Enantioselectivity in the phytotoxicity of herbicide imazethapyr

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 4, 2009, Pages 1624-1631

  Zhou, Qingyan ^a   Xu, Chao ^b   Zhang, Yongsong ^a   Liu, Weiping ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Border cell; Cell organelle; Enantioselectivity; Root hair; Statocytes

Indexed keywords

HERBICIDE; IMAZETHAPYR; NICOTINIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG EFFECT; MAIZE; PLANT ROOT; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; ULTRASTRUCTURE;

HERBICIDES; NICOTINIC ACIDS; PLANT ROOTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; ZEA MAYS;

ZEA MAYS;

EID: 64549152953     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf803673e     Document Type: Article

References (35)

1. Williams, A. Opportunities for chiral pesticides. Pestic. Sci. 1996, 46, 3-9.
2. Lin, K. D.; Liu, W. P.; Li, L.; Gan, J. Y. Single and joint acute toxicity of isocarbophos enantiomers to Daphnia magna. J. Agric. Food Chem. 2008, 56, 4273-4277.
3. Kurihara, N.; Miyamoto, J.; Paulson, G. D.; Zeeh, B.; Skidmore, M. W.; Hollingworth, R. M.; Kuiper, H. A. Chirality in synthetic agrochemicals: bioactivity and safety consideration. Pure Appl. Chem. 1997, 69, 1335-1348.
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, 701-706.
5. Ali, I.; Gupta, V. K.; Aboul-Enein, H. Y. Chirality: a challenge for the environmental scientists. Curr. Sci. 2003, 84, 152-156.
6. Garrison, A. W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 2006, 40, 16-23.
7. Buser, H. P.; Francotte, E. Chiral Separations; American Chemical Society: Washington, DC, 1997.
8. 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.
9. Tan, S.; Evans, R.; Singh, B. Herbicidal inhibitors of amino acid biosynthesis and herbicide tolerant crops. Amino Acids 2006, 30, 195-204.
10. Los, M. (5-Oxo-2-imidazolin-2-yl) -arylcarboxylates: A New Class of Herbicides. In Pesticide Synthesis Through Rational Approaches; Magee, P. S., Kohn, G K., Menn, J. J., Eds. American Chemical Society: Washington, DC, 1984; pp 29-44.
11. Shaner, D. L.; Singh, B. K. Acetohydroxyacid Synthase Inhibitors. In Herbicide ActiVity: Toxicology, Biochemistry and Molecular Biology; Roe, R. M., Burton, J. D., Kuhr, R. J., Eds. IOS Press: Amsterdam, The Netherlands, 1997; pp 69-110.
12. Shaner, D. L.; Anderson, P. C.; Stidham, M. A. Imidazolinones-potent inhibiters of acetohydroxyacid synthase. Plant physiol. 1984, 76, 545-546.
13. Shaner, D. L.; Reider, M. L. Physiological response of corn to AC 243, 997 in combination with valine and leucine. Pestic. Biochem. Physiol. 1986, 25, 248-257.
14. Schloss, J. V.; Ciskanik, L. M.; Van Dyk, D. E. Origin of the herbicide binding site of acetolactate synthase. Nature 1988, 331, 360-362.
15. McCourt, J. A.; Pang, S. S.; King-Scott, J.; Guddat, L. W.; Duggleby, R. G. Herbicide-binding sites revealed in the structure of plant acetohydroxyacid synthase. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 569-573.
16. Zhou, Q. Y.; Liu, W. P.; Zhang, Y. S.; Liu, K. K. Action mechanisms of acetolactate synthase-inhibiting herbicides. Pestic. Biochem. Physiol. 2007, 89, 89-96.
17. Lin, K. D.; Xu, C.; Zhou, S. S.; Liu, W. P.; Gan, J. Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography. Chirality 2007, 19, 171-178.
18. Jenkins, A. L.; Hedgepeth, W. A. Analysis of chiral pharmaceuticals using HPLC with CD detection. Chirality 2005, 17, 24-29.
19. Halgren, T. A. Merck molecular force field 0.1. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
20. Fayez, K. A.; Kristen, U. The influence of herbicides on the growth and proline content of primary roots and on the ultrastructure of root caps. Environ Exp. Bot. 1996, 36, 71-81.
21. Grichar, W. J.; Ocumpaugh, W. R. Bundleflower (Desmanthus bicornutus) response to postemergence herbicides. Weed Technol. 2007, 21, 1089-1092.
22. Soltani, N.; Gillard, C. L.; Swanton, C. J.; Shropshire, C.; Sikkema, P. H. Response of white bean (Phaseolus Vulgaris) to imazethapyr. Crop Prot. 2008, 27, 672-677.
23. Soltani, N.; Robinson, E..; Shropshire, C.; Sikkema, P. H. Otebobean (Phaseolus Vulgaris) sensitivity to pre-emergence herbicides. Crop Prot. 2006, 25, 476-479.
24. Hirano, Y.; Hijii, N. Effects of low pH and aluminum on root morphology of Japanese red cedar saplings. Environ. Pollut. 1998, 101, 339-347.
25. Hund, A.; Fracheboud, Y.; Soldati, A.; Stamp, P. Cold tolerance of maize seedlings as determined by root morphology and photosynthetic traits. Eur. J. Agron. 2008, 28, 178-185.
26. Kopittke, P. A.; Dart, P. J.; Menzies, N. W. Toxic effects of low concentrations of Cu on nodulation of cowpea (Vigna unguiculata). Environ. Pollut. 2007, 145, 309-315.
27. Merkl, N.; Schultze-Kraft, R.; Infante, C. Phytoremediation in the tropics: influence of heavy crude oil on root morphological characteristics of graminoids. Environ. Pollut. 2005, 138, 86-91.
28. Sheldon, A. R.; Menzies, N. W. The effect of copper toxicity on the growth and root morphology of Rhodes grass (Chloris gayana Knuth.) in resin buffered solution culture. Plant Soil 2005, 278, 341-349.
29. Subramanyan, J.; Rangaswamy, N. S. Effects of dichlobenil on two tip growth systems: pollen tube and root hair. Natl. Acad. Sci. Lett. (India) 1999, 22, 113-118.
30. Ferrara, G.; Loffredo, E.; Senesi, N. Phytotoxic, clastogenic and bioaccumulation effects of the environmental endocrine disruptor bisphenol A in various crops grown hydroponically. Planta 2006, 223, 910-916.
31. Hawes, M. C.; Gunawardena, U.; Miyasaka, S.; Zhao, X. The role of root border cells in plant defense. Trends Plant Sci. 2000, 5, 128-133.
32. Miasaka, S. C.; Hawes, M. C. Possible role of root border cells in detection and avoidance of aluminium toxicity. Plant Physiol. 2001, 125, 1978-1987.
33. Pan, J. W.; Ye, D.; Wang, L. L.; Hua, J.; Zhao, G. F.; Pan, W. H. Root border cell development is a temperature insensitive and Al-sensitive process in barley. Plant Cell Physiol. 2004, 45, 751-760.
34. Zhu, M.; Ahn, S. M.; Atsumoto, H. Inhibition of growth and development of root border cells in wheat by Al. Physiol. Plant. 2003, 117, 359-367.
35. Ma, Z.; Bielenberg, D. G.; Brown, K. M.; Lynch, J. P. Regulation of root hair density by phosphorus availability in Arabidopsis thaliana. Plant Cell Environ. 2001, 24, 459-467.