Common name: S-bioallethrin
IUPAC name: (S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Alt: (S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (+)-trans-chrysanthemate
Roth: (S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R)-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Chemical Abstracts name: [1R-[1a(S*),3a]]-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other names: Esbiol; S-biothrin; esdepalléthrine
CAS RN: [28434-00-6]
EEC no.: 249-013-5
PHYSICAL CHEMISTRY
Composition: Esbiol contains 95% m/m total isomers, of which 90% is esdepalléthrine. the remainder being essentially the (R)-cyclopentenyl isomer, with <3% cis- isomers. Mol. wt.: 302.4; M.f.: C19H26O3; Form: Orange-yellow viscous liquid. M.p.: Not applicable; no crystallisation observed at -40 ºC. B.p.: 165-170 ºC/0.15 mmHg (OMS 3046); 163-170 ºC/0.15 mmHg (OMS 3045). V.p.: 44 mPa (25 ºC). S.g./density: 1.010 at 20 ºC. Solubility: Completely miscible with 100% ethanol, acetone, dichloromethane, di-isopropyl ether, toluene, n-hexane, chloroform, ethyl acetate, methanol, n-octanol, and petroleum solvent (20 ºC). Stability: Degraded by u.v. light. F.p.: 113 ºC (open cup).
APPLICATIONS
Mode of action: Non-residual insecticide with rapid knockdown action.
Uses: Esbiol is by far the most potent constituent of allethrin. OMS 3046 is used in aerosols, coils, electric vapourisers, or sprays indoors against flying and crawling insects (Blattodea, Culicidae, Muscidae). Also used in aerosols and sprays in mixtures with other pyrethroids and piperonyl butoxide. OMS 3045 has similar uses to OMS 3046.
Formulation types: AE; OL; UL; VP; Water-miscible liquid.
MAMMALIAN TOXICOLOGY
Oral: Acute oral LD50 Esbiol:- for male rats 784, female rats 1545 mg/kg. OMS 3045:- for male rats 432, female rats 378 mg/kg. OMS 3046:- for male rats 574.5, female rats 412.9 mg/kg (in PEG 200).
Skin and eye: Acute percutaneous LD50 for rabbits:- 1545 mg Esbiol/kg, >2000 mg OMS 3045/kg, >2000 mg OMS 3046/kg.
Inhalation: LC50 (4 h) for rats c. 1.26 mg Esbiol/l air, c. 2.63 mg OMS 3045/l air.
NOEL: Esbiol:- (0.5 y) for rats 1000 mg/kg diet. OMS 3045:- (2 y) for rats 500 ppm; not an oncogen up to 4500 mg/kg diet; (2 y) for mice 250 ppm; not an oncogen up to 1250 mg/kg diet; (1 y) for dogs 400 ppm.
Other: No mutagenic, carcinogenic, embryotoxic or teratogenic effects have been observed.
Toxicity class: WHO (a.i.) II; EPA (formulation) III
EC hazard: Xn; R20/22| N; R50, R53
ECOTOXICOLOGY
Birds: Acute oral LD50 for mallard ducks and bobwhite quail >5000 mg/kg; for chickens >5000 mg esdepalléthrine/kg. LC50 (8 d) for ducks and quail >5000 mg/kg diet.
Fish: LC50 (96 h) for rainbow trout 0.01, bluegill sunfish 0.033 mg/l. LC50 (96 h, static test) for fathead minnow 0.0800, yellow perch 0.0078 mg/l.
