Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties

GRAPHICAL ABSTRACT

Abstract

A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, ¹H NMR, ¹³C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.

Keywords:

• Triazole
• thione derivatives
• piperazine
• Mannich reaction
• synthesis
• fungicidal activities

Funding

This work was supported by the National Natural Science Foundation of China (No. 21372133) and “111” Project of Ministry of Education of China (No. B06005).

Supplementary data

Figures S1–S4 and Table S1 are available online in Supplemental Materials.