Carbaryl

Carbaryl  |  |

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Names
Preferred IUPAC name

Naphthalen-1-yl methylcarbamate

Other names

Sevin (Generic trademark)
α-Naphthyl N-methylcarbamate
1-Naphthyl methylcarbamate

Identifiers

CAS Number

* 63-25-2 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:3390 Y

ChEMBL |

* ChEMBL46917 Y

ChemSpider |

* 5899 Y

EC Number |

* 200-555-0

KEGG |

* D07613 Y

PubChem CID

* 6129

RTECS number |

* FC5950000

UNII |

* R890C8J3N1 Y

UN number | 2757

InChI

* InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14) Y

Key: CVXBEEMKQHEXEN-UHFFFAOYSA-N Y

* InChI=1/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)

Key: CVXBEEMKQHEXEN-UHFFFAOYAZ

SMILES

* CNC(=O)Oc1c2ccccc2ccc1

Properties

Chemical formula

| C12H11NO2
Molar mass | 201.225 g·mol−1
Appearance  | Colorless crystalline solid
Density | 1.2 g/cm3
Melting point |  142 °C (288 °F; 415 K)
Boiling point | decomposes

Solubility in water

| very low (0.01% at 20°C)[1]
Pharmacology
1=ATCvet code}  | QP53AE01 (WHO)
Hazards
Safety data sheet | ICSC 0121
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H301, H302, H332, H351, H410

GHS precautionary statements

| P201, P202, P261, P264, P270, P271, P273, P281, P301+310, P301+312, P304+312, P304+340, P308+313, P312, P321, P330, P391, P405, P501
Flash point | 193-202 [1]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 710 mg/kg (rabbit, oral)
250 mg/kg (guinea pig, oral)
850 mg/kg (rat, oral)
759 mg/kg (dog, oral)
500 mg/kg (rat, oral)
150 mg/kg (cat, oral)
128 mg/kg (mouse, oral)
230 mg/kg (rat, oral)[2]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 5 mg/m3[1]

REL (Recommended)

| TWA 5 mg/m3[1]

IDLH (Immediate danger)

| 100 mg/m3[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

Spraying carbaryl on pine trees

Carbaryl (1-naphthyl methylcarbamate) is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations.[3][4] Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

## Contents

* 1 Production
* 2 Biochemistry
* 3 Applications
* 4 Ecology
* 5 Safety
* 6 References
* 7 External links

## Production

Carbaryl is often inexpensively produced by direct reaction of methyl isocyanate with 1-naphthol.[5]

C10H7OH + CH3NCO → C10H7OC(O)NHCH3

Alternatively, 1-naphthol can be treated with excess phosgene to produce 1-naphthylchloroformate, which is then converted to carbaryl by reaction with methylamine.[5] The former process was carried out in Bhopal. In comparison, the latter synthesis uses exactly the same reagents, but in a different sequence. This procedure avoids the potential hazards of methyl isocyanate.

## Biochemistry

Carbamate insecticides are slowly reversible inhibitors of the enzyme acetylcholinesterase. They resemble acetylcholine, but the carbamoylated enzyme undergoes the final hydrolysis step very slowly (minutes) compared with the acetylated enzyme generated by acetylcholine (microseconds). They interfere with the cholinergic nervous system and cause death because the effects of the neurotransmitter acetylcholine cannot be terminated by carbamoylated acetylcholinesterase.

## Applications

The development of the carbamate insecticides has been called a major breakthrough in pesticides. The carbamates do not have the persistence of chlorinated pesticides. Although toxic to insects, carbaryl is detoxified and eliminated rapidly in vertebrates. It is neither concentrated in fat nor secreted in milk, so is favored for food crops, at least in the US.[6] It is the active ingredient in Carylderm shampoo used to combat head lice until infestation is eliminated.[7]

## Ecology

Carbaryl kills both targeted (e.g., malaria-carrying mosquitos) and beneficial insects (e.g., honeybees), as well as crustaceans.[8] Because it is highly toxic to zooplankton, the algae they feed on experience blooms. Boone & Bridges 2003 find that larger algae eaters such as Bufo woodhousii benefit from this effect.[9]

Although it can increase survival rates for organisms that benefit from consequential algae blooms, the long term effects of these changes in competition levels and predation can be detrimental to many aquatic ecosystems, particularly those dominated by Anurans.[10]

It is approved for more than 100 crops in the US. Carbaryl is illegal in the EU[11] and Angola.[12]

## Safety

Carbaryl is a cholinesterase inhibitor and is toxic to humans. It is classified as a likely human carcinogen by the United States Environmental Protection Agency (EPA.)[13] The oral -1">50 is 250 to 850 mg/kg for rats and 100 to 650 mg/kg for mice.[8]

Carbaryl can be produced using methyl isocyanate (MIC) as an intermediary.[5] A leak of MIC used in the production of carbaryl caused the Bhopal disaster, the most lethal industrial accident in history.[14]

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 NIOSH Pocket Guide to Chemical Hazards. "#0100". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0100.html.
2. ↑ "Carbaryl". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/63252.html.
3. ↑ "When Familiar Pesticides Change". https://ucanr.edu/blogs/blogcore/postdetail.cfm?postnum=28074.
4. ↑ "When is Sevin not Sevin?". 14 February 2018. https://citybugs.tamu.edu/2018/02/14/sevin-not-sevin/.
5. ↑ 5.0 5.1 5.2 Thomas A. Unger (1996) (Google Books excerpt). Pesticide Synthesis Handbook. William Andrew. pp. 67–68. ISBN 0-8155-1401-8. https://books.google.com/books?id=blYN-_pY9_IC&pg=PA67.
6. ↑ Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
7. ↑ Carbaryl against lice
8. ↑ 8.0 8.1 Carbaryl General Fact Sheet - National Pesticide Information Center
9. ↑ Wildlife Toxicology: Emerging Contaminant and Biodiversity Issues. Boca Raton: CRC. 2010. ISBN 978-1-4398-1794-0. OCLC 646404494. 5.4.1 Taxon-Wide Impacts — Pesticides and Contaminants, and Their Roles in the Decline of Amphibian Populations. Moore, Robin D.; Claude Gascon. pp. 111-145.
10. ↑ Boone, Michelle D.; Semlitsch, Raymond D. (February 2002). [0307:ioaiwc2.0.co;2 "Interactions of an Insecticide With Competition and Pond Drying in Amphibian Communities"]. Ecological Applications 12 (1): 307–316. doi:10.1890/1051-0761(2002)012[0307:ioaiwc2.0.co;2]. ISSN 1051-0761. http://dx.doi.org/10.1890/1051-0761(2002)012[0307:ioaiwc]2.0.co;2.
11. ↑ "L_2007133EN.01004001.XML". https://eur-lex.europa.eu/legal-content/EN/TXT/HTML/?uri=CELEX:32007D0355.
12. ↑ Carbaryl Insecticide Hazard Data
13. ↑ Interim Reregistration Eligibility Decision for Carbaryl , U.S. EPA, June 2003.
14. ↑ Eckerman, Ingrid (2005). The Bhopal Saga—Causes and Consequences of the World's Largest Industrial Disaster. India: Universities Press. doi:10.13140/2.1.3457.5364. ISBN 81-7371-515-7. https://docs.google.com/file/d/0B0FqO8XKy9NRZDNzTkZQeVJQbE0/edit?pli=1.

## External links

* Carbaryl Technical Fact Sheet - National Pesticide Information Center
* Carbaryl Pesticide Information Profile - Extension Toxicology Network
* Cholinesterase Inhibition - Extension Toxicology Network
* EPA info
* EPA factsheet
* IPCS (WHO) Health and Safety Guide
* Environmental Health Criteria - WHO
* Exclusive Chemistry Ltd - routes of Sevin synthesis
* CDC - NIOSH Pocket Guide to Chemical Hazards
* Carbaryl in the Pesticide Properties DataBase (PPDB)

* v
* t
* e

Pest control: Insecticides

Carbamates|

* Aldicarb
* Bendiocarb
* Carbaryl
* Carbofuran
* Ethienocarb
* Fenobucarb
* Oxamyl
* Methomyl
* 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
* Diflubenzuron
* Flufenoxuron
* Hydroprene
* Lufenuron
* Methoprene
* Pyriproxyfen

Neonicotinoids|

* Acetamiprid
* Clothianidin
* Dinotefuran
* Imidacloprid
* Nitenpyram
* Nithiazine
* 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
* 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
* Schradan
* Temefos
* Tebupirimfos
* Terbufos
* Tetrachlorvinphos
* Tribufos
* Trichlorfon

Pyrethroids|

* Acrinathrin
* Allethrins
* Bifenthrin
* Bioallethrin
* Cyfluthrin
* Cyhalothrin
* Cypermethrin
* Cyphenothrin
* Deltamethrin
* Empenthrin
* Esfenvalerate
* Etofenprox
* Fenpropathrin
* Fenvalerate
* Flumethrin
* Imiprothrin
* Metofluthrin
* Permethrin
* Phenothrin
* Prallethrin
* Pyrethrin (I, II; chrysanthemic acid)
* Pyrethrum
* Resmethrin
* Silafluofen
* Tefluthrin
* Tetramethrin
* Tralomethrin
* Transfluthrin

Ryanoids|

* Chlorantraniliprole
* Cyantraniliprole
* Flubendiamide
* Ryanodine
* Ryanodol

Other chemicals|

* Afoxolaner
* Amitraz
* Azadirachtin
* Buprofezin
* Chlordimeform
* Chlorfenapyr
* Cyromazine
* Fenazaquin
* Fenoxycarb
* Fipronil
* Fluralaner
* Hydramethylnon
* Indoxacarb
* Limonene
* Lotilaner
* Pyridaben
* Pyriprole
* Ryanodine
* Sarolaner
* Sesamex
* Spinosad
* Sulfluramid
* Tebufenozide
* Tebufenpyrad
* Veracevine
* Xanthone
* Metaflumizone

Metabolites|

* Oxon
* Malaoxon
* Paraoxon
* TCPy

Biopesticides|

* Bacillus thuringiensis
* Baculovirus
* Beauveria bassiana
* Beauveria brongniartii
* Metarhizium acridum
* Metarhizium anisopliae
* Nomuraea rileyi
* Lecanicillium lecanii
* Paecilomyces fumosoroseus
* Paenibacillus popilliae
* Purpureocillium lilacinum

* v
* t
* e

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)|

| ChAT|

* 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

|

AChE|

* 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
* Propamocarb
* Propham
* Propoxur
* Thiofanox; Stigmines: Distigmine
* Eptastigmine
* Ganstigmine
* Neostigmine
* Phenserine
* Physostigmine
* Pyridostigmine
* Quilostigmine
* Rivastigmine
* Terestigmine; Others: Acotiamide
* Ambenonium
* Caffeine
* Donepezil
* EA-3990
* EA-4056
* Edrophonium
* Galantamine
* Huperzine A
* Ipidacrine
* Itopride
* Ladostigil
* Minaprine
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* T-1123
* TL-599
* TL-1238
* Tacrine
* Zanapezil

* Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Acephate
* Anatoxin-a(S)
* 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
* Diisopropyl fluorophosphate
* Diisopropylphosphate
* 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
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fluorotabun
* Fonofos
* Formothion
* Fosthiazate
* GD-42
* GH
* GT-45
* GV
* Hexaethyl tetraphosphate
* Isofluorophate
* Isoxathion
* Leptophos
* Malaoxon
* Malathion
* Methamidophos
* Methidathion
* Methyl phenkapton
* Methylfluorophosphonylcholine (MFPCh)
* Metrifonate
* Mevinphos
* Mipafox
* Monocrotophos
* Naled
* Novichok agent
* Omethoate
* Oxydemeton-methyl
* Paraoxon
* Parathion
* Parathion-methyl
* Phorate
* Phosalone
* Phosfolan
* Phosmet
* Phosphamidon
* Phoxim
* Pirimiphos-methyl
* Profenofos
* Prothoate
* 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
* Sarin (GB)
* Schradan
* Soman (GD)
* Tabun (GA)
* Tebupirimfos
* Temefos
* Terbufos
* Tetrachlorvinphos
* Tetraethyl pyrophosphate
* 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

* Reactivators: Asoxime chloride
* Methoxime
* Obidoxime
* Pralidoxime
* Trimedoxime bromide

BChE|

* Inhibitors: Affinine
* Affinisine
* Conodurine
* Cymserine
* Ladostigil
* Profenamine (ethopropazine)
* Rivastigmine
* Tacrine
* ZINC-12613047
* Many of the other AChE inhibitors listed above

Transporter
(modulators)|

| CHT|

* Inhibitors: Hemicholinium-3 (hemicholine)
* Triethylcholine

* Enhancers: Coluracetam

|

VAChT|

* Inhibitors: Vesamicol

Release
(modulators)|

| Inhibitors|

* SNAP-25 inactivators: Botulinum toxin (A, C, E)

* VAMP inactivators: Botulinum toxin (B, D, F, G)

* Others: [[Chemistry:BungaroBungarotoxins (Beta-Bungarotoxin|β-bungarotoxin]], γ-bungarotoxin)

|

Enhancers|

* LPHN 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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Original source: https://en.wikipedia.org/wiki/Carbaryl. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Carbaryl&oldid=815037"
*[CID]: Compound ID
*[H301]: Toxic if swallowed
*[H302]: Harmful if swallowed
*[H332]: Harmful if inhaled
*[H351]: Suspected of causing cancer
*[H410]: Very toxic to aquatic life with long lasting effects
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P281]: Use personal protective equipment as required
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P391]: Collect spillage
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ChAT]: Choline acetyltransferase
*[AChE]: Acetylcholinesterase
*[BChE]: Butyrylcholinesterase
*[CHT]: Choline transporter
*[VAChT]: Vesicular acetylcholine transporter
*[SNAP-25]: Synaptosomal-associated protein 25
*[VAMP]: Vesicle-associated membrane protein
*[LPHN]: Latrophilin