基本情報
- 標準SMILES
CNC(=O)Oc1cccc2ccccc12- InChIKey
CVXBEEMKQHEXEN-UHFFFAOYSA-N- 分子式
- C12H11NO2
- 平均分子量
- 201.22 g/mol
- 単同位体質量
- 201.07897859
概要
Carbaryl can cause cancer according to The Environmental Protection Agency (EPA). It can cause developmental toxicity, female reproductive toxicity and male reproductive toxicity according to The National Institute for Occupational Safety and Health (NIOSH).
名称と識別子
- 優先名称
- Carbaryl
- IUPAC
- naphthalen-1-yl N-methylcarbamate
- 英語名
- naphthalen-1-yl N-methylcarbamate
- 分子式
- C12H11NO2
- 分子量
- 0
名称と別名
名称をさらに表示
データベース識別子
- CAS
27636-33-5、3197-92-0、63-25-2- PubChem CID
- 6129
- DTXSID
DTXSID9020247- ChEMBL
CHEMBL46917- ChEBI
CHEBI:3390- UNII
- R890C8J3N1
- EC Number
- 200-555-0
- Nikkaji
- J2.354J
物性
構造計算による物性
- XLogP
- 2.4
- 極性表面積
- 38.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 15
- 形式電荷
- 0
- 複雑度
- 230
実験および物理化学的性質
Pesticides
Pesticides
Pesticide -> EPA IRIS
Insecticides, Plant Growth Regulators
Active substance -> EU Pesticides database: Not approved
Pesticides -> Carbamate Insecticides
Pesticide
LogP
log Kow = 2.36
1.59
Density
1.23 at 68 °F (USCG, 1999) - Denser than water; will sink
1.228 g/cu cm at 25 °C
1.2 g/cm³
1.23
1.228 @25 °C
1.23
Color/Form
Colorless to light tan crystals
White or gray ... solid.
Solubility
0.01 % (NIOSH, 2024)
Soluble in most polar organic solvents; dimethylformamide 400-450, dimethyl sulfoxide 400-450, acetone 200-300, cyclohexanone 200-250, isopropanol 100, xylene 100 (all in g/kg at 25 °C)
In water, 110 mg/L at 22 °C
Solubility in water, g/100ml at 30 °C: 0.004-0.012 (very poor)
>30.2 [ug/mL] (The mean of the results at pH 7.4)
0.01%
Boiling Point
Decomposes (NIOSH, 2024)
Decomposes
decomposes
Decomposes
安全と法規制
GHS分類
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H301 (63.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P270, P271, P273, P280, P301+P316, P301+P317, P304+P340, P317, P318, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Hazard Traits - Carcinogenicity; Developmental Toxicity; Neurotoxicity; Reproductive Toxicity
Commission Regulation (EC) No 451/2000
2007/355
Carbaryl: HSNO Approval: HSR002822 Approved with controls
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.)
Fire Hazards
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Combustible. Liquid formulations containing organic solvents may be flammable.
Fire Potential
... FLAMMABILITY POINT OF 193 °C.
Material itself does not burn or burns with difficulty.
Hazards Summary
Carbaryl is an insecticide used on a variety of crops. Acute (short-term) and chronic (long-term) occupational exposure of humans to carbaryl has been observed to cause cholinesterase inhibition, and reduced levels of this enzyme in the blood cause neurological effects. These effects appear to be reversible upon discontinuation of exposure. Headaches, memory loss, muscle weakness and cramps, and anorexia are caused by prolonged low-level exposure to carbaryl resulting from cholinesterase inhibition. EPA has classified carbaryl as a Group D, not classifiable as to human carcinogenicity.
Classified as highly toxic, moderately toxic or slightly toxic depending on the formulation; [EXTOXNET] Allergic contact dermatitis in pesticide handlers is most likely due to maneb, carbofuran, carbaryl, captan, folpet, or captafol. [Marks, p. 312] Carbaryl causes testicular damage in high-dose animal studies. [ATSDR Case Studies #29] TLV Basis: Cholinesterase inhibition; Male reproductive & embryo damage; [ACGIH] See CARBAMATE INSECTICIDES.
Special Reports
USEPA/Office of Pesticides Programs; Interim Reregistration Eligibility Decision for Carbaryl. 318 pp. (October 22, 2004)[Available from, as of November 4, 2008: http://www.epa.gov/oppsrrd1/REDs/carbaryl_ired.pdf]
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision for Carbaryl. 47 pp.EPA-738RO7-018 (September 2007)[Available from, as of November 4, 2008: http://www.epa.gov/oppsrrd1/REDs/carbaryl_red.pdf]
WHO; Poisons Information Monograph 147 Carbaryl. (October 1997).[Available from, as of December 1, 2008: http://www.inchem.org/documents/pims/chemical/pim147.htm]
United Nations Environment Programme, ILO, WHO; Health and Safety Guide No. 78 for Carbaryl. (1992)[Available from, as of December 1, 2008: http://www.inchem.org/documents/hsg/hsg/hsg78_e.htm]
For more Special Reports (Complete) data for CARBARYL (9 total), please visit the HSDB record page.
安全と保護具
Fire Fighting
Fire Extinguishing Agents: Solution fires; Water, foam, dry chemical, CO2 (USCG, 1999)
Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give a slurry of activated charcoal in water to drink. Give one or two glasses of water to drink. Refer for medical attention .
First Aid
Excerpt from NIOSH Pocket Guide for Carbaryl:
(General first aid procedures)
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
5.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting Procedures
/Wear/ self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode /when fighting fire/.
Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) /Carbamate pesticide, solid, toxic, not otherwise specified
If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos/
Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos ; carbamate pesticides, liquid, flammable, toxic, nos/
Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, solid, nos/
Storage Conditions
PESTICIDE STORAGE: Storage should be under lock and key and secure from access by unauthorized persons and children. Storage should be in a cool, dry area away from any heat or ignition source. Do not allow storage in a damp or humid area. Do not stack over 2 pallets high. Move bags carefully so as not to tear or puncture. Do not move from one area to another unless they are securely sealed to prevent dust from escaping. Keep container tightly sealed when not in use. Keep away from any puncture source. Avoid storage near water supplies, food, feed and fertilizer to avoid contamination. Avoid contamination with acids and alkalies. Store in original containers only.
KEEP IN COOL, DRY PLACE. STORE AWAY FROM FEED & FOODSTUFFS. KEEP OUT OF REACH OF CHILDREN.
Cleanup Methods
Store in original containers only. If the contents are leaking or material is spilled, follow these steps while wearing protective equipment. 1. Collect and place in suitable containers for disposal. 2. Wash area with soap and water to remove remaining pesticides. 3. Follow washing with clear water rinse. 4. Do not allow runoff to enter sewer or contaminate water supplies.
Steps to be taken in case of material leak or spill: Pick up spilled material and place in suitable container. Decontaminate area with alkaline solution. Assure that proper protective equipment is worn. Prevent runoff.
A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. The first step is the flocculation/coagulation and sedimentation of the pesticide-contaminated wash water. The supernatant from the first step is then passed through activated carbon columns. /Pesticides/
Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Carbaryl (agricultural insecticides, nec, liquid)/
For more Cleanup Methods (Complete) data for CARBARYL (7 total), please visit the HSDB record page.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U279, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
PESTICIDE DISPOSAL /Powders/: Wastes resulting from the /agricultural/ use of this product may be disposed of on site or at an approved waste disposal facility. CONTAINER DISPOSAL /powders/: Completely empty bag into application equipment. Then dispose of empty bag in /accordance with local, state, and Federal regulations/.
CONTAINER DISPOSAL /liquids/: Triple rinse (or equivalent). Then offer for recycling or reconditioning or puncture and dispose of in a sanitary /in accordance with local, state, and Federal regulations/.
Hydrolysis: For each 2.265 kg of actual carbaryl, add 0.906 kg of flake caustic (sodium hydroxide) (this amt was stated to be a 50% excess over the minimum required) and allow about 24 hr for completion of the reaction. The first step of the degradation would be: aryl-O-CO-NHR + H2O --- NaOH ---> aryl-OH- + (HO-CO-NHR). The carbamic acid at the right would decompose to the amine and carbon dioxide in neutral soln, or to sodium carbonate in excess base. In excess base the phenol would be converted to the salt, that is, NaO-aryl. Phenolic decomposition products of some carbamate pesticides may, under some circumstances, persist in the environment and harm specific ecosystems.
For more Disposal Methods (Complete) data for CARBARYL (6 total), please visit the HSDB record page.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Remove all ignition sources. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Preventive Measures
For the garden/ornamental dust on /residential/ vegetables/ornamentals scenario, all end-use products are to be packaged in ready-to-use (RTU) shaker can containers, with no more than 0.5 lb ai/container.
For the lawn care hose-end sprayer for liquid lawn broadcast scenario, all liquid formulation end-use products for lawncare are to be packaged in pint-size RTU hose-end sprayers.
Aerial applications are prohibited for the following: wettable powder formulations; and granular and bait formulations applied to corn (field, pop, and sweet), grain sorghum, alfalfa, rice, and sunflowers.
Users should wash hands thoroughly with soap and water before eating, drinking, chewing gum, using tobacco, or using the toilet.
For more Preventive Measures (Complete) data for CARBARYL (24 total), please visit the HSDB record page.
毒性情報
Body Burden
Carbaryl does not accumulate in tissues or persist in blood. It is quickly metabolized into 1-naphthol which is excreted in urine as the glucuronide or sulfate ester(1). The mean concn of carbaryl in personal air samples taken in Jacksonville, Florida for summer(1986) and spring(1987) were 28.3 and 0.8 ng/cu m, respectively(2). Carbaryl was also detected in personal air samples taken from Springfield, Massachusetts in spring(1987) at 0.1 ng/cu m(2).
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.
Interactions
Poisoning from organophosphates and carbamates is a significant cause of morbidity and mortality worldwide. Concerns have been expressed over the safety and efficacy of the use of oximes such as pralidoxime (2-PAM) in patients with carbamate poisoning in general, and more so with carbaryl poisoning specifically. The goal of the present study was to evaluate the role of 2-PAM in a mouse model of lethal carbaryl poisoning. ... Female ICR Swiss Albino mice weighing 25-30 g were acclimated to the laboratory and housed in standard conditions. One hundred and ten mice received an LD50 dose of carbaryl subcutaneously. Ten minutes later, they were randomized by block randomization to one of eight treatment groups: normal saline control, atropine alone, 100 mg/kg 2-PAM with and without atropine, 50 mg/kg 2-PAM with and without atropine, and 25 mg/kg 2-PAM with and without atropine. All medications were given intraperitoneally and the atropine dose was constant at 4 mg/kg. The single objective endpoint was defined as survival to 24 hours. Fatalities were compared using a Chi squared or Fisher's exact test. ... Following an LD50 of carbaryl, 60% of the animals died. Atropine alone statistically improved survival (15% lethality). High dose 2-PAM with and without atropine was numerically worse, but not statistically different from control. While the middle dose of 2-PAM was no different than control, the addition of atropine improved survival (10% fatality). Low-dose 2-PAM statistically improved survival (25% lethality). Atropine further reduced lethality to 10%. ... When appropriately dosed, 2-PAM alone protects against carbaryl poisoning in mice. Failure to demonstrate this benefit in other models may be the result of oxime overdose.
The influence of cimetidine on the pharmacokinetic and pharmacodynamic response to the insecticide carbaryl has been investigated in isolated human erythrocytes (red blood cells; RBC) and after oral administration of 1 mg/kg carbaryl to four normal subjects in the absence or presence of cimetidine (300 mg, 8/hr for 3 days). Carbaryl induced a concentration-dependent reduction of isolated RBC acetylcholinesterase activity requiring 1 ug/mL to achieve 20% inhibition. Cimetidine also induced a dose-dependent inhibition of RBC acetylcholinesterase activity, but at 40-fold higher concentrations. At high concentrations, cimetidine was additive to carbaryl-induced inhibition of RBC acetylcholinesterase, but exhibited no effect at the therapeutically relevant concentrations (10 ug/mL). After oral carbaryl administration to normal subjects, plasma concentrations rapidly rose to a peak, then declined with a half-life of 0.79 +/- 0.47 hr. Oral carbaryl clearance was 5.4 +/- 2.0 L/min. Peak plasma carbaryl concentrations were associated with 27% inhibition of RBC acetylcholinesterase activity, and the concentration associated with a reduction of RBC acetylcholinesterase activity of 20% was 0.02 microgram/ml. The terminal half-life for the dynamic response was 2.6 +/- 1.5 hr. After pretreatment with cimetidine, peak plasma carbaryl concentrations doubled and clearance was reduced (to 2.5 +/- 1.5 L/min) (P<0.05). However, half-life remained unchanged. Despite increased carbaryl levels, the maximum inhibition of RBC acetylcholinesterase activity was significantly reduced, and the concentration of carbaryl required to achieve 20% inhibition of RBC acetylcholinesterase activity was increased to approximately 0.5 ug/mL. These results are consistent with the hypothesis that carbaryl is metabolized by drug-metabolizing enzymes that can be inhibited by cimetidine.
The administration of 2-pyridine aldoxime methyl chloride (2-PAM Cl) is a standard part of the regimen for treatment of human overexposure to many organophosphorus pesticides and nerve agents. However, some literature references indicate that poisoning by carbaryl (1-naphthyl N-methyl carbamate), an insecticide in everyday use, is aggravated by the administration of 2-PAM Cl. This effect has been reported in the mouse, rat, dog and man. ... The inhibition of both eel acetylcholinesterase (eel AChE, EC 3.1.1.7) and human serum cholinesterase (human BuChE, EC 3.1.1.8) by carbaryl was enhanced by several oximes. Based on 95% confidence limits the rank order of potentiation with eel AChE was TMB-4 = Toxogonin > HS-6 = HI-6 > 2-PAM Cl. By the same criterion, the rank order of potentiation with human BuChE was TMB-4 > Toxogonin > HS-6 = 2-PAM Cl. Carbaryl-challenged mice also reflected a potentiation since TMB-4 exacerbated the toxicity more than 2-PAM Cl. Our hypothesis is that certain oximes act as allosteric effectors of cholinesterases in carbaryl poisoning, resulting in enhanced inhibition rates and potentiation of carbaryl toxicity.
Antidiuretic agent diazoxide ... incr 20-fold toxicity of carbaryl in pig.
For more Interactions (Complete) data for CARBARYL (13 total), please visit the HSDB record page.
Target Organs
Hepatic
respiratory system, central nervous system, cardiovascular system, skin, blood cholinesterase, reproductive system
Health Effects
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).
Ecotoxicity Values
LD50 Pheasant (3 month old males) oral >2000 mg/kg /95% pure/
LD50 Pheasant (3-4 month old females) oral 707 mg/kg /Formulation/
LD50 Sharp-tailed grouse (3-12 month old females) oral 780-1700 mg/kg /95% pure/
LD50 Canada goose oral 1790 mg/kg (95% confidence limits: 1480-2180 mg/kg) /50% pure/
For more Ecotoxicity Values (Complete) data for CARBARYL (121 total), please visit the HSDB record page.
Environmental Fate
CARBARYL PERSISTED LONGER IN SOIL WATER THAN IN LAKE WATER. FOUR DAYS AFTER TREATMENT OF SOIL WATER, 1-NAPHTHOL AS WELL AS CARBARYL WAS RECOVERED.
TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 230, 370, and 390(1,2) indicate that carbaryl is expected to have moderate mobility in soil(SRC). Volatilization of carbaryl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.8X10-9 atm-cu m/mole(3). Carbaryl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.36X10-6 mm Hg(4). Photolysis half-lives of carbaryl in soil irradiated at >290 nm ranged from 97 hours in dry Etowah soil (0.13% carbon) to 251 hr in dry Holston soil (0.60% carbon) and from 458 hr in wet Holston soil (pH 6.3 slurry) to 688 hours in water saturated Holston soil(5). In neutral and alkaline soils, carbaryl is expected to hydrolyze rapidly. In acidic soils, hydrolysis is expected to occur more slowly(5). Carbaryl had an average biodegradation half-life of 10 days in four different soils (a Pliocene sand, an organic-rich orchard soil, an agricultural soil and soil from a volcanic area)(6).
AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 230, 370, and 390(1,2) indicate that carbaryl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.8X10-9 atm-cu m/mole(4). According to a classification scheme(5), measured BCF values of 34, 30, and 9(6,7,8) suggest the potential for bioconcentration in aquatic organisms is low(SRC). At 20 °C, hydrolysis half-lives of carbaryl in water are 10.5 days, 1.8 days, 2.5 hours, and 15 min at pH values of 7, 8, 9, and 10, respectively(9). Photolysis half-life for carbaryl in sunlight was 6.6 days in distilled water(10). Carbaryl's half-lives in aquatic environments have been reported as 1.7 days in river water and 5.8 days in mountain streams(11). In raw seawater, carbaryl was biodegraded to undetectable levels within 96 hrs(12).
AQUATIC FATE: One ppm of carbaryl was incubated in autoclaved and unautoclaved creek water at 9 °C(1). After 50 days, an avg of 39.3% and 56.9% carbaryl was recovered from the unautoclaved and the autoclaved creek water samples, respectively(1). Avg recoveries from creek water and bottom sediments following addition of 1 ppm carbaryl were 11.8% and 16.2%, respectively, in non-autoclaved samples, after 50 weeks at 9 °C(1). Avg recoveries from creek water and bottom sediments were 12.8% and 45.1%, respectively, in autoclaved samples after 50 weeks at 9 °C(1). Recovery from pond water and bottom sediments following addition of 1 ppm carbaryl avgd 13.75% and 13.9%, respectively, after 42 days at 9 °C(1). Within 4 days of carbaryl addition to Fall Creek water, >60% of the carbaryl added at 30 ug/mL and 300 ng/mL was converted to carbon dioxide compared with <10% conversion of carbaryl added at 3.0 ug/mL and 30 ng/mL(2). Due to the rapid hydrolysis of carbaryl under the conditions of the experiment, it is not possible to determine how much carbon dioxide resulted from carbaryl biodegradation and how much from biodegradation of the hydrolysis product, 1-naphthol(2). Carbaryl was completely degraded after 4 weeks incubation in the dark at 21 °C in water from the Holland Marsh drainage canal(3). Carbaryl in streams, rivers and brooks as a result of forest spraying decayed with half-lives of 25, 28 and 23 hr, respectively(4). Carbaryl was incubated in estuarine water in the presence and absence of estuarine mud(5). In the absence of mud, 50% of the initial carbaryl had disappeared after 38 days at 8 °C and nearly all had disappeared after 17 days at 20 °C with 43% being converted to 1-naphthol(5). In the presence of mud, after 10 days at 8 °C, 90% of the initial carbaryl had been removed from the water. This was attributed to the adsorption of the carbaryl on the mud, in which degradation proceeded more slowly than in the sea water(5). Carbaryl was detectable in the mud for up to 3 weeks(5). Carbaryl persisted in mud treated with 10 pounds active ingredient per acre for up to 42 days(5). At neutral and basic pH values, carbaryl is expected to hydrolyze rapidly (half-life = 10.5 days at pH 7 and 20 degC; half-life = 1.8 days at pH 8 at 20 °C). The lifetime of carbaryl in water at pH 7 is about 70 days (99% hydrolyzed). In acidic water, hydrolysis is not expected to be significant (half-life = 1500 days at pH 5 and 27 °C; half-life = 406 days at pH 6 and 25 °C). The photolysis half-life of carbaryl calculated from experimentally determined parameters ranged from 52-264 hr for a summer day at latitude 40 degrees north. At pH values of 7 and above, hydrolysis is expected to predominate(SRC).
For more Environmental Fate (Complete) data for CARBARYL (6 total), please visit the HSDB record page.
Food Survey Values
In 665 samples of domestic large fruits, 13.9% tested positive for carbaryl at an avg concn of 0.064 ppm(1). Of imported fruit, only 9.4% tested positive for carbaryl at an avg concn of 0.001 ppm(1). Carbaryl was detected in 3.6% of 2904 domestic leaf and stem vegetables analyzed at an avg concn of 0.020 ppm(1). Carbaryl was detected in 6.2% of 725 domestic vine and ear vegetables analyzed at an avg concn of 0.013 ppm(1). Carbaryl was detected in 11.4% of 499 domestic beans analyzed at an avg concn 0.05 ppm(1). Carbaryl was detected in fruit ranging from trace amounts to 0.05 ppm with an avg concn of 0.005 ppm(2). Carbaryl was detected in infant diet, particularly sugar and adjuncts at 0.050 ppm(3). US food samples collected from 1980-83 contained carbaryl as follows: apples - 0.19-0.57 ppm; cabbage - <0.01-0.19 ppm; cantalope - 0.04 ppm; celery - <0.01-0.06 ppm; eggplant - 0.01-0.03 ppm; grapes - 0.05 ppm; oranges - 0.26 ppm; tomatoes - <0.01-0.016 ppm(4). In 21 domestic and 132 imported agricultural commodities surveyed from 1981-1986, carbaryl was detected ranging from 0.05 to greater than 2.0 ppm(5).
Carbaryl levels on domestic Canadian Produce(1).
Carbaryl levels on produce imported into Canada(1).
In an adult diet study from 1982-1986, food samples were collected from 4 geographical areas of the United States and analyzed for pesticide content. Carbaryl was detected, concn not specified, in 135 out of 3,744 food samples analyzed(1).
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Inhalation (L793) ; oral (L793); dermal (L793)
Milk Concentrations
After admin of (14)C-labeled carbaryl to lactating cows radioactive residues were observed in whole milk & in milk fat, tissues ... In addn to 1-naphthol in urine, 5 compounds were observed in feces & milk: 5,6-dihydroxy-5,6-dihydronaphthyl N-methylcarbamate; 1,5,6-trihydroxy-5,6-dihydronaphthalene; 1-naphthyl-N-hydroxymethylcarbamate; 4-hydroxy-1-naphthyl N-methylcarbamate; & unchanged carbaryl.
Toxicity Summary
Food represents the major source of carbaryl intake for the general population. ... The general population can be exposed to carbaryl during pest control operations in both the home & recreation areas. Workers can be exposed to carbaryl during its manufacture, formulation, packing, transportation, storage, & during & after application. ... Significant dermal exposure may occur in industrial & agricultural workers if protective measures are inadequate. Carbaryl is rapidly absorbed in the lungs & digestive tract. ... The principal metabolic pathways of carbaryl are ring hydroxylation & hydrolysis. As a result, numerous metabolites are formed & subjected to conjugation with the formation of water-soluble sulfates, glucuronides, & mercapturates, excreted in the urine. Hydrolysis results in the formation of 1-naphthol, carbon dioxide & methylamine. Hydroxylation produces 4-hydroxycarbaryl, 5-hydroxycarbaryl, N-hydroxymethylcarbaryl, 5-6-dihydro-5-6-dihydroxycarbaryl & 1,4-naphthalendiol. The principal metabolite in humans is 1-naphthol. Under normal exposure conditions, the accumulation of carbaryl in animals is unlikely. Carbaryl is excreted primarily via the urine, since the product of its hydrolysis, 1-naphthol, is mainly detoxified to water-soluble conjugates. Enterohepatic cycling of carbaryl metabolites is also considerable, especially after oral administration. ... Carbaryl metabolites are also present in a small percentage of the absorbed doses in saliva & milk. ... The acute toxicity for birds is low. ... Carbaryl is very toxic for honey-bees & earthworms. ... The acute toxicity ... varies considerably according to species, formulation & vehicle. ... Carbaryl is a mild eye irritant & has little or no sensitizing potential. ... Carbaryl has a low cumulative potential. Carbaryl has been shown to affect mammalian reproduction & perinatal development adversely in a number of species. Effects on reproduction include impairment of fertility, decreased litter size, & reduced postnatal viability. Developmental toxicity is seen as increased in utero death, reduced fetal weight, & the occurrence of malformation. With the exception of a small number of studies, all adverse reproductive & developmental effects were noted only at doses that caused overt maternal toxicity, &, in a number of cases, the maternal animal was more sensitive to carbaryl than the conceptus. The maternal toxic effects included lethality, decreased growth, & dystocia. ...The available evidence indicates that carbaryl does not have any DNA-damaging properties. ... Negative results were obtained in tests for gene mutations in a large number of bacterial assays ... The available database does not support the presumption that carbaryl poses a risk of inducing genetic changes in ... humans. Carbaryl has been studied for its carcinogenic potential in numerous studies on rats & mice. The results of most of these studies were negative ... The effects of carbaryl on the nervous system are primarily related to cholinesterase inhibition & are usually transitory. ... Carbaryl has been reported to affect coagulation ... Carbaryl binds free blood amino acids. Disturbances have been reported in the carbohydrate metabolism & protein synthesis & detoxification function of the liver in mammals. Carbaryl is a weak inducer of hepatic microsomal drug-metabolizing activity. ... Carbaryl has been reported to incr the gonadotropic function of the hypophysis of rats. Carbaryl is an inhibitor of cholinesterase activity. This effect is dose-related & quickly reversible. ... All identified metabolites of carbaryl are appreciably less active cholinesterase inhibitors than carbaryl itself. Carbaryl is easily absorbed /in humans/ through inhalation & via the oral route & less readily by the dermal route. Since the inhibition of cholinesterase is the principal mechanism of carbaryl action, the clinical picture of intoxication is dominated by ... symptoms, such as: increased bronchial secretion, excessive sweating, salivation, & lacrimation; pinpoint pupils, bronchoconstriction, abdominal cramps (vomiting & diarrhea); bradycardia; fasciculation of fine muscles (in severe cases, diaphragm & respiratory muscles also involved); tachycardia; headache, dizziness, anxiety, mental confusion, convulsions, & coma; & depression of the respiratory center. Signs of intoxication develop quickly after absorption & disappear rapidly after exposure ends.... In cases of occupational overexposure to carbaryl, mild symptoms are observed long before a dangerous dose is absorbed, which is why severe cases of occupational intoxication with carbaryl are rare. During agricultural application, dermal exposure may play an important role. ... The appearance of a skin rash after accidental splashing with carbaryl formulations has been described. ... The most sensitive biological indicator of carbaryl exposure is the appearance of 1-naphthol in the urine & the decr of cholinesterase activity in the blood. ... The hazards of carbaryl for human beings are judged to be low, because of its low vapor pressure, rapid degradation , rapid spontaneous recovery of inhibited cholinesterase, & the fact that symptoms usually appear well before a dangerous dose has accumulated in the body. ...
Carbaril 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.
法規制情報
RCRA Requirements
U279; As stipulated in 40 CFR 261.33, when carbaryl, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
FIFRA Requirements
Tolerances are established for residues of the insecticide carbaryl, 1-naphthyl N-methylcarbamate per se, in or on the following food commodities: [Table#2556]
Tolerances are established for residues of the insecticide carbaryl, 1-naphthyl N-methylcarbamate, including its metabolites: 1-naphthol (naphthyl-sulfate); 5,6-dihydrodihydroxycarbaryl; and 5,6-dihydrodihydroxy napthol, calculated as 1-naphthyl N-methylcarbamate and the free and conjugated residues of carbaryl: 5,6-dihydro-5,6-dihydroxy carbaryl and 5-methoxy-6-hydroxy carbaryl, in or on the following food commodities: [Table#2557]
A tolerance is established for residues of the insecticide carbaryl (1-naphthyl N -methylcarbamate), including its metabolites 1-naphthol (naphthyl sulfate), 5,6-dihydro-dihydroxycarbaryl and 5-methoxy-6-hydroxycarbaryl, calculated as 1-naphthyl N -methylcarbamate in or on the food commodity: milk.
Tolerances are established for residues of the insecticide carbaryl (1-naphthyl N -methylcarbamate) in or on the following food commodities: fruit, pome; pineapple.
For more FIFRA Requirements (Complete) data for CARBARYL (11 total), please visit the HSDB record page.
Atmospheric Standards
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Carbaryl is included on this list.
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
Carbaryl is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
State Drinking Water Guidelines
(AZ) ARIZONA 700 ug/L
(CA) CALIFORNIA 700 ug/L
(FL) FLORIDA 700 ug/L
(ME) MAINE 70 ug/L
(WI) WISCONSIN 960 ug/L
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薬理情報
Metabolism/Metabolites
Sevin, labeled with (14)C, is metabolized in insects, in rat, and by microsomal prepn of mouse, rat & rabbit liver, by aromatic hydroxylation, n-methyl hydroxylation, hydrolysis of carbamyl grouping, & by conjugation.
Of the metabolites identified in livestock commodities, five are considered significant ... : carbaryl; 5,6-dihydro-5,6-dihydroxy carbaryl; and 5-methoxy-6-hydroxy carbaryl and all residues which can be hydrolyzed to carbaryl, 5,6-dihydro-5,6-dihydroxy carbaryl, or 5-methoxy-6-hydroxy carbaryl under acidic conditions. The /EPA/ included these compounds in the dietary risk assessment for carbaryl, and in the reassessment of carbaryl tolerances for livestock commodities only.
Single oral dose of carbaryl was admin to rats. After extraction of ... urine, column & TLC chromotography, tentative identification was made for 1,5-naphthalenediol with small amt of carbaryl, 5-hydroxycarbaryl, & trace of n-hydroxymethylcarbaryl was also present. A major metab ... identified as 5,6-dihydro-5,6-dihydroxycarbaryl, was found free (1.4% of the dose) & as the glucuronide (10.5% of the dose). Naphthyl glucuronide & sulfate were also observed.
In urine of rats in addn to 1-naphthol, 1-naphthyl methylcarbamate N-glucuronide, 1-naphthyl methylimido-carbonate O-glucuronide, 4-(methylcarbamoyloxy)-1-naphthyl glucuronide, 1-naphthyl glucuronide, 1-naphthyl sulfate, 4-(methylcarbamoyloxy)-1-naphthyl sulfate, 3 unidentified cmpd & cmpd believed to be 1-naphthyl N-hydroxymethylcarbamate were observed. Similar results were observed with guinea pigs.
For more Metabolism/Metabolites (Complete) data for CARBARYL (17 total), please visit the HSDB record page.
Carbaryl has known human metabolites that include carbaryl methylol, 4-hydroxycarbaryl, and 5-hydroxycarbaryl.
MeSH Pharmacological Classification
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion
An in vitro dermal penetration study was conducted using both rat and human skin . This study showed that rat skin was 2.8 times more permeable to carbaryl than human skin.
Excretion--retention of ... carbaryl labeled in 3 different positions ... studied 48 hr after ip admin to rats. 65% of (14)C of carbonyl-(14)C-carbaryl was excreted in urine, 25% in expired air, 2% in feces, & 10% was retained ... highest levels of (14)C were present in liver, kidneys, heart, & corpuscles (erythrocytes & leukocytes). 58% of (14)C of n-methyl-(14)C-carbaryl was excreted in urine, 12% in expired air, 4% in feces, & 13% was retained ... (14)C was maximal in liver, kidneys, heart, lungs, & spleen, organs with high blood flow. 77% of (14)C of naphthyl-(14)C-carbaryl was excreted in urine, 9% in feces, & 7% was retained ... levels of (14)C in tissue were highest in kidneys, spleen, bone, & fat ... about 50% of (14)C had been excreted in 4 hr ... .
Of oral dose of (1-naphthyl-1-(14)C)-N-methylcarbamate given to rats, 53% & 82% were absorbed after 20 min & 1 hr, respectively. Carbaryl is absorbed very rapidly from lung, 2.5 times faster than from small intestine.
(14)C-carbaryl labeled in n-methyl group has been found in fetuses of pregnant rats, & mice. ... Autoradiographic study of (14)C-methyl-carbaryl in pregnant rat has shown that radiolabel was localized in eye, liver, & brain of fetus.
For more Absorption, Distribution and Excretion (Complete) data for CARBARYL (9 total), please visit the HSDB record page.
用途と製造
Uses
Carbaryl is used as an insecticide on corn, soybean, cotton, fruit, nut, and vegetable crops, as well as in home yards and gardens. Carbaryl is sold under the trade name Sevin.
A wide-spectrum insecticide that is also used as a molluscicide and an acaricide; [EXTOXNET]
Farming (Pesticides) [Category: Industry]
For carbaryl (USEPA/OPP Pesticide Code: 056801) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Used in agriculture to control pests on terrestrial food crops including fruit and nut trees, many types of fruit and vegetables, and grain crops; cut flowers; nursery and ornamentals; turf, including production facilities; greenhouses; golf courses; and in oyster beds. Carbaryl is also registered for use on residential sites (e.g., annuals, perennials, shrubs) by professional pest control operators and by homeowners on gardens, ornamentals and turfgrass.
For several decades, carbaryl has been used to control burrowing shrimp on tidal mudflats in Willapa Bay and Grays Harbor, Washington. ... The available data indicate that acute mortality will likely be near 100% for animals trapped on mudflats in the immediate application area and that carbaryl will likely drift off-site with the tide. Additionally, as part of a settlement agreement with the Washington Toxics Coalition, oyster growers on Willapa Bay and Grays Harbor have agreed to a 12-year phase-out of carbaryl use on oyster beds while they look for alternatives for controlling populations of burrowing shrimp.
Consumption Patterns
INSECTICIDE FOR CORN, 14%; VEGETABLES, 13%; SOYBEANS, 11%; COTTON, 4%; DECIDUOUS FRUITS & NUTS, 4%; TOBACCO, 4%; SORGHUM, 2%; ALFALFA, 1%; CITRUS, 1%; OTHER FIELD CROPS, 17%; FORESTS, 2%; LIVESTOCK & POULTRY, 1%; OTHER NON-AGRICULTURAL USES, 28% (1982)
1.5 million lbs on soybeans, 0.2 million lbs on corn, 0.2 million lbs on peanuts, 0.1 million lbs on tobacco, & 0.1 million lbs on other small grains (1982)
In 1988, about 25 million pounds of carbaryl was applied to crops on farms in the United States.
In 1979, carbaryl was used on 50% of the sweet corn acres at 2.7 lbs/acre. In 1992, no carbaryl use was reported for Minnesota. In New York and Pennsylvania, carbaryl was used at 4 lbs/acre while in 1991, it was used at 31 lbs/acre.
Methods of Manufacturing
... Produced from 1-naphthyl chloroformate and methylamine or by reaction of 1-naphthol with methyl isocyanate.
In a first step, sodium 1-naphthoxide is reacted with phosgene ... and in a second step that intermediate is reacted with methylamine to give 1-naphthyl-N-methyl carbamate.
Synthesized directly from 1-naphthol and methyl isocyanate or from naphthyl chloroformate (1-naphthol and phosgene) plus methylamine.
Formulations/Preparations
Aqueous dispersions, baits, dusts, emulsifiable concentrates, flowables, granules, soluble concentrate, suspension concentrate, wettable powder, water based dispersible granules.
Carbaryl is available in the USA in a technical grade of at least 99% purity or a technical grade of 95% purity for use in manufacture of formulations
Carbaryl formulations include ... wettable powders ...
ES CARBARYL INSECTICIDE SPRAY-RTU, CP CARBARYL INSECTICIDE SPRAY - RTU: Active Ingredient 0.126% carbaryl
For more Formulations/Preparations (Complete) data for CARBARYL (36 total), please visit the HSDB record page.
General Manufacturing Information
1-Naphthalenol, 1-(N-methylcarbamate): ACTIVE
The WHO Recommended Classification of Pesticides by Hazard identifies Carbaryl (technical grade) as Class II: moderately hazardous; Main Use: insecticide.
Carbaryl is a carbamate insecticide and molluscide that was first registered in 1959 for use on cotton. Carbaryl has many trade names, but is most commonly known as Sevin.
Compatible with most other pesticides except those strongly alkaline such as bordeaux mixt or lime sulfur, decomp to form alpha-naphthol.
Crude or semirefined coal tar or petroleum naphthalene can be used for carbaryl manufacture.
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