Abstract
The study is aiming to present the fate of chiral pesticides, the different behaviour of these optic active isomers in the environment and their ecotoxicological effects, as well as separation techniques available for the chiral pesticides studies. We conclude that there is a tremendous need to enlarge the studies related to the enantioselective behaviour of chiral pesticides in different contaminated environmental components, as well as their ecotoxicity to biota and humans.
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References
Aboul Eish MYZ, Wells MJM (2008) Monitoring stereoselective degradation of metolachlor in a constructed wetland: use of statistically valid enantiomeric and diastereomeric fractions as opposed to ratios. J Chromatogr Sci 46:269–275
Ali I, Khan TA, Aboul-Enein HY, Asim M (2010) Chiral analyses of pollutants by capillary electrophoresis. Open Chem Biomed Method J 3:46–55
Bicchi C, Liberto E, Cagliero C, Cordero C, Sgorbini B, Rubiolo P (2008) Conventional and narrow bore short capillary columns with cyclodextrin derivatives as chiral selectors to speed-up enantioselective gas chromatography and enantioselective gas chromatography–mass spectrometry analyses. J Chromatogr A 1212:114–123
Bidleman TF, Wong F, Backe C, Sodergren A, Brorstrom-Lunden E, Helm PA, Stern GA (2004) Chiral signatures of chlordanes indicate changing sources to the atmosphere over the past 30 years. Atmos Environ 38:5963–5970
Bordajandi LR, Ramos L, Jose GM (2006) Determination of toxaphene enantiomers by comprehensive two-dimensional gas chromatography with electron-capture detection. J Chromatogr A 1125:220–228
Chankvetadze B (2007) Enantioseparations by using capillary electrophoretic techniques. The story of 20 and a few more years. J Chromatogr A 1168:45–70
Chunxiu P, Baochun S, Xuejun Z, Datong Z, Xiuzhu X (2006) Enantioseparation of four aryloxyphenoxypropionic acid herbicides by HPLC on CDMPC and (S, S)-whelk-O 1. Chin J Anal Chem 34(2):159–164
Desiderio C, Polcaro CM, Padiglioni E, Fanali S (1997) Enantiomeric separation of acidic herbicides by capillary electrophoresis using vancomycin as chiral selector. J Chromatogr A 781:503–513
Draghici C (2007) Chiral selectors used as additives in the electrolyte buffer for enantioseparation by capillary electrophoresis. Part I Ovidius Univ Ann Chem 18(2):174–178
Fidalgo-Used N, Montes-Bayon M, Blanco-Gonzalez E, Sanz-Medel A (2008) Enantioselective determination of the organochlorine pesticide bromocyclen in spiked fish tissue using solid-phase microextraction coupled to gas chromatography with ECD and ICP–MS detection. Talanta 75:710–716
Garrison AW (2011) An introduction to pesticide chirality and the consequences of stereoselectivity. In: Garrison AW, Gan J, Liu W (eds) Chiral pesticides: stereoselectivity and its consequences, vol 1085, ACS symposium series. American Chemical Society, Washington, DC, pp 1–7
Gübitz G, Schmid MG (2008) Chiral separation by capillary electromigration techniques. J Chromatogr A 1204:140–156
Hegeman WJM, Laane RWPM (2002) Enantiomeric enrichment of chiral pesticides in the environment. Rev Environ Contam Toxcicol 173:85–116
Hühnerfuss H, Shah MR (2009) Enantioselective chromatography – A powerful tool for the discrimination of biotic and abiotic transformation processes of chiral environmental pollutants. J Chromatogr A 1216:481–502
Jantunen LM, Kylin H, Bidleman TF (2004) Air–water gas exchange of a-hexachlorocyclohexane enantiomers in the South Atlantic Ocean and Antarctica. Deep Sea Res II 51:2661–2672
Jin Y, Wang W, Xu C, Fu Z, Liu W (2008) Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish. Aquat Toxicol 88:146–152
Juraske R, Castells F, Vijay A, Munoz P, Antón A (2009) Uptake and persistence of pesticides in plants: measurements and model estimates for imidacloprid after foliar and soil application. J Hazard Mater 165:683–689
Klein C, Schneider RJ, Meyer MT, Aga DS (2006) Enantiomeric separation of metolachlor and its metabolites using LC–MS and CZE. Chemosphere 62:1591–1599
Kurt-Karakus PB, Bidleman TF, Muir DCG, Struger J, Sverko E, Cagampan SJ, Small JM, Jantunen LM (2010) Comparison of concentrations and stereoisomer ratios of mecoprop, dichlorprop, and metolachlor in Ontario streams, 2006–2007 vs. 2003–2004. Environ Pollut 158:1842–1849
Lee W-Y, Iannucci-Berger WA, Eitzer BD, White JC, Mattina MJI (2003) Plant uptake and translocation of air-borne chlordane and comparison with the soil-to-plant route. Chemosphere 53:111–121
Li L, Zhou S, Jin L, Zhang C, Liu W (2010) Enantiomeric separation of organophosphorus pesticides by high-performance liquid chromatography, gas chromatography and capillary electrophoresis and their applications to environmental fate and toxicity assays. J Chromatogr B 878:1264–1276
Li X, Liu Y, Hu C, Bai L, Gao B, Huang K (2011) Direct optical resolution of chiral pesticides by high performance liquid chromatography. Chin J Chem Eng 19(4):603–609
Liu D, Wang P, Zhou W, Gu X, Chen Z, Zhou Z (2006) Direct chiral resolution and its application to the determination of fungicide benalaxyl in soil and water by high-performance liquid chromatography. Anal Chim Acta 555:210–216
Liu D, Wang P, Zhu W, Gu X, Zhou W, Zhou Z (2008) Enantioselective degradation of fipronil in Chinese cabbage (Brassica pekinensis). Food Chem 110:399–405
Liu H, Zhao M, Zhang C, Ma Y, Liu W (2008) Enantioselective cytotoxicity of the insecticide bifenthrin on a human amnion epithelial (FL) cell line. Toxicology 253:89–96
Liu H, Huang R, Xie F, Zhang S, Shi J (2012) Enantioselective phytotoxicity of metolachlor against maize and rice roots. J Hazard Mater 217–218:330–337
Ma Y, Chen L, Lu X, Chu H, Xu C, Liu W (2009) Enantioselectivity in aquatic toxicity of synthetic pyrethroid insecticide fenvalerate. Ecotoxicol Environ Saf 72:1913–1918
McHugh B, Law RJ, Allchin CR, Rogan E, Murphy S, Foley MB, Glynn D, McGovern E (2007) Bioaccumulation and enantiomeric profiling of organochlorine pesticides and persistent organic pollutants in the killer whale (Orcinus orca) from British and Irish waters. Mar Pollut Bull 54:1724–1731
Nillos MG, Gan J, Schlenk D (2010) Chirality of organophosphorus pesticides: analysis and toxicity. J Chromatogr B 878:1277–1284
Perez-Fernandez V, Garcia MA, Marina ML (2010) Characteristics and enantiomeric analysis of chiral pyrethroids. J Chromatogr A 1217:968–989
Pérez-Fernández V, García MÁ, Marina ML (2011) Chiral separation of agricultural fungicides. J Chromatogr A 1218:6561–6582
Pérez-Fernández V, García MÁ, Marina ML (2011) Chiral separation of metalaxyl and benalaxyl fungicides by electrokinetic chromatography and determination of enantiomeric impurities. J Chromatogr A 1218:4877–4885
Perez-Fernandez V, Dominguez-Vega E, Chankvetadze B, Crego AL, Garcia MA, Marina ML (2012) Evaluation of new cellulose-based chiral stationary phases Sepapak-2 and Sepapak-4 for the enantiomeric separation of pesticides by nano liquid chromatography and capillary electrochromatography. J Chromatogr A 1234:22–31
Ramezani MK, Oliver DP, Kookana RS, Lao W, Gill G, Preston C (2010) Faster degradation of herbicidally-active enantiomer of imidazolinones in soils. Chemosphere 79:1040–1045
Sanchez-Rasero F, Matallo MB, Dios G, Romero E, Pena A (1998) Simultaneous determination and enantiomeric resolution of mecoprop and dichlorprop in soil samples by high-performance liquid chromatography and gas chromatography–mass spectrometry. J Chromatogr A 799:355–360
Seemamahannop R, Berthod A, Maples M, Kapila S, Armstrong DW (2005) Uptake and enantioselective elimination of chlordane compounds by common carp (Cyprinus carpio, L.). Chemosphere 59:493–500
Sun M, Liu D, Dang Z, Li R, Zhou Z, Wang P (2012) Enantioselective behavior of malathion enantiomers in toxicity to beneficial organisms and their dissipation in vegetables and crops. J Hazard Mater 237–238:140–146
Venier M, Hites RA (2007) Chiral organochlorine pesticides in the atmosphere. Atmos Environ 41:768–775
Wong CS (2006) Environmental fate processes and biochemical transformations of chiral emerging organic pollutants. Anal Bioanal Chem 386:544–558
Xu C, Tu W, Lou C, Hong Y, Zhao M (2010) Enantioselective separation and zebrafish embryo toxicity of insecticide beta-cypermethrin. J Environ Sci 22(5):738–743
Xu D, Wen Y, Wang K (2010) Effect of chiral differences of metolachlor and its (S)-isomer on their toxicity to earthworms. Ecotoxicol Environ Saf 73:1925–1931
Ye J, Wu J, Liu W (2009) Enantioselective separationand analysis of chiral pesticides by high-performance liquid chromatography. Trends Anal Chem 28(10):1148–1163
Ye J, Zhao M, Liu J, Liu W (2010) Enantioselectivity in environmental risk assessment of modern chiral pesticides. Environ Pollut 158:2371–2383
Yip Y-C, Wong S-K, Choi S-M (2011) Assessment of the chemical and enantiomeric purity of organic reference materials. Trends Anal Chem 30(4):628–640
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Drăghici, C., Chirila, E., Sica, M. (2013). Enantioselectivity of Chiral Pesticides in the Environment. In: Simeonov, L., Macaev, F., Simeonova, B. (eds) Environmental Security Assessment and Management of Obsolete Pesticides in Southeast Europe. NATO Science for Peace and Security Series C: Environmental Security. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-6461-3_7
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DOI: https://doi.org/10.1007/978-94-007-6461-3_7
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