Four Propiconazole Stereoisomers: Stereoselective Bioactivity, Separation via Liquid Chromatography-Tandem Mass Spectrometry, and Dissipation in Banana Leaves
Four Propiconazole Stereoisomers: Stereoselective Bioactivity, Separation via Liquid Chromatography-Tandem Mass Spectrometry, and Dissipation in Banana Leaves
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四种丙环唑立体异构体：立体选择性生物活性、通过液相色谱-串联质谱法分离以及香蕉叶中的消散。
DOI：
10.1021/acs.jafc.1c06253
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发表时间：
2022-01-14
影响因子：
6.1
通讯作者：
Zhang, Yuping
中科院分区：
文献类型：
--
作者：
Tang, Shouying;Meng, Xiurou;Zhang, Yuping
在这项研究中，我们评估的立体选择性生物活性的丙环唑立体异构体对香蕉叶斑病的病原体（新月弯孢菌和香蕉炭疽菌）。我们还评估了立体异构体的立体选择性降解香蕉叶在田间试验条件下。Superchiral S-OX色谱柱成功地分离了丙环唑的4种立体异构体。X-射线单晶衍射证实，丙环唑的顺式立体异构体-（+）-A的绝对构型为（2 R，4S）-丙环唑，丙环唑的顺式立体异构体-（-）-A的绝对构型为（2S，4 R）-丙环唑。体外抑菌试验结果表明，（2 R，4S）-（+）-丙环唑对两种目标植物真菌的抑菌活性最高。建立了香蕉叶中丙环唑4种立体异构体残留的高效液相色谱-串联质谱分析方法。立体异构体的平均回收率为76.3%~ 103%，相对标准偏差为1.25%~ 11.4%。4种丙环唑立体异构体在香蕉叶中的检出限为0.002-0.006 mg/kg，定量限为0.02-0.03 mg/kg。丙环唑-（-）-B和丙环唑-（-）-A在3个典型香蕉产区香蕉叶片中的降解略快于其相应的对映体丙环唑-（+）-B和丙环唑-（+）-A。
In this study, we evaluated the stereoselective bioactivity of four propiconazole stereoisomers against the causal agents of the banana leaf spot disease (Curvularia lunata and Colletotrichum musae). We also evaluated the stereoselective degradation of the stereoisomers in banana leaves under field test conditions. The Superchiral S-OX column successfully separated the four propiconazole stereoisomers. X-ray single-crystal diffraction confirmed that the absolute configuration of the cis-stereoisomer-(+)-A of propiconazole was (2R,4S)-propiconazole and that of the cis-stereoisomer-(-)-A of propiconazole was (2S,4R)-propiconazole. In vitro antibacterial results revealed that (2R,4S)-(+)-propiconazole had the highest activity against the two target plant fungi. In this study, a new and efficient high-performance liquid chromatography tandem mass spectrometry method was developed for the determination of the four stereoisomeric residues of propiconazole in banana leaves. The mean recoveries of the method for the stereoisomers were 76.3-103% with relative standard deviations of 1.25-11.4%. The four propiconazole stereoisomers had a detection limit of 0.002-0.006 mg/kg and a limit of quantification of 0.02-0.03 mg/kg in banana leaves. Propiconazole-(-)-B and propiconazole-(-)-A degraded slightly faster than their corresponding enantiomers propiconazole-(+)-B and propiconazole-(+)-A in banana leaves collected from three typical banana production areas.