Bifenthrin 联苯菊酯 氟氯菊酯

联苯菊酯

联苯菊酯对人畜毒性中等，对鱼毒性很高。对大鼠急性经口毒性LD50为54.5mg/kg；对兔急性经皮毒性LD50大于2000mg/kg。对皮肤和眼睛无刺激作用，无致畸、致癌、致突变作用。对鸟类低毒，对鹌鹑急性经口毒性LD50为1800mg/kg，对野鸭大于4450mg/kg。

国标编号 ----
CIPAC（数字代号）：736
CAS号：82657-04-3
中文名称 联苯菊酯
英文名称 bifenthrin；FMC-54800；Biphenthrin；Brigade；Capture；Talstar
别 名 氟氯菊酯；天王星；虫螨灵；毕芬宁；2-甲基联苯基-3-基甲基-(Z)-(1RS)-顺-3-(2-氯-3，3，3-三氟-1-丙烯基)-2，2-二甲基环丙烷羧酸酯
分子式 C23H22F3ClO2 外观与性状 纯品为固体，原药为浅褐色固体
分子量 422.86 蒸汽压 2.4×10-2Pa(25℃)
熔 点 68～70.6℃/纯品；57～64 ℃/原药 溶解性 水0.1mg/L ，丙酮1.25kg/L，并可溶于氯仿、二氯甲烷、乙醚、甲苯
密 度 相对密度(d25)1.210 稳定性 对光稳定，在酸性介质中也较稳定，在常温下贮存一年仍较稳定，但在碱性介质中会分解

危险标记 主要用途 为拟除虫菊酯类杀虫剂
对环境的影响
联苯菊酯对鱼毒性很高，对虹鳟LC50(96小时)为0.00015mg/L，水蚤LC50(48小时)0.00016mg/L。但由于该药剂在土壤中具有很高的亲合作用，且其水溶性又低，故实际影响较小。本剂对蜜蜂毒性中等，对家蚕高毒。 杀虫活性很高，主要为触杀和胃毒作用，无内吸和熏蒸活性。其作用迅速，持效期长，杀虫谱广。

联苯菊酯微乳剂研制开发
我国是茶的故乡，是茶叶生产和消费大国，茶园面积列世界第一，产量列世界第二位。然而近年来，欧盟对茶叶、水果、蔬菜等农残检测标准越来越严格，个别农药残留量指标比2000年以前提高了200倍，我国茶叶、水果、蔬菜等农产品在国际上的销售困难重重，去年我国茶叶不仅价格持续下跌，而且还频频遭欧盟和东南亚国家的绿色壁垒。影响茶叶、水果、蔬菜出口的主要原因是农药的不合理使用，果农、茶农的环保意识不强，大量、过量的使用甲胺磷等高毒有机磷农药，导致多种农产品农药残超标。
技术路线：2.5%联苯菊酯微乳剂是由联苯菊酯、助剂及水复配而成，通过室内毒力研究、化学配方筛选、田间药效试验，生产工艺设计、产品性能指标制定、三证办理等开发路线，完成项目产品开发过程。实现年产800吨的产业化生产规模。
性能指标：联苯菊酯（m/m）含量 ≥ 2.5%；PH值3.0～7.0；透明范围温度0～50℃；持久起泡性（1　min后）≤35 ml；乳液稳定性（用342ppm标准硬水稀释200倍）合格；热贮稳定性合格；低温稳定性合格，其它性能指标符合企业标准Q/TYN142-2005中的要求。
成果的创造性、先进性：①在剂型上选用了先进剂型——微乳剂，微乳剂是目前农药工业中最有发展前途的水基性剂型之一，制剂以水为溶剂，大大减少了有机溶剂对环境的污染压力；②本产品通过化工配方筛选试验、助剂筛选试验确定最稳定的产品配方，解决了联苯菊酯配制的水基性产品贮存时容易产生沉淀等质量问题，通过特殊助剂及分子结构的研究技术激发的项目产品的生物活性，从而成功的完成新型环保农药2.5%联苯菊酯微乳剂的研制开发及中试；③本项目是国内首创，技术水平达国内领先水平。

bifenthrin
Insecticide, acaricide
IRAC 3; pyrethroid

NOMENCLATURE
Common name bifenthrin (BSI, ANSI, draft E-ISO); bifenthrine ((f) draft F-ISO)
IUPAC name 2-methylbiphenyl-3-ylmethyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Roth: 2-methylbiphenyl-3-ylmethyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name (2-methyl[1,1'-biphenyl]-3-yl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [82657-04-3] Development codes FMC 54 800 Official codes OMS 3024

PHYSICAL CHEMISTRY
Composition Material contains ³97% cis- isomer, £3% trans- isomer. Mol. wt. 422.9 M.f. C23H22ClF3O2 Form Viscous liquid; crystalline or waxy solid. M.p. 68-70.6 °C V.p. 0.024 mPa (25 ºC) KOW logP >6 Henry 1.02 ´ 102 Pa m3 mol-1 (calc.) S.g./density 1.210 (25 ºC) Solubility In water <1 mg/l. Soluble in acetone, chloroform, dichloromethane, diethyl ether, and toluene. Slightly soluble in heptane and methanol. Stability Stable for 2 y at 25 ºC and 50 ºC (tech.). In natural daylight, DT50 255 d; stable 21 d at pH 5-9 (21 ºC). F.p. 165 ºC (Tag open cup); 151 ºC (Pensky-Martens closed cup)

COMMERCIALISATION
History Insecticide and acaricide reported by H. J. H. Doel et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1984, 49, 929) and A. R. Crossman et al. (ibid., p. 939). Introduced by FMC Corp. Manufacturers FMC; Sundat

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Contact and stomach action. Uses Effective against a broad range of foliar pests, including Coleoptera, Diptera, Heteroptera, Homoptera, Lepidoptera and Orthoptera; it also controls some species of Acarina. Crops include cereals, citrus, cotton, fruit, grapes, ornamentals and vegetables. Rates range from 5 g/ha against Aphididae in cereals to 45 g/ha against Aphididae and Lepidoptera in top fruit. Formulation types EC; GR; SC; UL; WP. Compatibility Not compatible with alkaline materials. Selected products: 'Talstar' (FMC)

OTHER PRODUCTS
'Aripyreth' (termites) (FMC, Nihon Nohyaku); 'Biflex' (FMC); 'Brigade' (FMC); 'Capture' (FMC); 'Semafor' (FMC); 'Starion' (FMC)

ANALYSIS
Product analysis by glc; hplc for analysis of isomer content. Residue analysis by glc with ECD (AOAC Methods, 17th Ed., 998.01). Details available from FMC Agricultural Chemicals Group. Analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 65, 67 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats 54.5 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritant to skin; virtually non-irritating to eyes (rabbits). No skin sensitisation (guinea pigs). NOEL (1 y) for dogs 1.5 mg/kg daily. Non-teratogenic in rats (£2 mg/kg daily) and rabbits (8 mg/kg daily). ADI (JMPR) 0.02 mg/kg [1992]. Toxicity class WHO (a.i.) II; EPA (formulation) II

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 1800, mallard ducks 2150 mg/kg. Dietary LC50 (8 d) for bobwhite quail 4450, mallard ducks 1280 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.00035, rainbow trout 0.00015 mg/l. Daphnia LC50 (48 h) 0.00016 mg/l. Low solubility in water and high affinity for soil contribute to produce little impact in aquatic systems under field conditions. Bees LD50 (oral) 0.1 mg/bee; (contact) 0.01462 mg/bee.

ENVIRONMENTAL FATE
Soil/Environment Soil DT50 65-125 d. Koc 1.31-3.02 ´ 105.