Rotenone is an odorless, colorless,
crystalline
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
isoflavone used as a broad-spectrum
insecticide
Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed t ...
,
piscicide, and
pesticide
Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and ...
. It occurs naturally in the seeds and stems of several plants, such as the
jicama vine plant, and the roots of several members of
. It was the first described member of the family of chemical compounds known as
rotenoids.
Discovery
The earliest record of the now-known rotenone-containing plants used for killing leaf-eating
caterpillars
Caterpillars ( ) are the larval stage of members of the order Lepidoptera (the insect order comprising butterflies and moths).
As with most common names, the application of the word is arbitrary, since the larvae of sawflies (suborder Symp ...
was in 1848, and for centuries, the same plants were used to poison fish.
The active chemical component was first isolated in 1895 by a French botanist,
Emmanuel Geoffroy, who called it ''nicouline'', from a specimen of ''Robinia nicou'', now called ''
Lonchocarpus nicou'', while traveling in
French Guiana
French Guiana ( or ; french: link=no, Guyane ; gcr, label= French Guianese Creole, Lagwiyann ) is an overseas department/region and single territorial collectivity of France on the northern Atlantic coast of South America in the Guianas ...
. He wrote about this research in his thesis, published in 1895 after his death from a
parasitic disease. In 1902
Kazuo Nagai, Japanese chemical engineer of the
Government-General of Taiwan, isolated a pure crystalline compound from ''
Derris elliptica'' which he called rotenone, after the Taiwanese name of the plant 蘆藤 () translated into Japanese . By 1930, nicouline and rotenone were established to be chemically the same.
Uses
Rotenone is used as a pesticide, insecticide, and as a nonselective piscicide (fish killer). Rotenone has historically been used by indigenous peoples to catch fish. Typically, rotenone-containing plants in the legume family,
, are crushed and introduced into a body of water, and as rotenone interferes with cellular respiration, the affected fish rise to the surface in an attempt to gulp air, where they are more easily caught.
In modern times it is frequently used as a tool to remove
alien fish species, as it has a relatively short
half-life
Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable ...
(days) and is gone from rivers in the course of days and from lakes within a few months, depending on (seasonal) stirring,
organic
Organic may refer to:
* Organic, of or relating to an organism, a living entity
* Organic, of or relating to an anatomical organ
Chemistry
* Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...
content, availability of sunlight and temperature.
Rotenone has been used by government agencies to kill fish in rivers and lakes in the United States since 1952, Canada and Norway since 1980s. It is less frequently used in EU countries due to strict regulations, but has seen some use in some selected countries such as the UK (
Topmouth gudgeon), Sweden (
pike and
pumpkinseed
The pumpkinseed (''Lepomis gibbosus''), also referred to as pond perch, common sunfish, punkie, sunfish, sunny, and kivver, is a small/medium-sized North American freshwater fish of the genus ''Lepomis'' (true sunfishes), from family Centrarchi ...
), Spain (
Topmouth gudgeon,
Gambusia) and Hungary (
Prussian carp).
Rotenone decays through metabolites and its final product is reduced to
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...
and
carbondioxyde.
Furthermore, its use is more benign for the environment (as compared to other piscicides) as most species is seen to recolonize aquatic systems within weeks to a year after application. Thus, it has also seen some use in other field studies in the marine environment needing only small quantities. Small-scale sampling with rotenone is used by fish researchers studying the biodiversity of marine fishes to collect cryptic, or hidden, fishes, which represent an important component of shoreline fish communities, since it has only minor and transient environmental side effects.
It is commercialized as ''
cubé'',
''tuba'', or ''derris'', in single preparation or in
synergistic
Synergy is an interaction or cooperation giving rise to a whole that is greater than the simple sum of its parts. The term ''synergy'' comes from the Attic Greek word συνεργία ' from ', , meaning "working together".
History
In Christia ...
combination with other insecticides.
In the United States and Canada, all uses of rotenone except as a piscicide are being phased out. It is currently banned in the United States for any use in organic farming. In the UK, rotenone insecticides (sold under the trade name Derris) were banned for sale in 2009.
Rotenone is also used in powdered form to treat
scabies
Scabies (; also sometimes known as the seven-year itch) is a contagious skin infestation by the mite ''Sarcoptes scabiei''. The most common symptoms are severe itchiness and a pimple-like rash. Occasionally, tiny burrows may appear on the ski ...
and
head lice
The head louse (''Pediculus humanus capitis'') is an obligate ectoparasite of humans. Head lice are wingless insects that spend their entire lives on the human scalp and feeding exclusively on human blood. Humans are the only known hosts of thi ...
on humans, and
parasitic
Parasitism is a close relationship between species, where one organism, the parasite, lives on or inside another organism, the host, causing it some harm, and is adapted structurally to this way of life. The entomologist E. O. Wilson ha ...
mite
Mites are small arachnids (eight-legged arthropods). Mites span two large orders of arachnids, the Acariformes and the Parasitiformes, which were historically grouped together in the subclass Acari, but genetic analysis does not show clear e ...
s on
chickens
The chicken (''Gallus gallus domesticus'') is a domesticated junglefowl species, with attributes of wild species such as the grey and the Ceylon junglefowl that are originally from Southeastern Asia. Rooster or cock is a term for an adult m ...
,
livestock
Livestock are the domesticated animals raised in an agricultural setting to provide labor and produce diversified products for consumption such as meat, eggs, milk, fur, leather, and wool. The term is sometimes used to refer solely to ani ...
, and
pet
A pet, or companion animal, is an animal kept primarily for a person's company or entertainment rather than as a working animal, livestock, or a laboratory animal. Popular pets are often considered to have attractive appearances, intelligence ...
animals.
In agriculture it is also unselective in action and kills
potato beetles,
cucumber beetle
Cucumber beetle is a common name given to members of two genera of beetles, ''Diabrotica'' and ''Acalymma'', both in the family Chrysomelidae. The adults can be found on cucurbits such as cucumbers and a variety of other plants. Many are notor ...
s,
flea beetles,
cabbage worms,
raspberry beetle
The raspberry beetle (''Byturus tomentosus'') is a species of beetle in the fruitworm family Byturidae. It is a major pest that is widespread in north-central Europe, affecting raspberry, blackberry and loganberry plants.
This species is rel ...
s, and
asparagus beetles, as well as most other arthropods. It biodegrades rapidly in soil, with 90% degraded after 1–3 months at and three times faster at .
Mechanism of action
Rotenone works by interfering with the
electron transport chain
An electron transport chain (ETC) is a series of protein complexes and other molecules that transfer electrons from electron donors to electron acceptors via redox reactions (both reduction and oxidation occurring simultaneously) and couples ...
within
complex I in
mitochondria
A mitochondrion (; ) is an organelle found in the cells of most Eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is used ...
, which places it in
IRAC MoA class 21 (by itself in 21B).
It inhibits the transfer of electrons from iron-sulfur centers in
complex I to
ubiquinone. This interferes with
NADH during the creation of usable cellular energy (
ATP).
Complex I is unable to pass off its electron to
CoQ, creating a back-up of electrons within the mitochondrial matrix. Cellular oxygen is reduced to the radical, creating
reactive oxygen species
In chemistry, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (). Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen.
The reduction of molecular oxygen () p ...
, which can damage
DNA and other components of the mitochondria.
Rotenone also inhibits
microtubule
Microtubules are polymers of tubulin that form part of the cytoskeleton and provide structure and shape to eukaryotic cells. Microtubules can be as long as 50 micrometres, as wide as 23 to 27 nm and have an inner diameter between 1 ...
assembly.
Presence in plants
Rotenone is produced by extraction from the roots and stems of several tropical and subtropical plant species, especially those belonging to the genera ''
Lonchocarpus
''Lonchocarpus'' is a plant genus in the legume family ( Fabaceae). The species are called lancepods due to their fruit resembling an ornate lance tip or a few beads on a string.
''Cubé'' resin is produced from the roots of '' L. urucu'' an ...
'' and ''
Derris''.
Some of the plants containing rotenone:
* Hoary pea or goat's rue (''
Tephrosia virginiana'') – North America
* Jícama (''
Pachyrhizus erosus'') – North America
* Cubé plant or lancepod (''
Lonchocarpus utilis'') – South America
** The root extract is referred to as cubé resin
* Barbasco (''
Lonchocarpus urucu'') – South America
** The root extract is referred to as cubé resin
* Tuba plant (''
Derris elliptica'') – southeast Asia and southwest Pacific islands
** The root extract is referred to as derris or derris root
* Jewel vine (''
Derris involuta'') – southeast Asia and southwest Pacific islands
** The root extract is referred to as derris or derris root
* Common Mullein (''
Verbascum thapsus L.)''
* Cork-bush (''
Mundulea sericea'') – southern Africa
* Florida fishpoison tree (''
Piscidia piscipula
''Piscidia piscipula'', commonly named Florida fishpoison tree, Jamaican dogwood, or fishfuddle, is a medium-sized, deciduous, tropical tree in the Fabaceae family. It is native to the Greater Antilles (except Puerto Rico), extreme southern Flori ...
'') – southern Florida, Caribbean
[Nellis, David N. (1994). Seashore plants of South Florida and the Caribbean. Pineapple Press. 160 p.]
* Several species of ''
Millettia
''Millettia'' is a genus of legume in the family Fabaceae. It consists of about 150 species, which are distributed in the tropical and subtropical regions of the world. The genus was formerly known by the name ''Pongamia'', but that name was ...
'' and ''
Tephrosia'' in
South-east Asian regions
Toxicity
Rotenone is classified by the
World Health Organization
The World Health Organization (WHO) is a specialized agency of the United Nations responsible for international public health. The WHO Constitution states its main objective as "the attainment by all peoples of the highest possible level o ...
as moderately hazardous.
It is mildly toxic to
human
Humans (''Homo sapiens'') are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, cultu ...
s and other
mammal
Mammals () are a group of vertebrate animals constituting the class Mammalia (), characterized by the presence of mammary glands which in females produce milk for feeding (nursing) their young, a neocortex (a region of the brain), fur ...
s, but extremely toxic to insects and aquatic life, including fish. This higher toxicity in fish and insects is because the
lipophilic
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipo ...
rotenone is easily taken up through the
gill
A gill () is a respiratory organ that many aquatic organisms use to extract dissolved oxygen from water and to excrete carbon dioxide. The gills of some species, such as hermit crabs, have adapted to allow respiration on land provided they ar ...
s or
trachea
The trachea, also known as the windpipe, is a cartilaginous tube that connects the larynx to the bronchi of the lungs, allowing the passage of air, and so is present in almost all air- breathing animals with lungs. The trachea extends from t ...
, but not as easily through the skin or the
gastrointestinal tract
The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans and ...
. Rotenone is toxic to
erythrocytes
Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...
''
in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology a ...
''.
The lowest lethal dose for a child is 143 mg/kg. Human deaths from rotenone poisoning are rare because its irritating action causes vomiting. Deliberate ingestion of rotenone can be fatal.
The compound
decomposes when exposed to sunlight and usually has an activity of six days in the environment. It oxidizes to rotenolone, which is about an order of magnitude less toxic than rotenone. In water, the rate of decomposition depends upon several factors, including temperature, pH, water hardness and sunlight. The half-life in natural waters ranges from half a day at 24 °C to 3.5 days at 0 °C.
Parkinson's disease
In 2000, injecting rotenone into rats was reported to cause the development of symptoms similar to those of
Parkinson's disease
Parkinson's disease (PD), or simply Parkinson's, is a long-term degenerative disorder of the central nervous system that mainly affects the motor system. The symptoms usually emerge slowly, and as the disease worsens, non-motor symptoms beco ...
(PD). Rotenone was continuously applied over a period of five weeks, mixed with
DMSO and
PEG to enhance tissue penetration, and injected into the
jugular vein
The jugular veins are veins that take deoxygenated blood from the head back to the heart via the superior vena cava. The internal jugular vein descends next to the internal carotid artery and continues posteriorly to the sternocleidomastoid mu ...
. The study does not directly suggest rotenone exposure is responsible for PD in humans, but is consistent with the belief that chronic exposure to environmental toxins increases the likelihood of the disease. In 2011, a US
National Institutes of Health
The National Institutes of Health, commonly referred to as NIH (with each letter pronounced individually), is the primary agency of the United States government responsible for biomedical and public health research. It was founded in the lat ...
study showed a link between rotenone use and Parkinson's disease in farm workers, suggesting a link between neural damage and pulmonary uptake by not using protective gear.
Exposure to the chemical in the field can be avoided by wearing a gas mask with filter, which is standard
HSE procedure in modern application of the chemical.
Studies with primary cultures of rat
neuron
A neuron, neurone, or nerve cell is an electrically excitable cell that communicates with other cells via specialized connections called synapses. The neuron is the main component of nervous tissue in all animals except sponges and placozoa ...
s and
microglia
Microglia are a type of neuroglia (glial cell) located throughout the brain and spinal cord. Microglia account for about 7% of cells found within the brain. As the resident macrophage cells, they act as the first and main form of active immune de ...
have shown low doses of rotenone (below 10 nM) induce oxidative damage and death of
dopaminergic
Dopaminergic means "related to dopamine" (literally, "working on dopamine"), dopamine being a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain. Dopaminergic brain pathways facilitate do ...
neurons
A neuron, neurone, or nerve cell is an electrically excitable cell that communicates with other cells via specialized connections called synapses. The neuron is the main component of nervous tissue in all animals except sponges and placozoa ...
, and it is these neurons in the
substantia nigra
The substantia nigra (SN) is a basal ganglia structure located in the midbrain that plays an important role in reward and movement. ''Substantia nigra'' is Latin for "black substance", reflecting the fact that parts of the substantia nigra ap ...
that die in Parkinson's disease. Another study has also described toxic action of rotenone at low concentrations (5 nM) in dopaminergic neurons from acute rat brain slices. This toxicity was exacerbated by an additional cell stressor – elevated intracellular calcium concentration – adding support to the 'multiple hit hypothesis' of dopaminergic neuron death.
The
neurotoxin
Neurotoxins are toxins that are destructive to nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insultsSpencer 2000 that can adversely affect function in both developing and mature nerv ...
MPTP had been known earlier to cause PD-like symptoms (in humans and other primates, though not in rats) by interfering with complex I in the electron transport chain and killing dopaminergic neurons in the substantia nigra. Further studies involving MPTP have failed to show development of
Lewy bodies, a key component to PD pathology. However at least one study recently has found evidence of protein aggregation of the same chemical makeup as that which makes up Lewy bodies with similar pathology to Parkinson's disease in aged Rhesus monkeys from MPTP. Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood. Because of these developments, rotenone was investigated as a possible Parkinson-causing agent. Both MPTP and rotenone are
lipophilic
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipo ...
and can cross the
blood–brain barrier
The blood–brain barrier (BBB) is a highly selective semipermeable border of endothelial cells that prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of the central nervous system where ne ...
.
In 2010, a study was published detailing the progression of Parkinson's-like symptoms in mice following chronic intragastric ingestion of low doses of rotenone. The concentrations in the central nervous system were below detectable limits, yet still induced PD pathology.
Notable administrations
Rotenone was implemented in 2010 to kill an
invasive goldfish
The goldfish (''Carassius auratus'') is a freshwater fish in the family Cyprinidae of order Cypriniformes. It is commonly kept as a pet in indoor aquariums, and is one of the most popular aquarium fish. Goldfish released into the wild have bec ...
population present in
Mann Lake, with the intention of not disrupting the lake's
trout
Trout are species of freshwater fish belonging to the genera '' Oncorhynchus'', '' Salmo'' and '' Salvelinus'', all of the subfamily Salmoninae of the family Salmonidae. The word ''trout'' is also used as part of the name of some non-salm ...
population. Rotenone successfully achieved these aims, killing nearly 200,000 goldfish, and only three trout.
Beginning May 1, 2006,
Panguitch Lake was treated with rotenone, to potentially eradicate and control the invasive population of
Utah chub
The Utah chub (''Gila atraria'') is a cyprinid fish native to western North America, where it is abundant in the upper Snake River and throughout the Lake Bonneville basin.
This chub generally follows the cyprinid body plan. Its dorsal fin lies ...
, which were probably introduced accidentally by
anglers who used them as
live bait. The lake was restocked with 20,000
rainbow trout
The rainbow trout (''Oncorhynchus mykiss'') is a species of trout native to cold-water tributaries of the Pacific Ocean in Asia and North America. The steelhead (sometimes called "steelhead trout") is an anadromous (sea-run) form of the coast ...
in 2006; as of 2016, the lake's fish population has recovered.
In 2012 rotenone was used to kill all remaining fish in
Stormy Lake (Alaska) due to invasive pike destroying native species, which were re-introduced once the treatment was concluded.
In 2014, rotenone was used to kill all remaining fish in San Francisco's Mountain Lake, which is located in
Mountain Lake Park, in order to rid it of invasive species introduced since the migration of European settlers to the region.
Rotenone is used in biomedical research to study oxygen consumption rate of cells usually in combination with
antimycin A (an electron transport chain Complex III inhibitor),
oligomycin (an ATP synthase inhibitor) and
FCCP (a mitochondrial
uncoupler An uncoupler or uncoupling agent is a molecule that disrupts oxidative phosphorylation in prokaryotes and mitochondria or photophosphorylation in chloroplasts and cyanobacteria by dissociating the reactions of ATP synthesis from the electron transp ...
).
Deactivation
Rotenone can be deactivated in water with the use of
potassium permanganate
Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution.
Potassium permanganate is widely used in the c ...
to lower toxicity back down to acceptable levels.
See also
*
Fenpropathrin
*
NADH dehydrogenase
NADH dehydrogenase is an enzyme that converts nicotinamide adenine dinucleotide (NAD) from its reduced form (NADH) to its oxidized form (NAD+). Members of the NADH dehydrogenase family and analogues are commonly systematically named using the for ...
References
External links
RotenoneCornell University. Rotenone. Resource Guide for Organic and Disease Management.
Rotenone. ARS Pesticide Properties DatabaseRotenone use in research on the biodiversity of marine fishesRotenone registration at US Environmental Protection AgencyRotenone at BioblastChemical Description
{{Rotenoid
Aromatase inhibitors
Rotenoids
Hydroxyquinol ethers
Isoflavones
NADH dehydrogenase inhibitors
Plant toxin insecticides
Respiratory toxins
Microtubule inhibitors
Neurotoxins
Isopropenyl compounds