Basic Info

Common NameDichlormate(F03987)
2D Structure
Description

Dichlormate 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 IDF03987
CAS Number1966-58-1
PubChem CID16072
FormulaC9H9Cl2NO2
IUPAC Name

(3,4-dichlorophenyl)methyl N-methylcarbamate

InChI Key

DSVOTYIOPGIVPP-UHFFFAOYSA-N

InChI

InChI=1S/C9H9Cl2NO2/c1-12-9(13)14-5-6-2-3-7(10)8(11)4-6/h2-4H,5H2,1H3,(H,12,13)

Canonical SMILES

CNC(=O)OCC1=CC(=C(C=C1)Cl)Cl

Isomeric SMILES

CNC(=O)OCC1=CC(=C(C=C1)Cl)Cl

Synonyms
        
            Dichlormate [ISO]
        
            Benzenemethanol, 3,4-dichloro-, methylcarbamate
        
            Dichlormate
        
            Sirmate
        
            3,4-Sirmate
        
            Caswell No. 298A
        
            Caswell No. 301A
        
            UNII-XDA707PJIO
        
            3,4-DICHLOROBENZYL METHYLCARBAMATE
        
            Methylcarbamate 3,4-dichlorobenzyl ester
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzyloxycarbonyls
Intermediate Tree NodesNot available
Direct ParentBenzyloxycarbonyls
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzyloxycarbonyl - 1,2-dichlorobenzene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organochloride - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Properties

Property NameProperty Value
Molecular Weight234.076
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity201
Monoisotopic Mass233.001
Exact Mass233.001
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+0.9948
Human Intestinal AbsorptionHIA+0.9974
Caco-2 PermeabilityCaco2+0.6879
P-glycoprotein SubstrateNon-substrate0.8671
P-glycoprotein InhibitorNon-inhibitor0.9354
Non-inhibitor0.9217
Renal Organic Cation TransporterNon-inhibitor0.8441
Distribution
Subcellular localizationMitochondria0.8119
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7846
CYP450 2D6 SubstrateNon-substrate0.7439
CYP450 3A4 SubstrateNon-substrate0.5206
CYP450 1A2 InhibitorInhibitor0.9257
CYP450 2C9 InhibitorNon-inhibitor0.6995
CYP450 2D6 InhibitorNon-inhibitor0.8275
CYP450 2C19 InhibitorInhibitor0.5127
CYP450 3A4 InhibitorNon-inhibitor0.8575
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6058
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9471
Non-inhibitor0.9059
AMES ToxicityNon AMES toxic0.6648
CarcinogensNon-carcinogens0.8442
Fish ToxicityHigh FHMT0.8525
Tetrahymena Pyriformis ToxicityHigh TPT0.9989
Honey Bee ToxicityLow HBT0.5719
BiodegradationNot ready biodegradable0.9148
Acute Oral ToxicityIII0.8125
Carcinogenicity (Three-class)Non-required0.6409

Model Value Unit
Absorption
Aqueous solubility-3.3254LogS
Caco-2 Permeability1.8478LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1293LD50, mol/kg
Fish Toxicity1.8504pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1933pIGC50, 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