Cyanophos

Cyanophos
Names

Preferred IUPAC name O-(4-Cyanophenyl) O,O-dimethyl phosphorothioate
Identifiers
CAS Number	2636-26-2^Y
3D model (JSmol)	Interactive image
Beilstein Reference	2695901
ChEBI	CHEBI:38621
ChEMBL	ChEMBL2271089
ChemSpider	16569
ECHA InfoCard	100.018.301
EC Number	220-130-3
KEGG	C18397
PubChem CID	17522
UNII	2AB0Z99OXP
UN number	3018
CompTox Dashboard (EPA)	DTXSID0041806
InChI InChI=1S/C9H10NO3PS/c1-11-14(15,12-2)13-9-5-3-8(7-10)4-6-9/h3-6H,1-2H3 Key: SCKHCCSZFPSHGR-UHFFFAOYSA-N InChI=1/C9H10NO3PS/c1-11-14(15,12-2)13-9-5-3-8(7-10)4-6-9/h3-6H,1-2H3 Key: SCKHCCSZFPSHGR-UHFFFAOYAF
SMILES COP(=S)(OC)OC1=CC=C(C=C1)C#N
Properties
Chemical formula	C₉H₁₀NO₃PS
Molar mass	243.22 g·mol⁻¹
Appearance	Yellow to reddish-yellow transparent liquid
Density	0.932 g/cm³
Melting point	14 to 15 °C; 57 to 59 °F; 287 to 288 K
Boiling point	119 to 120 °C; 246 to 248 °F; 392 to 393 K at 0.09 mmHg
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H361, H370, H372, H400
Precautionary statements	P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P302+P352, P307+P311, P308+P313, P312, P314, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)	2 1 1
Safety data sheet (SDS)	^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Cyanophos is a cholinesterase inhibitor^[2] used as an insecticide and avicide; for example, against rice stem borers and house flies. It is part of the chemical class of organophosphorus compounds, and is a yellow to reddish-yellow transparent liquid.

Safety

Cyanophos can enter the body via inhalation, ingestion, and contact with the skin and eyes. Symptoms of cyanophos poisoning resemble those of the chemical weapon sarin and include dyspnea, vomiting, diarrhea, abdominal pain, bronchorrhea, blurred vision, and opsoclonus.^[1]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[3]

Synonyms

BAY 34727
Bayer 34727
Ciafos
Cyanofos
Cyanox
Cyap
ENT 25,675
O,O-dimethyl O-(4-cyanophenyl) phosphorothioate
O,O-dimethyl O-(p-cyanophenyl) phosphorothioate
O,O-dimethyl O-4-cyanophenyl phosphorothioate
O,O-dimethyl O-4-cyanophenyl thiophosphate
O,O-dimethyl-O-p-cyanophenyl phosphorothioate
O-p-cyanophenyl O,O-dimethyl phosphorothioate
Phosphorothioic acid O-(4-cyanophenyl) O,O-dimethyl ester
Phosphorothioic acid, O,O-dimethyl ester, O-ester with p-hydroxybenzonitrile
Phosphorothioic acid, O-p-cyanophenyl O,O-dimethyl ester
S 4084
Sumitomo S 4084

References

^ ^a ^b "Material Safety Data Sheets: Cyanophos" (PDF). Central Pollution Control Board, Ministry of Environment & Forests, Government of India. Archived from the original (PDF) on 2012-04-22. Retrieved 2011-12-08.
^ "Cyanophos: CAMEO Chemicals". NOAA.gov. Retrieved 2011-12-08.
^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)

Pest control: Insecticides

Carbamates

Inorganic compounds

Insect growth regulators

Other chemicals

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChETooltip Butyrylcholinesterase	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChTTooltip Vesicular acetylcholine transporter	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E) VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHNTooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin