Augmented multivariate image analysis applied to quantitative structure-activity relationship modeling of the phytotoxicities of benzoxazinone herbicides and related compounds on problematic weeds.
Two of major weeds affecting cereal crops worldwide are Avena fatua L. (wild oat) and Lolium rigidum Gaud. (rigid ryegrass). Thus, development of new herbicides against these weeds is required; in line with this, benzoxazinones, their degradation products, and analogues have been shown to be important allelochemicals and natural herbicides. Despite earlier structure-activity studies demonstrating that hydrophobicity (log P) of aminophenoxazines correlates to phytotoxicity, our findings for a series of benzoxazinone derivatives do not show any relationship between phytotoxicity and log P nor with other two usual molecular descriptors. On the other hand, a quantitative structure-activity relationship (QSAR) analysis based on molecular graphs representing structural shape, atomic sizes, and colors to encode other atomic properties performed very accurately for the prediction of phytotoxicities of these compounds against wild oat and rigid ryegrass. Therefore, these QSAR models can be used to estimate the phytotoxicity of new congeners of benzoxazinone herbicides toward A. fatua L. and L. rigidum Gaud.
Department of Forest Sciences, and ‡Department of Chemistry, Federal University of Lavras , 37200-000 Lavras, Minas Gerais (MG), Brazil.
Mirlaine R
MR
Freitas
Stella V B G
SV
Matias
Renato L G
RL
Macedo
Matheus P
MP
Freitas
Nelson
N
Venturin
D018554:Avena; D048588:Benzoxazines / Q000737:chemistry* / Q000494:pharmacology*; D006540:Herbicides / Q000737:chemistry* / Q000494:pharmacology*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D015999:Multivariate Analysis; D057685:Plant Weeds / Q000187:drug effects*; D006109:Poaceae / Q000187:drug effects; D021281:Quantitative Structure-Activity Relationship; D058728:Weed Control / Q000379:methods
D048588:Benzoxazines; D006540:Herbicides