Tefluthrin

Tefluthrin

tefluthrin (racemic)
Names
Preferred IUPAC name
rac-(2,3,5,6-Tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]cyclopropane-1-carboxylate
Other names
Tefluthrine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.124.968 Edit this at Wikidata
EC Number
  • 616-699-6
KEGG
UNII
  • InChI=1S/C17H14ClF7O2/c1-6-11(19)13(21)7(14(22)12(6)20)5-27-15(26)10-8(16(10,2)3)4-9(18)17(23,24)25/h4,8,10H,5H2,1-3H3/b9-4-/t8-,10-/m1/s1 checkY
    Key: ZFHGXWPMULPQSE-SZGBIDFHSA-N checkY
  • InChI=1/C17H14ClF7O2/c1-6-11(19)13(21)7(14(22)12(6)20)5-27-15(26)10-8(16(10,2)3)4-9(18)17(23,24)25/h4,8,10H,5H2,1-3H3/b9-4-/t8-,10-/m1/s1
    Key: ZFHGXWPMULPQSE-SZGBIDFHBO
  • CC1=C(C(=C(C(=C1F)F)COC(=O)[C@@H]2[C@@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)F)F
Properties[1]
C17H14ClF7O2
Molar mass 418.74 g·mol−1
Appearance colorless solid
Density 1.48 g/mL
Melting point 44.6 °C
Boiling point 156 °C at 1 mmHg
0.02 mg/L in water

>500 g/L in acetone, hexane, toluene

log P 6.4
Hazards[2]
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H300, H310, H330, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tefluthrin is the ISO common name[3] for an organic compound that is used as a pesticide.[1] It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins.[4] It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.[5]

  1. ^ a b Pesticide Properties Database. "Tefluthrin". University of Hertfordshire.
  2. ^ "Tefluthrin". US National Library of Medicine. Retrieved 2020-02-02.
  3. ^ "Compendium of Pesticide Common Names: tefluthrin". BCPC.
  4. ^ Metcalf, Robert L.; Horowitz, Abraham R. (2014). "Insect Control, 1. Fundamentals". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a14_263.
  5. ^ McDonald, E.; Punja, N.; Jutsum, A. R. (1986). "Rationale in the invention and optimization of tefluthrin, a pyrethroid for use in soil". British Crop Protection Conference--Pests and Diseases, Proceedings (1): 199–206.