側鎖に芳香族アミド基あるいはアミノ基を含有するモノテルペニル誘導体とアダマンチル誘導体の合成とその生理活性

概要

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α-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〜3d, and 4a〜4d, and amines 6a〜10d. Twenty-four terpene derivatives obtained were tested for antimicrobial activity and growthregulating activity toward plants. As for activity of the former toward Bacillus subtilis, Staphylococcus 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〜10d, toward Tyrophagus putrescentiae and Dermatophagoides farinae were measured. On filter paper, compounds 6a, 6b, and 6c showed insecticidal activities of 92.4〜100% 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/m2 with these compounds in Table X, D. farinae was almost eradicated.
社団法人日本農芸化学会の論文
1996-04-01