2003 Volume 52 Issue 1 Pages 41-46
The monoterpene aldehydes, (-)-perillaaldehyde [1], (-)-myrtenal [2], were converted to nitriles by sequential N,N-dimethylhydrazonation, methylation and a Hofmann-type elimination reaction. The nitriles were subsequently converted to terpenoyl chlorides by hydroysis and chlorination with thionyl chloride. The chlorocarbonylated terpenes were condensed with pyrrolidine, 2-, 3-, or 4-methylpiperidines, and 2,6- or 3,5-dimethylpiperidines to produce 14 terpeneamides [1a]-[2g] in 42-87% overall yields in four steps starting with imidation of the terpene aldehydes. 1-Adamantanecarboxylic acid [3] and 1-adamantaneacetic acid [4] were condensed with pyrrolidine, 2-, 3-, or 4-methylpiperidines, and 2,6- or 3,5-dimethylpiperidines to afford 14 adamantane amides [3a]-[4g] in 41-90% overall yields in one step starting from adamantane derivatives. Miticidal activity of amide compounds [1a]-[4g] toward Tyrophagus putrescentiae and Dermatophagoides farinae was assessed. On filter paper, amide compounds [2a]-[2g] from [2] showed miticidal activity exceeding that of N,N-Dimethyl-m-toluamide (DEET) toward T. putrescentiae. On filter paper amide compounds [1c]-[1e] from [1] and [2a]-[2g] from [2] and showed [3b], [3d], [3e] from [3] and [4a], [4b], [4d], [4f], [4g] from [4] indicated greater miticidal activity compared to DEET for D. farinae.
