Basic Info

Common NameTrimethacarb(F04036)
2D Structure
Description

Trimethacarb 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 IDF04036
CAS Number2686-99-9
PubChem CID17592
FormulaC11H15NO2
IUPAC Name

(3,4,5-trimethylphenyl) N-methylcarbamate

InChI Key

AUQAUAIUNJIIEP-UHFFFAOYSA-N

InChI

InChI=1S/C11H15NO2/c1-7-5-10(14-11(13)12-4)6-8(2)9(7)3/h5-6H,1-4H3,(H,12,13)

Canonical SMILES

CC1=CC(=CC(=C1C)C)OC(=O)NC

Isomeric SMILES

CC1=CC(=CC(=C1C)C)OC(=O)NC

Synonyms
        
            2686-99-9
        
            Methylcarbamic acid 3,4,5-trimethylphenyl ester
        
            3,4,5-Trimethylphenyl methylcarbamate
        
            Trimethacarb
        
            3,4,5-Trimethacarb
        
            Shell 8530
        
            Landrin 1
        
            Shell SD-8530
        
            OMS-597
        
            Trimethacarb [ANSI]
        
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 - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - 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 Weight193.246
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity194
Monoisotopic Mass193.11
Exact Mass193.11
XLogP2.7
Formal Charge0
Heavy Atom Count14
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+0.9690
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7931
P-glycoprotein SubstrateNon-substrate0.8587
P-glycoprotein InhibitorNon-inhibitor0.9362
Non-inhibitor0.9698
Renal Organic Cation TransporterNon-inhibitor0.9069
Distribution
Subcellular localizationMitochondria0.7904
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7525
CYP450 2D6 SubstrateSubstrate0.8498
CYP450 3A4 SubstrateSubstrate0.5616
CYP450 1A2 InhibitorNon-inhibitor0.5270
CYP450 2C9 InhibitorNon-inhibitor0.9634
CYP450 2D6 InhibitorNon-inhibitor0.9127
CYP450 2C19 InhibitorNon-inhibitor0.8918
CYP450 3A4 InhibitorNon-inhibitor0.9047
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7772
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9338
Non-inhibitor0.9470
AMES ToxicityAMES toxic0.7160
CarcinogensNon-carcinogens0.8614
Fish ToxicityHigh FHMT0.7691
Tetrahymena Pyriformis ToxicityHigh TPT0.9218
Honey Bee ToxicityHigh HBT0.8213
BiodegradationNot ready biodegradable0.7579
Acute Oral ToxicityII0.8993
Carcinogenicity (Three-class)Non-required0.5836

Model Value Unit
Absorption
Aqueous solubility-2.4683LogS
Caco-2 Permeability1.7559LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7923LD50, mol/kg
Fish Toxicity1.4668pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0614pIGC50, ug/L

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
  1. 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
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088