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Common name permethrin (BSI, E-ISO, ANSI, ESA, BAN); perméthrine (F-ISO); no name (Eire, Bangladesh)
IUPAC name 3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Roth: 3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [52645-53-1], (formerly [57608-04-5] and [63364-00-1])
PHYSICAL CHEMISTRY
Mol. wt. 391.3 M.f. C21H20Cl2O3 Form Tech. is a yellow-brown to brown liquid, which sometimes tends to crystallise partly at room temperature. M.p. 34-35 ºC; cis- isomers 63-65 ºC; trans- 44-47 ºC B.p. 200 ºC/0.1 mmHg; >290 ºC/760 mmHg V.p. cis- 0.0025 mPa; trans- 0.0015 mPa (both 20 ºC) (D. Wells et al., Pestic. Sci., 1986, 17,473) KOW logP = 6.1 (20 ºC) S.g./density 1.29 (20 °C) Solubility In water 6 ´ 10-3 mg/l (pH 7, 20 ºC). In xylene, hexane >1000, methanol 258 (all in g/kg, 25 ºC). Stability Stable to heat (³2 y at 50 ºC), more stable in acidic than alkaline media with optimum stability c. pH 4; DT50 50 d (pH 9), stable (pH 5, 7) (all 25 °C). Some photochemical degradation observed in laboratory studies, but field data indicate this does not adversely affect biological performance. F.p. >100 ºC ('Perigen')
APPLICATIONS
Mode of action Non-systemic insecticide with contact and stomach action, having a slight repellent effect.
Uses A contact insecticide effective against a broad range of pests. It controls leaf- and fruit-eating Lepidoptera and Coleoptera in cotton, at 100-150 g a.i./ha, in fruit, at 25-50 g/ha, in tobacco, vines and other crops, at 50-200 g/ha, and in vegetables, at 40-70 g/ha. It has good residual activity on treated plants. It is effective against a wide range of animal ectoparasites, provides >60 d residual control of biting flies in animal housing, at 200 mg a.i. (as EC)/m2 wall or 30 mg a.i. (as WP)/m2 wall, and is effective as a wool preservative, at 200 mg/kg wool. It provides >120 d control of Blattodea, Diptera, Hymenoptera and other crawling insects, at 100 mg a.i. (as WP)/m2, also flying insects.
Phytotoxicity Non-phytotoxic when used as directed (except that some ornamentals may be injured).