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Comparative Molecular Field Analyses (CoMFA) Models and Their Selectivity for the Herbicidal Activities of New Novel 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one Derivatives  

Sung, Nack-Do (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Song, Jong-Hwan (Cytosine Laboratory, Korea Research Institute of Chemical Technology)
Kang, Eun-Kyu (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Jung, Hoon-Sung (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Publication Information
Applied Biological Chemistry / v.48, no.4, 2005 , pp. 394-399 More about this Journal
Abstract
The comparative molecular field analyses (CoMFA) models for the herbicidal activities against barnyardgrass (Echinochloa crus-galli) and rice plant (Orysa sativa L.) by the substituent (R) on the hexahydroisoindol-1-one ring in a series of new 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one derivatives were conducted and discussed for selectivity between both plants. The statistical results of the two best models (B2 & R7) showed the best predictability for the herbicidal activities based on the cross-validated value $q_2(r^2cv.=0.529{\sim}0.755)$ and none cross-validated value $({r^2}_{ncv.}=0.937{\sim}0.945)$, respectively. Based on the findings, the predictability and fitness of the model (B2) for barnyard grass was better than that of the model (R7) for rice plant. From the two models and contour maps, it is revealed that the novel selective character for herbicidal activity between the two plants depend on the electrostatic field and steric field for the substituent of ortho-positions on the S-phenyl group as R-substituent in hexahydroisoindol-1-one ring.
Keywords
Barnyardgrass (Echinochloa crus-galli); rice plant (Orysa sativa L.); 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-ones; selective herbicidal activity; CoMFA model; 3D-QSAR;
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