Metalaxyl

Metalaxyl is an acylalanine fungicide with systemic function.^[3] Its chemical name is methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate. It can be used to control Pythium in a number of vegetable crops, and Phytophthorainpeas. Metalaxyl-M is the ISO common name^[4] and Ridomil Gold is the trade name for the optically pure (-) / D / R active stereoisomer, which is also known as mefenoxam.^[5]

Metalaxyl

Names
IUPAC name Methyl 2-[N-(2,6-dimethylphenyl)(methoxy)acetamido]propanoate
Other names Methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate
Identifiers
CAS Number	57837-19-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6790 N
ChEMBL	ChEMBL105809 N
ChemSpider	38839 N
ECHA InfoCard	100.055.418
EC Number	260-979-7
KEGG	C10947 N
PubChem CID	42586
UNII	16K4M187IF Y
CompTox Dashboard (EPA)	DTXSID6024175
InChI InChI=1S/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 N Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-N N 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 Key: ZQEIXNIJLIKNTD-UHFFFAOYAF
SMILES COCC(=O)N(c1c(C)cccc1C)C(C)C(=O)OC
Properties
Chemical formula	C15H21NO4
Molar mass	279.33 g/mol
Appearance	Fine white powder
Density	1.20g/cm3 at 20 °C
Melting point	71 to 72 °C (160 to 162 °F; 344 to 345 K)[2]
Boiling point	295.9 °C (564.6 °F; 569.0 K) at 760 mm Hg
Solubility in water	8,400 mg/L at 22 °C
log P	1.65 (octanol/water)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It is the active ingredient in the seed treatment agent Apron XL LS.^[6]

The fungicide has suffered severe resistance problems. The fungicide was marketed for use against Phytophthora infestans. However, in the summer of 1980, in the Republic of Ireland, the crop was devastated by a potato blight epidemic after a resistant race of the oomycete appeared.^[7] Irish farmers later successfully sued the company for their losses.^{[citation needed]} Maximum pesticide residue limits for the EU/UK are set at 0.5 mg/kg for oranges and 1.0 mg/kg for apples.^{[citation needed]} As early as 1998 Pythium was known to be widely developing resistance to metalaxyl^[8] which was the most effective control at the time.^[8] Various Pythium populations have been known to have resistance to mefenoxam since the 1980s^[9] and metalaxyl since 1984.^[10] There is wide variability in resistance/sensitivity between Pythium species, with some populations showing complete ineffectiveness.^[9]

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