References
1. de Albuquerque NCP, Carrão DB, Habenschus MD, de Oliveira ARM (2018) Metabolism
studies of chiral pesticides: a critical review. J Pharm Biomed Anal 147:89–109. https://doi.
org/10.1016/j.jpba.2017.08.011
2. Jeschke P (2018) Current status of chirality in agrochemicals. Pest Manag Sci 74:2389–2404.
https://doi.org/10.1002/ps.5052
3. Ulrich EM, Morrison CN, Goldsmith MR, Foreman WT (2012) Chiral pesticides: identification, description, and environmental implications. Rev Environ Contam Toxicol 217:1–74.
https://doi.org/10.1007/978-1-4614-2329-4_1
4. Sekhon BS (2009) Chiral pesticides. J Pestic Sci 34:1–12. https://doi.org/10.1584/jpestics.
r08-03
5. Wu Y, Miao H, Fan S (2012) Separation of chiral pyrethroid pesticides and application in
pharmacokinetics research and human exposure assessment. In: Pesticides in the modern
world – effects of pesticides exposure. IntechOpen, London, pp 140–166
6. Garrison AW (2011) An introduction to pesticide chirality and the consequences of
stereoselectivity. ACS Symp Ser 1085:1–7. https://doi.org/10.1021/bk-2011-1085.ch001
7. Corcellas C, Eljarrat E, Barceló D (2015) First report of pyrethroid bioaccumulation in wild
river fish: a case study in Iberian river basins (Spain). Environ Int 75:110–116. https://doi.org/
10.1016/j.envint.2014.11.007
8. ATSDR – Agency for Toxic Substances and Disease Registry (2003) Toxicological profile for
pyrethrins and pyrethroids. ATSDR, Atlanta
9. Wang W, Cai DJ, Shan ZJ et al (2007) Comparison of the acute toxicity for gammacyhalothrin and lambda-cyhalothrin to zebra fish and shrimp. Regul Toxicol Pharmacol
47:184–188. https://doi.org/10.1016/j.yrtph.2006.09.002
10. Gan J, Nillos MG, Lavado R et al (2010) Stereoselective biotransformation of permethrin to
estrogenic metabolites in fish. Chem Res Toxicol 23:1568–1575. https://doi.org/10.1021/
tx100167x
11. Jin Y, Wang W, Xu C et al (2008) Induction of hepatic estrogen-responsive gene transcription
by permethrin enantiomers in male adult zebrafish. Aquat Toxicol 88:146–152. https://doi.org/
10.1016/j.aquatox.2008.04.004
12. Gan J, Wang C, Zhang Q et al (2010) Integrative assessment of enantioselectivity in endocrine
disruption and immunotoxicity of synthetic pyrethroids. Environ Pollut 158:1968–1973.
https://doi.org/10.1016/j.envpol.2009.10.027
13. Katsuda Y (2012) Progress and future of pyrethroids. Top Curr Chem 314:1–30
14. Martel J (1992) The development and manufacture of pyrethroid insecticides. In: Chirality in
industry – the commercial manufacture and applications of optically active compounds. Wiley,
Chichester, p 87
15. Soderlund DM (2010) Toxicology and mode of action of pyrethroid insecticides, 3rd edn.
Elsevier, London
16. Rehman H, Aziz AT, Saggu S et al (2014) Systematic review on pyrethroid toxicity with
special reference to deltamethrin. J Entomol Zool Stud 2:60–70. https://doi.org/10.1016/j.
carres.2006.12.019
17. Chang J, Wang Y, Wang H et al (2016) Bioaccumulation and enantioselectivity of type I and
type II pyrethroid pesticides in earthworm. Chemosphere 144:1351–1357. https://doi.org/10.
1016/j.chemosphere.2015.10.011
18. Cahn RS, Ingold CK, Prelog V (1956) The specification of asymmetric configuration in
organic chemistry. Experientia 12:81–94. https://doi.org/10.1007/BF02157171
19. Prelog V, Helmchen G (1982) Basic principles of the CIP-system and proposals for a revision.
Angew Chemie Int Ed Engl 21:567–583. https://doi.org/10.1002/anie.198205671
20. Smith SW (2009) Chiral toxicology: it’s the same thing only different. Toxicol Sci 110:4–30.
https://doi.org/10.1093/toxsci/kfp097
170
C. E. T. Parente et al.
1. de Albuquerque NCP, Carrão DB, Habenschus MD, de Oliveira ARM (2018) Metabolism
studies of chiral pesticides: a critical review. J Pharm Biomed Anal 147:89–109. https://doi.
org/10.1016/j.jpba.2017.08.011
2. Jeschke P (2018) Current status of chirality in agrochemicals. Pest Manag Sci 74:2389–2404.
https://doi.org/10.1002/ps.5052
3. Ulrich EM, Morrison CN, Goldsmith MR, Foreman WT (2012) Chiral pesticides: identification, description, and environmental implications. Rev Environ Contam Toxicol 217:1–74.
https://doi.org/10.1007/978-1-4614-2329-4_1
4. Sekhon BS (2009) Chiral pesticides. J Pestic Sci 34:1–12. https://doi.org/10.1584/jpestics.
r08-03
5. Wu Y, Miao H, Fan S (2012) Separation of chiral pyrethroid pesticides and application in
pharmacokinetics research and human exposure assessment. In: Pesticides in the modern
world – effects of pesticides exposure. IntechOpen, London, pp 140–166
6. Garrison AW (2011) An introduction to pesticide chirality and the consequences of
stereoselectivity. ACS Symp Ser 1085:1–7. https://doi.org/10.1021/bk-2011-1085.ch001
7. Corcellas C, Eljarrat E, Barceló D (2015) First report of pyrethroid bioaccumulation in wild
river fish: a case study in Iberian river basins (Spain). Environ Int 75:110–116. https://doi.org/
10.1016/j.envint.2014.11.007
8. ATSDR – Agency for Toxic Substances and Disease Registry (2003) Toxicological profile for
pyrethrins and pyrethroids. ATSDR, Atlanta
9. Wang W, Cai DJ, Shan ZJ et al (2007) Comparison of the acute toxicity for gammacyhalothrin and lambda-cyhalothrin to zebra fish and shrimp. Regul Toxicol Pharmacol
47:184–188. https://doi.org/10.1016/j.yrtph.2006.09.002
10. Gan J, Nillos MG, Lavado R et al (2010) Stereoselective biotransformation of permethrin to
estrogenic metabolites in fish. Chem Res Toxicol 23:1568–1575. https://doi.org/10.1021/
tx100167x
11. Jin Y, Wang W, Xu C et al (2008) Induction of hepatic estrogen-responsive gene transcription
by permethrin enantiomers in male adult zebrafish. Aquat Toxicol 88:146–152. https://doi.org/
10.1016/j.aquatox.2008.04.004
12. Gan J, Wang C, Zhang Q et al (2010) Integrative assessment of enantioselectivity in endocrine
disruption and immunotoxicity of synthetic pyrethroids. Environ Pollut 158:1968–1973.
https://doi.org/10.1016/j.envpol.2009.10.027
13. Katsuda Y (2012) Progress and future of pyrethroids. Top Curr Chem 314:1–30
14. Martel J (1992) The development and manufacture of pyrethroid insecticides. In: Chirality in
industry – the commercial manufacture and applications of optically active compounds. Wiley,
Chichester, p 87
15. Soderlund DM (2010) Toxicology and mode of action of pyrethroid insecticides, 3rd edn.
Elsevier, London
16. Rehman H, Aziz AT, Saggu S et al (2014) Systematic review on pyrethroid toxicity with
special reference to deltamethrin. J Entomol Zool Stud 2:60–70. https://doi.org/10.1016/j.
carres.2006.12.019
17. Chang J, Wang Y, Wang H et al (2016) Bioaccumulation and enantioselectivity of type I and
type II pyrethroid pesticides in earthworm. Chemosphere 144:1351–1357. https://doi.org/10.
1016/j.chemosphere.2015.10.011
18. Cahn RS, Ingold CK, Prelog V (1956) The specification of asymmetric configuration in
organic chemistry. Experientia 12:81–94. https://doi.org/10.1007/BF02157171
19. Prelog V, Helmchen G (1982) Basic principles of the CIP-system and proposals for a revision.
Angew Chemie Int Ed Engl 21:567–583. https://doi.org/10.1002/anie.198205671
20. Smith SW (2009) Chiral toxicology: it’s the same thing only different. Toxicol Sci 110:4–30.
https://doi.org/10.1093/toxsci/kfp097
170
C. E. T. Parente et al.