5922. Metalaxyl

Nomenclature

CAS number: 57837-19-1
N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-dl-alanine methyl ester; methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-dl-alaninate; metaxanin; CGA-48988; Ridomil (Syngenta).
C15H21NO4; mol wt 279.33.
C 64.50%, H 7.58%, N 5.01%, O 22.91%.

Description and references

Phenylamide fungicide for use in food crops, shrubs and turf. Prepn: A. Hubele, DE 2515091; idem, US 4151299 (1975, 1979 to Ciba-Geigy). Comprehensive description: P. A. Urech, F. J. Schwinn, Phytiatr.-Phytopharm. 27, 239-247 (1978). Antifungal spectrum: A. Kerkenaar, A. K. Sijpesteijn, Pestic. Biochem. Physiol. 15, 71 (1981). Enzyme-linked immunosorbent assay of residues in foods: W. H. Newsome, J. Agric. Food Chem. 33, 528 (1985).

Chemical structure

Properties

Whitish crystals, mp 71-72°. Vapor pressure (20°): 2.2 × 106 mm Hg. Soly in water (20°): 7.1 g/l. Readily sol in most organic solvents. LD50 in rats (mg/kg): 669 orally (Urech).

Derivative

R-form.

Nomenclature

CAS number: 70630-17-0
N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-d-alanine methyl ester; (R)-[(2,6-dimethylphenyl)methoxyacetylamino]propionic acid methyl ester; metalaxyl-M; mefenoxam; CGA-329351; Apron (Syngenta); Ridomil Gold (Syngenta); Subdue (Syngenta).

Description and references

Enantioselective prepn: H.-U. Blaser, F. Spindler, Top. Catal. 4, 275 (1997). Comprehensive description: C. Nuninger et al., Brighton Crop Prot. Conf. - Pests Dis. 1996, 41-46.

Properties

Pale yellow to light brown viscous liquid. dec ≈270°. Log P (n-octanol/water): 1.71. Soly in water (25°): 26 g/l.

Use

Agricultural fungicide.