Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae

Fumiyuki Kiuchi, Satomi Nishizawa, Yoshisuke Tsuda, Hiromi Kawanishi, Sayuri Kinoshita, Miki Ishida, Noriko Sekino, Hisanao Ohsima, Akiyo Uchitani, Kaoru Kondo

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The nematocidal activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached a maximum at an optimal chain length and decreased in both shorter and longer homologues. The relationship between the activity and hydrophobicity of the homologues was analysed by the use of the bilinear model. The hydrophobicity of a compound, which gives a maximal activity, was similar for all neutral amides, but amides which have an additional amine group in the molecule had different values. Tertiary amines and their salts having a long alkyl chain also showed nematocidal activities comparable to those of the corresponding amides. The salts killed the larva at concentrations lower than their critical micell concentration, suggesting that they behave as a single molecule for the nematocidal action.

Original languageEnglish
Pages (from-to)3234-3244
Number of pages11
JournalChemical and Pharmaceutical Bulletin
Volume40
Issue number12
DOIs
Publication statusPublished - 1992 Jan 1
Externally publishedYes

    Fingerprint

Keywords

  • Keywords long chain amide
  • Toxocara canis
  • bilinear model
  • critical micell concentration
  • hydrophobic/hydrophilic balance
  • long chain amine
  • nematocidal activity
  • quantitative structure-activity relationship
  • structure-activity relationship
  • tetradecanamide

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Kiuchi, F., Nishizawa, S., Tsuda, Y., Kawanishi, H., Kinoshita, S., Ishida, M., Sekino, N., Ohsima, H., Uchitani, A., & Kondo, K. (1992). Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae. Chemical and Pharmaceutical Bulletin, 40(12), 3234-3244. https://doi.org/10.1248/cpb.40.3234