An internal standard for the quantification of bifenthrin
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Unlabeled Version(s)
24057Bifenthrin
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Bifenthrin-d5

Item No. 39588

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3R)-rel-3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propen-1-yl]-2,2-dimethyl-cyclopropanecarboxylic acid, (2-methyl[1,1'-biphenyl-2′,3′,4′,5′,6′-d5]-3-yl)methyl ester
Synonyms
  • (±)-Bifenthrin-d5
Molecular Formula
C23H17ClD5F3O2
Formula Weight
427.9
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleDMSO: slightly soluble
SMILES
CC([C@@H]1C(OCC2=C(C)C(C3=C([2H])C([2H])=C([2H])C([2H])=C3[2H])=CC=C2)=O)([C@H]1/C=C(C(F)(F)F)\Cl)C
InChi Code
InChI=1S/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12-/t18-,20-/m0/s1/i4D,5D,6D,8D,9D
InChi Key
OMFRMAHOUUJSGP-OKWLEVHWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $325

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    Product Description

    Bifenthrin-d5 is intended for use as an internal standard for the quantification of bifenthrin (Item No. 24057) by GC- or LC-MS. Bifenthrin is a synthetic pyrethroid insecticide and a slow activator of voltage-gated sodium channel 1.8 (Nav1.8).1 It is toxic to A. gambiae and C. quinquefasciatus mosquitos (LD50s = 0.15 and 0.16 ng/mg, respectively) and reduces the number of insidious flower bugs (O. insidiosus) in corn when applied at a concentration of 168 g/ha.2,3 Bifenthrin is toxic to D. magna (LC50 = 12.4 µg/L) and inhibits D. magna reproduction when used at a concentration of 1 µg/L.4 It induces fine- and whole-body tremors and decreases motor activity in rats when administered at a dose of 20 mg/kg.5 Bifenthrin (8 mg/kg) decreases body mass and locomotor activity, increases memory deficits in the passive avoidance test, as well as decreases the concentration of blood erythrocytes, increases lymphocyte hepatic infiltration, and increases the activity of hepatic alanine transaminase (ALT) in mice.6 Formulations containing bifenthrin have been used as insecticides in residential and agricultural settings.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Choi, J.S., and Soderlund, D.M. Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Nav1.8 sodium channels expressed in Xenopus oocytes. Toxicol. Appl. Pharmacol. 211(3), 233-244 (2006).

    2. Hougard, J.-M., Duchon, S., Zaim, M., et al. Bifenthrin: A useful pyrethroid insecticide for treatment of mosquito nets. J. Med. Entomol. 39(3), 526-533 (2002).

    3. Al-Deeb, M.A., Wilde, G.E., and Zhu, K.Y. Effect of insecticides used in corn, sorghum, and alfalfa on the predator Orius insidiosus (Hemiptera: Anthocoridae). J. Econ. Entomol. 94(6), 1353-1360 (2001).

    4. Ye, W.H., Wen, Y.Z., Liu, W.P., et al. Effects of bifenthrin on Daphnia magna during chronic toxicity test and the recovery test. J. Environ. Sci. (China) 16(5), 843-846 (2004).

    5. Wolansky, M.J., McDaniel, K.L., Moser, V.C., et al. Influence of dosing volume on the neurotoxicity of bifenthrin. Neurotoxicol. Teratol. 29(3), 377-384 (2007).

    6. Nieradko-Iwanicka, B., Borzecki, A., and Jodlowska-Jedrych, B. Effect of subacute poisoning with bifenthrin on locomotor activity, memory retention, haematological, biochemical and histopathological parameters in mice. J. Physiol. Pharmacol. 66(1), 129-137 (2015).