Abstract
Eight deuterated derivatives of propyl cyclohexaneacetate were prepared in adequate purity and quantity. Their undeuterated counterparts were also prepared by the same synthetic routes. The apparatus and procedure for bioassay were devised to reveal the effect of deuteration on the attractiveness of the parent compound to the German cockroach. The insects were reared at 28-29°C in an open, flat cage (141×60 cm) provided with shelters, petri dishes containing caked food and water-wicked bottles along the back wall of the cage. They were conditioned to a constant, diffuse light of low intensity (10 lux at the bottom surface of the cage). Three traps; two treated with deuterated and undeuterated compounds, respectively and the third left untreated, were set in front of the shelters and exposed to the cockroaches for 30 min. The captures were counted. The tests were repeated 24 or 48 times, with the arrangement of the traps being altered. The results were analysed statistically. Propyl-3, 3, 3-d3 cyclohexaneacetate, propyl cyclohexane-1-d-acetate, propyl cyclohexane-2, 2, 6, 6-d4-acetate and propyl cyclohex-3, 3, 5, 5-ane-d4-acetate gave an activity improved over the undeuterated counterparts, whereas propyl cyclohexane-4-d2-acetate became less active. No activity change occurred with propyl-2, 2-d2 cyclohexaneacetate, propyl-1, 1-d2 cyclohexaneacetate and propyl cyclohexaneacetate-2, 2-d2.
