Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat

Metalaxyl Struktur
57837-19-1
CAS-Nr.
57837-19-1
Bezeichnung:
Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat
Englisch Name:
Metalaxyl
Synonyma:
SPAN;METALAXIL;Acylon;Jiashuangling;N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-dl-alanine methyl ester;Bleu;axyL;Fubol;MILOR;TOKAT
CBNumber:
CB4431035
Summenformel:
C15H21NO4
Molgewicht:
279.33
MOL-Datei:
57837-19-1.mol

Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat Eigenschaften

Schmelzpunkt:
72-73°C
Siedepunkt:
422.1°C (rough estimate)
Dichte
1.1083 (rough estimate)
Dampfdruck
7.5 x 10-4 Pa (25 °C)
Brechungsindex
1.5130 (estimate)
Flammpunkt:
100 °C
storage temp. 
Sealed in dry,2-8°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
1.41±0.50(Predicted)
Farbe
Off-White to Pale Beige
Wasserlöslichkeit
0.84 g/100 mL
BRN 
2947777
CAS Datenbank
57837-19-1(CAS DataBase Reference)
NIST chemische Informationen
Dl-alanine, n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-, methyl ester(57837-19-1)
EPA chemische Informationen
Metalaxyl (57837-19-1)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,F
R-Sätze: 22-43-52/53-36-20/21/22-11
S-Sätze: 13-24-37-46-61-36-26-16
RIDADR  UN 1648 3/PG 2
WGK Germany  2
RTECS-Nr. AY6910000
HS Code  29242990
Giftige Stoffe Daten 57837-19-1(Hazardous Substances Data)
Toxizität LD50 in rats (mg/kg): 669 orally (Urech)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H412 Schädlich für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 3 P273, P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R43:Sensibilisierung durch Hautkontakt möglich.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.

S-Sätze Betriebsanweisung:

S13:Von Nahrungsmitteln, Getränken und Futtermitteln fernhalten.
S24:Berührung mit der Haut vermeiden.
S37:Geeignete Schutzhandschuhe tragen.
S46:Bei Verschlucken sofort ärztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.

Beschreibung

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).

Chemische Eigenschaften

Pale Beige Solid

Verwenden

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.

Landwirtschaftliche Anwendung

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.

Handelsname

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®

Pharmakologie

In mycelium of Phytophthora megasperma,metalaxyl affected primarily rRNA synthesis (polymerase I), whereas mRNA was much less sensitive; therefore, inhibition of rRNA synthesis is considered as the primary site of action of PAFs (23).
The PAFs exhibit strong preventive and curative activity. They affect especially hyphal growth (inside and outside the plant tissue) as well as haustorium and spore formation (15). Although not fully utilized for resistance management reasons, PAFs also exhibit strong eradicative and antisporulant activity in the disease cycle of target pathogens. On the other hand, PAFs do not inhibit the early stages in the disease cycle like zoospore release, spore germination, and penetration of the host tissue (15). Because spores contain many ribosomes to support early growth stages, RNA synthesis is fully operating only after spore germination; later development stages are therefore most sensitive to PAFs (23). As a consequence of RNA inhibition, the precursors of RNA synthesis (i.e., nucleoside triphosphates) are accumulated; they activate β-1,3-glucansynthetases, which are involved in cell wall formation (23). Metalaxyl-treated hyphae often produce thicker cell walls than do untreated ones.

Sicherheitsprofil

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

mögliche Exposition

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).

Stoffwechselwegen

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.

Versand/Shipping

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

Inkompatibilitäten

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.

Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 296)Lieferanten
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Qingdao Trust Agri Chemical Co.,Ltd
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57837-19-1(Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat)Verwandte Suche:


  • n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-dl-alaninemethylester
  • n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-dl-alaninmethylester
  • n-(methoxyacetyl)-n-(2,6-xylyl)-,methylester,dl-alanin
  • ridomil2e
  • Subdue
  • subdue2e
  • methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate
  • Acylon(Ciba-Geigy)
  • Apron ZE
  • Metaxamin
  • Subdul 5SP
  • methyl (R)-2-(((2,6-dimethylphenyl) methoxyacetyl)amino)propionate
  • methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)-D-alaninate
  • methyl N-(2-methoxyacethyl)-N-(2,6-xylyl-D-alaninate
  • Metalaxy-M
  • METALAXYL PESTANAL
  • METALAXYL, 100MG, NEAT
  • METALAXYL 98%
  • METALAXIL ,METHYL N-(2,6-DIMETHYL-PHENYL)-N-(2'-METHOXYACETYL)-DL-ALANINATE
  • Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl ester
  • metalaxyl (bsi,iso,ansi)
  • metalaxyl solution
  • Metalaxyl-M,MEFENOXAM
  • (R)-METHYL 2-(N-(2,6-DIMETHYLPHENYL)-2-METHOXYACETAMIDO)PROPANOATE
  • N-(Metoxyacetyl)-N-(2,6-dimethylphenyl)-alanine methyl ester
  • metalaxyl (ISO) methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate
  • Metalaxyl W.P.
  • RIDOMIL
  • RIDOMIL(R)
  • Ridonil
  • cga48988
  • CGA-48988
  • d,l-n-(2,6-dimethylphenyl)-n-(2’-methoxyacetyl)alaninatedemethyle
  • DL-Alanine,N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-,methylester
  • Metalasyl
  • Metaxanin
  • Methyl 2-[(methoxyacetyl)-2,6-dimethylanilino]propanoate
  • MethylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninemethylester
  • methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alinate
  • Apron 35 SD
  • Bleu
  • Fubol
  • methyl-N-(2'-methoxyacetyl)-N-(2,6-dimethyl phenyl)-D,L-α-alaninate
  • subdue5sp
  • SUBDUE(R)
  • SALOR-INT L497002-1EA
  • MILOR
  • TOKAT
  • APRON
  • APRON(R)
  • 'LGC' (1638)
  • LABOTEST-BB LT00134856
  • INFRA
  • FORAXYL
  • METALAXYL
  • METAX
  • METHYL N-(2,6-DIMETHYL-PHENYL)-N-(2'-METHOXYACETYL)-DL-ALANINATE
  • METHYL N-(2-METHOXYACETYL)-N-(2,6-XYLYL)-DL-ALANINATE
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