Synthesis, Characterization, and Herbicidal Activities of New 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, and 1,2,4-Triazoles Derivatives Bearing (R)-5-Chloro-3-fluoro-2-phenoxypyridine

Synthesis of some novel 1,2,4-triazoles, 1,3,4-oxadiazoles and 1,3,4-thiadiazoles bearing a (R) 5-(1-(4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy)ethyl) unit, as a moiety of commercial herbicide, using their thiosemicarbazides in an alkaline, iodine and acidic media is reported, respectively. The structure of the synthesized compounds was characterized by IR, ¹H, ¹³C NMR spectroscopic data, and elemental analyses. The herbicidal activities of synthesized compounds were evaluated against Echinochloa cruss-galli, Avena fatua, and Sorgum halepense weeds. Compounds 7 and 12a showed potential herbicidal activity against gramineous weeds. Our results may provide some guidance for synthesis development of some novel oxa or thiadiazole and triazole-based herbicidal lead structures.