Synthesis and Antifungal Activity of 1,3-substituted-5-chloropyrazole-4-carboxylic acid Oxime Esters

1,3-치환-5-chloropyrazole-4-carboxylic acid oxime ester의 합성과 살균력

A series of novel 1,3-substituted-5-chloropyrazole-4-carboxylic acid oxime esters was synthesized. Their chemical strictures were elucidated on $^1H,\;^{13}C-NMR$ and IR spectra, Fifteen such compounds were screened for their antifungal activity against R. solani, P. oryzae, B. cinerea, P. graminearum, P. capsici and G. cingulata. The results showed that pyrazole-oxime esters with electron withdrawing groups(III, XIII, XIV) had better biological activities than these with electron releasing groups.

생리활성을 갖는 신규물질 탐색의 일환으로 1,3 치환 -5-chloropyrazole-4-carbonyl chloride를 합성한 뒤 8종의 aldoxime 또는 ketoxime과 친핵 반응시켜 15종의 pyrazole-oxime ester를 얻었으며, 이들의 구조를 $^1H,\;^{13}C-NMR$ 및 IR 등으로 확인하였다. 이 유도체들의 R. solani, P. oryzae, B. cinerea, P. graminearum, P. capsici 및 G. cingulata에 대한 균사생육억제효과를 검정한 결과, oxime 부위$(R^3)$가 친전자성기로 치환된 방향족인 경우가(III, XIII, XIV) 포화알킬기인 경우보다 우수한 효과를 보여주었다.