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Adamantyl-containing oxadiazole compound as well as preparation method and application thereof

A technology of adamantyl oxadiazoles and compounds, applied in the field of adamantyl oxadiazoles and their preparation, capable of solving problems such as leaf wilting, plant necrosis, and economic losses

Active Publication Date: 2022-02-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: rice infected by Xanthomonas oryzae will cause leaf wilting, whitening, delayed heading and reduced grain number, which will lead to reduced grain production and quality, resulting in major economic losses; citrus canker will cause Rutaceae citrus The fruit drop, rot and plant necrosis of plants belonging to the genus Hovenia, Citrus and Kumquat affect the economic value of citrus and other fruits nationwide; Pseudomonas syringae Pseudomonas syringae is susceptible to leaves, branches and fruits. Lesions appear on the leaves, pus on the branches, and fruit drop. At the same time, the disease outbreak conditions are very similar to the growth conditions of kiwifruit, which seriously restricts the development of the kiwifruit industry.
In addition, there is a serious shortage of commercial agents for the prevention and treatment of bacterial diseases, and the control effect is difficult to meet the needs of modern agriculture. Therefore, it is imminent to develop new and efficient agents against bacterial diseases

Method used

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  • Adamantyl-containing oxadiazole compound as well as preparation method and application thereof
  • Adamantyl-containing oxadiazole compound as well as preparation method and application thereof
  • Adamantyl-containing oxadiazole compound as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of intermediate 1-adamantyl methyl carboxylate

[0044] Add 1-adamantylcarboxylic acid (110.96mmol) into a 250mL round-bottomed flask containing 100mL of methanol, then add 3mL of concentrated sulfuric acid, and condense and reflux for 12h. After the temperature of the reaction system returned to room temperature, it was extracted with ethyl acetate and water, and the organic phase was collected and dried with anhydrous sodium sulfate, and after precipitation, the colorless oily intermediate 1-adamantylmethyl carboxylate was obtained with a yield of 98.0% . Its NMR data are: 1 H NMR (400MHz, CDCl 3 )δ3.51(s, 3H, O-CH 3 ), 1.87 (s, 3H, adamantaneyl-3, 5, 9), 1.77 (t, J=6.8Hz, 6H, adamantaneyl-4, 6, 8), 1.63-1.52 (m, 6H, adamantaneyl-2, 7 , 10).

Embodiment 2

[0045] Embodiment 2: the preparation of intermediate adamantane-1-carboxyhydrazine

[0046] Add 80 mL of hydrazine hydrate (content 80%) to the intermediate 1-adamantyl formate methyl ester (110.96 mmol) obtained above, and stop the reaction after reflux reaction for one week. After the reactant is cooled in an ice-water mixture, a white solid will precipitate out, and the intermediate 1-adamantylcarbohydrazide is obtained by suction filtration as a white solid with a melting point of 155-156° C. and a yield of 99.0%. Its NMR data are: 1 H NMR (400MHz, CDCl 3 )δ6.95(s, 1H, C-NH-), 2.74(s, 2H, NH- NH 2 -), 2.04 (s, 3H, adamantaneyl-3, 5, 9), 1.94-1.80 (m, 6H, adamantaneyl-4, 6, 8), 1.72 (q, J=12.3Hz, 6H, adamantaneyl-2, 7, 10); 13 C NMR (101MHz, CDCl 3 )δ178.8, 40.2, 39.2, 36.7, 28.2.

Embodiment 3

[0047] Embodiment 3: Preparation of intermediate 2-(1-adamantyl)-5-(4-piperidinyl)-1,3,4-oxadiazole

[0048] Weigh 1-adamantylcarbohydrazide (12.87mmol) and 4-piperidinecarboxylic acid (12.87mmol) into a 50mL round bottom flask, then add 20mL phosphorus oxychloride, react at 80°C for 48h, then stop the reaction. POCl was distilled off under reduced pressure 3Finally, the reactant was dissolved in 100 mL of ethyl acetate, and extracted with water; the aqueous layer collected by extraction was adjusted to pH 10-11 with sodium hydroxide solution, and then extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate, Precipitation, separation and purification by column chromatography gave the intermediate 2-(1-adamantyl)-5-(4-piperidinyl)-1,3,4-oxadiazole as a yellow oil with a yield of 75.7% . 1 H NMR (400MHz, CDCl 3 ( q, J=16.8Hz, 2H, piperidin-H), 2.07(s, 3H, admantane-H), 2.04-1.91(m, 8H, admantane-H & piperidin-H), 1.81-1.70(m, 6H, admant...

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Abstract

The invention relates to an adamantyl-containing oxadiazole compound as well as a preparation method and application thereof. The compound has a structure as shown in a general formula (I). The compound has a good inhibition effect on plant pathogenic bacteria such as Xanthomonas oryzae pv. Oryzae, Xanthomonas axonopodis pv. citri and Pseudomonas syringae pv. actinidiae. Meanwhile, the compound and adamantane-beta-cyclodextrin are utilized to perform subject-object interaction to prepare a subject-object compound, and the compound also has a good inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. Oryzae, Xanthomonas axonopodis pv. citri and Pseudomonas syringae pv. actinidiae.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an adamantyl oxadiazole compound containing an isopropanolamine substructure and a preparation method and application thereof. Background technique [0002] In recent years, with the continuous changes in agricultural farming systems and ecological conditions, plant bacterial diseases have shown a trend of rebound or aggravation, seriously endangering the yield and quality of crops. For example: rice infected by Xanthomonas oryzae will cause leaf wilting, whitening, delayed heading and reduced grain number, which will lead to reduced grain production and quality, resulting in major economic losses; citrus canker will cause Rutaceae citrus The fruit drop, rot and plant necrosis of plants belonging to the genus Hovenia, Citrus and Kumquat affect the economic value of citrus and other fruits nationwide; Pseudomonas syringae Pseudomonas syringae is susceptible to leaves, ...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D413/04A01N43/824A01P1/00
CPCC07D413/14C07D413/04A01N43/82Y02A50/30
Inventor 王培义吉庆田胡德坤母先福田小雪王小惠范丽君
Owner GUIZHOU UNIV
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