Names | |
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IUPAC name [Methyl(oxo){1-[6-(trifluoromethyl)-3-pyridyl]ethyl}-λ6-sulfanylidene]cyanamide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.234.961 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H10F3N3OS | |
Molar mass | 277.27 g·mol−1 |
Hazards | |
GHS labelling: [1] | |
Warning | |
H302, H410 | |
P264, P270, P273, P301+P317, P330, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Sulfoxaflor, also marketed as Isoclast, [2] is a systemic insecticide that acts as an insect neurotoxin. A pyridine and a trifluoromethyl compound, it is a member of a class of chemicals called sulfoximines, which act on the central nervous system of insects.
Sulfoxaflor is a systemic insecticide, acts as a neurotoxin to affected insects, and kills through contact or ingestion.
Sulfoxaflor is classified for use against sap-feeding insects as a sulfoximine, which is a sub-group of insecticides that act as nicotinic acetylcholine receptor (nAChR) competitive modulators. [3] [4] Sulfoxaflor binds to nAChRs in place of acetylcholine. Sulfoxaflor binding causes uncontrolled nerve impulses resulting in muscle tremors followed by paralysis and death. [3]
Other nAChR competitive modulator sub-groups that bind differently on the receptor than sulfoximines include neonicotinoids, nicotine, and butenolides. [5] [3] [6]
Because sulfoxaflor binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is selectively more toxic to insects than mammals. [7]
Application is only recommended when pollinators are not likely to be present in an area as sulfoxaflor is highly toxic to bees if they come into contact with spray droplets shortly after application; toxicity is reduced after the spray has dried. [4]
On May 6, 2013, the United States Environmental Protection Agency (EPA) approved the first two commercial pesticide products that contain sulfoxaflor, marketed under the brand names "Transform" and "Closer", to the Dow Chemical Corporation.
On September 10, 2015 the U.S. 9th Circuit Court of Appeals overturned the EPA's approval of sulfoxaflor, citing insufficient evidence from studies regarding bee health to justify how sulfoxaflor was approved. [8] [6] Beekeepers and environmental groups supported the decision, saying that the EPA must assess the health of entire hives, not just individual bees. [9]
On October 14, 2016, the United States Environmental Protection Agency (EPA) approved new registrations for sulfoxaflor, "Transform" and "Closer", to the Dow Chemical Corporation.
Previously, the Dow Chemical Corporation owned and sold these products. However, as of June, 2019, the agricultural wing of the Dow Chemical Corporation was split into an independent public corporation called Corteva Agriscience, who now sells the sulfoxaflor-based pesticides. [10]
On July 12, 2019, the EPA announced it will allow the use of sulfoxaflor, citing new studies that show lower harm levels to bees than other available pesticides. [10] The EPA concluded that sulfoxaflor would lessen the danger to bees since industry-backed studies assessed it dissipated more quickly and required few applications than other pesticides. [11] On December 21, 2022, the US 9th Circuit Court of Appeals ruled that the EPA broke the law in allowing new uses of sulfoxaflor because it failed to assess its risks to endangered species nor give the public a chance to comment on the decision. The court then ordered the EPA to allow the public 180 days to comment on expanding the uses of sulfoxaflor. [12]
The California registration for sulfoxaflor was overturned following a lawsuit filed in 2020 against the state's Department of Pesticide Regulation by beekeepers and environmental groups. [13]
Sulfoxaflor is currently registered in 47 countries, including US, Canada, Mexico, Argentina, Chile, India, China and Australia. [14] The registration of Closer and Transform in France was overturned by a court decision in November, 2017. [15]
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.
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). Although this route of synthesis has faced a lot of criticism in recent times. The new route of synthesis is through 1,2-Methylenedioxybenzene, developed by The Anthea Group and patented in 2019.
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.
In organic chemistry, chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.
Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.
Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.
The coxal gland is a gland found in some arthropods, for collecting and excreting urine. They are found in all arachnids, and in other chelicerates, such as horseshoe crabs. The coxal gland is thought to be homologous with the antennal gland of crustaceans. The gland consists of an end sac (saccule), a long duct (labyrinth) and a terminal bladder (reservoir). There is generally only one pair, and they open on the coxae of the walking legs. The coxal secretion of adult female ticks of Ornithodoros erraticus contains a sex pheromone.
Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.
Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.
Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect neurotoxin belonging to the class of neonicotinoids which works by blocking neural signaling of the central nervous system. It does so by binding irreversibly to the nicotinic acetylcholine receptor (nACHr) causing a stop of the flow of ions in the postsynaptic membrane of neurons leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.
John Edward Casida was an American entomologist, toxicologist and professor at the University of California, Berkeley.
Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.
Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.
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.
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.
Thiacloprid is an insecticide of the neonicotinoid class. Its mechanism of action is similar to other neonicotinoids and involves disruption of the insect's nervous system by stimulating nicotinic acetylcholine receptors. Thiacloprid was developed by Bayer CropScience for use on agricultural crops to control of a variety of sucking and chewing insects, primarily aphids and whiteflies.
Desnitro-imidacloprid is a metabolite of the insecticide imidacloprid, a very common insecticide and the most important member of the class of insecticides called neonicotinoids, the only significant new class of insecticides to be developed between 1970 and 2000. While imidacloprid has proved highly selective against insects, the desnitro- version is highly toxic to mammals, due to its agonist action at the alpha4beta2 nicotinic acetylcholine receptor (nAChR) in the mammalian brain, at least as demonstrated in experiments involving mice.
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.
Flupyradifurone is a systemic butenolide insecticide developed by Bayer CropScience under the name Sivanto. Flupyradifurone protects crops from sap-feeding pests such as aphids and is safer for non-target organisms compared to other insecticides. Sivanto was launched in 2014 since it obtained its first commercial registration in central America. Insecticide Resistance Action Committee (IRAC) classified Flupyradifurone as 4D subset (butenolide) and it is the first pesticide in the butenolide category. It was approved by European Union in 2015.