2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat

Bezeichnung:2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat

CAS-Nr23031-36-9

Englisch Name:Prallethrin

CBNumberCB4471390

SummenformelC19H24O3

Molgewicht300.39

MOL-Datei23031-36-9.mol

Synonyma

2-Methyl-4-oxo-3-(prop-2-inyl)cyclopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropancarboxylat

2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat

2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	25°C
Siedepunkt	381.62°C (rough estimate)
Dichte	d420 1.03
Dampfdruck	﹤4.3×10^-5 Pa (23.1 °C)
Brechungsindex	1.4200 (estimate)
Flammpunkt	139 °C
storage temp.	2-8°C
Löslichkeit	Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)
Wasserlöslichkeit	8 mg l^-1 (25 °C)
Stabilität	Stable. Incompatible with strong oxidizing agents.
CAS Datenbank	23031-36-9(CAS DataBase Reference)
EPA chemische Informationen	Prallethrin (23031-36-9)

Sicherheit

Kennzeichnung gefährlicher	T,N
R-Sätze:	22-23-50/53
S-Sätze:	45-60-61
RIDADR	UN2811 6.1/PG 2
WGK Germany	3
HS Code	29162090
Giftige Stoffe Daten	23031-36-9(Hazardous Substances Data)
Toxizität	mouse,LD50,oral,190mg/kg (190mg/kg),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 228, 1989.

Gefahreninformationscode (GHS)

Prallethrin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R23:Giftig beim Einatmen.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Chemische Eigenschaften
solid
Verwenden
Prallethrin is used for the control of insects in domestic and public health situations.
Verwenden
Prallethrin ia a synthetic pyrethroid; propynyl analog of allethrin. Prallethrin is used as an insecticide.
Definition
ChEBI: Prallethrin is a member of cyclopropanes and a terminal acetylenic compound. It has a role as a pyrethroid ester insecticide and an agrochemical. It is functionally related to a chrysanthemic acid.
Hazard
A poison by ingestion and inhalation. Low toxicity by skin contact.
Pharmakologie
Prallethrin is a propynyl analog of allethrin, with 2-methyl-4-oxo-3-(prop-2-ynyl)-cyclopent-2-enyl as the secondary alcohol moiety that has been introduced against public health pests (113–115). The ester of the (S)-alcohol with (1R)-trans,cis-chrysanthemic acid resolved partially is commercialized on the strength of the assessment of insecticidal action of individual stereoisomers (116). Compared with d-allethrin, it is approximately four, six, and five times more effective on Musca domestica (for killing), Blattella germanica (for killing), and Culex pipiens pallens (for knockdown), respectively (43). A lower level of resistance to prallethrin than to phenoxybenzyl pyrethroids was demonstrated in a kdr-resistant housefly strain (116).
Sicherheitsprofil
A poison by ingestion and inhalation. Low toxicity by skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.
Stoffwechselwegen
Prallethrin is stable under normal room temperature storage conditions for up to 36 months. It is labile to alkali at the ester linkage, forming 2 and 3 (Scheme 1). Analogy with the allethrins (from which it differs only in the degree of unsaturation in the side chain - propyne rather than propene) would suggest that the compound is very photolabile.
Degradation
The metabolism of prallethrin was studied following single oral administration and subcutaneous injection of the cis- and trans-isomers to rats at two dose levels and after repeated dosing. The compound was labelled in the alcohol moiety (inferred from the results) (PSD, 1995).
Absorption was rapid with maximum tissue residues being attained 3 hours after the dosing of each isomer. Biphasic clearance of radioactivity then occurred with half-lives of 3 and 14-23 hours (cis-isomer) and 3-5 and 7-35 hours (trans-isomer). Urinary excretion accounted for 13-32% (cis-isomer) and 45-62% (trans-isomer) of the dose with most of the balance in the faeces. Less than 0.1% was exhaled as ¹⁴CO₂ . Residues in tissues were very low (0.3% of the dose at 7 days). Metabolism and disposition were independent of dose and dose route but residues in tissues were somewhat higher for the cis-isomer.
Twenty-one metabolites were identified (taking account of stereochemistry and conjugates). The major pathways of metabolism involved oxidation at a methyl group of the isobutenyl group in the acid moiety (giving 4 and 5), at the C1 and C2 positions of the propynyl group in the alcohol moiety (giving 6 and 9) and dihydroxylation (to 7 and 8). The resulting hydroxy derivatives were conjugated with glucuronic acid and sulfate.
Hydrolysis of prallethrin also occurred to afford the acid 2 (presumed) and the alcohol 3. Hydrolysis of the hydroxylated prallethrins and further oxidation of 3 afforded 10 and 11. Further oxidation of 10 to the cyclic tertiary alcohol (12) was observed.
When bluegill sunfish were exposed to a l4C-labelled (acid and alcohol groups) prallethrin isomer (1Rtrans), more than 50% of the biliary radioactivity recovered from the gall bladder was observed as one ester metabolite. This was identified as the taurine conjugate of carboxylic acid metabolite 5 (Oshima et al., 1992).

Prallethrin Upstream-Materialien And Downstream Produkte

2-Methyl-4-oxo-3-(prop-2-inyl)cy-clopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropan-carboxylat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

23031-36-9, Prallethrin Verwandte Suche:

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