Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H30O5 |
Molecular Weight | 338.4385 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCOCCOCCOCC1=CC2=C(OCO2)C=C1CCC
InChI
InChIKey=FIPWRIJSWJWJAI-UHFFFAOYSA-N
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
Molecular Formula | C19H30O5 |
Molecular Weight | 338.4385 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. It is a waxy white solid. It is a semisynthetic derivative of safrole. It is used for the treatment of head, pubic (crab), and body lice. Piperonyl butoxide is a synergist. It has no pesticidal activity of its own, but acts to increase the activity of pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. PBO acts as an insecticide synergist by inhibiting the natural defense mechanisms of the insect, the most important of which is the Mixed Function Oxidase system, also known as the cytochrome P-450 system. The MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides like pyrethrins and the synthetic pyrethroids - thus when PBO is added, higher insecticide levels remain in the insect to exercise their lethal effect. An important consequence of this property is that, by enhancing the activity of a given insecticide, less may be used to achieve the same result. PBO does not appear to have a significant effect on the MFO system in humans. Skin Sensitization PBO has a low acute toxicity by oral, inhalation and dermal routes. It is minimally irritating to the eyes and skin. It is a not a dermal sensitizer. No evidence suggests that PBO disrupts the normal functioning of the endocrine system. This includes the recently developed data to assess the possible interaction of PBO with the endocrine system.
Approval Year
T1/2
Value | Dose | Co-administered | Analyte | Population |
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24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17162471/ |
500 mg/kg single, oral dose: 500 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PIPERONYL BUTOXIDE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Susceptibility of populations of Banks grass mites (Acari: Tetranychidae) suspected of developing bifenthrin resistance from three maize fields. | 2002 |
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Characterization of resistance to clofentezine in populations of European red mite from orchards in Ontario. | 2002 |
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Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals. | 2002 Dec |
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Efficacy of ethiprole applied alone and in combination with conventional insecticides for protection of stored wheat and stored corn. | 2002 Dec |
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Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae) control in intensive animal units in the United Kingdom. | 2002 Dec |
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Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products. | 2002 Dec |
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Fenbendazole pharmacokinetics, metabolism, and potentiation in horses. | 2002 Nov |
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Effects of iprodione and fludioxonil on glycerol synthesis and hyphal development in Candida albicans. | 2002 Oct |
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Near UV quantum yields for rotenone and piperonyl butoxide. | 2002 Oct |
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Efficacy of the organic-certified insecticide Diatect II against the boll weevil (Anthonomus grandis) in cotton. | 2002 Oct |
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The in vivo pediculicidal efficacy of a natural remedy. | 2002 Oct |
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Oxidation of dibenzo- p-dioxin, dibenzofuran, biphenyl, and diphenyl ether by the white-rot fungus Phlebia lindtneri. | 2002 Oct |
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Scabies and pediculosis pubis: an update of treatment regimens and general review. | 2002 Oct 15 |
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Insecticide susceptibilities of cat fleas (Siphonaptera: Pulicidae) from several regions of the United States. | 2002 Sep |
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Suppression of bloodfeeding by Ochlerotatus dorsalis and Ochlerotatus melanimon on cattle treated with python ear tags. | 2002 Sep |
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Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia. | 2003 Apr |
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Action of pyrethrum-based formulations against grain weevils. | 2003 Apr 30 |
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Isocratic reversed-phase liquid chromatographic method for the simultaneous determination of (S)-methoprene, MGK264, piperonyl butoxide, sumithrin and permethrin in pesticide formulation. | 2003 Jan 3 |
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Efficacy and tolerability of natural synergised pyrethrins in a new thermo labile foam formulation in topical treatment of scabies: a prospective, randomised, investigator-blinded, comparative trial vs. permethrin cream. | 2003 Jan-Feb |
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Resistance to coumaphos and diazinon in Boophilus microplus (Acari: Ixodidae) and evidence for the involvement of an oxidative detoxification mechanism. | 2003 Jul |
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Analysis of protein induction in the CNS of SJL mice with experimental allergic encephalomyelitis by proteomic screening and immunohistochemistry. | 2003 Jul |
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Biotransformation and bioconcentration of pyrene in Daphnia magna. | 2003 Jun 19 |
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Mechanisms of resistance to DDT and pyrethroids in Patagonian populations of Simulium blackflies. | 2003 Mar |
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Reproductive and neurobehavioural effects of piperonyl butoxide administered to mice in the diet. | 2003 Mar |
|
Direct on-line continuous supercritical fluid extraction and HPLC of aqueous pyrethrins solutions. | 2003 Mar 15 |
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Biodegradation of chloronaphthalenes and polycyclic aromatic hydrocarbons by the white-rot fungus Phlebia lindtneri. | 2003 May |
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Bioconcentration and acute toxicity of polycyclic musks in two benthic organisms (Chironomus riparius and Lumbriculus variegatus). | 2003 May |
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Oxidative stress in laboratory-incubated double-crested cormorant eggs collected from the Great Lakes. | 2003 Nov |
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Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. | 2003 Nov 19 |
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Effect of horn fly and internal parasite control on growth of beef heifers. | 2003 Nov 28 |
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Ecotoxicologic impacts of agricultural drain water in the Salinas River, California, USA. | 2003 Oct |
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Phthalates, alkylphenols, pesticides, polybrominated diphenyl ethers, and other endocrine-disrupting compounds in indoor air and dust. | 2003 Oct 15 |
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Optimizing an aerial spray for mosquito control. | 2003 Sep |
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Mechanisms of TCDD-induced abnormalities and embryo lethality in white leghorn chickens. | 2003 Sep |
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Oxidative stress in liver and brain of the hatchling chicken (Gallus domesticus) following in ovo injection with TCDD. | 2003 Sep |
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Pyrethroid tolerance in Culex pipiens pipiens var molestus from Marin County, California. | 2004 Apr |
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The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia. | 2004 Aug |
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Teratogenesis in Fundulus heteroclitus embryos exposed to a creosote-contaminated sediment extract and CYP1A inhibitors. | 2004 Aug-Dec |
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Responses of Corcyra cephalonica (Stainton) to pirimiphos-methyl, spinosad, and combinations of pirimiphos-methyl and synergized pyrethrins. | 2004 Feb |
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Role of piperonyl butoxide in the toxicity of chlorpyrifos to Ceriodaphnia dubia and Xenopus laevis. | 2004 Feb |
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Pyrethrins and piperonyl butoxide adsorption to soil organic matter. | 2004 Jan |
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Toxaphene detoxification and acclimation in Daphnia magna: do cytochrome P-450 enzymes play a role? | 2004 Jan |
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Frequency of kdr gene in house fly field populations: correlation of pyrethroid resistance and kdr frequency. | 2004 Jun |
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Diagnostic dose of synergized d-phenothrin for insecticide susceptibility testing by bottle bioassay. | 2004 Jun |
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Development of a novel self-medicating applicator for control of internal and external parasites of wild and domestic animals. | 2004 Mar |
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Detection and characterization of amitraz resistance in the southern cattle tick, Boophilus microplus (Acari: Ixodidae). | 2004 Mar |
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Videodermatoscopy enhances the ability to monitor efficacy of scabies treatment and allows optimal timing of drug application. | 2004 Mar |
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Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae). | 2004 May |
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Preliminary evidence of the role of hydrogen peroxide in the degradation of benzo[a]pyrene by a non-white rot fungus Fusarium solani. | 2004 May |
|
Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives. | 2004 May 15 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10414782
S-bioallethrin and PIPERONYL BUTOXIDE (PBO) caused inhibition of lymphocyte proliferation (MTT-test) after a 72-h culture period in a concentration dependent manner.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:21:11 UTC 2023
by
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on
Fri Dec 15 15:21:11 UTC 2023
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Record UNII |
LWK91TU9AH
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C45187
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CFR |
21 CFR 358.610
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EPA PESTICIDE CODE |
67501
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IARC | Piperonyl butoxide |
Code System | Code | Type | Description | ||
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LWK91TU9AH
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D010882
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1755
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CHEMBL1201131
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SUB14893MIG
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LWK91TU9AH
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51-03-6
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8345
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100000091753
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8401
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DTXSID1021166
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200-076-7
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DB09350
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m8859
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C29849
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PIPERONYL BUTOXIDE
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4276
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piperonyl butoxide
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5794
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