Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,3-Dichloropropene: Difference between pages

{{distinguish|1,3-dichloropropane}}

{{Use dmy dates|date=June 2023}}

{{Chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 477205208

|ImageFileL1 = Trans-1,3-Dichloropropene.svg

|ImageSizeL1 = 120px

|ImageNameL1 = Skeletal formula of the trans isomer

|ImageFileR1 = Cis-1,3-Dichloropropene.svg

|ImageSizeR1 = 120px

|ImageNameR1 = Skeletal formula of the cis isomer

|ImageFileL2 = Trans-1,3-Dichloropropene-3D-balls.png

|ImageSizeL2 = 120px

|ImageNameL2 = Ball-and-stick model of the trans isomer

|ImageFileR2 = Cis-1,3-Dichloropropene-3D-balls.png

|ImageSizeR2 = 120px

|ImageNameR2 = Ball-and-stick model of the cis isomer

|PIN = 1,3-Dichloroprop-1-ene

|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=[[Annual Review of Phytopathology]] | publisher=[[Annual Reviews (publisher)|Annual Reviews]] | 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

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 23117

|InChIKey = UOORRWUZONOOLO-OWOJBTEDBJ

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = UOORRWUZONOOLO-OWOJBTEDSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 542-75-6

|EINECS = 208-826-5

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 155926

|PubChem = 24726

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 9H780918D0

|SMILES = Cl[C@H]=CCCl

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

|RTECS = UC8310000

|UNNumber = 2047

|MeSHName = 1,3-dichloro-1-propene

|ChEBI_Ref = {{ebicite|changed|EBI}}

|ChEBI = 18918

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = C18627

|Section2={{Chembox Properties

|Formula = C₃H₄Cl₂

|MolarMass = 110.97 g/mol

|Appearance = Colorless to straw-colored liquid

|Odor = sweet, [[chloroform]]-like

|Density = 1.217 g/mL (cis); 1.224 g/mL (trans)

|MeltingPtC = -84.5

|BoilingPtC = 104

|BoilingPt_notes = (cis); 112&nbsp;°C (trans)

|Solubility = 2.18 g/L (cis) @ 25&nbsp;°C; 2.32 g/L (trans) @ 25&nbsp;°C

|LogP = 1.82

|VaporPressure = 34.4 mm Hg @ 25&nbsp;°C (cis); 23.0 mm Hg @ 25&nbsp;°C (trans)

}}

|Section3={{Chembox Hazards

|NFPA-H = 2

|NFPA-F = 3

|NFPA-R = 0

|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|226|301|302|305|311|315|317|319|331|332|335|410}}

|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}}

|FlashPtC = 28

|AutoignitionPt = >

|AutoignitionPtC = 500

|ExploLimits = 5.3% – 14.5% (80&nbsp;°C)

|PEL = none<ref name=PGCH>{{PGCH|0199}}</ref>

|REL = Ca TWA 1 ppm (5 mg/m³) [skin]<ref name=PGCH/>

|IDLH = Ca [N.D.]<ref name=PGCH/>

}}

}}

'''1,3-Dichloropropene''', sold under diverse trade names, is an [[organochlorine compound]] 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 [[fumigant]] and [[nematicide]]. It is widely used in the US and other countries, but is banned in 34 countries (including the [[European Union]]).<ref>[https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32022R0740&from=EN COMMISSION DECISION of 13 May 2022 concerning the non-approval of the active substance 1,3-dichloropropene], ''Official Journal of the European Union'', 13 May 2022.</ref>

==Production, chemical properties, biodegradation==

It is a byproduct in the [[chlorination reaction|chlorination]] of [[propene]] to make [[allyl chloride]].<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>

It is usually obtained as a mixture of the [[Cis-trans isomerism|geometric isomers]], 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 [[acetaldehyde]] 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>

==Safety==

The [[Threshold limit value|TLV]]-[[Time-weighted average (PEL)|TWA]] 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>

===Carcinogenicity===

Evidence for the [[carcinogen]]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 [[United States Department of Health and Human Services|Department of Health and Human Services]] (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. In California, the [[California Office of Environmental Health Hazard Assessment|Office of Environmental Health Hazard Assessment]] 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 [[International Agency for Research on Cancer]] (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"/>

==Use==

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>

{| class="wikitable"

|+ 1,3-Dichloropropene Use in Crops

! Crop !! Pounds (lb) !! Primary Pesticide?

|-

| Tobacco

| 12,114,887 || Yes

|-

| Potatoes

| 12,044,736 || Yes

|-

| Sugar Beets

| 5,799,613 || Yes

|-

| Cotton

| 3,735,543 || Yes

|-

| Peanuts

| 3,463,003 || Yes

|-

| Sweet Potatoes

| 1,210,872 || Yes

|-

| Onions

| 674,183 || Yes

|-

| Carrots

| 531,752 || Yes

|-

| Watermelons

| 133,801 || No

|-

| Cantaloups

| 121,395 || No

|-

| Cucumbers

| 76,735 || No

|-

| Strawberries

| 71,753 || No

|-

| Sweet Peppers

| 28,247 || No

|-

| Melons

| 12,471 || No

|-

| Blueberries

| 3,090 || No

|-

| Asparagus

| 1,105 || No

|}

==Contamination==

The [[Agency for Toxic Substances and Disease Registry|ATSDR]] 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>

[[Image:Frequency of npl sites with DCP contam.png|frame|none|Frequency of [[National Priorities List|NPL Sites]] with 1,3-Dichloropropene Contamination]]

==Market history==

Under the brand name Telone, 1,3-D was one of [[Dow AgroSciences]]'s products until the merger into [[DowDuPont]]. Then it was spun off with [[Corteva]], 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>

==References==

{{Reflist}}

*[https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=835&tid=163 ATSDR ToxFAQs: Dichloropropenes]

*[https://web.archive.org/web/20070410025543/http://ca.water.usgs.gov/pnsp/crop/ USGS Pesticide National Synthesis Project – Crop & Compound]

==Further reading==

*[http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf ATSDR Toxicological Profile (9.2 MB)]

*[https://www.cdc.gov/niosh/npg/npgd0199.html CDC – NIOSH Pocket Guide to Chemical Hazards]

{{Authority control}}

{{DEFAULTSORT:Dichloropropene, 1, 3-}}

[[Category:Pesticides]]

[[Category:Chloroalkenes]]

[[Category:IARC Group 2B carcinogens]]

[[Category:Fumigants]]

[[Category:Sweet-smelling chemicals]]