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Pyrazolyl-oxa(thia)diazole compound containing pyridinium salt, and preparation method and application thereof

A technology of azole compounds and pyrazole oxadiazoles, which is applied in the field of pyrazole oxadiazole compounds and their preparation, and can solve problems such as inactivity

Active Publication Date: 2017-08-18
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, C14 and C16 were found to have good inhibitory activity against yeast-type fungi, while C16 was completely inactive against filamentous fungi

Method used

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  • Pyrazolyl-oxa(thia)diazole compound containing pyridinium salt, and preparation method and application thereof
  • Pyrazolyl-oxa(thia)diazole compound containing pyridinium salt, and preparation method and application thereof
  • Pyrazolyl-oxa(thia)diazole compound containing pyridinium salt, and preparation method and application thereof

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Embodiment 1

[0023] Example 1 of the present invention: target compound 10-(2-thioether-5-(1phenyl-2-trifluoromethyl)pyrazolyl)-1,3,4-oxadiazole-decyl-1 - Preparation of pyridinium bromide salt

[0024] Dissolve 0.5g 2-(10-bromodecyl)thioether-5-(1phenyl-2-trifluoromethyl)pyrazolyl-1,3,4-oxadiazole in 5mL pyridine, 50℃ The reaction was carried out for 6h, desolventized, and purified by column chromatography to obtain 0.53g of yellow liquid with a yield of 92.0%.

[0025] Refer to Example 1 for the synthesis of thioether and oxyether target compounds.

[0026] The structures, hydrogen NMR, carbon and fluorine spectra and mass spectrometry data of some of the synthesized pyrazole dioxa (thi) diazole compounds containing pyridine salts are shown in Table 1, and the physicochemical properties are shown in Table 2.

[0027] H NMR and C NMR data of some compounds in Table 1

[0028]

[0029]

[0030]

[0031]

[0032]

[0033] Table 2 Physicochemical properties of some target c...

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Abstract

The invention discloses a pyrazolyl-oxa(thia)diazole compound containing pyridinium salt, and a preparation method and application thereof. The compound has the structure as shown in the following general formula (I). On the basis of a pyrazolyl-oxa(thia)diazole thioether(oxoether) compound, a pyridinium group capable of improving the biological activity of a target compound is introduced into the system to synthesize a series of pyrazolyl-oxa(thia)diazole oxoether or thioether amphipathic molecules containing the pyridinium salt; moreover, the compound has a good inhibition effect on pathogenic bacteria and fungi, has good inhibition effects on bacteria (bacterial leaf blight of rice, ralstonia solanacearum, xanthomonas citri and the like) and fungi (gibberella zeae, phytophthora infestans, rhizoctonia solani, botrytis cinerea pers, fusarium oxysporum, apple rot pathogenic bacteria and the like), and provides an important scientific base for research, development and creation of novel pesticides.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a pyrazolidine oxa(thia)diazole compound containing a pyridinium salt and a preparation method and application thereof. Background technique [0002] Plant diseases have always been one of the important restrictive factors for high-quality and high-yield crops. It is estimated that the average loss of major crops in the world accounts for about 10% to 15% of the total output, and the annual direct economic loss is as high as hundreds of billions of dollars. Among them, phytopathogenic bacteria and fungi are the most important factors that seriously threaten the production of food and crops in my country. In order to control bacterial and fungal diseases, it is urgent to prepare active small molecules that are highly effective against pathogenic bacteria and fungi. However, the activity of the currently used commercial antibacterial drugs is not efficient enough. Scre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A01P1/00A01P3/00
CPCC07D413/14
Inventor 杨松周磊王培义周健吴志兵薛伟
Owner GUIZHOU UNIV
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