Design, synthesis and Aphicidal activity of novel Pentafluorophenyl erivatives against Brevicoryne brassicae

Abstract

As the global population increases, food security becomes an urgent concern, with pest infestations posing a major threat to agricultural productivity. Brevicoryne brassicae, a harmful pest to cruciferous crops, not only damages plants directly but also acts as a vector for plant viruses. Over-reliance on pesticides has led to the development of pest resistance, prompting the need for novel insecticides. This study explores the incorporation of the pentafluorobenzene fragment, known for its electron-withdrawing properties and stability, into agricultural chemical molecules to enhance their insecticidal efficacy and combat resistance. A new class of compounds, combining pentafluorobenzene with pyrrole, was synthesized and evaluated for aphicidal activity against cabbage aphids. The results show that SO-type compounds exhibit potent insecticidal activity, with compound SO-3 outperforming imidacloprid in terms of aphid mortality and binding affinity to AChBP. Molecular docking analysis revealed that SO-3 forms six hydrogen bonds with AChBP, which may contribute to its superior efficacy. Additionally, pharmacokinetic modeling of SO-3 predicted favorable lipophilicity and promising oral bioavailability. These findings suggest that the pentafluorobenzene-containing compounds could provide a promising avenue for the development of more effective agrochemicals to address pest resistance and improve crop protection strategies.