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2D-QSAR and HQSAR Analysis on the Herbicidal Activity and Reactivity of New O,O-dialkyl-1-phenoxy-acetoxy-1-methylphosphonate Analogues  

Sung, Nack-Do (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Jang, Seok-Chan (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Hwang, Tae-Yeon (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Publication Information
The Korean Journal of Pesticide Science / v.11, no.2, 2007 , pp. 72-81 More about this Journal
Abstract
Quantitative structure-activity relationships (QSARs) on the pre-emergency herbicidal activity and reactivity of a series of new O,O-dialkyl-1-phenoxyacetoxy-1-methylphosphonates (S) analogues against seed of cucumber (Cucumus Sativa) were discussed quantitatively using 2D-QSAR and HQSAR methods. The statistical values of HQSAR model were better than that of 2D-QSAR model. From the frontier molecular orbital (FMO) interaction between substrate molecule (S) and $BH^+$ ion (I) in PDH enzyme, the electrophilic reaction was superior in reactivity. From the effect of substituents, $R_2$-groups in substrate molecule (S) contributed to electrophilic reaction with carbonyl oxygen atom while X, Y-groups contributed to nucleophilic reaction with carbonyl carbon atom. And the influence of X,Y-groups was more effective than that of $R_2$-groups. As a results of 2D-QSAR model (I & II) and atomic contribution maps with HQSAR model, the more length of X, Y-groups is longer, the more herbicidal activity tends to increased. And also, the optimal ${\epsilon}LUMO$ energy, $({\epsilon}LUMO)_{opt.}$=-0.479 (e.v.) of substrate molecule is important factor in determining the herbicidal activity. It is predicted that the herbicidal activity proceeds through a nucleophilic reaction. From the analytical results of 2D-QSAR and HQSAR model, it is suggested that the structural distinctions and descriptors that contribute to herbicidal activities will be able to applied new herbicide design.
Keywords
O,O-dialkyl-1-phenoxyacetoxy-1-methylphosphonates; Reactivity; Herbicidal activity; 2D-QSAR & HQSAR analysis;
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