70630-17-0

Basic information

• Product Name: Metalaxyl-M
• Synonyms: METALAXYL-M;MEFENOXAM;APRON XL;RIDOMIL GOLD;D-Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl ester;(R)-2-{(2,6-Dimethylphenylmethoxy)acetylamino}-propionic acid methyl ester;N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester;metalaxyl-M (ISO) mefenoxam (R)-2-[(2,6-dimethylphenyl)-methoxyacetylamino]propionic acid methyl ester
• CAS NO: 70630-17-0
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Mol File: 70630-17-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: -38.6°C
• Boiling Point: 422.1°C (rough estimate)
• Flash Point: 192.3 °C
• Appearance: /
• Density: 1.1083 (rough estimate)
• Vapor Pressure: 2E-06mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: 0-6°C
• PKA: 1.41±0.50(Predicted)
• CAS DataBase Reference: Metalaxyl-M(CAS DataBase Reference)
• NIST Chemistry Reference: Metalaxyl-M(70630-17-0)
• EPA Substance Registry System: Metalaxyl-M(70630-17-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39-46
• WGK Germany: 3
• Hazardous Substances Data: 70630-17-0(Hazardous Substances Data)

Usage

Description

Metalaxyl-M is the more active of the two enantiomers of the phenylamide fungicide metalaxyl; metalaxyl is currently registered in more than 80 countries with uses on more than 60 crops. 1996 Mefenoxam (metalaxyl-M) first registered for use in NYS. Metalaxyl-M is the first enantiomeric form of a fungicide introduced into the market. When used as seed-treatment, soil treatment or foliar application against fungi of the order Peronosporales, it provides the same excellent level of efficacy as metalaxyl but at half the application rate. Mefenoxam is more commonly used than metalaxyl in most pesticide products registered in NYS today.

Uses

Metalaxyl-M is an isomer of Metalaxyl (M258740), an agricultural fungicide. Phenylamide fungicide or use in food crops, shrubs and turf.

Definition

ChEBI: Metalaxyl-M is a methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate that is the more active R-enantiomer of metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops. It has a role as an agrochemical. It is a methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate, a D-alanine derivative, an acylamino acid fungicide and an anilide fungicide. It derives from a D-alanine. It is an enantiomer of a (S)-metalaxyl.

Toxicity evaluation

Metalaxyl-M is the R-enantiomer-enriched (97%) form of metalaxyl. This compound is a phenylamide that disrupts fungal RNA polymerase, and the R-enantiomer is much more active. The rat oral LD50 is 670 mg/kg for both formulations. Metalaxyl-M is a severe ocular irritant, but otherwise is toxicologically equivalent to metalaxyl. Both are non-irritating and non-sensitizing for skin. Rats in repeated-dose studies with metalaxyl-M developed centrilobular hepatocellular hypertrophy. In dogs treated daily for 2 years with up to 80 mg metalaxyl/kg, highdose dogs showed transient spasms and salivation, especially during the first year, and four high-dose dogs died between study weeks 20 and 52. Histopathological liver changes were not detected in the dogs despite increased liver weights as well as elevated serum alanine aminotransferase (ALT) and alkaline phosphatase (ALP) activities. Two-year rodent studies showed a small increase in hepatocellular fatty change and centrilobular hypertrophy, but no increase in neoplasia. Metalaxyl is also negative for reproductive and developmental effects, and the great majority of genotoxicity tests have been negative.

Mode of action

Metalaxyl-M controls all economically important diseases caused by fungi in the order Peronosporales. Thiamethoxam, metalaxyl-M and difenoconazole act systemically in seeds and young plants. They are taken up from the treated seed coat and translocated to all parts of the plant during germination.

InChI:InChI=1/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3/t12-/m1/s1

Upstream product

• 38870-89-2 Methoxyacetyl chloride 
• 52888-49-0 methyl N-(2,6-dimethylphenyl)alaninate 
• 57646-33-0 methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate 
• 712327-18-9 2-ethoxyethyl N-(2,6-dimethylphenyl)alaninate 
• 67617-64-5 N-(2,6-dimethylphenyl)alanine 
• 67617-67-8 allyl N-(2,6-dimethylphenyl)alaninate 
• 67617-63-4 (S)-methyl 2-(2,6-dimethylphenylamino)propanoate 
• 57646-32-9 (2R)-2-[(2,6-dimethylphenyl)amino]propanoic acid 
• 625-45-6 2-methoxyacetic acid 
• 57837-19-1 methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 

Relevant articles and documents

METHOD FOR SYNTHESIZING COMPOUND

The compound of Chemical Formula 1 and the compound of Formula 2 are used to prepare the compound of Formula 3 (a). The present invention relates to a method for preparing a compound of Formula 3, comprising preparing a compound of Formula ROH and 4 (b) in (a) and Formula 4 obtained in the above step.

Nanocellulose derivative/silica hybrid core-shell chiral stationary phase: Preparation and enantioseparation performance

Core-shell silica microspheres with a nanocellulose derivative in the hybrid shell were successfully prepared as a chiral stationary phase by a layer-by-layer self-assembly method. The hybrid shell assembled on the silica core was formed using a surfactant as template by the copolymerization reaction of tetraethyl orthosilicate and the nanocellulose derivative bearing triethoxysilyl and 3,5-dimethylphenyl groups. The resulting nanocellulose hybrid core-shell chiral packing materials (CPMs) were characterized and packed into columns, and their enantioseparation performance was evaluated by high performance liquid chromatography. The results showed that CPMs exhibited uniform surface morphology and core-shell structures. Various types of chiral compounds were efficiently separated under normal and reversed phase mode. Moreover, chloroform and tetrahydrofuran as mobile phase additives could obviously improve the resolution during the chiral separation processes. CPMs still have good chiral separation property when eluted with solvent systems with a high content of tetrahydrofuran and chloroform, which proved the high solvent resistance of this new material.

Enantiomerization and enantioselective bioaccumulation of metalaxyl in tenebrio molitor larvae

The enantiomerization and enantioselective bioaccumulation of metalaxyl by a single dose of exposure to Tenebrio molitor larvae under laboratory condition were studied by high-performance liquid chromatography tandem mass spectroscopy (HPLC-MS/MS) based on a ChiralcelOD-3R [cellulosetris-tris-(3, 5-dichlorophenyl-carbamate)] column. Exposure of enantiopure R-metalaxyl and S-metalaxyl in Tenebrio molitor larvae exhibited significant enantiomerization, with formation of the R enantiomers from the S enantiomers, and vice versa, which might be attributed to the chiral pesticide catalyzed by a certain enzyme in Tenebrio molitor larvae. Enantiomerization was not observed in wheat bran during the period of 21 d. In addition, bioaccumulation of rac-metalaxyl in Tenebrio molitor larvae was enantioselective with a preferential accumulation of S-metalaxyl. These results showed that enantioselectivity was caused not only by actual degradation and metabolism but also by enantiomerization, which was an important process in the environmental fate and behavior of metalaxyl enantiomers.