Metalaxyl

Metalaxyl
Names
	IUPAC names 2-[(2,6-dimethylphenyl)- (2-methoxy-1-oxoethyl) amino]propanoic; acid methyl ester
Identifiers
CAS Number	57837-19-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6790 ;
ChEMBL	ChEMBL105809 ;
ChemSpider	38839 ;
ECHA InfoCard	100.055.418
EC Number	260-979-7;
KEGG	C10947 ;
PubChem CID	42586;
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 Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-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 CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC;
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)
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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Metalaxyl is a phenylamide fungicide with systemic function. 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 Phytophthora in peas. Metalaxyl-M is the trade name of the optically pure stereoisomer.

It is the active ingredient in the seed treatment agent Apron XL LS.^[3]

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.^[4] 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

References

^ Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 134
^ O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1058
^ http://www.gov.mb.ca/agriculture/crops/vegetablecrops/pdf/bmz10s02.pdf
^ Working on potato blight in Northern Ireland

External links

Metalaxyl in the Pesticide Properties DataBase (PPDB)
Metalaxyl-M in the Pesticide Properties DataBase (PPDB)

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[1] Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 134

[2] O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1058

[3] ttp://www.gov.mb.ca/agriculture/crops/vegetablecrops/pdf/bmz10s02.pdf

[4] Working on potato blight in Northern Ireland

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