Basic Info

Common NameThiofanox(F04035)
2D Structure
Description

Thiofanox 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 IDF04035
CAS Number39196-18-4
PubChem CID5364932
FormulaC9H18N2O2S
IUPAC Name

[(E)-(3,3-dimethyl-1-methylsulfanylbutan-2-ylidene)amino] N-methylcarbamate

InChI Key

FZSVSABTBYGOQH-XFFZJAGNSA-N

InChI

InChI=1S/C9H18N2O2S/c1-9(2,3)7(6-14-5)11-13-8(12)10-4/h6H2,1-5H3,(H,10,12)/b11-7-

Canonical SMILES

CC(C)(C)C(=NOC(=O)NC)CSC

Isomeric SMILES

CC(C)(C)/C(=N\OC(=O)NC)/CSC

Synonyms
        
            Thiofanocarb
        
            Dacamox
        
            Benelux
        
            THIOFANOX
        
            Thiophanox
        
            Caswell No. 368BB
        
            3,3-Dimethyl-1-(methylthio)butanone-O-(N-methylcarbamoyl)oxime
        
            RCRA waste number P045
        
            Thiofanox [ANSI:BSI:ISO]
        
            Diamond shamrock DS-15647
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassOxime carbamates
Intermediate Tree NodesNot available
Direct ParentOxime carbamates
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOxime carbamate - Ketoxime - Carbonic acid derivative - Dialkylthioether - Sulfenyl compound - Thioether - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as oxime carbamates. These are oxime ether derivatives with the general formula CC(R)=NOC(=O)N(R')R\", where R-R\" = H or organyl.

Properties

Property NameProperty Value
Molecular Weight218.315
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity221
Monoisotopic Mass218.109
Exact Mass218.109
XLogP2.2
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9570
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5355
P-glycoprotein SubstrateNon-substrate0.5839
P-glycoprotein InhibitorNon-inhibitor0.6700
Non-inhibitor0.9084
Renal Organic Cation TransporterNon-inhibitor0.8916
Distribution
Subcellular localizationMitochondria0.5799
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7918
CYP450 2D6 SubstrateNon-substrate0.8224
CYP450 3A4 SubstrateNon-substrate0.5206
CYP450 1A2 InhibitorNon-inhibitor0.7266
CYP450 2C9 InhibitorNon-inhibitor0.7973
CYP450 2D6 InhibitorNon-inhibitor0.8744
CYP450 2C19 InhibitorNon-inhibitor0.6782
CYP450 3A4 InhibitorNon-inhibitor0.9669
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9532
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9878
Non-inhibitor0.9635
AMES ToxicityNon AMES toxic0.7090
CarcinogensCarcinogens 0.5657
Fish ToxicityHigh FHMT0.7795
Tetrahymena Pyriformis ToxicityHigh TPT0.5365
Honey Bee ToxicityHigh HBT0.7659
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityI0.7747
Carcinogenicity (Three-class)Non-required0.6368

Model Value Unit
Absorption
Aqueous solubility-1.5575LogS
Caco-2 Permeability1.2137LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.4413LD50, mol/kg
Fish Toxicity0.5286pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1201pIGC50, 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