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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
19.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
16K4M187IF
Record Status Validated (UNII)
Record Version