Advertisement

Identification and Characterization of Herbicide Penoxsulam Transformation Products in Aqueous Media by UPLC-QTOF-MS

  • Guofeng Chen
  • Yuxin Qiao
  • Xiaobo Zhang
  • Feng Liu
  • Hui Liao
  • Ruiying Zhang
  • Jiannan Dong
  • Bo TaoEmail author
Article

Abstract

Photodegradation is an important non-biodegradation process of pesticide degradation in aquatic environments. In this study, the effect of different forms of nitrogen on the photodegradation kinetics of penoxsulam was investigated. The photodegradation of penoxsulam was accelerated by NO3− and NO2− but was not affected by NH4+. Ultra-high-performance liquid chromatography coupled with time-of-flight mass spectrometry was used to separate and identify the transformation products (TPs)converted by photodegradation of penoxsulam in an aqueous solution under UV–Vis (290–800 nm) irradiation. Seven major transformation products were identified based on mass spectral data. The structure was determined by elemental composition calculations, comparison of structural analogs, and existing literature. The main pathways of photodegradation were found to be sulfonamide bond cleavage, rearrangement, triazole ring cleavage, and hydroxylation. These findings are critical to elucidate the environmental fate of penoxsulam in aquatic ecosystems and provide a basis for further environmental risk assessment.

Keywords

Penoxsulam Photodegradation Transformation products UPLC-QTOF-MS 

Notes

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 2016ZX08004001).

References

  1. Chen XX, Dong BZ, Lin HF, Hu JY (2016) Identification of photoproducts of fungicide cyprodinil and elucidation of transformation mechanism in water using LC-IT-TOF-MS/MS technique. Chemosphere 160:359–365.  https://doi.org/10.1016/j.chemosphere.2016.05.036 CrossRefGoogle Scholar
  2. Fotiou T, Triantis T, Kaloudis T, Hiskia A (2015) Photocatalytic degradation of cylindrospermopsin under UV-A, solar and visible light using TiO2 Mineralization and intermediate products. Chemosphere 119:S89–S94.  https://doi.org/10.1016/j.chemosphere.2014.04.045 CrossRefGoogle Scholar
  3. Gao J, Hedman C, Liu C, Guo T, Pedersen JA (2012) Transformation of sulfamethazine by manganese oxide in aqueous solution. Environ Sci Technol 46:2642–2651.  https://doi.org/10.1021/es202492h CrossRefGoogle Scholar
  4. Jabusch TW, Tjeerdema RS (2006) Microbial degradation of penoxsulam in flooded rice field soils. J Agric Food Chem 54:962–5967.  https://doi.org/10.1021/jf0606454 Google Scholar
  5. Lagunas-Allué L, Martínez-Soria MT, Sanz-Asensio J, Salvador A, Ferronato C, Chovelon JM (2012) Degradation intermediates and reaction pathway of pyraclostrobin with TiO2 photocatalysis. Appl Catal B 115–116:285–293.  https://doi.org/10.1016/j.apcatb.2011.12.015 CrossRefGoogle Scholar
  6. Lavtižar V, Gestel CAM, Dolenc D, Trebše P (2014) Chemical and photochemical degradation of chlorantraniliprole and characterization of its transformation products. Chemosphere 95:408–414.  https://doi.org/10.1016/j.chemosphere.2013.09.057 CrossRefGoogle Scholar
  7. Liu PY, Li B, Liu HD, Tian L (2014) Photochemical behavior of fenpropathrin and λ-cyhalothrin in solution. Environ Sci Pollut Res 21:1993–2001.  https://doi.org/10.1007/s11356-013-2119-6 CrossRefGoogle Scholar
  8. Monika Srivastava A, Suyal A, Srivastava PC (2017) Persistence behavior of penoxsulam herbicide in two different soils. Bull Environ Contam Toxicol 99:1–5.  https://doi.org/10.1007/s00128-017-2171-x CrossRefGoogle Scholar
  9. Nélieu S, Perreau F, Bonnemoy F, Ollitrault M, Azam D, Lagadic L, Bohatier J, Einhorn J (2009) Sunlight nitrate-induced photodegradation of chlorotoluron: evidence of the process in aquatic mesocosms. Environ Sci Technol 43:3148–3154.  https://doi.org/10.1021/es8033439 CrossRefGoogle Scholar
  10. Patetsini E, Dimitriadis VK, Kaloyianni M (2013) Biomarkers in marine mussels, Mytilus galloprovincialis, exposed to environmentally relevant levels of the pesticides, chlorpyrifos and penoxsulam. Aquat Toxicol 126:338–345.  https://doi.org/10.1016/j.aquatox.2012.09.009 CrossRefGoogle Scholar
  11. Pramanik SK, Das S, Bhattacharyya A (2008) Photodegradation of the herbicide penoxsulam in aqueous methanol and acetonitrile. J Environ Sci Health B 43:569–575.  https://doi.org/10.1080/03601230802234427 CrossRefGoogle Scholar
  12. Reimche GB, Machado SLO, Oliveira MA, Zanella R, Dressler VL, Flores EMM, Gonҫalves FF, Donato FF, Nunes MAG (2015) Imazethapyr and imazapic, bispyribac-sodium and penoxsulam: zooplankton and dissipation in subtropical rice paddy water. Sci Total Environ 514:68–76.  https://doi.org/10.1016/j.scitotenv.2015.01.055 CrossRefGoogle Scholar
  13. Rosenbom AE, Kjaer J, Olsen P (2010) Long-term leaching of rimsulfuron degradation products through sandy agricultural soils. Chemosphere 79:830–838.  https://doi.org/10.1016/j.chemosphere.2010.02.058 CrossRefGoogle Scholar
  14. Sandín-España P, Sevilla-Morán B, Lόpez-Goti C, Mateo-Miranda MM, Alonso-Prados JL (2015) Identification of sethoxydim degradation products in natural waters under different light sources by HPLC-QTOF-MS. Microchem J 119:6–10.  https://doi.org/10.1016/j.microc.2014.10.007 CrossRefGoogle Scholar
  15. Sondhia S, Rajput S, Varma RK, Kumar A (2016) Biodegradation of the herbicide penoxsulam (triazolopyrimidine sulphonamide) by fungal strains of Aspergillus in soil. Appl Soil Ecol 105:196–206.  https://doi.org/10.1016/j.apsoil.2016.03.010 CrossRefGoogle Scholar
  16. Storck V, Lucini V, Mamy L, Ferrari F, Papadopoulou ES, Nikolaki S, Karas PA, Servien R, Karpouzas DG, Trevisan M, Benoit P, Martin-Laurent F (2016) Identification and characterization of tebuconazole transformation products in soil by combining suspect screening and molecular typology. Environ Pollut 208:537–545.  https://doi.org/10.1016/j.envpol.2015.10.027 CrossRefGoogle Scholar
  17. Tokumura T, Yoshida N, Mori-Yasumoto K, Shirota O, Kurita T (2017) Degradation rates and products of fluticasone propionate in alkaline solutions. J Pharm Anal 7:297–302.  https://doi.org/10.1016/j.jpha.2017.03.010 CrossRefGoogle Scholar
  18. Tsochatzis ED, Tzimou-Tsitouridou R, Menkissoglu-Spiroudi U, Karpouzas DG, Katsantonis D (2013) Laboratory and field dissipation of penoxsulam, tricyclazole and profoxydim in rice paddy systems. Chemosphere 91:1049–1057.  https://doi.org/10.1016/j.chemosphere.2013.01.067 CrossRefGoogle Scholar
  19. Wang G, Liu GG, Liu HJ, Zhang N, Wang YL (2012) Photodegradation of salicylic acid in aquatic environment: effect of different forms of nitrogen. Sci Total Environ 435–436:573–577.  https://doi.org/10.1016/j.scitotenv.2012.05.068 Google Scholar
  20. Webster EP, Carlson TP, Salassi ME, Hensley JB, Blouin DC (2012) Imazethapyr plus residual herbicide programs for imidazolinone-resistant rice. Weed Technol 26:410–416.  https://doi.org/10.1614/WT-D-11-00179.1 CrossRefGoogle Scholar
  21. Xu J, Hao ZN, Guo S, Zhang Y, He Y, Meng W (2014) Photodegradation of sulfapyridine under simulated sunlight irradiation: kinetics, mechanism and toxicity evolvement. Chemosphere 99:186–191.  https://doi.org/10.1016/j.chemosphere.2013.10.069 CrossRefGoogle Scholar
  22. Yassine M, Fuster L, Dévier MH, Geneste E, Pardon P, Grélard A, Dufourc E, Iskandarani MA, Aït-Aïssa S, Garric J, Budzinski H, Mazellier P, Trivella AS (2018) Photodegradation of novel oral anticoagulants under sunlight irradiation in aqueous matrices. Chemosphere 193:329–336.  https://doi.org/10.1016/j.chemosphere.2017.11.036 CrossRefGoogle Scholar
  23. Yasuor H, Osuna MD, Ortiz A, Saldain NE, Eckert JW, Fischer AJ (2009) Mechanism of resistance to penoxsulam in late watergrass [Echinochloa phyllopogon (Stapf) Koss.]. J Agric Food Chem 57:3653–3660.  https://doi.org/10.1021/jf8039999 CrossRefGoogle Scholar
  24. Zhan MJ, Yang X, Kong LR (2004) A critical review of photochemistry of nitrite and nitrate ions in natural waters. Tech Equip Environ Pollut Control 5:14–19.  https://doi.org/10.3969/j.issn.1673-9108.2004.10.003 Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Guofeng Chen
    • 1
    • 2
  • Yuxin Qiao
    • 1
  • Xiaobo Zhang
    • 2
  • Feng Liu
    • 2
  • Hui Liao
    • 2
  • Ruiying Zhang
    • 2
  • Jiannan Dong
    • 2
  • Bo Tao
    • 1
    Email author
  1. 1.College of AgricultureNortheast Agricultural UniversityHarbinChina
  2. 2.Safety and Quality Institute of Agricultural ProductsHeilongjiang Academy of Agricultural SciencesHarbinChina

Personalised recommendations