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A class of heterocyclic substituted 1,3,4-oxa(thia)diazole compounds and its preparation method and use

A kind of azole compound and compound technology, applied in the field of medicinal chemistry

Active Publication Date: 2022-05-24
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the long-term abuse of fungicides and the emergence of new pathogenic bacteria have caused the pathogenic bacteria to develop certain resistance

Method used

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  • A class of heterocyclic substituted 1,3,4-oxa(thia)diazole compounds and its preparation method and use
  • A class of heterocyclic substituted 1,3,4-oxa(thia)diazole compounds and its preparation method and use
  • A class of heterocyclic substituted 1,3,4-oxa(thia)diazole compounds and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0066] Example 1: Preparation of intermediate 2-(5-bromopentyl)5-(2,4-dichlorophenyl)-1,3,4-oxadiazole to synthesize 2,4-dichlorobenzohydrazide, Reference [Wang, P.Y; Zhou, L; Zhou, J; Wu, Z.B; Xue, W; Song, B.A; Yang, S. Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4 -oxadiazole thioether / sulfoxide / sulfone derivatives. BioorgMed Chem Lett, 2016, 26, 1214-1217]. This (0.5 g, 2.44 mmol) was added to 8 mL POCl containing 6-bromohexanoic acid (0.48 g, 2.44 mmol) 3 In the solution, the reaction was carried out at 75°C for 10h. Removal of POCl under reduced pressure 3 , and then 70 mL of ethyl acetate was added to the residue for extraction. The organic layer was washed with water, aqueous potassium carbonate and brine, dried over anhydrous sodium sulfate, filtered, and then desolubilized. Using PE:EA=8:1 as eluent, the intermediate was obtained as a white solid in 73.2% yield, mp: 164.3-165.6°C.

Embodiment 2

[0067] Example 2: 2-(2,4-Dichlorophenyl)-5-(5-(2-methyl-5-nitro-1H-imidazol-1-yl)pentyl)-1,3,4 - Preparation of oxadiazoles

[0068] 2-(5-Bromopentyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 4 (0.2 g, 0.55 mmol), 2-methyl-5-nitro -1H-imidazole (0.14 g, 1.10 mmol) and K 2 CO 3 Dissolve in DMF (7 mL) and stir at 60°C for 12 hours. The solvent was removed under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered, and then desolvated. use CH 2 Cl 2 : CH 3OH=40:1 as eluent gave the desired product as a brown solid, yield: 99.9%, mp: 49.8-50.1°C.

[0069] In analogy to the synthetic procedure steps of Examples 1 and 2, other compounds were prepared using the corresponding starting materials.

[0070] The structures of the synthesized 1,3,4-oxadiazolylimidazole (partial heterocycle) compounds are shown in Table 1, and the 1,3,4-oxadiazolyl imidazole (partial heterocycle) compounds ar...

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Abstract

The invention relates to a class of heterocyclic substituted 1,3,4-oxa(thia)diazole compounds, a preparation method and application thereof. The compound has a structure shown in general formula (I): the compound has a good inhibitory effect on pathogenic bacteria and fungi, such as rice white leaf disease, citrus canker bacterium, pepper fusarium wilt, blueberry root rot, wheat Fusarium head blight, potato infestation, rapeseed sclerotinia, dragon fruit anthracnose, etc. all have good inhibitory effects.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a heterocyclic substituted 1,3,4-oxa(thi)adiazole compound and a preparation method and application thereof. Background technique [0002] In recent years, the emergence and development of bacterial and fungal diseases of plants has restricted global production and is a major challenge for agriculture worldwide. These diseases are mainly formed and spread by invasive phytopathogenic bacteria and fungi, causing significant damage to a variety of economically important crops such as rice, citrus, and tobacco. To address this issue, many strategies to combat these diseases have been explored, such as developing resistant varieties, developing synthetic fungicides, and utilizing biological control agents. However, the long-term abuse of fungicides and the emergence of new pathogenic bacteria have made pathogenic bacteria have a certain resistance. Therefore, there is an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/06C07D413/14A01N43/824A01P1/00A01P3/00
CPCA01N43/82C07D413/06C07D413/14
Inventor 杨松曾丹叶豪杰方子冕黄浩杰刘帅帅杨彬鑫王培义
Owner GUIZHOU UNIV