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<p>The development of new fungicides for the treatment of agricultural diseases is a common goal due to the emerging resistance and low effectiveness of some common drugs. We designed new sub class of azole antifungal agents on the basis of 4-chloro-1,2,3-dithiazol-5-amine and azole parts. A four-stage method was proposed for the synthesis of new <i>N</i>-[2-(azol-1-yl)ethoxy]aryl-4-chloro-5<i>H</i>-1,2,3-dithiazol-5-imines. It based on synthesis of 2-, or 3-, or 4-nitro-(2-bromoethoxy)arenes then alkylation of azoles and reduction of nitro group. At the last step we modified substituted anilines by Appel’s salt (4,5-dichloro-1,2,3-dithiazol-1-ium chloride). The yield of the target imines ranged from 53 to 97%. It was also found that aromatic substitution of 1,3-dibromo-2-(2-bromoethoxy)-5-nitrobenzene occurs rather than bimolecular nucleophilic substitution of the halogen atom under conditions of the azole alkylation reaction. Thus, previously undescribed arylation products of 1-(2,6-dibromo-4-nitrogenyl)-1<i>H</i>-azoles (30–58%) and 1,1'-(2,6-dibromo-1,4-phenylene)bis(1<i>H</i>-1,2,4-triazole) (14%) were obtained. The high fungicidal activity of target imines was shown in vitro tests versus six species of phytopathogenic fungi. The synthesized compounds have higher activity than the reference agricultural drug, triadimefon, in relation to most types of phytopathogens. Especially target compounds effective vs. <i>Rhizoctonia solani</i> (EC<sub>50</sub> 10–21&#xa0;ppm) and <i>Venturia inaequalis</i> (EC<sub>50</sub> 11.6–150&#xa0;ppm).</p> Graphical abstract <p></p>

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Synthesis of novel azoles functionalized 4-chloro-1,2,3-dithiazol-5-imine derivatives and their antifungal activity

  • 期刊论文

  • 发表日期：

    2025年8月6日

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  • Elizaveta I. Bashkalova,
  • Grigory V. Tsaplin,
  • Anna L. Alekseenko,
  • Dmitry V. Minin,
  • Sergey V. Popkov

摘要

The development of new fungicides for the treatment of agricultural diseases is a common goal due to the emerging resistance and low effectiveness of some common drugs. We designed new sub class of azole antifungal agents on the basis of 4-chloro-1,2,3-dithiazol-5-amine and azole parts. A four-stage method was proposed for the synthesis of new N-[2-(azol-1-yl)ethoxy]aryl-4-chloro-5H-1,2,3-dithiazol-5-imines. It based on synthesis of 2-, or 3-, or 4-nitro-(2-bromoethoxy)arenes then alkylation of azoles and reduction of nitro group. At the last step we modified substituted anilines by Appel’s salt (4,5-dichloro-1,2,3-dithiazol-1-ium chloride). The yield of the target imines ranged from 53 to 97%. It was also found that aromatic substitution of 1,3-dibromo-2-(2-bromoethoxy)-5-nitrobenzene occurs rather than bimolecular nucleophilic substitution of the halogen atom under conditions of the azole alkylation reaction. Thus, previously undescribed arylation products of 1-(2,6-dibromo-4-nitrogenyl)-1H-azoles (30–58%) and 1,1'-(2,6-dibromo-1,4-phenylene)bis(1H-1,2,4-triazole) (14%) were obtained. The high fungicidal activity of target imines was shown in vitro tests versus six species of phytopathogenic fungi. The synthesized compounds have higher activity than the reference agricultural drug, triadimefon, in relation to most types of phytopathogens. Especially target compounds effective vs. Rhizoctonia solani (EC50 10–21 ppm) and Venturia inaequalis (EC50 11.6–150 ppm).

Graphical abstract