DEET - Wikipedia

N,N-Diethyl-meta-toluamide, also called DEET (/diːt/) or diethyltoluamide, is the most common active ingredient in insect repellents. DEET FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Chemicalcompound FortheformerAustraliangovernmentdepartmentknownasDEET,seeDepartmentofEmployment,EducationandTraining. NottobeconfusedwithDDT. DEET Names PreferredIUPACname N,N-Diethyl-3-methylbenzamide Othernames N,N-Diethyl-m-toluamide Identifiers CASNumber 134-62-3 Y 3Dmodel(JSmol) Interactiveimage ChEBI CHEBI:7071 N ChEMBL ChEMBL1453317 N ChemSpider 4133 Y ECHAInfoCard 100.004.682 KEGG D02379 Y PubChemCID 4284 UNII FB0C1XZV4Y Y CompToxDashboard(EPA) DTXSID2021995 InChI InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3 YKey: MMOXZBCLCQITDF-UHFFFAOYSA-N YInChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3Key: MMOXZBCLCQITDF-UHFFFAOYAE SMILES O=C(c1cc(ccc1)C)N(CC)CC Properties Chemicalformula C12H17NO Molarmass 191.27g/mol Density 0.998g/mL Meltingpoint −33 °C(−27 °F;240 K) Boilingpoint 288to292 °C(550to558 °F;561to565 K) Pharmacology ATCcode P03BX02(WHO)QP53GX01(WHO) Hazards GHSlabelling: Pictograms Signalword Danger Hazardstatements H302,H315,H319,H402 NFPA704(fire diamond) 2 1 0 Safetydatasheet(SDS) ExternalMSDS Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandardstate(at25 °C[77 °F],100 kPa). N verify (whatis YN ?) Infoboxreferences Chemicalcompound N,N-Diethyl-meta-toluamide,alsocalledDEET(/diːt/)ordiethyltoluamide,isthemostcommonactiveingredientininsectrepellents.Itisaslightlyyellowoilintendedtobeappliedtotheskinortoclothingandprovidesprotectionagainstmosquitoes,flies,ticks,fleas,chiggers,leechesandmanybitinginsects. Contents 1History 2Preparation 3Mechanismandeffectiveness 4Concentrations 5Effectsonhealth 5.1Detectioninbodyfluids 6Effectsonmaterials 7Effectsontheenvironment 8Seealso 9References 10Furtherreading 11Externallinks History[edit] DEETwasdevelopedin1944[1]bySamuelGertler[1]oftheUnitedStatesDepartmentofAgricultureforusebytheUnitedStatesArmy,[2]followingitsexperienceofjunglewarfareduringWorldWarII.Itwasoriginallytestedasapesticideonfarmfields,andenteredmilitaryusein1946andcivilianusein1957.ItwasusedinVietnamandSoutheastAsia.[3] Initsoriginalform,knownas"bugjuice",theapplicationsolutionwascomposedof75%DEETand25%ethanol.[4]Later,anewversionoftherepellentwasdevelopedbytheU.S.ArmyandtheUSDA.ThisincarnationconsistedofDEETandamixtureofpolymersthatextendeditsreleaseandreduceditsevaporationrate.[4]Thisextended-releaseapplicationwasregisteredbytheEnvironmentalProtectionAgencyin1991.[4] Preparation[edit] Aslightlyyellowliquidatroomtemperature,itcanbepreparedbyconvertingm-toluicacid(3-methylbenzoicacid)tothecorrespondingacylchlorideusingthionylchloride(SOCl2),andthenallowingthatproducttoreactwithdiethylamine:[5][6] Mechanismandeffectiveness[edit] DEETisanextremelyeffectiveinsectrepellant,themosteffectiveavailable.[7]Itiseffectiveagainstavarietyofinvertebrates,includingticks,flies,mosquitos,andsomeparasiticworms.[7]DEETissuspectedtoaffecttwopathwaysinmosquitos:itaffectsodorantreceptorsatadistance,anditaffectschemoreceptorsuponcontact.[7]Theexactmechanismsarestillbeingresearched,butthetwomostlikelyhypothesesarethe"smellandavoidhypothesis"(thatDEEThasanunpleasantodortoinsects),andthe"confusanthypothesis"(thatsmellingDEETconfusesinsects).[7] Matsudaetal.1996findthatPelargoniumcitrosumisnotasourceofcitronellaoilandisnotaneffectivealternativetoDEET.[8] Concentrations[edit] TheconcentrationofDEETinproductsmayrangefromlessthan10percenttonearly100percent.Concentrationsof10to30percentarerecommendedforinfantsandchildren.DEETshouldnotbeusedonchildrenunder2monthsofage.[9] DEETisoftensoldandusedinsprayorlotioninconcentrationsupto100%.[10]ConsumerReportsfoundadirectcorrelationbetweenDEETconcentrationandhoursofprotectionagainstinsectbites.100%DEETwasfoundtoofferupto12hoursofprotectionwhileseverallowerconcentrationDEETformulations(20–34%)offered3–6hoursofprotection.[citationneeded]OtherresearchhascorroboratedtheeffectivenessofDEET.[11]TheCentersforDiseaseControlandPreventionrecommends30–50%DEETtopreventthespreadofpathogenscarriedbyinsects.[12] A2008studyfoundthathigherconcentrationsofDEEThaveanimprovedabilitytorepelinsectsthroughfabric.[13] Effectsonhealth[edit] Asaprecaution,manufacturersadvisethatDEETproductsshouldnotbeusedunderclothingorondamagedskin,andthatpreparationsbewashedoffaftertheyarenolongerneededorbetweenapplications.[14]DEETcanactasanirritant;[15]inrarecases,itmaycausesevereepidermalreactions.[14]Othersymptomsthatcanoccurarebreathingdifficulty,burningeyes,orheadaches.[16] Theauthorsofa2002studypublishedinTheNewEnglandJournalofMedicinewrote,"DespitethesubstantialattentionpaidbythelaypresseveryyeartothesafetyofDEET,thisrepellenthasbeensubjectedtomorescientificandtoxicologicalscrutinythananyotherrepellentsubstance,"continuing,"DEEThasaremarkablesafetyprofileafter40yearsofuseandnearly8billionhumanapplications,"concluding,"Whenappliedwithcommonsense,DEET-basedrepellentscanbeexpectedtoprovideasafeaswellaslong-lastingrepellenteffect."[17] WhenDEETisusedincombinationwithinsecticidesforcockroachesitcanstrengthenthetoxicityofcarbamate,anacetylcholinesteraseinhibitor.These1996findingsindicatethatDEEThasneurologicaleffectsoninsectsinadditiontoknownolfactoryeffects,andthatitstoxicityisstrengthenedincombinationwithotherinsecticides.[18] IntheDEETReregistrationEligibilityDecision(RED)in1998,theUnitedStatesEnvironmentalProtectionAgency(EPA)reported14to46casesofpotentialDEET-associatedseizures,includingfourdeaths.TheEPAstates:"...itdoesappearthatsomecasesarelikelyrelatedtoDEETtoxicity,"whichmayunderreporttheriskasphysiciansmayfailtocheckforhistoryofDEETuseorfailtoreportcasesofseizuresubsequenttoDEETuse.[19] In1997,thePesticideInformationProjectofCooperativeExtensionOfficesofCornellUniversitystatedthat"EvergladesNationalParkemployeeshavingextensiveDEETexposureweremorelikelytohaveinsomnia,mooddisturbancesandimpairedcognitivefunctionthanlesserexposedco-workers".[20] Whenusedasdirected,productscontainingbetween10%and30%DEEThavebeenfoundbytheAmericanAcademyofPediatricstobesafetouseonchildren,aswellasadults,buttheAcademyrecommendsthatDEETnotbeusedoninfantslessthantwomonthsold.[14] Citinghumanhealthreasons,HealthCanadabarredthesaleofinsectrepellentsforhumanusethatcontainedmorethan30%DEETina2002re-evaluation"basedonahumanhealthriskassessmentthatconsidereddailyapplicationofDEEToveraprolongedperiodoftime".TheagencyrecommendedthatDEET-basedproductsbeusedonchildrenbetweentheagesof2and12onlyiftheconcentrationofDEETis10%orlessandthatrepellentsbeappliednomorethan3timesaday,childrenunder2shouldnotreceivemorethan1applicationofrepellentinadayandDEET-basedproductsofanyconcentrationshouldnotbeusedoninfantsunder6months.[21][22]SomeexpertsrecommendagainstapplyingDEETandsunscreensimultaneouslysincethatwouldincreaseDEETpenetration;XiaochenGu,aprofessorattheUniversityofManitoba’sfacultyofPharmacywholedastudyaboutmosquitos,advisesthatDEETshouldbeapplied30ormoreminuteslater.[23] A2020studyperformedbystudentswithintheUniversityofFlorida'sCollegeofPublicHealthandHealthProfessionsanalyzeddatafromtheNationalHealthandNutritionExaminationSurveyandidentified1,205participantswhohad"DEETmetaboliclevelsrecordedatorabovedetectionlimits".Theyanalyzedbiomarkersrelatedtosystemicinflammation,immune,liver,andkidneyfunctions,andfoundno"evidencethatDEETexposurehasanyimpactonthebiomarkersidentified."[24] Detectioninbodyfluids[edit] DEETmaybemeasuredinblood,plasma,orurinebygasorliquidchromatography-massspectrometrytoconfirmadiagnosisofpoisoninginhospitalizedpatientsortoprovideevidenceinamedicolegaldeathinvestigation.BloodorplasmaDEETconcentrationsareexpectedtobeinarangeof0.3–3.0 mg/Lduringthefirst8hoursafterdermalapplicationinpersonsusingthechemicalappropriately,>6 mg/Linintoxicatedpatientsand>100 mg/Linvictimsofacuteintentionaloraloverdose.[25][26] Effectsonmaterials[edit] DEETisaneffectivesolvent,[15]andmaydissolvesomewatchcrystals,[4]plastics,rayon,spandex,othersyntheticfabrics,andpaintedorvarnishedsurfacesincludingnailpolish.Italsomayactasaplasticizerbyremaininginsidesomeformerlyhardplastics,leavingthemsoftenedandmoreflexible.DEETisincompatiblewithrayon,acetate,ordynelclothing. Effectsontheenvironment[edit] ThoughDEETisnotexpectedtobioaccumulate,ithasbeenfoundtohaveaslighttoxicityforfresh-waterfishsuchasrainbowtrout[27]andtilapia,[28]anditalsohasbeenshowntobetoxicforsomespeciesoffreshwaterzooplankton.[29]DEEThasbeendetectedatlowconcentrationsinwaterbodiesasaresultofproductionanduse,suchasintheMississippiRiveranditstributaries,wherea1991studydetectedlevelsvaryingfrom5to201ng/L.[30] A1975studyanalyzedtheeffectsofDEEToncommunitiesoffreshwaterorganismsnativetoChinesewaterwaysandfoundthatcomparedtoothercommercialinsectrepellants,DEETwasmoderatelytoxictoaquaticorganisms.Themost-at-riskorganismswerealgaecolonieswhichoftenexperienced"significantbiomassdeclineandcommunitycompositionshift[s]"whenexposedtoDEETat500 ng/L.[31] Seealso[edit] Beautyberry Citronellaoil DDT,anothermeansofdiseasevectorcontrol Icaridin Lemoneucalyptus Mosquitocoil p-Menthane-3,8-diol Permethrin,apyrethroid SS220 Anthranilate-basedinsectrepellents References[edit] ^abUS2408389,GertlerS,"N,N-diethylbenzamideasaninsectrepellent",published1946-10-01  ^KatzTM,MillerJH,HebertAA(May2008)."Insectrepellents:historicalperspectivesandnewdevelopments".JournaloftheAmericanAcademyofDermatology.58(5):865–71.doi:10.1016/j.jaad.2007.10.005.PMID 18272250.Retrieved2015-08-16. ^CommitteeonGulfWarandHealth:LiteratureReviewofPesticidesandSolvents(2003).GulfWarandHealth:Volume2.InsecticidesandSolvents.Washington,D.C.:NationalAcademiesPress.doi:10.17226/10628.ISBN 978-0-309-11389-2. ^abcdKitchenLW,LawrenceKL,ColemanRE(June2009)."TheroleoftheUnitedStatesmilitaryinthedevelopmentofvectorcontrolproducts,includinginsectrepellents,insecticides,andbednets".JournalofVectorEcology.34(1):50–61.doi:10.1111/j.1948-7134.2009.00007.x.PMID 20836805.[permanentdeadlink] ^WangBJ(1974)."Aninterestingandsuccessfulorganicexperiment(CEC)".J.Chem.Educ.51(10):631.doi:10.1021/ed051p631.2. ^PaviaDL(2004).Introductiontoorganiclaboratorytechniques(GoogleBooksexcerpt).CengageLearning.pp. 370–376.ISBN 978-0-534-40833-6. ^abcdDeGennaro,Matthew(2015)."Themysteriousmulti-modalrepellencyofDEET".Fly.9(1):45–51.doi:10.1080/19336934.2015.1079360.ISSN 1933-6942.PMC 4594586.PMID 26252744. ^ Debboun,Mustapha;Frances,StephenP.;Strickman,Daniel,eds.(2006-10-25).InsectRepellents.CRC.p. 495.doi:10.1201/9781420006650.ISBN 978-0-429-12338-2.Matsuda,BrentM.;Surgeoner,GordonA.;Heal,JamesD.;Tucker,ArthurO.;Maciarello,MichaelJ.(1996)."Essentialoilanalysisandfieldevaluationofthecitrosaplant"Pelargoniumcitrosum"asarepellentagainstpopulationsofAedesmosquitoes".JournaloftheAmericanMosquitoControlAssociation.AmericanMosquitoControlAssociation.12(1):69–74.ISSN 8756-971X.PMID 8723261.S2CID 29808835. ^AmericanAcademyofPediatrics,“SummerSafetyTips,”Dec2,2017https://www.healthychildren.org/English/safety-prevention/at-play/Pages/Summer-Safety-Tips-Staying-Safe-Outdoors.aspx ^RecordintheHouseholdProductsDatabaseofNLM ^WilliamsonD(3July2002)."Independentstudy:DEETproductssuperiorforfendingoffmosquitobites"(Pressrelease).UniversityofNorthCarolina. ^"ProtectionagainstMosquitoes,Ticks,FleasandOtherInsectsandArthropods".Travelers'Health–YellowBook.CentersforDiseaseControlandPrevention.2009-02-05. ^DitzenM,PellegrinoM,VosshallLB(2008)."InsectodorantreceptorsaremoleculartargetsoftheinsectrepellentDEET".Science.319(5871):1838–42.Bibcode:2008Sci...319.1838D.doi:10.1126/science.1153121.PMID 18339904.S2CID 18499590.{{citejournal}}:CS1maint:multiplenames:authorslist(link) ^abc"InsectRepellentUseandSafety".WestNileVirus.CentersforDiseaseControlandPrevention.2007-01-12. ^abPetherickA(2008-03-13)."HowDEETjamsinsects'smellsensors".NatureNews.doi:10.1038/news.2008.672.Retrieved2008-03-16. ^"Bugspraypoisoning".U.S.NationalLibraryofMedicine.October2015.Retrieved2016-06-25. ^FradinMS,DayJF(July2002)."Comparativeefficacyofinsectrepellentsagainstmosquitobites".TheNewEnglandJournalofMedicine.347(1):13–8.doi:10.1056/NEJMoa011699.PMID 12097535. ^MossJI(October1996)."SynergismoftoxicityofN,N-diethyl-m-toluamidetoGermancockroaches(Orthoptera:Blattellidae)byhydrolyticenzymeinhibitors".JournalofEconomicEntomology.89(5):1151–5.doi:10.1093/jee/89.5.1151.PMID 17450648. ^"ReregistrationEligibilityDecision:DEET"(PDF).U.S.EnvironmentalProtectionAgency,OfficeofPrevention,Pesticides,andToxicSubstances.September1998.pp. 39–40.Archivedfromtheoriginal(PDF)onOctober21,2012.Retrieved2012-09-08. ^"DEET".PesticideInformationProfile.EXTOXNET.October1997.Retrieved2007-09-26. ^"InsectRepellents".HealthyLiving.HealthCanada.August2009.Archivedfromtheoriginalon2010-04-11.Retrieved2010-07-09. ^"Re-evaluationDecisionDocument:PersonalinsectrepellentscontainingDEET(N,N-diethyl-m-toluamideandrelatedcompounds)"(PDF).ConsumerProductSafety.HealthCanada.2002-04-15.Retrieved2010-07-09. ^"Howtochoosethebestbugrepellent".BestHealth.Reader'sDigestAssociation,Inc.January2000.RetrievedJune14,2016.‘Anythingintendedfortopicaluseonlyshouldn’tbegoingintothebody,’saysXiaochenGu,aprofessorattheUniversityofManitoba’sfacultyofpharmacy,wholedthestudy. ^HaleemZM,YadavS,CushionML,TannerRJ,CarekPJ,MainousAG(2020)."ExposuretoN,N-Diethyl-Meta-ToluamideInsectRepellentandHumanHealthMarkers:PopulationBasedEstimatesfromtheNationalHealthandNutritionExaminationSurvey".AmJTropMedHyg.103(2):812–814.doi:10.4269/ajtmh.20-0226.PMC 7410448.PMID 32458781.{{citejournal}}:CS1maint:multiplenames:authorslist(link) ^TenenbeinM(September1987)."Severetoxicreactionsanddeathfollowingtheingestionofdiethyltoluamide-containinginsectrepellents".JAMA.258(11):1509–11.doi:10.1001/jama.258.11.1509.PMID 3625951. ^BaseltRC(2014).Dispositionoftoxicdrugsandchemicalsinman,10thedition.SealBeach,Ca.:BiomedicalPublications.p. 650.ISBN 978-0-9626523-9-4. ^U.S.EnvironmentalProtectionAgency.1980.OfficeofPesticidesandToxicSubstances.N,N-diethyl-m-toluamide(Deet)PesticideRegistrationStandard.December1980.83pp. ^MathaiAT,PillaiKS,DeshmukhPB(1989)."Acutetoxicityofdeettoafreshwaterfish,Tilapiamossambica :Effectontissueglutathionelevels".JournalofEnvironmentalBiology.10(2):87–91.Archivedfromtheoriginalon2007-11-07. ^SeoJ,LeeYG,KimSD,ChaCJ,AhnJH,HurHG(April2005)."BiodegradationoftheinsecticideN,N-diethyl-m-toluamidebyfungi:identificationandtoxicityofmetabolites".ArchivesofEnvironmentalContaminationandToxicology.48(3):323–8.doi:10.1007/s00244-004-0029-9.PMID 15750774.S2CID 31723995. ^ZeigerE,TiceR,BrevardB(1999)."N,N-Diethyl-m-toluamide(DEET)[134-62-3]–ReviewofToxicologicalLiterature"(PDF).Archivedfromtheoriginal(PDF)onOctober9,2012. ^SchmoldtA;BentheHF;HaberlandG(1975)."Digitoxinmetabolismbyratlivermicrosomes".BiochemPharmacol.24(17):1639–41.doi:10.1016/0006-2952(75)90094-5.PMID 10. Furtherreading[edit] FradinMS(June1998)."Mosquitoesandmosquitorepellents:aclinician'sguide".AnnalsofInternalMedicine.128(11):931–40.CiteSeerX 10.1.1.691.2193.doi:10.7326/0003-4819-128-11-199806010-00013.PMID 9634433.S2CID 35046348. Externallinks[edit] WikimediaCommonshasmediarelatedtoDEET. DEETGeneralFactSheet-NationalPesticideInformationCenter DEETTechnicalFactSheet–NationalPesticideInformationCenter WestNileVirusResourceGuide–NationalPesticideInformationCenter HealthAdvisory:TickandInsectRepellents,NewYorkState USCentersforDiseaseControlinformationonDEET USEnvironmentalProtectionAgencyinformationonDEET ReviewofscientificliteratureonDEET(fromaRANDCorporationreportonGulfWarillnesses) HealthCanada-Re-evaluationDecisionDocument:PersonalinsectrepellentscontainingDEET(N,N-diethyl-m-toluamideandrelatedcompounds),2002 Portals: Chemistry Insects Retrievedfrom"https://en.wikipedia.org/w/index.php?title=DEET&oldid=1097449608" Categories:HouseholdchemicalsInsectrepellentsBenzamidesHiddencategories:AllarticleswithdeadexternallinksArticleswithdeadexternallinksfromNovember2019ArticleswithpermanentlydeadexternallinksCS1maint:multiplenames:authorslistArticleswithshortdescriptionShortdescriptionmatchesWikidataArticleswithchangedEBIidentifierECHAInfoCardIDfromWikidataPagesusingcollapsiblelistwithbothbackgroundandtext-alignintitlestyleChemboxhavingGHSdataArticlescontainingunverifiedchemicalinfoboxesChemboximagesizesetAllarticleswithunsourcedstatementsArticleswithunsourcedstatementsfromJuly2022CommonscategorylinkisonWikidata Navigationmenu Personaltools NotloggedinTalkContributionsCreateaccountLogin Namespaces ArticleTalk English Views ReadEditViewhistory More Search Navigation MainpageContentsCurrenteventsRandomarticleAboutWikipediaContactusDonate Contribute HelpLearntoeditCommunityportalRecentchangesUploadfile Tools WhatlinkshereRelatedchangesUploadfileSpecialpagesPermanentlinkPageinformationCitethispageWikidataitem Print/export DownloadasPDFPrintableversion Inotherprojects WikimediaCommons Languages العربيةتۆرکجهCatalàČeštinaDeutschEspañolEuskaraفارسیFrançaisItalianoעבריתMagyarNederlands日本語NorskbokmålOccitanPolskiPortuguêsRomânăРусскийSlovenčinaСрпски/srpskiSrpskohrvatski/српскохрватскиSuomiSvenskaTürkçeУкраїнськаTiếngViệt中文 Editlinks