多杀菌素类杀虫剂的环境降解及抗性机制研究进展
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摘要
多杀菌素类杀虫剂具有高效低毒、杀虫谱广及环境友好等优点,在害虫综合防治中具有很好的应用前景。近年的研究明确了多杀菌素和乙基多杀菌素的环境/农作物的降解代谢物及降解动力学,重点阐明了多杀菌素和乙基多杀菌素的代谢及靶标抗性机制,对多杀菌素类杀虫剂的合理使用和抗性治理提供了科学依据。同时,在杀虫活性更好、防治谱更广的乙基多杀菌素的开发过程中,计算建模、生物路径调控及化学合成等技术的综合应用发挥了巨大作用,为进行天然产物结构改造、开发新型杀虫剂提供了重要参考。本文论述了多杀菌素和乙基多杀菌素的结构特点及环境降解特性,综述了多杀菌素和乙基多杀菌素抗性机制的研究进展。
Spinosyn insecticides with advantages of high efficacy, low toxicity, broad spectrum and environmentally benign, are promising insecticides for the integrated pest management of pest insects.In recent years, the environmental degradation fate of spinosad and spinetoram including major metabolites and the degradation dynamics in soil, water and crops were reported. Moreover, the resistance mechanisms of insects to spinosad and spinetoram, especially metabolic resistance and targetmutation related resistance, were elucidated. These information is useful for rational application and resistance management of spinosad and spinetoram. Furthermore, technologies such as computational model-based quantitative structure-activity relationship(QSAR) analysis, the regulation of biosynthesis pathways and the organic synthesis played key roles in the discovery of spinetoram with much higher efficacy and broader insecticidal spectrum by modifying the structures of insecticidal natural products.In the review, the chemical structure characteristics and the research progresses on the environmental degradation of spinosad and spinetoram were summarized. Additionally, the achievements in the studies of resistance mechanisms to spinosad and spinetoram were also reviewed.
Spinosyn insecticides with advantages of high efficacy, low toxicity, broad spectrum and environmentally benign, are promising insecticides for the integrated pest management of pest insects.In recent years, the environmental degradation fate of spinosad and spinetoram including major metabolites and the degradation dynamics in soil, water and crops were reported. Moreover, the resistance mechanisms of insects to spinosad and spinetoram, especially metabolic resistance and targetmutation related resistance, were elucidated. These information is useful for rational application and resistance management of spinosad and spinetoram. Furthermore, technologies such as computational model-based quantitative structure-activity relationship(QSAR) analysis, the regulation of biosynthesis pathways and the organic synthesis played key roles in the discovery of spinetoram with much higher efficacy and broader insecticidal spectrum by modifying the structures of insecticidal natural products.In the review, the chemical structure characteristics and the research progresses on the environmental degradation of spinosad and spinetoram were summarized. Additionally, the achievements in the studies of resistance mechanisms to spinosad and spinetoram were also reviewed.
引文
[1]SILVA W M,BERGER M,BASS C,et al.Mutation(G275E)of the nicotinic acetylcholine receptorα6 subunit is associated with high levels of resistance to spinosyns in Tuta absoluta(Meyrick)(Lepidoptera:Gelechiidae)[J].Pestic Biochem Physiol,2016,131:1-8.
[2]THOMPSON G D,DUTTON R,SPARKS T C.Spinosad-a case study:an example from a natural products discovery programme[J].Pest Manag Sci,2000,56(8):696-702.
[3]SPARKS T C,DRIPPS J E,WATSON G B,et al.Resistance and cross-resistance to the spinosyns:a review and analysis[J].Pestic Biochem Physiol,2012,102(1):1-10.
[4]GALM U,SPARKS T C.Natural product derived insecticides:discovery and development of spinetoram[J].J Ind Microbiol Biotechnol,2016,43(2-3):185-193.
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[14]WANG D,QIU X H,REN X X,et al.Effects of spinosad on Helicoverpa armigera(Lepidoptera:Noctuidae)from China:tolerance status,synergism and enzymatic responses[J].Pest Manag Sci,2009,65(9):1040-1046.
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[22]CHEN C Y,HAN P,YAN W Y,et al.Uptake of quercetin reduces larval sensitivity to lambda-cyhalothrin in Helicoverpa armigera[J].JPest Sci,2017,91(2):919-926.
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[25]SAGRI E,RECZKO M,GREGORIOU M E,et al.Olive fly transcriptomics analysis implicates energy metabolism genes in spinosad resistance[J].BMC Genomics,2014,15:714.
[26]WANG W,MO J C,CHENG J A,et al.Selection and characterization of spinosad resistance in Spodoptera exigua(Hübner)(Lepidoptera:Noctuidae)[J].Pestic Biochem Physiol,2006,84(3):180-187.
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[28]REHAN A,FREED S.Selection,mechanism,cross resistance and stability of spinosad resistance in Spodoptera litura(Fabricius)(Lepidoptera:Noctuidae)[J].Crop Prot,2014,56:10-15.
[29]REYES M,ROCHA K,ALARCóN L,et al.Metabolic mechanisms involved in the resistance of field populations of Tuta absoluta(Meyrick)(Lepidoptera:Gelechiidae)to spinosad[J].Pestic Biochem Physiol,2012,102(1):45-50.
[30]MARKUSSEN M D K,KRISTENSEN M.Spinosad resistance in female Musca domestica L.from a field-derived population[J].Pest Manag Sci,2012,68(1):75-82.
[31]H?JLAND D H,SCOTT J G,JENSEN K M V,et al.Autosomal male determination in a spinosad-resistant housefly strain from Denmark[J].Pest Manag Sci,2014,70(7):1114-1117.
[32]SHI J,ZHANG L,GAO X W.Characterisation of spinosad resistance in the housefly Musca domestica(Diptera:Muscidae)[J].Pest Manag Sci,2011,67(3):335-340.
[33]KHAN H A A,AKRAM W,SHAD S A.Genetics,cross-resistance and mechanism of resistance to spinosad in a field strain of Musca domestica L.(Diptera:Muscidae)[J].Acta Tropica,2014,130:148-154.
[34]BIELZA P,QUINTO V,CONTRERAS J,et al.Resistance to spinosad in the western flower thrips,Frankliniella occidentalis(Pergande),in greenhouses of south-eastern Spain[J].Pest Manag Sci,2007,63(7):682-687.
[35]ZHANG S Y,KONO S,MURAI T,et al.Mechanisms of resistance to spinosad in the western flower thrip,Frankliniella occidentalis(Pergande)(Thysanoptera:Thripidae)[J].Insect Sci,2008,15(2):125-132.
[36]WATSON G B,CHOUINARD S W,COOK K R,et al.A spinosynsensitive Drosophila melanogaster nicotinic acetylcholine receptor identified through chemically induced target site resistance,resistance gene identification,and heterologous expression[J].Insect Biochem Mol Biol,2010,40(5):376-384.
[37]PERRY T,CHAN J Q,BATTERHAM P,et al.Effects of mutations in Drosophila nicotinic acetylcholine receptor subunits on sensitivity to insecticides targeting nicotinic acetylcholine receptors[J].Pestic Biochem Physiol,2012,102(1):56-60.
[38]WANG J,WANG X L,LANSDELL S J,et al.A three amino acid deletion in the transmembrane domain of the nicotinic acetylcholine receptorα6 subunit confers high-level resistance to spinosad in Plutella xylostella[J].Insect Biochem Mol Biol,2016,71:29-36.
[39]ROE R M,YOUNG H P,IWASA T,et al.Mechanism of resistance to spinosyn in the tobacco budworm,Heliothis virescens[J].Pestic Biochem Physiol,2010,96(1):8-13.
[40]GUILLéN J,BIELZA P.Thiamethoxam acts as a target-site synergist of spinosad in resistant strains of Frankliniella occidentalis[J].Pest Manag Sci,2013,69(2):188-194.
[41]PARK K H,CHOI J H,ABD EL-ATY A M,et al.Determination of spinetoram and its metabolites in amaranth and parsley using QuEChERS-based extraction and liquid chromatography-tandem mass spectrometry[J].Food Chem,2012,134(4):2552-2559.
[42]ZHAO L,CHEN G,ZHAO J,et al.Degradation kinetics of the insecticide spinetoram in a rice field ecosystem[J].Chemosphere,2015,119:1185-1191.
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[2]THOMPSON G D,DUTTON R,SPARKS T C.Spinosad-a case study:an example from a natural products discovery programme[J].Pest Manag Sci,2000,56(8):696-702.
[3]SPARKS T C,DRIPPS J E,WATSON G B,et al.Resistance and cross-resistance to the spinosyns:a review and analysis[J].Pestic Biochem Physiol,2012,102(1):1-10.
[4]GALM U,SPARKS T C.Natural product derived insecticides:discovery and development of spinetoram[J].J Ind Microbiol Biotechnol,2016,43(2-3):185-193.
[5]杜顺堂,朱明军,梁世中.生物农药多杀菌素的研究进展[J].农药,2005,44(10):441-444.DU S T,ZHU M J,LIANG S Z.Research progress on the biopesticide spinosad[J].Chin J Pestic,2005,44(10):441-444.
[6]华乃震.绿色环保生物杀虫剂多杀霉素和乙基多杀菌素的述评[J].农药,2015,54(1):1-5.HUA N Z.A review of green biological insecticide spinosad and spinetoram[J].Agrochemicals,2015,54(1):1-5.
[7]H?JLAND D H,JENSEN K M,KRISTENSEN M.Expression of xenobiotic metabolizing cytochrome P450 genes in a spinosadresistant Musca domestica L.strain[J].PLoS One,2014,9(8):e103689.
[8]CLEVELAND C B,BORMETT G A,SAUNDERS D G,et al.Environmental fate of spinosad.1.Dissipation and degradation in aqueous systems[J].J Agric Food Chem,2002,50(11):3244-3256.
[9]THOMPSON D G,HARRIS B J,LANTEIGNE L J,et al.Fate of spinosad in litter and soils of a mixed conifer stand in the acadian forest region of New Brunswick[J].J Agric Food Chem,2002,50(4):790-795.
[10]LIU S Z,LI Q X.Photolysis of spinosyns in seawater,stream water and various aqueous solutions[J].Chemosphere,2004,56(11):1121-1127.
[11]THOMPSON D G,HARRIS B J,BUSCARINI T M,et al.Fate of spinosad in litter and soils of a white spruce plantation in central Ontario[J].Pest Manag Sci,2002,58(4):397-404.
[12]WEST S D.Determination of the naturally derived insect control agent spinosad and its metabolites in soil,sediment,and water by HPLC with UV detection[J].J Agric Food Chem,1997,45(8):3107-3113.
[13]SáNTIS E L,HERNáNDEZ L A,MARTíNEZ A M,et al.Longterm foliar persistence and efficacy of spinosad against beet armyworm under greenhouse conditions[J].Pest Manag Sci,2012,68(6):914-921.
[14]WANG D,QIU X H,REN X X,et al.Effects of spinosad on Helicoverpa armigera(Lepidoptera:Noctuidae)from China:tolerance status,synergism and enzymatic responses[J].Pest Manag Sci,2009,65(9):1040-1046.
[15]ZHAO J Z,LI Y X,COLLINS H L,et al.Monitoring and characterization of diamondback moth(Lepidoptera:Plutellidae)resistance to spinosad[J].J Econ Entomol,2002,95(2):430-436.
[16]SHONO T,SCOTT J G.Spinosad resistance in the housefly,Musca domestica,is due to a recessive factor on autosome 1[J].Pestic Biochem Physiol,2003,75(1-2):1-7.
[17]KAKANI E G,ZYGOURIDIS N E,TSOUMANI K T,et al.Spinosad resistance development in wild olive fruit fly Bactrocera oleae(Diptera:Tephritidae)populations in California[J].Pest Manag Sci,2010,66(4):447-453.
[18]LOUGHNER R L,WARNOCK D F,CLOYD R A.Resistance of greenhouse,laboratory,and native populations of western flower thrips to spinosad[J].HortScience,2005,40(1):146-149.
[19]WAN Y R,YUAN G D,HE B Q,et al.Foccα6,a truncated nAChRsubunit,positively correlates with spinosad resistance in the western flower thrips,Frankliniella occidentalis(Pergande)[J].Insect Biochem Mol Biol,2018,99:1-10.
[20]LIU S S,LI Z M,LIU Y Q,et al.Promoting selection of resistance to spinosad in the parasitoid Cotesia plutellae by integrating resistance of hosts to the insecticide into the selection process[J].Biol Control,2007,41(2):246-255.
[21]BAO W X,NARAI Y,NAKANO A,et al.Spinosad resistance of melon thrips,Thrips palmi,is conferred by G275E mutation inα6subunit of nicotinic acetylcholine receptor and cytochrome P450detoxification[J].Pestic Biochem Physiol,2014,112:51-55.
[22]CHEN C Y,HAN P,YAN W Y,et al.Uptake of quercetin reduces larval sensitivity to lambda-cyhalothrin in Helicoverpa armigera[J].JPest Sci,2017,91(2):919-926.
[23]陈澄宇,史雪岩,高希武.昆虫对拟除虫菊酯类杀虫剂的代谢抗性机制研究进展[J].农药学学报,2016,18(5):545-555.CHEN C Y,SHI X Y,GAO X W.Mechanism of insect metabolic resistance to pyrethroid insecticides[J].Chin J Pestic Sci,2016,18(5):545-555.
[24]范银君,史雪岩,高希武.新烟碱类杀虫剂吡虫啉和噻虫嗪的代谢研究进展[J].农药学学报,2012,14(6):587-596.FAN Y J,SHI X Y,GAO X W.Research progresses on the metabolism of neonicotinoids imidacloprid and thiamethoxam[J].Chin J Pestic Sci,2012,14(6):587-596.
[25]SAGRI E,RECZKO M,GREGORIOU M E,et al.Olive fly transcriptomics analysis implicates energy metabolism genes in spinosad resistance[J].BMC Genomics,2014,15:714.
[26]WANG W,MO J C,CHENG J A,et al.Selection and characterization of spinosad resistance in Spodoptera exigua(Hübner)(Lepidoptera:Noctuidae)[J].Pestic Biochem Physiol,2006,84(3):180-187.
[27]WANG D,QIU X H,REN X X,et al.Resistance selection and biochemical characterization of spinosad resistance in Helicoverpa armigera(Hübner)(Lepidoptera:Noctuidae)[J].Pestic Biochem Physiol,2009,95(2):90-94.
[28]REHAN A,FREED S.Selection,mechanism,cross resistance and stability of spinosad resistance in Spodoptera litura(Fabricius)(Lepidoptera:Noctuidae)[J].Crop Prot,2014,56:10-15.
[29]REYES M,ROCHA K,ALARCóN L,et al.Metabolic mechanisms involved in the resistance of field populations of Tuta absoluta(Meyrick)(Lepidoptera:Gelechiidae)to spinosad[J].Pestic Biochem Physiol,2012,102(1):45-50.
[30]MARKUSSEN M D K,KRISTENSEN M.Spinosad resistance in female Musca domestica L.from a field-derived population[J].Pest Manag Sci,2012,68(1):75-82.
[31]H?JLAND D H,SCOTT J G,JENSEN K M V,et al.Autosomal male determination in a spinosad-resistant housefly strain from Denmark[J].Pest Manag Sci,2014,70(7):1114-1117.
[32]SHI J,ZHANG L,GAO X W.Characterisation of spinosad resistance in the housefly Musca domestica(Diptera:Muscidae)[J].Pest Manag Sci,2011,67(3):335-340.
[33]KHAN H A A,AKRAM W,SHAD S A.Genetics,cross-resistance and mechanism of resistance to spinosad in a field strain of Musca domestica L.(Diptera:Muscidae)[J].Acta Tropica,2014,130:148-154.
[34]BIELZA P,QUINTO V,CONTRERAS J,et al.Resistance to spinosad in the western flower thrips,Frankliniella occidentalis(Pergande),in greenhouses of south-eastern Spain[J].Pest Manag Sci,2007,63(7):682-687.
[35]ZHANG S Y,KONO S,MURAI T,et al.Mechanisms of resistance to spinosad in the western flower thrip,Frankliniella occidentalis(Pergande)(Thysanoptera:Thripidae)[J].Insect Sci,2008,15(2):125-132.
[36]WATSON G B,CHOUINARD S W,COOK K R,et al.A spinosynsensitive Drosophila melanogaster nicotinic acetylcholine receptor identified through chemically induced target site resistance,resistance gene identification,and heterologous expression[J].Insect Biochem Mol Biol,2010,40(5):376-384.
[37]PERRY T,CHAN J Q,BATTERHAM P,et al.Effects of mutations in Drosophila nicotinic acetylcholine receptor subunits on sensitivity to insecticides targeting nicotinic acetylcholine receptors[J].Pestic Biochem Physiol,2012,102(1):56-60.
[38]WANG J,WANG X L,LANSDELL S J,et al.A three amino acid deletion in the transmembrane domain of the nicotinic acetylcholine receptorα6 subunit confers high-level resistance to spinosad in Plutella xylostella[J].Insect Biochem Mol Biol,2016,71:29-36.
[39]ROE R M,YOUNG H P,IWASA T,et al.Mechanism of resistance to spinosyn in the tobacco budworm,Heliothis virescens[J].Pestic Biochem Physiol,2010,96(1):8-13.
[40]GUILLéN J,BIELZA P.Thiamethoxam acts as a target-site synergist of spinosad in resistant strains of Frankliniella occidentalis[J].Pest Manag Sci,2013,69(2):188-194.
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