View source for Chlorobenzilate

{{chembox
|Reference = <ref name=niosh>[http://www.cdc.gov/niosh/ipcsneng/neng0749.html International Chemical Safety Card for chlorobenzilate], [[National Institute for Occupational Safety and Health]]</ref>
|ImageFile=Chlorobenzilate structure.png
|ImageSize=200px
|IUPACName=Ethyl 2,2-bis(4-chlorophenyl)-2-hydroxyacetate
|OtherNames=Chlorbenzylate; Chlorobenzylate
|Section1={{Chembox Identifiers
|  ChemSpiderID = 10085
| InChI = 1/C16H14Cl2O3/c1-2-21-15(19)16(20,11-3-7-13(17)8-4-11)12-5-9-14(18)10-6-12/h3-10,20H,2H2,1H3
| InChIKey = RAPBNVDSDCTNRC-UHFFFAOYAH
| CASNo= 510-15-6
|  PubChem=10522
|  SMILES = Clc1ccc(cc1)C(O)(c2ccc(Cl)cc2)C(=O)OCC
}}
|Section2={{Chembox Properties
|  C=16|H=14|Cl=2|O=3
|  Appearance=Colorless to pale yellow solid
|  Density=1.28 g/cm<sup>3</sup>
|  MeltingPtC=37
|  BoilingPt=
|  Solubility=
  }}
|Section3={{Chembox Hazards
|  MainHazards=
|  FlashPt=
|  Autoignition=
|  RPhrases = {{R22}} {{R50/53}}
|  SPhrases = {{S2}} {{S60}} {{S61}}
  }}
}}

'''Chlorobenzilate''' is a [[pesticide]] that is not currently used.  It was originally developed by [[Ciba-Geigy]] and introduced in 1952.<ref name=iarc>[http://www.inchem.org/documents/iarc/vol30/chlorobenzilate.html Chlorobenzilate], [[International Agency for Research on Cancer]]</ref> It was used as an [[acaricide]] against [[mite]]s on citrus trees, including deciduous fruit trees.<ref name=epa>[http://www.epa.gov/ttn/atw/hlthef/chlo-zil.html Chlorobenzilate], [[U.S. Environmental Protection Agency]]</ref> It is a non-systemic pesticide that works through contact and as a [[neurotoxin]]: it disrupts the functioning of the nervous system.

In the pure state, chlorobenzilate is a colorless to pale yellow solid, but the commercial product is a brownish liquid.<ref name=epa/> It is only slightly soluble in water, but [[miscible]] with [[acetone]], [[toluene]] and [[methanol]].

==Toxicity==
There is no data on the carcinogenic effects of chlorobenzilate in humans. However, when mice were administered the substance orally, carcinogenic effects were observed.<ref name=epa/> The U.S. Environmental Protection Agency has therefore classified chlorobenzilate as a probable human carcinogen (Group B2).<ref>U.S. Environmental Protection Agency.  Health Effects Assessment Summary Tables.  FY 1997 Update.  Solid Waste and Emergency Response, Office of Emergency and Remedial Response,  Cincinnati, OH.  EPA/540/R-97-036.  1997.</ref> The [[International Agency for Research on Cancer]] has concluded that there is insufficient information available to evaluate the carcinogenicity of chlorobenzilate in humans.<ref name=iarc/>

Chlorobenzilate is a [[persistent organic pollutant]] and is very toxic to aquatic invertebrates. 

==Regulation==
After carcinogenicity was established in mice, the use of chlorobenzilate was banned in the United States in 1979, except for citrus cultivation. After 1999, it was banned completely. In the European Union, its use is also currently banned.

International trade in chlorobenzilate is regulated by the [[Rotterdam Convention]].

==References==
{{Reflist}}

[[Category:Pesticides]]
[[Category:Organochlorides]]

[[nl:Chloorbenzilaat]]
[[ja:クロロベンジレート]]
[[Category:2Fix]]