Resmethrin: Difference between revisions

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Revision as of 23:16, 5 August 2016 editFswitzer4 (talk \| contribs)Extended confirmed users10,611 editsm Added UNII from FDA SRS← Previous edit		Revision as of 18:59, 5 March 2017 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - updated 'CASNo1_Ref', 'ChEMBL_Ref', 'UNII_Ref', 'Verifiedfields') per Chem/infobox_drug validation (report errors or [[user talk:Ch...Next edit →
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N		\| StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChEMBL = 2106605		\| ChEMBL = 2106605
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	\| CASNo = 10453-86-8		\| CASNo = 10453-86-8
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	\| CASNo1 = 28434-01-7		\| CASNo1 = 28434-01-7
	\| CASNo1_Comment = (Bioresmethrin)		\| CASNo1_Comment = (Bioresmethrin)

	\| UNII_Ref = {{fdacite\|~~correct~~\|FDA}}		\| UNII_Ref = {{fdacite\|changed\|FDA}}

	\| UNII = Z6PN6KTG4K		\| UNII = Z6PN6KTG4K

Revision as of 18:59, 5 March 2017

Resmethrin
Names

IUPAC name 5-benzyl-3-[({[(3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl) cyclopropyl]carbonyl}oxy)methyl]furan; (5-Benzyl-3-furyl)methyl-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropancarboxylat; 5-benzyl-3-furylmethyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 5-benzyl-3-furylmethyl(1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 5-benzyl-3-furylmethyl(±)-cis-trans-chrysanthemate
Other names methyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate
Identifiers
CAS Number	10453-86-8 28434-01-7 (Bioresmethrin)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2106605
ChemSpider	19952179
ECHA InfoCard	100.030.842
KEGG	C10991
UNII	Z6PN6KTG4K
CompTox Dashboard (EPA)	DTXSID7022253
InChI InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20?/m1/s1Key: VEMKTZHHVJILDY-FIWHBWSRSA-N InChI=1/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20?/m1/s1Key: VEMKTZHHVJILDY-FIWHBWSRBD
SMILES O=C(OCc2cc(Cc1ccccc1)oc2)C3(/C=C(\C)C)C3(C)C
Properties
Chemical formula	C₂₂H₂₆O₃
Molar mass	338.44 g/mol
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

Resmethrin is a pyrethroid insecticide with many uses, including control of the adult mosquito population.

The resmethrin molecule has four stereoisomers determined by cis-trans orientation around a carbon triangle and chirality. Technical resmethrin is a mixture of (1R,trans)-, (1R,cis)-, (1S,trans)-, (1S,cis)- isomers, typically in a ratio of 4:1:4:1. The 1R isomers (both trans and cis) show strong insecticidal activity, while the 1S isomers do not. The (1R,trans)- isomer is also known as Bioresmethrin,(+)-trans-Resmethrin, or d-trans-Resmethrin; although bioresmethrin has been used alone as a pesticide active ingredient, it is not now registered as a separate Active Ingredient (AI) by the U.S. EPA. The (1R,cis)- isomer is known as Cismethrin, but this is also not registered in the U.S. for use alone as a pesticide AI.

Commercial trade names for products that contain resmethrin are Chrysron, Crossfire, Pynosect, Raid Flying Insect Killer, Scourge, Sun-Bugger #4, SPB-1382, Synthrin, Syntox, Vectrin and Whitmire PT-110.

References

Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). Resmethrin

External links

Resmethrin in the Pesticide Properties DataBase (PPDB)
Resmethrin Technical Fact Sheet - National Pesticide Information Center
Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
Resmethrin Pesticide Information Profile - Extension Toxicology Network
MSDS for Scourge' Formula II
Compendium of Pesticide Common Names: Resmethrin
WHO/FAO DATA SHEETS ON PESTICIDES,No. 83,RESMETHRIN World Health Organization & Food and Agriculture Organization
Reregistration Eligibility Decision for Resmethrin (2006) - U.S. Environmental Protection Agency

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

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