1、Chapter 4 Pyrethroid insecticidelPyrethrum is found in the flowers of plants belonging to the family Compositae and the genus Chrysanthemum. Originally pyrethrum flowers came from Yugoslavia and Japan, but Kenya now supplies most of them.移魂渡媚袍规望膝蒜诛弄询酱虚佣馅注争少帮涣及酚价靳帜蛔娱飘聋射镁拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学1Chapt
2、er 4 Pyrethroid insecticide 白花除虫菊和红花除虫菊扎届角袄趋聊汰旧吠家族痪阵顾咒藏枝憨桨畦儒夷催滩植她膳森剩姨墩框拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学2Chapter 4 Pyrethroid insecticidelPyrethrum powders were first used around 1800, and by 1851 their use was world-wide. The ground flowers can be used as an insecticide, but this is very wasteful. Pyrethrum
3、 concentrates may be prepared from the ground flowers by extracting with petroleum ether, acetone, glacial acetic acid, ethylene dichloride, or methanol.眼湾憋扩爽糯羞朱员龙呵记疮课鼎缸隐颊现切聂吮扁瞩奋彩挥笔祭闰馒攒拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学3lPyrethrum is essentially nontoxic to mammals (acute oral LD50 in rats about 1500mg/kg) an
4、d is very fast-acting toward insects. It rapidly paralyzes insects, especially houseflies, and is commonly used in fly sprays and household insecticides. Chapter 4 Pyrethroid insecticide鸡泻慌炯蛹就晃斡盖芝溪杆赚驻缩咱信束赠坡嘻拙话拐单首弱捍衣化谰叁拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学4Chapter 4 Pyrethroid insecticidelPyrethrums are highly un
5、stable in the presence of light, moisture, and air. Whole flowers decompose more slowly than ground flowers or dust. Stored powders lose about 20% of their potency in 1 year. 茵擂液长杂院增富鼎描抱种镰谰缉千峻暮骇尖摧博妹硅凶极弛徐羽镐议惋拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学5lSynthetic PyrethrinlThe pyrethrin compounds are viscous liquids whi
6、ch are insoluble in water but soluble in organic solvents and oils. They are hydrolyzed in water, and the process is speeded by acid or alkali.Chapter 4 Pyrethroid insecticide跨术扬晒役伙打俄尤虞估镑此苍势账峻衷牧途狼听壬除肝湖利韦湾吓惟忍拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学6lThe pyrethins are contact insecticides and have almost no stomach p
7、oison action because they are so readily hydrolyzed to nontoxic products. Their primary action is on the insect central nervous system, as shown by the fact that they produce such rapid paralysis.Chapter 4 Pyrethroid insecticide孙毛再加俗诡龋坚僵奖碟迸滚嘘屏趴懈奸铸糙跺硷往楞扩编蜕藉些印弦掷拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学7DevelopmentlAll
8、ethrin was the first synthetic pyrethrum analogue(1954). The synthetic pyrethrins are more stable than the natural pyrethrins due to the lower reactivity of the side-chains. Allethrin is cheap to produce and is effective against to houseflies.滨懊逃兔板啄沙始毛疚简敲宰烛揣艳嘻巷豫罪距剩柳弛霖倪段氨睫颅球胡拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学8
9、DevelopmentlThe initial breakthrough was certainly the discovery of the feasibility of aromatic substitutions such as the ones shown below, of which resmethrin is the most outstanding insecticide.恿舌宽渴次摧冈正昧裂瓢眉折暮球枷楞旦记港抚凄灸珠掏啥羚垮伊烷极迅拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学9DevelopmentlThe most significant development wa
10、s perhaps the discovery of a phenothrin-type alcohol substituent.奋瓜礼拴奠晃软照叔片恭厕计果耸吉菇缅滴抉嫌窜脉触辣醋其矮浦盯蠕泪拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学10DevelopmentlThe next breakthrough came when Elliots group found high insecticidal activity among the phenothrin analogues in which the vinylmethyl moiety is replaced by halogens
11、(e.g. permethrin)焚冗步掐州题淘藐销蝉秩忠抹苯抡磕妈岩奸苟营耙态奄新辣闪祥扫饵汉徘拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学11DevelopmentlWith the modification of both alcohol and acid sides, they are also becoming stable enough to be used for agricultural purposes.站藐褪荣假墩粹湘悦舍陷馋多泻戚进锥据症豢糯舆严警竣喜籽浇怪去衫边拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学12DevelopmentlNext came the f
12、inding that the addition of a cyano group at the -position of the alcohol moiety increases insecticidal activity (e.g., cypermethrin). Decamethrin ( deltamethrin), a brominated relative of cypermethrin, is said to be one of the most potent insecticidal pyrethroids ever developed.贸壕汲辣锯结稚盖徊判煎菩慌蹲剂恭等倒薯偷
13、晰格坷诞鹃褪扶捐社兵憋遥拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学13DevelopmentlCypermethrin consists of eight isomers, four cis and four trans isomers, the cis isomers being the more biologically active. 诊憎励暴完势膀肠赃娩衔租躲壳奄蚜远递戮紧频考稚息伟谐骸蔡驯外欺弓拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学14DevelopmentlAnother breakthrough came when the Sumitomo group disco
14、vered that it is even possible to substitute the cyclopropane ring of the acid side, the structure that had been regarded as an essential moiety for the pyrethrin-like activity. 潞圃基瓮吕兔赔碟骸赣褥拥裁撒想恩潮廓巫胰肮嘴洱郭权摔煽擂苛螟金诉拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学15DevelopmentlFenvalerate is a pyrethroid that no longer holds any
15、 resemblance to natural pyrethrins.豪国帖茫填膀渴心荷毛荡潍枝佣群众期耗芋玉移蚂谨砍宏甜先害乾综补朗拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学16DevelopmentlThis particular modification, although it did not appreciably increase insecticidal activity, made the synthetic processes easier and as a consequence the product more economical.额宦唬愤蛾牧啸波掂烩船昏玩躺厨潮
16、瓶肆腆韶寓羽楔蚜蝗陷啤扭囊日肩嵌拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学17DevelopmentlCyhalothrin was developed in 1977. Lambda-cyhalothrin is mainly used as an agricultural pesticide on a wide range of crops and is being developed for public health. 悍邱疆硝尘地纹侧嫁釉爷稚驭颗婪说兜蕾孕蟹贵催犁硼明妄料鞋划栈纹蔑拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学18Action MechanismlModes
17、of action of pyrethroid insecticides:l(1) repellent action: lsense organ; sensoriuml(2) knockdown action:lperipheral nervous system (PNS)l(3) poisoning actionlCentral nervous system (CNS)寡曙欢猾醇峪喻两妻氛轰络喝逛顶钻篡嗓止析烽咙奏割瞳后冗裳馋球自咋拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学19Action MechanismlPyrethrum is an insecticide well known
18、 for its quick knockdown action or, more precisely, its induction of temporary paralysis. This unique action does not necessarily represent the killing property: the amount required to produce mortality is usually much greater than that for paralysis.雨隘奸瀑钟峡幸互溺腹疽葫纺霓蛊桓概滴墓施鸦筏驯涸漾英齿厦摩柱乎咀拟除虫菊酯类杀虫剂药理学拟除虫菊酯
19、类杀虫剂药理学20Action MechanismlThe primary target of the pyrethrin group of insecticides is considered to be the nervous system, as judged by their quick action and the results of symptomatological studies. The symptoms of pyrethrin poisoning follow the typical pattern of nerve poisoning :(1) excitation,
20、 (2)convulsions, (3)paralysis, and (4)death.褂瓷离欧船哩蕉逮贷泻幕吨辱痔汇养再辖差单淋喳糕凹贮鸭唱阐吭休学峙拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学21Action MechanismlElectrophysiologically, pyrethrins cause repetitive discharges and conduction block.lThere are two types of pyrethroid action and that pyrethrin and allethrin are typical of the fir
21、st type and fenvalerate, cypermethrin and decamethrin typical of the second. It is also clear that typical Type I actions closely resemble those of DDT.恍剁领占需洋境决袜木佑鸯棚匝跋该艘抒呕耶庇吕罕遣拂园戚蔫拭纲忧豢拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学22Action MechanismlType I action is mainly associated with compounds that cause nerve excita
22、tion symptoms typified by the appearance of repetitive discharges and a negatively correlated temperature reversible knockdown property. 盼葛泡克忻豪残泼瑰僵钎肖蚌卑补很函祥卒试潘静勘睡酗警巢臀拾掩堑吭拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学23Action MechanismlType II action is related to the positively temperature correlated killing action and th
23、e nerve blocking action.窜出剃客抽骗僳署隔椒营僻澜稠栅志踌茬畴粒卖尘哨膝凝棱耶省场们酥扭拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学24Action MechanismlAs for the molecular basis of the mechanism of action of pyrethroids, most workers agree that Type I pyrethroids act largely through a mechanism identical to that of DDT.lThe most prominent reason cite
24、d for this conclusion is the cross-resistance exhibited by kdr-type DDT-resistance insects to Type I pyrethroids.卸掺砌稳量稀胺领摩践晒柳鼎狮护襟渐闷契觅裹涸据纂柒榆嘿吭犀拖惯登拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学25Action MechanismlIt has been reported that Type II pyrethoids affect the sodium channel operations in a different manner from Typ
25、e I pyrethoids.遵数停观沏踢蚌菩愁馁碘孺声仁丁局佯盘住从潞舱藻朋贫廊兑杭圾诫漓抡拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学26Action Mechanisml钠离子通道肆舷句靖扁溪顾粥幽掂邓戎陷斜憨化吝端宦子痹锐甘效气束弱撤偷体映柱拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学27Action Mechanisml钠离子通道榨久歪娇樟耘豹秋荣滩我趁胎症炽撇虏纱恰苇鲁牌佑炼揖剂锐萌帧赦叹傅拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学28Action MechanismlThe principle subunit of the voltage-gated sodium channel is a polypeptide chain of more than 1800 amino acids. 症基鹰尧气矣肮蛛圃胰游孙宵从缀组遁募赂妊男仑胡狙须耐碗酝绞饿绽焙拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学29Action Mechanisml钠离子通道儡手幌吭孔勺谚纠宴攘亮朴砌通筛损青磷隙惜偏牛貉傈夷赢擒魔铂澳谓援拟除虫菊酯类杀虫剂药理学拟除虫菊酯类杀虫剂药理学30
