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1、Chapter3:CarbamateInsecticides1.DevelopmentThecarbamateinsecticidesarethelatestarrivalinthefieldofanticholinesteraseinsecticides,andatpresentmanynewcompoundsarestillintheprocessofbeingmarketed.1CarbamateInsecticidesIngeneral,carbamateinsecticidesaresyntheticderivativesofphyso
2、stigmine(commonlycalledeserine),whichistheprincipalalkaloidoftheplantPhysostigmavenenosum(calabarbeans).2CarbamateInsecticidesPhysostigmavenenosum(calabarbeans).3CarbamateInsecticidesTheChemicalstructureofeserinewasanalysedin19254CarbamateInsecticidesPhysostigminewasknowntobe
3、aninhibitorofcholinesterase,andStedmanandEason(1932)workedtodevelopsyntheticanalogues,suchasprostigmine.5CarbamateInsecticidesAlthoughtheseandsimilarcompoundsareeffectiveinhibitorsofinsectcholinesterase,theyareunsuitableasinsecticides,fortheyarewater-solublequaternarysaltsora
4、minehydrochloridesandhencetoopolartopenetratetheinsectcuticle.6CarbamateInsecticidesKolbezenattributedtheirineffectivenessasinsecticidestotheirlowlipoidsolubility.O`Brienconsideredthattheion-impermeablesheathoftheinsectnervewouldalsocontributetotheirineffectiveness,forthesedr
5、ugswereionizedatphysiologicalpHandwouldthereforebeexcludedfromtheirsiteofaction.7CarbamateInsecticidesHencethemoderncarbamateinsecticideshavebeenmodifiedbyeliminatingthepolarmoietyofphysostigminesothattheycaneasilypenetratetheinsectcuticleaswellasthenervesheath.8CarbamateInse
6、cticidesThegeneralcarbamatestructureisO
7、
8、R1NH-C-OR2whereR1andR2arealkylorarylgroups.9CarbamateInsecticides1.Carbofuran(克百威,呋喃丹)ishighlytoxic,withanacuteoralLD50inratsof5mg/Kg.Itiseffectiveagainstsoilinsectsincorn,cottoninsects,andpestsonpotatoes.102.Temik(aldicarb)isanewtypeo
9、fsystemiccarbamateinsecticide,acaricide,andnematocidewhichisabsorbedintotherootsystemofplantsandhasaresiduallifeofupto10weeks.Temikishighlytoxic,withanacuteoralLD50inratsof1-30mg/kg.Itisrelativelysolubleinwater.CarbamateInsecticides11CarbamateInsecticides3.Methomylisawhitecry
10、stallinesolid.Itisfairlysolubleinwater.Itsacuteoraltoxicitytoratsis1
