Quinclorac계의 새로운 제초성 화합물을 탐색하기 위하여 기질 화합물로 3-phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole 유도체들을 합성하고 정량적인 구조와 벼(Or-yza sativa L.) 및 논피(Echinochloa crus-galli)에 대한 생장 저해활성($pI_{50}$)과의 관계(QSAR)를 분석하였다. 그 결과, 기질물질은 평면성 화합물로서 벼보다는 논피에 대하여 비교적 높은(논피>벼) 생장 저해활성을 나타내었으며 벼는 전자적 성질(줄기: ${sigma}_{opt.}=0.49$ 및 뿌리 $R_{opt.}=-0.15$)에 그리고 논피는 줄기와 뿌리, 두 부위 모두 소수성(${pi}_{opt.}=0.37{sim}2.40$)에 의존적이었다. QSAR 모델로부터 논피에 대한 선택성 조건은 ortho-치환된 전자 밀게로서 소수성(${pi}$)이 2.40인 치환체가 phenyl 고리상에 도입되는 경우이었다. 그리고 고활성 분자로서 예측된 2-tolyl 또는 3-tolyl 치환체(${Delta}pI_{50}=1.26$) 등은 선택성 징후가 엿보이는 화합물이었다.
To improve the growth inhibition activities and selectivities for quinclorac family, novel 3-substituted phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole derivatives as the substrate were synthesized and their the activities ($pI_{50}$) against shoot and root of rice plant (Oryza sativa L.) and barn-yard grass (Echinochloa crus-galli) were measured. And the quantitative structure-activity relationships (QSARs) between physicochemical parameters of the substitutents (R) on phenyl group and the activities ($pI_{50}$) were analyzed quantitatively. According to the SAR analyses, the substrates of planar conformation showed higher herbicidal activities against barnyard grass than rice plant. The activities against rice plant depend on the electronic effect (shoots: ${sigma}_{opt.}=0.49$ & root: $R_{opt.}=-0.15$) of substituents, whereas the activities against shoots and roots of barnyard grass depend on hydrophobicity (${pi}_{opt.}=0.37{sim}2.40$). There were conditions of selective growth inhibition activity against barnyard grass when such a ortho-substituted electron donating substituents showing the hydrophobicity value, ${pi}=2.40$ were introduced on the phenyl ring. The 2-tolyl substituent predicted from SAR equations was expected to have better growth inhibition activity and selectivity (${Delta}pI_{50}=1.26$) for barnyard grass.
