| Revision as of 17:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444458332 of page 2,6-Dichlorobenzonitrile for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 17:24, 30 September 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,663 edits →Synthesis: link |
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{{Use dmy dates|date=April 2017}} |
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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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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443346098 |
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| verifiedrevid = 477212024 |
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| ImageFile = DCBN.png |
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| ImageFile = 2,6-Dichlorobenzonitrile Structural Formula V1.svg |
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| ImageSize = 130 |
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| ImageName = Skeletal formula |
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| ImageSize = 130 |
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| ImageName = Skeletal formula |
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| ImageFile1 = 2,6-Dichlorobenzonitrile.png |
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| ImageFile1 = 2,6-Dichlorobenzonitrile.png |
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| ImageSize1 = 170 |
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| ImageSize1 = 170 |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 2,6-Dichlorobenzonitrile |
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| PIN = 2,6-Dichlorobenzonitrile |
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| OtherNames = Dichlobanil, Dichlobenil |
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| OtherNames = Dichlobanil, Dichlobenil |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2923 |
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| ChemSpiderID = 2923 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChIKey = YOYAIZYFCNQIRF-UHFFFAOYSA-N |
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| StdInChIKey = YOYAIZYFCNQIRF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=1194-65-6 |
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| CASNo =1194-65-6 |
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| PubChem=3031 |
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| PubChem =3031 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 943 |
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| ChEBI = 943 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = N#Cc1c(Cl)cccc1Cl |
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| SMILES = N#Cc1c(Cl)cccc1Cl |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>7</sub>H<sub>3</sub>Cl<sub>2</sub>N |
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| Formula =C<sub>7</sub>H<sub>3</sub>Cl<sub>2</sub>N |
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| MolarMass=172.01 g/mol |
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| MolarMass =172.01 g/mol |
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| Appearance= white crystalline powder |
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| Appearance = white crystalline powder |
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| Density= 1.623 g/cm<sup>3</sup> |
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| Density = 1.623 g/cm<sup>3</sup> |
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| MeltingPt= 144.5 °C |
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| MeltingPtC = 144.5 |
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| MeltingPt_notes = |
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| BoilingPt= 279 °C |
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| BoilingPtC = 279 |
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| Solubility= insoluble |
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| Solubility = insoluble |
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|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPt= 126 °C |
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| FlashPtC = 126 |
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'''2,6-Dichlorobenzonitrile''' (DCBN or dichlobenil) is an ] with the ] C<sub>6</sub>H<sub>3</sub>Cl<sub>2</sub>CN. It is a white solid that is soluble in organic solvents. It is widely used as a ] and organic chemistry building block.<ref name= Ullmanns>Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 {{doi|10.1002/14356007.o28_o01}}</ref> |
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==Mechanism of action== |
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It has herbicidal properties killing young seedlings of both ] and ] species.<ref></ref> DCBN interferes with cellulose synthesis. DCBN adapted cell walls use minimal amounts of cellulose, instead relying on Ca<sup>2+</sup>-bridge pectates.<ref></ref> |
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==Safety== |
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In 1971 in the U.S. State of California, their department of agriculture reported, "Dichlobenil kills the roots of many species, but not all; further, the killing does not extend much beyond the portion actually soaked."<ref> |
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{{cite web |
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| title = Control of Tree Roots in Sewers and Drains |
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| publisher = California Agriculture |
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| pages = 14 |
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| date = 1971 |
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| accessdate = 13 September 2015 |
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| url = https://ucanr.edu/repositoryfiles/ca2511p13-63902.pdf}}</ref> |
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In 1996, the University of California's Statewide Integrated Pest Management Project reported: <blockquote>Dosages were difficult to control... and as a result soaking or spraying methods are no longer used. <br> The current application method involves applying metam-sodium products in foam carriers (similar to shaving cream).<ref> |
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{{cite web |
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| title = Control of Tree Roots in Sewers and Drains |
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| publisher = University of California: Statewide Integrated Pest Management Project - Pesticide Education Program |
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| pages = 29 |
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| date = 1996 |
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| accessdate = 13 September 2015 |
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| url = http://www.cdpr.ca.gov/docs/license/pubs/sewrline.pdf}}</ref></blockquote> |
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The ] (FDA, a major operational division of the ]) mentions "dichlobenil" in a report entitled "Herbicidal suppression of bracken and effects on forage production."<ref> |
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{{cite web |
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| title = Herbicidal suppression of bracken and effects on forage production |
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| publisher = FDA Poisonous Plant Database |
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| date = 1971 |
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| accessdate = 13 September 2015 |
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| url = http://www.accessdata.fda.gov/scripts/plantox/detail.cfm?id=23085}}</ref> |
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The ] - ] has reported "high potential" for dichlobenil to enter groundwater.<ref name=bonneville>{{cite web |
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| title = Dichlobenil: Herbicide Fact Sheet |
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| publisher = U.S. Department of Energy - Bonneville Power Administration |
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| url = http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf |
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| pages = 2, 3 |
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| accessdate = 15 September 2015 |
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| archive-url = https://web.archive.org/web/20130225223833/http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf |
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| archive-date = 25 February 2013 |
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| url-status = dead |
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}}</ref> |
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===Residue=== |
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According to the US ],<ref>{{cite web |last1=EPA |title=Dichlobenil |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-027401_1-Oct-98.pdf |website=epa.gov |publisher=] |access-date=23 January 2023 |date=October 1998}}</ref> |
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{{quote|On an acute basis, dichlobenil is practically nontoxic to birds, mammals, honey bees; slightly to moderately toxic to aquatic invertebrates and estuarine organisms; and moderately toxic to fish. Dichlobenil is practically nontoxic to birds on a subacute dietary basis, but insufficient data are available to assess chronic avian toxicity. Dichlobenil is toxic to non-target terrestrial and aquatic plants. Dichlobenil may chronically affect fish at levels as low as 0.33 ppm and may chronically affect aquatic invertebrates at levels as low as 0.75 ppm. The dichlobenil degradate, BAM is slightly toxic to mammals and |
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practically nontoxic to fish and aquatic invertebrates on an acute basis.}} |
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Inland Fisheries Ireland has reported, "The dichlobenil residue in water almost completely dissipates in 5 to 6 months."<ref name=ireland>{{cite web |
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| title = Lagarosiphon Control in Lough Corrib |
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| publisher = Inland Fisheries Ireland |
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| url = http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf |
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| accessdate = 15 September 2015 |
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| archive-url = https://web.archive.org/web/20130225223833/http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf |
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| archive-date = 25 February 2013 |
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| url-status = dead |
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}}</ref> |
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U.S. FDA reports on pesticide residue. |
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<ref>{{cite web |
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| title = Pesticide Monitoring Program 2008 |
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| publisher = FDA |
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| date = 2008 |
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| accessdate = 13 September 2015 |
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| url = https://www.fda.gov/Food/FoodborneIllnessContaminants/Pesticides/ucm228867.htm}}</ref> |
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===Toxicity and environment=== |
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Since 1995, the ] has warned about potential damage to humans during indoor usage (see products listed, below): <blockquote>Leave all windows open and fans operating... Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. |
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<ref name=NIH> |
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{{cite web |
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| title = Dichlobenil |
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| publisher = NIH NLM ToxNet |
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| date = |
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| accessdate = 15 September 2015 |
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| url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+312}}</ref></blockquote> In 2006, the ] reported on "dichlobenil": <blockquote> It is no longer approved for use within the EU. It has low solubility, is not highly volatile and has potential to leach into groundwater. It is moderately persistent in soils and very persistent in water. It is moderately toxic to mammals, aquatic organisms, honeybees and earthworms.<ref name=PPDB> |
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{{cite web |
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| title = dichlobenil (Ref: H 133) |
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| publisher = University of Hertfordshire - Pesticide Properties DataBase |
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| date = 2006 |
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| accessdate = 13 September 2015 |
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| url = http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/214.htm}}</ref></blockquote> The report quotes a European Union regulatory effective date of 2009.<ref name=PPDB /> |
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The Inland Fisheries Ireland has reported: <blockquote> |
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The registration of all dichlobenil products (including Casoron G) was revoked in Ireland from 18th March 2009, under Commission Decision 2008/754/EC of 18th September 2008. A period of grace for the disposal, storage, placing on the market and use of existing stocks expired on 18th March 2010.<ref name=ireland /></blockquote> The London underground found itself in violation by using dichlobenil in September 2011.<ref> |
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{{cite news |
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| title = 'Toxic' pesticide Dichlobenil used on London Underground |
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| publisher = BBC News |
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| date = 2006 |
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| accessdate = 29 September 2011 |
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| url = https://www.bbc.com/news/uk-england-london-15107681}}</ref> |
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As of 2012, the United Nations' ] (IPCS) has advised that "the substance can be absorbed into the body by inhalation, through the skin and by ingestion... A harmful concentration of airborne particles can be reached quickly when dispersed... The substance may have effects on the skin. This may result in ]."<ref name=IPCS> |
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{{cite web |
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| title = dichlobenil (Ref: H 133) |
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| publisher = University of Hertfordshire - Pesticide Properties DataBase |
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| date = 2006 |
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| accessdate = 13 September 2015 |
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| url = http://www.inchem.org/documents/icsc/icsc/eics0867.htm}}</ref> Further, it has advised <blockquote>The substance is toxic to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.<ref name=IPCS /></blockquote> For personal protection during usage, the IPCS advises: <blockquote>Particulate filter respirator adapted to the airborne concentration of the substance... Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.<ref name=IPCS /></blockquote> While the ICPS warns strongly, "Do NOT let this chemical enter the environment," it does not note the contradiction that dichlobenil's usage is ''on'' the environment.<ref name=IPCS /> |
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The U.S. ] (CDC) follows and cites the ICPS.<ref name=CDC> |
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{{cite web |
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| title = Dichlobenil (Ref: H 133) |
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| publisher = CDC - International Chemical Safety Cards (ICSC) |
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| date = 2006 |
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| accessdate = 13 September 2015 |
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| url = https://www.cdc.gov/niosh/ipcsneng/neng0867.html}}</ref> |
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==Consumer products== |
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===United States=== |
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This partial list of consumer products with "dichlobenil" as an active ingredient: |
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* Oblitiroot<ref>{{cite web |
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| title = Oblitiroot |
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| publisher = Olvidium |
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| date = |
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| accessdate = 13 September 2015 |
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| url = http://www.olvidium.com/oblitiroot |
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| archive-date = 4 March 2016 |
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| archive-url = https://web.archive.org/web/20160304074252/http://www.olvidium.com/oblitiroot |
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| url-status = dead |
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}}</ref> |
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* Root Reach<ref> |
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{{cite web |
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| title = Root Reach |
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| publisher = Heartland Labs |
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| date = |
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| accessdate = 13 September 2015 |
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| url = http://www.heartlandlabs.com/rootreach.html}}</ref> |
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* Foaming Root Killer<ref> |
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{{cite web |
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| title = Foaming Root Killer |
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| publisher = Roebic |
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| date = |
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| accessdate = 13 September 2015 |
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| url = http://www.roebic.com/foaming-root-killer.shtml}}</ref> |
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* RootX<ref> |
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{{cite web |
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| title = RootX |
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| publisher = RootX |
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| date = |
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| accessdate = 13 September 2015 |
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| url = http://www.rootx.com/homeowners/faqs}}</ref> |
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==Synthesis == |
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Dichlobenil is produced from 2,6-] via the ].<ref name= Ullmanns/> |
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==References== |
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<references/> |
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{{Herbicides}} |
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{{DEFAULTSORT:Dichlorobenzonitrile, 2, 6-}} |
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] |
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] |
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] |