Resmethrin: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
			\| Watchedfields = changed
			\| verifiedrevid = 464381193
	\| Name = Resmethrin		\| Name = Resmethrin
	\| ImageFile = Resmethrin-2D-skeletal.png		\| ImageFile = Resmethrin-2D-skeletal.png
	<!-- \| ImageSize = 200px -->		<!-- \| ImageSize = 200px -->
	\| ImageName =		\| ImageName =
	\| IUPACName = 5-benzyl-3-[({[(3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)		\| IUPACName = (5-benzylfuran-3-yl)methyl (2''R'')-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate; <br /> 5-benzyl-3-[({[(3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)
			cyclopropyl]carbonyl}oxy)methyl]furan; <br /> (5-Benzyl-3-furyl)methyl-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropancarboxylate; <br /> 5-benzyl-3-furylmethyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; <br /> 5-benzyl-3-furylmethyl(1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; <br /> 5-benzyl-3-furylmethyl(±)-cis-trans-chrysanthemate
	cyclopropyl]carbonyl}oxy)methyl]furan
			\| OtherNames = methyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| CASNo = xx-xx-xx
			\| ChemSpiderID = 19952179
			\| 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/s1
			\| InChIKey = VEMKTZHHVJILDY-FIWHBWSRBD
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChI = 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/s1
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 2106605
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CASNo = 10453-86-8
			\| CASNo1_Ref = {{cascite\|correct\|??}}
			\| CASNo1 = 28434-01-7
			\| CASNo1_Comment = (Bioresmethrin)
			\| ChEBI = 8811
			\| RTECS = GZ1310000
			\| UNNumber = 3082 3349 2902
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = Z6PN6KTG4K
			\| UNII1_Ref = {{fdacite\|correct\|FDA}}
			\| UNII1 = YPP8YQZ13B
			\| UNII1_Comment = (Bioresmethrin)

			\| PubChem = 5053
			\| EINECS = 233-940-7
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = C10991
	\| SMILES = O=C(OCc2cc(Cc1ccccc1)oc2)C3(/C=C(\C)C)C3(C)C		\| SMILES = O=C(OCc2cc(Cc1ccccc1)oc2)C3(/C=C(\C)C)C3(C)C
	}}		}}
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	\| BoilingPt =		\| BoilingPt =
	}}		}}
			\|Section7={{Chembox Hazards
			\| GHSPictograms = {{GHS07}}{{GHS09}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|302\|410}}
			\| PPhrases = {{P-phrases\|264\|270\|273\|301+312\|330\|391\|501}}
			}}
	}}		}}

	'''Resmethrin''' is a ] ] with many uses, including control of the adult ] population. A 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.<ref>Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). </ref>		'''Resmethrin''' is a ] ] with many uses, including control of the adult ] 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)-, and (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, Lethalaire V-26, Pynosect, Raid Flying Insect Killer, Scourge, SPB-1382, Sun-Bugger #4, Synthrin, Syntox, Vectrin, and Whitmire PT-110.<ref>Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). </ref>

	==References==		==References==
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	==External links==		==External links==
			*{{PPDB\|585}}
	*		*
	*		*
	*		*
	* for Scourge~~''''~~ Formula II		* for Scourge Formula II
			* {{Webarchive\|url=https://web.archive.org/web/20110609010311/http://www.inchem.org/documents/pds/pds/pest83_e.htm \|date=2011-06-09 }}
			*

			{{insecticides}}
⚫	]
⚫	]
⚫	]

		⚫	]

		⚫	]
	{{organic-compound-stub}}
			]
		⚫	]

Latest revision as of 00:00, 3 July 2024

Resmethrin
Names

IUPAC names (5-benzylfuran-3-yl)methyl (2R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate; 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)cyclopropancarboxylate; 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
ChEBI	CHEBI:8811
ChEMBL	ChEMBL2106605
ChemSpider	19952179
ECHA InfoCard	100.030.842
EC Number	233-940-7
KEGG	C10991
PubChem CID	5053
RTECS number	GZ1310000
UNII	Z6PN6KTG4K YPP8YQZ13B (Bioresmethrin)
UN number	3082 3349 2902
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
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H410
Precautionary statements	P264, P270, P273, P301+P312, P330, P391, P501
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)-, and (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, Lethalaire V-26, Pynosect, Raid Flying Insect Killer, Scourge, SPB-1382, Sun-Bugger #4, 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
WHO/FAO DATA SHEETS ON PESTICIDES, No. 83, RESMETHRIN World Health Organization & Food and Agriculture Organization Archived 2011-06-09 at the Wayback Machine
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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