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]  EEC no. 253-178-9  Development codes 26 019 RP (Rhône-Poulenc) 

PHYSICAL CHEMISTRY

Composition Tech. is ³96% pure.  Mol. wt. 330.2  M.f. C₁₃H₁₃Cl₂N₃O₃  Form White, odourless, non-hygroscopic crystals or powder.  M.p. 134 ºC; (tech., 128-128.5 ºC)  V.p. 5 ´ 10^-4 mPa (25 ºC)  K_OW logP = 3.0 (pH 3 and 5)  S.g./density 1.00 (20 ºC); (tech., 1.434-1.435)  Solubility In water 13 mg/l (20 ºC). In n-octanol 10, acetonitrile 168, toluene 150, ethyl acetate 225, acetone 342, dichloromethane 450, hexane 0.59 (all in g/l, 20 ºC).  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 u.v. light, but are relatively stable in simulated sunlight. 

APPLICATIONS

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, Helminthosporium, 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 a.i./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. 

ANALYSIS

Product analysis by hplc or glc (CIPAC Handbook, 1995, G, 98-104; L. Lacroix et al., Anal. Methods Pestic. Plant Growth Regul., 1980, 11, 247). Residues determined by glc with ECD (idem, ibid.; Man. Pestic. Residue Anal., 1987, I, 6, S8, S19; Anal. Methods Residues Pestic., 1988, Part I, M1, M12).

MAMMALIAN TOXICOLOGY

Reviews FAO/WHO 74, 76 (see part 2 of the Bibliography).  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].  Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) IV 

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 LC₅₀ (48 h) 0.25 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.

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) 20-160 d. K_oc 373 to 1551. Rate of degradation increases with successive treatments, hence accumulation does not occur.