Basic Info

Common NameDesmedipham(F03986)
2D Structure
Description

Desmedipham is a selective, systemic post-emergence herbicide of the phenyl carbamate and biscarbamate classes. 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. Desmedipham was developed by Schering AG and approved for use in the United States in 1970. It is commonly used in beet and strawberry crops to protect against weeds, often in comination with Phenmedipham under the trade names Betanal or Betamax. (L795)

FRCD IDF03986
CAS Number13684-56-5
PubChem CID24743
FormulaC16H16N2O4
IUPAC Name

[3-(ethoxycarbonylamino)phenyl] N-phenylcarbamate

InChI Key

WZJZMXBKUWKXTQ-UHFFFAOYSA-N

InChI

InChI=1S/C16H16N2O4/c1-2-21-15(19)18-13-9-6-10-14(11-13)22-16(20)17-12-7-4-3-5-8-12/h3-11H,2H2,1H3,(H,17,20)(H,18,19)

Canonical SMILES

CCOC(=O)NC1=CC(=CC=C1)OC(=O)NC2=CC=CC=C2

Isomeric SMILES

CCOC(=O)NC1=CC(=CC=C1)OC(=O)NC2=CC=CC=C2

Synonyms
        
            Schering 38107
        
            DESMEDIPHAM
        
            13684-56-5
        
            Bentanex
        
            Betanex
        
            Synbetan D
        
            Betanal AM
        
            Betanal AM 11
        
            Caswell No. 447AAA
        
            Desmediphame [ISO-French]
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylcarbamic acid esters
Intermediate Tree NodesNot available
Direct ParentPhenylcarbamic acid esters
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylcarbamic acid ester - 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 phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Properties

Property NameProperty Value
Molecular Weight300.314
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Complexity369
Monoisotopic Mass300.111
Exact Mass300.111
XLogP3.4
Formal Charge0
Heavy Atom Count22
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+0.9197
Human Intestinal AbsorptionHIA+0.9859
Caco-2 PermeabilityCaco2-0.5403
P-glycoprotein SubstrateNon-substrate0.7003
P-glycoprotein InhibitorNon-inhibitor0.7048
Non-inhibitor0.7580
Renal Organic Cation TransporterNon-inhibitor0.9109
Distribution
Subcellular localizationMitochondria0.8907
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7562
CYP450 2D6 SubstrateNon-substrate0.7215
CYP450 3A4 SubstrateNon-substrate0.5741
CYP450 1A2 InhibitorInhibitor0.7758
CYP450 2C9 InhibitorNon-inhibitor0.7233
CYP450 2D6 InhibitorNon-inhibitor0.8794
CYP450 2C19 InhibitorInhibitor0.6994
CYP450 3A4 InhibitorNon-inhibitor0.8124
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5058
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9423
Non-inhibitor0.8892
AMES ToxicityAMES toxic0.6482
CarcinogensNon-carcinogens0.7928
Fish ToxicityHigh FHMT0.9915
Tetrahymena Pyriformis ToxicityHigh TPT0.9932
Honey Bee ToxicityLow HBT0.5995
BiodegradationNot ready biodegradable0.9305
Acute Oral ToxicityIV0.6344
Carcinogenicity (Three-class)Non-required0.4577

Model Value Unit
Absorption
Aqueous solubility-4.5676LogS
Caco-2 Permeability0.8101LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5264LD50, mol/kg
Fish Toxicity0.8098pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4980pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Cucurbits-Inedible PeelBritain0.05mg/kg
Other SolanaceaBritain0.05mg/kg
Other Small Fruit & Berries (Other Than Wild)Britain0.05mg/kg
WatermelonsBritain0.05mg/kg
SquashesBritain0.05mg/kg
MelonsBritain0.05mg/kg
Other Cucurbits-Edible PeelBritain0.05mg/kg
CourgettesBritain0.05mg/kg
GherkinsBritain0.05mg/kg
CucumbersBritain0.05mg/kg
OkraBritain0.05mg/kg
AuberginesBritain0.05mg/kg
Chili PeppersBritain0.05mg/kg
PeppersBritain0.05mg/kg
TomatoesBritain0.05mg/kg
Other Bulb VegetablesBritain0.05mg/kg
Spring OnionsBritain0.05mg/kg
ShallotsBritain0.05mg/kg
OnionsBritain0.05mg/kg
GarlicBritain0.05mg/kg

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
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular Weight:
55913.915 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]