Names | |
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Preferred IUPAC name N-[(4-tert-Butylphenyl)methyl]-4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide | |
Other names 4-Chloro-N-[[4-(1,1-dimethylethyl)phenyl]]methyl]-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.122.745 |
KEGG |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C18H24ClN3O | |
Molar mass | 333.86 g·mol−1 |
Appearance | White crystalline solid |
Density | 0.5 g/mL at 24.1 °C |
Melting point | 64 to 66 °C (147 to 151 °F; 337 to 339 K) |
2.61 ppm at pH 5.9 3.21 ppm at pH 4 2.39 ppm at pH 7 2.32 ppm at pH 10 | |
Acidity (pKa) | 5.9 in water |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tebufenpyrad is an insecticide and acaricide widely used in greenhouses. [2] It is a white solid chemical with a slight aromatic smell. It is soluble in water and also in organic solvents. [3]
Tebufenpyrad is a strong mitochondrial complex I inhibitor. [4] [5] It is one of the METI acaricides and insecticides in IRAC group 21A. Like Rotenone, it inhibits electron transport chain by inhibiting the complex I enzymes of mitochondria which ultimately leads to lack of ATP production and finally cell death.
Tebufenpyrad is used mainly in greenhouses around the world. It has been registered under various trade names (i.e.Masai, Pyranica) [6] in countries like Australia, China and certain South American countries. It is registered in USA for use on ornamental plants in commercial green houses. [1] : 1 The data available presented enough evidence to support unconditional registration of tebufenpyrad for use on ornamental plants in greenhouses. [1] : 13
It is mainly used in greenhouses and the major form of exposure is through occupational exposure where this chemical is manufactured or used extensively. The possible routes of exposure are through inhalation or dermal exposure. [3] Since it is used in ornamental plants the exposure through food is limited. The LD 50 values for various laboratory animals are as follows: LD50 Rat (male) oral 595 mg/kg LD50 Rat (female) oral 997 mg/kg LD50 Mouse (male) oral 224 mg/kg LD50 Mouse (female) oral 210 mg/kg LD50 Rat dermal >2000 mg/kg [7]
Hydroxylation is the major and primary biotransformation of tebufenpyrad reported both in vivo and in vitro. Ethyl and tert.-butyl groups are the targets of hydroxylation. The alcohol groups are oxidized to carboxylic groups which can then be conjugated with other groups in vivo. [8] In rodent studies it was shown that 80% of the pesticide was absorbed mainly in the digestive system within 24 hours, the major metabolites being the hydroxylated forms. Most of the compound and its metabolites were excreted through feces and urine. There was no evidence of accumulation in the body of the rodents. [1] : 11 The metabolites excreted out differed from male to female in rodents. While males excreted the carboxylic derivatives of the parent compound, the female rats excreted the sulfate conjugates of carboxylic acid. The LD50 values of male and female rats was very different. While the LD50 value of female rats was 997 mg/kg the LD50 for male rats was only 595 mg/kg. [7] This vast difference in LD 50 value might be attributed to this biotransformation.
Tebufenpyrad exposure has been linked to cancer but to date no human data has been conclusive enough to link the two. [9] Recently this pesticide has been shown to affect the dopaminergic neuronal cell lines N27 by disrupting the mitochondrial dynamics. Loss of dopaminergic cells have been linked to Parkinson's disease in which the neuronal mitochondria are affected. [10] These findings may show that tebufenpyrad might also be able to affect the neurons. Overexposure of the pesticide has also led to the development of resistance among different target organisms. [11] Recent studies have detected tebufenpyrad resistance in two spider mite species in apple trees in Western Australia. [12]
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. It is a non-systemic and non-volatile insecticide that acts by contact and ingestion, used in agriculture and in pest control products. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticide Information Center (NPIC) in the USA. It is found in many household ant and cockroach killers, including Raid, Ortho, Combat, ant chalk, and some products of Baygon in Southeast Asia.
Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.
Ethion (C9H22O4P2S4) is an organophosphate insecticide. It is known to affect the neural enzyme acetylcholinesterase and disrupt its function.
Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.
Amitraz is a non-systemic acaricide and insecticide and has also been described as a scabicide. It was first synthesized by the Boots Co. in England in 1969. Amitraz has been found to have an insect repellent effect, works as an insecticide and also as a pesticide synergist. Its effectiveness is traced back on alpha-adrenergic agonist activity, interaction with octopamine receptors of the central nervous system and inhibition of monoamine oxidases and prostaglandin synthesis. Therefore, it leads to overexcitation and consequently paralysis and death in insects. Because amitraz is less harmful to mammals, amitraz is among many other purposes best known as insecticide against mite- or tick-infestation of dogs. It is also widely used in the beekeeping industry as a control for the Varroa destructor mite, although there are recent reports of resistance.
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.
Dimethoate is a widely used organophosphate insecticide and acaricide. It was patented and introduced in the 1950s by American Cyanamid. Like other organophosphates, dimethoate is an acetylcholinesterase inhibitor which disables cholinesterase, an enzyme essential for central nervous system function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly. One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.
Hydramethylnon is an insecticide used primarily in the form of baits for cockroaches and ants. It works by inhibiting complex III in the mitochondrial inner membrane and leads to a halting of oxidative phosphorylation. Some brands of hydramethylnon are Amdro, Blatex, Combat, Cyaforce, Cyclon, Faslane, Grant's, Impact, Matox, Maxforce, Pyramdron, Siege, Scuttle and Wipeout. Hydramethylnon is a slow-acting poison with delayed toxicity that needs to be eaten to be effective.
Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.
Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.
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.
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.
Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V-sub x and GD-7.
Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.
Phorate is an organophosphate used as an insecticide and acaricide.
Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.
Triazofos is a chemical compound used in acaricides, insecticides, and nematicides.
Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan.
Etoxazole is a narrow spectrum systemic acaricide used to combat spider mites. It targets a variety of mites in the egg, larvae and nymph stages however not the adult stage. It also exhibits insecticidal activity towards aphids, the green rice leafhopper and diamondback moth. The mode of action has been shown to inhibit chitin synthase (IRAC group 10B). Resistance due to its high efficacy and cross resistance when used with other acaricides are both of concern similar to was seen in the fast development of cross resistance in the previous generation of acaricides. The LC50 for resistant mite strains has been observed over 100,000 times greater than that of susceptible strains. Thus resistance management strategies are important in order to limit the increase of etoxazole resistant mite strains.
Cadusafos is a chemical insecticide and nematicide often used against parasitic nematode populations. The compound acts as a acetylcholinesterase inhibitor. It belongs the chemical class of synthetic organic thiophosphates and it is a volatile and persistent clear liquid. It is used on food crops such as tomatoes, bananas and chickpeas. It is currently not approved by the European Commission for use in the EU. Exposure can occur through inhalation, ingestion or contact with the skin. The compound is highly toxic to nematodes, earthworms and birds but poses no carcinogenic risk to humans.
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