Preparation of N'-[2-(5,6-dimethylbenzothiazolyl)]-N-furfuryloxamide with plant growth regulatory activity.
The reaction of the N-furfuryloxamic acid sodium salt (12) with 1,1'-oxalyldiimidazole (ODI) yielded the imidazolide (13) as an intermediate, and this directly reacted with 2-aminothiazole derivatives (14) or 2-aminobenzothiazole derivatives (15) under essentially neutral conditions to afford the N'-12-(substituted thiazolyl)]- or N'-[2-(substituted benzothiazolyl)]-N'-furfuryloxamides (6 or 7). The prepared compounds (6 and 7) were examined for plant growth regulatory activity in a seed germination assay. The examination resulted in the discovery of some new revelations that N'-[2-(5,6-dimethylbenzothiazlyl)]-N-furfuryloxamide (7c) at the concentration of 1.0 x 10(-3) M completely inhibited the radicle growth of both rape and leek seedlings.
Kitagawa
T
T
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Japan. kitagawa@pharm.kobegakuin.ac.jp
Tsutsui
C
C
D000490:Allium / Q000187:drug effects / Q000254:growth & development; D001937:Brassica / Q000187:drug effects / Q000254:growth & development; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D063245:Plant Development; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000494:pharmacology; D010944:Plants / Q000187:drug effects; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
C419244:N'-(2-(5,6-dimethylbenzothiazolyl))-N-furfuryloxamide; D010937:Plant Growth Regulators; D013844:Thiazoles; D010072:Oxamic Acid