2,4,5-Trichlorophenoxyacetic Acid

Basic Info

Common Name2,4,5-Trichlorophenoxyacetic Acid(F03895)
2D Structure
Description

2,4,5-Trichlorophenoxyacetic acid (also known as 2,4,5-T), a synthetic auxin, is a chlorophenoxy acetic acid herbicide used to defoliate broad-leafed plants. It was developed in the late 1940s and was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns. Human health effects from 2,4,5-T at low environmental doses or at biomonitored levels from low environmental exposures are unknown. Intentional overdoses and unintentional high dose occupational exposures to chlorophenoxy acid herbicides have resulted in weakness, headache, dizziness, nausea, abdominal pain, myotonia, hypotension, renal and hepatic injury, and delayed neuropathy. IARC considers the chlorophenoxyacetic acids group of chemicals as possibly carcinogenic to humans.

FRCD IDF03895
CAS Number93-76-5
PubChem CID1480
FormulaC8H5Cl3O3
IUPAC Name

2-(2,4,5-trichlorophenoxy)acetic acid

InChI Key

SMYMJHWAQXWPDB-UHFFFAOYSA-N

InChI

InChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13)

Canonical SMILES

C1=C(C(=CC(=C1Cl)Cl)Cl)OCC(=O)O

Isomeric SMILES

C1=C(C(=CC(=C1Cl)Cl)Cl)OCC(=O)O

Synonyms
        
            2,4,5-trichlorophenoxyacetic acid
        
            93-76-5
        
            Fortex
        
            2,4,5-T
        
            Trioxon
        
            Fence rider
        
            2-(2,4,5-trichlorophenoxy)acetic acid
        
            (2,4,5-Trichlorophenoxy)acetic acid
        
            BCF-Bushkiller
        
            Tippontormona
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenoxyacetic acid derivatives
Intermediate Tree NodesNot available
Direct ParentChlorophenoxyacetates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsChlorophenoxyacetate - Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic oxide - Organochloride - Hydrocarbon derivative - Organohalogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as chlorophenoxyacetates. These are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.

Properties

Property NameProperty Value
Molecular Weight255.475
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity212
Monoisotopic Mass253.93
Exact Mass253.93
XLogP3.3
Formal Charge0
Heavy Atom Count14
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+0.8557
Human Intestinal AbsorptionHIA+0.9816
Caco-2 PermeabilityCaco2+0.6887
P-glycoprotein SubstrateNon-substrate0.7235
P-glycoprotein InhibitorNon-inhibitor0.8575
Non-inhibitor0.9401
Renal Organic Cation TransporterNon-inhibitor0.8826
Distribution
Subcellular localizationMitochondria0.9357
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8190
CYP450 2D6 SubstrateNon-substrate0.9047
CYP450 3A4 SubstrateNon-substrate0.6519
CYP450 1A2 InhibitorNon-inhibitor0.9183
CYP450 2C9 InhibitorNon-inhibitor0.9339
CYP450 2D6 InhibitorNon-inhibitor0.9594
CYP450 2C19 InhibitorNon-inhibitor0.9812
CYP450 3A4 InhibitorNon-inhibitor0.9559
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8594
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9632
Non-inhibitor0.9239
AMES ToxicityNon AMES toxic0.9650
CarcinogensNon-carcinogens0.8398
Fish ToxicityHigh FHMT0.8980
Tetrahymena Pyriformis ToxicityHigh TPT0.9987
Honey Bee ToxicityHigh HBT0.6451
BiodegradationNot ready biodegradable0.6648
Acute Oral ToxicityII0.7505
Carcinogenicity (Three-class)Non-required0.6930
Model Value Unit
Absorption
Aqueous solubility-2.4477LogS
Caco-2 Permeability1.0037LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7387LD50, mol/kg
Fish Toxicity0.4016pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8101pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus fruits0110000European Union0.01*30/12/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*30/12/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*30/12/2015
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*30/12/2015
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*30/12/2015
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*30/12/2015
Others (2)0110990European Union0.01*30/12/2015
Tree nuts0120000European Union0.02*30/12/2015
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*30/12/2015
Brazil nuts0120020European Union0.02*30/12/2015
Cashew nuts0120030European Union0.02*30/12/2015
Chestnuts0120040European Union0.02*30/12/2015
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*30/12/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*30/12/2015
Macadamias0120070European Union0.02*30/12/2015
Pecans (Hickory nuts,)0120080European Union0.02*30/12/2015
Pistachios0120100European Union0.02*30/12/2015
Walnuts0120110European Union0.02*30/12/2015
Others (2)0120990European Union0.02*30/12/2015
Pome fruits0130000European Union0.01*30/12/2015

References

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Enzyme-linked immunosorbent assay by image analysis using a charge-coupled devicearray detector.Anal Biochem1996 Jul 158660618
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Process of building biologically based dose-response models for developmental defects.Teratology1992 Dec1290158
[Toxicity and certain physiopathologic effects of 2,4,5-trichlorophenoxyacetic acid, an organo-chlorine herbicide, in the adult domestic quail (Coturnix coturnix japonica)].C R Seances Soc Biol Fil19826217874
Agent Orange toxicity: a quantitative perspective.Hum Toxicol19817348691
Conditioned taste aversion to saccharin induced by 2, 4, 5-trichlorophenoxyaceticacid in albino rats.Physiol Behav1977 Jul11803680
Embryotoxicity of chemical contaminants of foods.Food Cosmet Toxicol1971 Apr4934609