Kadethrin

Kadethrin^[1]
Names

Preferred IUPAC name (5-Benzylfuran-3-yl)methyl (1R,3S)-2,2-dimethyl-3-[(E)-(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylate
Identifiers
CAS Number	58769-20-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1605066
ChEBI	CHEBI:39392
ChemSpider	20142266^Y
ECHA InfoCard	100.055.830
EC Number	261-433-0
PubChem CID	12940701
RTECS number	GZ1266550
UNII	N52O84U83Z^Y
CompTox Dashboard (EPA)	DTXSID5042083
InChI InChI=1S/C23H24O4S/c1-23(2)19(12-17-8-9-28-22(17)25)20(23)21(24)27-14-16-11-18(26-13-16)10-15-6-4-3-5-7-15/h3-7,11-13,19-20H,8-10,14H2,1-2H3/b17-12+/t19-,20-/m0/s1^Y Key: UGWALRUNBSBTGI-ZKMZRDRYSA-N^Y InChI=1/C23H24O4S/c1-23(2)19(12-17-8-9-28-22(17)25)20(23)21(24)27-14-16-11-18(26-13-16)10-15-6-4-3-5-7-15/h3-7,11-13,19-20H,8-10,14H2,1-2H3/b17-12+/t19-,20-/m0/s1 Key: UGWALRUNBSBTGI-ZKMZRDRYBN
SMILES O=C(OCc2cc(Cc1ccccc1)oc2)[C@@H]4[C@H](\C=C3/CCSC3=O)C4(C)C
Properties
Chemical formula	C₂₃H₂₄O₄S
Molar mass	396.50 g·mol⁻¹
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H410
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, P501
Flash point	100 °C (212 °F; 373 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Kadethrin is a synthetic pyrethroid with the chemical formula C₂₃H₂₄O₄S which is used as an insecticide. It is the most potent knockdown pyrethroid (even stronger than pyrethrin II) but it is relatively unstable, especially when exposed to light (due to both the furan ring and the thiolactone group in the molecule).^[2]

References

^ Kadethrin at Sigma-Aldrich
^ John E. Casida (1980). "Pyrethrum Flowers and Pyrethroid Insecticides". Environmental Health Perspectives. 34: 189–202. doi:10.2307/3428960. JSTOR 3428960. PMC 1568513. PMID 6993201.