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Stereoselective degradation of metalaxyl and metalaxyl‐M in soil and sunflower plants
Author(s) -
Marucchini C.,
Zadra C.
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10032
Subject(s) - metalaxyl , chemistry , enantiomer , enantioselective synthesis , sunflower , degradation (telecommunications) , chromatography , chirality (physics) , racemization , fungicide , pesticide , organic chemistry , botany , horticulture , agronomy , telecommunications , chiral symmetry breaking , physics , quantum mechanics , computer science , nambu–jona lasinio model , biology , quark , catalysis
A high proportion of agrochemicals are chiral compounds. Since stereoisomers often show different biological and physiological properties, the biological and metabolic responses to these compounds and their fate in the environment are expected to be different. In this work we investigate a possible stereo and/or enantioselective degradation in soil and plants (sunflower) of the fungicide Metalaxyl ( rac ‐Metalaxyl) and the new compound Metalaxyl‐M ((−)‐( R )‐Metalaxyl) and propose procedures for extraction, cleanup, chromatographic separation of enantiomers, and determination of the R : S ratio by using an HPLC chiral column. The degradation of the two stereoisomers of Metalaxyl proved to be enantioselective and dependent on the media: the (+)‐( S )‐enantiomer showed a faster degradation in plants, while the (−)‐( R )‐enantiomer showed a faster degradation in soil. In this study there was no evidence that racemization of Metalaxyl‐M took place either in soil or in sunflowers. Chirality 14:32–38, 2002. © 2002 Wiley‐Liss, Inc.