Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Int J Mol Sci. 2023 Mar 17;24(6):5756. doi: 10.3390/ijms24065756.


A series of S-alkyl substituted thioglycolurils was prepared through the alkylation of corresponding thioglycolurils with halogenoalkanes and tested for their fungicidal activity against six phytopathogenic fungi from different taxonomic classes: Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum, and two pathogenic yeasts: Candida albicans and Cryptococcus neoformans var. grubii. A number of S-alkyl substituted thioglycolurils exhibited high activity against Venturia inaequalis and Rhizoctonia solani (85-100% mycelium growth inhibition), and moderate activity against other phytopathogens. S-Ethyl substituted thioglycolurils possessed a high activity against Candida albicans. Additionally, the hemolytic and cytotoxic properties of promising derivatives were determined using human red blood cells and human embryonic kidney cells, respectively. Two S-ethyl derivatives possessed both low cytotoxicity against normal human cells and high fungicidal activity against Candida albicans.

Keywords: Candida albicans; S-alkyl thioglycolurils; fungicidal activity; phytopathogenic fungi; tetrahydroimidazo[4,5-d]imidazol-2(1H)-ones; thioglycolurils.

MeSH terms

  • Antifungal Agents / pharmacology
  • Antineoplastic Agents* / pharmacology
  • Candida albicans
  • Fungal Genus Venturia
  • Humans
  • Rhizoctonia*
  • Structure-Activity Relationship


  • Antineoplastic Agents
  • Antifungal Agents

Supplementary concepts

  • Rhizoctonia solani
  • Venturia inaequalis

Grants and funding

This research received no external funding.