3301. Dioxathion

Nomenclature

CAS number: 78-34-2
Phosphorodithioic acid S,S′-1,4-dioxane-2,3-diyl O,O,O′,O′-tetraethyl ester; 2,3-p-dioxanedithiol S,S-bis(O,O-diethyl phosphorodithioate); AC-528; ENT-22879; Hercules 528; Delnav; Navadel.
C12H26O6P2S4; mol wt 456.54.
C 31.57%, H 5.74%, O 21.03%, P 13.57%, S 28.09%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: Diveley, Lohr, US 2725328; Speck, US 2815350 (1955, 1957 both to Hercules); Diveley et al., J. Am. Chem. Soc. 81, 139 (1959) DOI. Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed.

Chemical structure

Properties

Tan liquid, d426 1.257. mp -20°. nD20 1.5420. Practically insol in water. Partly sol in hexane. Hydrolyzed by alkali and by heating. Poisonous. LD50 in female, male rats (mg/kg): 23, 43 orally; 63, 235 dermally (Gaines).

Caution

Potential symptoms of overexposure are eye, skin irritation; headache, giddiness, vertigo, weakness; rhinorrhea, chest tightness; miosis; nausea, vomiting, abdominal cramps, diarrhea, salivation; muscle fasciculations; confusion, drowsiness. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 120.

Use

Insecticide; acaricide.