ChemicalBook--->CAS DataBase List--->58769-20-3

58769-20-3

58769-20-3 Structure

58769-20-3 Structure
IdentificationBack Directory
[Name]

KADETHRIN
[CAS]

58769-20-3
[Synonyms]

ru15525
ent29117
spray-tox
KADETHRIN
AI3-29117
Kadethrine
BRN 1605066
cis-kadethrin
1r,cis-ru15525
EINECS 261-433-0
Caswell No. 516AA
KADETHRINE STANDARD
KADETHRIN PESTANAL
5-benzyl-3-furylmethyl
)-cyclopropanecarboxylate
KADETHRIN PESTANAL 250 MG
UGWALRUNBSBTGI-ZKMZRDRYSA-N
yl)cyclopropanecarboxylate.
Kadethrine@100 μg/mL in Methanol
o-3(2h)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylate
(5-(phenylmethyl)-3-furanyl)methylester,(1r-(1-alpha,3-alpha(e)))-imethyl
[1r-[1alpha,3alpha(e)]]-[5-(phenylmethyl)-3-furanyl]methyl3-[(dihydro-2-ox
5-benzyl-3-furylmethyl(e)-(1r)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemeth
cyclopropanecarboxylicacid,3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-d
5-benzyl-3-furylmethyl(e)-(1r,3s)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl
3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-dimethyl-,(5-(phenylmethyl)-3-furanyl)
5-benzyl-3-furylmethyl(+)-cis-(1r,3s,e)2,2-dimethyl-3-(2-oxo-2,3,4,5-tetrahydrothiophenylidenemethy
[5-(PHENYLMETHYL)-3-FURANYL]-METHYL-3-[(DIHYDRO-2-OXO-3(2H)-THIENYLIDENE) METHYL]-2,2-DIMETHYLCYCLOPROPANE
3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-dimethyl-,(5-(phenylmethyl)-3-furanyl)methylester,cyclopropanecarboxylicaci
[5-benzyl-3-furyl]methyl [1R-[1alpha,3alpha(E)]]-3-[(dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylate
(1R,3S)-3-[[(E)-4,5-Dihydro-2-oxothiophen-3(2H)-ylidene]methyl]-2,2-dimethylcyclopropanecarboxylic acid (5-benzyl-3-furyl)methyl ester
(1R,3S)-3-[(E)-(Dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylic acid [5-(phenylmethyl)-3-furanyl]methyl ester
Cyclopropanecarboxylic acid, 3-[(E)-(dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethyl-, [5-(phenylmethyl)-3-furanyl]methyl ester, (1R,3S)-
[EINECS(EC#)]

261-433-0
[Molecular Formula]

C23H24O4S
[MDL Number]

MFCD16657115
[MOL File]

58769-20-3.mol
[Molecular Weight]

396.5
Chemical PropertiesBack Directory
[Melting point ]

31℃
[Boiling point ]

526.2±50.0 °C(Predicted)
[density ]

1.278±0.06 g/cm3(Predicted)
[vapor pressure ]

5×10-6Pa (20 °C)
[Fp ]

100 °C
[storage temp. ]

0-6°C
[Water Solubility ]

1mg l-1(20°C)
[EPA Substance Registry System]

Kadethrin (58769-20-3)
Safety DataBack Directory
[Hazard Codes ]

Xn,N
[Risk Statements ]

20/21/22-50/53
[Safety Statements ]

13-60-61
[RIDADR ]

UN 3082 9/PG 3
[RTECS ]

GZ1266550
[Hazardous Substances Data]

58769-20-3(Hazardous Substances Data)
Hazard InformationBack Directory
[Uses]

Kadethrin is used to control household pests, particularly houseflies, mosquitoes and cockroaches. It is normally used in combination with other pyrethroid insecticides and synergists.
[Metabolic pathway]

Kadethrin is used almost wholly indoors and therefore little has been published on its environmental fate. Information on its photodegradation and metabolism in rats has been reported.
[Degradation]

Kadethrin is unstable to heat and it is rapidly decomposed by light. It is hydrolysed in aqueous alkaline solution to (E)-(1R)-cis-2,2-dimethyl-3- (2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylic acid (2), 5-benzyl- 3-furylmethanol (3) and its thiolactone ring-opened derivative (5) (Scheme 1).
Products of photodecomposition have been reported by Ohsawa and Casida (1979). Photo-hydrolysis of kadethrin occurs on sunlight irradiation affording 2 and 5 and 5-benzyl-3-furancarboxylic acid (4), presumably via the alcohol (3). cis-trans Isomerisation of the cyclopropane ring and E-Z interconversion about the double bond was also noted. Thus, from the lRcisE isomer (kadethrin), all of the possible isomers were found to varying degrees (ie. 1RScis-trans-E-Z mixtures).
Photo-hydrolysis products (e.g. 2 and 5) were also found aS isomers. The facility of the isomerisation process was considered to be due to resonance stabilisation of a triplet diradical, one form of which (6) is shown in Scheme 1. Kadethrin also yielded a lactone (7) derived from the cyclopropane ring. Photo-oxidation of the alcohol moiety analogous to that reported for resmethrin was also found. The hydroxylactone (8) and the benzyloxylactone (9) were reported (but the hydroxycyclopetenolone [resmethrin, 61) was absent.
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