Names | |
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IUPAC name (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate | |
Other names Sumithrin; Phenothrine; Phenoxythrin; Sumitrin; Wellcide; Pibutin; Anvil; Duet; Anchimanaito 20S | |
Identifiers | |
3D model (JSmol) | |
2160930 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.043.079 |
EC Number |
|
KEGG | |
MeSH | Phenothrin |
PubChem CID | |
UNII | |
UN number | 3082 2902 |
CompTox Dashboard (EPA) | |
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Properties | |
C23H26O3 | |
Molar mass | 350.451 g/mol |
Melting point | <25 °C |
Boiling point | >290 °C |
Pharmacology | |
P03AC03 ( WHO ) QP53AC03 ( WHO ) | |
Hazards [1] | |
GHS labelling: | |
Warning | |
H302, H312, H332, H410 | |
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Phenothrin, also called sumithrin and d-phenothrin, [2] is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. It is often used with methoprene, an insect growth regulator that interrupts the insect's biological lifecycle by killing the eggs.
Phenothrin is primarily used to kill fleas and ticks. [3] It is also used to kill head lice in humans, but studies conducted in Paris and the United Kingdom have shown widespread resistance to phenothrin. [3]
It is extremely toxic to bees. A U.S. Environmental Protection Agency (EPA) study found that 0.07 micrograms were enough to kill honey bees. [3] It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 ppb killing mysid shrimp. [3] It has increased risk of liver cancer in rats and mice in long-term exposure, with doses in the range of 100 milligrams per kilogram of body weight per day, or above. [3] It is capable of killing mosquitoes, [4] although remains poisonous to cats and dogs, with seizures and deaths being reported due to poisoning. [3] Specific data on concentrations or exposure are lacking.
Phenothrin has been found to possess antiandrogen properties, and was responsible for a small epidemic of gynecomastia via isolated environmental exposure. [5] [6]
The EPA has not assessed its effect on cancer in humans. However, one study performed by the Mount Sinai School of Medicine linked sumithrin with breast cancer; the link made by its effect on increasing the expression of a gene responsible for mammary tissue proliferation. [3]
In 2005, the U.S. EPA cancelled permission to use phenothrin in several flea and tick products, at the request of the manufacturer, Hartz Mountain Industries. [7] [8] The products were linked to a range of adverse reactions, including hair loss, salivation, tremors, and numerous deaths in cats and kittens. In the short term, the agreement called for new warning labels on the products.
As of March 31, 2006, the sale and distribution of Hartz's phenothrin-containing flea and tick products for cats has been terminated. However, EPA's product cancellation order did not apply to Hartz flea and tick products for dogs, and Hartz continues to produce many of its flea and tick products for dogs. [9]
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 to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.
Raid is the brand name of a line of insecticide products produced by S. C. Johnson & Son, first launched in 1956.
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 included in the genus Pyrethrum. Pyrethrum is also the name of a natural insecticide made from the dried flower heads of Chrysanthemum cinerariifolium and Chrysanthemum coccineum. The insecticidal compounds present in these species are pyrethrins.
Piperonyl butoxide (PBO) is a pale yellow to light brown liquid organic compound used as a synergist component of pesticide formulations. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole.
The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.
Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.
A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.
Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto clothing or mosquito nets to kill the insects that touch them.
An insect repellent is a substance applied to skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and ticks (arachnids).
The allethrins are a group of related synthetic compounds used in insecticides. They are classified as pyrethroids, i.e. synthetic versions of pyrethrin, a chemical with insecticidal properties found naturally in Chrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.
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 deltamethrin has seen a widespread increase.
Methoprene is a juvenile hormone (JH) analog which acts as a growth regulator when used as an insecticide. It is an amber-colored liquid with a faint fruity odor.
Resmethrin is a pyrethroid insecticide with many uses, including control of the adult mosquito population.
Cyhalothrin is the ISO 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 structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
A fogger is any device that creates a fog, typically containing an insecticide for killing insects and other arthropods. Foggers are often used by consumers as a low cost alternative to professional pest control services. The number of foggers needed for pest control depends on the size of the space to be treated, as stated for safety reasons on the instructions supplied with the devices. The fog may contain flammable gases, leading to a danger of explosion if a fogger is used in a building with a pilot light or other naked flame.
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, it is highly toxic to fish and invertebrates, but it is far less toxic to humans. It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.
Dinotefuran is an insecticide of the neonicotinoid class developed by Mitsui Chemicals for control of insect pests such as aphids, whiteflies, thrips, leafhoppers, leafminers, sawflies, mole cricket, white grubs, lacebugs, billbugs, beetles, mealybugs, and cockroaches on leafy vegetables, in residential and commercial buildings, and for professional turf management. Its mechanism of action involves disruption of the insect's nervous system by inhibiting nicotinic acetylcholine receptors. In order to avoid harming beneficial insects such as bees, it should not be applied during bloom.
Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.
Flea treatments are procedures used to treat flea infestations in human or animal populations. They may treat both the itching caused by bites and may remove or kill the fleas themselves.
Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.
Reinforcing the evidence suggesting that there is a relationship between chemicals and GM, it is worthwhile mentioning the epidemic onset observed among Haitian refugees in 1981 about four months after arrival in United States detention centers.22 After analyzing all identifiable environmental exposures, it was then found that phenothrin, a multi-insecticide contained in sprays that they had used was the causative agent.23 It is now widely known that phenothrin has antiandrogenic activity.