Citation: Chun-Nong WANG, Tai-Ning ZENG, Sheng-Nan LI, Wan LI, Long-Fei LI, Fei CAO, Zi-Hui YANG. Preparation, Crystal Structure and Fungicidal Activity of N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide Compounds[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220321. doi: 10.14102/j.cnki.0254-5861.2011-3326 shu

Preparation, Crystal Structure and Fungicidal Activity of N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide Compounds

Chun-Nong WANG ^{a, †} ,
Tai-Ning ZENG ^{a, †} ,
Sheng-Nan LI ^a ,
Wan LI ^a,, ,
Long-Fei LI ^a ,
Fei CAO ^a ,
Zi-Hui YANG ^b

a.
College of Pharmaceutical Sciences, Key Laboratory of Analytical Science and Technology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding 071002, China
b.
Shan Dong Jinhuahai Biotechnology Co., Ltd Jinan 251400, China

Corresponding author: Wan LI, liwanjingmin@163.com
Received Date: 17 June 2021
Accepted Date: 16 October 2021

Fund Project: the Scientific Research Foundation of Hebei Educational Committee QN2019058Natural Science Foundation of Hebei Province of China H2021201059

Figures(6)

A variety of new N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide compounds (8a-i) were synthesized through four steps from benzofuranol as raw materials. The crystal structure of compound 8a (C₁₇H₂₁N₃O₃S, M_r = 347.43) was measured by X-ray diffraction, which was classified as monoclinic system, Z = 4, V = 1742.72(8) Å³, D_c = 1.324 Mg/m³, F(000) = 736, S = 1.03, μ = 0.21 mm^-1, space group P2₁ with a = 9.9177(3), b = 8.9519(2), c = 19.8679(5) Å, the final R = 0.035 and wR = 0.105 for 3873 observed reflections (I > 2σ(I)). The X-ray structure presented N(3)–H(3)···N(2) and C(6)–H(6)···O(3) intermolecular hydrogen bonds, which acted as an important role in stabilizing the crystal structure. Additionally, preliminary biological assay on compound 8a showed good fungicidal activity in vivo, with the inhibition of 75% against Pseudoperonospora cubensis at 200 mg/L.
- N-(5-(benzofuranol-7-oxymethyl)-1,3,4-thiadiazol-2-yl)amide,
- preparation,
- crystal structure,
- antifungal activity
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