新型手性杀虫剂Fluralaner的对映选择性检测，生物活性和代谢。,Journal of Agricultural and Food Chemistry

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新型手性杀虫剂Fluralaner的对映选择性检测，生物活性和代谢。
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-04-23 , DOI: 10.1021/acs.jafc.9b07907
Zhaoxian Zhang ₁ , Liangliang Zhou ₁ , Yingying Gao ₁ , Jing Zhang ₁ , Beibei Gao ₁ , Haiyan Shi ₁ , Minghua Wang ₁

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兽药Fluralaner是潜在的手性异恶唑啉杀虫剂，具有很高的杀虫和杀螨活性。然而，关于氟尿烷的对映选择性作用的信息很少。在这项工作中，通过液相色谱-质谱法在农产品和动物器官中建立了一种有前途的手性检测方法，以研究对映选择性代谢和生物活性。用S -（+）-氟尿烷和R -（-）-氟尿烷证实了氟尿烷对映体的旋光性和绝对构型。生物活性测定表明小号-fluralaner是33-39倍，比更积极ř对-对映体二化螟和灰飞虱。这一发现表明，在农业管理中使用纯S-氟尿烷代替外消旋体可以降低风险。同源性建模和分子对接表明，具有-6.90 kcal / mol较低能量的S -fluralaner对γ-氨基丁酸受体具有更好的结合亲和力。探索了大鼠肝微粒体中的立体选择性代谢，并用优先代谢的R-氟尿烷观察到轻微的对映选择性。对映体分数值在0.43至0.49的范围内。研究结果可为残留检测，风险评估以及在农业应用中氟烷的科学使用提供参考。

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Enantioselective Detection, Bioactivity, and Metabolism of the Novel Chiral Insecticide Fluralaner.

Fluralaner, a veterinary drug, is a potential chiral isoxazoline insecticide possessing high insecticidal and acaricidal activity. However, there is little information regarding the enantioselective effect of fluralaner. In this work, a promising chiral detection method was established with liquid chromatography–mass spectrometry in agricultural products and animal organs to investigate enantioselective metabolism and bioactivity. The optical rotation and absolute configuration of fluralaner enantiomers were confirmed with S-(+)-fluralaner and R-(−)-fluralaner. The bioactivity assay indicated that S-fluralaner was 33–39 times more active than the R-enantiomer against Chilo suppressalis and Laodelphax striatellus. This finding suggests that the application of pure S-fluralaner instead of racemate in agricultural management could reduce risk. Homology modeling and molecular docking showed that S-fluralaner, with a lower energy of −6.90 kcal/mol, possessed better binding affinity to the γ-aminobutyric acid receptor. The stereoselective metabolism in rat liver microsomes was explored, and slight enantioselectivity was observed with R-fluralaner that was preferentially metabolized. The enantiomer fraction values ranged from 0.43 to 0.49. The results provide reference for residue detection, risk assessment, and the scientific use of fluralaner in agricultural applications.

更新日期：2020-06-24

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