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1、ImidaclopridImidacloprid吡虫啉吡虫啉Referencev1. Friederike Kramer, Norbert Mencke. Flea biology and control The Biology of the Cat Flea Control and Prevention with Imidacloprid in Small AnimalsM. Berlin:Springer-Verlag Berlin Heidelberg New York, 2001: 63-98.v2. Imidacloprid general fact sheet. National
2、Pesticide Information Center. http:/npic.orst.edu/factsheets/imidagen.html.v3. Imidacloprid general fact sheet. National Pesticide Information Center. http:/npic.orst.edu/factsheets/imidacloprid.html.v4. http:/pmep.cce.cornell.edu/profiles/extoxnet/haloxyfop-methylparathion/imidacloprid-ext.html. v5
3、. Toxicological evaluations imidacloprid. Pesticide residues in food 2001. http:/www.inchem.org/documents/jmpr/jmpmono/2001pr07.htm.2OutlinevHistory of ImidaclopridvPhysical / Chemical PropertiesvHow does imidacloprid work?vToxicological effectsvFate in the BodyvSummary 3History of ImidaclopridInthe
4、1960sthenaturallyoccurringinsecticidenicotinewassimplifiedbyYamamoto to 3-pyridylmethylamines, but none of these were of practicalvalue.Inrecenttimesaknock-downflyproductagainstM.domesticaL.家家蝇蝇containingnithiazinehasbeenavailable.In1985finallythechemistsofNihonTokushuNoyakuSeizoK.K.inJapansynthesiz
5、edamongothercompoundsthenitroguanidineNTN33893,knowntodayasimidacloprid.Theadditionofaheterocyclicsubstituent杂杂环环取取代代基基,the6-chloro-3-pyridyl-methylmoiety,tothenitromethylene substituted heterocycles (NMHs) increased the insecticidalactivity remarkably and further optimization 优优 化化finally resulted
6、in theinventionofimidaclopridfromNihonBayerAgrochem.K.K.Thusimidaclopridwasthefirstcommercializedmemberofanewclassofinsecticides,calledchloronicotinyl氯化烟酰氯化烟酰.4Physical / Chemical PropertiesvImidacloprid is made up of colorless crystals with a slight butcharacteristicodor气味气味.vMeltingpoint:144vSolub
7、ility(water):0.61g/Lat20vHydrolysishalf-life:30days(25atpH7)vAnaerobic厌氧的厌氧的half-life:27.1daysvAerobic好氧的好氧的half-life:997daysvSoilphotolysishalf-life:38.9daysvFielddissipationhalf-life:26.5229daysvSoiladsorptioncoefficient吸附系数吸附系数:Kd=0.9564.18/Koc=1323105How does imidacloprid work?Imidaclopriddisrup
8、ts破破坏坏thenervesabilitytosendanormalsignal,andthenervoussystemstopsworkingthewayitshould.Imidaclopridismuchmoretoxictoinsectsandotherinvertebrates无无脊脊椎椎动动物物thanitistomammals哺乳动物哺乳动物 andbirdsbecauseitbindsbettertothereceptorsofinsectnervecells.Imidaclopridisasystemicinsecticide内内吸吸性性杀杀虫虫剂剂,whichmeanst
9、hatplantstakeitupfromthesoilorthroughtheleavesanditspreadsthroughouttheplantsstems茎茎,leaves,fruit,andflowers.Insectsthatchew咀咀嚼嚼orsuck吸吸允允onthetreatedplantsendupeatingtheimidaclopridaswell.Oncetheinsectseattheimidacloprid,itdamagestheirnervoussystemandtheyeventuallydie.6Toxicological effects vAcute
10、ToxicityOralImidaclopridismoderatelytoxic中中等等毒毒性性ifingested摄摄取取.OralLD50valuesinratswereestimatedtobe450mg/kgforbothsexesinonestudyand500and380 mg/kg in males and females, respectively in another study.In mice,LD50values were estimated at 130 mg/kg for males and 170 mg/kg forfemales.Inhalation 吸入吸入I
11、midaclopridisvariable变变量量intoxicityifinhaled.TheinhalationLC50wasestimatedtobegreaterthan5323mg/m3fordust粉粉剂剂and69mg/m3foraerosol气气雾雾exposureinrats.Imidaclopriddustisconsideredslightlytoxicbuttheaerosolformishighlytoxic.7Toxicological effectsvAcute ToxicityDermal 皮肤皮肤Imidacloprid is very low in toxi
12、city via dermal exposure.The dermalLD50inratswasestimatedatgreaterthan5000mg/kg.Researchers did not observe eye or skin irritation刺刺激激 in rabbits兔兔子子.Imidaclopridisnotconsideredaskinsensitizer皮皮肤肤敏敏化化剂剂althoughreportsofhypersensitivity过过敏敏症症inskinfollowingexposuretoimidaclopridhavebeenreportedincomp
13、anionanimals.8Toxicological effectsvAcute ToxicitySigns of Toxicity AnimalspSalivation and vomiting流流涎涎和和呕呕吐吐 have been reported following oralexposure.Very high oral exposures may lead to lethargy嗜嗜 睡睡, vomiting,diarrhea腹腹泻泻,salivation,muscleweaknessandataxia运运动动失失调调,whichareallindicative of imidac
14、loprids action on nicotinic receptors.Other signs ofexposureathighdosesareuncoordinatedgait步步态态不不稳稳,tremors颤颤抖抖,andreducedactivity.pHypersensitivityreactions过过敏敏反反应应inskinhavebeenreportedfollowingdermalapplicationsofproductscontainingimidacloprid.pNeitherpersistentneurotoxic神神经经毒毒性性effectsnoreffects
15、withadelayedonsethavebeenreportedforimidacloprid.9Toxicological effectsvAcute ToxicitySigns of Toxicity HumanspA69-year-oldwomaningestedaformulatedproduct产产品品配配方方containing9.6%imidaclopridinN-methylpyrrolidesolution.Thewomansufferedseverecardiactoxicity心心脏脏毒毒性性anddeath12hoursaftertheexposure.Signsof
16、toxicitysoonaftertheingestionincludeddisorientation迷迷失失方方向向,sweating出出汗汗,vomiting呕吐呕吐,andincreasedheartandrespiratoryrates呼吸速率呼吸速率.pA24-year-oldmanwhoaccidentallyinhaledapesticidecontaining17.8%imidaclopridwhileworkingonhisfarmwasdisoriented迷迷失失方方向向,agitated焦焦虑虑,incoherent语无伦次语无伦次,sweatingandbreathl
17、essfollowingtheexposure.pPet owners have reported contact dermatitis following the use ofveterinaryproducts兽药产品兽药产品containingimidaclopridontheirpets.10Toxicological effectsvChronic Toxicity 慢性慢性A 2-year feeding study in rats fed up to 1,800 ppm resulted in a NoObservableEffectLevel(NOEL)of100ppm(5.7
18、mg/kgbodyweightinmalesand 7.6 mg/kg in females). Adverse effects副副作作用用included decreased bodyweightgaininfemalesat300ppm,andincreasedthyroidlesions甲甲状状腺腺病病变变inmalesat300ppmandfemalesat900ppm.A1-yearfeedingstudyindogsfedupto2,500ppmresultedinaNOELof1,250ppm(41mg/kg).Adverseeffectsincludedincreasedcho
19、lesterol胆胆固固醇醇levelsintheblood,andsomestresstotheliver(measuredbyelevatedlivercytochrome细胞色素细胞色素 p-450levels).11Toxicological effectsvMutagenic Effects 诱变诱变Imidacloprid may be weakly mutagenic. In a battery of 23 laboratorymutagenicity assays致致突突变变试试验验, imidacloprid tested negative for mutageniceffe
20、ctsinallbuttwooftheassays.Itdidtestpositiveforcausingchangesinchromosomes染染色色体体inhumanlymphocytes淋淋巴巴细细胞胞,aswellastestingpositiveforgenotoxicity基因毒性基因毒性inChinesehamsterovarycells仓鼠卵巢细胞仓鼠卵巢细胞.vEndocrine Disruption 内分泌紊乱内分泌紊乱Nodatawerefoundevaluatingthepotentialofimidaclopridtodisruptendocrinefunction
21、.12Toxicological effectsvCarcinogenicity 致癌致癌Imidaclopridisconsideredtobeofminimalcarcinogenicrisk,andisthuscategorizedbyEPAasaGroupEcarcinogen(evidenceofnoncarcinogenicityforhumans).Therewerenocarcinogeniceffectsina2-yearcarcinogenicitystudyinratsfedupto1,800ppmimidacloprid.vReproductive Effects 生殖
22、生殖A three generation reproduction study in rats fed up to 700 ppmimidacloprid resulted in a NOEL of 100 ppm (equivalent to 8 mg/kg/day)basedondecreasedpupbodyweightobservedatthe250ppmdoselevel.13Toxicological effectsvTeratogenic Effects 致畸致畸Adevelopmentaltoxicitystudyinratsgivendosesupto100mg/kg/day
23、bygavage灌灌胃胃 on days 6 to 16 of gestation妊妊娠娠 resulted in a NOEL of 30mg/kg/day (based on skeletal abnormalities骨骨骼骼异异常常 observed at the nexthighestdosetestedof100mg/kg/day).Inadevelopmentaltoxicitystudywithrabbitsgivendosesofimidaclopridbygavageduringdays6through19ofgestation, resulted in a NOEL of
24、 24 mg/kg/day based on decreased bodyweightandskeletalabnormalitiesobservedat72mg/kg/day(highestdosetested).14Toxicological effects15Fate in the BodyvAbsorptionThegastrointestinaltract胃胃肠肠道道 ofratsabsorbed92%ofanunspecifieddose. Plasma concentrations peaked血血 浆浆 浓浓 度度 达达 到到 高高 峰峰 2.5 hours afteradmi
25、nistration.Researcherstestedimidaclopridabsorptionusinghumanintestinalcells肠肠细细胞胞.Cells rapidly absorbed imidacloprid at a veryhighrate ofefficiency.Researchersconcludedthatanactivetransportsystemwasinvolved.vDistributionResearchersadministeredasingleoraldoseofradio-labeledimidaclopridat20mg/kgtomal
26、erats.Onehourafterdosing,imidaclopridwasdetectedthroughoutthebodieswiththeexceptionoffattytissues脂脂肪肪组组织织andthecentralnervoussystem.16Fate in the BodyvMetabolismTwo main routes ofmetabolismresponsibleforthedegradationofimidaclopridwereidentified.The main metaboliteswere6-chloronicotinicacidand its g
27、lycine conjugate,which were found only inurine.17Fate in the BodyvExcretion 排泄排泄Themetabolic products5-hydroxyandolefinderivatives resulting fromhydroxylationoftheimidazolidineringareexcretedinboththefeces粪粪便便andurine.Metabolitesfoundinurineinclude6-chloronicotinicacidanditsglycineconjugate,andaccou
28、ntedforroughly20%oftheoriginalradio-labeleddose.Ratsexcreted96%ofradio-labeledimidaclopridwithin48hoursfollowinganunspecifiedoraldosing,with90%excretedinthefirst24hours.Radio-labeledimidaclopridwaspresentinlowamountsinorgansandtissues24hoursaftermaleratswereorallydosedwith20mg/kg.18SummaryvChemical
29、Class:Chloro-nicotinyl.vUse: Systemic insecticide used for seed 种种子子 treatment, soil insects,termites白蚁白蚁 andahostofotheragriculturalandresidentialinsectpests.vToxicity rating:Moderatelytoxic中等毒性中等毒性.vHealth Effects:Itislinkedtoreproductiveandmutageniceffectsandisneurotoxic毒害神经的毒害神经的.vEnvironmental
30、Effects: Highly toxic to bees and other beneficialinsects,andistoxictouplandgamebirds高高地地猎猎鸟鸟.Itisgenerallypersistentinsoilsandcanleachtogroundwater.Ring necked pheasantBobwhite quailBlue GrouseSage GrouseChukarMountain QuailWild TurkeyDovesRuffed Grouse19RemarksvLD50/LC50:Acommonmeasureofacutetoxic
31、ityisthelethaldose(LD50)orlethalconcentration(LC50)thatcausesdeath(resultingfromasingleorlimitedexposure)in50percentofthetreatedanimals.uLD50isgenerallyexpressedasthedoseinmilligrams(mg)ofchemicalperkilogram(kg)ofbodyweight.uLC50is often expressed as mg of chemical per volume (e.g., liter (L) ofmedi
32、um(i.e.,airorwater)theorganismisexposedto.ChemicalsareconsideredhighlytoxicwhentheLD50/LC50issmallandpracticallynon-toxicwhenthevalueislarge.However,theLD50/LC50doesnotreflectanyeffectsfromlong-termexposure(i.e.,cancer,birthdefectsorreproductivetoxicity)thatmayoccuratlevelsbelowthosethatcausedeath.2
33、0RemarksvThehalf-lifeisthetime required forhalfofthecompoundtobreakdownintheenvironment.u1half-life=50%remainingu2half-lives=25%remainingu3half-lives=12%remainingu4half-lives=6%remainingu5half-lives=3%remainingHalf-livescanvarywidelybasedonenvironmentalfactors.Theamountofchemicalremainingafterahalf-lifewillalwaysdependontheamountofthechemical originally applied. It should be noted that some chemicals maydegradeintocompoundsoftoxicologicalsignificance.21Thank you !22结束结束
