Kadethrin 噻嗯菊酯

噻嗯菊酯

CAS号: 58769-20-3
英文名称： kadethrin
化 学 名 称 ： 右旋-顺式-2,2-二甲基-3(2,2,4,5-四氢-2-氧代-噻嗯-3-叉甲基)环丙烷羧酸(E)-5-苄基-3-呋喃甲基酯; (E)-5-benzyl-3-furylmethyl(1R,3S)-2,2-dimethyl-3(2,2,4,5-tetrahydro-2-oxothien-3-ylidenemethyl)cyclopropaneca1boxylate
其 他 名 称 ：克敌菊醋;硫茂苄呋菊酯;击倒菊酯；AI3-29117;ENT-29117;RU-15525;32271； Spray-Tox
分子式: C23H24O4S
分子量: 396.5

理化性质：黄棕色粘稠油状液,熔点31 C。比旋光度[a]D20+10。～+12。(5％乙醇溶液),20℃时的蒸气压<0.1mPa。工业品含量≥93％。能溶于乙醇、二氯甲烷、苯、丙酮、二甲苯和增效醚、微溶于煤油、而不溶于水(计算值1mg／L)。对光和热不稳定，在碱液中能水解,在矿油中分解较慢。其制剂封于铬质或内层涂漆的金属容器中可长期贮存。对马口铁有腐蚀性。

毒性 ：急性经口毒性LD50(mg／kg)：大鼠雄/雌1324/650，小鼠雄/雌121/124，狗>1000；急性经皮毒性LD50(mg／kg)：大小鼠>3200（雄雌）

本品对眼睛、皮肤和呼吸道器官有轻微刺激作用，但吸入不会引起任何中毒症状，大鼠每日喂剂量为12.5和25mg／kg的含药饲料，连续90天无影响。狗每日喂剂量为3和15mg／kg含药饲料,连续90天,亦未出现中毒症状。本品对雌性小鼠、大鼠和兔均无致畸作用。本品对鱼和蜜蜂有毒。虹鳟LC50(96小时)为0.13ug／L。

作用特点及杀虫谱：20世纪70年代问世的拟除虫菊酯杀虫剂，触杀性药剂，对昆虫主要有较高的击倒作用，但亦有一定的杀死活性，故常和生物苄呋菊酯混用，以增进其杀死效力。此外对蚊虫有驱赶和拒食作用。 但热稳定性差，不宜用以加工蚊香或电热蚊香片。主要用作卫生杀虫剂，防治蚊、蝇、蟑螂，具有击倒作用高的特色。制剂有气雾剂和喷射剂。

防治对象及其用量 本品点滴法对家蝇(雌)的毒力LD50为0.052～0.070／ug／虫;而除虫菊素、生物丙烯菊酯、S-生物丙烯菊酯、胺菊酯和生物苄呋菊酯则分别为0.320～0.390ug／虫、0.180～0.190ug／虫、0.094～0.100ug／虫、0.220～0.240ug／虫和0.008～0.O11ug／虫。当用本品与生物苄呋菊酯(0.036:0.054)加工的油基型气雾剂(剂量0.109mg／m3)喷射,对家蝇的KT995为4.3分钟,KT90 为14.5分钟,24小时的杀死率达96％。本品对埃及伊蚊和四斑按蚊幼虫的LD50为0.O05mg／kg,对埃及伊蚊成虫以5mg／L剂量直接喷雾,开始击倒死亡(KT)时间为5分钟,杀虫率达90％。当克敌菊酯浓度为0.05％,对尖音库蚊的半效致死时间为4.8分钟；剂量为0.O16mg／m3时,其击倒活性和杀死活性高出同剂量除虫菊素的1倍,以本品(0.02％)和生物苄呋菊酯(0.03％)复配的油基型气雾剂喷射蟑螂,KT50为1分钟;浓度增高1倍,则KT95亦只1分钟,6天的死亡率可达100％。水基型气雾剂的击倒作用不如油基型的好，但死亡率相似。
剂型 ：气雾剂和喷射剂(多数与生物苄呋菊酯混配)。克敌菊酯主要先加工成107浓缩液，然后用以配制各种气雾剂和喷射剂。

生产方法：以反式菊酸为原料，通过下列反应合成：

生产情况：噻嗯菊酯 1974年由J．Mariel和J．Buendia．1976年由J．Lhoste和F．Rauch报道其杀虫性能。由Roussel Vclaf(现为AgrEvo GmbH)开发，获专利FR2097244 IUS3842177。国内未见生产报道。

RU 15525
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
IUPAC name 5-benzyl-3-furylmethyl (E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate
Roth: 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate
Chemical Abstracts name [1R-[1a,3a(E)]]-[5-(phenylmethyl)-3-furanyl]methyl 3-[(dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylate
Other names kadethrin; kadethrine CAS RN [58769-20-3] EEC no. 261-433-0 Development codes RU 15 525 (Roussel Uclaf) Official codes ENT 29 117; AI3-29 117

PHYSICAL CHEMISTRY
Composition Tech. grade is ³93% pure m/m of stated stereoisomer. Mol. wt. 396.5 M.f. C23H24O4S Form Yellow-brown, viscous oil. M.p. 31 ºC V.p. <0.1 mPa (20 ºC) Solubility Practically insoluble in water. Soluble in dichloromethane, ethanol (10 g/kg), benzene, toluene, xylene, acetone, piperonyl butoxide. Slightly soluble in kerosene. Stability Hydrolysed by aqueous alkalis. Rapidly decomposed by light (more slowly in mineral oils). Unstable to heat. Specific rotation [a]D20 +16?to +19?(c. 50 g tech./l toluene) F.p. >100 ºC

COMMERCIALISATION
History Insecticide reported by J. Martel & J. Buendia (Int. Congr. Pestic. Chem. IUPAC, 3rd, 1974) and by J. Lhoste & F. Rauch (Pestic. Sci., 1976, 7, 247). Introduced by Roussel Uclaf (now Bayer CropScience). Patents FR 2097244; US 3842177

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Insecticide with contact action. Gives rapid knockdown. Uses Control of household insect pests, particularly houseflies, mosquitoes, and cockroaches. Normally used in combination with other pyrethroid insecticides and synergists. Formulation types Aerosol; OL; TC. Compatibility Incompatible with alkaline materials.

OTHER PRODUCTS
'Kadethrin' (Bayer CropScience); 'Kadethrine' (Bayer CropScience)

ANALYSIS
Product analysis by glc or hplc; details available from Bayer CropScience.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 1324, female rats 650, dogs >1000 mg/kg. Skin and eye Acute percutaneous LD50 for female rats >3200 mg/kg. Slight irritant to skin, eyes, and respiratory tract. Inhalation Inhalation trials (10 d) with rats and guinea pigs at 200 times normal dose in aerosols tolerated perfectly. NOEL (90 d) for rats 25, dogs 15 mg/kg b.w. daily. Other No teratogenic effect was observed in mice, rats or rabbits.

ECOTOXICOLOGY
Fish Toxic to fish; LC50 (96 h) for rainbow trout 0.13 mg/l. Bees Toxic to bees.

ENVIRONMENTAL FATE
Animals In rats, following oral administration, there is rapid metabolism (by opening of the thiolactone ring, cleavage of the ester, and ring hydroxylation), and rapid excretion. See K. Ohsawa & J. E. Casida (J. Agric. Food Chem., 1980, 28, 250-255).