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Design, Synthesis and Biological Evaluation of Isothiazole Based 1,2,4‐Trizaole Derivatives
Author(s) -
Chen Lai,
Wu Qifan,
Fan Zhijin,
Li Hongpeng,
Li Jiwei,
Hu Wenhao,
Liu Xiumei,
Belskaya Nataliya P,
Glukhareva Tatiana,
Zhao Bin
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700765
Subject(s) - chemistry , isothiazole , bioassay , in vivo , tobacco mosaic virus , proton nmr , fungicide , ethanol , carbon 13 nmr , stereochemistry , in vitro , nuclear chemistry , organic chemistry , biochemistry , virus , genetics , microbiology and biotechnology , botany , virology , biology
A series of novel 3,4‐dichloroisothiazole based 1,2,4‐triazole derivatives were rationally designed and synthesized. Their structures were confirmed by 1 H NMR, 13 C NMR, HRMS or elemental analysis; the typical crystal structure was determined by X‐ray diffraction for validation. All target compounds were evaluated for their in vitro fungicidal and in vivo anti‐TMV activities. The bioassay results indicated that compound 6b , namely 1‐(3,4‐dichloroisothiazol‐5‐yl)‐1‐(4‐fluorophenyl)‐2‐(1 H ‐1,2,4‐triazol‐1‐yl)ethanol, exhibited excellent growth inhibition against B. cinerea, C. arachidicola and P. piricola with median effective concentrations (EC 50 ) of 6.98, 2.73 and 3.07 μg/mL, respectively, and good in vivo anti‐TMV activity of over 60% of inactivation and induction activity at 100 μg/mL. These data demonstrate that compound 6b is both a fungicide and an anti‐TMV lead, deserving further studies.