Tetramethrin 胺菊酯

胺菊酯

胺菊酯 是一种强力合成杀虫剂，属于拟除虫菊酯。这种白色结晶固体的熔点为65-80摄氏度。其混合立体异构体应用于商业产品。胺菊酯通常用于制造杀虫剂，它能影响昆虫的神经中枢系统。

【中文名称】胺菊酯
【化学称名称】3，4，5，6-四氢酞酰亚氨基甲基(±) 分子式
顺式，反式菊酸酯
【英文名称】tetramethrin;Neopynamin;Phthalthrin(FMC)
【CAS号】 7696-12-0
【分子式】C19H25NO4
【相对分子量或原子量】331.12
【密度】1.108
【熔点（℃）】60～80
【沸点（℃）】185～190（13.3帕，0.1毫米汞柱）
【性状】纯品为白色结晶固体，具有除虫菊一样的气味。

药品简介
用电子喷雾装置测定了鱼藤酮和非洲山毛豆提取物气雾剂对致倦库蚊和德国小蠊的击倒活性。结果表明,20min时,以鱼藤酮和非洲山毛豆粗分物(含鱼藤酮10%)为有效成分的气雾剂对致倦库蚊的击倒率都达到100%,击倒中时分别为10.5min和12.1min;而对德国小蠊的击倒率分别为73.63%和93.62%,击倒中时分别为18.8min和15.7min;说明非洲山毛豆粗分物对德国小蠊的生物活性高于鱼藤酮纯品。二者与右旋胺菊酯混用后,对两种害虫的击倒活性都显著提高。
用SE-30毛细管柱、160-300℃程序升温、以邻苯二甲酸二环已酯为内标物，气相色谱法同时测定家用气雾杀虫剂中有效成分胺菊酯、氯菊酯的含量。胺菊酯、氯菊酯的平均回收率分别为94．0%、95．4%，相对标准偏差分别为2．23%、6．73%。

溶解情况
在水中的溶解度很小，能溶于苯、二甲苯、煤油、甲苯、丙酮、氯仿、三氯乙烷等有机溶剂。25℃时溶解度（g/kg）为：丙酮400，苯500，乙醇45，甲苯400

理化性质
纯品为白色结晶固体，具有除虫菊一样的气味。原药(有效成分含量>70%)为黄色膏状物或凝固体，比重1108(20℃)，沸点185-190℃/O．1毫米汞柱，熔点60-80℃，闪点大于200℃，蒸汽压3．5×10书毫米汞柱(20℃)。30℃时在水中的溶解度为4.6ppm，25℃时在下列几种溶剂中的溶解度是：苯和二甲苯50%，甲苯和丙酮40%，甲醇5%，乙醇4.5%。在弱酸性条件下稳定。50℃下贮藏6个月后生物活性不失去。正常条件下，贮存稳定至少两年。

药品毒性
按我国农药毒性分级标准，胺菊酯属低毒杀虫剂。原药大鼠急性经口LD50>5000毫克/公斤，小鼠急性经口LD50雄性为1920毫克/公斤，雌性为2000毫克/公斤。大鼠急性经皮LD50>5000毫克/公斤。对皮肤和眼睛无刺激作用。在试验条件下，未见致突变、致癌作用和繁殖影响。以2000ppm胺菊酯喂饲大鼠6个月无影响。对鱼有毒，鲤鱼TLm(48小时)为O.18毫克/公斤。

作用特点
胺菊酯对蚊、蝇等卫生害虫具有快速击倒效果，但致死性能差，有复苏现象，因此要与其它杀虫效果好的药剂混配使用。该药对蜚蠊具有一定的驱赶作用，可使栖居在黑暗处的蜚蠊在胺菊酯的作用下跑出来又受到其他杀虫剂的毒杀而致死。该药为世界卫生组织推荐用于公共卫生的主要杀虫剂之一。

使用方法
胺菊酯单独使用效果不明显，主要是和一些有较强杀虫力而又对人畜低毒的卫生杀虫剂混配，制成喷洒剂或气雾剂。国内仅有扬州农药厂生产。

防护措施
为防止因施用农药而导致的急性或慢性中毒事故，使用农药过程中做好个人防护非常重要。主要注意以下几点：1）施药时应穿长衣裤，戴好口罩及手套，尽量避免农药与皮肤及口鼻接触；2）施药时不能吸烟，喝水和吃食物。3）一次施药时间不宜过长，最好在4小时内；4）接触农药后要用肥皂清洗，包括衣物；5）药具用后清洗要避开人畜饮用水源；6）农药包装废弃物要妥善收集处理，不能随便乱扔；7）农药应封闭贮藏于背光、阴凉和干燥处，远离食品、饮料、饲料及日用品等；8）孕妇、哺乳期妇女及体弱有病者不宜施药。如发生农药中毒，应立即送医院抢救治疗。

注意事项
1．避免光直射，应贮存在阴凉通风处。
2．该产品的贮存期为两年。

tetramethrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name tetramethrin (BSI, E-ISO, ANSI); tétraméthrine ((f) F-ISO); phthalthrin (JMAF)
IUPAC name cyclohex-1-ene-1,2-dicarboximidomethyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Alt: cyclohex-1-ene-1,2-dicarboximidomethyl (?-cis-trans-chrysanthemate
Roth: cyclohex-1-ene-1,2-dicarboximidomethyl (1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
3,4,5,6-tetrahydrophthalimidomethyl (?-cis-trans-chrysanthemate
Chemical Abstracts name (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
CAS RN [7696-12-0] EEC no. 213-711-6 Development codes FMC 9260; SP 1103 (Sumitomo) Official codes OMS 1011

PHYSICAL CHEMISTRY
Composition Tech. is c. 92% pure. Mol. wt. 331.4 M.f. C19H25NO4 Form Colourless crystals, with slight pyrethrum-like odour; (tech. is a colourless to light yellow-brown solid). M.p. 68-70 °C; (tech., 60-80 ºC) V.p. 2.1 mPa (25 °C) KOW logP = 4.6 (25 ºC) S.g./density 1.1 (20 ºC) Solubility In water 1.83 mg/l (25 ºC). In acetone, ethanol, methanol, hexane, n-octanol all >2 g/100 ml. Stability Sensitive to alkalis and strong acids; DT50 16-20 d (pH 5), 1 d (pH 7), <1 h (pH 9). Stable on storage up to c. 50 ºC. Stable in ketones, chloroform, xylene, common aerosol propellants, etc. Variable stability with inorganic carriers. F.p. 200 °C (Cleveland open cup)

COMMERCIALISATION
History Introduced by Sumitomo Chemical Co., Ltd and later by FMC Corp. (who no longer manufacture or market it). First registered in Japan in 1964. Patents JP 453929; JP 462108; US 3268398 all to Sumitomo Manufacturers Agro-Chemie; Changzhou Kangmei; Endura; Jiangsu Yangnong; Sumitomo

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Non-systemic insecticide with contact action. Gives rapid knockdown. Uses Normally used in combination with synergists (e.g. piperonyl butoxide) and other insecticides for control of flies, cockroaches, mosquitoes, wasps, and other insect pests in public health and home and garden use. Formulation types AE; DP; EC; EW; OE; UL; Oil. Compatibility Incompatible with mineral carriers such as kieselguhr, acidic clays and kaolin. Selected products: 'Neo-Pynamin' (Sumitomo); mixtures: 'Chinethrin' (+ permethrin+ piperonyl butoxide) (Agro-Chemie); 'Duracide' (+ piperonyl butoxide) (Endura); 'Multi-Fog DTP' (+ deltamethrin+ piperonyl butoxide) (Trithin)

OTHER PRODUCTS
'Py-Kill' (Killgerm) mixtures: 'Pesguard NB' (+ piperonyl butoxide) (Sumitomo); 'Amber' (+ cypermethrin+ piperonyl butoxide) (Trithin); 'Duracide P' (+ permethrin+ piperonyl butoxide) (Endura); 'Lexan Forte' (+ chlorpyrifos) (Kwizda); 'Metra-Side CTP' (+ chlorpyrifos+ piperonyl butoxide) (Trithin); 'Multi-Fog ATP' (+ alpha-cypermethrin+ piperonyl butoxide) (Trithin); 'PB' (+ Permethrin) (Trithin); 'Phinco - T 22' (+ permethrin+ piperonyl butoxide) (Vapco); 'Tornado-Forte+' (+ lambda-cyhalothrin+ piperonyl butoxide) (public health) (Vapco); 'ULV500' (+ phenothrin [(1R)-trans- isomer]+ piperonyl butoxide) (Trithin) Discontinued products mixtures: 'Duracide Cyp' * (+ cypermethrin+ piperonyl butoxide) (Endura)

ANALYSIS
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles. By glc (M. Horiba et al., Botyu-Kagaku, 1975, 40, 123), or by u.v. spectrometry (J. Miyamoto, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 345).

MAMMALIAN TOXICOLOGY
Reviews See A. J. Gray & D. M. Soderlund, Chapt. 5 in "Insecticides". Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritant to skin. Inhalation LC50 (4 h) for rats >2.73 mg/l air. NOEL In 13 w feeding trials, dogs receiving 5000 mg/kg diet showed no ill-effects. In 6 mo feeding trials, no-effect level for rats was 1500 mg/kg diet. Other No evidence of oncogenicity. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for rainbow trout 3.7, bluegill sunfish 16 mg/l. Daphnia EC50 (48 h) 0.11 mg/l. Bees Toxic to bees.

ENVIRONMENTAL FATE
EHC 98 (WHO, 1990). EHC 98 notes rapid abiotic degradation in air and water, rapid metabolism and excretion in mammals, and no tendency to accumulate in tissues. Animals In rats, following oral administration, around 95% of tetramethrin (metabolised) is eliminated in the urine and faeces within 5 days. The principal metabolite is 3-hydroxycyclohexan-1,2-dicarboximide (J. Miyamoto et al., J. Agric. Biol. Chem., 1968, 32, 628). Soil/Environment Degradation involves cleavage of the ester bond, leading to chrysanthemic acid derivatives and phenoxybenzoic acid. These are further metabolised by hydroxylation and conjugation.