Synthesis and Physiological Activity of Amides, Sulfides and Thiocyanates with an lonone Residue

Abstract

Synthesis and physiological activity of amides, sulfides and thiocyanates with an ionone residue was examined. α- and β-Ionones 1, 2 were converted to primary amines by a convenient method, followed by succesive reaction to afford objective amides, sulfides and thiocyanates. lonone 1 and 2 were converted to primary amines by oximation with hydroxylamine hydrochloride, followed by reduction with lithium aluminum hydride. These primary amine derivatives were finally transformed into amides lc-2f, sulfides 1h-2i and thiocyanates 1j-2j.
Sixteen ionone derivatives obtai ned were tested the efficiency for growth-regulating activity toward plants and antimicrobial activity. As activity of the former toward Lactuca sativa L., cv New York, lh-2h at 100 ppm indicated an inhibition of ca.90% toward root growth. As activity of the latter toward Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Aspergillus niger (A. niger), Penicillum citrinum (P. citrinum) and Fusarium oxysporum (F. oxysporum), 1, 1-Diisopropyl-3-{ (E) -1-methyl-3-[(R)-2, 6, 6-trimethyl-2-cyclohexen-1-yl] -2-propenyl} urea (1e), { (E) -1-methyl-3-[ (R) -2, 6, 6-trimethyl-2-cyclohexen-1-yl] -2-propenyl} aminomethyl thiocyanate (1j) and { (E) -1-methyl-3- [ (R) -2, 6, 6-trimethyl-2-cyclohexen-1-yl] -2-propenyl}aminomethyl thiocyanate (2j) (at0.01-0.001μg/mL) derived from 1 and 2 completely inhibited the growth of A. niger, P. citrinum and F. oxysporum.