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 In May 2010 EU Commission withdrawn plant protection products containing bifenthrin.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
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 Feb	9039463
Enantiomer-specific, bifenthrin-induced apoptosis mediated by MAPK signalling pathway in Hep G2 cells.	2009 Jul 10	19442700
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.	2009 Nov	19748519
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009 Oct	20019907
Effects of several pyrethroids on hepatic cytochrome P450 activities in rats.	2010 Apr	20009351
Bifenthrin-induced oxidative stress in human erythrocytes in vitro and protective effect of selected flavonols.	2010 Mar	19833193
Disrupting effects of bifenthrin on ovulatory gene expression and prostaglandin synthesis in rat ovarian granulosa cells.	2011 Mar 28	21251947
Enantioselective endocrine-disrupting effects of bifenthrin on hormone synthesis in rat ovarian cells.	2011 Nov 28	21871944
Correlation of tissue concentrations of the pyrethroid bifenthrin with neurotoxicity in the rat.	2011 Nov 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 Sep	21718662
Reconstitution studies of pesticides and surfactants exploring the cause of estrogenic activity observed in surface waters of the San Francisco Bay Delta.	2012 Aug 21	22881714
Exposure of maternal mice to cis-bifenthrin enantioselectively disrupts the transcription of genes related to testosterone synthesis in male offspring.	2013 Dec	23994515
Enantioselective effect of bifenthrin on antioxidant enzyme gene expression and stress protein response in PC12 cells.	2013 Jul	22718203
Disruption of the hormonal network and the enantioselectivity of bifenthrin in trophoblast: maternal-fetal health risk of chiral pesticides.	2014 Jul 15	24938463
Exposure to bifenthrin causes immunotoxicity and oxidative stress in male mice.	2014 Sep	23172818
Enantioselective disruption of the endocrine system by Cis-Bifenthrin in the male mice.	2015 Jul	24449165

Name

Type

Language

BIFENTHRIN

Common 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

BIFLEX

Brand 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