Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5–9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,8R)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
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We have newly prepared protic ionic liquids (PIL) composed of monoprotic alkylethylenediaminium (alkyl = N-hexyl and N-2-ethylhexyl) cations coupled with bis(trifluoromethanesulfonyl)amide anion (=TFSA) at room temperature. It is in contrast to the monoprotic N-hexylethylenediaminium (=HexH)TFSA salt which tends to crystallize on cooling that the monoprotic N-(2-ethylhexyl)ethylenediaminium (=EtHexH)TFSA salt assumes only a glassy state in solid. In the liquids, the HexH salt is more fluid than the EtHexH salt.
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