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KMID : 0903520040470040414
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Journal of the Korean Society of Agricultural Chemistry and Biotechnology
2004 Volume.47 No. 4 p.414 ~ p.421
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Understanding the Protox Inhibition Activity of Novel 1-(5-methyl-3- phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene Derivatives Using Comparative Molecular Similarity Indices Analysis (CoMSIA) Methodology
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Seong Nak-Do
Song Jong-Hwan
Park Kyeng-Yong
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Abstract
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3D QSAR studies for protox inhibition activities against root and shoot of the rice plant (Orysa sativa L.) and barnyardgrass (Echinochloa crus-galli) by a series of new 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives were conducted based on the results (Sung, N. D. et al.’s, (2004) J. Korean Soc. Appl. Biol. Chem. 47(3), 351-356) using comparative molecular similarity indices analysis (CoMSIA) methodology. Four CoMSIA models, without hydrogen bond donor field for the protox inhibition activities against root and shoot of the two plants, were derived from the combination of several fields using steric field, hydrophobic field, hydrogen bond acceptor field, LUMO molecular orbital field, dipole moment (DM) and molar refractivity (MR) as additional descriptors. The predictabilities and fitness of CoMSIA models for protox inhibition activities against barnyard-grass were higher than that of rice plant. The statistical results of these models showed the best predictability of the protox inhibition activities against barnyard-grass based on the cross-validated value r2 cv (q2= 0.635~0.924), non crossvalidated, conventional coefficient r2 ncv. value (r2= 0.928~0.977) and PRESS value (0.255~0.273). The protox inhibition activities exhibited a strong correlation with the steric (5.4~15.7%) and hydrophobic (68.0~84.3%) factors of the molecules. Particularly, the CoMSIA models indicated that the groups of increasing steric bulk at orthoposition on the C-phenyl ring will enhance the protox inhibition activities against barnyard-grass and subsequently increase the selectivity.
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KEYWORD
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3D-QSAR, 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluoro- benzenes, herbicidal activity, rice plant (Orysa sativa L.), barnyard grass (Echinochloa crus-galli), CoMSIA mode
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