Pyrethrolone ester

Pyrethrum (Chrysanthemum) dnerarifolium (Asteraceae) namely cinerin I (CMC cineralone ester), cinerin II (CDC monomethyl ester cinerolone ester), pyrethrin I (CMC pyrethrolone ester) and pyrethrin II (CDC monomethyl ester pyrethrolone ester). The chrysanthemum carboxylic acids are cyclopropane-based monoterpenes and cineralone and pyrethrolone are cyclopentanone monoterpene alcohols. The pyrethrins (and their insecticidal synthetic derivatives) are toxic to insects through keeping cell membrane voltage-gated Na+ channels open and thus impairing neurotransmission. 

Pyrethrin I (= Chrysanthemum monocarboxylic acid pyrethrolone ester) (monoterpene)... 

SYNS CHRYSANTHEMUMDICARBOXYLIC ACID MONOMETHYL ESTER PYRETHROLONE ESTER ... 

ENT 7,543 PYRETHRIN PYRETHROLONE CHRYSANTHEMUM DICARBOXLIC ACID METHYL ESTER PYRETHROLONE ESTER of CHRYSANTHEMUMDICARBOXYLIC ACID MONOMETHYL ESTER (-f)-PYRETHRONYL (+)-PYRETHRATE PYRETRIN II... 

CAS 8003-34-7. C21H2803. Pyrethrolone ester of chrysanthemummonocarboxylic acid. Most potent insecticidal ingredient of pyrethrum flowers. 

Pyrethrin II, CjjHjjO, 3-(3-methoxy-2-methyl.3-oxo-l-fmpenyl)-2,2 dimethyicyclopropanecarboxyiic acid 2-methyl 4-penten-1 -vl ester. ehrysan-tlumamdicarboxylic acid monomethyl ester pyrethrolone ester. R = COOCHj. Viscous liquid. Oxidizes rapidly and becomes inactive in air. bPsatr 192-193 - njj 1.5355. [a]tf +14.7 (isooctane-ether), uv max (95% ethanol) 229 an (e 45,850). Practically insol in water sol in ale, petr ether dess sol than pyrethrin I), kerosene, carbon tetrachloride, ethyl -me dichloride, nitromethane. LDm orally in rats 1.2 g/kg. 

Beilstein Handbook Reference) BRN 2004306 Caswell No. 715 Chrysanthemum mono-carboxylic acid pyrethrolone ester EINECS 204-455-8 EPA Pesticide Chemical d)de 069001 HSDB 6302 Piretrina 1 Pyrethrin I Pyrethrine I Pyrethrins Pyrethrolone, chrysanthemum monocarboxylic acid ester Pyrethronyl (+)-trans-chrysanthemate Pyrethrum RCRA waste number POOS. Registered by EPA as an insecticide. Viscous liquid bpo.1 = 170° d = 1.5192 [a]8 -14° (isooctane) km = 225 nm (e 36400 95% EtOH) insoluble in H2O, soluble in ElOH, petroleum ether, kerosene, CCI4, ethylene dichloride, nitromethane LDso (rat orl) = 584 - 900 mg/kg, (mus orl) = 273 - 796 mg/kg, (rat der) > 1500 mg/kg, (rbt der) = 5000 mg/kg highly toxic to fish toxic to bees, with repellent effect. 

Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone Chrysanthemum dicarboxylic acid monomethyl ester pyrethrolone ester. See Pyrethrin II Chrysanthemum monocarboxylic acid pyrethrolone ester. See Pyrethrin I Chrysoidin Chrysoidine Chrysoidine crystals Chrysoidine special. See Basic orange 2 Chrysoine. See Acid orange 6 Chrysophanic acid... 

Synonyms Chrysanthemum monocarboxylic acid pyrethrolone ester Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one Pyrethrolone, chrysanthemum monocarboxylic acid ester (+)-Pyrethronyl (+)-trans-chrysanthemate Classification Pyrethrins (natural)... 

Pyrethrolone ester of chrysanthemum dicarboxylic acid monomethyl ester (+)-Pyrethronyl ( ( )-pyrethrate Pyretrin II... 

Definition Pyrethrolone ester of chysanthemum monocarboxylic acid Empiricai C22H28O5... 

The great advance in the field of instrumentation, coupled with the discovery of the heterogeneity of the pyrethrolone radical, has advanced the knowledge of pyrethrum chemistry considerably beyond that known in 1945. LaForge and Barthel (24,25) have shown the structure of the active ingredients of pyrethrum, known collectively as pyrethrins, to be esters as represented by the structure shown in Table I. 

Pyrethrolone and cinerolone make up the keto alcohol moiety of the pyrethrins. Both of these keto alcohols have one asymmetric carbon at the 4-position and a double bond in the side chain which is capable of cis-trans isomerism in the 2-position. It is possible, therefore, to have four stereoisomers for each keto alcohol. Katsuda et al. (22) show that only the ( + ) form occurs in the natural esters. Elliott (8) has shown recently, by a new procedure developed to obtain pure ( + ) pyrethrolone, that the hitherto unidentified prye-throlone C is in reality pyrethrolone contaminated with thermally isomerized material. (+) Pyrethrolone forms a crystalline monohydrate from which the pure alcohol is obtained. The natural configurations of the keto alcohols in the esters are insecticidally more active, as is the case with the acid moiety. 

Pyrethroids consist of pyrethrum and its synthetic pyrethrum analogs called synthetic pyrethroids. Pyrethrum is a solvent extract of dried flowers of Chrysanthemum cinerariaefo-lium. The active ingredients of pyrethrum are called pyrethrins. Pyrethrins consist of four esters, namely, pyrethrins I and II and cinerins I and II, which comprise the combination of two different alcohols (pyrethrolone and cinerolone) and two different acids (chrysan-themic acid and pyrethric acid), as follows ... 

The natural pyrethrin insecticides are esters derived from the alcohols cinerolone, jasmololone, and pyrethrolone (Fig. 6). Extracts of pyrethrum, the dried flowerheads of Chrysanthemum cinerariae-folium, contain a mixture of six of these ester (Fig. 6) and are commonly available with the addition of the pyrethrum synergist piperonyl butoxide. Variations on these basic structures have... 

The Chrysanthemum Extract comprise of a mixture oiester e.g., chrysanthemic and pyrethric acids alcohols e.g., cinerolone and pyrethrolone. As the esters are usually more prone to get hydrolyzed and oxidized, hence it must be stored in sealed light-proof containers in a cool place. 

Chrysanthemol from the leaves of Artemisia ludiviciana (Asteraceae) belongs to the cyclopropane monoterpenes Cinerins, jasmolins and pyrethrins (all including derivatives 1 and 11) are esters of /rara-chrysanthemic and pyrethric acid with terpenoid hydroxypentenones such as cinerolone, jasmolone and pyrethrolone. These are the active insecticidal constituents of pyrethrum recovered from dried flowers of several Chrysanthemum species (e.g. Chrysanthemum cinerariaefolium, Asteraceae). Some synthetic esters of chrysanthemic acid are also applied as insecticides. 

In the natural pyrethrin esters, the presence of two asymmetric cyclopropane carbons implies the possible existence of four stereoisomers (Deltamethrin Monograph 1982). However, in the natural pyrethrins, only the (IR, 3R) configuration exists. This fact limits the number of acids (isomers) that need to be considered in developing analytical methods for detecting pyrethrin residues in food products, or animal tissues and fluids (i.e., blood, urine, and feces). For the alcohol component, three alcohols exist pyrethrolone, cinerolone and jasmolone, and all three possess an asymmetric center that has an (S) configuration. 

Pyrethrum flower consists of the dried flowerhead of Chrysanthemum cinerar ice folium Vis. and it owes its insecticidal properties to two types of ketoesters. One group consists of pyrethrin I and cinerin I, both of which have chrysanthemum monocarboxylic acid (chrysanthemic acid) as their acid component. The assay given below for pyrethrin I, which is based on the determination of total chrysanthemic acid, will therefore include cinerin I. The second group of esters consists of pyrethrin II and cinerin II, both of which have the monomethyl ester of chrysanthemum dicarboxylic acid (pyrethric acid) as their acid component since the assay given below for pyrethrin II is based on the determination of total pyrethric acid it will therefore include cinerin II. The keto-alcohol component of the pyrethrins is pyrethrolone and that of the cinerins is cinerolone. 

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