A series of novel cyclododecanone derivatives containing hydantoin/thiohydantoin were synthesized by the Wittig-Horner reaction and Knoevenagel condensation of α-substituted cyclododecanone and α-substituted 1,2-cyclododecandione prepared from cyclododecanone with hydantoin phosphate or thiohydantoin. Their structures were confirmed by IR, ¹H NMR, ¹³C NMR spectra and elemental analysis. The preliminary bioassay showed that some of compounds such as 10, 11A, 11B, 12A, 12B, 13A, 14B and 16 exhibited good to excellent fungicidal activities with the range of 70%～98% inhibitory ratio against Phomopsis asparagi, Phytophthora parasitica and Sclerotinia sclerotiorum at the concentration of 50 mg/mL, the precise determination of EC₅₀ data for 12B, 13A and 14B were 15.80, 31.34 and 44.26 mg/mL against P. asparagi, respectively.

Key words: α-substituted 1,2-cyclododecandione, Wittig-Horner reaction, knoevenagel condensation, fungicidal activity