SYNTHESIS, CHARACTERIZATION AND INSECTICIDAL ACTIVITY OF A SERIES OF ETHYL 3-(ARYL)-1,2,4-OXADIAZOLE-5-CARBOXYLATE.
Keywords: 1,2,4-oxadiazole, Plutella xylostella, new insecticides.
Plutella xylostella, known as the diamondback moth, is an insect pest that affects several cruciferous vegetable crops and is responsible for economic losses estimated at billions of dollars annually spent on pest control and crop losses. With the indiscriminate use of broadspectrum insecticides, P. xylostella has developed cross-resistance to the main active ingredients commercially available as a form of natural protection, in addition to harming natural enemies and the environment. This scenario has contributed to the search for the environmentally friendly development of new active molecules that can mitigate this resistance and control the pest. The heterocycle 1,2,4-oxadiazole is a promising compound with numerous known biological activities, including insecticidal activity against pests. Knowing this, new 1,2,4-oxadiazoles will be developed from a sequence of steps aimed at obtaining the respective synthetic intermediates to obtain the desired compounds. The first step consisted of the preparation of aryl-amidoximes (Ph, p-NO2, p-Cl, p-Br, m-toluene, p-pyridinyl, and mpyridinyl) from aryl-nitriles (Ph, p-NO2, p-Cl, p-Br, m-toluene, p-pyridinyl, and m-pyridinyl), with yields reaching 90%. The respective amidoximes were then reacted with the ethyl chloroxoacetate ester to obtain 1,2,4-oxadiazoles in 80% yields. The third step consisted of the esterification reaction of ferulic acid in 98% yield. To date, intermediates for the target compounds have been synthesized in 90% yields, confirming that the methodological strategies addressed, which aim to obtain the target compounds through cleaner, more efficient, and faster routes, can be an excellent way to obtain the final compounds.