Cypermethrin 氯氰菊酯

氯氰菊酯

氯氰菊酯氯氰菊酯，又称灭百可、安绿宝等，工业品为黄色至棕色粘稠固体，60℃时为粘稠液体。是一种杀虫剂。

介绍
中文名称：灭百可、兴棉宝、安绿宝、赛波凯、氯氰菊酯、奋斗呐
英文名称：Cypermethrin. Barricade. Basathrin. Cymbush. Cymperator. Ammo. Anomethrin
CAS编号：86753-92-6
理化特性
化学式：C22H19CL2NO3
分子量：416.32
性状：工业品为黄色至棕色粘稠固体，60℃时为粘稠液体。
熔点：60-80℃
相对密度（水=1）：1.1
蒸气压：20℃为2.3×107Pa
挥发度：对光稳定，温度>220℃时缓慢重量损失，在弱酸中性条件下稳定，遇碱分解，水解半衰期为1天。
溶解度：难溶于水，在醇、氯代烃类、酮类、环己烷、苯、二甲苯中溶解>450g/L。
闪点：80℃
油水分配系数：辛醇/水分配系数的对数值：6.3
危险性
加热超过220℃，该物质分解生成氰化物气体。
毒性

5.1急性毒性：属中等毒类。大鼠经口LD50251mg/kg，经皮剂量达1600 mg/kg未见死亡，吸入LC50>0.048mg/ L，大鼠静注6mg/kg；小鼠经口LD5082 mg/kg；兔经皮LD50>2400mg/kg。禽鸟口服LD50>2000mg/kg，鱼高毒，对蜂蚕有巨毒。动物急性中毒表现为共济失调，步态不稳，偶有震颤，存活者3天后恢复正常。本品对皮肤粘膜有刺激作用。
5.2慢性毒性：以1600ppm的饲料喂大鼠3个月，在头5周有步态异常等中毒症状出现，自第6周起逐渐恢复。病理学检查发现少数染毒动物坐骨神经轴突变形。慢性经口无作用剂量为5 mg/kg/d。，
5.3诱变性：本品不是诱导剂，但是用大剂量的本品小 鼠腹腔60mg/kg/d（连续），小鼠经口56mg/kg/7d（连续），小鼠经皮2520mg/kg/7d（连续）可引起小鼠骨髓微核细胞短暂性增加。在人类、细菌和仓鼠细胞培养以及小鼠肝脏的诱导试验阴性
5.4致癌性：无明确的资料显示本品有致癌作用。
5.5致畸性：无致畸作用。大鼠以70 mg/kg/d喂饲、家兔以30 mg/kg/d喂饲后代无出生缺陷。另有报道大鼠（未报告途径）（TDLo）： 400 mg/kg（孕6-15 d）胚胎毒性；小鼠腹腔(TDLo)：30mg/kg（雄1-4 d）影响精子形成。
5.6体内转归：小鼠口服后，24 h后即有27-80%以膀胱代谢物N-（3-苯氧基苯甲酰）-牛磺酸的产物从尿中排出
吸入中毒：给予新鲜空气，休息，并予以医疗护理。
皮肤接触：脱掉污染衣服，冲洗，然后用水和肥皂洗皮肤。
眼接触：首先用大量水冲洗几分钟（如方便取下隐型眼镜），然后就医。
摄食中毒：立即获得医疗护理。

我国农残标准中最大残留量
小麦，棉籽，黄瓜——————————————0.2mg/kg
玉米，大豆—————————————————0.05mg/kg
叶菜类蔬菜，梨果类水果，柑橘类水果—————2mg/kg
果菜类蔬菜，豆类蔬菜————————————0.5mg/kg
茶叶————————————————————20mg/kg
欧盟最新农残标准
茶叶中最大残留量（MRL）——————————0.5mg/kg

cypermethrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name cypermethrin (BSI, E-ISO, ANSI, BAN); cyperméthrine ((f) F-ISO)
IUPAC name (RS)-a-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Roth: (RS)-a-cyano-3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [52315-07-8] (formerly [69865-47-0], [86752-99-0] and many other numbers) Development codes NRDC 149; PP383 (ICI); WL 43 467 (Shell); LE 79-600 (Rhône-Poulenc); FMC 30980 Official codes OMS 2002

PHYSICAL CHEMISTRY
Composition Tech. grade is 90% pure. Mol. wt. 416.3 M.f. C22H19Cl2NO3 Form Odourless crystals; (tech., yellow-brown viscous semi-solid at ambient temperatures). M.p. 61-83 °C, depending on isomer ratio V.p. 2.0 ´ 10-4 mPa (20 ºC) KOW logP = 6.6 Henry 2.0 ´ 10-2 Pa m3 mol-1 (calc.) S.g./density 1.24 (20 ºC) Solubility In water 0.004 mg/l (pH 7). In acetone, chloroform, cyclohexanone, xylene >450, ethanol 337, hexane 103 (all in g/l, 20 ºC). Stability Relatively stable in neutral and weakly acidic media, with optimum stability at pH 4. Hydrolysed in alkaline media; DT50 1.8 d (pH 9, 25 °C); stable at pH 5 and 7 (20 °C). Relatively stable to light in field situations. Thermally stable up to 220 ºC. F.p. Not auto-flammable; non-explosive

COMMERCIALISATION
History Insecticide reported by M. Elliott et al. (Pestic. Sci., 1975, 6, 537). Developed by Ciba-Geigy, ICI (both now Syngenta AG), Mitchell Cotts and Shell International Chemical Co. (now BASF AG). Patents GB 1413491 to NRDC Manufacturers Agro-Chemie; Agrochem; Aimco; Ankur; Atabay; BASF; Bharat; DE-NOCIL; Dhanuka; Dow AgroSciences; Ficom; FMC; Gharda; Jiangsu Yangnong; Krishi Rasayan; Lucava; Meghmani; Mitchell Cotts; Mitsu; Parry; Rallis; Rotam; RPG; SC Enviro Agro; Sharda; Sundat; Syngenta; Tagros; United Phosphorus

APPLICATIONS
Biochemistry Acts on the nervous system of the insect, disturbs the function of neurons by interaction with the sodium channel. Mode of action Non-systemic insecticide with contact and stomach action. Also exhibits anti-feeding action. Good residual activity on treated plants. Uses Control of a wide range of insects, especially Lepidoptera, but also Coleoptera, Diptera, Hemiptera, and other classes, in fruit (including citrus), vines, vegetables, potatoes, cucurbits, lettuce, capsicums, tomatoes, cereals, maize, soya beans, cotton, coffee, cocoa, rice, pecans, oilseed rape, beet, ornamentals, forestry, etc. Control of flies and other insects in animal houses; and mosquitoes, cockroaches, houseflies and other insect pests in public health. Also used as an animal ectoparasiticide. Formulation types EC; GR; UL; WP. Compatibility Incompatible with alkaline materials. Selected products: 'Basathrin' (BASF); 'Cymbush' (Syngenta); 'Cymperator' (Syngenta); 'Ripcord' (BASF); 'Agrotrina' (Westrade); 'Alfa' (Trithin); 'Arrivo' (FMC); 'Cekumetrin' (Cequisa); 'Ciper QL' (Inquiport); 'Cynoff' (FMC); 'Cyperguard' (Gharda, Nufarm UK); 'Cyperil' (Agro-Chemie); 'Cypersan' (Dow AgroSciences); 'Cyproid' (Aimco); 'Cyrux' (United Phosphorus); 'Cythrine' (Agriphar); 'Demar' (Mitsu); 'Devicyper' (Devidayal); 'Drago' (Inquiport); 'Durin' (Dhanuka); 'Grand' (Sanonda); 'Hilcyperin' (Hindustan); 'Kecip' (Kemio); 'Kruel' (Reposo); 'Lacer' (RPG); 'Mortal' (Crop Health); 'Ralothrin' (Rallis); 'Ranjer' (Ramcides); 'Rasayanrin' (Krishi Rasayan); 'Rocyper' (Rotam); 'Starcyp' (Shaw Wallace); 'Suraksha' (Nagarjuna Agrichem); 'Termicidin' (Vapco); 'Visher' (Vipesco); 'Volcyper' (Ralchem); mixtures: 'Quick' (+ quinalphos) (Nagarjuna Agrichem)

OTHER PRODUCTS
'Barricade' (BASF); 'Cyperkill' (Mitchell Cotts, Chiltern); 'Demon' (Syngenta); 'Flectron' (BASF); 'Folcord' (BASF); 'Gammexane' (Argentina) (Syngenta); 'Imperator' (Syngenta); 'Permasect C' (Mitchell Cotts, Nufarm UK); 'Stockade' (BASF); 'Toppel' (Syngenta); 'Agrocyde' (Tecomag); 'Agrocyper' (Chemvet); 'Agro-Cypethrin' (AgroSan); 'Ammo' (FMC); 'Arjun' (Parry); 'Auzar' (Biostadt); 'Cipermin' (Chemiplant); 'Combat' (Agricultura Nacional); 'Counter' (public health) (Vapco); 'Cypcord' (BEC); 'Cyper-Atac' (Trithin); 'Cypertox' (FCC, Crystal); 'Devicyprin' (Devidayal); 'Indothrin' (Indofil); 'Kepermin' (Kemio); 'Killer' (public health) (Vapco); 'Kripcord' (Krishi Rasayan); 'Kyclothrin' (Papaeconomou); 'MCC 25' (Chiltern); 'Prik' (Kemio); 'Pucara' (CAS); 'Record' (Ramcides); 'Rudra' (Parry); 'Scipio' (Bayer CropScience); 'Sherpa' (Bayer CropScience); 'Sniper' (public health) (Vapco); 'Syper' (Agrochem); 'Trofy' (RPG); 'Ustaad' (United Phosphorus) mixtures: 'Polytrin C' (+ profenofos) (Syngenta); 'Amber' (+ piperonyl butoxide+ tetramethrin) (Trithin); 'Anaconda' (+ chlorpyrifos) (Aimco); 'Baytan T' (+ triadimenol) (seed treatment) (Bayer CropScience); 'Concentrate 2' (+ chlorpyrifos) (Trithin); 'Dorsan-C' (+ chlorpyrifos) (Luxembourg); 'Fency' (+ fenitrothion) (Efthymiadis); 'Ideal-2' (+ chlorpyrifos) (Indofil); 'Mega C-505' (+ chlorpyrifos) (Crop Health); 'Murfothrin' (+ mecarbam) (Efthymiadis); 'Nagata' (+ ethion) (Rallis); 'Ninja' (+ methamidophos) (Reposo); 'NPB' (+ piperonyl butoxide+ bioallethrin S-cyclopentenyl isomer) (Trithin); 'Pestan super' (+ chlorpyrifos) (Efthymiadis); 'Premis 25' (+ triticonazole) (Bayer CropScience, BASF); 'Raxil C' (+ tebuconazole) (seed treatment, Australia) (Bayer CropScience); 'SFB' (+ muscalure) (Trithin); 'Sherdiphos' (+ dimethoate+ triazophos) (Bayer CropScience); 'Ulka' (+ chlorpyrifos) (Biostadt) Discontinued products: 'Ambush C' * (Zeneca); 'Afrisect' * (Stefes); 'Cyper 10' * (Quadrangle); 'Cypercopal' * (Gilmore); 'Siege' * (Chemsearch) mixtures: 'Tifatol' * (+ CGA 50 439) (cypermethrin is rich in cis- isomers) (Novartis); 'Duracide Cyp' * (+ piperonyl butoxide+ tetramethrin) (Endura)

ANALYSIS
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles. By glc with FID (AOAC Methods, 17th Ed., 985.03, 986.02; CIPAC Handbook, 1985, 1C, 2047; A. Sapiets et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 33); total cypermethrin and diastereoisomer ratio by hplc with u.v. detection (CIPAC Handbook, 1985, 1C, 2052. 1994). Residues determined by glc with ECD (idem, ibid.; AOAC Methods, 17th Ed., 998.01). Details available from BASF or Syngenta.

MAMMALIAN TOXICOLOGY
Reviews See A. J. Gray & D. M. Soderlund, Chapt. 5 in "Insecticides". See also JECFA 47, FAO/WHO 36, 37 (see part 2 of Bibliography). Oral Acute oral LD50 for rats 250-4150 (tech. 7180), mice 138 mg/kg. Skin and eye Acute percutaneous LD50 for rats >4920, rabbits >2460 mg/kg. Slight skin and eye irritant (rabbits). May be a weak skin sensitiser. Inhalation LC50 (4 h) for rats 2.5 mg/l. NOEL (2 y) for dogs 5, rats 7.5 mg/kg. ADI (JECFA evaluation) 0.05 mg/kg b.w. [1996]; (JMPR) 0.05 mg/kg b.w. [1981]. Other Oral toxicity values for cypermethrin depend on such factors as: carrier, cis:trans ratio of the sample, species, sex, age and degree of fasting. Values reported sometimes differ markedly. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification (Xn; R20/22| R43| N; R50)

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >10 000, chickens >2000 mg/kg. Fish LC50 (96 h) for rainbow trout 0.69, sheepshead minnow 2.37 mg/l; under field conditions, fish are not at risk from normal agricultural usage. Daphnia LC50 (48 h) 0.15 mg/l. Bees Highly toxic to honeybees in laboratory tests, but field applications at recommended dosages do not put hives at risk. LD50 (24 h) (oral) 0.035 mg/bee; (topical) 0.02 mg/bee. Other beneficial spp. Not toxic to Collembola (J. A. Wiles & G. K. Frampton, Pestic. Sci., 47, 273 (1996)).

ENVIRONMENTAL FATE
EHC 82 (WHO, 1989). EHC review concludes that biological degradation is rapid, and consequently levels of cypermethrin and its degradation products in soil and surface waters are very low. Animals For studies of the biotransformation of cypermethrin in animal tissues, see Pestic. Sci., 1987, 21, 1 and ibid., 1990, 30, 159. Soil/Environment In soil, typical DT50 60 d (fine sandy loam); hydrolysis with cleavage of the ester bond occurs and also further hydrolytic and oxidative degradation; see T. R. Roberts & M. E. Standen, Pestic. Sci., 1977, 8, 305. Field dissipation is much faster. Koc 26 492-144 652; Kf 821-1042; not pH dependent. In river water, rapid degradation occurs, DT50 c. 5 d. DT50 for photochemical oxidative degradation in air 3.47 h.