Metalaxyl

TC & FORMULATION: 90%TC, 25%WP, 35%WP, 50%WP

Structure Formula

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

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 

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.

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