Comparative Molecular Similarity Indices Analyses (CoMSIA) on the Herbiridal Activities of New 5-benzofuryl-2-[1-(alkoxy-imino)alkyl]-3-hydroxycyclo-hex-2-en-1-one Derivatives

Three-dimensional quantitative structure-activity relationships (3D-QSARs) on the herbicidal activities against in-vitro pre-emergence rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) by new 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one derivatives were studied quantitatively using comparative molecular similarity indices analysis (CoMSIA) methodology. The optimized CoMSIA model(A5: $r^2_{cv.}=0.569$ & $r^2_{ncv.}=0.941$) for rice plant exhibited a good correlation with steric (31.6%) and hydrophobic (39.7%) factors of the substrate molecules, and the model (B4: $r^2_{cv.}=0.569$ & $r^2_{ncv.}=0.941$) for barnyardgrass exhibited a good correlation with electrostatic (46.7%) and H-bond acceptor field (30.8%), respectively. The predicted $R_1=SF_5,\;R_2=R_3=R_4=H(P1)$ substituent (Rice plant: $pI_{50}=4.84$ & Barnyardgrass: $pI_{50}=7.21$, ${\Delta}pI_{50}=2.37$) by the model (B4) not only exhibited to the highest herbicidal activity against barnyardgrass, but also exhibited to the highest selecticity between two plants.

새로운 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclo-hex-2-en-1-one 유도체들의 제초활성에 관한 비교분자 유사성지수 분석

새로운 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one 유도체들의 3차원적인 정량적 구조와 발아 전, 벼(Oryza sativa L.)와 논피(Echinochloa crus-galli)에 대한 제초활성과의 관계를 비교분자 유사성 지수분석(CoMSIA) 방법으로 연구하였다. 가장 양호한 CoMSIA 모델로서 벼에 대한 A5 모델($r^2_{cv.}=0.569$ 및 $r^2_{ncv.}=0.941$)은 주로 소수성장(39.7%)과 입체장(31.6%) 그리고 논피에 대한 B4 모델($r^2_{cv.}=0.595$ 및 $r^2_{ncv.}=0.933$)은 정전기장(46.7%)과 수소결합 받게장(30.8%)에 각각 의존적이었다. B4 모델에 의하여 예측된 $R_1=SF_5,\;R_2=R_3=R_4=H(P1)$ 치환체(벼: $pI_{50}=4.84$ 및 논피: $pI_{50}=7.21$, ${\Delta}pI_{50}=2.37$)는 논피에 대하여 가장 높은 제초활성을 나타내었으며 두 초종 간 선택성이 가장 큰 치환체이었다.