Benalaxyl

Basic Info

Common NameBenalaxyl(F05842)
2D Structure
FRCD IDF05842
CAS Number71626-11-4
PubChem CID51369
FormulaC20H23NO3
IUPAC Name

methyl 2-(2,6-dimethyl-N-(2-phenylacetyl)anilino)propanoate

InChI Key

CJPQIRJHIZUAQP-UHFFFAOYSA-N

InChI

InChI=1S/C20H23NO3/c1-14-9-8-10-15(2)19(14)21(16(3)20(23)24-4)18(22)13-17-11-6-5-7-12-17/h5-12,16H,13H2,1-4H3

Canonical SMILES

CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)CC2=CC=CC=C2

Isomeric SMILES

CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)CC2=CC=CC=C2

Synonyms
        
            71626-11-4
        
            methyl 2-(2,6-dimethyl-N-(2-phenylacetyl)anilino)propanoate
        
            BENALAXYL
        
            Galben
        
            Benalaxyl [BSI:ISO]
        
            Caswell No. 471AC
        
            EINECS 275-728-7
        
            M 9834
        
            EPA Pesticide Chemical Code 127001
        
            BRN 3001587
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentAlpha amino acid esters
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAlpha-amino acid ester - Alanine or derivatives - Phenylacetamide - Anilide - M-xylene - Xylene - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Methyl ester - Carboxylic acid ester - Carboxamide group - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Properties

Property NameProperty Value
Molecular Weight325.408
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Complexity421
Monoisotopic Mass325.168
Exact Mass325.168
XLogP3.4
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9745
Human Intestinal AbsorptionHIA+0.8469
Caco-2 PermeabilityCaco2+0.7759
P-glycoprotein SubstrateNon-substrate0.8099
P-glycoprotein InhibitorNon-inhibitor0.5718
Inhibitor0.5000
Renal Organic Cation TransporterNon-inhibitor0.8564
Distribution
Subcellular localizationMitochondria0.8039
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7156
CYP450 2D6 SubstrateNon-substrate0.8062
CYP450 3A4 SubstrateSubstrate0.6441
CYP450 1A2 InhibitorNon-inhibitor0.5949
CYP450 2C9 InhibitorNon-inhibitor0.5574
CYP450 2D6 InhibitorNon-inhibitor0.9345
CYP450 2C19 InhibitorInhibitor0.6794
CYP450 3A4 InhibitorNon-inhibitor0.6081
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.9055
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9850
Non-inhibitor0.8230
AMES ToxicityNon AMES toxic0.8343
CarcinogensNon-carcinogens0.5991
Fish ToxicityHigh FHMT0.6875
Tetrahymena Pyriformis ToxicityHigh TPT0.5750
Honey Bee ToxicityLow HBT0.8488
BiodegradationNot ready biodegradable0.9705
Acute Oral ToxicityIII0.8153
Carcinogenicity (Three-class)Non-required0.5688
Model Value Unit
Absorption
Aqueous solubility-2.9835LogS
Caco-2 Permeability1.3780LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9203LD50, mol/kg
Fish Toxicity0.7227pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3995pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
FludioxonilNew Zealand0. 5mg/kg
Milk & Dairy ProduceBritain0.05mg/kg
Meat, Fat & Preparations Of MeatBritain0.05mg/kg
Other Cereals Do Not Include RiceBritain0.05mg/kg
RiceBritain0.05mg/kg
MilletBritain0.05mg/kg
BuckwheatBritain0.05mg/kg
MaizeBritain0.05mg/kg
TriticaleBritain0.05mg/kg
OatsBritain0.05mg/kg
SorghumBritain0.05mg/kg
BarleyBritain0.05mg/kg
RyeBritain0.05mg/kg
WheatBritain0.05mg/kg
HopBritain0.1mg/kg
TeaBritain0.1mg/kg
Ware PotatoesBritain0.05mg/kg
Early PotatoesBritain0.05mg/kg
Other OilseedsBritain0.05mg/kg
Hemp SeedBritain0.05mg/kg

References

TitleJournalDatePubmed ID
Subacute oral toxicity assessment of benalaxyl in mice based on metabolomics methods.Chemosphere2018 Jan29054078
Acylamino acid chiral fungicides on toxiciepigenetics in lambda DNA methylation.Food Chem Toxicol2017 Nov28456568
Effects of wastewater irrigation and sewage sludge application on soil residuesof chiral fungicide benalaxyl.Environ Pollut2017 May28288350
Enantioselective metabolism and enantiomerization of benalaxyl in mice.Chemosphere2017 Feb27886532
Stereoselective Behavior of the Fungicide Benalaxyl During Grape Growth and theWine-Making Process.Chirality2016 May26934695
A combined non-targeted and targeted metabolomics approach to study thestereoselective metabolism of benalaxyl enantiomers in mouse hepatic microsomes.Environ Pollut2016 May26874317
Up-and-down-shaker-assisted dispersive liquid-liquid microextraction coupled withgas chromatography-mass spectrometry for the determination of fungicides in wine.Food Chem2015 Oct 1525952882
Fate and stereoselective behavior of benalaxyl in a water-sediment microcosm.J Agric Food Chem2015 Jun 326009811
Determination of fungicides in white grape bagasse by pressurized liquidextraction and gas chromatography tandem mass spectrometry.J Chromatogr A2014 May 2324746069
Enantiomerization and enantioselective bioaccumulation of benalaxyl in Tenebriomolitor larvae from wheat bran.J Agric Food Chem2013 Sep 2524000806
Enantioselective determination of acylamino acid fungicides in vegetables andfruits by chiral liquid chromatography coupled with tandem mass spectrometry.J Sep Sci2012 Aug22753298
Multiresidue determination of 11 new fungicides in grapes and wines byliquid-liquid extraction/clean-up and programmable temperature vaporizationinjection with analyte protectants/gas chromatography/ion trap mass spectrometry.J Chromatogr A2009 Aug 719576591
Pesticide analysis in tomatoes by solid-phase microextraction and micellarelectrokinetic chromatography.J Chromatogr A2008 Mar 2118280487
MEKC combined with SPE and sample stacking for multiple analysis of pesticides inwater samples at the ng/L level.Electrophoresis2007 Jun17476718
Enantiomeric resolution of chiral pesticides by high-performance liquidchromatography.J Agric Food Chem2006 Mar 816506803
Signum, a new fungicide for control of leaf diseases in outdoor vegetables.Commun Agric Appl Biol Sci200516637178
Complexation of several fungicides with beta-cyclodextrin: determination of theassociation constants and isolation of the solid complexes.J Agric Food Chem2003 Aug 1312903966
Application of an ELISA to the determination of benalaxyl in red wines.J Agric Food Chem2000 Jan10637047
Pesticide residues in grapes, wine, and their processing products.J Agric Food Chem2000 Apr10775335
Gas chromatographic determination of benalaxyl residues in different crops and water.J AOAC Int1993 May-Jun8318859