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Aldoxycarb
ALDOXYCARB · ALDICARB-SULFONE PESTANAL · UCES · ent4.9 · Standak · STANDOK · UC21865 · Sulfocarb
Identifikatoren & physikalische Daten
| CAS No. | 1646-88-4 |
|---|---|
| Summenformel | C7H14N2O4S |
| Durchschnittliche Molmasse | 222,26 g/mol |
| Monoisotopische Masse | 222,06742793 g/mol |
| SMILES | CNC(=O)ON=CC(C)(C)S(C)(=O)=O |
| InChIKey | YRRKLBAKDXSTNC-UHFFFAOYSA-N |
| PubChem CID | 15438 |
| EC No. | 216-710-0 |
| DTXSID | DTXSID6023862 |
| Lokaler Name | Aldoxycarb |
Chemische & physikalische Eigenschaften
| XLogP | -0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 93,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 326 |
| Pestizide | Pesticide -> EPA IRISPesticides -> Carbamate InsecticidesPesticide (Aldicarb sulfone) -> USDA PDBPesticide degradation product |
| LogP (Verteilungskoeffizient) | -0.57 |
| Dampfdruck | 0.00009 [mmHg]1.2×10-2 Pa (25 °C) |
| Physical Description | Aldicarb sulfone is a white crystalline solid. Insecticide.White solid[CAMEO] |
| Collision Cross Section | 149.3 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID6023862] |
| Schmelzpunkt | 132-135 °C |
| Dichte | 1.3816 (rough estimate) |
| Brechungsindex | 1.5690 (estimate) |
| Lagerbedingungen | 0-6°C |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly)10 g l-1 (25 °C) |
| pKa (Säurekonstante) | 13.44±0.46(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| BRN | 2215242 |
| Henry-Konstante | 2.9×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C7H14N2O4S/c1-7(2,14(4,11)12)5-9-13-6(10)8-3/h5H,1-4H3,(H,8,10) |
| InChIKey | YRRKLBAKDXSTNC-UHFFFAOYSA-N |
| SMILES | CNC(ON=CC(C)(C)S(C)(=O)=O)=O |
| EPA chemische Informationen | Aldicarb sulfone (1646-88-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300 (92.9%): Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Gefahrenübersicht | Causes weight loss in acute oral studies of ratsCauses other degenerative changes to brain and effects on true cholinesterase in 13-week constant oral studies of rats[RTECS] A metabolite of aldicarb with less potent cholinesterase inhibiting potential[Reference #1] May cause irritationA lachrymator and cholinesterase inhibitorHighly toxic by ingestion, inhalation, and skin absorptionTargets the cardiovascular system, CNS, blood, heart, and eyes[Sigma-Aldrich MSDS] See Aldicarb. See CARBAMATE INSECTICIDES. |
| Reaktive Gruppe | Carbamates |
| Reactivity Profile | ALDICARB SULFONE is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Hazard Classes and Categories | Acute Tox. 2 (92.9%) |
| Brandbekämpfung | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Erste Hilfe | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Expositionsschutz und Persönliche Schutzausrüstung | Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs] |
| Freisetung ohne Brand | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Treatment | 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. |
| Zielorgane | Nervous |
| Gesundheitliche Auswirkungen | 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). |
| Unerwünschte Wirkungen | Other Poison - Carbamate |
| Expositionspfade | Inhalation (L793)oral (L793)dermal (L793) |
| Toxizitätsübersicht | Aldoxycarb 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 | 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) |
| EPA IRIS Information | Aldicarb sulfoneNervous1 x 10 ^-3 mg/kg-day |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | LC50 (rat) = 140 mg/m3/4hr |
| RAIS Toxicity Values | 0.001IRIS Current |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | Aldicarb sulfone68529Pesticide degradation productUSEPA OW recommends that the concentration of any combination of two or more of the three aldicarb compounds should not be greater than 7 ug/L because of similar mode of action. USEPA issued administrative stay on an MCL for aldicarb sulfone.Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 2757 |
| RTECS-Nr. | UE2080000 |
| R-Sätze (R) | 24-26/28 |
| Toxizität | duck,LD50,oral,33500ug/kg (33.5mg/kg),Pesticide Manual. Vol. 9, Pg. 18, 1991. |
| Gefahrensymbole | T+ |
| Sicherheitshinweise (S) | 28-36/37-45 |
| Gefahrenklasse | 6.1(a)Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Acute 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Beschreibung
Aldoxycarb, is also called 2-mesyl-2-methylpropionaldehyde O-methylcarbamoyloxime (IUPAC), the sulfone analog of aldicarb, is also a systemic insecticide effective for control of insects (mainly sucking insect pests such as aphids, leafhoppers, etc.).
Verwenden
Aldicarb Sulfone is an analog of Aldicarb (A514650) detected in agricultural products as pesticide residue.