Isomalathion

Isomalathion
Names
	Preferred IUPAC name Diethyl {[methoxy(methylsulfanyl)phosphoryl]sulfanyl}butanedioate
	Other names S-Methylmalathion
Identifiers
CAS Number	3344-12-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	82649 ;
PubChem CID	91529;
UNII	9XEP5P83AO ;
CompTox Dashboard (EPA)	DTXSID9058363 ;
	InChI InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(13,14-3)18-4/h8H,5-7H2,1-4H3 Key: LPQDGVLVYVULMX-UHFFFAOYSA-N ; InChI=1/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(13,14-3)18-4/h8H,5-7H2,1-4H3 Key: LPQDGVLVYVULMX-UHFFFAOYAO;
	SMILES CCOC(=O)CC(C(=O)OCC)SP(=O)(OC)SC;
Properties
Chemical formula	C10H19O6PS2
Molar mass	330.36 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Isomalathion is an impurity found in some batches of malathion. Whereas the structure of malation is, generically, RSP(S)(OCH₃)₂, the connectivity of isomalathion is RSPO(SCH₃)(OCH₃). It arises by heating malathion. Being significantly more toxic to humans than malathion, it has resulted in human poisonings.^[1]

In 1976, numerous malaria workers in Pakistan were poisoned by isomalathion.^[2] It is an inhibitor of carboxyesterase.

References

^ Rengasamy, S.; Parmer, Balraj S. (1988). "Investigation of some factors influencing isomalathion formation in malathion products". Journal of Agricultural and Food Chemistry. 36 (5): 1025–1030. doi:10.1021/jf00083a030.
^ Baker EL, Warren M, Zack M, et al. (1978). "Epidemic malathion poisoning in Pakistan malaria workers". Lancet. 1 (8054): 31–4. doi:10.1016/S0140-6736(78)90375-6. PMID 74508. S2CID 24973326.

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[1] Rengasamy, S.; Parmer, Balraj S. (1988). "Investigation of some factors influencing isomalathion formation in malathion products". Journal of Agricultural and Food Chemistry. 36 (5): 1025–1030. doi:10.1021/jf00083a030.

[pmid74508-2] Baker EL, Warren M, Zack M, et al. (1978). "Epidemic malathion poisoning in Pakistan malaria workers". Lancet. 1 (8054): 31–4. doi:10.1016/S0140-6736(78)90375-6. PMID 74508. S2CID 24973326.

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