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Metalaxyl(CAS No. 57837-19-1)

Metalaxyl C15H21NO4 (cas 57837-19-1) Molecular Structure

57837-19-1 Structure

Identification and Related Records

【CAS Registry number】
N-(2,6-Dimethylphenyl)-N-(methoxy acetyl)-alanine methyl ester
methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate
【Molecular Formula】
C15H21NO4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

1.117 g/cm3
【Melting Point】
【Boiling Point】
394.3 °C at 760 mmHg
【Refractive Index】
【Flash Point】
192.3 °C
0.84 g/100 mL
0.84 g/100 mL in water
Fine, white powder
... Colorless crystals ... .
Stable at normal temperatures and pressures.
【Storage temp】
【Computed Properties】
Molecular Weight:279.33154 [g/mol]
Molecular Formula:C15H21NO4
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:6
Exact Mass:279.147058
MonoIsotopic Mass:279.147058
Topological Polar Surface Area:55.8
Heavy Atom Count:20
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Ring Count:1
Effective Rotor Count:7
Conformer Sampling RMSD:0.8
CID Conformer Count:47

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Hazard Codes:?HarmfulXn,FlammableF
Risk Statements: 22-43-52/53-36-20/21/22-11
R22:Harmful if swallowed.?
R43:May cause sensitization by skin contact.?
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements: 13-24-37-46-61-36-26-16?
S13:Keep away from food, drink and animal foodstuffs.?
S24:Avoid contact with skin.?
S37:Wear suitable gloves.?
S46:If swallowed, seek medical advice immediately and show this container or label.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S16:Keep away from sources of ignition.
RIDADR: UN 1648 3/PG 2
RTECS: AY6910000
Hazardous Substances Data 57837-19-1(Hazardous Substances Data)
Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.

UN 1648
Emulsifiable concentrate, granule, flowable & wettable powder.
USEPA/OPP Pesticide Code: 113501; Trade Names: Ridomil; Ridomil MZ, component of (with 014504); CGA-48988; Subdue; Apron.
Trade names: ... Fubol, Acylon.

??Metalaxyl ,? its cas register number is 57837-19-1. It also can be called?Allegiance ; Apron ; Apron SD 35 ; Caswell No. 375AA ; D,L-N-(2,6-Dimethylphenyl)-N-(2'-methoxyacetyl)alaninate de methyle ; Metalaxil ; Metanaxin ; Methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate ; N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester ; Ridomil ;
?Subdue .

【Octanol/Water Partition Coefficient】
log Kow = 1.65
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Metalaxyl is produced by reaction of 2,6-dimethylaniline with an excess of methyl 2-bromopropionate in the presence of sodium bicarbonate, followed by acetylation with methoxyacetyl chloride.
Prepn: A. Hubele, DE 2515091 corresp to US 4151299 (1975, 1979 to Ciba-Geigy).

Agricultural fungicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
【Biomedical Effects and Toxicity】
In a single dose study, male & female rats were administed 0.5 or 25 mg/kg of metalaxyl by gavage. Over 60% of the low or high dose was excreted within 24 hr in urine or feces. Negligible amounts were eliminated in expired air. Low tissue residues 6 days after treatment indicated no appreciable bioaccumulation. Female rats eliminated the majority of the dose (55-65%) in urine, & males eliminated most (60-70%) in feces. Although metabolites were not identified, the chromatographic pattern was similar for both sexes & doses.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 30 to 284(2) indicate that metalaxyl is expected to have very high to moderate mobility in soil(SRC). Volatilization of metalaxyl from moist soil surfaces is not expected to be an important fate process(3) given an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.62X10-6 mm Hg(4), and water solubility, 8,400 mg/l(4). Metalaxyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Metalaxyl undergoes fairly rapid degradation (half-life of approx 40 days) in soils incubated aerobically(5). Experiments with 14C-metalaxyl demonstrated that it was readily metabolized in soil with a history of fungicide treatment (half-life of 14 days) but not in a control soil(6). In a tobacco soil, rapid degradation of metalaxyl occurred with a half-life of 6 days(7). The main breakdown product of metalaxyl in soil was the acid metabolite(7).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 30 to 284(2), indicates that metalaxyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.62X10-6 mm Hg(4), and water solubility, 8,400 mg/l(4). According to a classification scheme(5), an estimated BCF of 4(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Photolysis of metalaxyl in aqueous solution using UV light with wavelengths greater than 290 nm resulted in 10% substrate transformation in 3 hours(8). Long time (65 hr) irradiation under artificial sunlight in the presence of humic acids resulted in 65% degradation of the chemical(8). Photolysis leads not only to rearrangement of the N-acyl group to the aromatic ring but also to demethoxylation, N-deacylation, and elimination of the methoxycarbonyl group from the molecule(8). Based on biodegradation studies in soil, metalaxyl is expected to biodegrade in aqueous systems(SRC). Metalaxyl undergoes fairly rapid degradation (half-life of approx 40 days) in soils incubated aerobically(9). Experiments with 14C-metalaxyl demonstrated that its was readily metabolized in soil with a history of fungicide treatment (half-life of 14 days) but not in a control soil(10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metalaxyl, which has a vapor pressure of 5.62X10-6 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase metalaxyl is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from its rate constant of 27X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase metalaxyl may be removed from the air by wet and dry deposition(SRC). Metalaxyl undergoes photolysis in water(4) and, by analogy, may undergo direct photolysis in the atmosphere(SRC).

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