异菌脲在油菜植株、土壤和水中的代谢途径及代谢物3,5-DCA的毒性研究
Studies on Metabolic Pathways of Iprodione in Rape Plant, Soil, and Water and Toxicity of Metabolite 3,5-DCA
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摘要: 为了明确异菌脲在作物和环境中的代谢及代谢产物3，5-二氯苯胺（3，5-DCA）的生态风险，通过水培试验、土壤孵育和水解试验，采用UPLC-TOF-MS/MS，鉴定了异菌脲在油菜植株、土壤和水中的代谢产物，推测了代谢途径，并研究了3，5-DCA对细胞和蚯蚓的毒性。在油菜植株中检测到4种异菌脲代谢产物（M1、M3、M6和M7），在土壤中发现了5种代谢产物（M1、M3、M6、M7和M8），在水中发现了7种代谢产物（M1、M2、M4、M5、M7、M8和M9）。根据代谢产物的化学结构，明确了异菌脲的代谢主要通过酰胺键的断裂及脱烷基化反应，并推测了异菌脲在油菜植株、土壤和水中的代谢途径。代谢产物3，5-DCA对Hep G2的细胞毒性（IC50为99.7 mg·L-1）是异菌脲（IC50为304.8 mg·L-1）的3.1倍，对赤子爱胜蚓的14 d急性毒性（LC50为31.56 mg·kg-1）是母体的15倍以上（LC50>500 mg·kg-1），表明异菌脲的代谢为增毒代谢。研究结果对异菌脲的环境安全性评价具有重要的意义。Abstract: In order to clarify the metabolisms of iprodione in crop and environment and the ecological risk of metabolite 3,5-dichloroaniline (3,5-DCA), the metabolites of iprodione in rape plant, soil and water were identified by UPLC-TOF-MS/MS through the hydroponic experiment, soil incubation and hydrolytic experiment, and the metabolic pathways were speculated. In addition, the toxicity of 3,5-DCA was studied. Four metabolites (M1, M3, M6 and M7) were found in rape plants, five metabolites (M1, M3, M6, M7 and M8) were found in the soil, and seven metabolites (M1, M2, M4, M5, M7, M8 and M9) were found in water. According to the chemical structure of the metabolites, we found that iprodione are mainly metabolized by the cleavage of amide bond and dealkylation reaction, while the metabolic pathways of iprodione in rape plant, soil and water were speculated. The cytotoxicity of metabolite 3,5-DCA (IC50 was 99.7 mg·L-1) to Hep G2 was 3.1 times higher than that of iprodione (IC50 was 304.8 mg·L-1), and the 14 d acute toxicity of 3,5-DCA (LC50 was 31.56 mg·kg-1) to earthworm was more than 15 times greater than that of the parent (LC50>500 mg·kg-1), which indicated that the metabolic process of the iprodione was toxicity-increased metabolism. The results are of great significance for the environmental safety evaluation of iprodione.
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Key words:
- iprodione /
- metabolite /
- cytotoxicity /
- acute toxicity against earthworms /
- metabolic pathways
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刘琨, 李勇, 王蓉, 等. 我国人参产区灰霉病菌抗药性研究初报[J]. 植物保护, 2020, 46(2):196-198 , 208 Liu K, Li Y, Wang R, et al. Preliminary report of the resistance of Botrytis cinerea isolates from ginseng producing area to four fungicides in China[J]. Plant Protection, 2020, 46(2):196-198, 208(in Chinese)
Dutra P S S, Pereira W V, De Mio L L M. Brazilian isolates of Monilinia fructicola from peach do not present reduced sensitivity to iprodione[J]. European Journal of Plant Pathology, 2019, 153(4):1341-1346 Molaei H, Abrinbana M, Ghosta Y. Baseline sensitivities to azoxystrobin and tebuconazole in Sclerotinia sclerotiorum isolates from sunflower in Iran related to sensitivities to carbendazim and iprodione[J]. Journal of Phytopathology, 2020, 168(6):353-362 Kim E, Lee H M, Kim Y H. Morphogenetic alterations of Alternaria alternata exposed to dicarboximide fungicide, iprodione[J]. The Plant Pathology Journal, 2017, 33(1):95-100 汪汉成, 张敏, 张之矾, 等. 多菌灵等5种杀菌剂对烟草立枯病菌的生物活性[J]. 农药学学报, 2017, 19(5):569-575 Wang H C, Zhang M, Zhang Z F, et al. Bioactivities of carbendazim, etc. five fungicides against Rhizoctonia solani in tobacco[J]. Chinese Journal of Pesticide Science, 2017, 19(5):569-575(in Chinese)
Kiss A, Virág D. Photostability and photodegradation pathways of distinctive pesticides[J]. Journal of Environmental Quality, 2009, 38(1):157-163 Zhang Z X, Du G Z, Gao B B, et al. Stereoselective endocrine-disrupting effects of the chiral triazole fungicide prothioconazole and its chiral metabolite[J]. Environmental Pollution, 2019, 251:30-36 Gao J, Wang F, Cui J N, et al. Assessment of toxicity and environmental behavior of chiral ethiprole and its metabolites using zebrafish model[J]. Journal of Hazardous Materials, 2021, 414:125492 Liu H, Yi X T, Bi J W, et al. The enantioselective environmental behavior and toxicological effects of pyriproxyfen in soil[J]. Journal of Hazardous Materials, 2019, 365:97-106 宋晓. 氟虫腈及其代谢物的细胞毒性研究[D]. 北京:中国农业科学院, 2019:6-7 Song X. Research on the cytotoxicity of fipronil and its metabolites[D]. Beijing:Chinese Academy of Agricultural Sciences, 2019:6 -7(in Chinese)
Li H X, Zhong Q, Wang X R, et al. The degradation and metabolism of chlorfluazuron and flonicamid in tea:A risk assessment from tea garden to cup[J]. The Science of the Total Environment, 2021, 754:142070 张嘉坤, 武宪, 周旭东, 等. 二甲四氯异辛酯及其代谢物二甲四氯在玉米中的残留量及风险评估[J]. 食品安全质量检测学报, 2020, 11(20):7544-7554 Zhang J K, Wu X, Zhou X D, et al. Residue and risk assessment of 2-methyl-4-chlorophenoxyacetic acid-isooctyl and its metabolite 2-methyl-4-chlorophenoxyacetic acid in corn[J]. Journal of Food Safety & Quality, 2020, 11(20):7544-7554(in Chinese)
Schwack W, Bourgeois B, Walker F. Fungicides and photochemistry photodegradation of the dicarboximide fungicide iprodione[J]. Chemosphere, 1995, 31(4):2993-3000 Ambrus, Buys M, Miyamoto J, et al. IUPAC reports on pesticides, No. 28:Some aspects of the analysis of residues of dicarboximide fungicides in food[J]. Pure and Applied Chemistry, 1991, 63(5):747-762 Rifai A, Souissi Y, Genty C, et al. Ultraviolet degradation of procymidone:Structural characterization by gas chromatography coupled with mass spectrometry and potential toxicity of photoproducts using in silico tests[J]. Rapid Communications in Mass Spectrometry:RCM, 2013, 27(13):1505-1516 United States Environmental Protection Agency (US EPA). Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Procymidone[S]. Washington DC:Office of Prevention, Pesticides and Toxic Substances, 2005 Dom N, Knapen D, Benoot D, et al. Aquatic multi-species acute toxicity of (chlorinated) anilines:Experimental versus predicted data[J]. Chemosphere, 2010, 81(2):177-186 Lai Q, Sun X F, Li L S, et al. Toxicity effects of procymidone, iprodione and their metabolite of 3,5-dichloroaniline to zebrafish[J]. Chemosphere, 2021, 272:129577 农业农村部农药检定所. 农药残留物手册[M]. 北京:中国农业出版社, 2018:216 柳嘉怡, 卜宪娜. 霍格兰(Hoagland)溶液对小麦种苗生长的影响[J]. 现代农业科技, 2020(1):9-10 Liu J Y, Bu X N. Effect of Hoagland solution on growth of wheat seedlings[J]. Modern Agricultural Science and Technology, 2020 (1):9-10(in Chinese)
Yang Q Q, Shan W Y, Hu L G, et al. Uptake and transformation of silver nanoparticles and ions by rice plants revealed by dual stable isotope tracing[J]. Environmental Science & Technology, 2019, 53(2):625-633 高玉莲, 李睿光, 常静, 等. 油菜对3种作物种子萌发和幼苗生长的化感作用[J]. 应用生态学报, 2020, 31(12):4153-4160 Gao Y L, Li R G, Chang J, et al. Allelopathy of rape on seed germination and seedling growth of three crops[J]. Chinese Journal of Applied Ecology, 2020, 31(12):4153-4160(in Chinese)
李如男, 董丰收, 吴小虎, 等. 酶介导下农药在植物中的三相代谢转化研究进展[J]. 农药学学报, 2019, 21(S1):799-814 Li R N, Dong F S, Wu X H, et al. Research progress in three-phase metabolic transformations of pesticides in plants mediated by enzymes[J]. Chinese Journal of Pesticide Science, 2019, 21(S1):799-814(in Chinese)
Morant M, Bak S, Møller B L, et al. Plant cytochromes P450:Tools for pharmacology, plant protection and phytoremediation[J]. Current Opinion in Biotechnology, 2003, 14(2):151-162 Ter Halle A, Drncova D, Richard C. Phototransformation of the herbicide sulcotrione on maize cuticular wax[J]. Environmental Science & Technology, 2006, 40(9):2989-2995 Liu X M, Xu X, Li B H, et al. Genomic and transcriptomic insights into cytochrome P450 monooxygenase genes involved in nicosulfuron tolerance in maize (Zea mays L.)[J]. Journal of Integrative Agriculture, 2018, 17(8):1790-1799 Huang M T, Lu Y C, Zhang S, et al. Rice (Oryza sativa) laccases involved in modification and detoxification of herbicides atrazine and isoproturon residues in plants[J]. Journal of Agricultural and Food Chemistry, 2016, 64(33):6397-6406 Athiel P, Alfizar, Mercadier C, et al. Degradation of iprodione by a soil Arthrobacter-like strain[J]. Applied and Environmental Microbiology, 1995, 61(9):3216-3220 Mercadier C, Garcia D, Vega D, et al. Metabolism of iprodione in adapted and non-adapted soils; Effect of soil inoculation with an iprodione-degrading Arthrobacter strain[J]. Soil Biology and Biochemistry, 1996, 28(12):1791-1796 Campos M, Karas P S, Perruchon C, et al. Novel insights into the metabolic pathway of iprodione by soil bacteria[J]. Environmental Science and Pollution Research International, 2017, 24(1):152-163 Lee J B, Sohn H Y, Shin K S, et al. Microbial biodegradation and toxicity of vinclozolin and its toxic metabolite 3,5-dichloroaniline[J]. Journal of Microbiology and Biotechnology, 2008, 18(2):343-349 -
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