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The photochemical behaviour of five household pyrethroid insecticides and a synergist as studied by photo-solid-phase microextraction

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Abstract

In the present study, solid-phase microextraction in photochemical studies was used to investigate UV light induced photodegradation of five pyrethroids (empenthrin, transfluthrin, allethrin, phenothrin and cyphenothrin) and a synergist (piperonyl butoxide), which are common ingredients of household insecticides. Gas chromatography coupled with mass spectrometry was used to separate and tentatively identify the parent compounds and their corresponding photoproducts generated in the same polydimethylsiloxane fibre. Kinetics curves were obtained and apparent first-order rate constants and half-lives were estimated. Twenty-six photoproducts were tentatively identified and photodegradation pathways for the compounds investigated were proposed. It is a matter of some concern that three of the photoproducts identified [(3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid, 3-phenoxybenzaldehyde and (3-phenoxyphenyl)methanol] have been reported to be endocrine disruptors. There is no record of previous studies of cyphenothrin and empenthrin photodegradation, and therefore the present study represents the first attempt to elucidate the photochemical behaviour of these compounds.

Photo-SPME for Pyrethroids

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References

  1. Amweg EL, Weston DP, You J, Lydy MJ (2006) Environ Sci Technol 40:1700–1706

    Article  CAS  Google Scholar 

  2. Woudneh MB (2006) J Agric Food Chem 54:6957–6962

    Article  CAS  Google Scholar 

  3. Schettgen T, Koch HM, Drexler H, Angerer J (2002) J Chromatogr B 778:121–130

    Article  CAS  Google Scholar 

  4. Beltran J, Peruga A, Pitarch E, López FJ, Hernández F (2003) Anal Bioanal Chem 376:502–511

    Article  CAS  Google Scholar 

  5. Agency for Toxic Substances and Disease Registry (2003) Toxicological profile for pyrethrins and pyrethroids. Agency for Toxic Substances and Disease Registry, Atlanta

  6. Fishel FM (2005) Pesticide toxicity profile: synthetic pyrethroid pesticides. http://www.edis.ifas.ufl.edu

  7. Pera-Titus M, García-Molina V, Baños MA, Giménez J, Esplugas S (2004) Appl Catal B 47:219–256

    Article  CAS  Google Scholar 

  8. Shemer H, Sharpless CM, Linden KG (2005) Water Air Soil Pollut 168:145–155

    Article  CAS  Google Scholar 

  9. Chen Y-L, Casida JE (1969) J Agric Food Chem 17:208–215

    Article  CAS  Google Scholar 

  10. Ruzo LO, Gaughan LC, Casida JE (1980) J Agric Food Chem 28:246–249

    Article  CAS  Google Scholar 

  11. Kawano Y, Yanagihara K, Miyamoto T, Yamamoto I (1980) J Chromatogr 198:317–328

    Article  CAS  Google Scholar 

  12. Kimmel EC, Casida JE, Ruzo LO (1982) J Agric Food Chem 30:623–626

    Article  CAS  Google Scholar 

  13. Isobe N, Matsuo M, Miyamoto J (1984) Tetrahedron Lett 25:861–864

    Article  CAS  Google Scholar 

  14. Ruzo LO, Smith IH, Casida JE (1982) J Agric Food Chem 30:110–115

    Article  CAS  Google Scholar 

  15. Fishbein L, Gaibel ZLF (1971) Bull Environ Contam Toxicol 5:546–552

    Article  Google Scholar 

  16. FAO (2001) Piperonyl butoxide (062) In: JMPR: Evaluations of Pesticide Residues, FAO Pesticide Management, FAO Pesticides for Plant Protection Products. http://www.fao.org/ag/AGP/AGPP/Pesticid/JMPR/Download/2001_eva/13%20Piperonyl%20butoxide.pdf

  17. Advisory Committee on Pesticides (1986) Evaluation on: transfluthrin use as a public hygiene insecticides., Food and Environment Protection Act 1985, part III. Control of pesticides regulations. Advisory Committee on Pesticides, York

  18. Llompart M, Lores M, Lourido M, Sánchez-Prado L, Cela R (2003) J Chromatogr A 985:175–183

    Article  CAS  Google Scholar 

  19. Sánchez-Prado L, Llompart M, Lores M, García-Jares C, Cela R (2004) J Chromatogr A 1047:271–279

    Article  Google Scholar 

  20. Fernández-Álvarez M, Sánchez-Prado L, Lores M, Llompart M, García-Jares C, Cela R (2007) J Chromatogr A (in press). DOI 10.1016/j.chroma.2006.12.095

  21. Lores M, Sánchez-Prado L, Llompart M, García-Jares C, Cela R (2004) Inter J Environ Anal Chem 85:281–291

    Google Scholar 

  22. Tyler CR, Beresford N, Van der Woning M, Sumpter JP, Thorpe K (2000) Environ Toxicol Chem 19:801–809

    Article  CAS  Google Scholar 

  23. McCarthy AR, Thomson BM, Shaw IC, Abell AD (2006) J Environ Monit 8:197–202

    Article  CAS  Google Scholar 

  24. Ruzo LO, Holmstead RL, Casida JE (1977) J Agric Food Chem 25:1385–1394

    Article  CAS  Google Scholar 

  25. Holmstead RL, Casida JE, Ruzo LO, Fullmer DG (1978) J Agric Food Chem 26:590–595

    Article  CAS  Google Scholar 

  26. Ruzo LO (1983) J Agric Food Chem 31:1113–1115

    Article  CAS  Google Scholar 

  27. Ruzo LO, Krishnamurthy VV, Casida JE, Gohre K (1987) J Agric Food Chem 35:879–883

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The present study was supported financially by FEDER funding, project CTQ2006-03334/BQU of the Spanish Ministry of Education and Science and PGIDIT06-PXIB237039PR of the Xunta de Galicia. M.F.-A. gratefully acknowledges the award of a doctoral grant (FPU) from the Spanish Ministry of Education and Science.

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Authors and Affiliations

  1. Departamento de Química Analítica, Nutrición y Bromatología, Facultad de Química, Instituto de Investigación y Análisis Alimentario, Universidad de Santiago de Compostela, Avda. das Ciencias s/n, 15782, Santiago de Compostela, Spain

    M. Fernández-Álvarez, M. Lores, M. Llompart, C. García-Jares & R. Cela

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  1. M. Fernández-Álvarez
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  2. M. Lores
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  3. M. Llompart
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  4. C. García-Jares
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  5. R. Cela
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Correspondence to M. Lores.

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Fernández-Álvarez, M., Lores, M., Llompart, M. et al. The photochemical behaviour of five household pyrethroid insecticides and a synergist as studied by photo-solid-phase microextraction. Anal Bioanal Chem 388, 1235–1247 (2007). https://doi.org/10.1007/s00216-007-1292-1

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  • DOI: https://doi.org/10.1007/s00216-007-1292-1

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