Piperonyl Butoxide

Basic Info

Common NamePiperonyl Butoxide(F05431)
2D Structure
Description

Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. It is a waxy white solid. It is a synergist. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as especially for carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole.

FRCD IDF05431
CAS Number51-03-6
PubChem CID5794
FormulaC19H30O5
IUPAC Name

5-[2-(2-butoxyethoxy)ethoxymethyl]-6-propyl-1,3-benzodioxole

InChI Key

FIPWRIJSWJWJAI-UHFFFAOYSA-N

InChI

InChI=1S/C19H30O5/c1-3-5-7-20-8-9-21-10-11-22-14-17-13-19-18(23-15-24-19)12-16(17)6-4-2/h12-13H,3-11,14-15H2,1-2H3

Canonical SMILES

CCCCOCCOCCOCC1=CC2=C(C=C1CCC)OCO2

Isomeric SMILES

CCCCOCCOCCOCC1=CC2=C(C=C1CCC)OCO2

Synonyms
        
            6-Propylpiperonyl butyl diethylene glycol ether
        
            PIPERONYL BUTOXIDE
        
            51-03-6
        
            Butacide
        
            Butocide
        
            Ethanol butoxide
        
            Pyrenone 606
        
            Piperonylbutoxide
        
            Butyl carbitol 6-propylpiperonyl ether
        
            5-((2-(2-Butoxyethoxy)ethoxy)methyl)-6-propylbenzo[d][1,3]dioxole
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassBenzodioxoles
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzodioxoles
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsBenzodioxole - Benzenoid - Oxacycle - Ether - Dialkyl ether - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Properties

Property NameProperty Value
Molecular Weight338.444
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count13
Complexity312
Monoisotopic Mass338.209
Exact Mass338.209
XLogP3.7
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9596
Human Intestinal AbsorptionHIA+0.9969
Caco-2 PermeabilityCaco2+0.6450
P-glycoprotein SubstrateSubstrate0.6321
P-glycoprotein InhibitorInhibitor0.5818
Non-inhibitor0.6353
Renal Organic Cation TransporterNon-inhibitor0.7887
Distribution
Subcellular localizationMitochondria0.6246
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8946
CYP450 2D6 SubstrateNon-substrate0.7630
CYP450 3A4 SubstrateSubstrate0.5204
CYP450 1A2 InhibitorInhibitor0.6369
CYP450 2C9 InhibitorNon-inhibitor0.6448
CYP450 2D6 InhibitorNon-inhibitor0.6274
CYP450 2C19 InhibitorInhibitor0.6740
CYP450 3A4 InhibitorInhibitor0.7961
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6692
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7002
Non-inhibitor0.7721
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8687
Fish ToxicityHigh FHMT0.9643
Tetrahymena Pyriformis ToxicityHigh TPT0.9929
Honey Bee ToxicityHigh HBT0.6688
BiodegradationNot ready biodegradable0.5463
Acute Oral ToxicityIV0.6268
Carcinogenicity (Three-class)Warning0.5264
Model Value Unit
Absorption
Aqueous solubility-3.9611LogS
Caco-2 Permeability1.2181LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8237LD50, mol/kg
Fish Toxicity0.9234pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8100pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
OatsKorea20ppm
MaizeKorea20ppm

References

TitleJournalDatePubmed ID
Biorational substitution of piperonyl butoxide in organic production:effectiveness of vegetable oils as synergists for pyrethrums.Environ Sci Pollut Res Int2017 Dec 2229273980
Impact of Pesticide Resistance on Toxicity and Tolerance of HostplantPhytochemicals in Amyelois Transitella (Lepidoptera: Pyralidae).J Insect Sci2016 Sep 1227620560
Metabolism of citral, the major constituent of lemongrass oil, in the cabbagelooper, Trichoplusia ni, and effects of enzyme inhibitors on toxicity andmetabolism.Pestic Biochem Physiol2016 Oct27742357
Chronic dietary exposure to pesticide residues and associated risk in the French ELFE cohort of pregnant women.Environ Int2016 Jul-Aug27187793
Sensitive determination of mixtures of neonicotinoid and fungicide residues inpollen and single bumblebees using a scaled down QuEChERS method for exposureassessment.Anal Bioanal Chem2015 Oct26329280
Method for the quantification of current use and persistent pesticides in cowmilk, human milk and baby formula using gas chromatography tandem massspectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2014 Nov 125261753
The involvement of several enzymes in methanol detoxification in Drosophilamelanogaster adults.Comp Biochem Physiol B Biochem Mol Biol2013 Sep23751173
Determination of natural pesticides in fresh fruits using liquidchromatography/mass spectrometry.J AOAC Int2012 Jan-Feb22468366
The involvement of cytochrome P450 monooxygenases in methanol elimination inDrosophila melanogaster larvae.Arch Insect Biochem Physiol2012 Apr22508581
Behavior of pesticides in coffee beans during the roasting process.Shokuhin Eiseigaku Zasshi201223154763
Lipid peroxidation, oxidative stress and acetylcholinesterase in rat brainexposed to organophosphate and pyrethroid insecticides.Food Chem Toxicol2011 Jun21419823
Interactions between detoxification mechanisms and excretion in Malpighian tubules of Drosophila melanogaster.J Exp Biol2011 Feb 121228205
Distribution and mechanism of α-amanitin tolerance in mycophagous Drosophila (Diptera: Drosophilidae).Environ Entomol2011 Dec22217779
Potential of piperonyl butoxide-synergised pyrethrins against psocids(Psocoptera: Liposcelididae) for stored-grain protection.Pest Manag Sci2010 Mar19904714
Laboratory evaluation of verbutin as a synergist of acaricides against larvae of Rhipicephalus (Boophilus) microplus (Acari: Ixodidae).J Econ Entomol2010 Aug20857748
Metabolism of methoxychlor by Cunninghamella elegans ATCC36112.J Agric Food Chem2009 Sep 919691325
Human exposure to insecticide products containing pyrethrins and piperonyl butoxide (2001-2003).Food Chem Toxicol2009 Jul19306908
Aldrin epoxidation and dihydroisodrin hydroxylation as probes of in vivo and in vitro oxidative metabolic capability of some caterpillars.Pest Manag Sci2008 Jun18432628
Dietary transfer of fluoranthene from an estuarine oligochaete (Monopylephorusrubroniveus) to grass shrimp (Palaemonetes pugio): Influence of piperonylbutoxide.Mar Environ Res2007 Mar17081600
Liquid chromatographic determination of N-methyl carbamate pesticide residues at low parts-per-billion levels in eggs.J AOAC Int2006 Jan-Feb16512248