Diazinon

Diazinon
Names
	Preferred IUPAC name O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate
	Other names Diethoxy-[(2-isopropyl-6-methyl-4-pyrimidinyl)oxy]-thioxophosphorane; Basudin; Diazide; Spectracide
Identifiers
CAS Number	333-41-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34682 ;
ChEMBL	ChEMBL388560 ;
ChemSpider	2909 ;
ECHA InfoCard	100.005.795
KEGG	D07856 ;
PubChem CID	3017;
UNII	YUS1M1Q929 ;
CompTox Dashboard (EPA)	DTXSID9020407 ;
	InChI InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3 Key: FHIVAFMUCKRCQO-UHFFFAOYSA-N ;
	SMILES S=P(OCC)(OCC)Oc1nc(nc(c1)C)C(C)C;
Properties
Chemical formula	C12H21N2O3PS
Molar mass	304.34 g·mol−1
Appearance	Colorless to dark brown liquid
Odor	faint, ester-like
Density	1.116-1.118 g/cm3 at 20 °C
Boiling point	decomposes
Solubility in water	40 mg/L
log P	3.81 (octanol/water)
Pharmacology
ATCvet code	QP53AF03 (WHO)
Hazards
Flash point	82 °C; 180 °F; 355 K
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 0.1 mg/m3 [skin]
IDLH (Immediate danger)	N.D.
	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

Diazinon (IUPAC name: O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate, INN - Dimpylate), a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks^[5] but it is still approved for agricultural uses. An emergency antidote is atropine.^[6]

Specific Health Risks: Routes of contact for Diazinon include breathing it, consuming it, or contact with skin. The negative health effects when in contact with Diazinon includes eye watering, drool or runny nose, not having any appetite, throwing up, intense coughing, abdominal pain, or even stiffness in various muscles/paralysis.^[7] Headaches can also be health risks.^[8] Some other physiological effects include pinpoint pupils, increased heart rate, seizures, or even coma. Larger exposure to diazinon is known to yield these risks. If it is a smaller exposure, the symptoms may be reduced such as just a runny nose or some eye watering.^[9] One thing to note is that while Diazinon has many different health risks, the EPA has not categorized it as a carcinogen.^[10]

^ Budavari, S., ed. (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck. p. 508.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0181". National Institute for Occupational Safety and Health (NIOSH).
^ Sharom, M.S.; Miles, J.R.W.; Harris, C.R.; McEwen, F.L. (1980). "Behaviour of 12 insecticides in soil and aqueous suspensions of soil and sediment". Water Research. 14 (8): 1095–100. Bibcode:1980WatRe..14.1095S. doi:10.1016/0043-1354(80)90158-X.
^ Hansch, Corwin; Leo, Albert; Hoekman, David (1995). Exploring QSAR: Volume 2: Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 106. ISBN 978-0-8412-2991-4.
^ Cone, Marla (1 Jan 2005). "EPA Takes Pest Killer Diazinon Off the Shelves". Los Angeles Times. Retrieved 2 Jul 2020.
^ Geller, Robert J.; Lopez, Gaylord P.; Cutler, Stephen; Lin, Diana; Bachman, George F.; Gorman, Susan E. (2003). "Atropine availability as an antidote for nerve agent casualties: Validated rapid reformulation of high-concentration atropine from bulk powder". Annals of Emergency Medicine. 41 (4): 453–6. doi:10.1067/mem.2003.103. PMID 12658242.
^ "Diazinon General Fact Sheet". npic.orst.edu. Retrieved 2024-03-14.
^ Dahlgren, J. G.; Takhar, H. S.; Ruffalo, C. A.; Zwass, M. (2004). "Health effects of diazinon on a family". Journal of Toxicology. Clinical Toxicology. 42 (5): 579–591. doi:10.1081/clt-200026979. ISSN 0731-3810. PMID 15462149.
^ "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.
^ "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.

[1] Budavari, S., ed. (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck. p. 508.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards. "#0181". National Institute for Occupational Safety and Health (NIOSH).

[3] Sharom, M.S.; Miles, J.R.W.; Harris, C.R.; McEwen, F.L. (1980). "Behaviour of 12 insecticides in soil and aqueous suspensions of soil and sediment". Water Research. 14 (8): 1095–100. Bibcode:1980WatRe..14.1095S. doi:10.1016/0043-1354(80)90158-X.

[4] Hansch, Corwin; Leo, Albert; Hoekman, David (1995). Exploring QSAR: Volume 2: Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 106. ISBN 978-0-8412-2991-4.

[:0-5] Cone, Marla (1 Jan 2005). "EPA Takes Pest Killer Diazinon Off the Shelves". Los Angeles Times. Retrieved 2 Jul 2020.

[6] Geller, Robert J.; Lopez, Gaylord P.; Cutler, Stephen; Lin, Diana; Bachman, George F.; Gorman, Susan E. (2003). "Atropine availability as an antidote for nerve agent casualties: Validated rapid reformulation of high-concentration atropine from bulk powder". Annals of Emergency Medicine. 41 (4): 453–6. doi:10.1067/mem.2003.103. PMID 12658242.

[7] "Diazinon General Fact Sheet". npic.orst.edu. Retrieved 2024-03-14.

[8] Dahlgren, J. G.; Takhar, H. S.; Ruffalo, C. A.; Zwass, M. (2004). "Health effects of diazinon on a family". Journal of Toxicology. Clinical Toxicology. 42 (5): 579–591. doi:10.1081/clt-200026979. ISSN 0731-3810. PMID 15462149.

[9] "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.

[10] "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.

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