新烟碱杀虫剂环氧虫啶对苜蓿蚜的毒力及其在苜蓿蚜和水稻中的降解转化
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摘要
为明确顺硝烯新烟碱杀虫剂环氧虫啶对苜蓿蚜Aphis craccivora Koch的毒力及其在苜蓿蚜体内和水稻中的降解转化趋势,采用带虫浸液法测定环氧虫啶及其降解产物NTN23692对苜蓿蚜的毒力,并采用超高效液相色谱检测法研究苜蓿蚜体内不同酶对环氧虫啶降解转化的影响以及环氧虫啶在水稻中降解转化为NTN23692的情况。结果表明:环氧虫啶及其降解产物NTN32692对苜蓿蚜的LC_(50)分别为3.45 mg/L和0.79 mg/L,NTN32692的毒力明显高于环氧虫啶。与对照组相比,在添加酶抑制剂的条件下,苜蓿蚜谷胱甘肽S-转移酶孵育液中环氧虫啶和NTN32692的浓度均显著降低,羧酸酯酶和细胞色素P450酶孵育液中环氧虫啶和NTN32692的浓度变化不显著。用不同浓度环氧虫啶处理水稻24 h后,叶片中环氧虫啶和NTN32692的累积量随着浓度提高均显著增加;在水稻中的残留动态表明,培养7 d后,叶片中环氧虫啶和NTN32692的浓度皆显著降低,降幅分别达到67.33%和89.42%。
To figure out the insecticidal activity of cycloxaprid against groundnut aphid Aphis craccivora Koch, the leaf-dip method was performed to test the acute toxicity of cycloxaprid and NTN32692 on A. craccivora, and ultraperformance liquid chromatography(UPLC) method was adopted to study the hydrolysis of cycloxaprid into NTN32692 in A. craccivora and rice plants. The LC_(50) value of cycloxaprid against A. craccivora was 3.45 mg/L, which was lower than that of NTN32692(0.79 mg/L). With glutathione S-transferase inhibitor treatment, the concentration of cycloxaprid and NTN32692 in A.craccivora enzymatic incubation solution was obviously less than that in the control. However, the concentrations of cycloxaprid and NTN32692 were not significantly different in A. craccivora enzymatic incubation solution with carboxylesterase inhibitor and with/without NADPH in cytochrome P450 monooxygenase. The accumulation of cycloxaprid and NTN32692 increased significantly in rice leaves with different cycloxaprid dosage treatments in 24 h. Cycloxaprid and NTN32692 were both found to be degraded in rice plants within seven days. The contents of cycloxaprid and NTN32692 in rice plants were decreased significantly, up to 67.33% and 89.42%, respectively.
To figure out the insecticidal activity of cycloxaprid against groundnut aphid Aphis craccivora Koch, the leaf-dip method was performed to test the acute toxicity of cycloxaprid and NTN32692 on A. craccivora, and ultraperformance liquid chromatography(UPLC) method was adopted to study the hydrolysis of cycloxaprid into NTN32692 in A. craccivora and rice plants. The LC_(50) value of cycloxaprid against A. craccivora was 3.45 mg/L, which was lower than that of NTN32692(0.79 mg/L). With glutathione S-transferase inhibitor treatment, the concentration of cycloxaprid and NTN32692 in A.craccivora enzymatic incubation solution was obviously less than that in the control. However, the concentrations of cycloxaprid and NTN32692 were not significantly different in A. craccivora enzymatic incubation solution with carboxylesterase inhibitor and with/without NADPH in cytochrome P450 monooxygenase. The accumulation of cycloxaprid and NTN32692 increased significantly in rice leaves with different cycloxaprid dosage treatments in 24 h. Cycloxaprid and NTN32692 were both found to be degraded in rice plants within seven days. The contents of cycloxaprid and NTN32692 in rice plants were decreased significantly, up to 67.33% and 89.42%, respectively.
引文
Bass C,Denholm I,Williamson MS,Nauen R.2015.The global status of insect resistance to neonicotinoid insecticides.Pesticide Biochemistry and Physiology,121:78-87
Bass C,Puinean AM,Zimmer CT,Denholm L,Field LM,Foster SP,Gutbrod O,Nauen R,Slater R,Williamson MS.2014.The evolution of insecticide resistance in the peach potato aphid,Myzus persicae.Insect Biochemistry and Molecular Biology,51:41-51
Bradford MM.1976.A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.Analytical Biochemistry,72(1/2):248-254
Bredeson MM,Reese RN,Lundgren JG.2015.The effects of insecticide dose and herbivore density on tri-trophic effects of thiamethoxam in a system involving wheat,aphids,and ladybeetles.Crop Protection,69:70-76
Cui L,Sun LN,Shao XS,Cao YZ,Yang DB,Li Z,Yuan HZ.2010.Systemic action of novel neonicotinoid insecticide IPP-10 and its effect on the feeding behaviour of Rhopalosiphum padi on wheat.Pest Management Science,66(7):779-785
Cui L,Sun LN,Yan DB,Yan XJ,Yuan HZ.2012.Effects of cycloxaprid,a novel cis-nitromethylene neonicotinoid insecticide,on the feeding behaviour of Sitobion avenae.Pest Management Science,68(11):1484-1491
Ford KA,Casida JE.2008.Comparative metabolism and pharmacokinetics of seven neonicotinoid insecticides in spinach.Journal of Agricultural and Food Chemistry,56(21):10168-10175
Gao ZS,Zhang XF,Liu HT,Zhang WJ,Mu W.2016.Feasibility for controlling wheat aphids by seed dressing with neonicotinoid insecticides.Journal of Plant Protection,43(5):864-872(in Chinese)[高志山,张学峰,刘海涛,张文娟,慕卫.2016.新烟碱类杀虫剂种子包衣防治麦蚜的可行性评价.植物保护学报,43(5):864-872]
Li C,Xu XY,Li JY,Ye QF,Li Z.2011.Radiosynthesis of tritium-labeled novel nitromethylene neonicotinoids compounds with NaB3H4.Journal of Labelled Compounds&Radiopharmaceuticals,54(5):256-259
Liu XQ,Xu XY,Li C,Zhang HX,Fu QG,Shao XS,Ye QF,Li Z.2015a.Degradation of chiral neonicotinoid insecticide cycloxaprid in flooded and anoxic soil.Chemosphere,119:334-341
Liu XQ,Xu XY,Li C,Zhang HX,Fu QG,Shao XS,Ye QF,Li Z.2016.Assessment of the environmental fate of cycloxaprid in flooded and anaerobic soils by radioisotopic tracing.Science of the Total Environment,543:116-122
Liu XQ,Xu XY,Zhang HX,Li C,Shao XS,Ye QF,Li Z.2015b.Bioavailability and release of nonextractable(bound)residues of chiral cycloxaprid using geophagous earthworm Metaphire guillelmi in rice paddy soil.Science of the Total Environment,526:243-250
Mao DR.1994.Research methods of plant nutrition.Beijing:China Agricultural University Press,pp.16(in Chinese)[毛达如.1994.植物营养研究方法.北京:中国农业大学出版社,pp.16]
Nauen R,Ebbinghaus-Kintscher U,Salgado VL,Kaussmann M.2003.Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants.Pesticide Biochemistry and Physiology,76(2):55-69
Prabhaker N,Castle S,Henneberry TJ,Toscano NC.2005.Assessment of cross-resistance potential to neonicotinoid insecticides in Bemisia tabaci(Hemiptera:Aleyrodidae).Bulletin of Entomological Research,95(6):535-543
Simon-Delso N,Amaral-Rogers V,Belzunces LP,Bonmatin JM,Chagnon M,Downs C,Furlan L,Gibbons DW,Giorio C,Girolami V,et al.2015.Systemic insecticides(neonicotinoids and fipronil):trends,uses,mode of action and metabolites.Environmental Science and Pollution Research,22(1):5-34
Shao XS,Fu H,Xu XY,Xu XL,Liu ZW,Li Z,Qian XH.2009.Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid:design,synthesis,crystal structure,and insecticidal activities.Journal of Agricultural and Food Chemistry,58(5):2696-2702
Shao XS,Liu ZW,Xu XY,Li Z,Qian XH.2013a.Overall status of neonicotinoid insecticides in China:production,application and innovation.Journal of Pesticide Science,38(1):1-9
Shao XS,Swenson TL,Casida JE.2013c.Cycloxaprid insecticide:nicotinic acetylcholine receptor binding site and metabolism.Journal of Agricultural and Food Chemistry,61(33):7883-7888
Shao XS,Xia SS,Durkin KA,Casida JE.2013b.Insect nicotinic receptor interactions in vivo with neonicotinoid,organophosphorus,and methylcarbamate insecticides and a synergist.Proceedings of the National Academy of Sciences of the United States of America,110(43):17273-17277
Tomizawa M,Casida JE.2003.Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors.Annual Review of Entomology,48(1):339-364
Wu YC,Xu ZP,Shao XS,Cheng JG,Li Z.2016.Toxicity of cycloxaprid to Aphis craccivora(Koch)and its effects on detoxification enzymes.Chinese Journal of Pesticide Science,18(6):710-716(in Chinese)[吴勇超,须志平,邵旭升,程家高,李忠.2016.环氧虫啶对苜蓿蚜的毒力及对其体内解毒酶活性的影响.农药学学报,18(6):710-716]
Xu HX,Zheng XS,Tian JC,Lai FX,He JC,LüZX.2017.Advances in the development and application of control technologies for insect pest management in paddy fields in China.Journal of Plant Protection,44(6):925-939(in Chinese)[徐红星,郑许松,田俊策,赖凤香,何家春,吕仲贤.2017.我国水稻害虫绿色防控技术的研究进展与应用现状.植物保护学报,44(6):925-939]
Zhang J,Cao YQ,Cui L,Qin ZH,Ma YQ,Rui CH.2015.Toxicity of N′-nitrohydrazinecarboximidamides to several aphids and the influence on the activities of related enzymes in Aphis gossypii.Chinese Journal of Pesticide Science,17(2):143-148(in Chinese)[张靖,曹亚琴,崔丽,覃兆海,马永强,芮昌辉.2015.N′-硝基缩氨基胍类化合物对蚜虫的室内毒力测定及相关酶活性的影响.农药学学报,17(2):143-148]
Zhang J,Fu Q,Wang H,Li J,Wang W,Yang Z,Ye Q,Li C,Li Z.2013.Enantioselective uptake and translocation of a novel chiral neonicotinoid insecticide cycloxaprid in youdonger(Brassica campestris subsp.chinensis).Chirality,25(11):686-691
Zhang YB,Qian H.2015.The global marketing and development of six classes of insecticides and new insecticides.Agrochemicals Today,(5):26-32(in Chinese)[张一宾,钱虹.2015.世界六大类杀虫剂的发展和新研发的杀虫剂品种.今日农药,(5):26-32]
Zhuang YY.2014.Study on the hydrolysis and the photodegradation of cycloxaprid in water.Master Thesis.Shanghai:East China University of Science and Technology(in Chinese)[庄英滢.2014.环氧虫啶水解及光解稳定性研究.硕士学位论文.上海:华东理工大学]
Bass C,Puinean AM,Zimmer CT,Denholm L,Field LM,Foster SP,Gutbrod O,Nauen R,Slater R,Williamson MS.2014.The evolution of insecticide resistance in the peach potato aphid,Myzus persicae.Insect Biochemistry and Molecular Biology,51:41-51
Bradford MM.1976.A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.Analytical Biochemistry,72(1/2):248-254
Bredeson MM,Reese RN,Lundgren JG.2015.The effects of insecticide dose and herbivore density on tri-trophic effects of thiamethoxam in a system involving wheat,aphids,and ladybeetles.Crop Protection,69:70-76
Cui L,Sun LN,Shao XS,Cao YZ,Yang DB,Li Z,Yuan HZ.2010.Systemic action of novel neonicotinoid insecticide IPP-10 and its effect on the feeding behaviour of Rhopalosiphum padi on wheat.Pest Management Science,66(7):779-785
Cui L,Sun LN,Yan DB,Yan XJ,Yuan HZ.2012.Effects of cycloxaprid,a novel cis-nitromethylene neonicotinoid insecticide,on the feeding behaviour of Sitobion avenae.Pest Management Science,68(11):1484-1491
Ford KA,Casida JE.2008.Comparative metabolism and pharmacokinetics of seven neonicotinoid insecticides in spinach.Journal of Agricultural and Food Chemistry,56(21):10168-10175
Gao ZS,Zhang XF,Liu HT,Zhang WJ,Mu W.2016.Feasibility for controlling wheat aphids by seed dressing with neonicotinoid insecticides.Journal of Plant Protection,43(5):864-872(in Chinese)[高志山,张学峰,刘海涛,张文娟,慕卫.2016.新烟碱类杀虫剂种子包衣防治麦蚜的可行性评价.植物保护学报,43(5):864-872]
Li C,Xu XY,Li JY,Ye QF,Li Z.2011.Radiosynthesis of tritium-labeled novel nitromethylene neonicotinoids compounds with NaB3H4.Journal of Labelled Compounds&Radiopharmaceuticals,54(5):256-259
Liu XQ,Xu XY,Li C,Zhang HX,Fu QG,Shao XS,Ye QF,Li Z.2015a.Degradation of chiral neonicotinoid insecticide cycloxaprid in flooded and anoxic soil.Chemosphere,119:334-341
Liu XQ,Xu XY,Li C,Zhang HX,Fu QG,Shao XS,Ye QF,Li Z.2016.Assessment of the environmental fate of cycloxaprid in flooded and anaerobic soils by radioisotopic tracing.Science of the Total Environment,543:116-122
Liu XQ,Xu XY,Zhang HX,Li C,Shao XS,Ye QF,Li Z.2015b.Bioavailability and release of nonextractable(bound)residues of chiral cycloxaprid using geophagous earthworm Metaphire guillelmi in rice paddy soil.Science of the Total Environment,526:243-250
Mao DR.1994.Research methods of plant nutrition.Beijing:China Agricultural University Press,pp.16(in Chinese)[毛达如.1994.植物营养研究方法.北京:中国农业大学出版社,pp.16]
Nauen R,Ebbinghaus-Kintscher U,Salgado VL,Kaussmann M.2003.Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants.Pesticide Biochemistry and Physiology,76(2):55-69
Prabhaker N,Castle S,Henneberry TJ,Toscano NC.2005.Assessment of cross-resistance potential to neonicotinoid insecticides in Bemisia tabaci(Hemiptera:Aleyrodidae).Bulletin of Entomological Research,95(6):535-543
Simon-Delso N,Amaral-Rogers V,Belzunces LP,Bonmatin JM,Chagnon M,Downs C,Furlan L,Gibbons DW,Giorio C,Girolami V,et al.2015.Systemic insecticides(neonicotinoids and fipronil):trends,uses,mode of action and metabolites.Environmental Science and Pollution Research,22(1):5-34
Shao XS,Fu H,Xu XY,Xu XL,Liu ZW,Li Z,Qian XH.2009.Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid:design,synthesis,crystal structure,and insecticidal activities.Journal of Agricultural and Food Chemistry,58(5):2696-2702
Shao XS,Liu ZW,Xu XY,Li Z,Qian XH.2013a.Overall status of neonicotinoid insecticides in China:production,application and innovation.Journal of Pesticide Science,38(1):1-9
Shao XS,Swenson TL,Casida JE.2013c.Cycloxaprid insecticide:nicotinic acetylcholine receptor binding site and metabolism.Journal of Agricultural and Food Chemistry,61(33):7883-7888
Shao XS,Xia SS,Durkin KA,Casida JE.2013b.Insect nicotinic receptor interactions in vivo with neonicotinoid,organophosphorus,and methylcarbamate insecticides and a synergist.Proceedings of the National Academy of Sciences of the United States of America,110(43):17273-17277
Tomizawa M,Casida JE.2003.Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors.Annual Review of Entomology,48(1):339-364
Wu YC,Xu ZP,Shao XS,Cheng JG,Li Z.2016.Toxicity of cycloxaprid to Aphis craccivora(Koch)and its effects on detoxification enzymes.Chinese Journal of Pesticide Science,18(6):710-716(in Chinese)[吴勇超,须志平,邵旭升,程家高,李忠.2016.环氧虫啶对苜蓿蚜的毒力及对其体内解毒酶活性的影响.农药学学报,18(6):710-716]
Xu HX,Zheng XS,Tian JC,Lai FX,He JC,LüZX.2017.Advances in the development and application of control technologies for insect pest management in paddy fields in China.Journal of Plant Protection,44(6):925-939(in Chinese)[徐红星,郑许松,田俊策,赖凤香,何家春,吕仲贤.2017.我国水稻害虫绿色防控技术的研究进展与应用现状.植物保护学报,44(6):925-939]
Zhang J,Cao YQ,Cui L,Qin ZH,Ma YQ,Rui CH.2015.Toxicity of N′-nitrohydrazinecarboximidamides to several aphids and the influence on the activities of related enzymes in Aphis gossypii.Chinese Journal of Pesticide Science,17(2):143-148(in Chinese)[张靖,曹亚琴,崔丽,覃兆海,马永强,芮昌辉.2015.N′-硝基缩氨基胍类化合物对蚜虫的室内毒力测定及相关酶活性的影响.农药学学报,17(2):143-148]
Zhang J,Fu Q,Wang H,Li J,Wang W,Yang Z,Ye Q,Li C,Li Z.2013.Enantioselective uptake and translocation of a novel chiral neonicotinoid insecticide cycloxaprid in youdonger(Brassica campestris subsp.chinensis).Chirality,25(11):686-691
Zhang YB,Qian H.2015.The global marketing and development of six classes of insecticides and new insecticides.Agrochemicals Today,(5):26-32(in Chinese)[张一宾,钱虹.2015.世界六大类杀虫剂的发展和新研发的杀虫剂品种.今日农药,(5):26-32]
Zhuang YY.2014.Study on the hydrolysis and the photodegradation of cycloxaprid in water.Master Thesis.Shanghai:East China University of Science and Technology(in Chinese)[庄英滢.2014.环氧虫啶水解及光解稳定性研究.硕士学位论文.上海:华东理工大学]