Insecticidal Activity of Monoterpenoids Against Sitophilus zeamais Motschulsky and Tribolium castaneum Herbst: Preliminary Structure–Activity Relationship Study

To contribute to the search for effective substances in pest control, this study describes the fumigant and contact toxicity against <i>Tribolium castaneum</i> and <i>Sitophilus zeamais</i> of four essential oils (EOs) and some of their major chemical constituents. The EOs from <i>Tagetes zypaquirensis</i>, <i>Anethum graveolens</i>, <i>Satureja viminea</i> and <i>Minthostachys mollis</i> were obtained by steam distillation and chemically characterized using GC-MS. In the development of research, some monoterpenoids were isolated from the EOs, others were purchased commercially, and some were synthesized from the most active monoterpenoids present in EOs. The main components in the EOs were dill ether (28.56%), α-phellandrene (25.78%) and carvone (23.67%) for <i>A. graveolens</i>, piperitone oxide (30.40%) and pulegone (25.91%) in <i>M. mollis</i>, pulegone (37.40%) and p-menth-3-en-8-ol (11.83%) for <i>S. viminea</i>, and dihydrotagetone (32.13%), myrcene epoxide (19.64%) and β-myrcene (5.30%) for <i>T. zypaquirensis</i>. The results highlight the fumigant action (LC₅₀) and contact toxicity (LD₅₀) of EO from <i>M. mollis</i> against <i>T. castaneum</i> (LC₅₀ of 4.8 µL/L air and LD₅₀ of 6.5 µg/insect) and <i>S. zeamais</i> (LC₅₀ of 7.0 µL/L air and LD₅₀ of 5.81 µg/insect). Among the chemical constituents evaluated, R-carvone <b>2,</b> piperitone oxide <b>5</b> and R-pulegone <b>6</b> stand out for their insecticidal potential against <i>S. zeamais</i> (LC₅₀ between 3.0 and 42.4 µL/L, while LD₅₀ between 14.9 and 24.6 µg/insect) and <i>T. castaneum</i> (LC₅₀ between 2.2 and 4.8 µL/L, while LD₅₀ between 4.8 and 13.1 µg/insect). Preliminary structure-activity analysis suggests that the presence of the carbonyl group with conjugated double bonds in cyclic monoterpenes is important for the insecticidal potential exhibited.