Abstract
Azocyclotin and cyhexatin are pesticides commonly used in mite control. However, these organotin compounds (OTC) are highly harmful to the aquatic ecosystem and supposedly mobile in the soil. In addition to not existing defined rules of use, few studies have been carried out on organotins’ behavior and environmental control. Liquid chromatography has been pointed out for the OTC quantitation because of gas chromatography’s thermal stability and derivatization limitations. Hence, a new high-performance liquid chromatography method with photodiode array detection was developed for quality assurance and quality control and environmental performance assessment purposes. Hysteresis index (HI) and mobilization factor were determined from sorption/desorption in sandy and clayey soils to assess mobility and environmental risk. Mobilization was observed for the two compounds by applying the dual-mode Freundlich–Langmuir model to the isotherms. Azocyclotin showed greater mobility, 23% and 19%, and HI of − 0.15 and 7.8 \(\times \) 10\(^{-4}\) for clayey and sandy soil samples, respectively. Although cyhexatin was practically immobile for both soil samples, it can be mobilized as an azocyclotin metabolite, increasing the environmental impact and risk for agricultural uses.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Code availability
Not applicable
Notes
The main numerical results in this section can be generated from the MatLab script available at https://data.mendeley.com/datasets/2xz2w7w2jd/1. Ferreira Lima, Andre; Onishi, Bruno S. D.; Watanabe, Lycio S.; Santos, Maria Josefa; Abrao, Taufik (2021), “Mobility of organotin pesticides: azocyclotin and cyhexatin in clayey and sandy soils from the Northern Parana state - Brazil”, Mendeley Data, V1, https://doi.org/10.17632/2xz2w7w2jd.1
References
Blahovec J, Yanniotis S (2009) Modified classification of sorption isotherms. J Food Eng 91(1):72–77. https://doi.org/10.1016/j.jfoodeng.2008.08.007
Blunden SJ, Evans CJ (1990) The handbook of environmental chemistry, vol 3. Springer, Berlin
Cheng P, Schachman H (1955) Studies on the validity of the einstein viscosity law and stokes law of sedimentation. J Polym Sci 16(1):19–30. https://doi.org/10.1002/pol.1955.120168102
Constantino L, Quirino J, Abrao T et al (2018) Sorption-desorption of antimony species onto calcined hydrotalcite: surface structure and control of competitive anions. J Haz Mat 344:649–656. https://doi.org/10.1016/j.jhazmat.2017.11.016
Dhananjay K, Pandey L, Gaur J (2016) Metal sorption by algal biomass: from batch to continuous system. Algal Res 18:95–109. https://doi.org/10.1016/j.algal.2016.05.026
Do D (1998) Adsorption analysis—equilibria and kinetics, vol 2. Imperial College Press, London
Ebdon L, Pitts L, Cornelis R et al (2001) Trace element speciation for environment. The Royal Society of Chemistry, Food and Health, London. https://doi.org/10.1039/9781847552204
Embrapa (2011) Manual of soil analysis. Brazilian Agricultural Research Company, Jardim Botanico, 1024 Rio de Janeiro, RJ, 2nd edn
Essington M (2015) Soil and water chemistry, 2nd edn. CRC Press, New York
EU (2012) https://ec.europa.eu/. Europen Union Accessed January 2019
Fent K (1996) Ecotoxicology of organotin compounds. Crit Rev Toxicol 26:3–117. https://doi.org/10.3109/10408449609089891
Fent K, Mueller M (1991) Occurrence of organotins in municipal wastewater and sewage sludge and behavior in a treatment plant. Environ Sci Technol 25:489–493. https://doi.org/10.1021/es00015a017
Galunin E, Alba MD, Santos MJ et al (2010) Lanthanide sorption on smectitic clays in presence of cement leachates. Geochim Cosmochim Acta 74(3):862–875. https://doi.org/10.1016/j.gca.2009.11.003
Galunin E, Ferreti J, Zapelline I et al (2014) Cadmium mobility in sediments and soils from a coal mining area on Tibagi River watershed: Environmental risk assessment. J Haz Mat 265:280–287. https://doi.org/10.1016/j.jhazmat.2013.11.010
Giacalone A, Gianguzza A, Petignano A et al (2006) Sequestration of organometallic compounds by natural organic matter. Binding of trimethyltin(IV) by fulvic and alginic acids. Appl Organometallic Chem 20(10):706–717. https://doi.org/10.1002/aoc.1128
Gobbo F, Sarita P, Karina P (2015) High precision and selectivity for quantitation of enrofloxacin and ciprofloxacin in five chicken tissues using solid phase extraction and esi lcms for application in monitoring residues. Anal Methods 7:3291–3297. https://doi.org/10.1039/c4ay02962c
Godoi A, Favoreto R, Santiago S (2003) Environmental contamination for organotin compounds. Quim Nova 26:708–716. https://doi.org/10.1590/S0100-40422003000500015
Gui W, Tian C, Sun Q et al (2016) Simultaneous determination of organotin pesticides by hplc-icp-ms and their sorption, desorption, and transformation in freshwater sediments. Water Res 95:185–194. https://doi.org/10.1016/j.watres.2016.02.056
Guidelines HT (2005) ICH validation of analytical procedures: Text and Methodology. ICH Harmonized Tripartite Guidelines
Huang J, Matzner E (2004) Adsorption and desorption of organotin compounds in organic and mineral soils. Eur J Soil Sci 55(4):693–698. https://doi.org/10.1111/j.1365-2389.2004.00634.x
Joan A, Rozing J, Hattum V et al (1992) Normal-phase high-performance liquid chromatography with uv irradiation, morin complexation and fluorescence detection for the determination of organotin pesticides. J Chromatogr A 609:195–203. https://doi.org/10.1016/0021-9673(92)80163-O
Jones AD, Bruland GL, Agrawal SG et al (2005) Factors influencing the sorption of oxytetracycline to soils. Environ Toxicol Chem 24(4):761–770. https://doi.org/10.1897/04-037R.1
Kanimozhi V, Palanivel K, Akbarsha M (2016) Tributyltin-mediated hepatic, renal and testicular tissue damage in male syrian hamster (mesocricetus auratus): a study on impact of oxidative stress. SpringerPlus 5:1523. https://doi.org/10.1186/s40064-016-3186-1
Langmuir L (1916) The constitution and fundamental properties of solids and liquids. J Am Chem Soc 11:221–2295. https://doi.org/10.1021/ja02268a002
Ming H, Margaret A, Rav N et al (2012) Persistent toxic substances: sources, fates and effects. Rev Environ Health 27:207–213. https://doi.org/10.1515/reveh-2012-0040
Muller M, Markus D (1987) Degradation and residues of cyclohexyltin compounds in orchard soil following field application of cyhexatin. Bul Environ Contam Toxicol 38:627–633. https://doi.org/10.1007/bf01608595
Ning M, Gui W, Zhu G (2015) The analysis of azocyclotin and cyhexatin residues in fruits using ultrahigh-performance liquid chromatography-tandem mass spectrometry. Anal Methods 7:2108–2113. https://doi.org/10.1039/C4AY02624A
Oliveira R, Santelli R (2010) Occurrence and chemical speciation analysis of organotin compounds in the environment: A review. Talanta 82:9–24. https://doi.org/10.1016/j.talanta.2010.04.046
Perez R, Barasoain F (1983) High-performance liquid chromatographic determination of cyhexatin in technical and wettable pesticide powders. J Chromatogr A 260:200–205. https://doi.org/10.1016/0021-9673(83)80027-2
PubChem (2017a) https://pubchem.ncbi.nlm.nih.gov/compound/Cyhexatin, Accessed Nov 2021
PubChem (2017b) https://pubchem.ncbi.nlm.nih.gov/compound/Azocyclotin, Accessed Nov 2021
RS.Agricultural (2017) https://www.ars.usda.gov, Accessed Jan 2019
Silva R, Guerra D (2013) Use of natural and modified kaolinite/ilite as adsorbent for removal methylene blue dye from aqueous solution. J Chil Chem Soc 58(1):1517–1519. https://doi.org/10.4067/S0717-97072013000100003
Sithole BB, Guy RD (1987) Models for tetracycline in aquatic environments ii interaction with humic substances. Water Air Soil Pollut 32:315–321. https://doi.org/10.1007/bf00225117
Sparks D (1995) Environmental soil chemistry. Academic Press, Book Marketing Department, San Diego
Swann RL, Laskowski DA, McCall PJ, et al (1983) A rapid method for the estimation of the environmental parameters octanol/water partition coefficient, soil sorption constant, water to air ratio, and water solubility. Residue Rev pp 7–28. https://doi.org/10.1007/978-1-4612-5462-1_3
Tomasz T, Jan S (2009) Application of hplc-dad and tlc-dad after spe to the quantitative analysis of pesticides in water samples. J Liq Chromatogr Relat Technol 32:1241–1258. https://doi.org/10.1080/10826070902854391
Walkley A, Black I (1934) An examination of the degtjareff method for determining soil organic matter and a proposed modification of the chromic acid titration method. Soil Sci 37:29–38. https://doi.org/10.1097/00010694-193401000-00003
Xiupin W, Lan D, Huarong Z et al (2006) Development of an analytical method for organotin compounds in fortified flour samples using microwave-assisted extraction and normal-phase hplc with uv detection. J Chromatogr B 843:268–274. https://doi.org/10.1016/j.jchromb.2006.06.013
Acknowledgements
The authors would like to thank Capes (Coordination for the Improvement of Higher Education Personnel) and State University of Londrina for their financial support and fellowships and the Spectroscopy Laboratory (LABESPEC), the Laboratory of X-ray Analysis (LARX) and the Analytical Instrumentation and Analytical Automation Development Laboratory (DIA) of UEL by FT-IR, XRD measurements and chromatography analysis
Funding
The authors would like to thank Capes—Coordination for the Improvement of Higher Education Personnel for their financial support on fellowships.
Author information
Authors and Affiliations
Contributions
All the authors whose names appear on the submission: (1) made substantial contributions to the conception or design of the work; the acquisition, analysis, and interpretation of data, (2) drafted the work or revised it critically for important intellectual content, (3) approved the version to be published, and (4) agree to be accountable for all aspects of the work in ensuring that questions related to the accuracy or integrity of any part of the work are appropriately investigated and resolved.
Corresponding author
Ethics declarations
Conflict of interest
The authors have declared no conflict of interest.
Ethics approval
Not applicable.
Consent to participate
Not applicable.
Consent for publication
Not applicable.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Lima, A.A.A., Onishi, B.S.D., Watanabe, L.S. et al. Mobility of organotin pesticides: azocyclotin and cyhexatin in clayey and sandy soils from the Northern Paraná state—Brazil. Environ Earth Sci 81, 236 (2022). https://doi.org/10.1007/s12665-022-10351-7
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s12665-022-10351-7