Design,Synthesis and Bioassay of 2-Phenylglycine Derivatives as Potential Pesticide Candidates

Plant diseases can seriously affect the growth of food crops and economic crops. To date, pesticides are still among the most effective methods to prevent and control plant diseases worldwide. Consequently, to develop potential pesticide molecules, a series of novel 2-phenylglycine derivatives containing 1,3,4-oxadiazole-2-thioethers were designed and synthesized. The bioassay results revealed that G₁₉ exhibited great in vitro antifungal activity against Thanatephorus cucumeris with an EC₅₀ value of 32.4 μg/mL, and in vivo antifungal activity against T. cucumeris on rice leaves at a concentration of 200.0 μg/mL (66.9 %) which was close that of azoxystrobin (73.2 %). Compounds G₂₄ (80.2 %), G₂₅ (89.4 %), and G₂₇ (83.3 %) exhibited impressive in vivo inactivation activity against tobacco mosaic virus (TMV) at a concentration of 500.0 μg/mL, which was comparable to that of ningnanmycin (96.3 %) and markedly higher than that of ribavirin (55.6 %). The antibacterial activity of G₁₆ (63.1 %), G₂₆ (89.9 %), G₂₇ (78.0 %), and G₂₈ (68.0 %) against Xoo at a concentration of 50.0 μg/mL was higher than that of thiadiazole copper (18.0 %) and bismerthiazol (38.9 %). Preliminary mechanism studies on the antifungal activity against T. cucumeris demonstrated that G₁₉ can affect the growth of mycelia by disrupting the integrity of the cell membrane and altering the permeability of the cell. These studies revealed that the amino acid derivatives containing a 1,3,4-oxadiazole moiety exhibited certain antifungal, antibacterial, and anti-TMV activities, and these derivatives can be further modified and developed as potential pesticide molecules.