Synthesis, structures, and biological activities of new 1<i>H</i>‐1,2,4‐triazole derivatives containing pyridine unit

Li, Jianbing; Tao, Weifeng; Dai, Hong; Jin, Zhong; Fang, Jianxin

doi:10.1002/hc.20308

Cited by 14 publications

(4 citation statements)

References 17 publications

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“…When using liquid brine in the bromination step, a complex mixtures were monitored by TLC (Thin layer chromatography), then replacement of the bromination reagent with NBS/TMSOTf afforded the desired product 2 in good yield. Although there are many approaches for synthesizing 1,2,4-triazole [18,19], the simplest one is the N-alkylation of sodium salt of triazole with halides [20]. Subsequently, the condensation reaction of ketone 3 with O-substituted hydroxylamine hydrochloride led to the key intermediate oxime ether 4.…”

Section: Synthesismentioning

confidence: 99%

Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

et al. 2020

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A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

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Section: Synthesismentioning

confidence: 99%

Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

et al. 2020

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“…2H-1,4-Benzothiazine derivatives have attracted much interest in modern society due to their biological properties [1]. On the other hand, 1,2,4-triazole derivatives are one of the most widely used fungicides due to their high efficiency, low toxicity, and absorbent properties [2][3][4]. For example, 2H-1,4-benzothiazine derivatives can be used as central nervous system depressants, ataractic agents, antispasmodics, and ciliary relaxants for pseudomyopia and eye fatigue [5].…”

Section: Introductionmentioning

confidence: 99%

A convenient synthesis of 2‐(1H‐1,2,4‐triazol‐1‐yl)‐2H‐1,4‐benzothiazine derivatives

Zhong

Sun

2008

Heteroatom Chemistry

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“…On the other hand, 1,2,4‐triazole derivatives exhibit broad‐spectrum bioactivity and are widely used in agrochemicals and pharmaceuticals . Fungicides containing triazoles, for example, flusilazole, triadimenol, and propiconazole, are the most effective plant protection agents against plant pathogens such as Xanthomonas oryzae pv.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

Liao

Zhou

Xiao

et al. 2016

Journal of Heterocyclic Chem

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A series of 2‐substituted phenoxy‐N‐(4‐substituted phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazole‐2‐yl)acetamide derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r, 8s, 8t was synthesized by the reaction of phenoxyacetyl chloride 7 with intermediate 4‐substituted phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐amine 5. Their structures were confirmed by 1H NMR, 13C NMR, MS, IR, and elemental analyses. The synthesized compounds were also screened for their antimicrobial activity against three types of plant fungi (Gibberella zeae, Phytophthora infestans, and Paralepetopsis sasakii) and two kinds of bacteria [Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac)] showing promising results. In particular, 8b, 8f, 8g, and 8h exhibited excellent antibacterial activity against Xoo, with 50% effective concentration (EC50) values of 35.2, 80.1, 62.5, and 82.1 µg/mL, respectively, which are superior to the commercial antibacterial agent bismerthiazol (89.9 µg/mL). The preliminary structure–activity relationship studies of these compounds are also briefly described.

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Synthesis, structures, and biological activities of new 1H‐1,2,4‐triazole derivatives containing pyridine unit

Cited by 14 publications

References 17 publications

Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

A convenient synthesis of 2‐(1H‐1,2,4‐triazol‐1‐yl)‐2H‐1,4‐benzothiazine derivatives

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

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