chrysanthemic acid/pyrethrum

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Production of trans-chrysanthemic acid, the monoterpene acid moiety of natural pyrethrin insecticides, in tomato fruit.

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The pyrethrum plant, Tanacetum cinerariifolium (Asteraceae) synthesizes a class of compounds called pyrethrins that have strong insecticidal properties but are safe to humans. Class I pyrethrins are esters of the monoterpenoid trans-chrysanthemic acid with one of three jasmonic-acid derived

Synthesis of citrophilus mealybug sex pheromone using chrysanthemol extracted from Pyrethrum (Tanacetum cinerariifolium).

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A commercial pyrethrum extract was used as a source of chrysanthemol for the synthesis of the citrophilus mealybug (Pseudococcus calceolariae) sex pheromone. The chrysanthemic acid esters (pyrethrins I) were isolated and subsequently reduced to obtain chrysanthemol, which was used for ester

Bidirectional secretions from glandular trichomes of pyrethrum enable immunization of seedlings.

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Glandular trichomes are currently known only to store mono- and sesquiterpene compounds in the subcuticular cavity just above the apical cells of trichomes or emit them into the headspace. We demonstrate that basipetal secretions can also occur, by addressing the organization of the biosynthesis and

Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II.

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Pyrethrum (Tanacetum cinerariifolium) produces insecticidal compounds known as pyrethrins. Pyrethrins are esters; the acid moiety is either trans-chrysanthemic acid or pyrethric acid and the alcohol moiety of pyrethrins is either pyrethrolone, cinerolone, or jasmolone. It was generally accepted that

(1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata.

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Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural

Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods.

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Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin-I and three pyrethrin-II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alcohol components [(S)-cinerolone, (S)-jasmololone, (S)-pyrethrolone] were

Polyenylcyclopropane carboxylic esters with high insecticidal activity.

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BACKGROUND Pyrethroids are synthetic derivatives of naturally occurring pyrethrum. These molecules are widely used in agriculture for ant, fly and mosquito control and for lawn and garden care. Pyrethroids are the optically active esters of 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropane carboxylic

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