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Chiral triazole fungicide difenoconazole: absolute stereochemistry, stereoselective bioactivity, aquatic toxicity, and environmental behavior in vegetables and soil.
Environmental Science & Technology ( IF 10.8 ) Pub Date : 2013 Apr 2 , DOI: 10.1021/es304982m
Fengshou Dong 1 , Jing Li 1 , Bezhan Chankvetadze 2 , Yongpu Cheng 1, 3 , Jun Xu 1 , Xingang Liu 1 , Yuanbo Li 1 , Xiu Chen 1 , Carlo Bertucci 4 , Daniele Tedesco 4 , Riccardo Zanasi 5 , Yongquan Zheng 1
Affiliation  

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.

中文翻译:

手性三唑类杀真菌剂苯氟康唑:在蔬菜和土壤中的绝对立体化学,立体选择性生物活性,水生毒性和环境行为。

在这项研究中,首次报道了对三唑类杀菌剂苯芬康唑的立体异构体的系统评估,包括绝对立体化学,对病原体(Alternaria sonali,富尔弗富弗尔瓦,灰葡萄孢和灰霉菌)的立体选择性生物活性,以及​​对水生生物的毒性(斜角场景,水蚤(Daphnia magna)和里约热内卢(Danio rerio)。此外,还研究了田间条件下和实验室控制条件下(需氧和厌氧)条件下蔬菜(黄瓜,黄瓜,番茄,番茄)中苯二酚的立体选择性降解。生物活性和毒性分别有1.33-24.2倍和1.04-6.78倍的差异。对蔬菜中的芬尼康唑的立体选择性降解的研究表明,毒性最高,生物活性最低的(2S,4S)-立体异构体在不同植物物种中表现出不同的富集行为。在有氧或厌氧条件下,(2R,4R)-和(2R,4S)-二苯并康唑在土壤中优先降解。此外,在试验土壤基质中二苯并康唑的构型是稳定的。基于生物活性,生态毒性和环境行为,很可能使用纯的(2R,4S)-二苯并康唑代替商业的立体异构体混合物可以帮助提高生物活性并减少环境污染。在土壤中优先降解4S)-二苯并康唑。此外,在试验土壤基质中二苯并康唑的构型是稳定的。基于生物活性,生态毒性和环境行为,很可能使用纯的(2R,4S)-二苯并康唑代替商业的立体异构体混合物可以帮助提高生物活性并减少环境污染。在土壤中优先降解4S)-二苯并康唑。此外,在试验土壤基质中二苯并康唑的构型是稳定的。基于生物活性,生态毒性和环境行为,很可能使用纯的(2R,4S)-二苯并康唑代替商业的立体异构体混合物可以帮助提高生物活性并减少环境污染。
更新日期:2017-01-31
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