21. Corcellas C, Eljarrat E, Barceló D (2015) Enantiomeric-selective determination of pyrethroids:
application to human samples. Anal Bioanal Chem 407:779–786. https://doi.org/10.1007/
s00216-014-7905-6
22. Liu W, Gan JJ, Qin S et al (2005) Separation and aquatic toxicity of enantiomers of synthetic
pyrethroid insecticides. Chirality 52:6233–6238. https://doi.org/10.1002/chir.20122
23. Liu W, Gan JJ, Lee S, Werner I (2004) Isomer selectivity in aquatic toxicity and biodegradation of cypermethrin. J Agric Food Chem 52:6233–6238. https://doi.org/10.1021/jf0490910
24. Albaseer SS (2012) Development of a reversed-phase high performance liquid chromatographic method for efficient diastereomeric separation and quantification of cypermethrin,
resmethrin and permethrin. Res J Chem Sci 2:26–31
25. FAO/WHO (2015) FAO specifications and evaluations for agricultural pesticides. Permethrin
(40:60 cis:trans isomer ratio), 40 pp. http://www.fao.org/fileadmin/templates/agphome/docu
ments/Pests_Pesticides/Specs/Permethrin_2015_08.pdf
26. Nahler G (2010) Committee for Veterinary Medicinal Products (CVMP) permethrin summary
report. Dict Pharm Med 32. https://doi.org/10.1007/978-3-211-89836-9_245
27. Li ZY, Luo XN, Li QL et al (2015) Stereo and enantioselective separation and identification of
synthetic pyrethroids, and photolytical isomerization analysis. Bull Environ Contam Toxicol
94:254–259. https://doi.org/10.1007/s00128-014-1405-4
28. Ye X, Xiong K, Liu J (2016) Comparative toxicity and bioaccumulation of fenvalerate and
esfenvalerate to earthworm Eisenia fetida. J Hazard Mater 310:82–88. https://doi.org/10.1016/
j.jhazmat.2016.02.010
29. EFSA – European Food Safety Authority (2016) Conclusion on the peer review of the
pesticide risk assessment of the active substance gamma-cyhalothrin. EFSA J 11:3033.
https://doi.org/10.2903/j.efsa.2013.3033
30. Nahler G (2010) Committee for Veterinary Medicinal Products (CVMP) cyfluthrin summary
report. Dict Pharm Med 32. https://doi.org/10.1007/978-3-211-89836-9_245
31. Ross MK, Borazjani A, Edwards CC, Potter PM (2006) Hydrolytic metabolism of pyrethroids
by human and other mammalian carboxylesterases. Biochem Pharmacol 71:657–669. https://
doi.org/10.1016/j.bcp.2005.11.020
32. Sancho E, Banegas S, Villarroel MJ, Ferrando D (2018) Impaired reproduction and individual
growth of the water flea Daphnia magna as consequence of exposure to the non-ester
pyrethroid etofenprox. Environ Sci Pollut Res 25:6209–6217. https://doi.org/10.1007/
s11356-017-0952-8
33. Tang W, Wang D, Wang J et al (2018) Pyrethroid pesticide residues in the global environment:
an overview. Chemosphere 191:990–1007. https://doi.org/10.1016/j.chemosphere.2017.
10.115
34. Diao J, Xu P, Liu D et al (2011) Enantiomer-specific toxicity and bioaccumulation of alphacypermethrin to earthworm Eisenia fetida. J Hazard Mater 192:1072–1078. https://doi.org/10.
1016/j.jhazmat.2011.06.010
35. Velki M, Hackenberger BK (2013) Different sensitivities of biomarker responses in two
epigeic earthworm species after exposure to pyrethroid and organophosphate insecticides.
Arch Environ Contam Toxicol 65:498–509. https://doi.org/10.1007/s00244-013-9930-4
36. Zhao M, Wang C, Liu KK, Sun L, Li L, Liu W (2009) Enantioselectivity in chronic toxicology
and accumulation of the synthetic pyrethroid insecticide bifenthrin in Daphnia magna. Environ
Toxicol Chem 28:1475. https://doi.org/10.1897/08-527.1
37. Liu W, Gan JJ, Qin S (2005) Separation and aquatic toxicity of enantiomers of synthetic
pyrethroid insecticides. Chirality 17:127–133. https://doi.org/10.1002/chir.20122
38. Mu X, Shen G, Huang Y et al (2017) The enantioselective toxicity and oxidative stress of betacypermethrin on zebrafish. Environ Pollut 229:312–320. https://doi.org/10.1016/j.envpol.
2017.05.088
39. Wang L, Liu W, Yang C et al (2007) Enantioselectivity in estrogenic potential and uptake of
bifenthrin. Environ Sci Technol 41:6124–6128. https://doi.org/10.1021/es070220d
Stereoselectivity and Environmental Behaviour of Pyrethroids
171
application to human samples. Anal Bioanal Chem 407:779–786. https://doi.org/10.1007/
s00216-014-7905-6
22. Liu W, Gan JJ, Qin S et al (2005) Separation and aquatic toxicity of enantiomers of synthetic
pyrethroid insecticides. Chirality 52:6233–6238. https://doi.org/10.1002/chir.20122
23. Liu W, Gan JJ, Lee S, Werner I (2004) Isomer selectivity in aquatic toxicity and biodegradation of cypermethrin. J Agric Food Chem 52:6233–6238. https://doi.org/10.1021/jf0490910
24. Albaseer SS (2012) Development of a reversed-phase high performance liquid chromatographic method for efficient diastereomeric separation and quantification of cypermethrin,
resmethrin and permethrin. Res J Chem Sci 2:26–31
25. FAO/WHO (2015) FAO specifications and evaluations for agricultural pesticides. Permethrin
(40:60 cis:trans isomer ratio), 40 pp. http://www.fao.org/fileadmin/templates/agphome/docu
ments/Pests_Pesticides/Specs/Permethrin_2015_08.pdf
26. Nahler G (2010) Committee for Veterinary Medicinal Products (CVMP) permethrin summary
report. Dict Pharm Med 32. https://doi.org/10.1007/978-3-211-89836-9_245
27. Li ZY, Luo XN, Li QL et al (2015) Stereo and enantioselective separation and identification of
synthetic pyrethroids, and photolytical isomerization analysis. Bull Environ Contam Toxicol
94:254–259. https://doi.org/10.1007/s00128-014-1405-4
28. Ye X, Xiong K, Liu J (2016) Comparative toxicity and bioaccumulation of fenvalerate and
esfenvalerate to earthworm Eisenia fetida. J Hazard Mater 310:82–88. https://doi.org/10.1016/
j.jhazmat.2016.02.010
29. EFSA – European Food Safety Authority (2016) Conclusion on the peer review of the
pesticide risk assessment of the active substance gamma-cyhalothrin. EFSA J 11:3033.
https://doi.org/10.2903/j.efsa.2013.3033
30. Nahler G (2010) Committee for Veterinary Medicinal Products (CVMP) cyfluthrin summary
report. Dict Pharm Med 32. https://doi.org/10.1007/978-3-211-89836-9_245
31. Ross MK, Borazjani A, Edwards CC, Potter PM (2006) Hydrolytic metabolism of pyrethroids
by human and other mammalian carboxylesterases. Biochem Pharmacol 71:657–669. https://
doi.org/10.1016/j.bcp.2005.11.020
32. Sancho E, Banegas S, Villarroel MJ, Ferrando D (2018) Impaired reproduction and individual
growth of the water flea Daphnia magna as consequence of exposure to the non-ester
pyrethroid etofenprox. Environ Sci Pollut Res 25:6209–6217. https://doi.org/10.1007/
s11356-017-0952-8
33. Tang W, Wang D, Wang J et al (2018) Pyrethroid pesticide residues in the global environment:
an overview. Chemosphere 191:990–1007. https://doi.org/10.1016/j.chemosphere.2017.
10.115
34. Diao J, Xu P, Liu D et al (2011) Enantiomer-specific toxicity and bioaccumulation of alphacypermethrin to earthworm Eisenia fetida. J Hazard Mater 192:1072–1078. https://doi.org/10.
1016/j.jhazmat.2011.06.010
35. Velki M, Hackenberger BK (2013) Different sensitivities of biomarker responses in two
epigeic earthworm species after exposure to pyrethroid and organophosphate insecticides.
Arch Environ Contam Toxicol 65:498–509. https://doi.org/10.1007/s00244-013-9930-4
36. Zhao M, Wang C, Liu KK, Sun L, Li L, Liu W (2009) Enantioselectivity in chronic toxicology
and accumulation of the synthetic pyrethroid insecticide bifenthrin in Daphnia magna. Environ
Toxicol Chem 28:1475. https://doi.org/10.1897/08-527.1
37. Liu W, Gan JJ, Qin S (2005) Separation and aquatic toxicity of enantiomers of synthetic
pyrethroid insecticides. Chirality 17:127–133. https://doi.org/10.1002/chir.20122
38. Mu X, Shen G, Huang Y et al (2017) The enantioselective toxicity and oxidative stress of betacypermethrin on zebrafish. Environ Pollut 229:312–320. https://doi.org/10.1016/j.envpol.
2017.05.088
39. Wang L, Liu W, Yang C et al (2007) Enantioselectivity in estrogenic potential and uptake of
bifenthrin. Environ Sci Technol 41:6124–6128. https://doi.org/10.1021/es070220d
Stereoselectivity and Environmental Behaviour of Pyrethroids
171