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Pyrethrin
The pyrethrins are a class of organic compounds normally derived from ''Chrysanthemum cinerariifolium'' that have potent Insecticide, insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic horticulture, organic insecticide when it is not combined with piperonyl butoxide or other synthetic agricultural spray adjuvant, adjuvants.Mader, Eric, and Nancy Lee Adamson. "Organic-Approved Pesticides."Organic-Approved Pesticides (n.d.): n. pag. The Xerxes Society. The Xerces Society for Invertebrate Conservation, Oct. 2012. Web. 10 Mar. 2015. Their insecticidal and insect-repellent properties have been known and used for thousands of years. Pyrethrins are gradually replacing organophosphates and organochlorides as the pesticides of choice as the latter compounds have been shown to have significant and persistent toxic effects to humans. They first appeared on markets in the 1900s and have bee ...
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Pyrethrum
''Pyrethrum'' was a genus of several Old World plants now classified in either '' Chrysanthemum'' or '' Tanacetum'' which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly included in the genus ''Pyrethrum''. Pyrethrum is also the name of a natural insecticide made from the dried flower heads of '' Chrysanthemum cinerariifolium'' and '' Chrysanthemum coccineum''. The insecticidal compounds present in these species are pyrethrins. Description Some members of the genus ''Chrysanthemum'', such as the following two, are placed in the genus '' Tanacetum'' instead by some botanists. Both genera are members of the daisy (or aster) family, Asteraceae. They are all perennial plants with a daisy-like appearance and white petals. * '' Tanacetum cinerariifolium'' is called the Dalmatian chrysanthemum, denoting its origin in that region of the Balkans (Dalmatia). It looks more like the common daisy than other py ...
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Pyrethrin I
Pyrethrin I is one of the two pyrethrins, natural organic compounds with potent insecticidal activity. It is an ester of (+)-''trans''- chrysanthemic acid with (''S'')-(''Z'')- pyrethrolone. Total synthesis The synthesis of pyrethrin I involves the esterification of (+)-''trans''-chrysanthemic acid with (S)-(Z)-pyrethrolone. One synthetic method for each of these is shown in the images below. Sobti and Dev of the Malti-Chem Research Centre in Nadesari, vadodara, India published this method for chrysanthemic acid in 1974. The starting material for the synthesis uses commercially available (+)-3α, 4α-epoxycarane (1). A lactone is eventually formed and the ring is opened by the use of a Grignard reagent to give (+)-trans-chrysanthemic acid. The preparation of (''S'')-pyrethrolone is essentially a 2 step synthesis. The starting material (S)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one (7) is also commercially available as the alcohol moiety of ETOC. Tetrakis(triphenylphosph ...
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Pyrethrin II
Pyrethrin II is an organic compound that is a potent insecticide. It is one of the two pyrethrins, the other being pyrethrin I. Thousands of tons this mixture are produced annually from chrysanthemum plants, which are cultivated in warm climates.Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. Structure and related compounds Whereas pyrethrin I is a derivative of (+)-''trans''- chrysanthemic acid, in pyrethrin II one methyl group is oxidized to a carboxymethyl group, the resulting core being called pyrethric acid. Knowledge of their chemical structures opened the way for the production of synthetic analogues, which are called pyrethroids. In terms of their biosynthesis, pyrethrins are classified as terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterp ...
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Hermann Staudinger
Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also known for his discovery of ketenes and of the Staudinger reaction. Staudinger, together with Leopold Ružička, also elucidated the molecular structures of pyrethrin I and II in the 1920s, enabling the development of pyrethroid insecticides in the 1960s and 1970s. Early work Staudinger was born in 1881 in Worms. Staudinger, who initially wanted to become a botanist, studied chemistry at the University of Halle, at the TH Darmstadt and at the LMU Munich. He received his "Verbandsexamen" (comparable to Master's degree) from TH Darmstadt. After receiving his Ph.D. from the University of Halle in 1903, Staudinger qualified as an academic lecturer at the University of Strasbourg in 1907. He was supported in his work by his new wife Dora ...
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Persian Powder
Persian powder is an insecticide powder with natural pyrethrin as the active agent. It is also known as Persian pellitory, insect powder and internationally as pyrethrum. Biological pest control Persian powder is a green pesticide that has been used for centuries for the biological pest extermination of household insects, garden pests, and agricultural pests.''Bioaromatica'The history of pyrethrum It may first have been exported from Persia to Ancient Rome. Pyrethrin and pyrethroids are used indoors, in gardens and the horticulture industry, and in agriculture. It is produced from the powdered flowers of certain species of pyrethrum, plants in the genera ''Chrysanthemum'' and '' Tanacetum''. In more recent times it has had formulations with brand names such as Zacherlin. Synthetic forms Pyrethroids are synthetic insecticides based on natural pyrethrum (pyrethrins), such as permethrin. A common formulation of pyrethrin is in preparations containing the synthetic chemic ...
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Insecticide
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. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. Some insecticides (including common bug sprays) are effective against other non-insect arthropods as well, such as scorpions, spiders, etc. Insecticides are distinct from insect repellents, which repel but do not kill. Sales In 2016 insecticides were estimated to account for 18% of worldwide pesticide sales. Worldwide sales of insecticides in 2018 were estimated as $ 18.4 billion, of which 25% were neonicotinoids, 17% were pyrethroids, 13% were diamides, and the rest were many other classes which sold for less th ...
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Chrysanthemum
Chrysanthemums ( ), sometimes called mums or chrysanths, are flowering plants in the Asteraceae family. They are native to East Asia and northeastern Europe. Most species originate from East Asia, and the center of diversity is in China. Countless horticultural varieties and cultivars exist. Description The genus ''Chrysanthemum'' are perennial herbaceous flowering plants, sometimes subshrubs. The leaves are alternate, divided into leaflets and may be pinnatisect, lobed, or serrate (toothed) but rarely entire; they are connected to stalks with hairy bases. The compound inflorescence is an array of several flower heads, or sometimes a solitary head. The head has a base covered in layers of phyllaries. The simple row of ray florets is white, yellow, or red. The disc florets are yellow. Pollen grains are approximately 34 microns. The fruit is a ribbed achene.
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Pyrethroids
A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. In household concentrations pyrethroids are generally harmless to humans. However, pyrethroids are toxic to insects such as bees, dragonflies, mayflies, gadflies, and some other invertebrates, including those that constitute the base of aquatic and terrestrial food webs. Pyrethroids are toxic to aquatic organisms, especially fish.Pyrethroids fact sheet
from the Illinois Department of Public Health.
They have been shown to be an effective control measure for malaria outbreaks, through indoor applications.


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Pyrethr ...
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Insecticide
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. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. Some insecticides (including common bug sprays) are effective against other non-insect arthropods as well, such as scorpions, spiders, etc. Insecticides are distinct from insect repellents, which repel but do not kill. Sales In 2016 insecticides were estimated to account for 18% of worldwide pesticide sales. Worldwide sales of insecticides in 2018 were estimated as $ 18.4 billion, of which 25% were neonicotinoids, 17% were pyrethroids, 13% were diamides, and the rest were many other classes which sold for less th ...
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Chrysanthemum Cinerariifolium
''Tanacetum cinerariifolium'' is a species of flowering plant in the aster family, Asteraceae, and formerly part of the genus '' Pyrethrum'', but now placed in the genus '' Chrysanthemum'', or the genus '' Tanacetum'' by some biologists. It is called the Dalmatian chrysanthemum or Dalmatian pyrethrum, denoting its origin in that region of Europe (Dalmatia). It looks more like the common daisy than other pyrethrums do. Its flowers, typically white with yellow centers, grow from numerous fairly rigid stems. Plants have blue-green leaves and grow to 45 to 100 cm (18 to 39 in) in height. As an insecticide The plant is economically important as a natural source of an insecticide called "pyrethrum." The flowers are pulverized and the active components, called pyrethrins, contained in the seed cases, are extracted and sold in the form of an oleoresin. This is applied as a suspension in water or oil, or as a powder. Pyrethrins attack the nervous systems of all insects, and inhibi ...
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Piperonyl Butoxide
Piperonyl butoxide (PBO) is a pale yellow to light brown liquidNational Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. 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. History PBO was developed in the late 1930s and early 1940s to enhance the performance of the naturally derived insecticide pyrethrum. Pyrethrum is a type of potent insecticide that kills mosquitoes and other disease-ca ...
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