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Metalaxyl-M

Metalaxyl-M 90%TC
Metalaxyl-M 48%EC

Fungicide

FRAC 4; phenylamide: acylalanine

NOMENCLATURE

Common namemetalaxyl-M (BSI, E-ISO, (m) F-ISO)

IUPAC namemethyl N-(methoxyacetyl)-N-(2,6-xylyl)-D-alaninate; methyl (R)-2-{[(2,6-dimethylphenyl)methoxyacetyl]amino}propionate

Chemical Abstracts namemethyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate

Other namesR-metalaxyl; CGA 76539; mefenoxamCAS RN[70630-17-0]Development codesCGA 329351 (Ciba-Geigy)

Metalaxyl-M PHYSICAL CHEMISTRY

Composition(R)- enantiomer of metalaxyl.Mol. wt.279.3M.f.C15H21NO4FormPale yellow to light brown, viscous liquid.M.p.-38.7 °C (glass transition temperature)B.p.Decomp. c. 270 °CV.p.3.3 mPa (25 °C)KOWlogP = 1.71 (25 °C)Henry3.5 ´ 10-5Pa m3mol-1(calc.)S.g./density1.125 (20 °C)SolubilityIn water 26 g/l (25 °C). In n-hexane 59 g/l; miscible with acetone, ethyl acetate, methanol, dichloromethane, toluene, n-octanol.StabilityHydrolytically stable under acidic and neutral conditions (DT50>200 d). Under alkaline conditions, DT50116 d (pH 9, 25 °C).Specific rotationNegativeF.p.179 °C (EEC A10)

Metalaxyl-M COMMERCIALISATION

HistoryReported by C. Nuninger et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1996, 1, 41). Developed by Ciba-Geigy AG (now Syngenta AG) and introduced in the US in 1996.PatentsPCT Patent appl. WO96/01559; ZA-P.95/5708ManufacturersSyngenta

Metalaxyl-M APPLICATIONS

Metalaxyl-M OTHER TRADENAMES

'SL 567A' (Syngenta) mixtures:'Epok' (+ fluazinam) (Syngenta); 'Folio Gold' (+ chlorothalonil) (Syngenta); 'Fubol Gold' (+ mancozeb) (Syngenta); 'Helix' (+ difenoconazole+ fludioxonil+ thiamethoxam) (Syngenta); 'Ridomil Gold Combi' (+ folpet) (Syngenta); 'Ridomil Gold Copper' (+ copper hydroxide) (Syngenta); 'Ridomil Gold MZ' (+ mancozeb) (Syngenta); 'Ridomil Gold PC' (+ quintozene) (Syngenta); 'Ridomil Gold Plus' (+ copper oxychloride) (Syngenta); 'WAKIL XL' (+ cymoxanil+ fludioxonil) (Syngenta)

MAMMALIAN TOXICOLOGY

OralAcute oral LD50for rats 667 mg/kg.Skin and eyeAcute percutaneous LD50for rats >2000 mg/kg. Not a skin irritant (rabbits); risk of serious damage to eyes (rabbits). Not a skin sensitiser (guinea pigs).InhalationLC50(4 h) for rats >2290 mg/m3.NOELfor rats 2.5, mice 35.7, dogs 8.0 mg/kg b.w. daily.ADI0.025 mg/kg b.w.OtherNot oncogenic, not mutagenic, not teratogenic.Toxicity classWHO (a.i.) IIEC hazard(Xn; R22, R41)

Metalaxyl-M ECOTOXICOLOGY
BirdsLD50(14 d) for bobwhite quail 981-1419 mg/kg. LC50(8 d) for bobwhite quail >5620 mg/kg.FishLC50(96 h) for rainbow trout >100 mg/l.DaphniaLC50(48 h) >100 mg/l.AlgaeErC50(72 h) for Scenedesmus subspicatus 103 mg/l.Other aquatic spp.EC50(96 h) for Eastern oyster (Crassostrea virginica) 9.7 mg/l.BeesLD50(48 h, contact) 25 mg/bee.WormsLC50(14 d) for Eisenia foetida 830 mg/kg soil.Other beneficial spp.EC formulation (480 g/l ) harmless to Poecilus cupreus and Orius insidiosus (IOBC).