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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20Cl2O3
Molecular Weight 391.288
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIOPERMETHRIN

SMILES

CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2

InChI

InChIKey=RLLPVAHGXHCWKJ-MJGOQNOKSA-N
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H20Cl2O3
Molecular Weight 391.288
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus.
1993 Jul
Purification and characterization of trans-permethrin metabolizing microsomal esterases from workers of the eastern subterranean termite, Reticulitermes flavipes (Kollar).
2001 Apr 27
Increased ErbB-2 tyrosine kinase activity, MAPK phosphorylation, and cell proliferation in the prostate cancer cell line LNCaP following treatment by select pesticides.
2001 Mar
Simultaneous determination of chlorpyrifos, permethrin, and their metabolites in rat plasma and urine by high-performance liquid chromatography.
2001 May-Jun
A solid phase extraction reversed-phase HPLC method for the simultaneous determination of methoprene, permethrin and selected metabolites in rat plasma and urine.
2001 Nov
Neonatal exposure of newborn mice to pyrethroid (permethrin) represses activity-dependent c-fos mRNA expression in cerebellum.
2002 Jul
Residential pesticide use during pregnancy among a cohort of urban minority women.
2002 May
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
2003 Nov-Dec
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
2004 Apr
Determination of solid-liquid partition coefficients (K(d)) for diazinon, propetamphos and cis-permethrin: implications for sheep dip disposal.
2004 Aug 15
Determination of enantiomers of synthetic pyrethroids in water by solid phase microextraction - enantioselective gas chromatography.
2004 Feb 25
Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes.
2004 Jul 9
Effectiveness of residual spraying of peridomestic ecotopes with deltamethrin and permethrin on Triatoma infestans in rural western Argentina: a district-wide randomized trial.
2004 Mar
Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.
2005
Diffusion of the synthetic pyrethroid permethrin into bed-sediments.
2005 Jan 15
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).
2005 Jun 9
Rapid analysis of pyrethroids in whole urine by high-performance liquid chromatography using a monolithic column and off-line preconcentration in a restricted access material cartridge.
2005 May
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005 Oct
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.
2006 Feb 28
Laboratory and scaled up evaluation of cis-permethrin applied as a new ultra low volume formulation against Aedes aegypti (Diptera: Culicidae).
2006 Jan
An intervention to reduce residential insecticide exposure during pregnancy among an inner-city cohort.
2006 Nov
Enantiomeric differences in permethrin degradation pathways in soil and sediment.
2006 Nov 29
Method of analysis of a selected group of pyrethroids in soil samples using off-line flow-through extraction and on-column direct large-volume injection in reversed phase high performance liquid chromatography.
2006 Sep
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.
2007 Aug
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.
2007 Jul
An observational study of 127 preschool children at their homes and daycare centers in Ohio: environmental pathways to cis- and trans-permethrin exposure.
2007 Jun
The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats.
2007 Jun 25
Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.
2007 Mar
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.
2007 May 15
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.
2007 Oct
Changes in pest infestation levels, self-reported pesticide use, and permethrin exposure during pregnancy after the 2000-2001 U.S. Environmental Protection Agency restriction of organophosphates.
2008 Dec
Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome.
2008 Dec 30
Multimedia measurements and activity patterns in an observational pilot study of nine young children.
2008 Jan
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.
2008 Jun 27
Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California.
2008 Mar-Apr
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.
2008 Mar-Apr
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.
2009
Design of a compressed air modulator to be used in comprehensive multidimensional gas chromatography and its application in the determination of pesticide residues in grapes.
2009 Apr 10
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.
2009 Aug
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009 Jan
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.
2009 Jan
Evidence for dose-additive effects of pyrethroids on motor activity in rats.
2009 Oct
Time-dependent integrity during storage of natural surface water samples for the trace analysis of pharmaceutical products, feminizing hormones and pesticides.
2010 Apr 19
In vitro dermal absorption of pyrethroid pesticides in human and rat skin.
2010 Jul
Distribution and determinants of pesticide mixtures in cord serum using principal component analysis.
2010 Jul 15
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.
2010 May
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011 Sep 14
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:59:00 GMT 2025
Edited
by admin
on Mon Mar 31 19:59:00 GMT 2025
Record UNII
5O0SBK88B7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NRDC-147
Preferred Name English
BIOPERMETHRIN
ISO  
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-, (3-PHENOXYPHENYL)METHYL ESTER, (1R,3S)-
Systematic Name English
CYCLOPROPANECARBOXYLIC ACID, 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-, (3-PHENOXYPHENYL)METHYL ESTER, (1R-TRANS)-
Systematic Name English
(+)-TRANS-PERMETHRIN
Common Name English
1R,TRANS-PERMETHRIN
Common Name English
PERMETHRIN, TRANS-(+)-
Common Name English
RU-22090
Code English
BIOPERMETHRIN [ISO]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID8058116
Created by admin on Mon Mar 31 19:59:00 GMT 2025 , Edited by admin on Mon Mar 31 19:59:00 GMT 2025
PRIMARY
CAS
51877-74-8
Created by admin on Mon Mar 31 19:59:00 GMT 2025 , Edited by admin on Mon Mar 31 19:59:00 GMT 2025
PRIMARY
ALANWOOD
biopermethrin
Created by admin on Mon Mar 31 19:59:00 GMT 2025 , Edited by admin on Mon Mar 31 19:59:00 GMT 2025
PRIMARY
FDA UNII
5O0SBK88B7
Created by admin on Mon Mar 31 19:59:00 GMT 2025 , Edited by admin on Mon Mar 31 19:59:00 GMT 2025
PRIMARY
PUBCHEM
43859
Created by admin on Mon Mar 31 19:59:00 GMT 2025 , Edited by admin on Mon Mar 31 19:59:00 GMT 2025
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER