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Pyriproxyfen

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IRAC 7C juvenile hormone mimic

 

NOMENCLATURE
Common name pyriproxyfène ((m) F-ISO); pyriproxyfen (BSI, E-ISO); no name (Sweden) IUPAC name 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether
Chemical Abstracts name 2-[1-methyl-2-(4-phenoxyphenoxy)ethoxy]pyridine 

CAS RN [95737–68–1]

EC no. 429–800–1 

Development codes S-9318; S-31183; S-71639 (all Sumitomo Chemical); V-71639 (Valent) Smiles code CC(COc1ccc(Oc2ccccc2)cc1)Oc3ccccn3 

PHYSICAL CHEMISTRY
Mol. wt. 321.4 M.f. C20H19NO3 Form White granular solid; (tech. is a pale yellow, waxy solid, with a faint odour). M.p. 47 °C V.p. <0.013 mPa (23 °C) Kow logP = 4.86 (pH 7) S.g./density 1.14 (20 °C) Solubility In hexane 400, methanol 200, xylene 500 (all in g/kg, 20–25 °C). F.p. 119 °C (Pensky-Martens closed test) 

APPLICATIONS
Biochemistry Acts as an insect juvenile hormone analogue that inhibits insect maturation processes. Mode of action Insect growth regulator; suppressor of embryogenesis, inhibitor of metamorphosis and inhibitor of reproduction. Uses Control of public health insect pests (flies, Beetles, midges, mosquitoes); applied to breeding sites (swamps, livestock houses, etc.). Also used for control of whitefly and thrips. Formulation types EC; GR; WG. 

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not an irritant to skin and eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >1300 mg/m3. NOEL (2 y) for rats 600 ppm (35.1 mg/kg b.w.) (EPA Tracking). ADI (JMPR) 0.1 mg/kg b.w. [1999, 2001]; (EC) 0.1 mg/kg b.w. [2008]; (EPA) 0.35 mg/kg b.w. [1999]. Water GV 0.3 mg/l (not to be used as a GV where added to water for public health purposes). Toxicity class WHO (a.i.) U. 

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks and bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5200 ppm. Fish LC50 (96 h) for rainbow trout >0.325 mg/l. Daphnia EC50 (48 h) 0.40 mg/l. Algae EC50 (72 h) for Selenastrum capricornutum 0.064 mg/l.