Silafluofen

Last updated
Silafluofen
Silafluofen.svg
Names
Preferred IUPAC name
(4-Ethoxyphenyl)[3-(4-fluoro-3-phenoxyphenyl)propyl]di(methyl)silane
Other names
Eflusilanat; Silonen
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.100.662 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C25H29FO2Si/c1-4-27-21-13-15-23(16-14-21)29(2,3)18-8-9-20-12-17-24(26)25(19-20)28-22-10-6-5-7-11-22/h5-7,10-17,19H,4,8-9,18H2,1-3H3 Yes check.svgY
    Key: HPYNBECUCCGGPA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C25H29FO2Si/c1-4-27-21-13-15-23(16-14-21)29(2,3)18-8-9-20-12-17-24(26)25(19-20)28-22-10-6-5-7-11-22/h5-7,10-17,19H,4,8-9,18H2,1-3H3
    Key: HPYNBECUCCGGPA-UHFFFAOYAS
  • Fc2ccc(cc2Oc1ccccc1)CCC[Si](c3ccc(OCC)cc3)(C)C
Properties
C25H29FO2Si
Molar mass 408.588 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Silafluofen is a fluorinated organosilicon pyrethroid insecticide. [1] [2]

Silafluofen is used agriculturally against soil-borne insects such as termites, and as a wood preservative. It is registered in Asia (India, Japan, Taiwan, Vietnam) since at least 1995 for crops such as drupes, tea and rice, but has not been notified or authorised in the European Union for example. [3] [4]

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DDT Organochloride known for its insecticidal properties

Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound, an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. DDT was first synthesized in 1874 by the Austrian chemist Othmar Zeidler. DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. DDT was used in the second half of World War II to limit the spread of the insect-borne diseases malaria and typhus among civilians and troops. Müller was awarded the Nobel Prize in Physiology or Medicine in 1948 "for his discovery of the high efficiency of DDT as a contact poison against several arthropods".

Phenothiazine Heterocyclic compound containing a ring of four carbon, one nitrogen and one sulfur atom

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Pesticide Substance used to destroy pests

Pesticides are substances that are meant to control pests. The term pesticide includes all of the following: herbicide, insecticides nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, antimicrobial, fungicide, and lampricide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. As an example, the fungus Alternaria solani is used to combat the aquatic weed Salvinia.

Insecticide Pesticide used against insects

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.

Pesticide resistance Decreased effectiveness of a pesticide on a pest

Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then the pesticide lacks efficacy – efficacy and resistance are inversely related.

Cypermethrin Chemical compound

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 degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticides Telecommunications Network (NPTN). It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some products of Baygon in Southeast Asia.

Piperonyl butoxide Chemical compound

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.

Pyrethrin Class of organic chemical compounds with insecticidal properties

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.

Pyrethroid

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

Imidacloprid 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.

Dichlorvos

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961 and has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. The insecticide has been banned in EU since 1998.

Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine. In the 1980s Shell and in the 1990s Bayer started work on their development.

Spinosad Chemical compound

Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water.

Indoxacarb Chemical compound

Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae. It is marketed under the names Indoxacarb Technical Insecticide, Steward Insecticide and Avaunt Insecticide. It is also used as the active ingredient in the Syngenta line of commercial pesticides: Advion and Arilon.

Environmental impact of pesticides Environmental effect

The environmental effects of pesticides describe the broad series of consequences of using pesticides. The unintended consequences of pesticides is one of the main drivers of the negative impact of modern industrial agriculture on the environment. Pesticides, because they are toxic chemicals meant to kill pest species, can effect non-target species, such as plants, animals and humans. Over 98% of sprayed insecticides and 95% of herbicides reach a destination other than their target species, because they are sprayed or spread across entire agricultural fields. Other agrochemicals, such as fertilizers, can also have negative effects on the environment.

Thiamethoxam Chemical compound

Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

Metofluthrin Pyrethroid used as an insect repellent

Metofluthrin is a pyrethroid used as an insect repellent. The vapors of metofluthrin are highly effective and capable of repelling up to 97% of mosquitoes in field tests. Metofluthrin is used in a variety of consumer products, called emanators, for indoor and outdoor use. These products produce a vapor that protects an individual or area. Effectiveness is reduced by air movement. Metofluthrin is neurotoxic, and is not meant to be applied directly to human skin.

Nereistoxin Chemical compound

Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the ISO common names bensultap, cartap, thiocyclam and thiosultap.

References

  1. Sieburth, Scott McNeill; Manly, Charles J.; Gammon, Derek W. (1990). "Organosilane insecticides. Part I: biological and physical effects of isosteric replacement of silicon for carbon in etofenprox and MTI 800". Pesticide Science. 28 (3): 289–307. doi:10.1002/ps.2780280308.
  2. Showell, G. A.; Mills, J. S. (2003). "Chemistry Challenges in Lead Optimization: Silicon Isosteres in Drug Discovery". Drug Discovery Today. 8 (12): 551–556. doi:10.1016/S1359-6446(03)02726-0. PMID   12821303.
  3. "Silafluofen". EU Pesticides database. European Commission. Retrieved 26 January 2022.
  4. Katsuda, Yoshio; Minamite, Yoshihiro; Vongkaluang, Charunee (December 2011). "Development of Silafluofen-Based Termiticides in Japan and Thailand". Insects. 2 (4): 532–539. doi: 10.3390/insects2040532 . PMC   4553446 . PMID   26467832.