Metalaxyl

Base Information

• Chemical Name: Metalaxyl
• CAS No.: 57837-19-1
• Deprecated CAS: 102256-63-3,1135441-62-1
• Molecular Formula: C15H21NO4
• Molecular Weight: 279.336
• Hs Code.: 29242990
• European Community (EC) Number: 260-979-7
• UNII: 16K4M187IF
• DSSTox Substance ID: DTXSID6024175
• Nikkaji Number: J92.425C
• Wikipedia: Metalaxyl
• Wikidata: Q4778002
• Metabolomics Workbench ID: 143631
• ChEMBL ID: CHEMBL105809
• Mol file: 57837-19-1.mol

Synonyms:Acylon;metalaxyl;methyl-DL-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alaninate;R-metalaxyl;Rac-metalaxyl;Ridomil;Ridomil, (L-Ala)-isomer

Chemical Property of Metalaxyl

Chemical Property:

• Appearance/Colour: Colorless, odorless crystal
• Vapor Pressure: 2E-06mmHg at 25°C
• Melting Point: 72-73 °C
• Refractive Index: 1.527
• Boiling Point: 394.3 °C at 760 mmHg
• PKA: 1.41±0.50(Predicted)
• Flash Point: 192.3 °C
• PSA: 55.84000
• Density: 1.117 g/cm³
• LogP: 1.84430
• Storage Temp.: APPROX 4°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 0.84 g/100 mL
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 335

Purity/Quality:

98% ^*data from raw suppliers

Metalaxyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F
• Hazard Codes: Xn,F
• Statements: 22-43-52/53-36-20/21/22-11
• Safety Statements: 13-24-37-46-61-36-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC
• 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. As an important fungicide group, acylanilides have a longer history than triazoles. Metalaxyl (44) is one of the most important fungicides in the group. It originates from the class of herbicidal chloroacetanilides, particularly metolachlor (45). Metolachlor, having a chiral carbon center and a chiral axis, is composed of four stereoisomers, the most herbicidally active one of which is the (αR, 1S)-isomer (32). For the stereoselective synthesis of this isomer, novel iridium-ferrocenyldiphosphine catalysts for the enantioselective hydrogenation of N-(2-ethyl-6-methylphenyl)- N-(1 -methoxymethyl)-ethylidene-amine are reported. In the most effective approach, the catalyst is generated in situ from [Ir(cod)Cl]2(cod = cyclooctadiene) and the ferrocenyldiphosphine ligand (R)-(S)-PPF-P(3,5-xyl)2 (46) (33).When the substrate to catalyst ratio is 106, the conversion is complete in 2 to 3 h, producing metolachlor in optical yields over 80% (34).
• Uses: Systemic fungicide used to control a variety of diseases on a wide range of temperate, subtropical and tropical crops. 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. Agricultural fungicide. Phenylamide fungicide or use in food crops, shrubs and turf.

Technology Process of Metalaxyl

There total 18 articles about Metalaxyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Methoxyacetyl chloride (38870-89-2) + methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate (57646-33-0) → methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (57837-19-1,69516-34-3,70630-17-0)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.01.033

Reference yield: 88.2%

Methoxyacetyl chloride (38870-89-2) + methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate (57646-33-0) → methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (57837-19-1)

Guidance literature:

In toluene; for 2.5h; Reflux;

Reference yield:

Methyl 2-bromopropionate (5445-17-0) + N-(1-methoxyacetyl)-2,6-dimethylaniline (53823-88-4) → N-methoxyacetyl-2,6-dimethylaniline sodium salt + methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (57837-19-1)

Guidance literature:

With sodium methylate; In 5,5-dimethyl-1,3-cyclohexadiene;

upstream raw materials:

methanol

methyl 2-[N-(2,6-dimethylphenyl)-N-(chloroacetyl)-amino]-propionate

Methoxyacetyl chloride

methyl N-(2,6-dimethylphenyl)alaninate

Downstream raw materials:

rac-2-[(2,6-dimethylphenyl)methoxyacetylamino]propionic acid

methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate

[N-(2,6-dimethylphenyl)-2-hydroxyacetamido]isopropanoate methyl ester

mercury(II)chloride*methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate

Refernces

• 1、 -. "Synthesis method of optically active metalaxyl". Paragraph 0031; 0036; 0037; 0041; 0046; 0047; 0051; 0056. . Retrieved 2019/01/21.
• 2、 Zhang, Xiaoli,Wang, Litao,Dong, Shuqing,Zhang, Xia,Wu, Qi,Zhao, Liang,Shi, Yanping. "Nanocellulose derivative/silica hybrid core-shell chiral stationary phase: Preparation and enantioseparation performance". . . Retrieved 2016/06/15.