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Metalaxyl

Metalaxyl 95%TC
Metalaxyl 35%WP
Metalaxyl 25%EC

Fungicide
FRAC 4, A1; phenylamide: acylalanine

Metalaxyl NOMENCLATURE
Common name metalaxyl (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate; methyl 2-{[(2,6-dimethylphenyl)methoxyacetyl]amino}propionate
Chemical Abstracts name methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate
CAS RN [57837-19-1] EEC no. 260-979-7 Development codes CGA 48 988 (Ciba-Geigy)

Metalaxyl PHYSICAL CHEMISTRY
Mol. wt. 279.3 M.f. C15H21NO4 Form Fine, white powder. M.p. Tech. 63.5-72.3 ºC B.p. 295.9 °C/101 kPa V.p. 0.75 mPa (25 ºC) KOW logP = 1.75 (25 ºC) Henry 1.6  10-5 Pa m3 mol-1 (calc.) S.g./density 1.20 at 20 ºC Solubility In water 8.4 g/l (22 ºC). In ethanol 400, acetone 450, toluene 340, n-hexane 11, n-octanol 68 (all in g/l, 25 ºC). Stability Stable up to 300 ºC. Stable in neutral and acidic media at room temperature; on hydrolysis, DT50 (calc.) (20 ºC) >200 d (pH 1), 115 d (pH 9), 12 d (pH 10). pKa <<0

COMMERCIALISATION
History Fungicide reported by F. J. Schwinn et al. (Mitt. Biol. Bundesanst. Land-Fortswirtsch. Berlin-Dahlem, 1977, 178, 145) and by P. A. Urech (Proc. 1977 Br. Crop. Prot. Conf. - Pests Dis., 1977, 2, 623). Introduced by Ciba-Geigy AG (now Syngenta AG) and first marketed in 1979. Patents BE 827671; GB 1500581; US 4151299 Manufacturers Agrochem; Jingma; Rallis; Sharda; Syngenta

Metalaxyl APPLICATIONS
Biochemistry Inhibits protein synthesis in fungi, by interference with the synthesis of ribosomal RNA. Mode of action Systemic fungicide with protective and curative action, absorbed through the leaves, stems, and roots. Uses To control diseases caused by air- and soil- borne Peronosporales on a wide range of temperate, subtropical and tropical crops. Foliar sprays with mixtures of metalaxyl and protectant fungicides are recommended to control air-borne diseases caused by Pseudoperonospora humuli on hops, Phytophthora infestans on potatoes and tomatoes, Peronospora tabacina on tobacco, Plasmopara viticola on vines, Bremia lactucae on lettuce, and downy mildews on various vegetables, at 200-300 g/ha. Soil applications of metalaxyl alone are used to control soil-borne pathogens causing root and lower stem rots on avocado and citrus, at 500-1500 g/ha. Seed treatments control systemic Peronosporaceae on maize, peas, sorghum and sunflowers, as well as damping-off (Pythium spp.) of various crops. Formulation types DS; FS; GR; WP. Selected products: 'Ridomil' (Syngenta); 'Duet' (Devidayal); 'Metamix' (Agrimix); 'Vacomil-5' (Vapco); 'Vilaxyl' (Vipesco); mixtures: 'Maxim' (+ fludioxonil) (seed treatment) (Syngenta); 'Hawaii' (+ mancozeb) (Rocca); 'Milor' (+ mancozeb) (Rotam); 'System 3' (+ quintozene+ Bacillus subtilis) (Crompton, Helena); 'Talman-combi' (+ mancozeb) (Cequisa)