The chiral triazole fungicide difenoconazole: Absolute stereochemistry, stereoselective bioactivity, aquatic toxicity and environmental behavior in vegetables and soil

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Environmental Science and Technology, 47, 3386-3394 (DOI: 10.1021/es304982m), © 2013 American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work, see http://pubs.acs.org/articlesonrequest/AOR IWGxaR52k8sQFKnfMzcZ
This Manuscript version is made available under the CC-BY-NC-ND 4.0 license.
https://creativecommons.org/licenses/by-nc-nd/4.0/

ABSTRACT

In this study, the systemic assessments of the stereoisomers of triazole fungicide difenoconazole are reported for the first time, including absolute stereochemistry, stereoselective bioactivity toward pathogens (Alternaria sonali, Fulvia fulva, Botrytis cinerea, and Rhizoctonia solani), and toxicity toward aquatic organisms (Scenedesmus obliquus, Daphnia magna, and Danio rerio). Moreover, the stereoselective degradation of difenoconazole in vegetables (cucumber, Cucumis sativus and tomato, Lycopersicon esculentum) under field conditions and in soil under laboratory-controlled conditions (aerobic and anaerobic) was investigated. There were 1.33–24.2-fold and 1.04–6.78-fold differences in bioactivity and toxicity, respectively. Investigations on the stereoselective degradation of difenoconazole in vegetables showed that the highest-toxic and lowest-bioactive (2S,4S)-stereoisomer displays a different enrichment behavior in different plant species. Under aerobic or anaerobic conditions, (2R,4R)- and (2R,4S)-difenoconazole were preferentially degraded in the soil. Moreover, difenoconazole was configurationally stable in the test soil matrices. On the basis of biological activity, ecotoxicity, and environmental behavior, it is likely that the use of pure (2R,4S)-difenoconazole instead of the commercial stereoisomer mix may help to increase the bioactivity and reduce environmental pollution.