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Insecticide, acaricide Bifenthrin
NOMENCLATURE Bifenthrin
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 Bifenthrin
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)
APPLICATIONS Bifenthrin
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 tradenames: 'Talstar' (FMC)
MAMMALIAN TOXICOLOGY Bifenthrin
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 Bifenthrin
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 Bifenthrin
Soil/Environment Soil DT50 65-125 d. Koc 1.31-3.02 ´ 105. |
