Description:
This task involves process research to determine the environmental occurrence and fate of enantiomers of selected chiral pesticides, PCBs and other chiral pollutants with an emphasis on currently-used modern pesticides expected to have short to intermediate environmental half-lives. Enantiomeric selectivity manifests itself during biologically-mediated environmental processes (e.g., enzyme catalyzed transformations, transport across membranes), but not during abiotic processes. One enantiomer thus reacts more slowly than the other during microbial degradation and thereby comes to predominate in water/sediment systems, in plant and animal tissues, and in food residues. In addition, enantiomers have different biological effects: one is more toxic than the other, and, for chiral endocrine disrupters, exhibits differential disruption activity. The approach to this research involves 5 steps: 1) development of analytical techniques to separate enantiomers; 2) analysis of water, sediment, soil, biota and human exposure samples expected to contain chiral pollutants to determine the occurrences and enantiomeric ratios; 3) measurement of enantiomer degradation in selected environmental matrices to determine selectivity and rates of enantiomer degradation; 4) preparative separation/collection of the enantiomers of important pesticides and other pollutants for effects studies; and 5) measurement of the effects of the separate enantiomers of pesticides using various toxicity endpoints; testing will be done by other EPA laboratories and extramurally.
Keywords:
CHIRAL, POLLUTANTS, PESTICIDES, PCBS, ENANTIOMERS, STEREOISOMERS, ENANTIOSELECTIVE,
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Project Information:
Progress
:GC, WPLC and CE methods have been developed to separate the enantiomers of a variety of chiral pesticides, PCBs and other chiral pollutants. APM 127 was delivered to OPP July 2001: "Transformation and Occurrences of the Enantiomers of Chiral Pesticides in Environmental Matrices and Food Products." An EPA internal report on the microbial transformation of metolachlor in the field was submitted to OPP in March 2002. Review articles on the analysis of chiral pollutants and on the enantioselectivity of chiral agrochemicals were published in 2000 and 2002, respectively. Four journal articles on the GC-MS analysis, occurrences and fate of the enantiomers of chiral PCBs in sediment and in aquatic and riparian biota were published in 2000-2002. Research has been completed on the occurrence of persistent PBT pesticides and their enantiomers in alligator livers from Lake Apopka, FL, on the enantiomeric ratios of PCB84 in rat tissue, and the ratios of PCB95 in human exposure samples (soil, dust, dermal and floor wipes, etc.). The enantioselective degradation of metalaxyl, fipronil and other less persistent pesticides as well as the water chlorination product bromochloroacetic acid has been followed in laboratory microcosms. Our article in Nature showed that the enantioselectivity occurring during microbial transformation of chiral pesticides in soils may be substantially altered by environmental changes imposed on the soils. The (R)-enantiomer of o,p'-DDT was shown by endocrine disrupter screening tests to have much more estrogenic activity than the (S)-enantiomer. Screening for endocrine disruption activity of separated enantiomers of eleven chiral pesticides has been completed. Fipronil, a modern chiral insecticide, was shown to be enantioselective in its toxicity to aquatic invertebrates.
Relevance
:Up to 25% of pesticides are chiral, as are many PCBs and other environmental pollutants. The enantiomers of these pollutants usually degrade at different rates in the environment, thus leading to differences in persistence, and usually exhibit different toxicities toward target and non-target species. Increased accuracy of environmental and human risk assessment will result from consideration of enantioselectivity in exposure and effects of chiral pollutants; in modeling the fate and effects of chiral pollutants, the two enantiomers should be considered as two compounds. Use of only the target-active enantiomer of pesticides will reduce the pollutant load and avoid any adverse effects of the other enantiomer.
Clients
:Jim Hetrick and Sid Abel, EFED/OPP
Project IDs:
ID Code
:20164
Project type
:OMIS