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Karbutilate

HCID 312440
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
4849-32-5
Standard SMILES
CN(C)C(=O)Nc1cccc(OC(=O)NC(C)(C)C)c1
InChIKey
OWNAXTAAAQTBSP-UHFFFAOYSA-N
Molecular formula
C14H21N3O3
Average molar mass
279.33 g/mol
Monoisotopic mass
279.15829154

Overview

Karbutilate is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

Names & identifiers

Preferred name
Karbutilate
IUPAC
[3-(dimethylcarbamoylamino)phenyl] N-tert-butylcarbamate
English name
KARBUTILATE
Molecular formula
C14H21N3O3
Molecular weight
279.33

Names & synonyms

Karbutilate4849-32-5TandexCarbutilatem-(3,3-Dimethylureido)phenyl tert-butylcarbamate3-(3,3-Dimethylureido)phenyl tert-butylcarbamateBACKUP FLOWABLE3-(3,3-Dimethylureido)phenyl N-tert-butylcarbamatem-(3,3-Dimethylharnstoff)-phenyl-tert-butylcarbamatm-(3,3-Dimethylureido)phenyl tertbutyl carbamate49A0A2590DNSC-222508
Show more names
tanzenecga61837fmc11092nia11092NSC 222508KARBUTYLATKARBUTYLATE
Carbamic acid, tert-butyl-, ester with 3-(m-hydroxyphenyl)-1,1-dimethylurea(1,1-Dimethylethyl)carbamic acid 3-(((dimethylamino)carbonyl)amino)phenyl esterNIA-11092Carbamic acid, (1,1-dimethylethyl)-, 3-(((dimethylamino)carbonyl)amino)phenyl esterCarbamic acid, (1,1-dimethylethyl)-, 3-[[(dimethylamino)carbonyl]amino]phenyl esterRefChem:1509753-((dimethylcarbamoyl)amino)phenyl N-tert-butylcarbamate3-(((dimethylamino)carbonyl)amino)phenyl(1,1-dimethylethyl)carbamate

Database identifiers

CAS
4849-32-5
PubChem CID
312440
DTXSID
DTXSID0042084
ChEMBL
CHEMBL2252176
UNII
49A0A2590D
EC Number
225-439-7
Nikkaji
J3.068F

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
70.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
20
Formal charge
0
Complexity
350

Experimental & physicochemical properties

Pesticides · 2 items

Herbicides

Active substance -> EU Pesticides database: Not approved

LogP1.66
Collision Cross Section175.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0042084]

Physicochemical properties

Melting point
169 · 169-169.5℃
Boiling point
422.1 °C · 422.1°C (rough estimate)
Density
1.1119 · 1.1119 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
Flash point
100 °C · >100 °C
storage temp.
0 · 0-6°C
pka
12.28 · 12.28±0.46(Predicted)
Water Solubility
325 mg/L · 325mg/L(room temperature)
BRN
2871986 · 2871986
Henry's Law Constant
1.8 · 1.8×108 mol/(m3Pa) at 25℃, Ebert et al. (2023)
FDA UNII
49 A0A2590D · 49A0A2590D
EPA Substance Registry System
Karbutilate (4849-32-5)
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
400 · H400-H319
Precautionary statements
273 · P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P
WGK Germany
2 · 2
RTECS
9980000 · EY9980000
HS Code
29242990 · 29242990

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Warning

H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Hazard information

Regulatory Information2002/2076
Other Safety InformationIMAP assessments - Carbamic acid, (1,1-dimethylethyl)-, 3-[[(dimethylamino)carbonyl]amino]phenyl ester: Environment tier I assessment
Hazard Classes and CategoriesEye Irrit. 2 (100%)

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Karbutilate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Signs and Symptoms · 1 item

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
2
rtecs
EY9980000
hs_code
29242990
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
Hazard statements
H400-H319
Precautionary statements
P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

UsesKarbutilate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Applications · 1 item

UsesKarbutilate (Standard) is the analytical standard of Karbutilate. This product is intended for research and analytical applications. Karbutilate (NIA-11092) is a nonselective soil-active herbicide which is used to kill one-leaf pinyon saplings.

Suppliers16 total

Syntechem Co.,Ltd[email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海毕楷科技有限公司18516304666 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
深圳市丽晶生化科技有限公司0755-85201366 18938635012 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

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