters, which is applied in the application field of this type of compound

Inactive Publication Date: 2018-09-28
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the principle of structural splicing, it has not been reported to study the biological activity of oxime ester derivatives based on the oxazinone pyrazole skeleton as herbicides, antibacterials and insecticides; meanwhile, oriented insecticides are currently an emerging research hotspot, namely Pesticides that can be directional accumulated in plants to insect pests or wounds caused by insect pests. The research focus is on the directional transport of pesticides in plants. After coupling, the conjugate is loaded into the plant by means of the transfer protein of the directing group, and transported to the pest damage site through the plant phloem

Method used

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  • Ultrasonic synthesis and application for oxime ester derivatives based on oxazinonepyrazole skeleton
  • Ultrasonic synthesis and application for oxime ester derivatives based on oxazinonepyrazole skeleton
  • Ultrasonic synthesis and application for oxime ester derivatives based on oxazinonepyrazole skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1, the synthesis of 3-acetoxime ester group-5-(3-methyl-oxazinone group)-1-methyl-1H-pyrazole (compound 1)

[0056] The reaction formula to generate compound 1 is:

[0057]

[0058] Add 50mL of acetonitrile, 4.50g of 3-amidoxime-5-(3-methyl-oxazinonyl)-1-methyl-1H-pyrazole, 1gTEA into a 100mL single-necked flask, and then add 1.60g of acetyl chloride to react The temperature was 30°C, and the one-mouth bottle was put into an ultrasonic water tank (fixed power 180W) for reaction, and the reaction time was 3 hours. After the reaction was completed, it was separated by column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 5.33g of compound 1. Yield: 96.5%. IR(KBr,cm -1 ):3225(N-H),3077(CH 2 -H), 1725 (-C=O), 1605 (pyrazole ring skeleton vibration), 1533 and 1483 (benzene ring skeleton vibration), 1312 (C-F), 882 (aromatic ring C-H). 1 HNMR (CDCl 3 ,400MHz)δ:7.81(s,1H,Ar-H),5.34(s,H,N-H),5.21(s,H,N-H),2.26(q,3H,CH 2 -H).

Embodiment 2

[0059] Embodiment 2, the synthesis of 3-propioxime ester group-5-(3-ethyl-4-methyl-oxazinone group)-1-ethyl-1H-pyrazole (compound 2)

[0060] The reaction formula to generate compound 2 is:

[0061]

[0062] Add 50mL of acetonitrile, 4.50g of 3-amidoxime-5-(3-ethyl-4-methyloxazinonyl)-1-ethyl-1H-pyrazole, 1gTEA into a 100mL single-necked flask, and then add 1.80g of acetonitrile Acyl chloride, the reaction temperature is 35°C, and the single-mouth bottle is placed in an ultrasonic water tank (fixed power 200W) for reaction, and the reaction time is 4h. After the reaction was completed, it was separated by column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 4.99g of compound 2. Yield: 92.6%. IR(KBr,cm -1 ):3254 (N-H), 3080 (C-H), 1724 (-C=O), 1606 (pyrazole ring skeleton vibration), 1530 and 1399 (benzene ring skeleton vibration), 1314 (C-F), 884 (aromatic ring C-H) . 1 HNMR (CDCl 3 ,400MHz)δ:7.81(s,1H,Ar-H),5.32(s,H,N-H),5.19(s,H,N-H),2.54(s,H,C-H),1.2...

Embodiment 3

[0063] Embodiment 3, the synthesis of 3-butyroxime ester group-5-(3-ethyl-4-methyl-oxazinone group)-1-phenyl-1H-pyrazole (compound 3)

[0064] The reaction formula for generating compound 3 is:

[0065]

[0066] Add 50mL of acetonitrile, 4.50g of 3-amidoxime-5-(3-ethyl-4-methyl-oxazinonyl)-1-phenyl-1H-pyrazole, 1gTEA into a 100mL single-necked flask, and then add 2.00 g butyryl chloride, the reaction temperature is 45°C, and the single-mouth bottle is placed in an ultrasonic water tank (fixed power 250W) for reaction, and the reaction time is 3h. After the reaction was completed, it was separated by column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 5.11 g of compound 3. Yield: 93.1%. IR(KBr,cm -1 ):3231(N-H),3051(C-H),2254(-CN),1611(pyrazole ring skeleton vibration),1512 and 1367(benzene ring skeleton vibration),1314(C-F),885(aromatic ring C-H). 1 HNMR (CDCl 3 ,400MHz)δ:7.80(s,1H,Ar-H),5.33(s,H,N-H),5.29(s,H,N-H),2.47(s,H,C-H),1.72(s,H,C-H ),0.99(q,3...

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Abstract

The invention relates to the technical field of organic synthesis, in particular relates to 3-oxime ester-5-oxazinonepyrazole compounds and a method for synthesizing the compounds by utilizing an ultrasonic method, and provides an application of the compounds. The method disclosed by the invention adopts ultrasonic waves to synthesize the 3-oxime ester-5-oxazinonepyrazole compounds, the costs of synthetic raw materials are lower, the reaction conditions are mild, the operation is simple, and the yield is higher; and the prepared oxime ester derivatives (I) based on the oxazinonepyrazole skeleton have good bactericidal weeding and insecticidal biological activity, and particularly exhibit high activity in aspects of agriculture, gardening, flowers, sanitary weeding and prevention and control of pests, thereby having great development and application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 3-oxime ester-5-oxazinonylpyrazole compound and a method for synthesizing the compound by an ultrasonic method, and also provides applications of the compound. Background technique [0002] Among various heterocyclic compounds, oxazinone compounds have a wide range of biological activities and low biological toxicity, especially for weed control. Oxazinones are systemic conductive herbicides, which inhibit the growth of sensitive plant meristematic cells in a way different from other herbicides. Small side effects, small drug resistance and high selectivity. Pyrazole compounds have a wide range of biological activities and are one of the main structures of new pesticide research in recent years. Due to the high efficiency, low toxicity and structural diversity shown by pyrazole compounds, they have very broad research and development prospects. In the past ten year...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D413/14A01N43/86A01P3/00A01P7/02A01P7/04A01P13/00
CPCA01N43/86C07D413/04C07D413/14
Inventor 陈连清黄裕峰
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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