Methoprene

Last updated
Methoprene [1]
Methoprene.png
Methoprene-3D-balls.png
Names
Preferred IUPAC name
Propan-2-yl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
Other names
Methoprene, Altosid, Apex, Diacan, Dianex, Kabat, Minex, Pharorid, Precor, ZR-515
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.049.977 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH C093000
PubChem CID
UNII
  • InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+ X mark.svgN
    Key: NFGXHKASABOEEW-LDRANXPESA-N X mark.svgN
  • InChI=1/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+
    Key: NFGXHKASABOEEW-LDRANXPEBN
  • CC(C)(OC)CCCC(C)C/C=C/C(C)=C/C(OC(C)C)=O
Properties
C19H34O3
Molar mass 310.48 g/mol
AppearanceLiquid
Boiling point 100 °C (212 °F; 373 K) at 0.05 mmHg
Pharmacology
QP53AX28 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Eye irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Methoprene does not kill insects. Instead, it interferes with an insect’s life cycle and prevents it from reaching maturity or reproducing. [2] Juvenile growth hormones must be absent for a pupa to molt to an adult, so methoprene-treated larvae will be unable to successfully change from pupae to adults. This breaks the biological life cycle of the insect, preventing recurring infestation.

Methoprene is considered a biological pesticide because rather than controlling target pests through direct toxicity, methoprene interferes with an insect’s lifecycle and prevents it from reaching maturity or reproducing. [3]

Applications

Methoprene is used in the production of a number of foods, including meat, milk, mushrooms, peanuts, rice, and cereals. It also has several uses on domestic animals (pets) for controlling fleas.

It is used in drinking water cisterns to control mosquitoes which spread dengue fever and malaria. [4] Methoprene is commonly used as a mosquito larvicide used to help stop the spread of the West Nile virus.

Methoprene is also used as a food additive in cattle feed to prevent fly breeding in the manure.

Health and safety

According to the Safety Data Sheet (SDS), methoprene is a material that may be irritating to the mucous membranes and upper respiratory tract, may be harmful by inhalation, ingestion, or skin absorption, may cause eye, skin, or respiratory system irritation and is very toxic to aquatic life. [5] The GHS signal word is "Warning," with notes such as P273 Avoid release into the environment and P391 collect spillage.

Methoprene is suspected to be highly toxic to lobsters. Like insects and mites, lobsters are arthropods. [6]

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. The major use of Insecticides is agriculture, but they are also used in home and garden, industrial buildings, vector control and control of insect parasites of animals and humans. 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.

<span class="mw-page-title-main">Piperonyl butoxide</span> Chemical compound

Piperonyl butoxide (PBO) is a pale yellow to light brown liquid organic compound used as an adjuvant component of pesticide formulations for synergy. 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 and is produced from the condensation of the sodium salt of 2-(2-butoxyethoxy) ethanol and the chloromethyl derivative of hydrogenated safrole (dihydrosafrole); or through 1,2-Methylenedioxybenzene.

<span class="mw-page-title-main">DEET</span> Chemical compound

N,N-Diethyl-meta-toluamide, also called diethyltoluamide or DEET, is the oldest, one of the most effective and most common active ingredient in commercial insect repellents. It is a slightly yellow oil intended to be applied to the skin or to clothing and provides protection against mosquitoes, flies, ticks, fleas, chiggers, leeches, and many other biting insects.

<span class="mw-page-title-main">Bifenthrin</span> Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.

<span class="mw-page-title-main">Permethrin</span> Medication and insecticide

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 outer clothing or mosquito nets to kill the insects that touch them.

<span class="mw-page-title-main">Carbaryl</span> Chemical compound

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

<span class="mw-page-title-main">Malathion</span> Chemical compound

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

<span class="mw-page-title-main">Larvicide</span> Insecticide against the larval stage

A larvicide is an insecticide that is specifically targeted against the larval life stage of an insect. Their most common use is against mosquitoes. Larvicides may be contact poisons, stomach poisons, growth regulators, or (increasingly) biological control agents.

<span class="mw-page-title-main">Fenoxycarb</span> Chemical compound

Fenoxycarb is a carbamate insect growth regulator. It has a low toxicity for bees, birds, and humans, but is toxic to fish. The oral LD50 for rats is greater than 16,800 milligrams per kilogram (0.269 oz/lb).

<span class="mw-page-title-main">Pyriproxyfen</span> Chemical compound

Pyriproxyfen is a pesticide which is found to be effective against a variety of insects. It was introduced to the US in 1996, to protect cotton crops against whitefly. It has also been found useful for protecting other crops. It is also used as a prevention for flea control on household pets, for killing indoor and outdoor ants and roaches. Methods of application include aerosols, bait, carpet powders, foggers, shampoos and pet collars.

<span class="mw-page-title-main">Phenothrin</span> Chemical compound

Phenothrin, also called sumithrin and d-phenothrin, 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.

Insecticidal soap is used to control many plant insect pests. Soap has been used for more than 200 years as an insect control. Because insecticidal soap works on direct contact with pests via the disruption of cell membranes when the insect is penetrated with fatty acids, the insect's cells leak their contents causing the insect to dehydrate and die. Insecticidal soap is sprayed on plants until the entire plant is saturated because the insecticidal properties of the soap occurs when the solution is wet. Soaps have a low mammalian toxicity and are therefore considered safe to be used around children and pets, and may be used in organic farming.

<span class="mw-page-title-main">Naled</span> Organophosphate insecticide

Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate.

<span class="mw-page-title-main">Health effects of pesticides</span> How pesticides affect human health

Health effects of pesticides may be acute or delayed in those who are exposed. Acute effects can include pesticide poisoning, which may be a medical emergency. Strong evidence exists for other, long-term negative health outcomes from pesticide exposure including birth defects, fetal death, neurodevelopmental disorder, cancer, and neurologic illness including Parkinson's disease. Toxicity of pesticides depend on the type of chemical, route of exposure, dosage, and timing of exposure.

An insect growth regulator (IGR) is a chemical insecticide that kills insects indirectly by disrupting their life cycles. The term was initially proposed to describe the effects of juvenile hormone analogs. Although the term "insect growth disruptor" more accurately describes the actions of IGRs, it did not become widely used. IGRs encompass chemical classes with three modes of action : juvenile hormone analogs, chitin synthesis inhibitors, and ecdysone receptor agonists.

<span class="mw-page-title-main">Diflubenzuron</span> Chemical compound

Diflubenzuron is an insecticide of the benzoylurea class. It is used in forest management and on field crops to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths. It is a widely used larvicide in India for control of mosquito larvae by public health authorities. Diflubenzuron is approved by the WHO Pesticide Evaluation Scheme.

Hydroprene is an insect growth regulator used as an insecticide. It is used against cockroaches, beetles, and moths. Products using hydroprene include Gencor, Gentrol, and Raid Max Sterilizer Discs. Hydroprene is a synthetic juvenile hormone mimic, disrupting insect larval development such as molting.

Triprene was an insecticide that is not in use. It was an insect growth regulator introduced by Zoecon Corporation under the "Altorick" trademark, registered 1974 and not renewed, expiring in 1980. The EPA records no registration, now or past.

References

  1. Merck Index, 11th Edition, 5906.
  2. "Update of the March 1991 Methoprene R.E.D. Fact Sheet" (PDF). epa.gov. United States Environmental Protection Agency. June 2001. Archived (PDF) from the original on 2022-10-20. Retrieved 2022-12-01.
  3. "Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (10401), S-Methoprene (105402) Fact Sheet" (PDF). U.S. Environmental Protection Agency Office of Pesticide Programs. 2015-08-20.
  4. "Methoprene" (PDF). Water Sanitation and Health. World Health Organization. 2008.
  5. "Methoprene Materials Safety Data Sheet" (PDF). MSDS for Methoprene. Cayman Chemical. 2019.
  6. Walker, A. N.; Bush, P.; Puritz, J.; Wilson, T.; Chang, E. S.; Miller, T.; Holloway, K.; Horst, M. N. (2005). "Bioaccumulation and Metabolic Effects of the Endocrine Disruptor Methoprene in the Lobster, Homarus americanus" (PDF). Integrative and Comparative Biology. 45 (1): 118–26. doi: 10.1093/icb/45.1.118 . PMID   21676752.