HuagongsheHuagongshe Chemistry Print Report · For research reference only
Rotenone
Rotenon · (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-iospropenyl-8,9-dimethoxy- · CUBE · gerane · chemfish · Derris root · 5'beta-Rotenone · Pyrethrum powder
Identifiers & Physical Properties
| CAS No. | 83-79-4 |
|---|---|
| Molecular formula | C23H22O6 |
| Average molar mass | 394.4 g/mol |
| Monoisotopic mass | 394.14163842 g/mol |
| SMILES | C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1 |
| InChIKey | JUVIOZPCNVVQFO-HBGVWJBISA-N |
| PubChem CID | 6758 |
| ChEMBL | CHEMBL429023 |
| ChEBI | CHEBI:28201 |
| EC No. | 201-501-9 |
| DTXSID | DTXSID6021248 |
Chemical & Physical Properties
| XLogP | 4.1 |
|---|---|
| Topological polar surface area | 63.2 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 3 |
| Heavy atoms | 29 |
| Formal charge | 0 |
| Complexity | 664 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Lipids | Polyketides [PK] -> Flavonoids [PK12] -> Rotenoid flavonoids [PK1206] |
| Pesticides | Pesticide -> EPA IRISInsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Other InsecticidesVeterinary substances, Acaricides, InsecticidesPesticide (Rotenone) -> USDA PDB |
| LogP (partition coefficient) | log Kow = 4.10 |
| Odor | Odorless |
| Density | 1.27 at 68 °F (NTP, 1992) - Denser than waterwill sink1.27 at 20 °C1.27 g/cm³1.27 @ 20°C1.1917 (rough estimate) |
| Color/Form | Orthorhombic, six-sided plates from trichloroethyleneNeedles or leaves (alcohol, aq acetone)White crystalsColorless to red, crystalline solid |
| Solubility | less than 1 mg/mL at 68 °F (NTP, 1992)SOLUBILITY: 15 PPM IN WATER AT 100 °C. SHOWS RAPID RACEMIZATION ON ALKALI TREATMENTCRYSTALLIZES WITH SOLVENT OF CRYSTALLIZATIONCIS CONFIGURATION IS GENERALLY ACCEPTEDIn water, 15 mg/L at 100 °CSoluble in ethanol, acetone, benzeneslightly soluble in ethervery soluble in chloroformSLIGHTLY SOLUBLE IN PETROLEUM OILSSOL IN LIPIDSinsoluble in EtOHinsoluble in H2O≥77.6 mg/mL in DMSO15 mg l-1 (100 °C) |
| Corrosivity | Non-corrosive |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Boiling point | 410 to 428 °F at 0.5 mmHg (NTP, 1992)BP: 215 °C at 0.5 mm Hg410-428 °FDecomposes210-220 °C/0.5 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Melting point | 159-164 °C (lit.) |
| alpha | -115 º (C=1.4 IN CHLOROFORM) |
| Refractive index | 1.4593 (estimate) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Physical state | White to off-white solid |
| Color | White to Light yellow to Light orange |
| Merck | 14,8271 |
| BRN | 6773081 |
| Henry's law constant | 8.8×107 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies. |
| InChI | 1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 |
| InChIKey | JUVIOZPCNVVQFO-HBGVWJBISA-N |
| SMILES | COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C |
| Toxicology and Carcinogenesis | Toxicology and Carcinogenesis Studies of Rotenone (CASRN 83-79-4) in F344/N Rats and B6C3F1 Mice (Feed Studies) |
| EWG's Food Scores | 1-2 |
| FDA UNII | 03L9OT429T |
| NIST Chemistry Reference | Rotenone(83-79-4) |
| EPA Substance Registry System | Rotenone (83-79-4) |
| Pesticides Freedom of Information Act (FOIA) | Rotenone |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
| GHS pictogram | GHS06,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H300+H330-H315-H319-H335-H410 |
| GHS precautionary statements | P260-P264-P273-P302+P352-P304+P340+P310-P305+P351+P338 |
| Target organs | Respiratory system |
| Hazard symbols | T,N |
| Risk statements (R) | 25-36/37/38-50/53 |
| Safety statements (S) | 22-24/25-36-45-60-61 |
| UN transport number | UN 2811 6.1/PG 3 |
| Occupational exposure band (OEB) | B |
| Occupational exposure limit (OEL) | TWA: 5 mg/m3 |
| Water hazard class (WGK) | 3 |
| RTECS number | DJ2800000 |
| Hazard class | 6.1(b)Acute Tox. 1 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Packing group | III |
| Customs code | 29329990 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Hazardous substances data | 83-79-4(Hazardous Substances Data) |
| Toxicity | LD50 i.p. in mice: 2.8 mg/kg (Fukami)in rats (mg/kg): 132 orally6 i.v. (Soloway) |
| Immediately dangerous to life or health concentration | 2,500 mg/m3 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301 (97.3%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatory information | Rote is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/317Rotenone: HSNO Approval: HSR003076 Approved with controls |
| Other safety information | IMAP assessments - [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2.alpha.,6a.alpha.,12a.alpha.)]-: Environment tier I assessment |
| DOT label | Poison |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Fire potential | Flammable if preheated. |
| Health hazards | Excerpt from NIOSH Pocket Guide for Rotenone: |
| Hazards summary | Formulations for home use are classified as slightly toxic. The emulsified concentrate is classified as highly toxic. Only certified applicators can use rotenone on cranberries and for fish control. [EXTOXNET] Skin and respiratory irritation has been reported after occupational exposure. [EPA Pesticides] Poisoning by ingestion in humans may result in convulsions and coma. [ACGIH] Liver and kidney injury may occur after ingestion. [ICSC] Rotenone is used in an experimental animal model of Parkinson's syndrome, but the large doses used are not likely to be relevant to occupational exposure levels. [Reference #2] Decomposes within days when exposed to light and airNo evidence to support a causal relationship between rotenone and Parkinson's diseaseIn a fatal poisoning case, the estimated oral dose was 50 mg/kg, and the symptoms were coma and respiratory arrest within 8.5 hours of ingestion[Krieger, p. 135-41] |
| Reactive group | Ketones |
| EC classification | Symbol: T, NR: 25-36/37/38-50/53S: (1/2)-22-24/25-36-45-60-61 |
| UN classification | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of Rotenone in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 320 (1988) NIH Publication No. 88-2576USEPA/Office of Pesticide ProgramsReregistration Eligibility Decision Document - Rotenone, EPA 738-R-07-005 (March 2007). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of November 20, 2011: http://www.epa.gov/pesticides/reregistration/status.htm] |
| FIFRA requirements | (a) When applied to growing crops, in accordance with good agricultural practice, the following pesticide chemicals are exempt from the requirement of a tolerance: (1) Petroleum oils. (2) Piperonyl butoxide. (3) Pyrethrins. (4) Rotenone or derris or cube roots. (5) Sabadilla. (b) These pesticides are not exempted from the requirement of a tolerance when applied to a crop at the time of or after harvest.Based on available data, EPA has completed its assessment of the risks associated with the use of pesticides containing the active ingredient rotenone and has concluded that it has sufficient information to make a decision as part of the reregistration process under FIFRA, as amended by the Food Quality Protection Act (FQPA). EPA has determined that currently registered uses of rotenone will not pose unreasonable risks or adverse effects to humans or the environment if the requirements for reregistration outlined in this document are implemented. Unless labeled and used as specified in this document, rotenone would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the requirements for reregistration identified in this document, the Agency may take regulatory action to address the risk concerns from the use of rotenone.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 future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Rotenone is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0255Pesticide type: Insecticide (acaricide,piscicide)Registration Standard Date: 10/88Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): RotenoneData Call-in (DCI) Date(s): 10/13/95AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| First aid measures | Fresh air, rest. Artificial respiration may be needed.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. 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. Rest. Refer for medical attention . |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures) |
| Safe storage | Separated from food and feedstuffs. Well closed. |
| Storage conditions | Store only in original containers, in a dry place inaccessible to children and pets. /7.4% Rotenone Wettable Powder/Containers: Fiber drumstinsmultiwall paper sackskeep in well-ventilated area. |
| Cleanup methods | 1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as a fume hood). Large quantities can be reclaimedhowever, if this is not practical, dissolve in a flammable solvent (such as alc) and atomize in a suitable combustion chamber. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.PESTICIDE DISPOSAL: Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. CONTAINER DISPOSAL: Completely empty bag into application equipment. Then dispose of empty bag in a sanitary landfill or by inCineration, or, if allowed by State and local authorities, by burning, If burned, stay out of smoke. /7.4% Rotenone Wettable Powder/SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.1. By making packages of rotenone in paper or other flammable material and burning in a suitable combustion chamber. 2. By dissolving rotenone in a flammable solvent (such as alcohol) and atomizing in a suitable combustion chamber. |
| Spillage disposal | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered air-tight containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: 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.Wear protective gloves adn clothing to prevent any reasonable probability of skin contact. ... Wear dust proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. ...The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet or significantly contaminated should be removed and replaced.For more Preventive Measures (Complete) data for ROTENONE (6 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection if powder. |
| Treatment | Since rotenone is unstable in light and heat, its toxicity can be lost after 2 or 3 days. (T10) |
| Target organs | DevelopmentalEyes, skin, respiratory system, central nervous systemRespiratory system |
| Health effects | Studies with primary cultures of rat neurons and microglia have shown low doses of rotenone (below 10 nM) to induce oxidative damage and death of dopaminergic neurons and it is these neurons in the substantia nigra that die in Parkinson's disease. Injecting rotenone into rats causes symptoms of Parkinson's disease to develop. The study does not directly suggest that rotenone exposure is responsible for Parkinson's disease in humans. (L1274) Rotenone dust is highly irritating to the eyes (causing conjunctivitis), skin (causing contact dermatitis), upper respiratory tract (causing rhinitis), and throat (linked with pharyngitis) (T10) |
| Ecotoxicity values | LD50Species: Anas platyrhynchos (Mallard duck) female, 3 months oldoral > or =2200 mg/kgLC50Species: Anas platyrhynchos (Mallard) 10 days oldoral approx 2600 ppmSpecies: Coturnix japonica (Japanese quail) juvenile 14 days posthatchoral diet 5,608 ppm (95% confidence interval 4459-7053 ppm) for 5 day, slope: 5.78, standard error: 1.57Species: Phasianus colchicus (Pheasant) female, 3 months oldoral 1680 mg/kg (95% confidence limit: 1410-2000 mg/kg)For more Ecotoxicity Values (Complete) data for ROTENONE (133 total), please visit the HSDB record page. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,200(SRC), determined from a log Kow of 4.10(2), and a regression-derived equation(3), indicates that rotenone is expected to have slight mobility in soil(SRC). Volatilization of rotenone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.12X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Rotenone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.9X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). The field half-life for rotenone in anaerobic and aerobic soils is 3 days(5). Half-life values reported from experiments of rotenone degradation in Italian soils ranged from 21-25 days at 10 °C and 5-8 days at 20 °C(6), suggesting that biodegradation may be in important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,200(SRC), determined from a log Kow of 4.10(2), indicates that rotenone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.12X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF range of 125 to 3500(6) suggests that bioconcentration in aquatic organisms is high to very high(SRC). In freshwater mussels and crayfish, rotenone residues gradually increased for 1 week in cold water and 1 day in warm water and then slowly decreased. Rotenone residues in fish varied with species and water temperatures(7). Decomposition of rotenone in water followed a first-order decay curvethe half-life was 10.3 days in cold water and 0.94 days in warm water(7). A photolysis study showed that rotenone degraded by first order kinetics in near UV light and indicated estimated summer time photolysis half-life was as 191 days for a well-mixed pond with a depth of 2 m, and 21 hours for a stratified pond in which rotenone remains in the top 1 cm surface layer(8). Rotenone may be degraded during aerobic and anaerobic sewage treatment if adequate acclimatization can be achieved(9), suggesting that biodegradation in water is conditional(SRC).AQUATIC FATE: A cold water pond (0 to 5 °C, November 1983) at the Geona National Fish Hatchery, Wisconsin and a warm water pond (23 to 27 °C, July 1984) at the La Crosse National Fisheries Research Center was treated with Noxfish (0.25 mg/L rotenone) and analyzed. In the cold water pond, the mean concentration of rotenone in samples taken 3 hours after treatment was 0.229 mg/Lconcentration of rotenone declined gradually but steadily to 0.002 mg/L (limit of detection) after 57 days. In the warm water pond the mean concentration of rotenone in samples taken after 3 hours was 0.180 mg/Lconcentration of rotenone declined by more than 50 percent in the first 12 hours and then fell to 0.002 mg/L within four days(1). Residues of rotenone in bottom sediments in the cold water pond peaked at 0.10 ug/g after 14 days and then declined to <0.025 ug/g (limit of detection) after 64 days. Accumulation and elimination were much faster in the warm water pond: concentration in bottom sediments peaked at 0.075 ug/g after 6 hours and dropped to <0.025 ug/g after 24 hours(1).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), rotenone, which has an estimated vapor pressure of 6.9X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase rotenone may be removed from the air by wet or dry deposition(SRC). Rotenone contains chromophores that absorb at wavelengths >290 nm(4), and therefore is expected to be susceptible to direct photolysis by sunlight(SRC). When exposed to light and air, rotenone undergoes hydroxylation at C-7, followed by dehydration to form dehydrorotenone. These reactions inactivate rotenone after 5 to 10 days of exposure to sunlight(5). |
| Food survey values | Pesticide residues were reported in foods for the 4-year period 1982 to 1986. Rotenone was found as a residue in FY83-86 regulatory monitoring of approximately 11,500 samples(1). |
| Adverse effects | Neurotoxin - Parkinsonism |
| Exposure routes | The substance can be absorbed into the body by inhalation and by ingestion.inhalation, ingestion, skin and/or eye contact |
| Toxicity summary | Rotenone works by interfering with the electron transport chain in mitochondria. Specifically, it inhibits the transfer of electrons from iron-sulfur centers in complex I to ubiquinone. This prevents NADH from being converted into usable cellular energy (ATP). (L1274) |
| Ecotoxicity excerpts | /BIRDS and MAMMALS/ Signs of intoxication: ataxia, nutation/act of nodding especially involuntary nodding/, dyspnea, polyuria, feathers fluffed or held tightly to body, wing drop, neck pulled in, immobility. Regurgitation occurred at levels above 1500 mg/kg. Signs were observed less than an hour after single oral administration, and mortalities occurred up to 5 days after treatment. Remission took up to 1 week. /Mallards and/or Pheasants//AQUATIC SPECIES/ Rotenone, a natural insecticide and piscicide, was shown to have an extremely small margin between no lethality (5.0 ug/L) and 100% mortality (6.6 ug/L) for static-renewal 96-hour toxicity tests with juvenile rainbow trout (Oncorhynchus mykiss). Dissolved organic carbon (DOC) at concentrations of 3.0 and 4.0 mg/L significantly increased the rotenone 96-hour LC(50) (median lethal concentration) from 5.80 ug/L (confidence interval (CI) 5.51 to 6.10) to 6.55 ug/L (CI 6.28 to 6.83) and 7.75 ug/L (CI 7.29 to 8.24), respectively, probably as a result of rotenone adsorption onto DOC, which decreased its bioavailability. Using concentrations of 0, 3.0, 4.0, and 5.0 ug/L rotenone and exposure periods of 2, 4, 6, 12, 16, 24, and 48 hours, the threshold concentration of rotenone for impairment of critical swimming performance (Ucrit) was 3.0 ug/L (P = 0.029), with no further impairment at higher concentrations and no time-dependent effect on Ucrit. Using continuous measures of oxygen uptake for 48 hours before and 48 hours during rotenone exposure (0, 1.5, 2.5, 3.0, and 3.5 ug/L), rotenone significantly decreased peak active oxygen uptake at all rotenone concentrations tested without affecting routine oxygen uptake. Fish were individually chased and then placed in rotenone concentrations of 0, 1.0, 3.0, 4.0, 5.0, and 6.0 ug/L to monitor initial postexercise oxygen uptake (Mo2Max) and excess postexercise oxygen consumption (EPOC) during a 40-minute recovery period. Rotenone significantly decreased Mo2Max (P = 0.002) after exposures to 4.0 and 5.0 ug/L, but not 6.0 ug/L, without affecting EPOC./AQUATIC SPECIES/ (Artemia) nauplii was used to asses the toxicity of rotenone, MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), MP+ (1-methyl-4-phenylpyridinium) and the effect of L-DOPA co-treatment with rotenone. Rotenone had a dose dependent effect on mortality (LC50: 0.37 +/- 0.04 uM mean +/- S E, n = 24), while MPTP and MP+ proved to be toxic in millimolar range (LC50: 0.21 +/- 0.09 mM and 0.20 +/- 0.08 mM, respectively, n = 4). L-DOPA (50-200 uM) co-treatment increased the survival of the rotenone-treated animals (LC50: 0.51 +/- 0.23 uM, 1.03 +/- 0.66 ?M, and 0.76 +/- 0.52 ?M, respectively). In the whole body tissue homogenates of Artemia, sublethal (up to 0.3 uM) concentrations of rotenone increased the glutathione S-transferase (GST) activity by up to 50 about percent (LC50: 53.3 +/- 6.8 nM/min/mg protein, against 34.7 +/- 3.6 nM/min/mg protein, n = 4). Nauplii treated in 100 mM L-DOPA and rotenone together showed further increase of GST activity all across the range of rotenone concentrations. These results on Artemia nauplii show similarities with other animal models, when complex I inhibitors were tested. Biochemical measurements suggest a protective role of L-DOPA by increasing the GST activity as part of the intracellular defences during toxin-evoked oxidative stress./OTHER TERRESTRIAL SPECIES/ A 90% mortality of the 4th instar larvae of Aedes aegypti occurred after exposure for 24 hr to 1 day-aged rotenone (4 ppm) extracted from Derris elliptica roots. The mortality percentage was dose-dependent and decreased by aging rotenone extracts. The toxicity of rotenone to mosquitoes was completely lost within 14-15 days after extraction. The content of rotenone in roots was higher (2.27%) in winter than in summer (1.6%)./FIELD STUDIES/ Applications of 2 or 5 uL/L concentration of synergized rotenone (2.5%) in the Pro-Noxfish formulation to 2 shallow, 0.05 hectare ponds caused a temporary reduction in both total number and diversity of benthic invertebrates, a total mortality of caged Asiatic clams (Corbicula manilensis) in both ponds, and a partial mortality of a resident population of larval leopard frogs (Rana pipiens) in the 5 uL/L treatment. At day 7 after treatment, benthic organisms were reduced 67% by the 2 uL/L concentration and 96% by the 5 uL/L application. The diversity index declined sharply in both ponds between days 3 and 7 after treatment, the lowest values being recorded on day 7 and day 37 in the 2 and 5 uL/L treatments, respectively. The equitability index declined from day 3 to day 37 in both ponds. By day 69, however, total numbers of benthic organisms had more than doubled over those originally present in the 2 uL/L treatment, had more than tripled in the 5 uL/L treatment, and were virtually unchanged in the control pond. Pretreatment zooplankton populations were lowno significant deleterious effects from the treatments were observed. |
| Signs and Symptoms | Confusion. Cough. Headache. Tremor. Laboured breathing. Nausea. Sore throat. Unconsciousness.Redness.Abdominal cramps. Convulsions. Diarrhoea. Vomiting. Further see Inhalation.irritation eyes, skin, respiratory systemnumb mucous membranenausea, vomiting, abdominal painmuscle tremor, incoordination, clonic convulsions, stuporAcute poisoning in animals is characterized by an initial respiratory stimulation followed by respiratory depression, ataxia, convulsions, and death from respiratory arrest. (T10) |
| Acute Toxicity Link | Chemical: ROTENONE |
| State drinking water guidelines | (ME) MAINE 28 ug/l(FL) FLORIDA 28 ug/l |
| Occupational exposure band (OEB) | B |
| Occupational exposure limit (OEL) | TWA: 5 mg/m3 |
| Water hazard class (WGK) | 3 |
| Immediately dangerous to life or health concentration | 2,500 mg/m3 |
| RTECS number | DJ2800000 |
| UN transport number | UN 2811 6.1/PG 3 |
| Customs code | 29329990 |
| Toxicity | LD50 i.p. in mice: 2.8 mg/kg (Fukami)in rats (mg/kg): 132 orally6 i.v. (Soloway) |
| Risk statements (R) | 25-36/37/38-50/53 |
| Signal word | Danger |
| GHS pictogram | GHS06,GHS09 |
| Hazard symbols | T,N |
| Safety statements (S) | 22-24/25-36-45-60-61 |
| Hazard class | 6.1(b)Acute Tox. 1 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | III |
| GHS hazard statements | H300+H330-H315-H319-H335-H410 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| GHS precautionary statements | P260-P264-P273-P302+P352-P304+P340+P310-P305+P351+P338 |
| Hazardous substances data | 83-79-4(Hazardous Substances Data) |
Applications & Uses
Description
The principal source of rotenone is the tuber root of Derris elliptica; however, it is also extracted from the roots of Derris mallaccensis, Lonchocarpus utilis, and Lonchocarpus uruca. Rotenone is both a stomach and contact poison for arthropods. Its fast knockdown action is attributed to decreasing the availability of nicotinamide adenine dinucleotide to serve as a cofactor in various biochemical pathways including the Krebs cycle, thereby inhibiting the mitochondrial respiratory enzymes.
Description
Rotenone is a classical inhibitor of complex I of the mitochondrial electron transport chain, inhibiting NADH/DB oxidoreductase and NADH oxidase with IC50 values of 28.8 and 5.1 nM, respectively. In substantia nigra pars compacta neurons, it activates ATP-sensitive potassium channels and increases the production of reactive oxygen species (ROS) in the mitochondria, effects that are decreased by the antioxidant trolox . In rodents, rotenone induces dopaminergic cell death in the substantia nigra, formation of cytoplasmic inclusions similar to Lewy bodies, oxidative damage to proteins, and parkinsonian symptoms of bradykinesia and rigidity. In a rat model of Parkinson’s disease, chronic rotenone administration of 1.5 and 2.5 mg/kg per day for two months reduces tyrosine hydroxylase levels in the posterior striatum and prefrontal cortex, induces catalepsy, and decreases spontaneous locomotion and exploration in the open field test. Formulations containing rotenone have been used as insecticides and piscicides.
Uses
Insecticide; lotion for chiggers; emulsion for scabies.
Uses
Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants. Rotenone was first registered in 1947 and is currently used exclusively to kill fish (U.S. EPA, 2007). In 2006, registrants voluntarily canceled all livestock, residential and home owner uses, domestic pet uses, and all other uses except for piscicide uses. Currently the main uses include fish management strategies to remove nonnative fish species from lakes, ponds, or streams and in catfish aquaculture prior to stocking ponds with with fry to remove undesirable fish species (U.S. EPA, 2006d). Rotenone has been historically used by native people to paralyze fish for capture and consumption. Outside the United States, the compound is still used to control insects in fruit and vegetable cultivation and for control of fire ants and mosquito larvae in pond water (HSDB, 2012a).
Uses
Rotenone is used for the control of aphids, thrips, suckers and other insects in fruit and vegetable cultivation. It is also used for control in buildings, for the control of lice, ticks and warble fly on animals and as a piscicide for the management of fish populations.
General Description
Colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste.