U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of METALAXYL

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

HIDE SMILES / InChI

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.

Originator

Curator's Comment: Metalaxyl was 'discovered” by researchers at the agri-chemical company Ciba-Geigy in 1977 and approved for widespread use as a fungicide in 1983.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Persistence and degradation of metalaxyl, mancozeb fungicides and its metabolite ethylenethiourea in soils.
2004 Oct
Degradation of metalaxyl and mefenoxam and effects on the microbiological properties of tropical and temperate soils.
2005 Aug
Evidence for mitochondrial gene control of mating types in Phytophthora.
2005 Nov
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005 Oct
Suppression of seed rot and preemergence of chickpea by seed treatments with fluorescent pseudomonads in Iran.
2006
Optimalisation and feasability of bioremediation systems for the processing of spray losses of pesticides.
2006
Chiral separation of metalaxyl by capillary zone electrophoresis using cyclodextrins.
2006
Application of automated mass spectrometry deconvolution and identification software for pesticide analysis in surface waters.
2006
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
Characterization and genetic distance analysis of isolates of Peronosclerospora sorghi using AFLP fingerprinting.
2006 Apr
Isolation and antifungal and antioomycete activities of staurosporine from Streptomyces roseoflavus strain LS-A24.
2006 Apr 19
Organic amendments affecting sorption, leaching and dissipation of fungicides in soils.
2006 Dec
Monitoring of pesticide residues in apples, lettuce and potato of the Slovene origin, 2001-04.
2006 Feb
Ambient air concentrations of pesticides used in potato cultivation in Prince Edward Island, Canada.
2006 Feb
[Toxicity of pesticides used in chrysanthemum crops to eggs and nymphs of Orius insidiosus (Say) (Hemiptera: Anthocoridae)].
2006 Jan-Feb
[Biological preparations with different mechanism of action for protecting potato against fungal diseases].
2006 Jan-Feb
Evidence for asexual genetic recombination in sunflower downy mildew, Plasmopara halstedii.
2006 Jun
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
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
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
Modification of clay barriers with a cationic surfactant to improve the retention of pesticides in soils.
2007 Jan 10
Evaluation of the influence of protein precipitation prior to on-line SPE-LC-API/MS procedures using multivariate data analysis.
2007 Jan 15
Evaluation of the pesticide contamination of groundwater sampled over two years from a vulnerable zone in Portugal.
2007 Jul 25
MEKC combined with SPE and sample stacking for multiple analysis of pesticides in water samples at the ng/L level.
2007 Jun
Relationship between the adsorption capacity of pesticides by wood residues and the properties of woods and pesticides.
2007 May 15
Retention of pesticides in soil columns modified in situ and ex situ with a cationic surfactant.
2007 May 25
Multiple pesticide analysis in wine by MEKC combined with solid-phase microextraction and sample stacking.
2007 Nov
Seasonal distributions of fungicides in soils and sediments of a small river basin partially devoted to vineyards.
2007 Nov
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
Pesticide residues in Italian Ready-Meals and dietary intake estimation.
2007 Sep-Oct
Significance of the long-chain organic cation structure in the sorption of the penconazole and metalaxyl fungicides by organo clays.
2008 Dec 15
In vitro antimicrobial and in vivo antioomycete activities of the novel antibiotic thiobutacin.
2008 Feb
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
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
Patents

Sample Use Guides

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
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 Sat Dec 16 02:48:37 GMT 2023
Edited
by admin
on Sat Dec 16 02:48:37 GMT 2023
Record UNII
16K4M187IF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METALAXYL
ISO   MI  
Common Name English
RIDOMIL
Brand Name English
METALAXYL [MI]
Common Name English
METALAXYL [ISO]
Common Name English
(±)-METALAXYL
Common Name English
ALANINE, N-(2,6-DIMETHYLPHENYL)-N-(2-METHOXYACETYL)-, METHYL ESTER
Common Name English
METAXANIN
Brand Name English
DL-ALANINE, N-(2,6-DIMETHYLPHENYL)-N-(METHOXYACETYL)-, METHYL ESTER
Common Name English
METALAXYL, (±)-
Common Name English
CGA-48988
Code English
Classification Tree Code System Code
EPA PESTICIDE CODE 113501
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
Code System Code Type Description
HSDB
7061
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
CHEBI
6790
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
MESH
C028175
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
WIKIPEDIA
METALAXYL
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-979-7
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
CAS
57837-19-1
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
ALANWOOD
metalaxyl
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
PUBCHEM
42586
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
FDA UNII
16K4M187IF
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY
MERCK INDEX
m7263
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6024175
Created by admin on Sat Dec 16 02:48:37 GMT 2023 , Edited by admin on Sat Dec 16 02:48:37 GMT 2023
PRIMARY