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Metalaxyl

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Metalaxyl Basic information
Metalaxyl Chemical Properties
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  • Language:EnglishProvider:Apron
Metalaxyl Usage And Synthesis
  • DescriptionMetalaxyl (chemical name: methyl N-(methoxyacetyl)-N-(2, 6-xylyl)-DL-alaninate) is an acylalanine fungicide of systemic function. It can be used for the treatment of pythium and phytophthora in many kinds of vegetables and peas. However, there are severe problem of drug resistance in current days. Metalaxyl exhibits strong activity against the mycelial growth of various sensitive fungi such as pythium splendens. The primary effect of metalaxyl seems to be related to its effect of interfering with the normal synthesis of RNA and DNA in sensitive fungi strains.
  • ReferencesKerkenaar, A. "On the antifungal mode of action of metalaxyl, an inhibitor of nucleic acid synthesis in Pythium splendens." Pesticide Biochemistry & Physiology 16.1(1981):1-13.
    Fisher, David J., and A. L. Hayes. "Mode of action of the systemic fungicides furalaxyl, metalaxyl and ofurace." Pest Management Science13.3(2010):330-339.
    Davidse, L. C., et al. "A comparison between the antifungal mode of action of metalaxyl, cyprofuram, benalaxyl and oxadixyl in phenylamide-sensitivity and -resistant strains. " Crop Protection 7.6(1988):347-355.
    Metalaxyl showed the highest activity amongst the four fungicides against mycelial growth of sensitive strains on agar media.
  • Chemical PropertiesPale Beige Solid
  • Chemical PropertiesCombustible, white crystalline solid or powder. Odorless.
  • UsesAgricultural fungicide. Phenylamide fungicide or use in food crops, shrubs and turf.
  • UsesSystemic fungicide used to control a variety of diseases on a wide range of temperate, subtropical and tropical crops.
  • UsesMetalaxyl is used for the control of air-borne pathogens by foliar application and of soil-borne pathogens by soil application on a wide range of crops. It is particularly useful against Oomycetes including soil-borne Phytophthora diseases.
  • HazardModerately toxic by ingestion.
  • Agricultural UsesFungicide: Metalaxyl is used as a systemic fungicide on a variety of food and non-food crops including tobacco, turf and conifers, and ornamentals. Used in combination with fungicides of different mode of action as a foliar spray on tropical and subtropical crops; as a seed treatment to control downy mildew; and as a soil fumigant to control soilborne pathogens.
  • Trade nameAGROX® PREMIERE; ALLEGIENCE®; APRON®; CG 117®; CGA-48988®; CHLORAXYL®; COTGUARD®; EPERON®; DELTA-COAT; FOLIO® GOLD; GAUCHO®; KODIAK®; METALAXIL®; METAXANIN®; PACE®; PREVAIL®; RAXIL® (tebu- conazole + metalaxyl); RIDOMIL® GOLD/BRAVO®; RIDOMIL®; RIDOMIL 2E®; SUBDUE®
  • Safety ProfileModerately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.
  • Potential ExposureMetalaxyl is phenylamide systemic fungicide used on a variety of food and nonfood crops including tobacco, turf and conifers, and ornamentals. Used in combination with fungicides of different mode of action as a foliar spray on tropical and subtropical crops; as a seed treatment to control downy mildew; and as a soil fumigant to control soil-borne pathogens. Banned for use in EU.
  • Environmental FateSoil. Little information is available on the degradation of metalaxyl in soil; however, Sharom and Edgington (1986) reported metalaxyl acid as a possible metabolite. Repeated applications of metalaxyl decreases its persistence. Following an initial application, the average half-life was 28 days. After repeated applications, the half-life decreased to 14 days (Bailey and Coffey, 1985).
    Carsel et al. (1986) studied the persistence of metalaxyl in various soil types. The application rate was 2.2 kg/ha. In a fine sand, metalaxyl concentrations at soil depths of 15, 20, 45 and 60 cm were 100, 150, 100 and 75 ppb, respectively, 55 days after
    Plant. In plants, metalaxyl undergoes ring oxidation, methyl ester hydrolysis, ether cleavage, ring methyl hydroxylation and N-dealkylation (Owen and Donzel, 1986). Metalaxyl acid was identified as a hydrolysis product in both sunflower leaves an
    In pigeon peas, metalaxyl may persist up to 12 days (Indira et al., 1981; Chaube et al., 1984).
  • Metabolic pathwayO-Demethylation is one of the major routes of metalaxyl degradation in the plant cell suspension culture. Although hydroxylation of methyl groups in the phenyl ring predominates in both lettuce and grapes, species differences are evident in grapes, whereas N-dealkylation and aryl hydroxylation are less important in lettuce. Two isomeric metabolites of methyl hydroxylation and the hydroxylated metabolite of the phenyl ring are identified as fungus metabolites. By UV irradiation of metalaxyl in aqueous solution, two rearrangement products of the N-acyl group to the 4-position on the phenyl ring are identified.
  • ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
  • DegradationMetalaxyl is very stable in neutral and acidic media at room temperature and it is reasonably stable to aqueous photolysis. Its calculated half-lives in buffers at 25 °C below pH 7 are <3 years and at pH 9, 12 weeks. Only at pH 11 was measurable hydrolysis seen (half-life 1.6 days) (Melkebeke et al., 1986). Thus environmental degradation can be expected to be slow.
    [14C-phenyl]Metalaxy1ir radiated in aqueous solution with UV light at 30 °C was degraded with a half-life of 2-3 days at four pH values between 2.8 and 8.8. Acetone (1%) accelerated the rate of decomposition. Two rearrangement products (2 and 3) were isolated at pH 6.8; these accounted for 3 and 6% of the radioactivity, respectively. Irradiation of 2 showed that it was a precursor of compound 3 (Yao et al., 1989). Though these products appear to be unusual, there is a precedent for such reactions and the structures were determined by 1H and 13C NMR spectroscopy.
    Decomposition under simulated sunlight was slower with a half-life of 297 days (Pirisi et al., 1996). Amide bond cleavage and N-dealkylation to compounds 4 and 5 was reported. The dimethylaniline (6) was a putative product but a separate experiment showed that it was degraded at a higher rate than the parent and so was not observed from metalaxyl. The products are shown in Scheme 1.
  • IncompatibilitiesIncompatible with alkaline materials, strong acids, oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur).
  • Waste DisposalSmall amounts may be destroyed by alkaline hydrolysis. Admixture with alkali can be followed by soil burial. Larger quantities can be disposed of by incineration in admixture with acetone or xylene and using effluent gas scrubbing. Do not reuse empty container; proper disposal required.
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