Preparation and Root Growth-Modulatory Activity of N-Substituted 2-Acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides.

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  • KITAGAWA Tokujiro
    Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University
  • AKIYAMA Naohiro
    Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University
  • MASAI Katsunori
    Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University

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N-Substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides (8) were synthesized through the reaction of amines (13) with 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanoic acid (3b), which was prepared via condensation of 2-(bromomethyl)furan (10b) with diethyl acetamidomalonate, followed by partial hydrolysis of the resultant diethyl ester (3a) in the presence of barium hydroxide. However, bulky amines such as tert-butyl-amine or 2-trifluoromethylaniline did not afford the corresponding diamides (8). The biological activity of the prepared diamides (8) as root growth modulators was examined by germination assay using rape and leek seeds. N-(5-Bromo-2-thiazolyl)- and N-(4-chloro-2-benzothiazolyl)-2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides (8h, i) both potently inhibited the root growth of rape seedlings, but were less effective in the case of leek seeds. The herbicide 2, 4-dichlorophenoxyacetic acid completely inhibited root growth in both cases.

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