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Pirimicarb

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Pirimicarb
Names

Preferred IUPAC name 2-(Dimethylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate
Identifiers
CAS Number	23103-98-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8248^Y
ChemSpider	29348^Y
ECHA InfoCard	100.041.285
KEGG	C11079^Y
PubChem CID	31645
UNII	1I93PS935T^Y
CompTox Dashboard(EPA)	DTXSID1032569
InChI InChI=1S/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3^N Key: YFGYUFNIOHWBOB-UHFFFAOYSA-N^N InChI=1/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3 Key: YFGYUFNIOHWBOB-UHFFFAOYAL
SMILES CC1=C(N=C(N=C1OC(=O)N(C)C)N(C)C)C
Properties
Chemical formula	C₁₁H₁₈N₄O₂
Molar mass	238.29 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Pirimicarb is a selectivecarbamate insecticide used to controlaphids on vegetable, cereal and orchard crops by inhibitingacetylcholinesterase activity^[1] but does not affect useful predators such as ladybirds that eat them.^[2] It was originally developed byImperial Chemical Industries Ltd., nowSyngenta, at theirJealott's Hill site and first marketed in 1969, four years after its discovery.^[3]^[4]

References

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^McGregor, D. B. (2006),Pesticide Residues in Food - 2004,Food and Agriculture Organization,World Health Organization, p. 207,ISBN 92-4-166520-3, retrieved2008-05-08
^Clayden; Greeves; Warren (2001).Organic chemistry. Oxford university press. p. 178.ISBN 978-0-19-850346-0.
^"Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre"(PDF). Archived fromthe original(PDF) on October 11, 2007. RetrievedJune 26, 2012.
^Snell, B.K.; et al. (1978). "Chapter 11: Pyrimidine insecticides". In Peacock, F.C. (ed.).Jealott's Hill: Fifty years of Agricultural Research 1928-1978. Imperial Chemical Industries Ltd. pp. 98–109.ISBN 0901747017.

External links

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Pirimicarb in the Pesticide Properties DataBase (PPDB)

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

Acetylcholine metabolism andtransport 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 Tolserine; Others:Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huperzine B Huprine W Huprine X Huprine Y Huprine Z Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Velnacrine 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

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Nicotinic acetylcholine receptor modulators

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