Metolcarb
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Basic Info
Common Name | Metolcarb(F04011) |
2D Structure | |
Description | Metolcarb 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 ID | F04011 |
CAS Number | 1129-41-5 |
PubChem CID | 14322 |
Formula | C9H11NO2 |
IUPAC Name | (3-methylphenyl) N-methylcarbamate |
InChI Key | VOEYXMAFNDNNED-UHFFFAOYSA-N |
InChI | InChI=1S/C9H11NO2/c1-7-4-3-5-8(6-7)12-9(11)10-2/h3-6H,1-2H3,(H,10,11) |
Canonical SMILES | CC1=CC(=CC=C1)OC(=O)NC |
Isomeric SMILES | CC1=CC(=CC=C1)OC(=O)NC |
Wikipedia | Metolcarb |
Synonyms | 3-Tolyl N-methylcarbamate METOLCARB m-Tolyl methylcarbamate Metacrate MTMC Tsumacide m-Cresyl methylcarbamate 1129-41-5 3-Tolyl methylcarbamate m-Tolyl N-methylcarbamate |
Classifies | Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Phenyl methylcarbamates |
Intermediate Tree Nodes | Not available |
Direct Parent | Phenyl methylcarbamates |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Phenyl methylcarbamate - Phenoxy compound - Toluene - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 165.192 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 2 |
Complexity | 159 |
Monoisotopic Mass | 165.079 |
Exact Mass | 165.079 |
XLogP | 1.7 |
Formal Charge | 0 |
Heavy Atom Count | 12 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9709 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2+ | 0.7768 |
P-glycoprotein Substrate | Non-substrate | 0.8597 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9667 |
Non-inhibitor | 0.9710 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8938 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7395 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7776 |
CYP450 2D6 Substrate | Substrate | 0.8411 |
CYP450 3A4 Substrate | Substrate | 0.5104 |
CYP450 1A2 Inhibitor | Inhibitor | 0.5051 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9815 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9291 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9574 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9335 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8677 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9376 |
Non-inhibitor | 0.9702 | |
AMES Toxicity | AMES toxic | 0.5121 |
Carcinogens | Non-carcinogens | 0.8685 |
Fish Toxicity | High FHMT | 0.7020 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9698 |
Honey Bee Toxicity | High HBT | 0.8353 |
Biodegradation | Not ready biodegradable | 0.6165 |
Acute Oral Toxicity | II | 0.7495 |
Carcinogenicity (Three-class) | Non-required | 0.5338 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.0337 | LogS |
Caco-2 Permeability | 1.5824 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.7588 | LD50, mol/kg |
Fish Toxicity | 1.7742 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.0768 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Prussian blue mediated amplification combined with signal enhancement of ordered mesoporous carbon for ultrasensitive and specific quantification of metolcarb by a three-dimensional molecularly imprinted electrochemical sensor. | Biosens Bioelectron | 2015 Feb 15 | 25240126 |
Rapid and sensitive suspension array for multiplex detection of organophosphorus pesticides and carbamate pesticides based on silica-hydrogel hybrid microbeads. | J Hazard Mater | 2014 May 30 | 24769809 |
Extraction of carbamate pesticides in fruit samples by graphene reinforced hollowfibre liquid microextraction followed by high performance liquid chromatographic detection. | Food Chem | 2014 Aug 15 | 24679760 |
Rapid determination of metolcarb residues in foods using a biomimeticenzyme-linked immunosorbent assay employing a novel molecularly imprinted polymerfilm as artificial antibody. | J AOAC Int | 2013 Mar-Apr | 23767373 |
Determination of metolcarb in food by capillary electrophoresis immunoassay with a laser-induced fluorescence detector. | Electrophoresis | 2012 May | 22648817 |
Development of chemiluminescence enzyme-linked immunosorbent assay for thescreening of metolcarb and carbaryl in orange juice, cabbage and cucumber. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2010Mar | 20155539 |
Synthesis and insecticidal activity of novel carbamate derivatives as potentialdual-binding site acetylcholinesterase inhibitors. | J Agric Food Chem | 2010 Dec 22 | 21114293 |
Sequential injection kinetic spectrophotometric determination of quaternarymixtures of carbamate pesticides in water and fruit samples using artificialneural networks for multivariate calibration. | Spectrochim Acta A Mol Biomol Spectrosc | 2009 Dec | 19864181 |
Development of an enzyme-linked immunosorbent assay for metolcarb residueanalysis and investigation of matrix effects from different agriculturalproducts. | Anal Bioanal Chem | 2009 Aug | 19575189 |
Atmospheric pressure glow discharge desorption mass spectrometry for rapidscreening of pesticides in food. | Rapid Commun Mass Spectrom | 2008 Sep | 18697232 |
Metal-organic frameworks supported surface-imprinted nanoparticles for thesensitive detection of metolcarb. | None | None | 26735869 |
Targets
- 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
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- 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
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088