Pesticides >> Insecticides >> Permethin

Permethrin

Permethrin 95%TC
Permethrin 50%E
Permethrin 10%EC

Insecticide
pyrethroid

NOMENCLATURE
Common name permethrin (BSI, E-ISO, ANSI, ESA, BAN); permethrine (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]) EEC no. 258-067-9 Development codes NRDC 143; FMC 33 297; PP557 (ICI); WL 43 479 (Shell); LE 79-519 Official codes OMS 1821

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). Formulation types DP; EC; UL; WG; WP; Fumigant; Aerosol. Compatibility Mixing with calcium nitrate is not recommended. Selected tradenames: 'Ambush' (crop protection) (Syngenta); 'Dragnet' (termiticide) (FMC); 'Dragon' (public health) (Syngenta); 'Eksmin' (Sumitomo); 'Kafil' (crop protection) (Syngenta); 'Outflank' (veterinary) (BASF); 'Pounce' (FMC); 'Talcord' (agronomic use) (BASF); 'Assithrin' (Frunol); 'Cliper' (Cequisa); 'Corsair' (Aventis); 'Perkill' (United Phosphorus); 'Permetiol' (Agriphar); 'Permit' (Agricultura Nacional, Sanonda); 'Pramex' (Aventis); 'Sanathrin' (Sanachem); mixtures: 'Chinethrin' (+ piperonyl butoxide+ tetramethrin) (Agro-Chemie); 'Coopex' (+ bioallethrin S-cyclopentenyl isomer) (Kwizda)

OTHER TRADENAMES
'Adion' (Sumitomo); 'Imperator' (Syngenta); 'Prelude' (Syngenta); 'Stockade' (veterinary) (BASF); 'Darmycel Agarifume Smoke Generator' (Sylvan); 'Perigen' (Aventis); 'Permanone' (Aventis); 'Permasect' (Mitchell Cotts, Parry); 'Persect' (Vapco); 'Pertec' (Tecomag); 'Qamlin' (Aventis); 'Tornade' (Aventis) mixtures: 'Aqua Reslin' (+ bioallethrin S-cyclopentenyl isomer) (Aventis); 'Duracide P' (+ piperonyl butoxide+ tetramethrin) (Endura); 'Neopybuthrin' (+ bioallethrin+ bioallethrin S-cyclopentenyl isomer) (Aventis); 'Phinco - T 22' (+ piperonyl butoxide+ tetramethrin) (Vapco); 'Sirene-CM' (+ codlemone) (IPM Technologies); 'Sirene-PBW' (+ gossyplure) (IPM Technologies); 'Turbair Grain Store Insecticide' (+ fenitrothion+ resmethrin) (Graincare) Discontinued names mixtures: 'Ars Red' * (+ metoxadiazone) (Sumitomo); 'Valsan' * (+ metoxadiazone) (Sumitomo); 'Wiperjet' * (+ metoxadiazone) (Sumitomo); 'Combinex' * (+ thiram) (Fargro)

ANALYSIS
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles. By glc with FID (CIPAC Handbook, 1985, 1C, 2172; AOAC Methods, 1995, 986.03; H. Swaine & M. J. Tandy, Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 103). Identity also by glc or hplc (CIPAC Handbook, 1994, F, 404). Residues determined by glc with ECD (idem, ibid.; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64, 733; Man. Pesticide Residue Anal., 1987, I, 6, S19; Anal. Methods Residues Pestic., 1988, Part I, M11). Permethrin isomers in drinking water by gc with ECD (AOAC Methods, 1995, 990.06).

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 86, 88 (see part 2 of the Bibliography). See also A. J. Gray & D. M. Soderlund, Chapt. 5 in "Insecticides". IARC ref. 53 class 3 Oral Oral LD50 values of permethrin depend on such factors as: carrier, cis/trans ratio of the sample, the test species, its sex, age and degree of fasting; values reported sometimes differ markedly. Values for a cis/trans ratio of c. 40:60 are: for rats 430-4000, mice 540-2690 mg/kg; with a 20:80 ratio, the LD50 is c. 6000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2500, rabbits >2000 mg/kg. Mild eye and skin irritant (rabbits). Moderate skin sensitiser. Inhalation LC50 (3 h) for mice and rats >685 mg/m3 air; (separate study gives >13 800 mg/m3). NOEL In 2 y feeding trials, rats receiving 100 mg/kg diet showed no ill-effects. ADI (JMPR) 0.05 mg/kg b.w. (for tech., with cis/trans ratios 25:75 to 40:60) [1999]. Water GV 20 mg/l (based on ADI). Other No mutagenic, teratogenic, or carcinogenic activity. Toxicity class WHO (a.i.) II; EPA (formulation) II ('Ambush'); III ('Outflank') EC hazard Xn; R22

ECOTOXICOLOGY
Birds Typical oral LD50 values for a cis/trans ratio of c. 40:60 are: for chickens >3000, mallard ducks >9800, Japanese quail >13 500 mg/kg. Fish LC50 (96 h) for rainbow trout 2.5 mg/l; (48 h) for rainbow trout 5.4, bluegill sunfish 1.8 mg/l. Daphnia LC50 (48 h) 0.6 mg/l. Bees Toxic to bees. LD50 (24 h) (oral) 0.098 mg/bee; (topical) 0.029 mg/bee.

ENVIRONMENTAL FATE
EHC 94 (WHO, 1990). EHC 94 concludes that permethrin is not likely to be a hazard to the environment when used as recommended. Animals In mammals, there is hydrolysis of the ester bond, hydroxylation, and elimination as the glucoside conjugate (M. Elliott et al., J. Agric. Food Chem., 1976, 24, 270; L. C. Gaughan et al., ibid., 1978, 26, 613). Soil/Environment In soil and water, degradation is rapid. DT50 in soil <38 d (pH 4.2-7.7, o.m. 1.3-51.3%) (R. L. Holmstead et. al., J. Agric. Food Chem., 1978, 26, 590).