2,6-Dichlorobenzonitrile

April 2017 changed 477212024 2,6-Dichlorobenzonitrile Structural Formula V1.svg 130 Skeletal formula 2,6-Dichlorobenzonitrile.png 170 Ball-and-stick model 2,6-Dichlorobenzonitrile Dichlobanil, Dichlobenil correct chemspider 2923 correct kegg C11040 1/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H YOYAIZYFCNQIRF-UHFFFAOYAG correct chemspider 1S/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H correct chemspider YOYAIZYFCNQIRF-UHFFFAOYSA-N correct CAS 1194-65-6 3031 correct EBI 943 correct FDA N42NR4196R N#Cc1c(Cl)cccc1Cl C7H3Cl2N 172.01 g/mol white crystalline powder 1.623 g/cm3 144.5 279 insoluble 126 2,6-Dichlorobenzonitrile (DCBN or dichlobenil) is an organic compound with the chemical formula C6H3Cl2CN. It is a white solid soluble in organic solvents. It is widely used as a herbicide and organic chemistry building block.Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 10.1002/14356007.o28_o01 Mechanism of action It has herbicidal properties killing young seedlings of both monocot and dicot species.Principles of weed science DCBN interferes with cellulose synthesis. DCBN adapted cell walls use minimal amounts of cellulose, instead relying on Ca2+-bridge pectates.Plant Responses to Environmental Stresses: From Phytohormones to Genome Reorganization: From Phytohormones to Genome Reorganization Dichlobenil kills the roots of many species, but not all; further, the killing does not extend much beyond the portion actually soaked, according to the Californian department of agriculture in 1971. Control of Tree Roots in Sewers and Drains California Agriculture 14 1971 13 September 2015 https://ucanr.edu/repositoryfiles/ca2511p13-63902.pdf Application In 1996, the University of California reported that "dosages were difficult to control... and as a result soaking or spraying methods are no longer used. ... The current application method involves applying metam-sodium products in foam carriers (similar to shaving cream)." Control of Tree Roots in Sewers and Drains University of California: Statewide Integrated Pest Management Project - Pesticide Education Program 29 1996 13 September 2015 http://www.cdpr.ca.gov/docs/license/pubs/sewrline.pdf Environmental behavior 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. dichlobenil (Ref: H 133) University of Hertfordshire - Pesticide Properties DataBase 2006 13 September 2015 http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/214.htm Dichlobenil residue in water almost completely dissipates in 5 to 6 months. Lagarosiphon Control in Lough Corrib Inland Fisheries Ireland http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf 15 September 2015 https://web.archive.org/web/20130225223833/http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf 25 February 2013 dead The USDOE Bonneville Power Administration reported "high potential" for dichlobenil to enter groundwater. Dichlobenil: Herbicide Fact Sheet U.S. Department of Energy - Bonneville Power Administration http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf 2, 3 15 September 2015 https://web.archive.org/web/20130225223833/http://efw.bpa.gov/environmental_services/Document_Library/Vegetation_Management/sheets/Dichlobenil.pdf 25 February 2013 dead Regulatory status It is no longer approved for use within the EU, as of 2009. The Inland Fisheries Ireland has reported "the registration of all dichlobenil products ... was revoked in Ireland from 18th March 2009, under Commission Decision 2008/754/EC of 18th September 2008. A period of grace for ... existing stocks expired on 18th March 2010." The London underground found itself in violation by using dichlobenil in September 2011. 'Toxic' pesticide Dichlobenil used on London Underground BBC News 2006 29 September 2011 https://www.bbc.com/news/uk-england-london-15107681 Environmental toxicity 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 practically nontoxic to fish and aquatic invertebrates on an acute basis.EPA Dichlobenil https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-027401_1-Oct-98.pdf epa.gov US EPA 23 January 2023 October 1998 Safety Since 1995, the U.S. National Institutes of Health has warned about indoor usage: "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." Dichlobenil NIH NLM ToxNet 15 September 2015 https://www.nlm.nih.gov/toxnet/index.html The UN IPCS reports dichlobenil can be absorbed into the body by inhalation, through skin and by ingestion, and that dispersion can create harmful concentrations in air quickly; dichlobenil may affect skin, possbily causing chloracne. dichlobenil (Ref: H 133) University of Hertfordshire - Pesticide Properties DataBase 2006 13 September 2015 http://www.inchem.org/documents/icsc/icsc/eics0867.htm Further, it warns dichlobenil is toxic to aquatic organisms, and does enter the environment under normal use, but great care should be taken to avoid release, e.g. through inappropriate disposal. The IPCS advises particulate filter respirators as PPE adapted to the air concentration of dichlobenil; spilled substance should be swept into covered sealable containers, moistened if needed to prevent dusting, and disposed of according to local regulations. The U.S. Centers for Disease Control and Prevention (CDC) follows and cites the ICPS. Dichlobenil (Ref: H 133) CDC - International Chemical Safety Cards (ICSC) 2006 13 September 2015 https://www.cdc.gov/niosh/ipcsneng/neng0867.html Products United States These consumer products use dichlobenil as an active ingredient: "Oblitiroot", Oblitiroot Olvidium 13 September 2015 http://www.olvidium.com/oblitiroot 4 March 2016 https://web.archive.org/web/20160304074252/http://www.olvidium.com/oblitiroot dead "Root Reach", Root Reach Heartland Labs 13 September 2015 http://www.heartlandlabs.com/rootreach.html "Foaming Root Killer" Foaming Root Killer Roebic 13 September 2015 http://www.roebic.com/foaming-root-killer.shtml and "RootX". RootX RootX 13 September 2015 http://www.rootx.com/homeowners/faqs This is not an exhaustive list. "Casoron" is dichlobenil sold agriculturally as a 50% wettable powder and as 4% granules.Williams H.h. Effects of certain preemergence herbicides on Diochondra spp. Proceedings of the Second International Turfgrass Research Conference 1974 410–417 10.2135/1974.proc2ndintlturfgrass.c60 Synthesis Dichlobenil is produced from 2,6-dichlorotoluene via the aldoxime. A known use of dichlobenil is in the synthesis of hycanthone.((Laidlaw, G. M.)), ((Collins, J. C.)), ((Archer, S.)), ((Rosi, D.)), ((Schulenberg, J. W.)) The Journal of Organic Chemistry Synthesis of hycanthone 38 9 1743–1746 May 1973 https://pubs.acs.org/doi/abs/10.1021/jo00949a030 10.1021/jo00949a030 28 August 2026 subscription References Category:Herbicides Category:Benzonitriles Category:Dichlorophenyl compounds Category:Group 29 herbicides