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Qsar analysis of the chemical hydrolysis of organophosphorus pesticides in natural waters Kenneth K. Tanji, University of California, Davis Jonathan J. Sullivan, University of California, Davis UC Water Resources Center Technical Completion Report W-843
ABSTRACT: Statistical techniques for screening experimental or literature chemical databases for
compounds exhibiting potential environmental activity are becoming increasingly utilized in
environmental analysis as pragmatic and economical complementary tools to enhance or augment
costly traditional analytical procedures. Utilizing the predictive modeling approach, it is often
argued, implicitly permits an unlimited number of chemicals to be screened for specific behavioral
or physicochemical characteristics in a variety of environmental and biological matrices,
consequentially conserving the financial resources for exhaustive testing, yet providing a
methodology that helps to insure that questionable compounds are more thoroughly tested.
Moreover, such techniques provide a database of exhaustive test results from which investigators
and regulators can extract relevant information for further research or decision-making.
To assess the efficiency of statistical modeling methods for predicting chemical processes
in the environment, a one-year exploratory study utilizing Quantitative Structure-Activity
Relationship (QSAR) methodology to obtain linear model equations for estimating the rates of
chemical hydrolysis of several organophosphorus (OP) pesticides in natural river waters has been
conducted. This modeling effort specifically considers the effects of chemical structure on
reactivity and utilizes connectivity parameters from graph theory as quantitative structural
descriptors. Derived model equations were examined to establish whether quantitative correlations
between fundamental molecular characteristics and observed hydrolytic properties were possible.
Inconclusive results for a training set of six OP pesticides indicate that there are inherent
weaknesses in molecular connectivity theory when applied to complex reaction parameters that
require further exploration. The inherent complexity of most chemical reaction mechanisms and
the indistinct influence of both adjoining and distant atoms in the molecular environment makes it
difficult for a single descriptor, even one as widely successful as connectivity indices, to
adequately account for definitive structural characteristics of molecules. It is apparent from results
of this study that molecular connectivity indices alone are often not discriminating enough
descriptors for procuring comprehensive structure-property relationships beyond a rather restricted
range of structural variation, at least when characterizing chemical reaction parameters.
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