Synthesis and Fungicidal Activity of Novel 1,3-Disubstituted 1H-Diazirine Derivatives

A convenient method for synthesis of novel 1-[pyrimidinyl], 1-[1,3,5-triazin-2-carbonyl], and 1-[thiazol-5-carbonyl] derivatives of 3-thioxo-diaziridine 1, 3, 5, and 7 from corresponding hydrazides, CS2, and KOH is elaborated. The highest reaction yield was observed when these initial reagents were taken in molar ratio of 1:1.7:2.0, respectively. By alkylation of compounds 1, 3, 5, and 7 that proceeds exclusively at sulfur atom, the 3-sulfanyl derivatives of 1-[pyrimidinyl]-, 1-[1,3,5-triazin-2-carbonyl]-, and 1-[thiazol-5-carbonyl]-diazirines 2, 4, 6, and 8 were formed. The structures of synthesized compounds were confirmed by proton and carbon nuclear magnetic resonance (NMR), mass spectra (MS), and elemental analysis. The fungicidal activities of S-substituted derivatives were studied. Data of preliminary biological tests testify that these compounds can be of interest in search for new fungicides.