Synthesis 2005(14): 2384-2392  
DOI: 10.1055/s-2005-870020
PAPER
© Georg Thieme Verlag Stuttgart · New York

Parallel Synthesis of a Library of Acylsemicarbazides Using a Solution-Phase One-Pot Method and Their Evaluation as Crop-Protection Agents

Justyna A. Grzyba, Mark A. Dekeyserb, Robert A. Batey*a
a Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada
Fax: +1(416)9785059; e-Mail: rbatey@chem.utoronto.ca;
b Crompton Co. Research Laboratories, Box 1120, Guelph, Ontario, N1H 6N3, Canada
Further Information

Publication History

Received 28 July 2004
Publication Date:
18 July 2005 (online)

Abstract

A solution-phase one-pot synthesis of a 40-member acylsemicarbazide library is outlined. The acylsemicarbazides were prepared by reacting various hydrazides with N,N′-carbonyldiimidazole (CDI) to generate 1,3,4-oxadiazole-2-one intermediates, which were then opened in situ with amines. Purification in the majority of cases was accomplished through filtration of the precipitated product in generally good yields and with ³ 95% purities. An analogous synthesis of acylthiosemicarbazides was accomplished using N,N′-thiocarbonyldiimidazole (TCDI). The library was then assayed for herbicidal, insecticidal, fungicidal and plant growth regulatory behavior.