TY - DATA T1 - Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2‑Azolyl-3,4-dihydroquinazolines on Penicillium digitatum PY - 2016/02/19 AU - Wen-Jin Li AU - Qian Li AU - De-Li Liu AU - Ming-Wu Ding UR - https://acs.figshare.com/articles/journal_contribution/Synthesis_Fungicidal_Activity_and_Sterol_14_Demethylase_Binding_Interaction_of_2_Azolyl_3_4_dihydroquinazolines_on_Penicillium_digitatum/2441671 DO - 10.1021/jf305355u.s001 L4 - https://ndownloader.figshare.com/files/4084327 KW - compound 6 e KW - imidazolyl KW - IC KW - fungicidal activity KW - Penicillium digitatumA series KW - CYP 51 binding activity N2 - A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a–6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j–6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a–6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14α-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 μg/mL and the best CYP51 binding activity with Kd = 0.34 μg/mL, both superior to those of the agricultural fungicide triadimefon. ER -