Tralomethrin 四溴菊酯

四溴菊酯

CAS号: 66841-25-6
英文名称: tralomethrin
化学名称：(1R,3S)-3-[(R,S)(1',2',2',2'-四溴乙基)]-2,2-二甲基环丙烷羧酸；cyano(3-phenoxyphenyl)methyl2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cycloprop;hag107;oethyl]-cyclopropanecarboxylate.;omoethyl]-cyclopropanecarboxylate;-phenoxyphenyl)methylester
其他名称：凯撒;刹克;四溴氰菊酯;溴氯氰聚酯
分子式：C22H19Br4NO3
分子量：665.01

理化性质：原药为黄色至橘黄色树脂状物质。相对密度1.7 (20℃)，蒸气压1.7Pa (1.73×10-11Pa） (25℃),[α]D+21 o～+27 o(50g/L甲苯）。能溶于丙酮、二甲苯、甲苯、二氯甲烷、二甲基亚砜、乙醇等有机溶剂；在水中溶解度为70mg/L。当50℃时，6个月不分解，对光稳定，无腐蚀性。

毒性：雄大鼠急性经口LD5099.2mg/kg，雌大鼠为157.2mg/kg；兔急性经皮LD50>2000mg/kg；大鼠急性吸入LC500.286mg/kg (4h)。对兔皮肤和眼睛有轻微刺激作用。大鼠2年饲喂试验无作用剂量为每天0.75mg/kg、小鼠为每天3mg/kg、狗每天1mg/kg。对大鼠、小鼠和兔无致畸作用。在大鼠三代繁殖试验中未见至繁殖有影响；在致癌试验剂量下，对大鼠和小鼠均呈阴性；Ames试验、细菌生长抑制试验、微核试验、活体外细胞遗传试验、显性致死试验等均呈阴性。虹鳟鱼LC500.0016mg/L (96h),蓝鳃鱼LC500.0043mg/L (96h)，水蚤LC5038mg/L (48h)。鹌鹑急性经口LD50>2510mg/kg。蜜蜂接触LD500.00012mg/只。

作用特点及杀虫谱：拟除虫菊酯类杀虫剂，具有触杀和胃毒作用。药剂通过昆虫表皮透透或食取经药剂处理后叶子进入体内。四溴菊酯通过抑制离子通道关闭能力，干扰调节钠离子流的离子通道，导致过多的钠离子进入细胞，从而对神经细胞产生神经冲动振幅，最终导致神经细胞兴奋完全消失、麻痹、虚脱而顽死亡。四溴菊酯可用于防治鞘翅目、同翅目、直翅目害虫，尤其是禾谷类、棉花、玉米、果树、烟草、蔬菜、水稻上的鳞翅目害虫。用量0.075～1.95g有效成分/100m2。

1、防治棉铃虫、红铃虫等，在卵孵化盛期，每亩用10.8%乳油10~15毫升，加水50~60千克喷雾。

2、防治甘蓝菜青虫、小菜蛾、蚜虫等，每亩用10.8%乳油3~5毫升，加水50~60千克喷雾。

剂型：10.8%乳油 ，1.5%高渗乳油

生产方法 ：
制备方法一
在四氯化碳溶剂中，二溴菊酸与溴加成，于20℃反应1h，得四溴菊酸，再与氯化亚砜在DMF和石油醚中转化为四溴菊酰氯，然后与α-氰基间苯氧基苯甲醇合成四溴菊酯。
制备方法二
二氯菊酰氯可通过多种途径获得较高产率，四溴菊酯氯可通过二氯菊酰氯与溴交换反应和加成反应制得，再与α-氰基间苯氧基苯甲醇作用合成四溴菊酯。
制备方法三
四溴菊酯与可采用溴氰菊酯在四氯化碳存在下加溴制得。

生产情况：江苏皇马农化有限公司；杭州易隆化工有限公司；扬农化工

其他：欧盟第2076/2002号法规禁止使用的３２０种农药里包括了四溴菊酯。

tralomethrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name tralomethrin (BSI, ANSI, draft E-ISO); tralométhrine (draft F-ISO)
IUPAC name (S)-a-cyano-3-phenoxybenzyl (1R,3S)-2,2-dimethyl-3-[(RS)-1,2,2,2-tetrabromoethyl]cyclopropanecarboxylate
Roth: (S)-a-cyano-3-phenoxybenzyl (1R)-cis-2,2-dimethyl-3-[(RS)-1,2,2,2-tetrabromoethyl]cyclopropanecarboxylate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropanecarboxylate
CAS RN [66841-25-6] unstated stereochemistry Development codes NU 831; RU 25474 (Roussel Uclaf); HAG 107 Official codes OMS 3048

PHYSICAL CHEMISTRY
Composition Laboratory grade tralomethrin (>93% a.i.) is a 60:40 mixture of two active diastereoisomers. Mol. wt. 665.0 M.f. C22H19Br4NO3 Form Yellow to beige, resinous solid (tech.). M.p. 138-148 ºC V.p. 4.8 ´ 10-6 mPa (25 °C) KOW logP = c. 5 (25 °C) S.g./density 1.70 (20 ºC) Solubility In water 80 mg/l. In acetone, dichloromethane, toluene, xylene >1000, dimethyl sulfoxide >500, ethanol >180 (all in g/l). Stability Stable for 6 months at 50 ºC. Acidic media reduce hydrolysis and epimerisation. Specific rotation [a]D +21?to +27?(50 g/l toluene) F.p. 26 ºC

COMMERCIALISATION
History Discovered and introduced by Roussel Uclaf (now Bayer CropScience). Patents FR 2364884 Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry Activity may be due to debromination to form deltamethrin (q.v.). Mode of action Non-systemic insecticide with contact and stomach action. Uses Insecticide with ingested and contact action. Controls a range of agronomic pests (Coleoptera, Homoptera, Orthoptera and particularly Lepidoptera, in cereals, coffee, cotton, fruit, maize, oilseed rape, rice, tobacco and vegetables), at 7.5-20 g/ha. If applied before infestations are well established, protects most crops against plant-sucking Hemiptera. Soil-surface sprays (5-10 g/ha) control cutworms (Agrotis and Euxoa spp.). Effective for wood protection, insect household pests, in public health, stored grains (Blattodea, Culicidae, Muscidae, grain borers and wood-attacking insects). Also very effective on Muscidae, Tabanidae, Ixodidae and other Acari on cattle, sheep and pigs, by application as dip, spray or pour-on. Formulation types EC; SC; WP. Selected products: 'Saga' (environmental health uses) (Bayer CropScience); 'Scout' (crop protection uses) (Bayer CropScience); 'Tralox' (veterinary use) (Intervet)

OTHER PRODUCTS
'Scout-Xtra' (Bayer CropScience); 'Stryker' (Bayer CropScience); 'Tracker' (DuPont); 'Tralate' (DuPont) Discontinued products mixtures: 'Synergin 1+2' * (+ amitraz) (Aventis)

ANALYSIS
Product analysis by hplc. Residues determined by glc with ECD.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 99-3000 mg a.i./kg, depending on the carrier used; for dogs >500 mg (in capsules)/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Moderate skin irritant; mild eye irritant (rabbits). Inhalation LC50 (4 h) for rats >0.40 mg/l air. NOEL (2 y) for rats 0.75 mg/kg b.w. daily; for mice 3 mg/kg b.w. daily; for dogs 1 mg/kg b.w. daily. ADI 0.0075 mg/kg b.w. Other Tech. not mutagenic or teratogenic in rats or rabbits. Toxicity class WHO (a.i.) II; EPA (formulation) III

ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2510 mg/kg. Dietary LC50 (8 d) for mallard ducks 7716, quail 4300 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.0016, bluegill sunfish 0.0043 mg/l. Daphnia LC50 (48 h) 38 ng/l. Low LC50 and LD50 values under laboratory conditions do not represent significant hazard to aquatic fauna in normal field use. Bees Non-toxic to honeybees. LD50 (contact) 0.12 mg/bee. Low LC50 and LD50 values under laboratory conditions do not represent significant hazard to bees in normal field use.

ENVIRONMENTAL FATE
Animals Tralomethrin is transformed into deltamethrin and further degraded. Plants Tralomethrin is transformed into deltamethrin. Soil/Environment Strongly adsorbed in soil; DT50 64-84 d. Kd 197-8784; Koc 43 796-675 667; highly immobile in various soils (sandy to clay loam).