Phosphamidon: Difference between revisions

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	{{distinguish\|phosphoramidon}}		{{distinguish\|phosphoramidon}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~431611592~~
			\| Watchedfields = changed
⚫	\|ImageFile=Phosphamidon.~~png~~
		⚫	\| verifiedrevid = 444050677
⚫	\|ImageSize=~~200px~~
		⚫	\| ImageFile =(E,Z)-Phosphamidon Structural Formulae V.1.svg
⚫	\|IUPACName=(''E''/''Z'')- dimethyl phosphate
		⚫	\| ImageSize =360px
⚫	\|OtherNames=Dimecron
		⚫	\| IUPACName =(''E''/''Z'')- dimethyl phosphate
		⚫	\| OtherNames =Dimecron
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo=13171-21-6		\| CASNo = 13171-21-6
	\| CASOther = <br>297-99-4 (''E'')<br>23783-98-4 (''Z'')
			\| CASNo2_Ref = {{cascite\|correct\|CAS}}
	\| PubChem=25750
			\| CASNo2 = 297-99-4
			\| CASNo2_Comment = (''E'')
			\| CASNo3_Ref = {{cascite\|correct\|CAS}}
			\| CASNo3 = 23783-98-4
			\| CASNo3_Comment = (''Z'')
			\| PubChem =25750
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C18689		\| KEGG = C18689
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = 7H857A6N6H		\| UNII = 7H857A6N6H
⚫	\| SMILES=CCN(CC)C(=O)C(=C(C)OP(=O)(OC)OC)Cl
			\| UNII1_Ref = {{fdacite\|correct\|FDA}}
			\| UNII1 = 54VR7A0BQD
			\| UNII1_Comment = (''E'')
			\| UNII2_Ref = {{fdacite\|correct\|FDA}}
			\| UNII2 = HQ7958Q90Z
			\| UNII2_Comment = (''Z'')
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 23990
		⚫	\| SMILES = CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
			\| InChI = 1/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3
			\| InChIKey = RGCLLPNLLBQHPF-UHFFFAOYAA
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = RGCLLPNLLBQHPF-UHFFFAOYSA-N
	}}		}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| C=10\|H=19\|Cl=1\|N=1\|O=5\|P=1		\| C=10\|H=19\|Cl=1\|N=1\|O=5\|P=1
	\| Appearance=		\| Appearance =
	\| Density=1.2132 g/cm<sup>3</sup><ref name=inchem>, ]</ref>		\| Density =1.2132 g/cm<sup>3</sup><ref name=inchem>, ]</ref>
			\| MeltingPtC = 120 to 123
	\| MeltingPt=120-123 °C<ref name=Jacques>{{cite journal \| title = Toxicology and pharmacology of a new systemic phosphoric acid ester insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate) \| author = Jacques, R.; Bein, H. J. \| journal = Archiv fuer Toxikologie \| year = 1960 \| volume = 18 \| pages = 316–330}}</ref>
	\| ~~BoilingPt~~=~~162~~ ~~°C (1.5 mmHg)~~<ref name=~~Bachmann~~>{{cite journal \| title = ~~Phosphamidon,~~ a new ~~phosphate~~ ester ~~with~~ ~~systemic~~ ~~action~~ \| ~~author~~ = ~~Bachmann~~, ~~Fritz~~ \| ~~journal~~ = ~~Proc~~. ~~Intern~~. ~~Cong.~~ ~~Crop.~~ ~~Protection,~~ ~~4th~~ ~~Congr.,~~ ~~Hamburg~~ \|year = 1960 \| volume = 2 \| pages = ~~P1153-1155~~}}</ref>		\| MeltingPt_ref = <ref name=Jacques>{{cite journal \| title = Toxicology and pharmacology of a new systemic phosphoric acid ester insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate) \|author1=Jacques, R. \|author2=Bein, H. J. \| journal = Archiv für Toxikologie \| year = 1960 \| volume = 18 \| pages = 316–330\|doi=10.1007/BF02226232 \|s2cid=6714997 }}</ref>
			\| BoilingPtC = 162
	\| Solubility=Miscible
			\| BoilingPt_notes = (1.5 mmHg)<ref name=Bachmann>{{cite journal \| title = Phosphamidon, a new phosphate ester with systemic action \| author = Bachmann, Fritz \| journal = Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg \|year = 1960 \| volume = 2 \| pages = P1153-1155}}</ref>
			\| Solubility =Miscible
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards =
	\| FlashPt=		\| FlashPt =
			\| AutoignitionPt =
	\| Autoignition=
	\| LD50 = 13 mg/kg (mouse, oral)<ref name=Jacques/><br>6 mg/kg (mouse, IV)<ref name=Jacques/><br>20 mg/kg (rat, oral)<ref name=Jacques/><br>26 mg/kg (rat, subcut.)<ref name=Jacques/>		\| LD50 = 13 mg/kg (mouse, oral)<ref name=Jacques/><br />6 mg/kg (mouse, IV)<ref name=Jacques/><br />20 mg/kg (rat, oral)<ref name=Jacques/><br />26 mg/kg (rat, subcut.)<ref name=Jacques/>
	}}		}}
	}}		}}
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	== Toxicity and regulation==		== Toxicity and regulation==
	Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia.<ref name=inchem/> A harvester developed symptoms of moderately severe poisoning after working in a field that had been sprayed with the chemical 2 weeks earlier. He collapsed and exhibited significant depression of serum cholinesterase, but recovered completely within 2 days after successful treatment with atropine.<ref>S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. ~~Brit~~. J. Ind. Med. 22: 236-239, 1965.</ref> International trade of phosphamidon is covered by the ].		Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia.<ref name=inchem/> A harvester developed symptoms of moderately severe poisoning after working in a field that had been sprayed with the chemical 2 weeks earlier. He collapsed and exhibited significant depression of serum cholinesterase, but recovered completely within 2 days after successful treatment with atropine.<ref>S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Br. J. Ind. Med. 22: 236-239, 1965.</ref> International trade of phosphamidon is covered by the ].

	==References==		==References==
	{{reflist}}		{{reflist}}

			{{Insecticides}}
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			{{Acetylcholine metabolism and transport modulators}}

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Latest revision as of 00:45, 1 July 2022

Not to be confused with phosphoramidon.

Phosphamidon
Names

IUPAC name (E/Z)- dimethyl phosphate
Other names Dimecron
Identifiers
CAS Number	13171-21-6 297-99-4 (E) 23783-98-4 (Z)
3D model (JSmol)	Interactive image
ChemSpider	23990
ECHA InfoCard	100.032.818
KEGG	C18689
PubChem CID	25750
UNII	7H857A6N6H 54VR7A0BQD (E) HQ7958Q90Z (Z)
CompTox Dashboard (EPA)	DTXSID7021156
InChI InChI=1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3Key: RGCLLPNLLBQHPF-UHFFFAOYSA-N InChI=1/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3Key: RGCLLPNLLBQHPF-UHFFFAOYAA
SMILES CCN(CC)C(=O)/C(=C(\C)/OP(=O)(OC)OC)/Cl
Properties
Chemical formula	C₁₀H₁₉ClNO₅P
Molar mass	299.69 g·mol
Density	1.2132 g/cm
Melting point	120 to 123 °C (248 to 253 °F; 393 to 396 K)
Boiling point	162 °C (324 °F; 435 K) (1.5 mmHg)
Solubility in water	Miscible
Hazards
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	13 mg/kg (mouse, oral) 6 mg/kg (mouse, IV) 20 mg/kg (rat, oral) 26 mg/kg (rat, subcut.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Phosphamidon is an organophosphate insecticide first reported in 1960. It acts as a cholinesterase inhibitor.

The commercial product typically exists as a mixture of 70% (Z)-isomer and 30% (E)-isomer.

Toxicity and regulation

Phosphamidon is very highly toxic to mammals and is listed as WHO Hazard Class Ia. A harvester developed symptoms of moderately severe poisoning after working in a field that had been sprayed with the chemical 2 weeks earlier. He collapsed and exhibited significant depression of serum cholinesterase, but recovered completely within 2 days after successful treatment with atropine. International trade of phosphamidon is covered by the Rotterdam Convention.

References

^ Data Sheet on Pesticides No. 74: Phosphamidon, International Programme on Chemical Safety
^ Bachmann, Fritz (1960). "Phosphamidon, a new phosphate ester with systemic action". Proc. Intern. Cong. Crop. Protection, 4th Congr., Hamburg. 2: P1153-1155.
^ Jacques, R.; Bein, H. J. (1960). "Toxicology and pharmacology of a new systemic phosphoric acid ester insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate)". Archiv für Toxikologie. 18: 316–330. doi:10.1007/BF02226232. S2CID 6714997.
S. Gitelson, J. T. Davidson, A. Werczberger. Phosphamidon poisoning. Br. J. Ind. Med. 22: 236-239, 1965.

v t e Pest control: Insecticides
Carbamates	Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Isoprocarb Methomyl Metolcarb Oxamyl Promecarb Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas (Bistrifluron, Diflubenzuron, Flufenoxuron, Lufenuron, Noviflumuron) Hydroprene Methoprene Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Imidaclothiz Nitenpyram Nithiazine Paichongding Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Diamides	Chlorantraniliprole Cyantraniliprole Flubendiamide
Other chemicals	Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime) Pyridaben Pyriprole Sarolaner Adjuvants (Piperonyl butoxide, Sesamex) Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone Ryanodine Ryanodol
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum Spinosad