Absolute Configuration, Enantioselective Bioactivity, and Degradation of the Novel Chiral Triazole Fungicide Mefentrifluconazole,Journal of Agricultural and Food Chemistry

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Absolute Configuration, Enantioselective Bioactivity, and Degradation of the Novel Chiral Triazole Fungicide Mefentrifluconazole
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2021-04-20 , DOI: 10.1021/acs.jafc.0c07947
Lianshan Li ₁ , Xiaofang Sun ₁ , Xuejun Zhao ₁ , Yudie Xiong ₁ , Beibei Gao ₁ , Jing Zhang ₁ , Haiyan Shi ₁ , Minghua Wang ₁

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Mefentrifluconazole is a new chiral triazole fungicide with a pair of enantiomers. However, the enantioselective differences in the biological effects and environmental behaviors of mefentrifluconazole are unclear. In the present work, a new simultaneous determination method of mefentrifluconazole enantiomers was established using ultrahigh-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). The absolute configuration of the two mefentrifluconazole enantiomers was confirmed by comparing the experimental and calculated ECD spectra. The enantioselective bioactivity to target fungi and degradation in cucumber samples were also assessed. The absolute configurations of the two enantiomers eluted on the Superchiral IG-3 column were confirmed as R-(−)-mefentrifluconazole and S-(+)-mefentrifluconazole. The R-(−)-mefentrifluconazole possessed 5–473 times higher bioactivity than S-(+)-mefentrifluconazole toward six kinds of target pathogenic fungi. In addition, R-(−)-mefentrifluconazole exhibited stronger efficacy of suppression of ergosterol biosynthesis. The molecular docking results indicated that R-(−)-mefentrifluconazole had shorter binding distances and lower energies with the target protein than S-(+)-mefentrifluconazole, which may result in the enantioselective bioactivity. The high-efficiency enantiomer of R-(−)-mefentrifluconazole has longer duration in cucumber samples due to the relatively long half-life of 4.0 days. This research has clarified the bioactivity differences and mechanism between mefentrifluconazole enantiomers against target fungi and laid the foundation for an in-depth study of mefentrifluconazole at the chiral level.

中文翻译：

新型手性三唑杀菌剂甲灭氟康唑的绝对构型，对映选择性生物活性和降解

Mefentrifluconazole是一种新的手性三唑类杀菌剂，带有一对对映异构体。但是，尚不清楚甲芬氟康唑的生物学效应和环境行为的对映选择性差异。在本工作中，采用超高效液相色谱-串联质谱法（UPLC-MS / MS）建立了一种新的同时测定甲芬三氟康唑对映体的方法。通过比较实验和计算出的ECD谱图，可以确认这两种美芬三氟康唑对映体的绝对构型。还评估了对目标真菌的对映选择性生物活性和黄瓜样品的降解。在Superchiral IG-3色谱柱上洗脱的两种对映异构体的绝对构型被确认为R -（-）-甲芬三氟康唑和S-（+）-甲芬氟康唑。在六种目标病原真菌方面，R -（-）-甲芬三氟康唑的生物活性是S -（+）-甲芬三氟康唑的5–473倍。另外，R -（-）-甲芬三氟康唑显示出更强的抑制麦角固醇生物合成的功效。分子对接结果表明，R -（-）-美芬三氟康唑比S -（+）-美芬三氟康唑具有更短的结合距离和更低的与目标蛋白的能量，这可能导致对映选择性的生物活性。R的高效对映体-（-）-美芬三氟康唑在黄瓜样品中的持续时间较长，因为其相对较长的半衰期为4.0天。这项研究阐明了美芬三氟康唑对映体之间针对靶标真菌的生物活性差异和机理，为深入研究手性水平上的美芬三氟康唑奠定了基础。

更新日期：2021-05-05

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