5080. Iprovalicarb

Nomenclature

CAS number: 140923-17-7
[(1S)-2-Methyl-1-[[[1-(4-methylphenyl)ethyl]amino]carbonyl]propyl]carbamic acid 1-methylethyl ester; isopropyl-2-methyl-1-[(1-p-tolyethyl)carbamoyl]-(S)-propylcarbamate; N-(isopropyloxycarbonyl)-l-valine-4-methylphenylethylamide; SZX-722; Melody (Bayer CropSci.).
C18H28N2O3; mol wt 320.43.
C 67.47%, H 8.81%, N 8.74%, O 14.98%.

Description and references

Fungicide for use in food crops; commercial product is a mixture of two diastereomers (SS, SR). Prepn: T. Seitz et al., DE 4026966; eidem, US 5453531 (1992, 1995 both to Bayer). Comprehensive description: K. Stenzel et al., Brighton Crop Prot. Conf. - Pests Dis. 2, 367 (1998). Series of articles on prepn, structure, field studies, ecological profile and metabolism: Pflanzenschutz-Nachr. Bayer 52, 5-114 (1999). LC-MS determn: R. Brennecke ibid. 53, 5 (2000). ELISA method for residue detection: J. K. Lee et al., J. Agric. Food Chem. 52, 6680 (2004).

Chemical structure

Properties

White powder, mp 163-165° (mixture), 183° (SR), 199° (SS). d20 1.11. Log P (octanol/water): 3.2. Vapor pressure: 7.7 × 10-10 hPa (20°), 2.1 × 10-9 hPa (25°). LD50 in rats (mg/kg): >5000 orally; >5000 dermally; in bobwhite quail (mg/kg): >2000 orally. LC50 in rats (mg/m3): >4977 by inhalation (Stenzel).

Use

Fungicide.