Chlorphoxim

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Chlorphoxim
File:Chlorphoxim Structural Formula.svg
Names
IUPAC name
(1Z)-2-chloro-N-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 238-888-9
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=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+
  • Key: GQKRUMZWUHSLJF-NTCAYCPXSA-N
  • CCOP(=S)(OCC)O/N=C(\C#N)/C1=CC=CC=C1Cl
Properties
C12H14ClN2O3PS
Molar mass 332.74 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorphoxime is an insecticide used as crop protection active ingredient.[1] Chlorphoxime is also a cholinesterase inhibitor and a neurotoxin.[2]

Properties

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A study was conducted to investigate the effect of chlorophoxime for the control of fleas in kangaroo rats and hispid cotton rats. Chlorphoxime was found to be effective.[3]

In another study, the efficacy of some insecticides was investigated on certain 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.[4]

Production

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The synthesis of chlorophoxime is described in the following reaction sequence:[1]

Chlorphoxim synthesis
Chlorphoxim synthesis

Trade names

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A crop protection product containing the active ingredient chlorophoxime is marketed under the trade name Baythion.[1]

Approval

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No plant protection products containing chlorophoxime are approved in the European Union or Switzerland.[5]

References

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  5. ^ European Commission Directorate-General for Health and Food Safety: EU Pesticides Database; entry in the national plant protection product inventories of Switzerland, Austria and Germany, accessed July 20, 2022.