BIFENTHRIN

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H22ClF3O2
Molecular Weight	422.868
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C=CC=C1COC(=O)[C@@H]2[C@H](\C=C(/Cl)C(F)(F)F)C2(C)C)C3=CC=CC=C3

InChI

InChIKey=OMFRMAHOUUJSGP-IRHGGOMRSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/Bifenthrin_SERA-056-12-02C.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28815728 | http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Evaluation10/Bifenthrin.pdf

Bifenthrin is a pyrethroid insecticide used in urban and agricultural applications. Bifenthrin is a broad-spectrum insecticide that modifies voltage-gated ion channels disrupting the normal function of nerve cells. In May 2010 EU Commission withdrawn plant protection products containing bifenthrin.

Approval Year

PubMed

Title	Date	PubMed
Enantioselective disruption of the endocrine system by Cis-Bifenthrin in the male mice.	2015-07	24449165
Exposure to bifenthrin causes immunotoxicity and oxidative stress in male mice.	2014-09	23172818
Disruption of the hormonal network and the enantioselectivity of bifenthrin in trophoblast: maternal-fetal health risk of chiral pesticides.	2014-07-15	24938463
Exposure of maternal mice to cis-bifenthrin enantioselectively disrupts the transcription of genes related to testosterone synthesis in male offspring.	2013-12	23994515
Enantioselective effect of bifenthrin on antioxidant enzyme gene expression and stress protein response in PC12 cells.	2013-07	22718203
Reconstitution studies of pesticides and surfactants exploring the cause of estrogenic activity observed in surface waters of the San Francisco Bay Delta.	2012-08-21	22881714
Enantioselective endocrine-disrupting effects of bifenthrin on hormone synthesis in rat ovarian cells.	2011-11-28	21871944
Correlation of tissue concentrations of the pyrethroid bifenthrin with neurotoxicity in the rat.	2011-11-28	21854826
Changes in gene transcription and whole organism responses in larval fathead minnow (Pimephales promelas) following short-term exposure to the synthetic pyrethroid bifenthrin.	2011-09	21718662
Disrupting effects of bifenthrin on ovulatory gene expression and prostaglandin synthesis in rat ovarian granulosa cells.	2011-03-28	21251947
Integrative assessment of enantioselectivity in endocrine disruption and immunotoxicity of synthetic pyrethroids.	2010-05	20097460
Effects of several pyrethroids on hepatic cytochrome P450 activities in rats.	2010-04	20009351
Bifenthrin-induced oxidative stress in human erythrocytes in vitro and protective effect of selected flavonols.	2010-03	19833193
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.	2009-11	19748519
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009-10	20019907
Enantiomer-specific, bifenthrin-induced apoptosis mediated by MAPK signalling pathway in Hep G2 cells.	2009-07-10	19442700
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009-05-15	19249324
Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Na v 1.8 sodium channels expressed in Xenopus oocytes.	2006-03-15	16051293
Relationship between toxicity of selected insecticides and expression of stress proteins (HSP, GRP) in cultured human cells: effects of commercial formulations versus pure active molecules.	2006-01	16271832
Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes.	2004-07-09	15123619
Increasing or decreasing nervous activity modulates the severity of the glio-vascular lesions of 1,3-dinitrobenzene in the rat: effects of the tremorgenic pyrethroid, Bifenthrin, and of anaesthesia.	1997-02	9039463

Name

Type

Language

BIFENTHRIN

Common Name

English

BIFLEX

Preferred Name

English

BIPHENTHRIN

Common Name

English

CAPTURE

Brand Name

English

TALSTAR

Brand Name

English

CYCLOPROPANECARBOXYLIC ACID, 3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYL-, (2-METHYL(1,1'-BIPHENYL)-3-YL)METHYL ESTER, (1.ALPHA.,3.ALPHA.(Z))-(±)-

Common Name

English

BIFENTHRIN [ISO]

Common Name

English

BIFENTHRIN [HSDB]

Common Name

English

BIPHENATE

Common Name

English

ONYX

Brand Name

English

WISDOM

Brand Name

English

2-METHYLBIPHENYL-3-YLMETHYL-(Z)-(1RS)-CIS-3-(2-CHLORO-3,3,3-TRIFLUOROPROP-1-ENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Common Name

English

EMPOWER

Brand Name

English

FMC 54800

Code

English

BIFENTHRIN [MI]

Common Name

English

BIPHENTRIN

Common Name

English

FMC-54800

Common Name

English

(1.ALPHA.,3.ALPHA.(Z))-(±)-3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID (2-METHYL(1,1'-BIPHENYL)-3-YL)METHYL ESTER

Common Name

English

BRIGADE

Brand Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

128825