Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H21NO4 |
Molecular Weight | 279.3315 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C
InChI
InChIKey=ZQEIXNIJLIKNTD-UHFFFAOYSA-N
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
Molecular Formula | C15H21NO4 |
Molecular Weight | 279.3315 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Metalaxyl is a systemic fungicide used to control plant diseases caused by Oomycete fungi. Metalaxyl is a racemic mixture of two isomers, one of which, the R-enantiomer, is the active form. This
enantiomer is the basis of the fungicide, metalaxyl-M (mefenoxam), which is effective at half the application
rate of metalaxyl. This was developed by Syngenta as a replacement for metalaxyl, and was part of a
strategy to stifle generic competition. Metalaxyl`s formulations include granules, wettable powders, dusts, and emulsifiable concentrates. Application may be by foliar or soil incorporation, surface spraying (broadcast or band), drenching, and seed treatment. Metalaxyl registered products either contain metalaxyl as the sole active ingredient or are combined with other active ingredients (e.g., captan, mancozeb, copper compounds, carboxin). Due to its broad-spectrum activity, metalaxyl is used world-wide on a variety of fruit and vegetable crops. Its effectiveness results from inhibition of uridine incorporation into RNA and specific inhibition of RNA polymerase-1. Metalaxyl has both curative and systemic properties. Its mammalian toxicity is classified as EPA toxicity class III and it is also relatively non-toxic to most nontarget arthropod and vertebrate species.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095196 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2754760 |
19.0 µM [IC50] | ||
Target ID: CHEMBL2093864 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Persistence and degradation of metalaxyl, mancozeb fungicides and its metabolite ethylenethiourea in soils. | 2004 Oct |
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Degradation of metalaxyl and mefenoxam and effects on the microbiological properties of tropical and temperate soils. | 2005 Aug |
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Evidence for mitochondrial gene control of mating types in Phytophthora. | 2005 Nov |
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Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies. | 2005 Oct |
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Suppression of seed rot and preemergence of chickpea by seed treatments with fluorescent pseudomonads in Iran. | 2006 |
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Optimalisation and feasability of bioremediation systems for the processing of spray losses of pesticides. | 2006 |
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Chiral separation of metalaxyl by capillary zone electrophoresis using cyclodextrins. | 2006 |
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Application of automated mass spectrometry deconvolution and identification software for pesticide analysis in surface waters. | 2006 |
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Agricultural pesticide residues in farm ditches of the Lower Fraser Valley, British Columbia, Canada. | 2006 |
|
Characterization of atrazine-induced gonadal malformations in African clawed frogs (Xenopus laevis) and comparisons with effects of an androgen antagonist (cyproterone acetate) and exogenous estrogen (17beta-estradiol): Support for the demasculinization/feminization hypothesis. | 2006 Apr |
|
Pesticide mixtures, endocrine disruption, and amphibian declines: are we underestimating the impact? | 2006 Apr |
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Characterization and genetic distance analysis of isolates of Peronosclerospora sorghi using AFLP fingerprinting. | 2006 Apr |
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Isolation and antifungal and antioomycete activities of staurosporine from Streptomyces roseoflavus strain LS-A24. | 2006 Apr 19 |
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Organic amendments affecting sorption, leaching and dissipation of fungicides in soils. | 2006 Dec |
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Monitoring of pesticide residues in apples, lettuce and potato of the Slovene origin, 2001-04. | 2006 Feb |
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Ambient air concentrations of pesticides used in potato cultivation in Prince Edward Island, Canada. | 2006 Feb |
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[Toxicity of pesticides used in chrysanthemum crops to eggs and nymphs of Orius insidiosus (Say) (Hemiptera: Anthocoridae)]. | 2006 Jan-Feb |
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[Biological preparations with different mechanism of action for protecting potato against fungal diseases]. | 2006 Jan-Feb |
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Evidence for asexual genetic recombination in sunflower downy mildew, Plasmopara halstedii. | 2006 Jun |
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Dynamics of pesticides in potato crops. | 2006 Mar 8 |
|
Matrix solid-phase dispersion microextraction and determination of pesticide residues in medicinal herbs by gas chromatography with a nitrogen-phosphorus detector. | 2006 Mar-Apr |
|
Modified superheated water extraction of pesticides from spiked sediment and soil. | 2006 May |
|
Protocols for optimizing MS/MS parameters with an ion-trap GC-MS instrument. | 2006 Oct |
|
Influence of pH and soil copper on adsorption of metalaxyl and penconazole by the surface layer of vineyard soils. | 2006 Oct 18 |
|
Influence of pH on the stereoselective degradation of the fungicides epoxiconazole and cyproconazole in soils. | 2006 Sep 1 |
|
Soy polyol formulations as novel seed treatments for the management of soil-borne diseases of soybean. | 2007 |
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Pesticide retention in an experimental wetland treating non-point source pollution from agriculture runoff. | 2007 |
|
Design for electrospray ionization-ion mobility spectrometry. | 2007 Apr 15 |
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Determination of pesticide residues in soil by modified matrix solid-phase dispersion and gas chromatography. | 2007 Aug |
|
Antifungal activity of salaceyin A against Colletotrichum orbiculare and Phytophthora capsici. | 2007 Aug |
|
Assessment of the genotoxicity of imidacloprid and metalaxyl in cultured human lymphocytes and rat bone-marrow. | 2007 Dec 1 |
|
The direct chiral separations of fungicide enantiomers on amylopectin based chiral stationary phase by HPLC. | 2007 Feb |
|
Molecularly imprinted solid-phase extraction method for the high-performance liquid chromatographic analysis of fungicide pyrimethanil in wine. | 2007 Feb 9 |
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Modification of clay barriers with a cationic surfactant to improve the retention of pesticides in soils. | 2007 Jan 10 |
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Evaluation of the influence of protein precipitation prior to on-line SPE-LC-API/MS procedures using multivariate data analysis. | 2007 Jan 15 |
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Evaluation of the pesticide contamination of groundwater sampled over two years from a vulnerable zone in Portugal. | 2007 Jul 25 |
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MEKC combined with SPE and sample stacking for multiple analysis of pesticides in water samples at the ng/L level. | 2007 Jun |
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Relationship between the adsorption capacity of pesticides by wood residues and the properties of woods and pesticides. | 2007 May 15 |
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Retention of pesticides in soil columns modified in situ and ex situ with a cationic surfactant. | 2007 May 25 |
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Multiple pesticide analysis in wine by MEKC combined with solid-phase microextraction and sample stacking. | 2007 Nov |
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Seasonal distributions of fungicides in soils and sediments of a small river basin partially devoted to vineyards. | 2007 Nov |
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Sensitive determination of fungicides and prometryn in environmental water samples using multiwalled carbon nanotubes solid-phase extraction cartridge. | 2007 Oct 29 |
|
Elimination of racemic and enantioenriched metalaxyl based fungicides under tropical conditions in the field. | 2007 Sep |
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Pesticide residues in Italian Ready-Meals and dietary intake estimation. | 2007 Sep-Oct |
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Significance of the long-chain organic cation structure in the sorption of the penconazole and metalaxyl fungicides by organo clays. | 2008 Dec 15 |
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In vitro antimicrobial and in vivo antioomycete activities of the novel antibiotic thiobutacin. | 2008 Feb |
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Method development for the determination of selected pesticides on tobacco by high-performance liquid chromatography-electrospray ionisation-tandem mass spectrometry. | 2008 Feb 15 |
|
The chiral resolution of pesticides on amylose-tris(3,5-dimethylphenylcarbamate) CSP by HPLC and the enantiomeric identification by circular dichroism. | 2008 Jan |
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Measures to reduce pesticide spray drift in a small aquatic ecosystem in vineyard estate. | 2008 Jan 25 |
|
Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants. | 2008 Jul 4 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2537904
Intraperitoneal injection of metalaxyl (250 mg/kg) produced a decrease in heart rate lasting for more than 60 min in anesthetized rats.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8525470
Metalaxyl induced cell transformation at any assayed dosage, i.e., 500, 250, and 50 ug/ml, in the presence of bioactivation, and at the highest dosage (500 ug/ml) in the absence of bioactivation in the in vitro BALB/c 3T3 cell transformation test.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:48:37 GMT 2023
by
admin
on
Sat Dec 16 02:48:37 GMT 2023
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Record UNII |
16K4M187IF
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
113501
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7061
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6790
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C028175
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METALAXYL
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260-979-7
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57837-19-1
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metalaxyl
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42586
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16K4M187IF
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m7263
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DTXSID6024175
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