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Stereoselective Separation of the Fungicide Bitertanol Stereoisomers by High-Performance Liquid Chromatography and Their Degradation in Cucumber
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-11-29 00:00:00 , DOI: 10.1021/acs.jafc.8b04594 Lianshan Li 1 , Beibei Gao 1 , Zhaoxian Zhang 1 , Mailun Yang 1 , Xin Li 1 , Zongzhe He 1 , Minghua Wang 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-11-29 00:00:00 , DOI: 10.1021/acs.jafc.8b04594 Lianshan Li 1 , Beibei Gao 1 , Zhaoxian Zhang 1 , Mailun Yang 1 , Xin Li 1 , Zongzhe He 1 , Minghua Wang 1
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Bitertanol is a widely used triazole fungicide and consists of four stereoisomers. A new high-performance liquid chromatography (HPLC) method was developed for simultaneous analysis of the four stereoisomers in apple, pear, tomato, cucumber, and soil. The mechanism of separation was explained with molecular docking and effects of thermodynamic parameters on the resolution. The absolute configuration and optical rotation of four stereoisomers were confirmed by X-ray diffraction and HPLC tandem circular dichroism, respectively. A good linearity (R2 ≥ 0.999) was obtained for four stereoisomers in all matrix-matched calibration curves in the range of 0.02–10 mg/L. The mean recoveries of four stereoisomers in five matrices ranged from 74.6% to 101.0% with an intraday and interday relative standard deviation from 0.6% to 9.9%. Stereoselective degradation of bitertanol in cucumber was observed: (1R,2S)-bitertanol and (1R,2R)-bitertanol were preferentially degraded with enantiomeric fraction values from 0.5 to 0.43 at 7 d and 0.42 at 5 d, respectively. This research provides a useful tool for the analysis of bitertanol stereoisomers.
中文翻译：
高效液相色谱法选择性分离杀真菌剂叔丁醇立体异构体及其在黄瓜中的降解
Bitertanol是一种广泛使用的三唑类杀菌剂，由四种立体异构体组成。开发了一种新的高效液相色谱（HPLC）方法，用于同时分析苹果，梨，番茄，黄瓜和土壤中的四种立体异构体。通过分子对接和热力学参数对分离度的影响解释了分离的机理。四种立体异构体的绝对构型和旋光性分别通过X射线衍射和HPLC串联圆二色性确定。良好的线性度（R 2在0.02–10 mg / L范围内的所有与基质匹配的校准曲线中，获得了四种立体异构体的≥0.999）。五种基质中四种立体异构体的平均回收率范围为74.6％至101.0％，日内和日间相对标准偏差为0.6％至9.9％。观察到黄瓜中苦味子醇的立体选择性降解：（1 R，2 S）-苦味子醇和（1 R，2 R）-苦味子醇被优先降解，对映体分数值分别在7 d和0.5 d从0.5降低到0.43和0.42。这项研究为分析苦参醇立体异构体提供了有用的工具。
更新日期：2018-11-29
中文翻译：
高效液相色谱法选择性分离杀真菌剂叔丁醇立体异构体及其在黄瓜中的降解
Bitertanol是一种广泛使用的三唑类杀菌剂，由四种立体异构体组成。开发了一种新的高效液相色谱（HPLC）方法，用于同时分析苹果，梨，番茄，黄瓜和土壤中的四种立体异构体。通过分子对接和热力学参数对分离度的影响解释了分离的机理。四种立体异构体的绝对构型和旋光性分别通过X射线衍射和HPLC串联圆二色性确定。良好的线性度（R 2在0.02–10 mg / L范围内的所有与基质匹配的校准曲线中，获得了四种立体异构体的≥0.999）。五种基质中四种立体异构体的平均回收率范围为74.6％至101.0％，日内和日间相对标准偏差为0.6％至9.9％。观察到黄瓜中苦味子醇的立体选择性降解：（1 R，2 S）-苦味子醇和（1 R，2 R）-苦味子醇被优先降解，对映体分数值分别在7 d和0.5 d从0.5降低到0.43和0.42。这项研究为分析苦参醇立体异构体提供了有用的工具。
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