The cyclic monoterpenoids karahanaenone (1) and (-) -perillaldehyde (2) were converted to primary amines by a convenient method, followed by succesive reaction to afford objective ureas, amides and amines. (1) was converted to primary amine by oximation with hydroxylamine hydrochloride, and reduction with lithium aluminum hydride (LAH). (2) was converted to primary amine by nitrilation (N, N-dimethylhydrazonation, methylation, and elimination reaction), and reduction with LAH. These primary amine derivatives were finally transformed into ures (3) (5), (10) and (11), amides (6) (8), (12) (16), and amines (9), (17).
Fifteen terpene derivatives obtained were tested the efficiency for antimicrobial activity and growth-regurating activity toward plants. As activity of the former toward Bacillus subtilis, Esherichia coli, Aspergillus niger, Penicillium citrium and Fusarium oxysporum, N- (1, 8-p-menthadien-7-yl) -N', N'-diethylurea (11) and N- (1, 8-p-menthadien-7-yl) -benzyloxy-methylamide (13) (at 50100 ppm) derived from (2) completely inhibited the growth of B. subtilis and A. niger. As activity of the latter toward Brassica Rapa, N- (1, 8-p-menthadien-7-yl) α-styrylamide (14) at 100 ppm indicated an inhibition of ca. 50 % toward root growth.
