Synthesis and physiological activities of aromatic amides or aminos with monoterpenyl and adamantyl derivatives

alpha-Campholenic nitrile 1a, karahanaenone b, 1-adamantane carboxylic acid c and 2-bromoadamantane d were converted to primary amines by oximation (N, N-dimethyl hydrazonation, methylation, and elimination reaction) or nitration and reduction with LIAlH(4). These primary amine derivatives were-finally transformed into amides 3a similar to 3d, and 4a similar to 4d, and amines 6a similar to 10d. Twenty-four terpene derivatives obtained were tested for antimicrobial activity and growth-regulating activity toward plants. As for activity of the former toward Bacillus subtilis, Staphlococcus aureus, Escherichia coli, Aspergillus niger, Fusarium oxysporum, and penicillium citrinum, 6a, 8a, and 9a (at 100 ppm) derived from 2a, 2c, completely inhibited the growth of B. subtilis and S. aureus, and compounds 6c, and 10a, at 100 ppm inhibited the growth of B. subtilis. The insecticidal activities of these compounds, 3a similar to 10d, toward Tyrophagus putrescentiae and Dermatophagoides farinae were measured. On filter paper, compounds 6a, 6b, and 6c showed insecticidal activities of 92.4 similar to 100% at the concentration of 1.0 g/m(2) against T. putrescentiae and D. farinae. Toward T. putrescentiae the activity of these compounds was higher than that of N, N-diethyl-m-toluamide (DEET). At the concentration of 1.0 g/m(2) with these compounds in Table X, D. farinae was almost eradicated.