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Metalaxyl

Description References
Metalaxyl
Metalaxyl structure
CAS No.
57837-19-1
Chemical Name:
Metalaxyl
Synonyms
SPAN;Bleu;INFRA;APRON;TOKAT;MILOR;METAX;cg117;Fubol;Subdue
CBNumber:
CB4431035
Molecular Formula:
C15H21NO4
Formula Weight:
279.33
MOL File:
57837-19-1.mol

Metalaxyl Properties

Melting point:
72-73°C
Boiling point:
422.1°C (rough estimate)
Density 
1.1083 (rough estimate)
vapor pressure 
7.5 x 10-4 Pa (25 °C)
refractive index 
1.5130 (estimate)
Flash point:
100 °C
storage temp. 
APPROX 4°C
form 
neat
Water Solubility 
0.84 g/100 mL
BRN 
2947777
CAS DataBase Reference
57837-19-1(CAS DataBase Reference)
NIST Chemistry Reference
Dl-alanine, n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-, methyl ester(57837-19-1)
EPA Substance Registry System
Alanine, N-(2,6-dimethylphenyl)-N-( methoxyacetyl)-, methyl ester(57837-19-1)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H317-H412
Precautionary statements  P273-P280
Hazard Codes  Xn,F
Risk Statements  22-43-52/53-36-20/21/22-11
Safety Statements  13-24-37-46-61-36-26-16
RIDADR  UN 1648 3/PG 2
WGK Germany  2
RTECS  AY6910000
HS Code  29242990
Toxicity LD50 in rats (mg/kg): 669 orally (Urech)

Metalaxyl price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 32012 Metalaxyl PESTANAL 57837-19-1 100mg $51.2 2018-11-20 Buy
Sigma-Aldrich N12380 Metalaxyl analytical standard 57837-19-1 100mg $61.3 2018-11-20 Buy
Cayman Chemical 25817 Metalaxyl ≥98% 57837-19-1 250mg $76 2018-11-19 Buy
Cayman Chemical 25817 Metalaxyl ≥98% 57837-19-1 100mg $32 2018-11-19 Buy
Cayman Chemical 25817 Metalaxyl ≥98% 57837-19-1 500mg $144 2018-11-19 Buy

Metalaxyl Chemical Properties,Uses,Production

Description

Metalaxyl (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.

References

Kerkenaar, 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 Properties

Pale Beige Solid

Chemical Properties

Combustible, white crystalline solid or powder. Odorless.

Uses

Agricultural fungicide. Phenylamide fungicide or use in food crops, shrubs and turf.

Uses

Systemic fungicide used to control a variety of diseases on a wide range of temperate, subtropical and tropical crops.

Uses

Metalaxyl 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.

Hazard

Moderately toxic by ingestion.

Agricultural Uses

Fungicide: 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 name

AGROX® 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 Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Metalaxyl 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 Fate

Soil. 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 pathway

O-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.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

Metalaxyl 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.

Incompatibilities

Incompatible 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 Disposal

Small 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.

Metalaxyl Preparation Products And Raw materials

Raw materials

Preparation Products


Metalaxyl Suppliers

Global( 178)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan DaKen Chemical CO.,LTD.
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info@dakenchem.com CHINA 21676 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
career henan chemical co
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sales@coreychem.com CHINA 30001 58
Chemwill Asia Co.,Ltd.
86-21-51086038
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QUALITY CONTROL CHEMICALS INC.
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Hubei xin bonus chemical co. LTD
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027-59338440 sales@guangaobio.com CHINA 23049 58
BOC Sciences
1-631-619-7922
1-631-614-7828 inquiry@bocsci.com United States 20115 58
Chongqing Chemdad Co., Ltd
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View Lastest Price from Metalaxyl manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-20 Metalaxyl
57837-19-1
US $1.00 / KG 1KG 99% Customized career henan chemical co

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