| Revision as of 16:22, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476917548 of page 1,3-Dichloropropene for the Chem/Drugbox validation project (updated: 'ChEBI'). |
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{{distinguish|1,3-dichloropropane}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use dmy dates|date=June 2023}} |
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{{chembox |
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{{Chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 456494933 |
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|Watchedfields = changed |
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| ImageFileL1 = Trans-1,3-Dichloropropene.svg |
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|verifiedrevid = 477205208 |
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| ImageSizeL1 = 130px |
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|ImageFileL1 = Trans-1,3-Dichloropropene.svg |
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| ImageNameL1 = Skeletal formula of the trans isomer |
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|ImageSizeL1 = 120px |
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| ImageFileR1 = Cis-1,3-Dichloropropene.svg |
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|ImageNameL1 = Skeletal formula of the trans isomer |
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| ImageSizeR1 = 120px |
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|ImageFileR1 = Cis-1,3-Dichloropropene.svg |
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| ImageNameR1 = Skeletal formula of the cis isomer |
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|ImageSizeR1 = 120px |
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| ImageFileL2 = Trans-1,3-Dichloropropene-3D-balls.png |
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|ImageNameR1 = Skeletal formula of the cis isomer |
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| ImageSizeL2 = 120px |
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|ImageFileL2 = Trans-1,3-Dichloropropene-3D-balls.png |
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| ImageNameL2 = Ball-and-stick model of the trans isomer |
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|ImageSizeL2 = 120px |
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| ImageFileR2 = Cis-1,3-Dichloropropene-3D-balls.png |
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|ImageNameL2 = Ball-and-stick model of the trans isomer |
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| ImageSizeR2 = 120px |
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|ImageFileR2 = Cis-1,3-Dichloropropene-3D-balls.png |
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| ImageNameR2 = Ball-and-stick model of the cis isomer |
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|ImageSizeR2 = 120px |
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| IUPACName = 1,3-dichloroprop-1-ene |
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|ImageNameR2 = Ball-and-stick model of the cis isomer |
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| SystematicName = 1-Propene, 1,3-dichloro-, (1E)- |
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|PIN = 1,3-Dichloroprop-1-ene |
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| OtherNames = 1,3-D, Dorlone, Nematox, Telone, Nemex, cis-Dichloropropene, Di-Trapex CP, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 3-dichloropropylene, 3-D, DCP |
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|OtherNames = AQL Agrocelhone, DD92, 1,3-D, Dorlone, Nematox, Telone,<ref name="Martin-2003">{{cite journal | last=Martin | first=Frank N. | title=Development of Alternative Strategies for Management of Soilborne Pathogens Currently Controlled with Methyl Bromide | journal=] | publisher=] | volume=41 | issue=1 | year=2003 | issn=0066-4286 | doi=10.1146/annurev.phyto.41.052002.095514 | pages=325–350| pmid=14527332 }}</ref><ref name="Telone-to-Telos" /> Nemex, cis-Dichloropropene, Di-Trapex CP, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 1,3-dichloropropylene, 3-D, DCP, 3-Chloroallyl chloride |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23117 |
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|ChemSpiderID = 23117 |
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| InChIKey = UOORRWUZONOOLO-OWOJBTEDBJ |
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|InChIKey = UOORRWUZONOOLO-OWOJBTEDBJ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ |
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|StdInChI = 1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UOORRWUZONOOLO-OWOJBTEDSA-N |
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|StdInChIKey = UOORRWUZONOOLO-OWOJBTEDSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 542-75-6 |
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|CASNo = 542-75-6 |
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| EINECS = 208-826-5 |
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|EINECS = 208-826-5 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| EINECSCASNO = |
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|ChEMBL = 155926 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 155926 |
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|PubChem = 24726 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 24726 |
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|UNII = 9H780918D0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|SMILES = Cl=CCCl |
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| UNII = 9H780918D0 |
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|InChI = 1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ |
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| SMILES = Cl=CCCl |
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|RTECS = UC8310000 |
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| InChI = 1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ |
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|UNNumber = 2047 |
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| RTECS = UC8310000 |
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| MeSHName = 1,3-dichloro-1-propene |
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|MeSHName = 1,3-dichloro-1-propene |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 18624 |
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|ChEBI = 18918 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C18627 |
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|KEGG = C18627 |
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| ATCCode_prefix = |
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| ATCCode_suffix = |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>3</sub>H<sub>4</sub>Cl<sub>2</sub> |
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| MolarMass = 110.97 g/mol |
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| Appearance = Colorless to straw-colored liquid, sweet chloroform-like odor |
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| Density = 1.217 g/mL (cis); 1.224 g/mL (trans) |
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| MeltingPt = -84.5 °C |
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| Melting_notes = |
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| BoilingPt = 104 °C (cis); 112 °C (trans) |
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| Boiling_notes = |
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| Solubility = 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C |
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| SolubleOther = |
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| Solvent = |
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| LogP = 1.82 |
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| VaporPressure = 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans) |
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| HenryConstant = |
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| AtmosphericOHRateConstant = |
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| pKa = |
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| pKb = }} |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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| Coordination = |
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| MolShape = }} |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHf = |
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| DeltaHc = |
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| Entropy = |
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| HeatCapacity = }} |
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| Section5 = {{Chembox Pharmacology |
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| AdminRoutes = |
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| Bioavail = |
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| Metabolism = |
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| HalfLife = |
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| ProteinBound = |
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| Excretion = |
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| Legal_status = |
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| Legal_US = |
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| Legal_AU = |
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| Legal_CA = |
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| PregCat = |
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| PregCat_AU = |
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| PregCat_US = }} |
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| Section6 = {{Chembox Explosive |
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| ShockSens = |
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| FrictionSens = |
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| ExplosiveV = |
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| REFactor = }} |
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| Section7 = {{Chembox Hazards |
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| EUClass = T,N |
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| EUIndex = 208-826-5 |
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| MainHazards = |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| NFPA-O = |
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| RPhrases = 10-20/21-25-36/37/38-43-50/53 |
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| SPhrases = (1/2-)-36/37-45-60-61 |
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| RSPhrases = |
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| FlashPt = 28 °C |
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| Autoignition = > 500 °C |
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| ExploLimits = 5.3% - 14.5% (80 °C) |
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| PEL = 1}} |
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| Section8 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunctn = |
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| Function = |
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| OtherCpds = }} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = C<sub>3</sub>H<sub>4</sub>Cl<sub>2</sub> |
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|MolarMass = 110.97 g/mol |
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|Appearance = Colorless to straw-colored liquid |
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|Odor = sweet, ]-like |
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|Density = 1.217 g/mL (cis); 1.224 g/mL (trans) |
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|MeltingPtC = -84.5 |
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|BoilingPtC = 104 |
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|BoilingPt_notes = (cis); 112 °C (trans) |
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|Solubility = 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C |
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|LogP = 1.82 |
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|VaporPressure = 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans) |
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}} |
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|Section3={{Chembox Hazards |
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|NFPA-H = 2 |
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|NFPA-F = 3 |
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|NFPA-R = 0 |
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|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|301|302|305|311|315|317|319|331|332|335|410}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|272|273|280|301+310|302+352|303+361+353|304+312|304+340|305+351+338|311|312|321|322|330|331|332+313|333+313|337+313|361|362|363|370+378|391|403+233|403+235|405|501}} |
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|FlashPtC = 28 |
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|AutoignitionPt = > |
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|AutoignitionPtC = 500 |
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|ExploLimits = 5.3% – 14.5% (80 °C) |
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|PEL = none<ref name=PGCH>{{PGCH|0199}}</ref> |
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|REL = Ca TWA 1 ppm (5 mg/m<sup>3</sup>) <ref name=PGCH/> |
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|IDLH = Ca <ref name=PGCH/> |
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}} |
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}} |
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'''1,3-Dichloropropene''', sold under diverse trade names, is an ] with the formula {{chem2|C3H4Cl2}}. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant ] and ]. It is widely used in the US and other countries, but is banned in 34 countries (including the ]).<ref>, ''Official Journal of the European Union'', 13 May 2022.</ref> |
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==Production, chemical properties, biodegradation== |
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It is a byproduct in the ] of ] to make ].<ref name="Ullmann">{{Citation |last1=Krähling |first1=Ludger |title=Allyl Compounds |date=2000-06-15 |url=https://doi.org/10.1002/14356007.a01_425 |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry |place=Weinheim, Germany |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |doi=10.1002/14356007.a01_425 |access-date=2022-03-18 |last2=Krey |first2=Jürgen |last3=Jakobson |first3=Gerald |last4=Grolig |first4=Johann |last5=Miksche |first5=Leopold|isbn=3527306730 }}</ref> |
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It is usually obtained as a mixture of the ], called (''Z'')-1,3-dichloropropene, and (''E'')-1,3-dichloropropene. Although it was first applied in agriculture in the 1950s, at least two biodegradation pathways have evolved. One pathway degrades the chlorocarbon to ] via chloroacrylic acid.<ref>{{Cite journal |last1=Poelarends |first1=Gerrit J. |last2=Whitman |first2=Christian P. |date=2004-10-01 |title=Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes |url=https://www.sciencedirect.com/science/article/pii/S004520680400029X |journal=Bioorganic Chemistry |series=Mechanistic Enzymology |language=en |volume=32 |issue=5 |pages=376–392 |doi=10.1016/j.bioorg.2004.05.006 |pmid=15381403 |issn=0045-2068}}</ref> |
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==Safety== |
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The ]-] for 1,3-dichloropropene (DCP) is 1 ppm.<ref name=Ullmann2>Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. {{doi|10.1002/14356007.a14_263}}</ref> It is a contact irritant. A wide range of complications have been reported.<ref name="atsdr.cdc.gov">{{Cite web|url=https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=835&tid=163|title = ToxFAQs – Letter A {{pipe}} Toxic Substance Portal {{pipe}} ATSDR}}</ref> |
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===Carcinogenicity=== |
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Evidence for the ]icity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. In the US, the ] (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. In California, the ] has determined that 1,3-dichloropropene is a carcinogen, and in 2022 established a No Significant Risk Level (NSRL) of 3.7 micrograms/day.<ref>{{Cite web |date=2022-06-21 |title=Proposition 65: No Significant Risk Level for 1,3-Dichloropropene (1,3-D) |url=https://oehha.ca.gov/proposition-65/crnr/proposition-65-no-significant-risk-level-13-dichloropropene-13-d |access-date=2022-10-26 |website=oehha.ca.gov}}</ref> The ] (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.<ref name="atsdr.cdc.gov"/> |
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==Use== |
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1,3-Dichloropropene is used as a pesticide in the following crops:<ref>{{Cite web |title=National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound |url=http://ca.water.usgs.gov/pnsp/crop/ |url-status=dead |archive-url=https://web.archive.org/web/20070410025543/http://ca.water.usgs.gov/pnsp/crop/ |archive-date=2007-04-10 |publisher=United States Geological Survey}}</ref> |
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{| class="wikitable" |
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|+ 1,3-Dichloropropene Use in Crops |
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! Crop !! Pounds (lb) !! Primary Pesticide? |
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| Tobacco |
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| 12,114,887 || Yes |
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| Potatoes |
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| 12,044,736 || Yes |
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| Sugar Beets |
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| 5,799,613 || Yes |
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| Cotton |
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| 3,735,543 || Yes |
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| Peanuts |
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| 3,463,003 || Yes |
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| Sweet Potatoes |
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| 1,210,872 || Yes |
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| Onions |
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| 674,183 || Yes |
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| Carrots |
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| 531,752 || Yes |
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| Watermelons |
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| 133,801 || No |
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| Cantaloups |
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| 121,395 || No |
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| Cucumbers |
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| 76,735 || No |
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| Strawberries |
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| 71,753 || No |
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| Sweet Peppers |
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| 28,247 || No |
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| Melons |
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| 12,471 || No |
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| Blueberries |
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| 3,090 || No |
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| Asparagus |
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| 1,105 || No |
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==Contamination== |
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The ] has extensive contamination information available.<ref>{{Cite web |date=September 2008 |title=TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES |url=http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf |website=Agency for Toxic Substances and Disease Registry}}</ref> |
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] with 1,3-Dichloropropene Contamination]] |
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==Market history== |
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Under the brand name Telone, 1,3-D was one of ]'s products until the merger into ]. Then it was spun off with ], and {{as of|2020|lc=yes}} has been licensed to Telos Ag Solutions and is no longer a Corteva product.<ref name="Martin-2003" /><ref name="Telone-to-Telos">{{cite web | title=Telone soil fumigant to be distributed by Telos Ag Solutions | website=Vegetable Growers News | date=2020-11-17 | url=http://vegetablegrowersnews.com/news/telone-soil-fumigant-to-be-distributed-by-telos-ag-solutions/ | access-date=2021-07-06}}</ref> |
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==References== |
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{{Reflist}} |
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==Further reading== |
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* |
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{{Authority control}} |
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{{DEFAULTSORT:Dichloropropene, 1, 3-}} |
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