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Heterocycle substituted 1,3,4-oxadiazole compound and preparation method and application thereof

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

Active Publication Date: 2019-04-19
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Heterocycle substituted 1,3,4-oxadiazole compound and preparation method and application thereof
  • Heterocycle substituted 1,3,4-oxadiazole compound and preparation method and application thereof
  • Heterocycle substituted 1,3,4-oxadiazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
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. Bioorg Med Chem Lett, 2016, 26, 1214-1217]. It (0.5g, 2.44mmol) was added to 8mL POCl containing 6-bromohexanoic acid (0.48g, 2.44mmol) 3 In the solution, react at 75°C for 10h. Remove POCl under reduced pressure 3 , and then add 70mL of ethyl acetate to the residue for extraction, the organic layer was washed with water, potassium carbonate aqueous solution, brine, dried with anhydrous sodium sulfate, filtered, and then precipitated. Using PE:EA=8:1 as the eluent, the intermediate was obtained as a white solid with a yield of 73.2% and a melting point of 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 oxadiazole

[0068] 2-(5-bromopentyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 4 (0.2g, 0.55mmol), 2-methyl-5-nitro -1H-imidazole (0.14g, 1.10mmol) 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 stripped. Use CH 2 Cl 2 :CH 3OH=40:1 was used as the eluent to obtain the desired product as a brown solid, yield: 99.9%, melting point: 49.8-50.1°C.

[0069] The other compounds were prepared in analogy to the synthetic method steps of Examples 1 and 2 using the corresponding starting materials.

[0070] The structure, H-NMR and C-NMR data of the synthesized 1,3,4-oxadiazolylimidazole (partial heterocycle) compounds are shown in Table 1, and their physical and chemica...

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Abstract

The invention relates to a heterocycle substituted 1,3,4-oxadiazole compound and a preparation method and application thereof. The compound includes the following steps shown in the general formula (I) in the description. The compound has a good inhibitory effect on pathogenic bacteria and fungi, such as rice white leaf diseases, citrus canker diseases, pepper wilt pathogenic bacteria, blueberry phytophthora lateralis, wheat gibberella saubinetii, potato phytophthora infestans, oilseed rape sclerotinia sclerotiorum, dragon-fruit colletotrichum orbiculare and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a heterocyclic-substituted 1,3,4-oxa(thia)diazole compound, a preparation method and application thereof. Background technique [0002] In recent years, the emergence and development of plant bacterial and fungal diseases have caused global production constraints and are a major challenge to 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 the development of drug-resistant varieties, the development of synthetic fungicides, and the utilization of biocontrol agents. However, the long-term abuse of fungicides and the emergence of new pathogenic bacteria have caused certain resistance of pathogenic bacteria. ...

Claims

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Application Information

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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
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