Abstract
Substituted phenylglyoxylonitrile oximino phosphates and thiophosphates invested as a synergist of molluscicide killing snail eggs have been exposed to the environment with very little attention. The partitioning properties, aqueous solubility (S w), n-octanol–water partition coefficient (K ow) and soil organic carbon sorption coefficients (K oc) of 16 O, O′-dialkyl, O″-(substituted phenylglyoxylonitrile oximino) phosphates and thiophosphates, were determined by the traditional shaking flask method. The parameters of molecular fragment connectivity indices (MFCIs) and linear solvation energy relationships (LSERs) were used as molecular descriptors to establish a series of correlation equations successfully. The obtained correlation equations provided a quantitative method to predict the three partitioning properties for new exploited substituted phosphates and thiophosphates. More valuable, the successful application of MFCIs provides us with a good example and a good idea to improve traditional molecular connectivity indices (MCIs).
Similar content being viewed by others
References
Allen, B. G., Robert, P. J., & Shirley, C. (2000). The role of traditional and novel toxicity test methods in assessing stormwater and sediment contamination. Critical Reviews in Environmental Science and Technology, 30, 413–437.
Bahnick, D. A., & Doucette, W. J. (1988). Use of molecular connectivity indices to estimate soil sorption coefficients for organic chemicals. Chemosphere, 17, 1703–1715.
Chen, J., Wang, D., Wang, S., Qiao, X., & Huang, L. (2007). Quantitative structure–property relationships for direct photolysis of polybrominated diphenyl ethers. Ecotoxicology and Environmental Safety, 66(3), 348–352.
Cope, L., Zhong, X., Garrett, E., & Parmigiani, G. (2004). MergeMaid: R tools for merging and cross-study validation of gene expression data. Statistical Applications in Genetics and Molecular Biology, 3, 342–246.
Dietrich, W. S., Dreyer, N. D., & Hansch, C. (1980). Confidence interval estimators for parameters associated with quantitative structure–activity relationships. Journal of Medicinal Chemistry, 23, 1201–1205.
Dongbin, W., Zhang, A., Wu, C., Han, S., & Wang, L. (2001). Progressive study and robustness test of QSAR model based on quantum chemical parameters for predicting BCF of selected polychlorinated organic compounds (PCOCs). Chemosphere, 44, 1421–1428.
Ernesto, E. (1999). Connectivity polynomial and long-range contributions in the molecular connectivity model. Chemical Physics Letter, 312(56), 556–560.
Famini, G. R., Aguiar, D., Payne, M. A., Rodriquez, R., & Wilson, L. Y. (2002). Using the theoretical linear energy solvation energy relationship to correlate and predict nasal pungency thresholds. Journal of Molecular Graphics & Modelling, 20(4), 277–280.
Famini, G. R., Penski, C. A., & Wilson, L. Y. (1992). Using theoretical descriptors in quantitative structure activity relationships: some physicochemical properties. Journal of Physical Organic Chemistry, 5, 395–408.
Fenner, K., Scheringer, M., Macleod, M., et al. (2005). Comparing estimates of persistence and long-range transport potential among multimedia models. Environmental Science and Technology, 39, 1932–1942.
Gramatica, P., Navas, N., & Todeschini, R. (1999). Classification of organic solvents and modeling of their physico-chemical properties by chemometric methods using different sets of molecular descriptors. TrAC Trends in Analytical Chemistry, 18(7), 461–471.
Gramatica, P., & Papa, E. (2005). An update of the BCF QSAR model based on theoretical molecular descriptors. QSAR &Combinatorial Science, 24, 953–960.
Gusten, H., Horvatic, D., & Sabljic, A. (1991). Modeling n-octanol/water coefficients by molecular topology: Polycyclic aromatic hydrocarbons and their alkyl derivatives. Chemosphere, 23, 299–313.
Hickey, J. P., & Passlno-Reader, D. R. (1991). Linear solvation energy relationships: “Rules of thumb” for estimation of variable values. Environmental Science & Technology, 25, 1753–1760.
Kier, L. B., & Hall, L. H. (1976). Molecular connectivity in chemistry and drug research. New York: Academic Press.
Kier, L. B., & Hall, L. H. (1981). Derivation and significance of valence molecular connectivity. Journal of Pharmaceutical Sciences, 70, 583–589.
Kier, L. B., & Hall, L. H. (1986). Molecular connectivity in structure–activity analysis. New York: Research Studies Press.
Klopman, G., & Stuart, S. E. (2003). Multiple computer-automated structure evaluation study of aquatic toxicity. III. Vibrio fischeri. Environmental Toxicology and Chemistry, 22(3), 466–472.
Nirmalakhandan, N. N., & Speece, R. E. (1988). Prediction of aqueous solubility of organic chemicals based on molecular structure. Environmental Science & Technology, 22, 328–338.
OECD (The Organization for Economic Cooperation and development) (1981). Guideline for testing of chemicals. Paris, 105.
Tehrany, E. A., Fournier, F., & Desobry, S. (2004). Simple method to calculate octanol–water partition coefficient of organic compounds. Journal of Food Engineering, 64(3), 315–320.
Valsaraj, K. T., Kommalapati, R. R., Robertson, E. D., & Constant, W. D. (1999). Partition constants and adsorption/desorption hysteresis for volatile organic compounds on soil from a Louisiana Superfund site. Environmental Monitoring and Assessment, 58(2), 227–243.
Wang, P. H., Leng, Z. K., & Xu, J. (1996). Synthesis of O,O′-dialkyl-O″-(substituted phenylglyoxylonitrile-oximino) phosphates and thiophosphates and their synergistic action with niclosamide as molluscicide. Acta Pharmaceutica Sinica. (in Chinese), 31, 918–924.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yuying, D., Guanghui, D., Ying, C. et al. Determination and estimation of partitioning properties for substituted phosphates and thiophosphates. Environ Monit Assess 152, 443–450 (2009). https://doi.org/10.1007/s10661-008-0328-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10661-008-0328-0