Rotenone Chemical Properties
- Melting point:159-164 °C (lit.)
- Boiling point:210-220 °C/0.5 mmHg (lit.)
- alpha -115 º (C=1.4 IN CHLOROFORM)
- Density 1.1917 (rough estimate)
- refractive index 1.4593 (estimate)
- storage temp. Keep in dark place,Inert atmosphere,Room temperature
- Water Solubility 15 mg l-1 (100 °C)
- form White to off-white solid
- Merck 14,8271
- BRN 6773081
- Stability:Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.
- NIST Chemistry ReferenceRotenone(83-79-4)
- EPA Substance Registry SystemRotenone (83-79-4)
- Hazard Codes T,N
- Risk Statements 25-36/37/38-50/53
- Safety Statements 22-24/25-36-45-60-61
- RIDADR UN 2811 6.1/PG 3
- WGK Germany 3
- RTECS DJ2800000
- HazardClass 6.1(b)
- PackingGroup III
- HS Code 29329990
- Hazardous Substances Data83-79-4(Hazardous Substances Data)
- ToxicityLD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway)
Rotenone Usage And Synthesis
- DescriptionThe 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.
- Chemical PropertiesRotenone is a colorless to red odorless crystalline solid; a white crystalline solid when pure; oxidation will cause yellowing to bright red coloring. Odorless.
Rotenone is related to isoflavonoid compounds derived from the roots of Derris spp., Lonchocarpus spp., and Tephrosia spp., found primarily in Southeast Asia, South America, and East Africa. The isolated compound is an odorless, colorless to red crystalline solid. It is insoluble in water and has a very low vapor pressure (U.S. EPA, 2007; HSDB, 2012a).
- UsesRotenone 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.
- UsesRotenone 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).
- UsesInsecticide; lotion for chiggers; emulsion for scabies.
- DefinitionChEBI: A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy group (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).
- General DescriptionColorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste.
- Air & Water ReactionsROTENONE decomposes upon exposure to light or air. Insoluble in water.
- Reactivity ProfileROTENONE is readily oxidized in the presence of alkalis. ROTENONE is incompatible with oxidizers. .
- Hazard Toxic by ingestion, overexposure can be fatal, irritant to skin, eyes and upper respiratory tract. Central nervous system impairment. Ques- tionable carcinogen.
- Health HazardRotenone is an irritant and affects the nervous system, causing convulsions.
- Fire HazardFlash point data for ROTENONE are not available; however, ROTENONE is probably combustible.
- Agricultural UsesInsecticide, Acaracide, Veterinary medicine: The use of rotenone as a pesticide to kill invasive fish species is currently the only allowable use of this pesticide. Rotenone is a selective, nonspecific botanical insecticide with some acaricidal properties, and has been used in agriculture to control insects on vine fruit, flowers and vegetables. Registered for use in the U.S.A U.S. EPA restricted Use Pesticide (RUP) due to acute inhalation, acute oral, and aquatic toxicity. Agricultural and residential uses and all food uses were voluntarily cancelled in 2006. In 2006, registrants requested voluntarily cancellation of all livestock, residential and home owner uses, domestic pet uses, and all other uses except for pesticide uses. In 2011 the use of this pesticide chemical was linked to Parkinson’s disease. Not listed for use in EU countries.
- Trade nameACME® Rotenone; AROL GORDON DUST®; BARBASCO®; BONIDE CUKE AND MELON DUST®; CENOL GARDEN DUST®; CHEM FISH®; CHEM-MITE®; CUBE®; CUBE EXTRACT®; CUBEPULVER®; CUBEROL®; CUBE ROOT®; CUBOR®; CUREX FLEA DUSTER®; DACTINOL®; DERIL®; DERRIN®; DERRIS®; DRI-KIL®; ENT-133®; EXTRAX®; FISH-TOX®; GREEN CROSS WARBLE POWDER®; HAIARI®; LIQUID DERRIS®; MEXIDE®; NICOULINE®; NOXFIRE®; NOXFISH®; PARADERIL®; POWDER AND ROOT®; PRENTOX®; PRO-NOX FISH®; RO-KO®; RONONE®; ROTACIDE®; ROTEFIVE®; ROTEFOUR®; ROTESSENOL®; SINID®; TOX-R®; TUBATOXIN®
- Biological ActivityMitochondrial electron transport chain inhibitor (IC 50 = 1.7 - 2.2 μ M at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC 50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. Cell-permeable and brain penetrant.
- Potential ExposureA potential danger to those involved in extraction from derris root, formulation or application of this insecticide. Rotenone is used as a pharmaceutical and veterinary drug.
- CarcinogenicityIn human lymphocyte culture assays rotenone did not increase the frequency of chromosomal aberrations or sister chromatid exchanges but did cause an increase in the frequency of binucleated micronuclei and a delay in cell cycle.
- Environmental FateRotenone released to the atmosphere will exist as particulates due to the extremely low vapor pressure. Particulate-phase rotenone will be removed from the atmosphere by wet and dry deposition and may be degraded by direct photolysis. It is mobile to moderately mobile in soil and sediment and volatilization from soil surfaces is not expected to occur to any extent. If released to water, rotenone generally degrades quickly through abiotic (hydrolytic and photolytic) mechanisms, with half-lives of a few days to several weeks or longer depending on water temperature (U.S. EPA, 2007; HSDB, 2012a).
Rotenone has a relatively low potential for bioconcentration in aquatic organisms (Bioconcentration Factor (BCF) < 30X) (U.S. EPA, 2007).
- Metabolic pathwayBy hepatic microsomal incubations from rainbow trout with 14C-rotenone, three major and several minor metabolites of rotenone are observed, the major ones being identified as rotenolone and two epimeric forms of 6' ,7' -dihydroxyrotenone.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
- DegradationRotenone is racemised in base to less insecticidal compounds and it is decomposed on exposure to light and air (PM). Photochemical degradation in methanol of seven rotenoids isolated from Tephrosa villosa (Krupadanam et al., 1978) resulted generally in much decomposition but rotenone was relatively stable under the conditions used. When the compound was used as an insecticidal spray it was converted by light and air into dehydro-rotenone (2) and rotenonone (3). These structures are shown in Scheme 1.
- Toxicity evaluationRotenone inhibits the electron transport chain by blocking
transport between the flavoprotein and the ubiquinone. The
oxidation of pyruvate in rat mitochondria is virtually
completely blocked by rotenone in vitro (<1 mmol l-1 concentration). Cell death occurs by apoptosis due to excess
generation of free radicals. In addition, rotenone causes a definite
anesthetic effect when it comes in contact with nerve
axons. Death appears to occur due to depression of the respiratory
Rotenone is toxic to insects, humans, animals, and fish. Rotenone exerts selective toxicity, as it is highly toxic to fish because of its rapid absorption from the GI tract in comparison to mammalian species in which it is poorly absorbed. The selective toxicity of rotenone in insects and fish versus mammals can also be explained based on the metabolism of this compound. Rotenone converts to highly toxic metabolites in large quantities in insects and fish, while it converts to nontoxic metabolites in mammals.
- IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and alkalies.
- Waste DisposalRotenone is decomposed by light and alkali to less insecticidal products. It is readily detoxified by the action of light and air. It is also detoxified by heating; 2 hours @ 100 ? C results in 76% decomposition. Oxidation products are probably nontoxic. Incineration has been recommended as a disposal procedure. Burial with lime would also present minimal danger to the environ- ment . In accordance with 40CFR165, follow recommen- dations for the disposal of pesticides and pesticide containers. Must be disposed properly by following pack- age label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Rotenone Preparation Products And Raw materials
- delsoline (6R,7S,8S)-5,6,7,8-Tetrahydro-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-2-naphthalenol Toosendanin NA Pyridaben DEGUELIN Rotenone ROTENONE SOLUTION 1000UG/ML IN METHYLENE CHLORIDE 1ML Abamectin+Rotenone,E.C. ROTENONE UN2811III ROTENONE SOLUTION 3200UG/ML IN METHANOL:ACETONITRILE (50:50) POR ROTENONE SOLUTION 1000UG/ML IN METHYLENE CHLORIDE 5X1ML ROTENONE SOLUTION 100UG/ML IN ACETONITRILE 1ML ROTENONE SOLUTION 1000UG/ML IN METHYLENE CHLORIDE 5ML TIMTEC-BB SBB006465 11-HYDROXYROTENONE AKOS NCG1-0077 amorphin
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