Fenpropathrin
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Fenpropathrin, or fenopropathrin, is a widely used
pyrethroid A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. I ...
insecticide in
agriculture Agriculture or farming is the practice of cultivating plants and livestock. Agriculture was the key development in the rise of sedentary human civilization, whereby farming of domesticated species created food surpluses that enabled people t ...
and household. Fenpropathrin is an ingestion and contact synthetic pyrethroid. Its mode of action is similar to other natural (
pyrethrum ''Pyrethrum'' was a genus of several Old World plants now classified as ''Chrysanthemum'' or ''Tanacetum'' which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly inclu ...
) and synthetic pyrethroids where in they interfere with the kinetics of voltage gated sodium channels causing paralysis and death of the pest. Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980. Like other pyrethroids with an α-cyano group, fenpropathrin also belongs to the termed type II
pyrethroids A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. In ...
(e.g.
cyfluthrin Cyfluthrin is a pyrethroid insecticide and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of isomers. Like most pyrethroids (MoA 3a), it is highly toxic to fish and invertebrates, but ...
,
cyhalothrin Cyhalothrin is the International Organization for Standardization, ISO trivial name, common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the ...
,
cypermethrin Cypermethrin (CP) is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degrad ...
,
deltamethrin Deltamethrin is a pyrethroid ester insecticide. Deltamethrin plays a key role in controlling malaria vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets; however, resistance of mosquitos and bed bugs to deltamethri ...
and
esfenvalerate Esfenvalerate is a synthetic pyrethroid insecticide marketed under the brand Asana. It is the (''S'')-enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(en ...
). Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves. Application rates of fenpropathrin in agriculture according to US environmental protection agency (EPA) varies by crop but is not to exceed 0.4 lb a
acre


Toxicity

A person developed
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 becom ...
after six months of daily exposure to fenpropathrin, and animal tests subsequently revealed that the compound is a dopaminergic neurotoxin. The patient had a history of eating fenpropathrin-poisoned fish for 6 months. The follow up Dopaminergic degeneration study was conducted using mice treated with fenpropathrin at 15mg/kg/day for 60 days. It has thus been implicated as an environmental risk factor for Parkinson's disease similar to
organochlorines An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...
, organophosphates and
pyrethroids A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. In ...
especially at higher doses. An acute reference dose for chronic dietary exposure for fenpropathrin is set at 0.025/mg/kg/day by U
EPA
Fenpropathrin is toxic to bees if they come in contact with them directly similar to other
insecticides 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 ...
. Toxicity dissipates with time when deposited o
foliage
and is <2
hours


Environmental Fate

Fenpropathrin degrades from soil by two main mechanisms, biodegradation and photochemical degradation of surface deposits. The time of degradation depends on the characteristics of the soils. The half-life of disappearance for fenpropathrin in soils was 11 to 17 days under aerobic conditions and approx >1 yr under anaerobic conditions. The half-life of fenpropathrin on the surface of a sterilized sandy loam was in the range of 3 to 4 days following irradiation with natura
sunlight


Trade Names

Danitol, Meothrin, Tame.


See also

* 6-Hydroxydopamine *
MPTP MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) is a prodrug to the neurotoxin MPP+, which causes permanent symptoms of Parkinson's disease by destroying dopaminergic neurons in the substantia nigra of the brain. It has been used to study d ...
*
Norsalsolinol Norsalsolinol is a chemical compound that is produced naturally in the body through metabolism of dopamine. It has been shown to be a selective dopaminergic neurotoxin, and has been suggested as a possible cause of neurodegenerative conditions suc ...
*
Rotenone Rotenone is an odorless, colorless, crystalline isoflavone used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the seeds and stems of several plants, such as the jicama vine plant, and the roots of several mem ...


References

Neurotoxins (cyano-(3-phenoxyphenyl)methyl) 2,2,3-trimethylcyclopropane-1-carboxylates {{antiinfective-drug-stub