手性酰胺类杀菌剂研究进展

doi:10.11924/j.issn.1000-6850.casb18120006

摘要/Abstract

摘要：

手性农药在生物体和环境中表现出环境行为、生物活性等方面的差异,采用传统的评价方式不能全面的评估手性农药对环境乃至人类的风险大小。酰胺类杀菌剂对由担子菌及立枯丝核菌等引起的植物病害具有良好的防治效果,然而部分含有手性中心原子的酰胺类杀菌剂会因为对映体表现出的差异,影响其安全性评价的准确性。为了全面开展手性酰胺类杀菌剂的立体选择性研究,本文归纳了手性酰胺类杀菌剂在对映体分离方法、选择性环境行为、选择性毒性与生物活性等方面的研究进展,对其科学使用具有指导性意义。

关键词: 手性酰胺类杀菌剂, 立体选择性, 环境行为, 毒性, 生物活性

Abstract:

Chiral pesticides exhibit differences in environmental behaviors and biological activities in organisms and environments. Traditional evaluation methods can not fully assess the risk of chiral pesticides to the environment and humans. Amide fungicides have good control effects on plant diseases caused by Basidiomycetes and Rhizoctonia solani. However, the accuracy of the risk evaluation could be affected by some amide fungicides enantiomers containing chiral central atoms. This paper summarizes the research progress of chiral amide fungicides in enantiomeric separation methods, stereoselective environmental behavior, stereoselective toxicity and biological activity, and could provide certain guidance for its scientific use.

Key words: chrial amidine fungicides, stereoselective, environmental behavior, toxicity, biological activity

中图分类号:

S482.2

段劲生, 沈杨, 王梅, 董旭, 孙明娜, 高同春. 手性酰胺类杀菌剂研究进展[J]. 中国农学通报, 2020, 36(9): 107-112.

Jinsheng Duan, Yang Shen, Mei Wang, Xu Dong, Mingna Sun, Tongchun Gao. Chiral Amidine Fungicides: Research Progress[J]. Chinese Agricultural Science Bulletin, 2020, 36(9): 107-112.

参考文献 57

[1]	林玉锁,龚瑞忠,朱忠林.农药与生态环境保护[M].北京:化学工业出版社,2001.
[2]	谢武明.持久性有机污染物(POPS)的环境问题与研究进展[J].中国环境监测,2004(2):58-61.
[3]	王慧芳,张颖,孙晓红.未来农药的发展趋势[J].天津化工,2005,19(4):13-16.
[4]	徐鹏. 手性农药在土壤动物虹叫体内的选择性富集代谢及毒性差异研究[D].北京:中国农业大学,2012.
[5]	胡耐冬,刘长令.新型三唑啉酮类除草剂唑酮草酯[J].精细与专用化学品,2003,11(14):21-24.
[6]	张松柏. 光合细菌降解拟除虫菊酯类农药残留物研究[D].长沙:中南大学,2010.
[7]	于金刚. 色谱法拆分几种手性药物的研究[D].长沙:中南大学,2005.
[8]	庞丽. 几种手性药物的高效液相色谱法拆分及大鼠体内药动学研究[D].郑州:郑州大学,2014.
[9]	Kallenborn R, Oehme M, Vetter W.et al.Enantiomer selective separation of toxaphene congeners isolated from seal blubber and obtained by synjournal[J]. Chemosphere,1994,28(1):89-98.
[10]	Poiger T, Muller M D, Buser H R, et al.Environmental behavior of the chiral herbicide haloxyfop.1.Rapid and preferential interconversion of the enantiomers in soil[J]. J Agric Food Chem,2015,63(10):2583-2590.
[11]	陈秀. 呋虫胺对映体对蜜蜂选择毒性及其在黄瓜和土壤中降解行为[D].北京:中国农业科学院,2013.
[12]	李晶. 三唑类手性杀菌剂苯醚甲环唑的立体选择性生物活性与环境行为研究[D].北京:中国农业科学院,2012.
[13]	Waldeck,B.Biological significance of the enantiomeric purity of drugs[J]. Chirality,1993,5(5), 350-355.
[14]	Kallenborn R, Oehme M, Vetter W, et al.Enantiomer selective separation of toxaphene congeners isolated from seal blubber and obtained by synjournal[J]. Chemosphere,1994,28(1): 89-98.
[15]	王晓光,段青,栾兴社.生物催化在手性化合物合成中的应用[J].化工科技,2007(01):71-75.
[16]	刘维屏,叶璟,张安平,等. 植物与手性化合物的对映体选择性相互作用[J].应用生态学报,2008(02):441-448.
[17]	刘维屏,徐超,周珊珊.手性污染物与环境安全[J].环境化学,2006(03):247-251.
[18]	蒋木庚,王鸣华,杨春龙,等. 新型旋光性农药的研究与展望[J].农药,2000(12):1-3.
[19]	Harner T, Wiberg K.Wiberg, et al. Enantiomer fractions are preferred to enantiomer ratios for describing chiral signatures in environmental analysis[J]. Environmental Science and Technology,2000, 34(1):218-220.
[20]	梁娴,王慧文.手性拆分剂及其手性药物色谱拆分技术的应用进展[J].安徽医药,2013(01):147-149.
[21]	刘维屏,张颖.手性农药毒性评价进展[J].浙江大学学报:农业与生命科学版,2012(01):63-70.
[22]	吴再坤,钟宏,王微宏,等. 手性药物的活性分析与生物转化[J].化工技术与开发,2006(09):24-27.
[23]	孙智慧,贾顺姬,孟安明. 斑马鱼: 在生命科学中畅游[J].生命科学,2006(05):431-436.
[24]	杨丽萍,王徐,钱高.纤维素类手性固定相高效液相色谱法拆分三唑类手性化合物[J].分析测试学报,2004(05):25-28.
[25]	谢显传,张少华,王冬生,等. 露地和大棚条件下阿维菌素在蔬菜作物上的残留消解动态比较[J].中国农业科学,2008(10):3399-3404.
[26]	邓朱波,胡继业.农用杀菌剂腈菌唑光学对映体的生物活性[J].农药,2011(05):371-373.
[27]	邹苏琪,殷梧,杨昱鹏,等. 斑马鱼行为学实验在神经科学中的应用[J].生物化学与生物物理进展,2009(01):5-12.
[28]	梁娴,王慧文.手性拆分剂及其手性药物色谱拆分技术的应用进展[J].安徽医药,2013(01):147-149.
[29]	夏爽,袁圆,潘桂湘,等. 超临界流体色谱在手性药物拆分中的应用进展[J].中国实验方剂学杂志,201521(12):217-220.
[30]	田芹,任丽萍,吕春光,等.反相色谱条件下三唑类手性农药对映异构体的拆分[J].分析化学,2010,38(5):688-692.
[31]	Wang P, Jiang S R, Qiu J, et al.Stereoselective degradation of ethofumesate in turfgrass and soil[J]. Pesticide Biochemistry and Physiology, 2005,82(3):197-204.
[32]	Gübitz G, Schmid M G.Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography[J]. Electrophoresis, 1997, 792(1-2):179-225.
[33]	Okamoto M.Reversal of elution order during the chiral separation in high performance liquid chromatography[J]. Journal of pharmaceutical and biomedical analysis, 2002,27(3):401-407.
[34]	Li X C, Ferreira D, Ding Y.Determination of absolute configuration of natural products: theoretical calculation of electronic circular dichroism as a tool[J]. Current organic chemistry, 2010, 14(16):1678-1697.
[35]	Nugroho A E, Morita H.Circular dichroism calculation for natural products[J]. Journal of natural medicines, 2014, 68(1):1-10.
[36]	Li Y, Dong F, Liu X.Development of a multi-residue enantiomeric analysis method for 9 pesticides in soil and water by chiral liquid chromatography/tandem mass spectrometry[J]. Journal of Hazardous Materials, 2013, 9(18):250-251.
[37]	朱美娜,李朝阳,李巧玲,等.土壤中甲氰菊酯对映体选择性降解的研究[J].江苏农业科学,2011,39(06):481-483.
[38]	任国宾,詹予忠,郭士岭.手性拆分技术进展[J].河南化工,2002(01):1-3.
[39]	王一帆. 奎宁及Salen型高效液相色谱手性固定相研究[D].昆明:云南师范大学,2014.
[40]	Scriba G K E. Chiral recognition in separation science: an overview[J]. Chiral Separations: Methods and Protocols, 2013: 1-27.
[41]	王美云. 手性农药甲霜灵的立体选择性降解研究[D].南京:南京农业大学,2014.
[42]	Zhang H, Wang X Q, Jin L X, et al.Enantioselective determination of acylamino acid fungicides in vegetables and fruits by chiral liquid chromatography coupled with tandem mass spectrometry[J]. Journal of Separation Science,2012,35(15).
[43]	邱静.酰胺类手性农药在动物体内的立体选择性行为[D].北京:中国农业大学.
[44]	王鹏,刘东晖,王玉红,等. 高效液相色谱法拆分苯霜灵对映体[J].分析化学,2006(11):1524-1528.
[45]	Wang P, Jiang S R, Qiu J, et al.Stereoselective degradation of ethofumesate in turfgrass and soil[J]. Pesticide Biochemistry and Physiology, 2005, 82(3): 197-204.
[46]	Liu D H, Wang P, Zhou W F, et al.Direct chiral resolution and its application to the determination of fungicide benalaxyl in soil and water by high-performance liquid chromatography[J]. Analytica Chimica Acta, 2005, 555(2).
[47]	Buser H R, Mueller M D.Environmental behavior of acetamide pesticide stereoisomers. 1.Stereo-and enantioselective determination using chiral high-resolution gas chromatography and chiral HPLC[J]. Environ Sci Technol, 1995, 29(8): 2023-2030.
[48]	Buser H R, Mueller M D.Enantioselective determination of chlordane components, metabolites, and photoconversion products in environmental samples using chiral high-resolution gas chromatography and mass spectrometry[J]. Environmental Science & Technology, 1993,26(8):325-30.
[49]	王美云. 手性农药甲霜灵的立体选择性降解研究[D].南京:南京农业大学,2014.
[50]	方松,岳珩,孙惠青,等.手性甲霜灵在烟草不同部位叶片中的立体选择性行为[J].农药,2018,57(01):20-22,33.
[51]	张平. 几种农药在动物模型中立体选择性降解及代谢组学研究[D].北京:中国农业大学,2016.
[52]	刘明珂. 苯霜灵对映体在水生环境中的代谢行为[D].北京:中国农业大学,2015.
[53]	谢海燕. 手性杀菌剂吡噻菌胺在土壤中选择性降解研究[D].呼和浩特:内蒙古大学,2017.
[54]	Hegeman W J, Laane R W.Enantiomeric enrichment of chiral pesticides in the environment[J]. Reviews of Environmental Contamination and Toxicology,2001,173(2): 85.
[55]	王新茹. 两种酰胺类手性农药在动物体内及体外的代谢及毒性研究[D].北京:中国农业大学,2016.
[56]	刘萍. 手性杀菌剂甲霜灵在土壤中的吸附和对绿藻水生毒理的对映体差异[D].大连:大连理工大学,2009.
[57]	王喆. 农药甲霜灵、精甲霜灵与重金属镉对蚯蚓毒性的研究[D].武汉:华中科技大学,2009.