Methiocarb

Basic Info

Common NameMethiocarb(F04007)
2D Structure
Description

Methiocarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF04007
CAS Number2032-65-7
PubChem CID16248
FormulaC11H15NO2S
IUPAC Name

(3,5-dimethyl-4-methylsulfanylphenyl) N-methylcarbamate

InChI Key

YFBPRJGDJKVWAH-UHFFFAOYSA-N

InChI

InChI=1S/C11H15NO2S/c1-7-5-9(14-11(13)12-3)6-8(2)10(7)15-4/h5-6H,1-4H3,(H,12,13)

Canonical SMILES

CC1=CC(=CC(=C1SC)C)OC(=O)NC

Isomeric SMILES

CC1=CC(=CC(=C1SC)C)OC(=O)NC

Synonyms
        
            Methiocarbe
        
            METHIOCARB
        
            Mercaptodimethur
        
            2032-65-7
        
            Metmercapturon
        
            Mesurol
        
            Draza
        
            Mesurol Phenol
        
            Grandslam
        
            Lizetan
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenoxy compounds
Intermediate Tree NodesNot available
Direct ParentPhenoxy compounds
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenoxy compound - Aryl thioether - Thiophenol ether - M-xylene - Xylene - Alkylarylthioether - Carboximidic acid derivative - Thioether - Sulfenyl compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Imine - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Properties

Property NameProperty Value
Molecular Weight225.306
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity211
Monoisotopic Mass225.082
Exact Mass225.082
XLogP2.9
Formal Charge0
Heavy Atom Count15
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+0.9550
Human Intestinal AbsorptionHIA+0.9965
Caco-2 PermeabilityCaco2+0.6668
P-glycoprotein SubstrateNon-substrate0.8851
P-glycoprotein InhibitorNon-inhibitor0.9110
Non-inhibitor0.9400
Renal Organic Cation TransporterNon-inhibitor0.8970
Distribution
Subcellular localizationMitochondria0.7075
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6949
CYP450 2D6 SubstrateSubstrate0.8918
CYP450 3A4 SubstrateSubstrate0.5337
CYP450 1A2 InhibitorInhibitor0.6271
CYP450 2C9 InhibitorNon-inhibitor0.8215
CYP450 2D6 InhibitorNon-inhibitor0.9308
CYP450 2C19 InhibitorNon-inhibitor0.6777
CYP450 3A4 InhibitorNon-inhibitor0.6384
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5145
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9770
Non-inhibitor0.9207
AMES ToxicityAMES toxic0.5773
CarcinogensNon-carcinogens0.8568
Fish ToxicityHigh FHMT0.9313
Tetrahymena Pyriformis ToxicityHigh TPT0.8421
Honey Bee ToxicityHigh HBT0.8839
BiodegradationNot ready biodegradable0.9468
Acute Oral ToxicityI0.7812
Carcinogenicity (Three-class)Non-required0.5666
Model Value Unit
Absorption
Aqueous solubility-3.0113LogS
Caco-2 Permeability1.7387LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.6570LD50, mol/kg
Fish Toxicity1.4135pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4822pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cucumber(Including Gherkin)Japan0.05ppm
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.201/09/2008
Cashew nuts0120030European Union0.201/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.1*01/09/2008
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.1*01/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.201/09/2008
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.201/09/2008
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.201/09/2008
Others (2)0110990European Union0.201/09/2008
Tree nuts0120000European Union0.201/09/2008
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.201/09/2008
Brazil nuts0120020European Union0.201/09/2008
Chestnuts0120040European Union0.201/09/2008
Coconuts (Areca nuts/betel nuts,)0120050European Union0.201/09/2008
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.201/09/2008
Macadamias0120070European Union0.201/09/2008
Pecans (Hickory nuts,)0120080European Union0.201/09/2008
Pistachios0120100European Union0.201/09/2008
Walnuts0120110European Union0.201/09/2008
Others (2)0120990European Union0.201/09/2008

References

TitleJournalDatePubmed ID
Risk Assessment of Florists Exposed to Pesticide Residues through Handling of Flowers and Preparing Bouquets.Int J Environ Res Public Health2017 May 1328505067
Simultaneous quantification of methiocarb and its metabolites, methiocarbsulfoxide and methiocarb sulfone, in five food products of animal origin usingtandem mass spectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2017 Aug 1528666230
Pesticide Residues on Three Cut Flower Species and Potential Exposure of Floristsin Belgium.Int J Environ Res Public Health2016 Sep 2327669276
Occurrence and removal of organic micropollutants: An overview of the watch list of EU Decision 2015/495.Water Res2016 May 126967909
Multiresidue method for the quantitation of 20 pesticides in aquatic products.Anal Bioanal Chem2015 Dec26466578
Determination of methiocarb and its degradation products, methiocarb sulfoxideand methiocarb sulfone, in bananas using QuEChERS extraction.J Agric Food Chem2013 Jan 1623252625
Reconciling sensory cues and varied consequences of avian repellents.Physiol Behav2011 Feb 120971129
Electrospray ionization matrix effect as an uncertainty source in HPLC/ESI-MSpesticide residue analysis.J AOAC Int2010 Jan-Feb20334192
Methiocarb-induced oxidative damage following subacute exposure and the protective effects of vitamin E and taurine in rats.Food Chem Toxicol2009 Jul19394395
Determination of 23 pesticide residues in leafy vegetables using gaschromatography-ion trap mass spectrometry and analyte protectants.J Chromatogr A2008 Jul 418343389
Evaluation of pesticide residue in grape juices and the effect of naturalantioxidants on their degradation rate.Anal Bioanal Chem2007 Nov17641884
Survey of carbamate and organophosphorous pesticide export from a south Florida(U.S.A.) agricultural watershed: implications of sampling frequency on ecologicalrisk estimation.Environ Toxicol Chem2006 Nov17089706
Determination of pesticides in soy-based infant formula using liquidchromatography with electrospray ionization tandem mass spectrometry.J AOAC Int2006 Jan-Feb16512251
Screening and evaluation of fruit samples for four pesticide residues.J AOAC Int2005 May-Jun16001861
Perinatal exposure to the fungicide prochloraz feminizes the male rat offspring.Toxicol Sci2005 Jun15788727
Determination of pesticides in apple-based infant foods using liquidchromatography electrospray ionization tandem mass spectrometry.J Agric Food Chem2005 Feb 915686398
The combined antiandrogenic effects of five commonly used pesticides.Toxicol Appl Pharmacol2004 Nov 1515519604
Determination of n-methylcarbamates in foods.Cent Eur J Public Health2004 Dec15666462
Survival tests with Chironomus riparius exposed to spiked sediments can profit from DEBtox model.Water Res2003 Jun12753846
Assessment of pesticide residues in honey samples from portugal and Spain.J Agric Food Chem2003 Dec 3114690408

Targets

Target Details

Acetylcholinesterase

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
Target Details

Cholinesterase

General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088