View source for Chlorphoxim

{{Chembox
<!-- Images -->
| ImageFile      = Chlorphoxim Structural Formula.svg
| ImageSize      = 300px
| ImageAlt       =
<!-- Names -->
| IUPACName      = (1Z)-2-chloro-N-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide
| OtherNames     =
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| Section1       = {{Chembox Identifiers
| CASNo          = 14816-20-7
| ChEBI = 82108
| ChEMBL = 1354530
| ChemSpiderID = 7844758
| EINECS =  238-888-9
| KEGG = C18969
| PubChem        = 9570291
| UNII = W1T1BS3R7V
| StdInChI=1S/C12H14ClN2O3PS/c1-3-16-19(20,17-4-2)18-15-12(9-14)10-7-5-6-8-11(10)13/h5-8H,3-4H2,1-2H3/b15-12+
| InChIKey = GQKRUMZWUHSLJF-NTCAYCPXSA-N
| SMILES = CCOP(=S)(OCC)O/N=C(\C#N)/C1=CC=CC=C1Cl
}}
| Section2       = {{Chembox Properties
| Formula        = C<sub>12</sub>H<sub>14</sub>ClN<sub>2</sub>O<sub>3</sub>PS
| MolarMass      = 332.74 g·[[Molar mass|mol]]<sup>−1</sup>
| Appearance     =
| Density        =
| MeltingPt      =
| BoilingPt      =
| Solubility     =
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| Section3       = {{Chembox Hazards
| MainHazards    =
| FlashPt        =
| AutoignitionPt =
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}}
'''Chlorphoxime''' is an [[insecticide]] used as [[Crop protection product|crop protection active ingredient]].<ref name=":0">{{citation|surname1=Thomas A. Unger|periodical=Pesticide Synthesis Handbook|title=Chlorphoxim|publisher=Elsevier|at=p.&nbsp;312|isbn=978-0-8155-1401-5|date=1996|language=German|doi=10.1016/b978-081551401-5.50240-9
}}</ref> Chlorphoxime is also a [[cholinesterase inhibitor]] and a [[neurotoxin]].<ref>{{cite web|title=Chlorphoxim (Ref: OMS 1197)|periodical=|publisher=|url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1290.htm|url-status=|format=|access-date=2022-06-22|archive-url=|archive-date=|last=University of Hertfordshire|date=|year=|language=|pages=|quote=}}</ref>
== Properties ==
A study was conducted to investigate the effect of chlorophoxime for the control of fleas in [[Kangaroo rat|kangaroo rats]] and [[Hispid cotton rat|hispid cotton rats]]. Chlorphoxime was found to be effective.<ref>{{citation|surname1=Bryan E. Miller, William. C. Bennett, Garth N. Graves, John R. Wheeler|periodical=Journal of Medical Entomology|title=Field Studies of Systemic Insecticides. II. Evaluation of chlorphoxim for control of fleas on five rodent species12|volume=14|issue=2|at=pp.&nbsp;161–166|issn=1938-2928|date=1977-11-25|language=German|doi=10.1093/jmedent/14.2.161
|pmid=606815 }}</ref>
In another study, the efficacy of some insecticides was investigated on certain [[Storage pest|storage pests]]. While [[phoxim]], [[bioresmethrin]] and [[fenitrothion]] showed strong activity against the red-brown rice [[mealybug]], the insecticidal activity of ''chlorphoxim'' and [[permethrin]] was low.<ref>{{citation|surname1=M. A. Khan|periodical=Anzeiger für Schädlingskunde, Pflanzenschutz, Umweltschutz|title=Wirksamkeit von Insektiziden und Repellents gegen Vorratsschädlinge|volume=56|issue=2|at=pp.&nbsp;25–29|issn=1612-4766|date=1983-02-01|language=German|doi=10.1007/BF01905984
|s2cid=31751339 }}</ref>
== Production ==
The synthesis of chlorophoxime is described in the following reaction sequence:<ref name=":0" />
[[File:Chlorphoxim Synthesis.svg|center|frameless|upright=2|Chlorphoxim synthesis]]
== Trade names ==
A crop protection product containing the active ingredient chlorophoxime is marketed under the trade name ''Baythion''.<ref name=":0" />
== Approval ==
No plant protection products containing chlorophoxime are approved in the European Union or Switzerland.<ref> European Commission Directorate-General for Health and Food Safety: [https://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/active-substances/?event=search.as EU Pesticides Database]; entry in the national plant protection product inventories of Switzerland, Austria and Germany, accessed July 20, 2022.</ref>
== References==
<references />
[[Category:2-Chlorophenyl compounds]]
[[Category:Oxime esters]]
[[Category:Nitriles]]
[[Category:Thiophosphoryl compounds]]
[[Category:Ethyl esters]]