Kadethrin

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]

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
3D model (JSmol)
1605066
ChEBI
ChemSpider
ECHA InfoCard 100.055.830
EC Number
  • 261-433-0
RTECS number
  • GZ1266550
UNII
  • 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 checkY
    Key: UGWALRUNBSBTGI-ZKMZRDRYSA-N checkY
  • 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
  • O=C(OCc2cc(Cc1ccccc1)oc2)[C@@H]4[C@H](\C=C3/CCSC3=O)C4(C)C
Properties
C23H24O4S
Molar mass 396.50 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H312, H332, H410
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).
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Infobox references

References
  1. Kadethrin at Sigma-Aldrich
  2. 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.


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