Behavior of metalaxyl and its pure R-enantiomer in sunflower plants (Helianthus annus).
A possible stereospecific and/or stereoselective mechanism of biodegradation for metalaxyl and metalaxyl-M was studied to elucidate their behavior in sunflower plants and to compare their biodegradation. Greenhouse experiments were carried out to confirm the same efficacy of the two fungicides against infections by Plasmopara helianthi in sunflower plants. The two fungicides appear to have the same behavior regarding both the protection against plant infections and the mode of translocation and the rate and pathway of biotransformation, but we have evidence that this biotransformation process is enantioselective. Furthermore, we propose procedures for a chromatographic separation of enantiomers and acid metabolites of the fungicides and for the determination of the R:S ratio by HPLC chiral analyses. This study emphasizes the importance of examining the fate of both stereoisomers of a chiral agrochemical in an environmental system for the correct use of enantiomerically pure agrochemical compounds.
Dipartimento di Scienze Agroambientali e della Produzione Vegetale Chimica Agraria, Università degli Studi di Perugia, Borgo XX Giugno 72, 06121 Perugia, Italy.
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Zadra
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Marucchini
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Zazzerini
D000409:Alanine / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism* / Q000494:pharmacology; D001673:Biodegradation, Environmental; D005659:Fungicides, Industrial / Q000032:analysis / Q000378:metabolism* / Q000494:pharmacology; D006368:Helianthus / Q000378:metabolism* / Q000382:microbiology*; D010935:Plant Diseases / Q000382:microbiology; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D013172:Spores, Fungal / Q000502:physiology; D013237:Stereoisomerism
D005659:Fungicides, Industrial; C028175:metalaxyl; D000409:Alanine