Cyhalothrin 氯氟氰菊酯

氯氟氰菊酯

氯氟氰菊酯氯氟氰菊酯又叫三氟氯氰菊酯，属拟除虫菊酯类仿生物农药。具有杀虫广谱、高效、速度快、持效期长的特点。

中文名称：氯氟氰菊
英文名称：cyhalothrin
化学名称：(IR)-顺式-(Z)-2,2-二甲基-3-(2-氯-3,3,3-三氟-1-丙烯基)环丙烷羧酸-(S)-a-氰基-3-苯氧基苄酯/(IS)-顺式-(Z)-2,2-二甲基-3-(2-氯-3,3,3-三氟-1-丙稀基)环丙烷羧酸-(R)-a-氰基- 3-苯氧基苄酯(1：1的混合物)
结构或分子式：C23H19CIF3NO3
分子量：449.86
半衰期：4-12周
化学分类：拟除虫菊酯
分析方法：液谱法

化学品性质

理化性质
外观：白色固体
性状：黄色至棕色粘稠油状液体（工业品）　
含量：98%
密度：1.33
相对密度：1.25（25℃）
蒸汽压：2.67×10-10pa/20℃
熔点：49.2℃
沸点：（℃）187～190（2.67帕）
溶解性：难溶于水，21℃溶解5×10-3mg/L，可溶于多种普通有机溶剂中
溶解情况：
水溶解度<1毫克/升，溶于丙酮、二氯甲烷、甲苯等均>500克/升（20℃）
稳定性：在酸性溶液中稳定，在碱性溶液中易分解

急性毒性(大鼠)
口 服：LD50 79mg/kg
经 皮：D50 632mg/kg
慢性毒性：对大鼠无作用剂量为1.7-1.9mg/kg
刺激性：对眼睛和皮肤有轻度刺激
毒性等级：WHO(a.i.)(II)

化学品用途
为拟除虫菊酯类杀虫剂，能有效地防治棉花、果树、蔬菜、大豆等作物上的多种害虫，也能防治动物体上的寄生虫。

（1）英文通用名: cyhalothrin
（2）商品名称: 功夫、功夫菊酯、高效氯氟氰菊酯、大康、高福、天菊等。

（3）剂型
2.5%、10%可湿性粉剂，0.6%、2.5%乳油，2.5%水乳剂、1.5%悬浮剂，2.5%微胶囊剂。

（4）作用
对害虫和螨类具有强烈的触杀和胃毒作用，有渗透性而无内吸作用，可有效地防治鳞翅目、鞘翅目、半翅目和螨类害虫。其性质稳定，耐雨水冲刷。
可防治果树、蔬菜、棉花、烟草、玉米等作物的棉铃虫、棉红铃虫、棉蚜、玉米螟、柑橘潜叶蛾、介壳虫若虫、叶螨、卷叶蛾类幼虫、食心虫、蚜虫，小菜蛾、甘蓝夜蛾、斜纹夜蛾、烟青虫、菜螟、菜青虫，对蚊、蝇等卫生害虫也有效。
残效期长。施药1次，20天以后，防效仍可达90%以上。

（5）使用方法
①防治小菜蛾、菜青虫、甜菜夜蛾、斜纹夜蛾、烟青虫、菜螟等抗性害虫，在1-2龄幼虫发生期，每亩 氯氟氰菊酯
用2.5%乳油20-40毫升，兑水50千克喷雾。
②防治菜蚜、瓜蚜，每亩用2.5%乳油15-20毫升，加水50千克喷雾。防治茄子叶螨、辣椒跗线螨，每亩用2.5%乳油30-50毫升，加水50千克喷雾。
③防治枣、苹果、梨等果树的蠹蛾、小卷叶蛾，在低龄幼虫始发期或开花坐果期，用2.5%乳油2000-4000倍液喷雾。防治桃小食心虫、梨小食心虫、各种果树蚜虫，用2.5%乳油3000-4000倍稀释液喷雾。
④防治棉铃虫、棉红铃虫，每亩用2.5%乳油30-50毫升，加水50-100千克喷雾，可兼治棉花叶螨、棉象甲。防治棉蚜，苗期每亩用20毫升，伏蚜用20-30毫升，加水50千克喷雾。
⑤防治玉米螟，在卵孵化盛期施药，用2.5%乳油5000倍稀释液喷雾。

（6）注意事项
①不可与碱性农药混用，也不可做土壤处理剂。
②氯氟氰菊酯对鱼虾、蜜蜂、家蚕高毒，因此在使用时应防止污染鱼塘、河流、蜂场、桑园。
③禁止在水田使用。
④对拟除虫菊酯类农药产生抗性的害虫，应适当提高药液使用浓度。
⑤收获前21天停用。
⑥应存放在阴凉通风干燥处。

cyhalothrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name cyhalothrin (BSI, draft E-ISO, BAN); cyhalothrine ((f) draft F-ISO)
IUPAC name (RS)-a-cyano-3-phenoxybenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Roth: (RS)-a-cyano-3-phenoxybenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name [1a,3a(Z)]-(?-cyano-(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [68085-85-8] EEC no. 268-450-2 Development codes PP563; ICI 146 814 (both ICI) Official codes OMS 2011

PHYSICAL CHEMISTRY
Composition Tech. grade cyhalothrin has purity ³90% m/m, of which ³95% is cis- isomers. Mol. wt. 449.9 M.f. C23H19ClF3NO3 Form Yellow to brown viscous oil (tech.). B.p. Does not boil at atmospheric pressure V.p. 0.001 mPa (20 ºC, est.) KOW logP = 6.9 (20 ºC) S.g./density 1.25 (25 ºC) Solubility In water 0.005 mg/l (pH 6.5, 20 ºC). In acetone, dichloromethane, methanol, diethyl ether, ethyl acetate, hexane, toluene, all >500 g/l (20 ºC). Stability Stable to decomposition and cis/trans isomerisation for at least 4 years in the dark at 50 ºC. Stable to light; loss on storage in the light is <10% in 20 months. Decomposes at 275 ºC. Slowly hydrolysed by water in sunlight at pH 7-9, more rapidly at pH >9. pKa >9 (hydrolysis prevents measurement) F.p. 204 °C (tech., Pensky-Martens closed cup)

COMMERCIALISATION
History Insecticide reported by P. D. Bentley et al. (Pestic. Sci., 1980, 11, 156) and its acaricidal properties by V. K. Stubbs (Austral. Vet. J., 1982, 59, 152). Introduced by ICI Australia (now Crop Care Australasia Pty Ltd) and ICI Agrochemicals (now Syngenta AG) in the 1980s. Patents AU 521136; US 4183948; GB 2000764 Manufacturers Syngenta

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 and stomach action, and repellent properties. Gives rapid knockdown and long residual activity. Uses Control of animal ectoparasites, especially Boophilus microplus and Haematobia irritans on cattle, and Bovicola ovis, Linognathus spp. and Melophagus ovinus on sheep. Applied as an animal dip or as a spray around animal houses. Formulation types EC; WP. Selected products: 'Cyhalon' (Syngenta); 'Grenade' (Syngenta)

ANALYSIS
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles. By hplc (A. Jacques et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 9). Residues determined by glc with ECD (idem, ibid.). Details available from Syngenta.

MAMMALIAN TOXICOLOGY
Reviews JECFA 54, FAO/WHO 42, 43 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 166, female rats 114, guinea pigs >5000, rabbits >1000 mg/kg. Skin and eye Acute percutaneous LD50 for male rats 1000-2500, female rats 200-2500, rabbits >2500 mg/kg. Moderate eye irritant; not a skin irritant (rabbits). Moderate skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >0.086 mg/l. NOEL No significant toxicological effect observed in feeding trials with rats (2 y) or dogs (0.5 y) at 2.5 mg/kg daily. ADI (JECFA) 0.002 mg/kg b.w. (temporary) [2000]; (JMPR) 0.02 mg/kg b.w. [1984]. Other No evidence of carcinogenicity, mutagenicity or disturbed reproductive functions; no adverse effects on foetal development. A facial sensation may be experienced by users of the chemical; this is transient, with complete recovery. Toxicity class WHO (a.i.) II

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >5000 mg/kg. Fish LC50 (96 h) for rainbow trout 0.00054 mg/l. Daphnia LC50 (48 h) 0.38 mg/l.

ENVIRONMENTAL FATE
EHC 99 (WHO, 1990). Animals In rats, following oral administration, cyhalothrin is rapidly eliminated in urine and faeces. The ester group is hydrolysed, both moieties forming polar conjugates. Soil/Environment In soil, DT50 c. 4-12 weeks. Leaching of cyhalothrin and its degradation products through a range of soil types is negligible.