Inhibitory Activity of <i>N</i>-Substituted-2-piperidones with a 1, 4-Benzodioxan Ring on Germination of Barnyardgrass

DOI NDL Digital Collections JASI Web Site Web Site 1 Citations 3 References
  • TSUKADA Hidetaka
    Laboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
  • YAMADA Naotaka
    Laboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
  • HASHIMOTO Kazuki
    Laboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
  • TANIGUCHI Eiji
    Laboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
  • KUWANO Eiichi
    Laboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University

Bibliographic Information

Other Title
  • 1,4-ベンゾジオキサン環をもつ<i>N</i>-置換-2-ピペリドン類のヒエ種子発芽に対する阻害活性
  • Inhibitory Activity of N-Substituted-2-piperidones with a 1,4-Benzodioxan Ring on Germination of Barnyardgrass

Search this article

Abstract

A variety of 3-substituted-2-piperidones and related compounds were evaluated for their activity to inhibit germination of barnyardgrass (Echinochloa utilis) seeds. 3-[1-(1, 4-Benzodioxan-6-yl)-1-hydroxymethyl]-N-benzyl-2-piperidone (22) showed extremely high inhibitory activity. Studies on the structure-activity relationship indicated that a 1, 4-benzodioxan ring, a hydroxy substituent at the α-position of the benzyl group and a 2-piperidone ring were significant for higher activity. Of the compounds tested, 3-[1-(1, 4-benzodioxan-6-yl)-1-hydroxymethyl]-N-cinnamyl-2-piperidone (55) was the most effective, showing more than 90% germination inhibition at 1 nM. In both compounds 22 and 55, only erythro isomers inhibited germination of barnyardgrass seeds, while threo isomers were inactive even at 1μM. This result indicated that the stereochemistry of 1, 4-benzodioxan moiety in the erythro isomer, which is fixed by an intramolecular hydrogen bond between the hydroxy group and the carbonyl group, was essential for activity. The erythro-22 and 55 were less active against rice seeds when compared to barnyardgrass.

Journal

Citations (1)*help

See more

References(3)*help

See more

Keywords

Details 詳細情報について

Report a problem

Back to top