Abstract
Pyrrolidone-anilide derivatives from L-glutamic acid and anilines were synthesized as follows: The products were identified by elementary analysis, IR, NMR and Mass spectra with (R)-2-pyrrolidone-5-carbox-anilide, (R)-2-pyrrolidone-5-cabox-p-chloroanilide, (R)-2-pyrrolidone-5-carbox-o-toluidide, (R)-2-pyrrolidone-5-carbox-m-toluidide and (R)-2-pyrrolidone-5-carbox-p-toluidide. The products were testes for their phytotoxicity on the germination and the seedling growth of radish and rice plants. Among them, (R)-2-pyrrolidone-5-carbox-anilide and (R)-2-pyrrolidone-5-carbox-p-chloroanilide derivatives were strongly inhibitory especially on the germination and the seedling growth of radish seeds. All the compounds also showed an inhibitory activity upon the germination of rice seeds. Additionally, the inhibiting rate of radish growth differs according to the isomeric position(ortho, meta and para) of the methyl group; (R)-2-pyrrolidone-5-carbox-m-toluidide derivative was more effective than both (R)-2-pyrrolidone-5-carbox-o-toluidide and (R)-2-pyrrolidone-5-carbox-p-toluidide derivatives.
L-Glutamic acid와 aniline 誘導體로부터 다음과 같은 새로운 pyrrolidone-anilide誘導體를 合成했다. 이 化合物들의 構造가 元素分析, UV, IR, NMR 그리고 Mass 스펙트럼으로 (R)-2-pyrrolidone-5-carbox-p-chloroanilide, (R)-2-pyrrolidone-5-carbox-o-toluidide, (R)-2-pyrrolidone-5-carbox-m-toluidide, (R)-2-pyrrolidone-5-carbox-p-toluidide임이 확인되었다. 이 化合物들의 무우, 벼 種子發芽와 生育에 대한 phytotoxicity을 調査한 結果는 다음과 같다. 이 化合物들은 벼 種子에 대하여 發芽 및 發根抑制?果를 나타내었다. 그 중에서 (R)-2-pyrrolidone-5-carboxanilide와 (R)-2-pyrrolidone-5-carbox-p-chloroanilide 誘導體는 무우 種子의 發芽와 生育을 현저하게 抑制하였다. 또한 (R)-2-pyrrolidone-5-carboxtoluidide 誘導體에 있어서 methyl group의 結合位置 (ortho, meta, para)에 따라서 무우의 生育抑制率이 다르다는 것을 알았다. 즉 (R)-2-pyrrolidone-5-carbox-m-toluidide는 (R)-2-pyrrolidone-5-carbox-o-toluidide와 (R)-2-pyrrolidone-5-carbox-p-toluidide 보다 무우 種子의 生育阻害現象이 현저하였다.