Cyhalothrin

Lambda-cyhalothrin

λ-cyhalothrin (racemic)
Names
IUPAC name
(R)-α-cyano-3-phenoxybenzyl (1S)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
Other names
Cyhalothrine
Identifiers
  • Compounds
  • Lambda: λ-Cyhalothrin
  • (RS)-α-cyano (1RS,3RS): Cyhalothrin
  • Gamma: γ-Cyhalothrin
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.062.209 Edit this at Wikidata
EC Number
  • (RS)-α-cyano (1RS,3RS): 268-450-2
  • Gamma: 616-373-3
RTECS number
  • Lambda: GZ1227780
UNII
UN number 2588
  • Lambda: InChI=1S/2C23H19ClF3NO3/c2*1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h2*3-12,17-18,20H,1-2H3/b2*19-12-/t2*17-,18+,20-/m10/s1
    Key: BFPGVJIMBRLFIR-GUCBCRIZSA-N
  • (RS)-α-cyano (1RS,3RS): InChI=1S/4C23H19ClF3NO3/c4*1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h4*3-12,17-18,20H,1-2H3/b4*19-12-/t2*17-,18+,20-;2*17-,18-,20-/m1010/s1
    Key: OOAOVGPMANECPJ-RWEUCVCFSA-N
  • Gamma: InChI=1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18+,20-/m0/s1
    Key: ZXQYGBMAQZUVMI-GCMPRSNUSA-N
  • Key: ZXQYGBMAQZUVMI-UHFFFAOYSA-N
  • Gamma: CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C(/C(F)(F)F)\Cl)C
Properties[1]
C23H19ClF3NO3
Molar mass 449.85 g·mol−1
Appearance Colourless solid
Density 1.33 g/cm3
Melting point 49.2 °C (120.6 °F; 322.3 K)
Boiling point Decomposes before boiling
0.005 mg/L [20 °C]
Solubility in other solvents Very soluble in hexane, toluene, methanol, acetone
log P 5.5
Acidity (pKa) Not applicable
Pharmacology
QP53AC06 (WHO)
Hazards[2]
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H312, H330, H410
P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 225 °C (437 °F; 498 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyhalothrin (ISO common name[3]) is an organic compound that, in specific isomeric forms, is used as a pesticide.[4] 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 cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.[5]

  1. ^ Pesticide Properties Database. "lambda-Cyhalothrin". University of Hertfordshire.
  2. ^ "[(R)-Cyano-(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate". Retrieved 2020-02-02.
  3. ^ "Compendium of Pesticide Common Names". BCPC.
  4. ^ Pesticide Properties Database. "Cyhalothrin". University of Hertfordshire.
  5. ^ 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.