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1,3,4-oxadiazole thioether compound as well as preparation method and application thereof

A technology for oxadiazole sulfide and compound, which is applied in the field of 1,3,4-oxadiazole sulfide compound and its preparation, can solve the problems of citrus rot and influence on citrus yield and the like

Inactive Publication Date: 2019-03-29
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, Xanthomonas axonopodis pv. Citri causes citrus rot and affects citrus production globally

Method used

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  • 1,3,4-oxadiazole thioether compound as well as preparation method and application thereof
  • 1,3,4-oxadiazole thioether compound as well as preparation method and application thereof
  • 1,3,4-oxadiazole thioether compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: the preparation of 2-(pyridine-2-hydroxyl) ethyl acetate

[0057] Dissolve 8.0g (84.1mmol) of 2-hydroxypyridine in 100mL of acetone, then add potassium carbonate (14.0g, 100.9mmol) and ethyl bromoacetate (9.4mL, 84.2mmol), react at 56°C for 12h to stop the reaction, add 100mL Ethyl acetate, washed with water 30 mL x 3 times, dried over anhydrous sodium sulfate, and precipitated to obtain 11.7 g of a colorless oil with a yield of 76.7%.

[0058] For other ester intermediate compounds, corresponding raw materials or substituents are used, and are synthesized with reference to the steps of Example 1.

Embodiment 2

[0059] Embodiment 2: the preparation of 2-(2-pyridyl-oxygen) acetylhydrazide

[0060] Dissolve 11.5g (106.7mmol) of ethyl 2-(pyridine-2-hydroxy)acetate in 100mL of absolute ethanol, then add hydrazine hydrate (8.5mL, 138.6mmol), react at 85°C for 6h to stop the reaction, and desolvate column chromatography (Eluant dichloromethane:methanol=5:1) 10.2 g of yellow oil, yield 57.2%.

[0061] Other hydrazide intermediate compounds are synthesized by referring to the steps of Example 2 using corresponding raw materials or substituents.

Embodiment 3

[0062] Example 3: Preparation of 2-thiol-(5-(2-pyridyl-oxygen)-methyl)-1,3,4-oxadiazole

[0063] Dissolve 9.9g (59.4mmol) of 2-(2-pyridyl-oxy)acetylhydrazide in 100mL of absolute ethanol, then add potassium hydroxide (7.8g, 118.9mmol) and carbon disulfide (5.4mL, 89.2mmol), and react at room temperature 12h, react at 85°C for 12h to stop the reaction, add 100mL of water after precipitation, adjust Ph=3-4 with 5% hydrochloric acid aqueous solution, filter with suction to obtain 4.1g of light yellow solid, yield 33.3%, melting point: 184-185°C.

[0064] Other thiol intermediate compounds are synthesized with reference to the steps of Example 3 using corresponding raw materials or substituents.

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Abstract

The invention relates to a 1,3,4-oxadiazole thioether compound as well as a preparation method and application thereof. The compound has a structure shown as a general formula (I) in the description.The compound has a good inhibition effect on pathogenic bacteria and fungi. By aiming at xanthomonas oryzae pv.oryzae, ralstonia solanacearum, cucumber xanthomonas oryzae, konjac xanthomonas oryzae, xanthomonas axonopodis pv.citri, botryosphaeria dothidea, bacterial canker and wilt of tomato, pseudomonas syringae pv.actinidae, Leucostoma cincta(Fr.:Fr.)Hohn, B.cinerea, F.oxysporum, S.sclerotiorum,G.zeae, P.infestans, P.cinnamomi and the like, good inhibition effects are achieved.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,3,4-oxadiazole sulfide compound substituted with an aromatic ether group or an alkyl ether group, a preparation method and application thereof. Background technique [0002] In recent years, plant bacteria and fungi have seriously affected the yield and quality of crops worldwide, causing huge economic losses to farmers. For example, rice bacterial blight (Xanthomonas oryzaepv.Oryzae) is a rod-shaped Gram-negative bacterium that can cause the leaves of rice to wither and turn white, and it brings at least 10-50% of rice-growing countries every year. production cuts. Additionally, Xanthomonas axonopodis pv. Citri causes citrus rot, affecting citrus yields globally. In the process of agricultural production, due to the long-term use of traditional medicaments, plant pathogenic bacteria have developed certain resistance to them. Therefore, it is of great significa...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D413/14C07D271/113A01N43/824A01P1/00A01P3/00
CPCA01N43/82C07D271/113C07D413/12C07D413/14
Inventor 杨松陶青青王培义吴元元龙青素薛伟
Owner GUIZHOU UNIV
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