Basic Info

Common NameFenasulam(F03993)
2D Structure
Description

Fenasulam 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 IDF03993
CAS Number78357-48-9
PubChem CID12923188
FormulaC17H17ClN2O6S
IUPAC Name

methyl N-[4-[[2-(4-chloro-2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate

InChI Key

LFDDUUFFHPNIPZ-UHFFFAOYSA-N

InChI

InChI=1S/C17H17ClN2O6S/c1-11-9-12(18)3-8-15(11)26-10-16(21)19-13-4-6-14(7-5-13)27(23,24)20-17(22)25-2/h3-9H,10H2,1-2H3,(H,19,21)(H,20,22)

Canonical SMILES

CC1=C(C=CC(=C1)Cl)OCC(=O)NC2=CC=C(C=C2)S(=O)(=O)NC(=O)OC

Isomeric SMILES

CC1=C(C=CC(=C1)Cl)OCC(=O)NC2=CC=C(C=C2)S(=O)(=O)NC(=O)OC

Synonyms
        
            DTXSID1058183
        
            UNII-99SO9089L9
        
            99SO9089L9
        
            78357-48-9
        
            Fenasulam [ISO]
        
            SCHEMBL134430
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzenesulfonamides
Intermediate Tree NodesNot available
Direct ParentBenzenesulfonamides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzenesulfonamide - Anilide - Benzenesulfonyl group - Phenoxy compound - Phenol ether - N-arylamide - Alkyl aryl ether - Chlorobenzene - Halobenzene - Toluene - Aryl halide - Aryl chloride - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Aminosulfonyl compound - Secondary carboxylic acid amide - Carboxamide group - Carbonic acid derivative - Carboxylic acid derivative - Ether - Hydrocarbon derivative - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Properties

Property NameProperty Value
Molecular Weight412.841
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Complexity615
Monoisotopic Mass412.05
Exact Mass412.05
XLogP2.9
Formal Charge0
Heavy Atom Count27
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+0.5599
Human Intestinal AbsorptionHIA+0.9313
Caco-2 PermeabilityCaco2-0.6072
P-glycoprotein SubstrateNon-substrate0.7363
P-glycoprotein InhibitorNon-inhibitor0.7077
Non-inhibitor0.6829
Renal Organic Cation TransporterNon-inhibitor0.9008
Distribution
Subcellular localizationMitochondria0.5076
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5941
CYP450 2D6 SubstrateNon-substrate0.8136
CYP450 3A4 SubstrateSubstrate0.5857
CYP450 1A2 InhibitorNon-inhibitor0.5086
CYP450 2C9 InhibitorInhibitor0.7083
CYP450 2D6 InhibitorNon-inhibitor0.7594
CYP450 2C19 InhibitorInhibitor0.8420
CYP450 3A4 InhibitorInhibitor0.7240
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.9312
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9875
Non-inhibitor0.8697
AMES ToxicityNon AMES toxic0.6516
CarcinogensNon-carcinogens0.6681
Fish ToxicityHigh FHMT0.9804
Tetrahymena Pyriformis ToxicityHigh TPT0.9643
Honey Bee ToxicityLow HBT0.7436
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.6258
Carcinogenicity (Three-class)Non-required0.5800

Model Value Unit
Absorption
Aqueous solubility-3.9776LogS
Caco-2 Permeability0.4894LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3742LD50, mol/kg
Fish Toxicity1.2293pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5061pIGC50, 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