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HCID 18752Erstellt: 25. Oktober 2026

Asulam

asulox · ASULAM · ASILAN · Asulon · plakin · Jonnix · Arulam · Asilam

https://huagongshe.com/de/chemical/18752

Molekülstruktur von Asulam

Identifikatoren & physikalische Daten

CAS No.3337-71-1
SummenformelC8H10N2O4S
Durchschnittliche Molmasse230,24 g/mol
Monoisotopische Masse230,0361278 g/mol
SMILESCOC(=O)NS(=O)(=O)c1ccc(N)cc1
InChIKeyVGPYEHKOIGNJKV-UHFFFAOYSA-N
PubChem CID18752
ChEMBLCHEMBL2137678
ChEBICHEBI:81696
EC No.222-077-1
DTXSIDDTXSID8023890
Lokaler NameAsulam

Chemische & physikalische Eigenschaften

XLogP-0,3
Polarare Oberfläche (TPSA)107
H-Brücken-Donoren2
H-Brücken-Akzeptoren5
Frei drehbare Bindungen3
Schwere Atome15
Formalladung0
Komplexität314
SpringerMaterials PropertiesFusion temperature
PestizidePesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, CarbamateEnvironmental transformation -> Pesticides (parent, predecessor)Pesticide (Asulam) -> USDA PDB
LogP (Verteilungskoeffizient)log Kow = -0.27
Color/FormWhite crystalsColorless crystals
LöslichkeitIn water, 5.0X10+3 mg/L at 22 °CIn water, 5 g/LSolubility: water, 0.5%Stable in boiling water over 6 hoursFor more Solubility (Complete) data for Asulam (7 total), please visit the HSDB record page.DMSO (Slightly), Methanol (Slightly)5g/L(room temperature)
Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits very toxic fumes of /nitrogen oxides and sulfur oxides/.
Schmelzpunkt144.2 °CMP: 143-144 °C (decomposes)142-144°C (dec.)
Dampfdruck0.00000144 [mmHg]
Physical DescriptionWhite solid[Merck Index]
Dissociation ConstantspKa = 4.82
Collision Cross Section150.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID8023890]
Dichte1.4655 (rough estimate)
Brechungsindex1.5690 (estimate)
Lagerbedingungen0-6°C
pKa (Säurekonstante)4.82(at 25℃)
FarbePale Brown to Light Brown
Merck13,862
BRN2697523
Hauptanwendungenagricultureenvironmental
InChI1S/C8H10N2O4S/c1-14-8(11)10-15(12,13)7-4-2-6(9)3-5-7/h2-5H,9H2,1H3,(H,10,11)
InChIKeyVGPYEHKOIGNJKV-UHFFFAOYSA-N
SMILESCOC(=O)NS(=O)(=O)c1ccc(N)cc1
LogP (Verteilungskoeffizient)-0.270
NIST chemische InformationenAsulam(3337-71-1)
EPA chemische InformationenAsulam (3337-71-1)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 4.2% (3 of 71) of reports.WarningH302 (95.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 71 reports by companies from 3 notifications to the ECHA C&L Inventory.
Regulatorische InformationenAsulam + sodium salt is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)Reg. (EU) 1045/2011Asulam: Does not have an individual approval but may be used under an appropriate group standardThe 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.)
Weitere SicherheitsinformationenIMAP assessments - Carbamic acid, [(4-aminophenyl)sulfonyl]-, methyl ester: Environment tier I assessment
GefahrenübersichtThyroid follicular hyperplasia observed in male rats at the LOAEL (180 mg/kg/day) following two year chronic feeding studyOther sub-chronic animal studies produced increase in absolute and relative thyroid weightsConsiderable reduction in live births per litter observed in two generation study of rats[Reference #1] A mild skin and moderate eye irritant in rabbitsSolid evidence of skin sensitization in Maximisation testTargets thyroid and erythrocytes in 90 day rat studyThyroid identified as target organ in dogs as wellHematological and histopathological effects consistent with mild anemia noted in chronic rodent studiesAdrenal medullary hyperplasia and limited evidence of carcinogenicity (phaeochromocytoma of higher frequency) observed at highest doses in male rats in chronic studiesMulti-generational rat study produced reduction in litter size (doses >= 5000 ppm)No evidence of teratogenicity, developmental toxicity, or cholinesterase inhibition[EFSA] See Asulam-sodium.
Special ReportsUSEPA/Office of Prevention, Pesticides and Toxic SubstancesReregistration Eligibility Decision Document - Asulam, EPA 738-R-95-024 (September 1995). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of July 3, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]
FIFRA-AnforderungenTolerances are established for the combined residues of asulam (methyl sulfanilylcarbamate) and its sulfanilamide containing metabolites in or on the following food commodities:[Table#6058]Based on the reviews of the generic data for the active ingredients asulam and its sodium salt, the Agency has sufficient information on the health effects of asulam and its sodium salt and on its potential for causing adverse effects in fish and wildlife and the environment. Although levels of concern are exceeded for endangered and non-endangered plant species and surfacewater and groundwater quality, the Agency concludes that products containing asulam and its sodium salt for all uses, with the exception of sugarcane, once amended to reflect the risk mitigation measures imposed in this RED, are eligible for reregistration.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Asulalm is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0265Pesticide type: herbicideRegistration Standard Date: 12/31/87Case Status: RED Approved 06/95OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.Active ingredient (AI): asulamData Call-in (DCI) Date(s): 08/07/91, 10/11/95AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Sodium asulalm is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0265Data Call-in (DCI) Date(s): 08/07/91, 03/03/95, 10/11/95, 10/13/95AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI. /Asulam sodium/
Hazard Classes and CategoriesAcute Tox. 4 (95.8%)
Skin, Eye, and Respiratory IrritationsApplication of technical asulam to rabbit eyes produced mild chemosis, irritation, and redness which cleared by day seven posttreatment. Asulam was not an irritant in a primary skin irritation study in rabbits. It did not cause dermal sensitization in guinea pigs.
EntsorgungsverfahrenSRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Allowable TolerancesTolerances are established for the combined residues of asulam (methyl sulfanilylcarbamate) and its sulfanilamide containing metabolites in or on the following food commodities:[Table#6057]
TreatmentIf 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.
ZielorganeHepatic
Gesundheitliche AuswirkungenAcute 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.
ÖkotoxizitätswerteLC50Species: Anas platyrhynchos (Mallard Duck)diet >75000 ppm for 8 days /60% purity/Species: Phasianus colchicus (Ring-Necked Pheasant) age 7 days
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 40 and 300(2,3) indicate that asulam is expected to have high to moderate mobility in soil(SRC). The pKa of asulam is 4.82(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Asulam is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). Asulam exhibited photolytic degradation half-lives of 40 and 208 hrs in air-dried and moist soil , respectively(7). Biodegradation half-lives of 8-28 days in soil(8) suggest that biodegradation is an important environmental fate process in soil(SRC).FIELD STUDY: Asulam, applied at 2.5 kg/ha to three Saskatchewan, Canada (sandy loam, heavy clay, silty clay) soils was present at less than 5% in the 12 months following May 1975-1977 applications(1).AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 40 and 300(2,3) indicate that asulam is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.82(4) indicates asulam will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.27(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Asulam is stable to hydrolysis at pH's of 5, 7 and 9(8). The compound photodegrades very rapidly in aqueous solution at pH 9 (half-life = 2 hrs)(8). A biodegradation half-life of greater than 1 year(6) indicates that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), asulam, which has an estimated vapor pressure of 1.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase asulam is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 15 hrs(SRC), calculated from its rate constant of 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase asulam may be removed from the air by wet and dry deposition(SRC). Asulam absorbs UV at wavelength 270 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Unerwünschte WirkungenSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
ExpositionspfadeInhalation (L793)oral (L793)dermal (L793)
ToxizitätsübersichtIDENTIFICATION AND USE: Asulam is a herbicide used for weed control. Asulam is formulated into and applied as the asulam sodium salt. HUMAN STUDIES: In vitro cytogenetics assay in human lymphocytes were negative for asulam. ANIMAL STUDIES: Application of technical asulam to rabbit eyes produced mild chemosis, irritation, and redness which cleared by day seven posttreatment. Asulam was not an irritant in a primary skin irritation study in rabbits. It did not cause dermal sensitization in guinea pigs. In a six-month feeding study of asulam in beagle dogs doses of asulam at 300 mg/kg/day and 1,500 mg/kg/day were associated with reductions in food consumption, body weight gain, emesis, diarrhea, and reductions in red blood cells, hemoglobin and packed cell volume. There were also elevated thyroid and kidney weights and reduced testicular weights. In a two-year carcinogenicity study mice, asulam was administered in the diet at 0, 500, 5,000 or 50,000 ppm. There was no increase in the incidence of any tumors. A two-year combined chronic feeding/carcinogenicity study was conducted using rats. Hyperplastic changes were observed in the adrenal medulla and in thyroid follicular cells of males at the doses of 180 and 953 mg/kg/day. There was a statistically significant increase in thyroid gland c-cell carcinomas and in adenomas and carcinomas combined in both the low- and mid-dose males. There was a statistically-significant increase in benign adrenal medullary pheochromocytomas at the high dose in males. No teratogenic effects were produced by asulam in either rats or rabbits. The Ames Assay which is used to detect gene mutation with Salmonella typhimurium was negative. Mutagenicity assays which detect structural chromosome aberrations included the dominant lethal test in mice and were negative for asulam. ECOTOXICITY STUDIES: When tested in bobwhite quail (Colinus virginianus) dietary study, asulam had no effect on food consumption, body weight, or cumulative mortality, and no signs of toxicity were seen during the 28-day feeding period. Similarly, the chemical had no effect on egg production, fertility, or hatchability of fertile eggs, or on abnormalities in the F1 generation.Asulam 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.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.
Ökotoxizitätsauszüge/BIRDS and MAMMALS/ Sixteen, 22, and 27 week old bobwhite quail (Colinus virginianus) were maintained for 4 weeks on diets containing 0, 1.5, 6.0, or 25.0 ppm asulam. During the following 3 weeks, they were maintained on normal diets without asulam. The pesticide residues in various tissues were analyzed using the Bratton-Marshall reaction. Asulam had no effect on food consumption, body weight, or cumulative mortality, and no signs of toxicity were seen during the 28-day feeding period. Similarly, the chemical had no effect on egg production, fertility, or hatchability of fertile eggs, or on abnormalities in the F1 generation. The amounts of asulam recovered from the tissues varied according to the tissues studiedthe kidenys, leg muscles, and liver contained the greatest amounts, 0.13, 0.14, and 0.11 ppm, respectively. During the withdrawal period, the liver contained 0.12 ppm asulam, but residues were not found in any other tissues. The data indicate that there are no imminent or long term hazards to quail from the application of asulam in the field./AQUATIC SPECIES/ The fungicide fluazinam, the insecticide lambda-cyhalothrin, and the herbicides asulam and metamitron were applied to indoor freshwater microcosms (water volume approximately 0.6 cu m). The treatment regime was based on a realistic application scenario in tulip cultivation. Concentrations of each pesticide were equal to 0%, 0.2%, 0.5%, 2%, and 5% spray drift emission of label-recommended rates. Contribution of compounds to the toxicity of the pesticide package was established by expressing their concentrations as fractions of toxic units. The fate of the compounds in the water, and responses of phytoplankton, zooplankton, periphyton, macroinvertebrates, macrophytes, decomposition, and water quality were followed for 13 weeks. The half-lives of lambda-cyhalothrin, metamitron, and fluazinam were 1 to 2 dthat of asulam was >30d. No consistent effects could be demonstrated for the 0.2% treatment regime that was therefore considered the no-observed-effect concentration (NOEC). The macroinvertebrate populations of Gammarus pulex, Asellus aquaticus, and Proasellus meridianus were the most sensitive end points, followed by species of copepods and cladocerans. Responses mainly were due to lambda-cyhalothrin. The 0.5% treatment regime resulted in short-term effects. Pronounced effects were observed at the 2% and 5% treatment levels. At the end of the experiment, the macrophyte biomass that consisted of Elodea nuttallii, showed a decline at the two highest treatment levels, asulam being the causal factor (NOEC: 0.5% treatment level). Primary production was reduced at the 5% treatment level only. In our experiment, the first-tier risk assessment procedure for individual compounds was adequate for protecting sensitive populations exposed to realistic combinations of pesticides. Spray drift reduction measures seem to be efficient in protecting aquatic ecosystems in agricultural areas.
Signs and SymptomsAs 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)
Ongoing Test StatusEPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of August 9, 2018: http://actor.epa.gov/dashboard/]
EPA IRIS InformationAsulamHepatic5 x 10 ^-2 mg/kg-day
Wassergefährdungsklasse (WGK)3
Zollcode29350090
RTECS-Nr.FD1190000
R-Sätze (R)22
ToxizitätLD50 in rats, mice, dogs, rabbits (mg/kg): >5000, >5000, >5000, >2000 orallyin rats (mg/kg): >1200 dermally (Brockelsby)
GefahrensymboleXn
Lagerklasse13 - Non Combustible Solids
Gefahrstoffdaten3337-71-1(Hazardous Substances Data)
GefahrenklasseAcute Tox. 4 Oral

Anwendungen & Verwendung

Beschreibung

Asulam is a sulfonamide and can be formulated as a sodium salt. It is very water soluble and is a very systemic herbicide following foliar and root uptake, owing to its physicochemical properties (Table 1). The Log P (Kow) of 1.01 and pKa of 4.82 are optimal for phloem mobility in the plant (4). These properties contribute to the herbicidal effectiveness against perennial weeds where translocation to underground meristematic organs is essential for effective control.

Verwenden

Carbamate herbicide; folic acid biosynthesis inhibitor.