顺硝烯新烟碱杀虫剂的同位素标记合成、手性分离鉴定及土壤中的归趋研究
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摘要
哌虫啶和环氧虫啶是具有显著活性的顺硝烯新烟碱类化合物,具有良好的市场前景。目前,哌虫啶因对抗性褐飞虱的高活性,已获得临时登记,由华东理工大学和江苏克胜联合开发。环氧虫啶也因其对抗性褐飞虱和白粉虱的高效性,由华东理工大学、上海生农生化及美国富美实公司的三方合作进行商品化开发。为了进一步研究哌虫啶和环氧虫啶的作用靶标、作用机理、代谢过程、环境行为与归趋、安全性评价和使用技术等,本文研究了其放射性及稳定同位素的标记合成,为借助同位素示踪与波谱、质谱及现代分子生物学等相关技术,深入、系统进行上述研究提供先决条件。
(1)结合放射性同位素原料供应和合成方法,设计了三条中间体6-Cl-PMNI的微量或半微量合成路线,分别以硼氢化钠、硝基甲烷、乙二胺盐酸盐为起始原料。化合物6-Cl-PMNI与巴豆醛成环、正丙醇醚化得到产物哌虫啶,或直接与丁二醛环合得到环氧虫啶。对微量合成路线进行了优化,提高起始原料的利用率,并最终应用于放射性及稳定同位素的合成,得到4个放射性标记化合物和4个稳定同位素标记化合物。放射性化合物经核磁和质谱结构鉴定,化学和放化纯度分析,确定比活度；稳定同位素的引入也得到同位素核磁确认。
(2)通过手性制备HPLC对哌虫啶和环氧虫啶的异构体进行拆分,分离得到目标光学纯异构体,手性HPLC分析其光学纯度大于99%。异构体经1H NMR、13C NMR和2D HSQC和HMBC对其进行碳氢归属,确证哌虫啶和环氧虫啶化学结构；通过2DNOESY分析其空间构型,推测对映(差向)异构体之间的构型差异性。获得哌虫啶4个异构体和环氧虫啶2个异构体的单晶,确认异构体之间的空间构型差异性。最后,通过研究各异构体在有机溶剂、磷酸盐缓冲液和CaCl2水溶液中的稳定性,模拟哌虫啶和环氧虫啶异构体在手性分析、农药剂型和土壤中代谢过程中的手性变化,以寻找较稳定的分析和处理手性化合物的溶剂环境。
(3)研究14C标记的环氧虫啶及其异构体在淹水胁迫条件下在土壤中的归趋,比较其在不同土壤中可提态残留(ER)、结合态残留(BR)和矿化的差异。结果表明：100天培养结束,ER在三种土壤中均呈现减小趋势,三种土中BR随时间显著增加,矿化累积量也不断增加,但不同土壤间差异显著,与部分理化性质呈线性相关。BR和矿化在灭菌和非灭菌条件差异显著,消旋体和2个异构体之间的ER、BR和矿化没有明显的差异。这些结果有助于推进环氧虫啶的环境风险评估和商业化进程。
Paichongding and Cycloxaprid are two novel cis-neonicotinoids with good industrialisation prospects for their high activities. Due to higher activity against imidacloprid-resistant brown planthopper (nilaparvata lugens), paichongding was jointly developed by East China University of Science and Technology (ECUST) and Jiangsu Kwin Company. Cycloxaprid has high activities against imidacloprid-resistant brown planthopper and whitefly (besimia tebaci), it has already obtained joint efforts from ECUST, Shanghai Shengnong Pesticide Co. Ltd and FMC Corporation. To improve the studies of modes of action, metabolism environment behavior, safety evolution and application, radio and stable isotopic synthesis of paichongding and cycloxaprid were studied, which will facilitate future research combined with isotopic tracer, high-resolution spectroscopy instrument, molecular biology and other related technologies. The contents were as follows:
1) Semi-/micro-syntheses of6-Cl-PMNI were performed using three commercial radio or stable isotope labeled starting materials, NaBH4, nitromethane and ethylenediamine dihydrochloride, respectively. Cyclization of6-C1-PMNI with crotonaldehyde followed by etherification with propanol, or reaction with succinaldehyde affords paichongding or cycloxaprid, respectively. Four radio or stable isotope labeled compounds were obtained under the optimizing reaction condition. Chemical and radiochemical purities and special activities of radiolabeled compound were determined by HPLC or HPLC-LSC. All labeled compounds were characterized by1H,13C NMR or MS.
2) Isomers of paichongding or cycloxaprid were separated by chiral HPLC with optical purities over99%. Chemical structures of these chiral isomers were characterized by1H,13C NMR,2D HSQC and HMBC. Configuration differences in four isomers of paichongding and two isomers of cycloxaprid were analyzed by2D NOESY, and finally determined by crystal structures. Then, chiral stability of the isomers in organic solvents, buffer solutions or soil water was explored, to stimulate the process of enantiomers analysis, pesticide formulation or soil metabolism research, and find suitable solvents for analysis and sample treatment.
3)14C labeled cycloxaprid and its isomers were used to understand the transformation of cycloxaprid in flooded soils, and their differences in extractable residues (ER), bound residues (BR) and mineralization were compared. After100d incubation, ER for14C labels followed a similar dissipation trend, BR increased obviously with time, and mineralization to CO2also increased cumulatively. All these changed were depended closely on the soil type and showed correlation coefficients with properties of the soils. No significant difference in ER, BR and mineralization were observed between two isomers and racemates. All these findings would promote the process of environment risk assessment and commercialization.
(1)结合放射性同位素原料供应和合成方法,设计了三条中间体6-Cl-PMNI的微量或半微量合成路线,分别以硼氢化钠、硝基甲烷、乙二胺盐酸盐为起始原料。化合物6-Cl-PMNI与巴豆醛成环、正丙醇醚化得到产物哌虫啶,或直接与丁二醛环合得到环氧虫啶。对微量合成路线进行了优化,提高起始原料的利用率,并最终应用于放射性及稳定同位素的合成,得到4个放射性标记化合物和4个稳定同位素标记化合物。放射性化合物经核磁和质谱结构鉴定,化学和放化纯度分析,确定比活度；稳定同位素的引入也得到同位素核磁确认。
(2)通过手性制备HPLC对哌虫啶和环氧虫啶的异构体进行拆分,分离得到目标光学纯异构体,手性HPLC分析其光学纯度大于99%。异构体经1H NMR、13C NMR和2D HSQC和HMBC对其进行碳氢归属,确证哌虫啶和环氧虫啶化学结构；通过2DNOESY分析其空间构型,推测对映(差向)异构体之间的构型差异性。获得哌虫啶4个异构体和环氧虫啶2个异构体的单晶,确认异构体之间的空间构型差异性。最后,通过研究各异构体在有机溶剂、磷酸盐缓冲液和CaCl2水溶液中的稳定性,模拟哌虫啶和环氧虫啶异构体在手性分析、农药剂型和土壤中代谢过程中的手性变化,以寻找较稳定的分析和处理手性化合物的溶剂环境。
(3)研究14C标记的环氧虫啶及其异构体在淹水胁迫条件下在土壤中的归趋,比较其在不同土壤中可提态残留(ER)、结合态残留(BR)和矿化的差异。结果表明：100天培养结束,ER在三种土壤中均呈现减小趋势,三种土中BR随时间显著增加,矿化累积量也不断增加,但不同土壤间差异显著,与部分理化性质呈线性相关。BR和矿化在灭菌和非灭菌条件差异显著,消旋体和2个异构体之间的ER、BR和矿化没有明显的差异。这些结果有助于推进环氧虫啶的环境风险评估和商业化进程。
Paichongding and Cycloxaprid are two novel cis-neonicotinoids with good industrialisation prospects for their high activities. Due to higher activity against imidacloprid-resistant brown planthopper (nilaparvata lugens), paichongding was jointly developed by East China University of Science and Technology (ECUST) and Jiangsu Kwin Company. Cycloxaprid has high activities against imidacloprid-resistant brown planthopper and whitefly (besimia tebaci), it has already obtained joint efforts from ECUST, Shanghai Shengnong Pesticide Co. Ltd and FMC Corporation. To improve the studies of modes of action, metabolism environment behavior, safety evolution and application, radio and stable isotopic synthesis of paichongding and cycloxaprid were studied, which will facilitate future research combined with isotopic tracer, high-resolution spectroscopy instrument, molecular biology and other related technologies. The contents were as follows:
1) Semi-/micro-syntheses of6-Cl-PMNI were performed using three commercial radio or stable isotope labeled starting materials, NaBH4, nitromethane and ethylenediamine dihydrochloride, respectively. Cyclization of6-C1-PMNI with crotonaldehyde followed by etherification with propanol, or reaction with succinaldehyde affords paichongding or cycloxaprid, respectively. Four radio or stable isotope labeled compounds were obtained under the optimizing reaction condition. Chemical and radiochemical purities and special activities of radiolabeled compound were determined by HPLC or HPLC-LSC. All labeled compounds were characterized by1H,13C NMR or MS.
2) Isomers of paichongding or cycloxaprid were separated by chiral HPLC with optical purities over99%. Chemical structures of these chiral isomers were characterized by1H,13C NMR,2D HSQC and HMBC. Configuration differences in four isomers of paichongding and two isomers of cycloxaprid were analyzed by2D NOESY, and finally determined by crystal structures. Then, chiral stability of the isomers in organic solvents, buffer solutions or soil water was explored, to stimulate the process of enantiomers analysis, pesticide formulation or soil metabolism research, and find suitable solvents for analysis and sample treatment.
3)14C labeled cycloxaprid and its isomers were used to understand the transformation of cycloxaprid in flooded soils, and their differences in extractable residues (ER), bound residues (BR) and mineralization were compared. After100d incubation, ER for14C labels followed a similar dissipation trend, BR increased obviously with time, and mineralization to CO2also increased cumulatively. All these changed were depended closely on the soil type and showed correlation coefficients with properties of the soils. No significant difference in ER, BR and mineralization were observed between two isomers and racemates. All these findings would promote the process of environment risk assessment and commercialization.
引文
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