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N-(arylaminoethyl)-3,1-benzoxazine-2-one compound, preparation method and application thereof

A technology of ketone compounds and benzoxazine, applied in the field of pesticides, can solve problems such as no reports, and achieve the effects of good bacteriostatic activity, high yield and low cost of raw materials

Active Publication Date: 2020-06-19
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, there is no document at present that has not reported N-(arylaminoethyl)-3,1-benzoxazin-2-one compounds and their use in inhibiting crops.

Method used

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  • N-(arylaminoethyl)-3,1-benzoxazine-2-one compound, preparation method and application thereof
  • N-(arylaminoethyl)-3,1-benzoxazine-2-one compound, preparation method and application thereof
  • N-(arylaminoethyl)-3,1-benzoxazine-2-one compound, preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0085] This preparation method comprises the steps:

[0086] 1) Obtain 3,1-benzoxazin-2-one by reaction of o-aminobenzyl alcohol and triphosgene:

[0087]

[0088] 2) 3,1-benzoxazin-2-one obtained in step 1) is reacted with 1,2-dichloroethane to obtain N-(2-chloroethyl)-3 with structural formula (II) , 1-Benzoxazin-2-one:

[0089]

[0090] 3) reacting the N-(2-chloroethyl)-3,1-benzoxazin-2-one obtained in step 2) with the structural formula (II) and the substituted aniline with the general structural formula (III), A reaction mixture comprising N-(arylaminoethyl)-3,1-benzoxazin-2-ones having the general structural formula (I) is obtained:

[0091]

[0092] 4) The reaction mixture containing N-(arylaminoethyl)-3,1-benzoxazin-2-one compounds obtained in step 3) with general structural formula (I) is separated and purified to obtain N-(arylaminoethyl)-3,1-benzoxazin-2-one compounds of general structural formula (I).

[0093] Preferably, said R is hydrogen or C 1 -C ...

Embodiment 1

[0118] Synthesis of N-((4-tolylamino)ethyl)-3,1-benzoxazin-2-one.

[0119] Take by weighing p-toluidine 0.35g (3.3mmol), potassium carbonate 0.83g (6mmol) and sodium iodide 0.49g (3.3mmol) join in the single-necked bottle of 100ml, add 40mL acetonitrile as solvent, carry out reflux reaction (temperature is 80 °C) for 30 minutes and then cooled to room temperature. Then 0.63 g (3 mmol) of N-(2-chloroethyl)-3,1-benzoxazin-2-one was added, stirred and refluxed at 80° C. for 26 h, and cooled to room temperature after the reaction was complete. The precipitate was filtered off and the filtrate was collected after washing 3 times with ethyl acetate. Finally, the resulting filtrate was precipitated under reduced pressure and then subjected to column chromatography to obtain a white solid with a melting point (mp): 97.1-99.0° C. and a yield of 50.7%.

[0120] 1 H NMR (500MHz, CDCl 3 )δ7.45(dd, J=7.2, 1.9Hz, 1H), 7.29-7.25(m, 2H), 7.22–7.19(m, 1H), 6.93(d, J=8.2Hz, 2H), 6.51(d , J...

Embodiment 2

[0123] Synthesis of N-((3-methylanilino)ethyl)-3,1-benzoxazin-2-one.

[0124] Take m-toluidine 0.35g (3.3mmol), potassium carbonate 0.83g (6mmol) and sodium iodide 0.49g (3.3mmol) and join in the single-necked bottle of 100ml, add 40mL acetonitrile as solvent, carry out reflux reaction (temperature is 80 °C) for 30 minutes and then cooled to room temperature. Then 0.63 g (3 mmol) of N-(2-chloroethyl)-3,1-benzoxazin-2-one was added, stirred and refluxed at 80° C. for 26 h, and cooled to room temperature after the reaction was complete. The precipitate was filtered off and the filtrate was collected after washing 3 times with ethyl acetate. Finally, the filtrate was precipitated under reduced pressure to obtain a white solid by column chromatography, melting point (mp): 122.7-123.5° C., yield: 47.6%.

[0125] 1 H NMR (500MHz, CDCl 3 )δ7.48(dd, J=7.3, 1.8Hz, 1H), 7.33-7.28(m, 2H), 7.25–7.23(m, 1H), 7.03(t, J=7.7Hz, 1H), 6.54(d , J=7.5Hz, 1H), 6.47(s, 1H), 6.42(dd, J=8.0, 2.0...

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Abstract

The invention provides an N-(arylaminoethyl)-3,1-benzoxazine-2-one compound for crop bacteriostasis, a preparation method and application thereof. The compound is prepared by reacting N-(2-chloroethyl)-3,1-benzoxazine-2-one with substituted aniline in the presence of a phase transfer catalyst and an alkali. The preparation method has the advantages of easily available raw materials, low productioncost and high yield. The compound has a good inhibition effect on the activity of crop germs and particularly has a remarkable inhibition effect on the activity of germs such as fusarium graminearum,botrytis cinerea, phytophthora capsici, sclerotinia sclerotiorum, rhizoctonia solani or magnaporthe oryzae and the like.

Description

technical field [0001] The invention relates to crop antibacterial compounds, in particular to an N-(arylaminoethyl)-3,1-benzoxazin-2-one compound, a preparation method and application thereof, and belongs to the technical field of pesticides. Background technique [0002] Among the infectious diseases of crops, there are mainly two kinds of fungal diseases and bacterial diseases, among which fungal diseases account for about 80% of the diseases. Due to the different sources of fungal diseases and bacterial diseases, their control methods and medicament usage are also quite different. [0003] The impact of fungal diseases on crops: It will cause the expansion and division of crop cells, causing clubroot or gall tumors in the affected parts, causing downy mildew, saprophytic and weak parasites, and causing the flowers, fruits, roots, tubers and other storage organs of crops to grow. Tissue necrosis, causing tissue necrosis of crops, among them, pathogenic fungi of the order...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/18A01N43/86A01P3/00
CPCA01N43/86C07D265/18
Inventor 唐子龙马彩霞焦银春彭丽芬万义超
Owner HUNAN UNIV OF SCI & TECH
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