Basic Info

Common NameDimetilan(F03990)
2D Structure
Description

Dimetilan 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 IDF03990
CAS Number644-64-4
PubChem CID12572
FormulaC10H16N4O3
IUPAC Name

[1-(dimethylcarbamoyl)-5-methylpyrazol-3-yl] N,N-dimethylcarbamate

InChI Key

RDBIYWSVMRVKSG-UHFFFAOYSA-N

InChI

InChI=1S/C10H16N4O3/c1-7-6-8(17-10(16)13(4)5)11-14(7)9(15)12(2)3/h6H,1-5H3

Canonical SMILES

CC1=CC(=NN1C(=O)N(C)C)OC(=O)N(C)C

Isomeric SMILES

CC1=CC(=NN1C(=O)N(C)C)OC(=O)N(C)C

Synonyms
        
            FLY Bands
        
            DIMETILAN
        
            Dimetilane
        
            Snip fly bands
        
            Snip Fly
        
            644-64-4
        
            Geigy gs-13332
        
            Dimetilan [BSI]
        
            Geigy 22870
        
            Caswell No. 496B
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzoles
SubclassPyrazoles
Intermediate Tree NodesNot available
Direct ParentPyrazoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsHeteroaromatic compound - Carbamic acid ester - Pyrazole - Carbonic acid derivative - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrazoles. These are compounds containing a pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms.

Properties

Property NameProperty Value
Molecular Weight240.263
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity306
Monoisotopic Mass240.122
Exact Mass240.122
XLogP0.6
Formal Charge0
Heavy Atom Count17
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+0.9810
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5575
P-glycoprotein SubstrateNon-substrate0.7395
P-glycoprotein InhibitorNon-inhibitor0.6469
Non-inhibitor0.9603
Renal Organic Cation TransporterNon-inhibitor0.9282
Distribution
Subcellular localizationMitochondria0.7199
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7240
CYP450 2D6 SubstrateNon-substrate0.7523
CYP450 3A4 SubstrateSubstrate0.5070
CYP450 1A2 InhibitorNon-inhibitor0.7435
CYP450 2C9 InhibitorNon-inhibitor0.9002
CYP450 2D6 InhibitorNon-inhibitor0.8997
CYP450 2C19 InhibitorNon-inhibitor0.8524
CYP450 3A4 InhibitorNon-inhibitor0.9612
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9541
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9395
Non-inhibitor0.8706
AMES ToxicityNon AMES toxic0.5208
CarcinogensNon-carcinogens0.8365
Fish ToxicityHigh FHMT0.9553
Tetrahymena Pyriformis ToxicityLow TPT0.6475
Honey Bee ToxicityLow HBT0.6908
BiodegradationReady biodegradable0.5594
Acute Oral ToxicityI0.7746
Carcinogenicity (Three-class)Non-required0.5715

Model Value Unit
Absorption
Aqueous solubility-1.6307LogS
Caco-2 Permeability1.2225LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.9516LD50, mol/kg
Fish Toxicity1.4614pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1545pIGC50, 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