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 Phytophthora in peas. 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]
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]
Referencesedit
^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
^Sukul, P; Spiteller, M (2000). "Metalaxyl: persistence, degradation, metabolism, and analytical methods". Reviews of Environmental Contamination and Toxicology. 164: 1–26. PMID 12587832.
^"Compendium of Pesticide Common Names: metalaxyl". BCPC.
^Monkiedje, Adolphe; Spiteller, Michael (2002). "Effects of the phenylamide fungicides, mefenoxam and metalaxyl, on the microbiological properties of a sandy loam and a sandy clay soil". Biology and Fertility of Soils. 35 (6): 393–398. doi:10.1007/s00374-002-0485-1. S2CID 22642870.
^(PDF). Government of Manitoba. Archived from the original (PDF) on 2007-09-30.
^ ab"Survey of Pythium Isolates for Resistance to Subdue (metalaxyl)" (PDF). UMass Amherst. Retrieved 2020-11-23.
^ abDel Castillo Múnera, Johanna; Hausbeck, Mary K. (2016). "Characterization of Pythium Species Associated With Greenhouse Floriculture Crops in Michigan". Plant Disease. 100 (3). American Phytopathological Society: 569–576. doi:10.1094/pdis-03-15-0296-re. ISSN 0191-2917. PMID 30688597.
metalaxyl, acylalanine, fungicide, with, systemic, function, chemical, name, methyl, methoxyacetyl, xylyl, alaninate, used, control, pythium, number, vegetable, crops, phytophthora, peas, common, name, ridomil, gold, trade, name, optically, pure, active, stere. 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 Phytophthora in peas 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 NKey ZQEIXNIJLIKNTD UHFFFAOYSA N NInChI 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 5H3Key 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 Y N 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 References edit 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 Sukul P Spiteller M 2000 Metalaxyl persistence degradation metabolism and analytical methods Reviews of Environmental Contamination and Toxicology 164 1 26 PMID 12587832 Compendium of Pesticide Common Names metalaxyl BCPC Monkiedje Adolphe Spiteller Michael 2002 Effects of the phenylamide fungicides mefenoxam and metalaxyl on the microbiological properties of a sandy loam and a sandy clay soil Biology and Fertility of Soils 35 6 393 398 doi 10 1007 s00374 002 0485 1 S2CID 22642870 bmz10s02 pdf PDF Government of Manitoba Archived from the original PDF on 2007 09 30 Working on potato blight in Northern Ireland a b Survey of Pythium Isolates for Resistance to Subdue metalaxyl PDF UMass Amherst Retrieved 2020 11 23 a b Del Castillo Munera Johanna Hausbeck Mary K 2016 Characterization of Pythium Species Associated With Greenhouse Floriculture Crops in Michigan Plant Disease 100 3 American Phytopathological Society 569 576 doi 10 1094 pdis 03 15 0296 re ISSN 0191 2917 PMID 30688597 Sanders P L 1984 Failure of Metalaxyl to Control Pythium Blight on Turfgrass in Pennsylvania Plant Disease 68 1 American Phytopathological Society 776 doi 10 1094 pd 68 776 ISSN 0191 2917 External links editMetalaxyl in the Pesticide Properties DataBase PPDB Metalaxyl M in the Pesticide Properties DataBase PPDB nbsp This mycology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Metalaxyl amp oldid 1192319920, wikipedia, wiki, book, books, library,
