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. 2016 May 26:6:26797.
doi: 10.1038/srep26797.

Environmental Fate of Chiral Herbicide Fenoxaprop-ethyl in Water-Sediment Microcosms

Xu Jing  1 , Guojun Yao  1 , Donghui Liu  1 , Mingke Liu  1 , Peng Wang  1 , Zhiqiang Zhou  1
Affiliations

Environmental Fate of Chiral Herbicide Fenoxaprop-ethyl in Water-Sediment Microcosms

Xu Jing et al. Sci Rep. .

Abstract

The environmental fate of the herbicide fenoxaprop-ethyl (FE) in water, sediment and water-sediment microcosm was studied and degradation products fenoxaprop (FA), ethyl-2-(4-hydroxyphenoxy)propanoate (EHPP), 2-(4-hydroxyphenoxy)propanoic acid (HPPA) and 6-chloro-2,3-dihydrobenzoxazol-2-one (CDHB) were monitored. FE, FA, EHPP and HPPA were chiral and the environmental behavior was investigated on an enantiomeric level. In water, sediment and water-sediment microcosms, fenoxaprop-ethyl degraded very fast with half-lives less than 1 day and it was found the herbicidally inactive S-enantiomer degraded faster. Fenoxaprop was the main primary degradation product which was quickly formed and the further degradation was relatively slow with half-lives of 6.4-12.4 days, and the S-enantiomer degraded faster too. EHPP, HPPA and CDHB could be found and S-EHPP and S-HPPA were degraded preferentially. The effects of microorganism and water content were investigated and it was found that the enantioselectivity was attributed to microorganisms. In sediment, the main degradation pathway of fenoxaprop-ethyl was hydrolysis and the degradation rate of fenoxaprop-ethyl increased with water content. The degradation products and enantioselectivity should be considered for the impact of fenoxaprop-ethyl on the aquatic system.

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Figures

Figure 1
Figure 1. Chemical structures of fenoxaprop-ethyl (FE) and the four degradation products.
*Indicates chiral center.
Figure 2
Figure 2
Concentration-time curves of FE and its degradation products in (A) water; (B) sterilized water; (C) sediment; (D) sterilized sediment. Starting concentration of FE in water, sterilized water, sediment and sterilized sediment were 1.38, 1.38, 6.91 and 6.91 μmol/kg, respectively.
Figure 3
Figure 3. EF values-time curves of FE and its degradation products in water, water of W-C microcosm, water of S-C microcosm, sediment, sediment of W-C microcosm, sediment of S-C microcosm.
(A) FE; (B) FA; (C) EHPP; (D) HPPA.
Figure 4
Figure 4
Distribution of FE in water and sediment in (A) W-C microcosm; (B) S-C microcosm.
Figure 5
Figure 5. The effect of water content on the degradation of FE and its degradation products.
(A) FE; (B) FA; (C) CDHB; (D) EHPP and HPPA.
See this image and copyright information in PMC

References

    1. Pornprom T., Mahatamnuchoke P. & Usui K. The role of altered acetyl‐CoA carboxylase in conferring resistance to fenoxaprop‐P‐ethyl in Chinese sprangletop (Leptochloa chinensis (L.) Nees). Pest management science 62, 1109–1115 (2006). - PubMed
    1. Bieringer H. H. H. r., Langelueddeke G. & Handte P., R. HOE 33171-a new selective herbicide for the control of annual and perennial warm climate grass weeds in broadleaf crops. Proc. Brit. Crop Prot. Conf. Weeds 1, 11–17 (1982).
    1. Li L., Bi Y., Liu W., Yuan G. & Wang J. Molecular basis for resistance to fenoxaprop-p-ethyl in American sloughgrass (Beckmannia syzigachne Steud.). Pesticide Biochemistry and Physiology 105, 118–121 (2013).
    1. Lucini L. & Pietro Molinari G. Residues of the herbicide fenoxaprop‐P‐ethyl, its agronomic safener isoxadifen‐ethyl and their metabolites in rice after field application. Pest management science 66, 621–626 (2010). - PubMed
    1. Chen X. et al.. Residues and Dissipation of the Herbicide Fenoxaprop-P-ethyl and Its Metabolite in Wheat and Soil. Bulletin of Environmental Contamination and Toxicology volume 87, 50–53(54) (2011). - PubMed

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