Basic Info

Common NameButacarb(F03968)
2D Structure
Description

Butacarb 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 IDF03968
CAS Number2655-19-8
PubChem CID17564
FormulaC16H25NO2
IUPAC Name

(3,5-ditert-butylphenyl) N-methylcarbamate

InChI Key

SLZWBCGZQRRUNG-UHFFFAOYSA-N

InChI

InChI=1S/C16H25NO2/c1-15(2,3)11-8-12(16(4,5)6)10-13(9-11)19-14(18)17-7/h8-10H,1-7H3,(H,17,18)

Canonical SMILES

CC(C)(C)C1=CC(=CC(=C1)OC(=O)NC)C(C)(C)C

Isomeric SMILES

CC(C)(C)C1=CC(=CC(=C1)OC(=O)NC)C(C)(C)C

Synonyms
        
            3,5-Di-t-butylphenylmethylcarbamate
        
            BUTACARB
        
            Butacarbe [French]
        
            Caswell No. 291B
        
            Butacarb [ISO:BSI]
        
            UNII-48SLE5Y118
        
            2655-19-8
        
            HSDB 2799
        
            BTS 14639
        
            EPA Pesticide Chemical Code 291300
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Phenylpropane - Phenoxy compound - 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
DescriptionThis 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 NameProperty Value
Molecular Weight263.381
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Complexity290
Monoisotopic Mass263.189
Exact Mass263.189
XLogP4.7
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+0.9427
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7208
P-glycoprotein SubstrateNon-substrate0.7984
P-glycoprotein InhibitorNon-inhibitor0.9318
Non-inhibitor0.9598
Renal Organic Cation TransporterNon-inhibitor0.9117
Distribution
Subcellular localizationMitochondria0.7315
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7685
CYP450 2D6 SubstrateSubstrate0.6304
CYP450 3A4 SubstrateSubstrate0.6471
CYP450 1A2 InhibitorNon-inhibitor0.7128
CYP450 2C9 InhibitorNon-inhibitor0.9078
CYP450 2D6 InhibitorNon-inhibitor0.8761
CYP450 2C19 InhibitorNon-inhibitor0.8747
CYP450 3A4 InhibitorNon-inhibitor0.8810
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7877
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9771
Non-inhibitor0.9637
AMES ToxicityNon AMES toxic0.7201
CarcinogensNon-carcinogens0.7989
Fish ToxicityHigh FHMT0.7848
Tetrahymena Pyriformis ToxicityHigh TPT0.9496
Honey Bee ToxicityHigh HBT0.8741
BiodegradationNot ready biodegradable0.9591
Acute Oral ToxicityIII0.7805
Carcinogenicity (Three-class)Non-required0.5611

Model Value Unit
Absorption
Aqueous solubility-3.4059LogS
Caco-2 Permeability1.6450LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2725LD50, mol/kg
Fish Toxicity0.8750pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4124pIGC50, 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