Bifenthrin

Common name: bifenthrin; bifenthrine
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]

PHYSICAL CHEMISTRY
Composition: Material contains 97% 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: 1.02x102 Pa m3 mol-1 (calc.) S.g./density: 1.210 (25 ºC); Solubility: In water <1 g/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
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 a.i./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.

MAMMALIAN TOXICOLOGY
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: 0.02 mg/kg.
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) 0.1g/bee; (contact) 0.01462g/bee.

ENVIRONMENTAL FATE
Soil/Environment: Soil DT50 65-125 d. Koc 1.31-3.02x105.