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Iprodione

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NOMENCLATURE

Common name iprodione (BSI, E-ISO, (m) F-ISO, ANSI) IUPAC name 3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide
Chemical Abstracts name 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide Other names glycophene* (rejected common name proposal) CAS RN [36734–19–7] EC no. 253–178–9
PHYSICAL CHEMISTRY
Composition Tech. is ≥96% pure. Mol. wt. 330.2 M.f. C13H13Cl2N3O3 Form White, odourless, non-hygroscopic crystals or powder. M.p. 134 °C; (tech., 128–128.5 °C) V.p. 5 × 10-4 mPa (25 °C) Kow logP = 3.0 (pH 3 and 5) Henry 0.7 × 10-5 Pa m3 mol-1 (calc.) S.g./density 1.00 (20 °C); (tech., 1.434–1.435) Solubility In water 13 mg/l (20 °C). In n-octanol 10, acetonitrile 168, toluene 150, ethyl acetate 225, acetone 342, dichloromethane 450, hexane 0.59 (all in g/l, 20 °C). Stability Relatively stable in acid media, but decomposed in alkaline media. DT50 1–7 d (pH 7), <1 h (pH 9). Aqueous solutions are degraded by uv light, but are relatively stable in simulated sunlight.
APPLICATIONS
Biochemistry Affects mitogen-activated protein histidine kinase, in osmotic signal transduction. Mode of action Contact fungicide with protective and curative action. Inhibits germination of spores and growth of fungal mycelium. Uses Control of Botrytis, monilia, sclerotinia, Alternaria, Corticium, Fusarium, Tilletia, Pellicularia sasakii, Phoma, Rhizoctonia, Typhula spp., etc. Used mainly on sunflowers, cereals, fruit trees, berry fruit, oilseed rape, rice, cotton, vegetables and vines as a foliar spray, at 0.5–1.0 kg/ha, and on turf, at 3–12 kg/ha. Can also be used as a post-harvest dip, as a seed treatment, or as a dip or spray at planting. Formulation types DP; EC; FS; SC; SU; WG; WP.
ENVIRONMENTAL FATE
Animals In rats, ruminants and birds, iprodione is rapidly eliminated. It also undergoes extensive metabolism, by hydrolysis and rearrangement reactions. Plants Metabolism studies in cereals, fruit, leafy and oily crops showed that iprodione is the dominant component of the total residue resulting from foliar application. Soil/Environment Rapidly metabolised in soil, with formation of CO2. DT50 (lab.) 20–80 d; (field) 919 d. Koc 202–543. Rate of degradation increases with successive treatments, hence accumulation does not occur.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >5.16 mg/l air. NOEL (2 y) for rats 150 mg/kg diet; (1 y) for dogs 18 mg/kg b.w. ADI (JMPR) 0.06 mg/kg b.w. [1995]; (EC) 0.06 mg/kg b.w. [2003]; (EPA) aRfD 0.06, cRfD 0.02 mg/kg b.w. [1998]. Toxicity class WHO (a.i.) U EPA (formulation) III EC classification R40| N; R50, R53 
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000, mallard ducks >10 400 mg/kg. Fish LC50 (96 h) for rainbow trout 4.1, bluegill sunfish 3.7 mg/l. Daphnia EC50 (48 h) 0.7 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 1.9 mg/l. Bees Contact LD50 >0.4 mg/bee. Worms LC50 for earthworms >1000 mg/kg soil. Other beneficial spp. Harmless to non-target arthropods.