Peculiarities of extraction of organophosphorus pesticides and its description from the perspective of the principle of additivity of Gibbs energy of distribution

  • Mikhail F. Zayats The institute of plant protection, Mira Street, 2, 223011, Priluki, Minsk district, Minsk region
  • Sergey M. Leschev Belarusian State University, Nezavisimosti avenue, 4, 220030, Minsk
  • Siarhei F. Furs Belarusian Medical Academy of Post-Graduate Education, P. Broŭki Street, 3/3, 220013, Minsk
  • Vyacheslav V. Zhylko Belarusian State University, Nezavisimosti avenue, 4, 220030, Minsk

Abstract

The distribution of a number of organophosphorus pesticides of different classes (phosphates, thiophosphates, dithiophosphates, phosphonothioates, phosphonodithioates, phosphoramidates, phosphoramidothioates) was studied at 20 ± 1 °C in extraction systems hexane – water, hexane – ethylene glycol, hexane – acetonitrile, hexane – a mixture of acetonitrile and water and hexane – a mixture of acetonitrile and ethylene glycol. The distribution constants (P) of the pesticides and the values of the functional groups increments (If) between hexane and the polar phase were calculated. The factors that affect these values are discussed. The possibility of prediction of change of the pesticide distribution constants at introduction or replacement of one functional group to another is considered on the basis of the principle of additivity of Gibbs energy of distribution, or the method of group increments. The factors affecting the deviation of the calculated distribution constants of substances from the experimental constants are determined. The influence of the polar phase composition on the change of functional group increments and pesticide distribution constants are considered.

Author Biographies

Mikhail F. Zayats, The institute of plant protection, Mira Street, 2, 223011, Priluki, Minsk district, Minsk region

PhD (chemistry); leading researcher at the laboratory of pesticide dynamics

Sergey M. Leschev, Belarusian State University, Nezavisimosti avenue, 4, 220030, Minsk

doctor of science (chemistry); professor at the department of analytical chemistry, faculty of chemistry

Siarhei F. Furs, Belarusian Medical Academy of Post-Graduate Education, P. Broŭki Street, 3/3, 220013, Minsk

PhD (chemistry), docent; associate professor at the department of hygiene and medical ecology, faculty of public health and healthcare management

Vyacheslav V. Zhylko, Belarusian State University, Nezavisimosti avenue, 4, 220030, Minsk

PhD (chemistry); associate professor at the department of analitycal chemistry, faculty of chemistry

References

  1. Leo A., Hansch C., Elkins D. Partition coefficients and their uses. Chem. Rev. 1971. Vol. 71, issue 6. P. 525–616. DOI: 10.1021/cr60274a001.
  2. Leo A. J. Calculating log Poct from structures. Chem. Rev. 1993. Vol. 93, issue 4. P. 1281–1306. DOI: 10.1021/cr00020a001.
  3. Rekker R. F., de Kort H. M. The hydrophobic fragmental constant: an extension to a 1000 data point set. Eur. J. Med. Chem. 1979. Vol. 14. P. 479–488.
  4. Leschev S. M. Regularities of extraction in systems on the basis of polar organic solvents and use of such systems for separation of impotant hydrophobic substances. Ion Exch. Solvent extr. 2001. Vol. 15. P. 295–330.
  5. Leschev S. M., Zaidel A. U., Zayats M. F. [Method of group increments as a way of generalization of the data on the extraction of organic substances and assessment of intramolecular effects influence on their extraction from aqueous solutions]. Khim. novykh materialov biologicheski aktivnykh veshchestv. Minsk, 2016. P. 135–151 (in Russ.).
  6. Zayats M. F., Leschev S. M. [Application of distribution Gibbs energy additivity principle for prediction of extraction of some pesticides]. Vestsi NAN Belarusi. Ser. khim. navuk. 2016. No. 2. P. 26–36 (in Russ.).
  7. Zayats M. F., Leschev S. M., Petrashkevich N. V., et al. Distribution of pesticides in n-hexane/water and n-hexane/acetonitrile systems and estimation of possibilities of their extraction isolation and preconcentration from various matrices. Anal. Chim. Acta. 2013. Vol. 774. P. 33–43. DOI: 10.1016/j.aca.2013.03.003.
  8. Zayats M. F., Leschev S. M., Zayats M. A. An improved extraction method of rapeseed oil sample preparation for the subsequent determination in it of azole class fungicides by gas chromatography. Anal. Chem. Res. 2015. Vol. 3. P. 37–45. DOI: 10.1016/j.ancr.2014.11.004.
  9. Leschev S. M., Bunevich N. V., Shulyakovskaya O. V. [Extraction of polychlorinated biphenyls and organochlorine pesticides by polar organic solvents]. Vestsi NAN Belarusi. Ser. khim. navuk. 2012. No. 1. P. 47–52 (in Russ.).
  10. Cheng T., Zhao Y., Li X., et al. Computation of octanol-water partition coefficients by guiding an additive model with knowledge. J. Chem. Inf. Model. 2007. Vol. 47, issue 6. P. 2140–2148. DOI: 10.1021/ci700257y.
  11. [Hygienic standards content of the active ingredients of pesticides (plant protection products) in the environment, food raw materials, food : the Minist. of Health of the Repub. of Belarus]. Decree dated 27 Sept., 2012. No. 149. Minsk, 2012 (in Russ.).
  12. Pleshko L. V., Khvalei O. A., Gololob T. I., et al. (compil.). [The State Register of plant protection products (pesticides) and fertilizers permitted for use on the territory of the Republic of Belarus]. Minsk, 2014 (in Russ.).
Published
2017-12-01
Keywords: extraction of organophosphorus pesticides, the principle of additivity of Gibbs energy of distribution, increment of the functional group
How to Cite
Zayats, M. F., Leschev, S. M., Furs, S. F., & Zhylko, V. V. (2017). Peculiarities of extraction of organophosphorus pesticides and its description from the perspective of the principle of additivity of Gibbs energy of distribution. Journal of the Belarusian State University. Chemistry, 2, 68-77. Retrieved from https://journals.bsu.by/index.php/chemistry/article/view/1169
Issue
No 2 (2017): Journal of the Belarusian State University. Chemistry
Section
Original Articles

The authors who are published in this journal agree to the following:

  1. The authors retain copyright on the work and provide the journal with the right of first publication of the work on condition of license Creative Commons Attribution-NonCommercial. 4.0 International (CC BY-NC 4.0).
  2. The authors retain the right to enter into certain contractual agreements relating to the non-exclusive distribution of the published version of the work (e.g. post it on the institutional repository, publication in the book), with the reference to its original publication in this journal.
  3. The authors have the right to post their work on the Internet (e.g. on the institutional store or personal website) prior to and during the review process, conducted by the journal, as this may lead to a productive discussion and a large number of references to this work. (See The Effect of Open Access.)