7765. Procymidone

Nomenclature

CAS number: 32809-16-8
3-(3,5-Dichlorophenyl)-1,5-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione; N-(3,5-dichlorophenyl)-1,2-dimethyl-1,2-cyclopropanedicarboximide; dicyclidine; S-7131; Sumisclex (Sumitomo); Sumilex (Sumitomo).
C13H11Cl2NO2; mol wt 284.14.
C 54.95%, H 3.90%, Cl 24.95%, N 4.93%, O 11.26%.

Description and references

Dicarboximide fungicide systemically active against Botrytis and Sclerotinia spp. on fruits and vegetables. Prepn: NL 7003836; A. Fujinami et al., US 3903090 (1970, 1975 both to Sumitomo). Antimicrobial spectrum and systemic activity: Y. Hisada et al., J. Pestic. Sci. 1, 145 (1976). Mechanism of action: A. C. Pappas, D. J. Fisher, Pestic. Sci. 10, 239 (1979). Field evaluation: I. F. Jackson, B. N. Smith, Proc. 32nd N.Z. Weed Pest Control Conf. 278 (1979). HPLC determn in wine musts and extracts: P. Cabras et al., J. Chromatogr. 256, 176 (1983). Review: N. Mikami, J. Miyamoto, Rev. Plant Prot. Res. 14, 85-95 (1981).

Chemical structure

Properties

Crystalline solid, mp 165-167°. d25 1.42-1.46. Vapor pressure: 1.32×10-4 mm Hg. uv max: 207.5, 275 nm (ε 4.2×104, 4.1×102). Soly in water (25°): 4.5 ppm. Highly sol in acetonitrile, acetone, ether, chloroform. Moderately sol in benzene, toluene. Stable in solvents. Unstable in alkaline media. LD50 in male rats (mg/kg): 6800 orally, >10000 dermally (Jackson). Also reported as LD50 in male, female rats (g/kg): 7.8, 9.1 orally (Mikami).

Use

Systemic agricultural fungicide.