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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 25, Number 1
JKCSEZ 25(1)
February 20, 1981 

Syntheses of Anilide Derivatives from Amino Acids ad Their Biological Activities (Ⅰ). Preparation of (R)-2-Pyrrolidine-5-carbox-anilide Derivatives and Their Effects on the Germination of Plant Seeds

Amino산으로부터 Anilide유도체의 합성과 생리활성에 관한 연구 (제1보). (R)-2-Pyrrolidone-5-carbox-anilide 유도체의 합성과 식물종자발아에 미치는 영향
Chun-Soo Lee

L-Glutamic acid와 aniline 유도체로부터 다음과 같은 새로운 pyrrolidone-anilide유도체를 합성했다. 이 화합물들의 구조가 원소분석, UV, IR, NMR 그리고 Mass 스펙트럼으로 (R)-2-pyrrolidone-toluidide, (R)-2-pyrrolidone-5-carbox-p-toluidide임이 확인되었다. 이 화합물들의 무우, 벼 종자발아와 생육에 대한 phytotoxicity을 조사한 결과는 다음과 같다. 이 화합물들은 벼 종자에 대하여 발아 및 발근억제효과를 나타내었다. 그 중에서 (R)-2-pyrrolidone-5-carboxanilide와 (R)-2-pyrrolidone-5-carbox-p-chloroanilide 유도체는 무우 종자의 발아와 생육을 현저하게 억제하였다. 또한 (R)-2-pyrrolidone-5-carboxtoluidide 유도체에 있어서 methyl group의 결합위치 (ortho, meta, para)에 따라서 무우의 생육억제율이 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 종자의 생육조해현상이 현저하였다.

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.

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