(Z)-II-Tetradecenyl acetate is the reported sex pheromone of European corn borer and redbanded leafroller moths. However, geometrically pure preparations of the compound are weakly attractive to these species. Presence of the E geometrical isomer in the Z is necessary for maximum sex attraction and these moths are "tuned" to respond optimally to specific proportions of Z to E. This discovery is important to considerations of moth pheromonal specificity, evolution, and in application of knowledge of the pheromones to insect-pest suppression.

A sex pheromone of the sweetpotato weevil,Cylas formicarius elegantulus (Summers), was obtained from collections of volatiles from virgin females, and pheromone was isolated by means of liquid and gas chromatography. The purification procedure was monitored by quantitative laboratory and field bioassays and the compound was identified as (Z)-3-dodecen-1-ol (E)-2-butenoate by means of spectroscopic and microchemical methods. Synthesis, followed by laboratory and field bioassays, showed that the biological activity of the synthetic material was qualitatively and quantitatively indistinguishable from that of the purified natural product.

N-Acetylmethanopyrrolidine and its four 5-syn/anti-fluoro and hydroxy derivatives have been synthesized from 2-azabicyclo[2.2.0]hex-5-ene, a 1,2-dihydropyridine photoproduct. These conformationally constrained mimics of idealized Cβ-gauche and Cβ-anti conformers of pyrrolidines were prepared in order to determine the inherent bridge bias and subsequent heteroatom substituent effects upon trans/cis amide preferences. The bridgehead position and also the presence of gauche(syn)/anti-5-fluoro or 5-hydroxy substituents have minimal influence upon KT/C values of N-acetylamide conformers in both CDCl3 (43–54% trans) and D2O (53–58% trans). O-Benzoylation enhances the trans amide preferences in CDCl3 (65% for a syn-OBz, 61% for a trans-OBz) but has minimal effect in D2O. The synthetic methods developed for N-BOC-methanopyrrolidines should prove useful in the synthesis of more complex derivatives containing α-ester substituents. The KT/C results obtained in this study establish baseline amide preferences that will enable determination of contributions of α-ester substituents to trans-amide preferences in methanoprolines.