Isomerization of chiral pesticides in the environment

Journal of Pesticide Science

Volumn 37, Issue 1, 2012, Pages 1-14

  Katagi, Toshiyuki ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

Chiral pesticides; Enantiomerization; Hydrolysis; Isomerization; Photolysis; Soil and plant metabolism

Indexed keywords

EID: 84861660030     PISSN: 1348589X     EISSN: 13490923     Source Type: Journal    
DOI: 10.1584/jpestics.D11-036     Document Type: Review

References (136)

1. N. Kurihara, J. Miyamoto, G. D. Paulson, B. Zeeh, M. W. Skidmore, R. M. Hollingworth and H. A. Kuiper: Pure Appl. Chem. 69, 2007-2025 (1997).
2. B. S. Sekhon J. Pestic. Sci. 34, 1-12 (2009).
3. J. O. Margans, J. L. Alonso-Prados, J. M. García-Baudín Chemosphere 49, 461-469 (2002).
4. S. W. Smith Toxicol. Sci. 110, 4-30 (2009).
5. A. Williams Pestic. Sci. 46, 3-9 (1996).
6. J. K. Stanley and B. W. Brooks Integr. Environ. Assess. Manag. 5, 364-373 (2009).
7. U.S.EPA: EFED Interim Policy for Stereoisomeric Pesticides. http://www.epa.gov/oppefed1/ecorisk-ders/stereoisomer-policy.htm, 2000.
8. European Union: Off. J. Eur. Union L309, 1-50 (2009).
9. M. G. Nillos, J. Gan and D. Schlenk J. Chromatogr. B 878, 1277-1284 (2010).
10. L. Li, S. Zhou, L. Jin, C. Zhang and W. Liu J. Chromatogr. B 878, 1264-1276 (2010).
11. V. Pérez-Fernández, M. A. García, M. L. Marina J. Chromatogr. A 1217, 968-989 (2010).
12. C. S. Wong Anal. Bioanal. Chem. 386, 544-558 (2006).
13. H. P. Buser and E. Francotte: "Chiral Separations-Applications and Technology," ACS Professional Reference Book Series, ed. by S. Ahuja, American Chemical Society, Washington D. C., Chap. 5, pp. 93-138, 1997.
14. J. Ye, J. Wu and W. Liu Trends Anal. Chem. 28, 1148-1163 (2009).
15. Z. El Rassi Electrophoresis 18, 2465-2481 (1997).
16. B. Siffert and A. Naidja Clay Miner. 27, 109-118 (1992).
17. M. Matallo, E. Romero, F. Sánchez-Rasero, A. Peña and G. Dios J. Environ. Sci. Health 33B, 51-66 (1998).
18. M. Oravec, Z. Šimek and I. Holoubek Colloids Surf. A 359, 60-65 (2010).
19. W. Liu, J. Ye and M. Jin J. Agric. Food Chem. 57, 2087-2095 (2009).
20. J. Ye, M. Zhao, J. Liu and W. Liu Environ. Pollut. 158, 2371-2383 (2010).
21. T. F. Bidleman and R. L. Falconer Environ. Sci. Technol. 33, 206A-209A (1999).
22. I. Ali, V. K. Gupta and H. Y. Aboul-Enein: Curr. Sci. 84, 152-156 (2003).
23. A. W. Garrison Environ. Sci. Technol. 40, 16-23 (2006).
24. T. Harner, K. Wiberg and R. Norstrom Environ. Sci. Technol. 34, 218-220 (2000).
25. W. J. M. Hegeman and R. W. P. M. Laane Rev. Environ. Contam. Toxicol. 173, 85-116 (2002).
26. I. J. Buerge, T. Poiger, M. D. Müller and H. -R. Buser Environ. Sci. Technol. 37, 2668-2674 (2003).
27. H. P. E. Kohler, W. Angst, W. Giger, C. Kang, S. Müller and M. J. F. Suter Chimia 51, 947-951 (1997).
28. T. A. Müller and H. P. E. Kohler Appl. Microbiol. Biotechnol. 64, 300-316 (2004).
29. Y. Wen, C. Li, Z. Fang, S. Zhuang and W. Liu J. Agric. Food Chem. 59, 1924-1930 (2011).
30. M. Reist, B. Testa, P. -A. Carrupt, M. Jung and V. Schurig Chirality 7, 396-400 (1995).
31. T. Katagi Rev. Environ. Contam. Toxicol. 182, 1-189 (2004).
32. T. Katagi Rev. Environ. Contam Toxicol. 175, 79-261 (2002).
33. th ed., A Wiley-International Publication, John Wiley & Sons, New York (2001).
34. B. Testa, P. -A. Carrupt and J. Gal Chirality 5, 105-111 (1993).
35. C. Pepper, H. J. Smith, K. J. Barrel, P. J. Nicholls and M. J. E. Hewlins Chirality 6, 400-404 (1994).
36. M. Reist, L. H. Christiansen, P. Christoffersen, P. A. Carrupt and B. Testa Chirality 7, 469-473 (1995).
37. Lambda-cyhalothrin, Demand CS Insecticide. Proposed Regulatory Decision Document, PRDD 2003-03. Pesticide Management Regulatory Agency, Health Canada, Ontario, pp. 39 (2003).
38. J. V. Pivnichny, B. H. Arison, F. A. Preiser, J. S. K. Shim and H. Mrozik J. Agric. Food Chem. 36, 826-828 (1988).
39. L. Patria, N. Merlet and M. Dore Environ. Technol. 16, 315-327 (1995).
40. M. Friedman J. Agric. Food Chem. 47, 3457-3479 (1999).
41. European Food Safety Authority: EFSA Scientific Report 107, 1-81 (2007)
42. G. Severin Chirality 4, 222-226 (1992).
43. M. Reist, P.-A. Carrupt, B. Testa, S. Lehmann and J. J. Hansen Helv. Chim. Acta 79, 767-778 (1996).
44. M. Reist, P. A. Carrupt, E. Francotte and B. Testa Chem. Res. Toxicol. 11, 1521-1528 (1998).
45. W. Liu, S. Qin and J. Gan J. Agric. Food Chem. 53, 3814-3820 (2005).
46. T. Katagi J. Agric. Food Chem. 41, 2178-2183 (1993).
47. R. Kodaka, T. Sugano and T. Katagi: J Pestic Sci. 34, 27-36 (2009).
48. R. J. Maguire J. Agric. Food Chem. 38, 1613-1617 (1990).
49. C. L. Wilson J. Chem. Soc. 1550-1553 (1936).
50. W. A. Bonner, N. E. Blair and R. M. Lemmon Origins Life 9, 279-290 (1979).
51. N. Takahashi, N. Mikami, T. Matsuda and J. Miyamoto J. Pestic. Sci. 10, 629-642 (1985).
52. L. O. Ruzo, R. L. Holmstead and J. E. Casida J. Agric. Food Chem. 25, 1385-1394 (1977).
53. L. O. Ruzo and J. E. Casida J. Agric. Food Chem. 29, 702-706 (1981).
54. K. Ohsawa and J. E. Casida J. Agric. Food Chem. 27, 1112-1120 (1979).
55. M. Nishiyama, Y. Suzuki and T. Katagi J. Pestic. Sci. 35, 447-455 (2010).
56. T. Katagi J. Agric. Food Chem. 39, 1351-1356 (1991).
57. European Food Safety Authority: EFSA Journal 8 (12): 1872, 1-72 (2010)
58. M. Ramezani, D. P. Oliver, R. S. Kookana, G. Gill and C. Preston J. Environ. Sci. Health B43, 105-112 (2008).
59. R. Kodaka, T. Sugano and T. Katagi Environ. Toxicol. Chem. 25, 310-316 (2006).
60. B. D. Hill J. Agric. Food Chem. 29, 107-110 (1981).
61. H. Perschke and M. Hussain J. Agric. Food Chem. 40, 686-690 (1992).
62. W. Leicht, R. Fuchs and M. Londershausen Pestic. Sci. 48, 325-332 (1996).
63. S. Qin and J. Gan J. Agric. Food Chem. 55, 5734-5739 (2007).
64. M. G. Nillos, S. Qin, C. Larive, D. Schlenk and J. Gan J. Agric. Food Chem. 57, 6938-6943 (2009).
65. Z. Li, T. Wu, Q. Li, B. Zhang, W. Wang and J. Li J. Chromatogr. A 1217, 5718-5723 (2010).
66. J. You and M. J. Lydy J. Chromatogr. A 1166, 181-190 (2007).
67. Z. Y. Li, Y. C. Zhang, Q. L. Li, W. X. Wang and J. Y. Li Chinese J. Anal. Chem. 38, 237-240 (2010).
68. H. Moser, G. Rihs and H. Sauter Z. Naturforsch. B: Chem. Sci. 87B, 451-462 (1982).
69. M. D. Müller, T. Poiger and H. R. Buser J. Agric. Food Chem. 49, 42-49 (2001).
70. T. Poiger, M. D. Müller, I. J. Buerge, M. E. Balmer and H.-R. Buser Adv. Mass Spectrom. 16, 59-77 (2004).
71. J. P. Kutter and T. J. Class Chromatographia 33, 103-112 (1992).
72. P. González Audino, S. A. Licastro and E. Zerba Pestic. Manag. Sci. 58, 183-189 (2002).
73. A. J. Hutt and J. Caldwell J. Pharm. Pharmacol. 35, 693-704 (1983).
74. V. Wsól, L. Skálová and B. Szotáková Curr. Drug Metab. 5, 517-533 (2004).
75. M. E. Tanner Acc. Chem. Res. 35, 237-246 (2002).
76. A. J. Carnell Adv. Biochem. Eng./Biotechnol. 63, 57-72 (1999).
77. T. Yoshimura and N. Esaki J. Biosci. Bioeng. 96, 103-109 (2003).
78. H. -R. Buser and M. D. Müller Environ. Sci. Technol. 31, 1960-1967 (1997).
79. D. W. Bewick Pestic. Sci. 17, 349-356 (1986).
80. M. D. Müller and H. -R. Buser Environ. Sci. Technol. 31, 1953-1959 (1997).
81. O. Wink and U. Luley Pestic. Sci. 22, 31-40 (1988).
82. J. M. Schneiderheinze, D. W. Armstrong and A. Berthod Chirality 11, 330-337 (1999).
83. E. Romero, M. B. Matallo, A. Peña, F. Sánchez-Rasero, Ph. Schmitt-Kopplin and G. Dios: Environ. Pollut. 111, 209-215 (2001).
84. A. Messina and M. Sinibaldi Electrophoresis 28, 2613-2618 (2007).
85. J. Diao, C. Lv, X. Wang, Z. Dang, W. Zhu and Z. Zhou J. Agric. Food Chem. 57, 5865-5871 (2009).
86. J. Diao, P. Xu, P. Wang, Y. Lu, D. Lu and Z. Zhou Environ. Sci. Technol. 44, 2042-2047 (2010).
87. Y. Zhang, D. Liu, J. Diao, Z. He, Z. Zhou, P. Wang and X. Li J. Agric. Food Chem. 58, 12878-12884 (2010).
88. H. -R. Buser, M. D. Müller, T. Poiger and M. E. Balmer Environ. Sci. Technol. 36, 221-226 (2002).
89. C. Marucchini and C. Zadra Chirality 14, 32-38 (2002).
90. A. Monkiedje, M. Spiteller and K. Bester Environ. Sci. Technol. 37, 707-712 (2003).
91. X. Wang, G. Jia, J. Qiu, J. Diao, W. Zhu, C. Lv and Z. Zhou Chirality 19, 300-306 (2007).
92. X. Gu, P. Wang, D. Liu, C. Lv, Y. Lu and Z. Zhou Chirality 20, 125-129 (2008).
93. S. Chen and W. Liu Bull Environ. Contam. Toxicol. 82, 327-331 (2009).
94. S. Sakata, N. Mikami and H. Yamada J. Pestic. Sci. 17, 169-180 (1992).
95. R. Kodaka, Y. Suzuki, T. Sugano and T. Katagi J. Pestic. Sci. 32, 393-401 (2007).
96. Z. Y. Li, Z. C. Zhang, L. Zhang and L. Leng Bull. Environ. Contam. Toxicol. 80, 335-339 (2008).
97. S. Qin and J. Gan J. Agric. Food Chem. 54, 9145-9151 (2006).
98. P. W. Lee, W. R. Powell, S. M. Stearns and O. J. McConnell J. Agric. Food Chem. 35, 384-387 (1987).
99. Z. Li, Z. Zhang, L. Zhang and L. Leng Chemosphere 76, 509-516 (2009).
100. I. J. Buerge, T. Poiger, M. D. Müller and H. R. Buser Environ. Sci. Technol. 40, 5443-5450 (2006).
101. Z. Li, Y. Zhang, Q. Li, W. Wang and J. Li Environ. Sci. Technol. 45, 2797-2803 (2011).
102. A. W. Garrison, J. K. Avants and W. J. Jones Environ. Sci. Technol. 45, 2186-2193 (2011).
103. K. Itoh J. Pestic. Sci. 16, 35-40 (1991).
104. Z. Y. Li, Z. C. Zhang, L. Zhang and L. Leng Bull. Environ. Contam. Toxicol. 79, 153-157 (2007).
105. W. J. Jones, C. S. Mazur, J. F. Kenneke and A. W. Garrison Environ. Sci. Technol. 41, 8301-8307 (2007).
106. H. Tan, Y. Cao, T. Tang, K. Qian, W. L. Chen and J. Li Sci. Total Environ. 407, 428-437 (2008).
107. M. Négre, M. Gennari, V. Andreoni, R. Ambrosoli and L. Celi J. Environ. Sci. Health, 28B, 545-576 (1993).
108. C. Zipper, C. Bolliger, T. Fleischmann, M. J. F. Suter, W. Angst, M. D. Müller and H. P. E. Kohler Biodegradation 10, 271-278 (1999).
109. Y. Lu, J. Diao, X. Gu, Y. Zhang, P. Xu, P. Wang and Z. Zhou Chirality 23, 424-428 (2011).
110. K. Itoh J. Pestic. Sci. 16, 85-91 (1991).
111. Y. Lin, P. Han, X. -Y. Li, K. Shih and J. -D. Gu J. Hazard Mater. 192, 1633-1640 (2011).
112. R. H. Shimabukuro and B. L. Hoffer Pestic. Biochem. Physiol. 51, 68-82 (1995).
113. X. Cai, W. Liu and G. Sheng J. Agric. Food Chem. 56, 2139-2146 (2008).
114. X. Zhang, S. Wang, Y. Wang, T. Xia, J. Chen and X. Cai J. Hazard Mater. 186, 876-882 (2011).
115. X. Gu, Y. Lu, P. Wang, Z. Dang, Z. Zhou Food Chem. 121, 264-267 (2010).
116. C. Zadra, C. Marucchini and A. Zazzerini J. Agric. Food Chem. 50, 5373-5377 (2002).
117. L. O. Ruzo and J. E. Casida J. Agric. Food Chem. 27, 572-575 (1979).
118. L. M. Cole, J. E. Casida and L. O. Ruzo J. Agric. Food Chem. 30, 916-920 (1982).
119. K. Furuzawa, N. Mikami, H. Yamada and J. Miyamoto J. Pestic. Sci. 11, 253-260 (1986).
120. European Food Safety Authority: Final Addendum to the Draft Assessment Report (DAR) and Additional Report (AR)public version, Tau-fluvalinate. pp. 1-143 (2010).
121. T. Clark: British Crop Protection Conference-Pests and Diseases, Vol. 2, 475-482 (1986).
122. T. Clark, W. -C. Wong and K. Vogeler Pestic. Sci. 33, 447-453 (1991).
123. A. Miyazaki, T. Nakamura and S. Marumo J. Pestic. Sci. 10, 727-728 (1985).
124. P. Wang, S. R. Jiang, J. Qiu, Q. X. Wang, P. Wang and Z. Q. Zhou Pestic. Biochem. Physiol. 82, 197-204 (2005).
125. D. Liu, P. Wang, W. Zhu, X. Gu, W. Zhou and Z. Zhou Food Chem. 110, 399-405 (2008).
126. S. Qin, R. Budd, S. Bondarenko, W. Liu and J. Gan J. Agric. Food Chem. 54, 5040-5045 (2006).
127. S. Qin, W. Liu and J. Gan: "Synthetic Pyrethroids. Occurrence and Behaviour in Aquatic Environments," ed. by J. Gan, F. Spurlock, P. Hendley and D. P. Weston, ACS Symp. Ser. 991, American Chemical Society, Washington D. C., Chap. 12, pp. 238-253, 2008.
128. C. Zipper, M. J. -F. Suter, S. B. Haderlein, M. Gruhl and H. -P. E. Kohler Environ. Sci. Technol. 32, 2070-2076 (1998).
129. H. -R. Buser and M. D. Müller Environ. Sci. Technol. 32, 626-633 (1998).
130. P. B. Kurt-Karakus, T. F. Bidleman, D. C. G. Muir, J. Struger, E. Sverko, S. J. Cagampan, J. M. Small and L. M. Jantunen Environ. Pollut. 158, 1842-1849 (2010).
131. K. M. Erstfeld Chemosphere 39, 1737-1769 (1999).
132. R. J. Maguire, J. H. Carey, J. H. Hart, R. J. Tkacz and H. B. Lee J. Agric. Food Chem. 37, 1153-1159 (1989).
133. D. C. G. Muir, A. L. Yarechewski and B. R. Neal Environ. Toxicol. Chem. 11, 581-591 (1992).
134. C. -Y. Shen, X. -W. Cao, W. -J. Shen, Y. Jiange, Z. -Y. Zhao, B. Wu, K. -Y. Yu, H. Liu and H. -Z. Lian Talanta 84, 141-147 (2011).
135. T. J. Class Int. J. Environ. Anal. Chem. 49, 189-205 (1992).
136. H. Kuang, H. Miao, X. Hou, Y. Zhao, J. Shen and Y. Wu J. Sci. Food Agric. 90, 1374-1379 (2010).