Metazachlor

Basic Info

Common NameMetazachlor(F06305)
2D Structure
FRCD IDF06305
CAS Number67129-08-2
PubChem CID49384
FormulaC14H16ClN3O
IUPAC Name

2-chloro-N-(2,6-dimethylphenyl)-N-(pyrazol-1-ylmethyl)acetamide

InChI Key

STEPQTYSZVCJPV-UHFFFAOYSA-N

InChI

InChI=1S/C14H16ClN3O/c1-11-5-3-6-12(2)14(11)18(13(19)9-15)10-17-8-4-7-16-17/h3-8H,9-10H2,1-2H3

Canonical SMILES

CC1=C(C(=CC=C1)C)N(CN2C=CC=N2)C(=O)CCl

Isomeric SMILES

CC1=C(C(=CC=C1)C)N(CN2C=CC=N2)C(=O)CCl

Synonyms
        
            Metazachlor [BSI:ISO]
        
            2-Chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)acetamide
        
            METAZACHLOR
        
            67129-08-2
        
            Metazachlore
        
            Butisan S
        
            BAS 479H
        
            Sultan
        
            Pree
        
            Metazachlore [ISO-French]
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassAnilides
Intermediate Tree NodesNot available
Direct ParentAnilides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAnilide - Xylene - M-xylene - Azole - Pyrazole - Tertiary carboxylic acid amide - Heteroaromatic compound - Chloroacetamide - Carboxamide group - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Carbonyl group - Alkyl halide - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Alkyl chloride - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Organic oxide - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Properties

Property NameProperty Value
Molecular Weight277.752
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Complexity303
Monoisotopic Mass277.098
Exact Mass277.098
XLogP2.7
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9878
Human Intestinal AbsorptionHIA+0.9939
Caco-2 PermeabilityCaco2+0.5852
P-glycoprotein SubstrateNon-substrate0.7185
P-glycoprotein InhibitorNon-inhibitor0.8568
Non-inhibitor0.6647
Renal Organic Cation TransporterNon-inhibitor0.5769
Distribution
Subcellular localizationMitochondria0.7910
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8342
CYP450 2D6 SubstrateNon-substrate0.8358
CYP450 3A4 SubstrateSubstrate0.6814
CYP450 1A2 InhibitorNon-inhibitor0.5870
CYP450 2C9 InhibitorNon-inhibitor0.7515
CYP450 2D6 InhibitorNon-inhibitor0.8308
CYP450 2C19 InhibitorNon-inhibitor0.5436
CYP450 3A4 InhibitorNon-inhibitor0.5081
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5390
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8641
Non-inhibitor0.6916
AMES ToxicityNon AMES toxic0.5507
CarcinogensCarcinogens 0.5000
Fish ToxicityHigh FHMT0.7284
Tetrahymena Pyriformis ToxicityHigh TPT0.8698
Honey Bee ToxicityLow HBT0.9284
BiodegradationNot ready biodegradable0.9886
Acute Oral ToxicityIII0.8099
Carcinogenicity (Three-class)Non-required0.4623
Model Value Unit
Absorption
Aqueous solubility-2.5152LogS
Caco-2 Permeability1.3331LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4752LD50, mol/kg
Fish Toxicity1.5409pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6356pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.02*26/06/2018
Citrus fruits0110000European Union0.02*26/06/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.02*26/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.02*26/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.02*26/06/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.02*26/06/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.02*26/06/2018
Others (2)0110990European Union0.02*26/06/2018
Tree nuts0120000European Union0.02*26/06/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*26/06/2018
Brazil nuts0120020European Union0.02*26/06/2018
Cashew nuts0120030European Union0.02*26/06/2018
Chestnuts0120040European Union0.02*26/06/2018
Pecans (Hickory nuts,)0120080European Union0.02*26/06/2018
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union0.02*26/06/2018
Quinces (Chinese quinces, Japanese quinces,)0130030European Union0.02*26/06/2018
Medlars0130040European Union0.02*26/06/2018
Loquats/Japanese medlars0130050European Union0.02*26/06/2018
Others (2)0130990European Union0.02*26/06/2018
Stone fruits0140000European Union0.02*26/06/2018

References

TitleJournalDatePubmed ID
The Potential of Graphene as an Adsorbent for Five Pesticides from DifferentClasses in Rape Oil Samples Using Dispersive Solid-Phase Extraction.J Anal Methods Chem2018 Apr 129805833
Pesticide residues in propolis from Spain and Chile. An approach using nearinfrared spectroscopy.Talanta2017 Apr 128153295
A novel method for the determination of some pesticides in vegetable oils basedon dissociation extraction followed by gas chromatography-mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016Aug27382960
Dissipation and runoff transport of metazachlor herbicide in rapeseed cultivated and uncultivated plots in field conditions.Environ Sci Pollut Res Int2016 Oct27464655
Pesticide pressure and fish farming in barrage pond in northeastern France. Part III: how management can affect pesticide profiles in edible fish?Environ Sci Pollut Res Int2013 Jan22467231
Accumulation and half-lives of 13 pesticides in muscle tissue of freshwaterfishes through food exposure.Chemosphere2013 Apr23374295
Low molecular weight poly(lactic acid) microparticles for controlled release ofthe herbicide metazachlor: preparation, morphology, and release kinetics.J Agric Food Chem2012 Apr 2522480233
Glyphosate adsorption in soils compared to herbicides replaced with theintroduction of glyphosate resistant crops.Chemosphere2005 Nov15951002