Enantioselective phytoeffects of chiral pesticides

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 6, 2009, Pages 2087-2095

  Liu, Weiping ^a   Ye, Jing ^b   Jin, Meiqing ^b  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Chiral pesticides; Herbicides; Nontarget plants; Phytotoxicity; Plant growth regulators; POPs

Indexed keywords

AGRICULTURAL CHEMICAL; CHLORDANE; CHLORPHENOTANE; HERBICIDE; PHYTOHORMONE;

ARTICLE; CHEMISTRY; DRUG EFFECT; METABOLISM; PLANT; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

AGROCHEMICALS; CHLORDAN; DDT; HERBICIDES; PLANT GROWTH REGULATORS; PLANTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 64549112177     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900079y     Document Type: Article

References (55)

1. Kallenborn, R.; Hühnerfuss, H. Links between chirality and life processes. In Chiral Environmental Pollutants - Trace Analysis and Ecotoxicology; Springer-Verlag: Heidelberg, Germany, 2001; PP 3
2. Roelfes, G. DNA and RNA induced enantioselectivity in chemical synthesis. Mol. Biosyst. 2007, 3, 126-135.
3. Vetter, W. Enantioselective fate of chiral chlorinated hydrocarbons and their metabolites in environmental samples. Food Rev. Int. 2001, 17, 113-182.
4. Liu, W. P.; Gan, J. Y.; Schlenk, D.; Jury, W. A. Enantioselectivity in environmental safety of current chiral insecticides. Proc. Natl Acad. Sci. U.S.A. 2005, 102, 701-705.
5. Wiberg, K.: Letcher, R. J.; Sandau, C. D.; Norstrom, R. J.; Tysklind, M.; Bidleman, T. F. The enantioselective bioaccumulation of chiral chlordane and α-HCH contaminants in the polar bear food chain. Environ. Sci Technol. 2000, 34, 2668-2674.
6. Lewis, D. L.; Garrison, A. W.; Wommack, K. E.; Whittemore, A.; Steudler, P.; Melillo, J. Influence of environmental changes on degradation of chiral pollutants in soils. Nature 1999, 401, 898-901.
7. Müller, T. A.; Kohler, H. P. E. Chirality of pollutants - effects on metabolism and fate. Apl. Microbiol. Biotechnol. 2004, 64, 300-316.
8. Fasel, R.; Parschau, M.; Ernst, K. H. Amplification of chirality in two-dimensional enantiomorphous lattices, Nature 2006, 439, 449-452.
9. Ali, I.; Aboul-Enein, H. Y.; Ghanem, A. Enantioselective toxicity and carcinogenesis. Curr. Pharm. Anal. 2005, 1, 109-125.
10. Garrison, A. W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 2006, 40, 16-23.
11. Lin, K. D.; Zhou, S. S.; Xu, C.; Liu, W. P. Enantiomeric resolution and biotoxicity of methamidophos. J. Agric. Food Chem. 2006, 54, 8134-8138.
12. Wang, L. M.; Liu, W. P.; Yang, C. X.; Pan, Z. Y.; Gan, J. Y.; Xu, C.; Zhao, M. R.; Schlenk, D. Enantioselectivity in estrogenic potential and uptake of bifenthrin. Environ. Sci. Technol. 2007, 41, 6124-6128.
13. Zhou, S. S.; Lin, K. D.; Yang, H. Y.; Li, L.; Liu, W. P.; Li, J. Stereoisomeric separation and toxicity of a new organophosphorus insecticide chloramidophos. Chem. Res. Toxicol. 2007, 20, 400-405.
14. Cai, X.; Liu, W. P.; Sheng, G. Y. Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures. J. Agric. Food Chem. 2008, 56, 2139-2146.
15. Su, S. Q. Chiral Compounds of herbicides. Modern Agrochem. 2005, 4, 1-5 (in Chinese).
16. Williams, A. Opportunities for chiral agrochemicals. Pestic. Sci. 1996, 46, 3-9.
17. Zhou, Y.: Li, L.; Lin, K. D.; Zhu, X. P.; Liu, W. P. Enantiomer separation of triazole fungicides by high-performance liquid chromatography. Chirality 2009, DOI: 10/1002/chir.20607.
18. Ourisson, G. The general role of terpenes and their global significance. Pure Appl. Chem. 1990, 62, 1401-1404.
19. Dregus, M.; Schmarr, H. G.; Takahisa, E.; Engel, K. H. Enantioselective analysis of methyl-branched alcohols and acids in rhubarb (Rheum rhabarbarum L.) stalks. J. Agric. Food Chem. 2003, 51, 7086-7091.
20. Sicilia, T.; Niemeyer, H. B.; Honig, D. M.; Metzler, M. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J. Agric. Food Chem. 2003, 51, 1181-1188.
21. Tamogami, S.; Awano, K.; Amaike, M.; Takagi, Y.; Kitahara, T. Analysis of enantiomeric ratios of aroma components in several flowers using a Chiramix column. Flavour Fragrance J. 2004, 19, 1-5.
22. Hui, F.: Ekbrog-Ott, K. H.; Armstrong, D. W. High-performance liquid chromatographic and capillary electrophoretic enantioseparation of plant growth regulators and related indole compounds using macrocyclic antibiotics as chiral selectors, J. Chromatogr., A 2001, 906, 91-103.
23. Armstrong, D. W.; Liu, Y. S.; He, L. F.; Ekborg-Ott, K. H.; Barnes, C. L.; Hammer, C. F. Potent enantioselective auxin: indole-3-succinic acid. J. Agric. Food Chem. 2002, 50, 437-476.
24. Kato, K.; Katayama, M.; Gautam, R. K.: Fujii, S.; Kimoto, H. Enzymatic preparation of both enantiomers of 4,4,4-trifluoro-3-(indole-3-)butyric acid, a novel plant growth regulator. J. Ferment. Bjoeng. 1993, 76, 178-183.
25. Katayama, M.; Kato, K.; Kimoto, H.; Fujii, S. (5)-(+)-4,4,4-Trifluoro-3- (indole-3-)butyric acid, a novel fluorinated plant growth regulator. Cell. Mol. Life Sci. 1995, 51, 721-724.
26. Lin, B. L.; Wang, H. J.: Wang. J. S.: Zaharia, L. I.; Abrams, S. R. Abscisic acid regulation of heterophylly in Marsilea quadrifolia L.: effects of R-(-) and S-(+) isomers. J. Exp. Bot. 2005, 56, 2935-2948.
27. Haughan, P. A.; Surden, R. S.; Lenton, J. R.: Goad, L. J. Inhibition of celery cell growth and sterol biosynthesis by the enantiomers of paclobutrazol. Phytochemistry 1989, 28, 781-787.
28. Lenton, J. R.; Appleford, N. E. J.; Temple-Smith, K. E. Growth retardant activity of paclobutrazol enantiomers in wheat seedlings. Plant Growth Regul. 1994, 15, 281-291.
29. Wong, C. S. Environmental fate processes and biochemical transformations of chiral emerging organic pollutants. Anal. Bioanal. Chem, 2006, 386, 544-558.
30. Schneiderheinze, J. M.; Armstrong, D. W.; Berthod, A. Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides. Chirality 1999, 11, 330-337.
31. Matell, M. Stereochemical studies on plant growth regulators. VII. Optically active a-(2-methyl-4-chlorophenoxy)-propionic acid and a-(2,4-dichlorophenoxy)-n-butyric acid and their steric relations. Ark. Kemi 1953, 6, 365-373.
32. Zhu. Y. H.: Wang, Z. R.; Li, B. Q. Handbook of Agrochemicals; China Three Gorges Publishing House: Beijing. China. 2006 (in Chinese).
33. Hoppe, H. H.; Zacher, H. Inhibition of fatty acid biosynthesis in isolated bean and maize chloroplasts by herbicidal phenoxy-phenoxypropionic acid derivatives and structurally related compounds. Pestic. Biochem. Physiol. 1985, 24, 298-305.
34. Rendina, A. R.; Felts, J. M.; Beaudoin, J. D.; Craigkennard, A. C.; Look, L. L.; Paraskos, S. L.; Hagenah, J. A. Kinetic characterization, stereoselectivity, and species selectivity of the inhibition of plant acetyl-CoA carboxylase by the aryloxyphenoxypropionic acid grass herbicides. Arch. Biochem. Biophys. 1988, 265, 219-225.
35. Shimabukuro, R. H.; Hoffer, B. L. Enantiomers of diclofop-methyl and their role in herbicide mechanism of action. Pestci. Biochem. Physiol. 1995, 51, 68-82.
36. Chesters, G.; Simsiman, G. V.; Levy, J.: Alhajjar, B. J.; Fsthulls, R. N.; Hsrkin, J. M. Environmental fate of alachlor and metolachlor. Rev. Environ. Contam. Toxicol. 1989, 110, 1-74.
37. Fischer, D. J.; Hayes, A. L. A comparison of the biochemical and physiological effects of the systemic fungicide cyprofuram with those of related compounds metalaxyl and metolachlor. Crop Prot. 1985, 4, 501-510.
38. http://pmep.cce.cornell.edu/profiles/herb-growthreg/fatty-alcohol- Monuron/s-metolachlor/S-metolachlor-0207.pdf.
39. http://www.freepatentsonline.com/EP1104990Bl.html?highlight= r, metalaxyl&stemming=on.
40. http://www.patentstorm.us/patents/7150877.html.
41. http://www.freepatentsonline.com/WO2000013505A2.html?highlight=r, metalaxyl&stemming=on.
42. Marucchini, C.; Zadra, C. Stereoselective degradation of metalaxyl and metalaxyl-M in soil and sunflower plants. Chirality 2002, 14, 32-38.
43. Zadra, C.; Marucchini, C.; Zazzerini, A. Behavior of metalaxyl and its pure R-enantiomer in sunflower paints (Helianthus annum). J. Agric. Food Chem. 2002, 50, 5373-5377.
44. Camilleri, P.; Gray, A.; Weaver, K.; Bowyer, J. R.; Williams, D. J. Herbicidal diphenyl ethers: stereochemical studies using enantiomers of a novel diphenyl ether phthalide. J. Agric. Food Chem. 1989, 37, 519-523.
45. Amine-Khodja, A.; Boulkamh, A.; Boule, P. Photochemical behaviour of phenylurea herbicides. Phptochem. Photobiol. Sci. 2004, 3, 145-156.
46. Omokawa, H.; Ryoo, J. H. Enantioselective response of rice and barnyard millet on root growth inhibition by optically active α-methylbenzyl phenylureas. Pestic. Biochem. Phys. 2001, 70, 1-6.
47. Omokawa, H.; Murata, H.; Kobayashi, S. Chiral response of Oryzeae and Paniceae plants in α-methylbenzyl-3-p-tolyl urea agar medium. Pest. Manag. Sci. 2003, 60, 59-64.
48. Omokawa, H.: Tabei, A. Enantioselective effects of optically active α-methybenzyl-s-trizine on the root growth of rice and echinochloa plants and their herbicidal activity. Biosci., Biotechnol, Biochem. 2002, 66, 1959-1962.
49. Müller, B. P.; Zumdick, A.; Schuphan. I.; Schmidt, B. Metabolism of the herbicide glufosinateammonium in plant cell cultures of transgenic (rhizomania-resistant) and non-transgenic sugarbeet (Beta vulgaris), carrot (Daucus carota), purple foxglove (Digitalis purpurea) and thorn apple (Datura stramonium). Pest Manag. Sci. 2001, 57, 46-56.
50. Ruhland, M.; Engelhardt, G.; Pawlizki, K. A comparative investigation of the metabolism of the herbicide glufosinate in cell cultures of transgenic glufosinate-resistant and non-transgenic oilseed rape (Brassica napus) and corn (Zea mays). Environ. Biosaf. Res. 2002, 1, 29-37.
51. Wang, P.; Jiang, S. R.; Qiu, J.; Wang, Q. X.; Wang, P.; Zhou, Z. Q. Stereoselective degradation of ethofumesate in turfgrass and soil. Pestic. Biochem. Physiol. 2005, 82, 197-204.
52. Lee, W. Y.; lannucci-Berger, W. A.; Eitzer, B. D.; White, J. C.; Mattina, M. I. Plant uptake and translocation of air-borne chlordaneand comparison with the soil-plant route. Chemosphere 2003, 53, 111-121.
53. White, J. C.; Mattina, M. J. I.; Eitzer, B. D.; lannucci-Berger, W. Tracking chlordane compositional and chiral profiles in soil and vegetation, Chemosphere 2002, 47, 639-646.
54. Mattina, M. I.; White, J.; Eitzer, B.; lannucci-Berger, W. Cycling of weathered chlordane residues in the environment: compositional and chiral profiles in contiguous soil, vegetation, and air compartments. Environ. Toxicol. Chem. 2002, 21, 281-288.
55. Garrison, A. W.; Nzengung, V. A.; Avants, J. K.; Ellington, J. J.; Jones, W. J.; Rennels, D.; Wolfe, N. L. Phytodegradation of p, p′-DDT and the enantiomers of o, p′-DDT. Environ. Sci. Technol. 2000, 34, 1663-1670.