Abstract
Florpyrauxifen-benzyl is an active ingredient used as herbicide to control weeds in rice cultivation. So far, there are few studies related to the extraction and determining methodologies for this compound. Therefore, this work aimed to optimize and validate solid–liquid extraction with low temperature purification (SLE-LTP) using high-performance liquid chromatography coupled to a diode array detection (HPLC–DAD) to determine the florpyrauxifen-benzyl in rice samples. The results showed that the optimal chromatographic conditions were obtained using the Kinetex column, temperature of 25 °C, mobile phase composition of methanol:water (78:22 v/v), flow rate of 0.3 mL min−1, and 260 nm as the wavelength. The optimum extraction conditions were obtained using acetonitrile and water (2:1) as extraction phase, followed by clean-up of extracts with alumina. The recovery percentage achieved was close to 100%, with relative standard deviation (RSD) less than 9.0%. The result showed a significant matrix effect (184.3%), but the methodology was precise, accurate, linear, and selective, with a quantification limit of 5.0 μg kg−1.
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All data supporting the results of this study are available in the article and its Supplementary information files.
References
ANVISA Agência Nacional de Vigilância Sanitária (2022) Florpyrauxifen-benzyl. https://www.gov.br/anvisa/pt-br/setorregulado/regularizacao/agrotoxicos/monografias/monografias-autorizadas/f/4376json-file-1/view. Accessed 5 May 2023
APVMA Australian Pesticides and Veterinary Medicines Authority (2018) On the evaluation of the new active florpyrauxifen-benzyl (Rinskor™) in the product GF-3301 herbicide. https://apvma.gov.au/node/29096. Accessed 3 April 2023
Arena M, Auteri D, Barmaz S et al (2018) Peer review of the pesticide risk assessment of the active substance florpyrauxifen (variant assessed florpyrauxifen-benzyl). EFSA J 16:5378–5399. https://doi.org/10.2903/j.efsa.2018.5378
Bazilio FS, Bomfim MVJ, Almeida RJ, Abrantes SMP (2012) Uso de planilha eletrônica na verificação da adequação de curva analítica ao modelo linear. Revista Analytica 59:60–67
Economou A, Botitsi H, Antoniou S, Tsipi D (2009) Determination of multi-class pesticides in wines by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Chromatogr A 1216:5856–5867. https://doi.org/10.1016/j.chroma.2009.06.031
EMBRAPA Empresa Brasileira de Pesquisa Agropecuária (2021) Cultivo do arroz-Estatística de produção. https://www.embrapa.br/agencia-de-informacao-tecnologica/cultivos/arroz/pre-producao/socioeconomia/estatistica-de-producao#:~:text=Em%20primeiro%20lugar%20est%C3%A1%20a,(19%20milh%C3%B5es%20de%20toneladas). Accessed 30 May 2023
Li W, Zhang Y, Jia H, Zhou W, Li B, Huang H (2019) Residue analysis of tetraniliprole in rice and related environmental samples by HPLC/MS. Microchem J 150:104168. https://doi.org/10.1016/j.microc.2019.104168
Lopes JCS, Sicupira LC, Silvério FO (2023) Extraction method for determining florpyrauxifen-benzyl herbicide in soil. J Braz Chem Soc 34:302–308. https://doi.org/10.21577/0103-5053.20220108
Mardani Z, Shakoori A, Peiravian F, Nouri L, Salamzadeh J (2021) Development of a liquid chromatography-mass spectrometry technique for evaluation of multi-class pesticides in rice samples. Iran J Pharm Res 20:165–174. https://doi.org/10.22037/ijpr.2020.113071.14095
MDAR Massachusetts Department of Agriculture and MassDEP Massachusetts Department of Environmental Protection (2019) Review of florpyrauxifen-benzyl for application to Massachusetts lakes and ponds. https://www.mass.gov/doc/florpyrauxifen-benzyl/download?_ga=2.139085427.1949808461.1686704084-1027380426.1686704084. Accessed 30 April 2023
Mesquita TCR, Santos RR, Cacique AP, De Sá LJ, Silvério FO, Pinho GP (2018) Easy and fast extraction methods to determine organochlorine pesticides in sewage sludge, soil, and water samples based at low temperature. J Environ Sci Health B 53:199–206. https://doi.org/10.1080/03601234.2017.1405626
Mondal R, Kole RK, Bhattacharyya A (2017) Validation of multiresidue method for analysis of 31 pesticides in rice using gas chromatography-tandem mass spectrometry. J AOAC Int 100:1094–1101. https://doi.org/10.5740/jaoacint.16-0377
Pereira NGF, Silvério FO, Pinho GP (2020) Optimisation, validation and application of the solid-liquid extraction with low-temperature purification followed by gas chromatography-mass spectrometry for determination of phthalates in sewage sludge. Int J Environ an Ch 100:968–980. https://doi.org/10.1080/03067319.2019.1646735
Pinho GP, Neves AA, Queiroz MELR, Silvério FO (2009) Efeito de matriz na quantificação de agrotóxicos por cromatografia gasosa. Quim Nova 32:987–995. https://doi.org/10.1590/S0100-40422009000400030
Ramalho MB, Durães AFS, Silvério FO, Pinho GP (2020) Determination of three cresol isomers in sewage sludge by solid-liquid extraction with low temperature purification and gas chromatography-mass spectrometry. J Environ Sci Health B 55:184–192. https://doi.org/10.1080/03601234.2019.1678952
Rebelo AM, Dolzan MD, Heller M, Deschamps FC, Abate G, Micke GA, Grassi MT (2016) Simultaneous determination of herbicides in rice by QuEChERS and LC-MS/MS using matrix-matched calibration. J Braz Chem Soc 27:186–193. https://doi.org/10.5935/0103-5053.20150269
SANTE/11312/2021 European Commission (2021) Guidance document on analytical quality control and method validation procedures for pesticide residues analysis in food and feed. https://www.accredia.it/documento/guidance-sante-11312-2021-analytical-quality-control-and-method-validation-procedures-for-pesticide-residues-analysis-in-food-and-feed/. Accessed 3 April 2023
Sefiloglu FO, Tezel U, Balcioglu IA (2021) Validation of an analytical workflow for the analysis of pesticide and emerging organic contaminant residues in paddy soil and rice. J Agric Food Chem 69:3298–3306. https://doi.org/10.1021/acs.jafc.0c06111
Sicupira LC, Tiago JPF, Pinho GP, Silvério FO (2019) Simultaneous determination of 2,3,7,8-TCDD and 2,3,7,8-TCDF in water samples by LLE-LTP and HPLC-DAD. J Braz Chem Soc 30:284–1292. https://doi.org/10.21577/0103-5053.20190024
Sicupira LC, Freitas LVP, Pinho GP, Silvério FO (2023) Simultaneous determination of a polychlorinated dibenzo-p-dioxin and dibenzo-p-furan in environmental water by dispersive liquid-liquid microextraction (DLLME) and a modified QuEChERS procedure with high-performance liquid chromatography – diode array detection (HPLC-DAD). Anal Lett 56:2309–2328. https://doi.org/10.1080/00032719.2023.2166521
Souza SVC, Junqueira RG (2005) A procedure to assess linearity by ordinary least squares method. Anal Chim Acta 552:25–35. https://doi.org/10.1016/j.aca.2005.07.043
Tomasini D, Sampaio MRF, Caldas SS, Buffon JG, Duarte FA, Primel EG (2012) Simultaneous determination of pesticides and 5-hydroxymethylfurfural in honey by the modified QuEChERS method and liquid chromatography coupled to tandem mass spectrometry. Talanta 99:380–386. https://doi.org/10.1016/j.talanta.2012.05.068
US Food and Drug Administration (2017a) Final registration decision on the new active ingredient florpyrauxifen-benzyl. https://www.regulations.gov/document/EPA-HQ-OPP-2016-0560-0065. Accessed 3 April 2023
US Food and Drug Administration (2017b) Florpyrauxifen-benzyl; pesticide tolerances. https://www.federalregister.gov/documents/2017/10/06/2017-21614/florpyrauxifen-benzyl-pesticide-tolerances. Accessed 5 June 2023
Vieira LHS, Sicupira LC, Cacique AP, Silvério FO (2022) Optimization and validation of LLE-LTP to determine florpyrauxifen-benzyl herbicide in water samples by HPLC-DAD. J Environ Sci Health B Pestic Food Contam Agric Wastes 57:697–709. https://doi.org/10.1080/03601234.2022.2099202
Zhou R, Dong Z, Bian C, Wu T, Zhou W, Li Y, Li B (2022) Florpyrauxifen-benzyl in paddy field environment: its residue analysis, dissipation dynamics, storage stability, dietary risk assessment and decontamination. https://doi.org/10.2139/ssrn.4008164. Accessed 3 April 2023
Acknowledgements
The authors also thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Laboratório de Química Instrumental (LQI-UFMG), and the Universidade Federal de Minas Gerais (UFMG) for the infrastructure provided.
Funding
This study was financed in part by the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (306551/2022–5) and the Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) (APQ-02736–21 and APQ-00472–22). The authors are grateful to the Instituto Federal do Norte de Minas Gerais (IFNMG) for financial support in the form of research grants.
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J. C. S. Lopes: sample preparation, HPLC–DAD analysis, investigation, validation, and writing original draft and editing. L. C. Sicupira: provided technical support for the research, prepared figures, review and editing, and final draft supervision. G. P. de Pinho: provided critical insights and suggestions to improve the study, supervision, and helped revise the manuscript. F. O. Silvério: review and editing, supervision, project administration, funding acquisition, and coordinated the study. All authors have read and agreed to the published version of the manuscript.
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Lopes, J.C., Sicupira, L.C., Pinho, G.P. et al. Extraction Method for Determining Florpyrauxifen-Benzyl Herbicide in Rice. Food Anal. Methods 17, 322–331 (2024). https://doi.org/10.1007/s12161-023-02569-3
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DOI: https://doi.org/10.1007/s12161-023-02569-3