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Natrium methyl[(4-aminophenyl)sulfonyl]carbamat

Asulam-sodium

HCID 13389335
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Grundinformationen

CAS
2302-17-2
Standard-SMILES
COC(=O)[N-]S(=O)(=O)c1ccc(N)cc1.[Na+]
InChIKey
PEXLHWBDBQUUOG-UHFFFAOYSA-M
Summenformel
C8H9N2NaO4S
Durchschnittliche Molmasse
252,23 g/mol
Monoisotopische Masse
252,01807223

Überblick

Asulam-sodium is an organic sodium salt obtained by formal reaction of equimolar amounts of azulam and sodium. A dihydropteroate synthase inhibitor, it is used as a herbicide (mainly for killing bracken). It has a role as a herbicide, an agrochemical and an EC 2.5.1.15 (dihydropteroate synthase) inhibitor. It contains an asulam(1-).

Namen und Bezeichner

Bevorzugter Name
Asulam-sodium
IUPAC
sodium (4-aminophenyl)sulfonyl-methoxycarbonylazanide
Lokaler Name
Natrium methyl[(4-aminophenyl)sulfonyl]carbamat
Englischer Name
Asulam sodium salt
Summenformel
C8H10N2O4S.Na
Molmasse
253.23

Namen und Synonyme

Asulam-sodiumSodium asulamASULAM SODIUMAsulam, sodium saltAsulox, sodium saltCaswell No. 062BKH98QH62MJMethyl sulfanilylcarbamate, sodium saltDTXSID1034420CHEBI:142672ARD-13/02Sodium methyl ((4-aminophenyl)sulphonyl)carbamate
Weitere Namen anzeigen
asulam sodium saltASULAM 400 HERBICIDEN-Sulphanilyl-N-sodiocarbamic acidSODIUMN-METHOXYCARBONYLSULFANILAMIDEN-Sulfanilyl-N-sodiocarbamic acid methyl esterSodium methyl [(4-aminophenyl)sulphonyl]carbamateN-(4-Aminophenyl)sulfonyl-N-sodiocarbamic acid methyl ester((4-aminophenyl)sulfonyl)carbamic acid methyl ester monosodium salt
Carbamic acid, sulfanilyl-, methyl ester, monosodium saltRefChem:1077325DTXCID9014420218-953-8sodium methyl N-(4-aminobenzenesulfonyl)carbamate2302-17-2Asulam-sodium [ISO]sodium;(4-aminophenyl)sulfonyl-methoxycarbonylazanide

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
95,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
3
Schwere Atome
16
Formalladung
0
Komplexität
319

Experimentelle und physikochemische Eigenschaften

Pesticides · 3 Einträge

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Carbamate

Physical DescriptionFormulated as soluble/concentrate liquid; [Reference #1] Brown odorless liquid; [Bayer CropScience MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
240 °C · 240 °C
Aggregatzustand
Crystal
Farbe
Colorless
Geruch (Odor)
Odorless
EPA chemische Informationen
Sodium asulam (2302-17-2)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 2 Einträge

Regulation (EC) No 1107/2009 (amended)

2008/934, Reg. (EU) 2024/425

Other Safety InformationIMAP assessments - Carbamic acid, [(4-aminophenyl)sulfonyl]-, methyl ester, monosodium salt: Environment tier I assessment
Hazards SummaryThe only registered product is the sodium salt; [Reference #1] An eye irritant; May causes skin sensitization; Harmful by ingestion, inhalation, and skin absorption; [Bayer CropScience MSDS] See Asulam.
Hazard Classes and Categories · 2 Einträge

Skin sensitisation - category 1

Skin Sens. 1

Toxikologische Informationen

Treatment · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

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

Verwendung und Herstellung

Uses · 3 Einträge

Used as selective pre-emergence herbicide mainly on sugarcane; Also used on ornamentals, turf, and other non-crop land; [Reference #1]

Farming (Pesticides) [Category: Industry]

This is a man-made compound that is used as a pesticide.

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Datenbank-Bezeichner

CAS
2302-17-2
PubChem CID
13389335
DTXSID
DTXSID1034420
ChEBI
CHEBI:142672
UNII
KH98QH62MJ
Health Effects · 1 Eintrag

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. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 Eintrag

Asulam, sodium salt is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. 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. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Signs and Symptoms · 1 Eintrag

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).
Toxicity DataLC50 (rat) > 5,000 mg/m3/4hr

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H317