Names | |
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Preferred IUPAC name N-tert-Butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide | |
Other names Mimic, RH-75992, HOE-105540, Confirm 2F, Confirm 70 | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.011.209 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C22H28N2O2 | |
Molar mass | 352.478 g·mol−1 |
Melting point | 191 to 191.5 °C (375.8 to 376.7 °F; 464.1 to 464.6 K) [1] |
0.83 mg/L [1] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
The diacylhydrazines, also known as bisacylhydrazines (BAHs) or dibenzoylhydrazines are appropriately substituted derivatives of dibenzoyl hydrazine. [2] They do not immediately kill the insect, but produces premature unsuccessful moulting, which then causes the death of the insect. BAHs thus belong to the class of insect growth regulators.
The insecticidal activity of RH-5849 was discovered serendipitously in 1984 at Rohm and Haas, who later commercialised tebufenozide methoxyfenozide, and halofenozide. Later other companies commercialised chromafenozide and fufenozide. The EPA removed halofenozide from the market in 2012 on the request of the manufacturer. [2] BAHs were estimated to account for ca 1% of the 18.4-billion-dollar 2018 global pesticide market. [3]
BAHs are used against lepidoptera, with some applications against coleopteran and dipteran pests. [2] Many plants produce chemicals (phytoecdysteroids) which use this mode of action to kill insects.
BAHs act by agonising the ecdysone receptor. Crystal structures of BAHs bound to the ecdysone receptor were obtained. [2]
BAHs show low mammalian and environmental toxicity. Methoxyfenozide was given a presidential green chemistry award in 1998. Both tebufenozide and methoxyfenozide were registered by the EPA under its Reduced Risk Pesticide Program. [2]
Bacillus thuringiensis is a gram-positive, soil-dwelling bacterium, the most commonly used biological pesticide worldwide. B. thuringiensis also occurs naturally in the gut of caterpillars of various types of moths and butterflies, as well on leaf surfaces, aquatic environments, animal feces, insect-rich environments, flour mills and grain-storage facilities. It has also been observed to parasitize moths such as Cadra calidella—in laboratory experiments working with C. calidella, many of the moths were diseased due to this parasite.
Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.
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 that will reduce the pesticide's efficacy – efficacy and resistance are inversely related.
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.
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.
Pest control is the regulation or management of a species defined as a pest; such as any animal, plant or fungus that impacts adversely on human activities or environment. The human response depends on the importance of the damage done and will range from tolerance, through deterrence and management, to attempts to completely eradicate the pest. Pest control measures may be performed as part of an integrated pest management strategy.
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.
A Biopesticide is a biological substance or organism that damages, kills, or repels organisms seens as pests. Biological pest management intervention involves predatory, parasitic, or chemical relationships.
Benzoylureas (BPUs) are chemical derivatives of N-benzoyl-N′-phenylurea, which are used as insecticides. They do not directly kill the insect, but disrupt moulting and egg hatch, and thus act as insect growth regulators. They act by inhibiting chitin synthase, preventing the formation of chitin in the insect's body.
Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.
Cyhalothrin is 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.
Propoxur (Baygon) is a carbamate non-systemic insecticide, produced from catechol, and was introduced in 1959. It has a fast knockdown and long residual effect, and is used against turf, forestry, and household pests and fleas. It is also used in pest control for domestic animals, Anopheles mosquitoes, ants, gypsy moths, and other agricultural pests. It can also be used as a molluscicide.
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.
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.
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.
Diamide insecticides are a class of insecticides, active mainly against lepidoptera (caterpillars), which act on the insect ryanodine receptor. They are diamides of either phthalic acid or anthranilic acid, with various appropriate further substitutions.
Sulfoxaflor, also marketed as Isoclast, 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.
Chlorantraniliprole is an insecticide of the diamide class used for insects found on fruit and vegetable crops as well as ornamental plants.
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.