3222. Dimethomorph

Nomenclature

CAS number: 110488-70-5
4-[3-(4-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]morpholine; 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) acrylic acid morpholide; CME-151; Acrobat (BASF); Forum (BASF).
C21H22ClNO4; mol wt 387.86.
C 65.03%, H 5.72%, Cl 9.14%, N 3.61%, O 16.50%.

Description and references

Antifungal cinnamic acid derivative; comprised of a mixture of E- and Z- isomers. Process for prepn: J. Curtze, EP 294907; idem, US 4933449 (1988, 1990 both to Shell Int.). Comprehensive description: G. Albert et al., Brighton Crop Prot. Conf. - Pests Dis. 1988, 17-24. Mechanism of action study: P. J. Kuhn et al., Mycol. Res. 95, 333 (1991). Efficacy vs downy mildew of grapevines: T. Wicks, B. Hall, Plant Dis. 74, 114 (1990). Toxicological evaluation: G. E. Veenstra, D. E. Owen, Arch. Toxicol. 1992, Suppl 15, 113.

Chemical structure

Properties

Colorless, odorless, crystalline solid. mp 127-148°. Soly (g/l) at 25°: water <0.05, acetone 50, toluene 20, methanol 20, dichloromethane 500. LD50 in rats (mg/kg): 321 i.p.; 3900 orally; >5000 dermally; LC50 (4-hr inhalation): >4.2 mg/ml (Veenstra, Owen).

Use

Agricultural fungicide.