Chlorphoxim

Chlorphoxim
Names
	IUPAC name (1Z)-2-chloro-N-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide
Identifiers
CAS Number	14816-20-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82108;
ChEMBL	ChEMBL1354530;
ChemSpider	7844758;
ECHA InfoCard	100.035.338
EC Number	238-888-9;
KEGG	C18969;
PubChem CID	9570291;
UNII	W1T1BS3R7V;
CompTox Dashboard (EPA)	DTXSID9057979 ;
	InChI 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;
	SMILES CCOP(=S)(OCC)O/N=C(\C#N)/C1=CC=CC=C1Cl;
Properties
Chemical formula	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). Infobox references

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

Properties

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

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

Chlorphoxim synthesis

Trade names

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

Approval

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

References

^ ^a ^b ^c Thomas A. Unger (1996), "Chlorphoxim", Pesticide Synthesis Handbook (in German), Elsevier, p. 312, doi:10.1016/b978-081551401-5.50240-9, ISBN 978-0-8155-1401-5
^ University of Hertfordshire. "Chlorphoxim (Ref: OMS 1197)". Retrieved 2022-06-22.
^ Bryan E. Miller, William. C. Bennett, Garth N. Graves, John R. Wheeler (1977-11-25), "Field Studies of Systemic Insecticides. II. Evaluation of chlorphoxim for control of fleas on five rodent species12", Journal of Medical Entomology (in German), vol. 14, no. 2, pp. 161–166, doi:10.1093/jmedent/14.2.161, ISSN 1938-2928, PMID 606815{{citation}}: CS1 maint: multiple names: authors list (link)
^ M. A. Khan (1983-02-01), "Wirksamkeit von Insektiziden und Repellents gegen Vorratsschädlinge", Anzeiger für Schädlingskunde, Pflanzenschutz, Umweltschutz (in German), vol. 56, no. 2, pp. 25–29, doi:10.1007/BF01905984, ISSN 1612-4766, S2CID 31751339
^ 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.

[:0-1] Thomas A. Unger (1996), "Chlorphoxim", Pesticide Synthesis Handbook (in German), Elsevier, p. 312, doi:10.1016/b978-081551401-5.50240-9, ISBN 978-0-8155-1401-5

[2] University of Hertfordshire. "Chlorphoxim (Ref: OMS 1197)". Retrieved 2022-06-22.

[3] Bryan E. Miller, William. C. Bennett, Garth N. Graves, John R. Wheeler (1977-11-25), "Field Studies of Systemic Insecticides. II. Evaluation of chlorphoxim for control of fleas on five rodent species12", Journal of Medical Entomology (in German), vol. 14, no. 2, pp. 161–166, doi:10.1093/jmedent/14.2.161, ISSN 1938-2928, PMID 606815{{citation}}: CS1 maint: multiple names: authors list (link)

[4] M. A. Khan (1983-02-01), "Wirksamkeit von Insektiziden und Repellents gegen Vorratsschädlinge", Anzeiger für Schädlingskunde, Pflanzenschutz, Umweltschutz (in German), vol. 56, no. 2, pp. 25–29, doi:10.1007/BF01905984, ISSN 1612-4766, S2CID 31751339

[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.

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