Diethofencarb

Basic Info

Common NameDiethofencarb(F03988)
2D Structure
Description

Diethofencarb 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 IDF03988
CAS Number87130-20-9
PubChem CID91742
FormulaC14H21NO4
IUPAC Name

propan-2-yl N-(3,4-diethoxyphenyl)carbamate

InChI Key

LNJNFVJKDJYTEU-UHFFFAOYSA-N

InChI

InChI=1S/C14H21NO4/c1-5-17-12-8-7-11(9-13(12)18-6-2)15-14(16)19-10(3)4/h7-10H,5-6H2,1-4H3,(H,15,16)

Canonical SMILES

CCOC1=C(C=C(C=C1)NC(=O)OC(C)C)OCC

Isomeric SMILES

CCOC1=C(C=C(C=C1)NC(=O)OC(C)C)OCC

Synonyms
        
            Diethofencarb
        
            87130-20-9
        
            powmil
        
            Powmyl WP
        
            Diethofencarb [ISO]
        
            Isopropyl 3,4-diethoxycarbanilate
        
            Isopropyl (3,4-diethoxyphenyl)carbamate
        
            UNII-421BLT77U4
        
            Isopropyl N-(3,4-diethoxyphenyl)carbamate
        
            1-Methylethyl (3,4-diethoxyphenyl)carbamate
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 - Phenol ether - Alkyl aryl ether - Carbamic acid ester - Carbonic acid derivative - Ether - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - 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 Weight267.325
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Complexity270
Monoisotopic Mass267.147
Exact Mass267.147
XLogP2.8
Formal Charge0
Heavy Atom Count19
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+0.7638
Human Intestinal AbsorptionHIA+0.9920
Caco-2 PermeabilityCaco2+0.6190
P-glycoprotein SubstrateNon-substrate0.7801
P-glycoprotein InhibitorNon-inhibitor0.7518
Non-inhibitor0.8387
Renal Organic Cation TransporterNon-inhibitor0.9332
Distribution
Subcellular localizationMitochondria0.8450
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7796
CYP450 2D6 SubstrateNon-substrate0.6405
CYP450 3A4 SubstrateSubstrate0.5757
CYP450 1A2 InhibitorInhibitor0.7700
CYP450 2C9 InhibitorNon-inhibitor0.7290
CYP450 2D6 InhibitorNon-inhibitor0.8794
CYP450 2C19 InhibitorInhibitor0.6042
CYP450 3A4 InhibitorNon-inhibitor0.8563
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5269
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9621
Non-inhibitor0.9102
AMES ToxicityAMES toxic0.5458
CarcinogensNon-carcinogens0.7284
Fish ToxicityHigh FHMT0.9878
Tetrahymena Pyriformis ToxicityHigh TPT0.9779
Honey Bee ToxicityHigh HBT0.6113
BiodegradationNot ready biodegradable0.9128
Acute Oral ToxicityIII0.7780
Carcinogenicity (Three-class)Non-required0.5957
Model Value Unit
Absorption
Aqueous solubility-3.4309LogS
Caco-2 Permeability1.2638LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7594LD50, mol/kg
Fish Toxicity0.7395pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2369pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PapayaJapan5. oppm
KiwifruitJapan5. oppm
BananaJapan5. oppm
Citrus fruits0110000European Union0.01*23/02/2017
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*23/02/2017
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*23/02/2017
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*23/02/2017
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*23/02/2017
Others (2)0110990European Union0.01*23/02/2017
Tree nuts0120000European Union0.01*23/02/2017
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.01*23/02/2017
Brazil nuts0120020European Union0.01*23/02/2017
Cashew nuts0120030European Union0.01*23/02/2017
Chestnuts0120040European Union0.01*23/02/2017
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*23/02/2017
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.01*23/02/2017
Macadamias0120070European Union0.01*23/02/2017
Pecans (Hickory nuts,)0120080European Union0.01*23/02/2017
Pistachios0120100European Union0.01*23/02/2017
Walnuts0120110European Union0.01*23/02/2017

References

TitleJournalDatePubmed ID
Decline patterns and risk assessment of 10 multi-class pesticides in young sproutamaranth (Amaranthus mangostanus) under greenhouse growing conditions.Environ Sci Pollut Res Int2017 Nov28918593
Contributing effect of various washing procedures and additives on the declinepattern of diethofencarb in crown daisy, a model of leafy vegetables.Food Chem2016 Jun 1526868560
Residues and dissipation kinetics of carbendazim and diethofencarb in tomato(Lycopersicon esculentum Mill.) and intake risk assessment.Regul Toxicol Pharmacol2016 Jun26995029
Extraction of carbamate pesticides in fruit samples by graphene reinforced hollowfibre liquid microextraction followed by high performance liquid chromatographic detection.Food Chem2014 Aug 1524679760
Dispersive liquid-liquid microextraction based on the solidification of afloating organic droplet for simultaneous analysis of diethofencarb andpyrimethanil in apple pulp and peel.Anal Bioanal Chem2011 Feb21174194
Screening preharvest/postharvest strategies to prevent fruit rot decay.Commun Agric Appl Biol Sci200718396828
Metabolism of diethofencarb (isopropyl 3,4-diethoxyphenylcarbamate) in rats:identification of metabolites in urine.J Agric Food Chem2004 Feb 1114759145
Clay-catalyzed nitration of a carbamate fungicide diethofencarb.J Agric Food Chem2003 Dec 1714664537
Metabolism of fungicide diethofencarb in grape (Vitis vinifera L.): definitiveidentification of thiolactic acid conjugated metabolites.J Agric Food Chem2003 Aug 2712926879
Focused microwave assistance for extracting some pesticide residues fromstrawberries into water before their determination by SPME/HPLC/DAD.J Agric Food Chem2001 Nov11714287
Solid phase microextraction of pesticide residues from strawberries.Food Addit Contam1999 Mar10492703
Effects of diethofencarb on thyroid function and hepaticUDP-glucuronyltransferase activity in rats.J Toxicol Sci1992 Aug1453498

Targets

Target Details

Cholinesterase

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
Target Details

Acetylcholinesterase

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