Trans-1,3-Dichloropropene

Basic Info

Common NameTrans-1,3-Dichloropropene(F04434)
2D Structure
Description

Trans-1,3-Dichloropropene, also known as trans-Telone or simply trans-1,3-D, is a colorless liquid with a sweet smell. It is one of 2 isomers of 1,3-D. Trans-1,3-Dichloropropene is widely used as a preplanting soil fumigant for the control of nematodes, and it has been available for agricultural use in many formulations (L893).

FRCD IDF04434
CAS Number10061-02-6
PubChem CID24726
FormulaC3H4Cl2
IUPAC Name

(E)-1,3-dichloroprop-1-ene

InChI Key

UOORRWUZONOOLO-OWOJBTEDSA-N

InChI

InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+

Canonical SMILES

C(C=CCl)Cl

Isomeric SMILES

C(/C=C/Cl)Cl

Synonyms
        
            1,3-Dichloropropylene
        
            1,3-DICHLOROPROPENE
        
            trans-1,3-Dichloropropene
        
            542-75-6
        
            10061-02-6
        
            Telone II
        
            Telone
        
            Nemex
        
            trans-1,3-Dichloropropylene
        
            Dorlone II
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganohalogen compounds
ClassVinyl halides
SubclassVinyl chlorides
Intermediate Tree NodesNot available
Direct ParentVinyl chlorides
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsChloroalkene - Haloalkene - Vinyl chloride - Hydrocarbon derivative - Organochloride - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.

Properties

Property NameProperty Value
Molecular Weight110.965
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Complexity31.9
Monoisotopic Mass109.969
Exact Mass109.969
XLogP1.7
Formal Charge0
Heavy Atom Count5
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+0.9814
Human Intestinal AbsorptionHIA+0.9973
Caco-2 PermeabilityCaco2+0.7517
P-glycoprotein SubstrateNon-substrate0.8793
P-glycoprotein InhibitorNon-inhibitor0.9718
Non-inhibitor0.9469
Renal Organic Cation TransporterNon-inhibitor0.8646
Distribution
Subcellular localizationMitochondria0.4212
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7923
CYP450 2D6 SubstrateNon-substrate0.7948
CYP450 3A4 SubstrateNon-substrate0.7307
CYP450 1A2 InhibitorNon-inhibitor0.5654
CYP450 2C9 InhibitorNon-inhibitor0.8355
CYP450 2D6 InhibitorNon-inhibitor0.9471
CYP450 2C19 InhibitorNon-inhibitor0.7165
CYP450 3A4 InhibitorNon-inhibitor0.9443
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7278
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9113
Non-inhibitor0.9707
AMES ToxicityAMES toxic0.9106
CarcinogensCarcinogens 0.8318
Fish ToxicityHigh FHMT0.7422
Tetrahymena Pyriformis ToxicityHigh TPT0.9791
Honey Bee ToxicityHigh HBT0.8736
BiodegradationNot ready biodegradable0.8486
Acute Oral ToxicityII0.7726
Carcinogenicity (Three-class)Warning0.4125
Model Value Unit
Absorption
Aqueous solubility-1.2364LogS
Caco-2 Permeability1.6232LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4042LD50, mol/kg
Fish Toxicity0.1567pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8629pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Mineral WatersJapan0.02 ppm
FruitNetherland0.05mg/kg

References

TitleJournalDatePubmed ID
Replacing methyl bromide with a combination of 1,3-dichloropropene and metamsodium for cucumber production in China.PLoS One2017 Nov 1629145472
Integrating ecosystem services into crop protection and pest management: Casestudy with the soil fumigant 1,3-dichloropropene and its use in tomato productionin Italy.Integr Environ Assess Manag2016 Oct26822540
Effect of Soil Fumigation on Degradation of Pendimethalin and Oxyfluorfen inLaboratory and Ginger Field Studies.J Agric Food Chem2016 Nov 2327787973
Mechanisms for 1,3-Dichloropropene Dissipation in Biochar-Amended Soils.J Agric Food Chem2016 Mar 3026954066
Dissipation kinetics of pre-plant pesticides in greenhouse-devoted soils.Sci Total Environ2016 Feb 126575632
Emissions of 1,3-Dichloropropene and Chloropicrin after Soil Fumigation underField Conditions.J Agric Food Chem2015 Jun 1026001417
Effect of co-formulation of 1,3-dichloropropene and chloropicrin on evaporativeemissions from soil.J Agric Food Chem2015 Jan 2125531174
Effect of films on 1,3-dichloropropene and chloropicrin emission, soilconcentration, and root-knot nematode control in a raised bed.J Agric Food Chem2013 Mar 1323343207
Managing root-knot nematodes and weeds with 1,3-dichloropropene as an alternativeto methyl bromide in cucumber crops in China.J Agric Food Chem2011 Mar 2321366311
Soil fate of agricultural fumigants in raised-bed, plasticulture systems in thesoutheastern United States.J Environ Qual2011 Jul-Aug21712590
Evaluation of 1,3-dichloropropene as a methyl bromide alternative in tomato cropsin China.J Agric Food Chem2010 Nov 1020939573
1,3-dichloropropene distribution and emission after gelatin capsule formulationapplication.J Agric Food Chem2010 Jan 1319908833
Efficacy of 1,3-dichloropropene gelatin capsule formulation for the control ofsoilborne pests.J Agric Food Chem2009 Sep 2319754171
Interactive effect of organic amendment and environmental factors on degradation of 1,3-dichloropropene and chloropicrin in soil.J Agric Food Chem2009 Oct 1419722521
Effects of manure and water applications on 1,3-dichloropropene and chloropicrin emissions in a field trial.J Agric Food Chem2009 Jun 2419459700
Effect of drip application of ammonium thiosulfate on fumigant degradation insoil columns.J Agric Food Chem2007 Oct 317848085
Dechlorination of chloropicrin and 1,3-dichloropropene by hydrogen sulfidespecies: redox and nucleophilic substitution reactions.J Agric Food Chem2006 Mar 2216536608
Dehalogenation of halogenated fumigants by polysulfide salts.J Agric Food Chem2006 Jul 2616848538
Transformation of chloropicrin and 1,3-dichloropropene by metam sodium in acombined application of fumigants.J Agric Food Chem2004 May 1915137846
Fumigation toxicity of volatile natural and synthetic cyanohydrins tostored-product pests and activity as soil fumigants.Pest Manag Sci2004 Aug15307677