Agriculture

Synergistic effect of piperonyl butoxide and emamectin benzoate on enzymatic activities in resistant populations of red flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae).
Awan DA, Ahmad F, Saleem MA, Shakoori AR.
Environ Sci Pollut Res Int. 2019 May;26(14):14200-14213. doi: 10.1007/s11356-019-04812-z. Epub 2019 Mar 12.

Piperonyl butoxide (PBO) combined with pyrethroids in insecticide-treated nets to prevent malaria in Africa.
Gleave K, Lissenden N, Richardson M, Choi L, Ranson H.
Cochrane Database Syst Rev. 2018 Nov 29;11:CD012776. doi: 10.1002/14651858.CD012776.pub2.

Do bednets including piperonyl butoxide offer additional protection against populations of Anopheles gambiae s.l. that are highly resistant to pyrethroids? An experimental hut evaluation in Burkina Fasov.
Toe KH, Müller P, Badolo A, Traore A, Sagnon N, Dabiré RK, Ranson H.
Med Vet Entomol. 2018 Dec;32(4):407-416. doi: 10.1111/mve.12316. Epub 2018 Jul 11

Effectiveness of a long-lasting piperonyl butoxide-treated insecticidal net and indoor residual spray interventions, separately and together, against malaria transmitted by pyrethroid-resistant mosquitoes: a cluster, randomised controlled, two-by-two factorial design trial.
Protopopoff N, Mosha JF, Lukole E, Charlwood JD, Wright A, Mwalimu CD, Manjurano A, Mosha FW, Kisinza W, Kleinschmidt I, Rowland M.
Lancet. 2018 Apr 21;391(10130):1577-1588. doi: 10.1016/S0140-6736(18)30427-6. Epub 2018 Apr 11.

Discovery of novel piperonyl derivatives as diapophytoene desaturase inhibitors for the treatment of methicillin-, vancomycin- and linezolid-resistant Staphylococcus aureus infections.
Wei H, Mao F, Ni S, Chen F, Li B, Qiu X, Hu L, Wang M, Zheng X, Zhu J, Lan L, Li J.
Eur J Med Chem. 2018 Feb 10;145:235-251. doi: 10.1016/j.ejmech.2017.12.090. Epub 2017 Dec 29.

Biorational substitution of piperonyl butoxide in organic production: effectiveness of vegetable oils as synergists for pyrethrums.
Marchand PA, Dimier-Vallet C, Vidal R.
Environ Sci Pollut Res Int. 2018 Oct;25(30):29936-29942. doi: 10.1007/s11356-017-1057-0. Epub 2017 Dec 22.

Synergists action of piperonyl butoxide and S,S,S-tributyl phosphorotrithioate on toxicity of carbamate insecticides against Blattella germanica.
Sanei Dehkordi A, Salim Abadi Y, Nasirian H, Hazratian T, Gorouhi MA, Yousefi S, Paksa A.
Asian Pac J Trop Med. 2017 Oct;10(10):981-986. doi: 10.1016/j.apjtm.2017.09.010. Epub 2017 Sep 18.

Use of the synergist piperonyl butoxide can slow the development of alpha-cypermethrin resistance in the whitefly Bemisia tabaci.
Zimmer CT, Panini M, Singh KS, Randall EL, Field LM, Roditakis E, Mazzoni E, Bass C.
Insect Mol Biol. 2017 Apr;26(2):152-163. doi: 10.1111/imb.12276. Epub 2016 Nov 21.

Safety

Long-term exposure to cypermethrin and piperonyl butoxide cause liver and kidney inflammation and induce genotoxicity in New Zealand white male rabbits.
Vardavas AI, Stivaktakis PD, Tzatzarakis MN, Fragkiadaki P, Vasilaki F, Tzardi M, Datseri G, Tsiaoussis J, Alegakis AK, Tsitsimpikou C, Rakitskii VN, Carvalho F, Tsatsakis AM.
Food Chem Toxicol. 2016 Aug;94:250-9. doi: 10.1016/j.fct.2016.06.016. Epub 2016 Jun 16.

Piperonil butoxide (6- (10-Hydroxydecanoyl) -2,3-dimethoxy-5-methylphenol) is a chemical compound co-formulant with a protective and synergistic function of commercial insecticidal products based on pyrethrin.

The name defines the structure of the molecule:

• Piperonyl is derived from piperic acid, an organic compound found in the plant species Piper nigrum (black pepper). The 'onyl' part indicates a ketone group attached to the molecule.
• Butoxide ndicates the presence of a butyl group (a chain of four carbons) and an oxide group in the molecule.

The synthesis of piperonyl butoxide involves different steps:

• Preparation of piperonal. Piperonal, also known as heliotropin, can be synthesised from safrole or isosafrole, organic compounds that occur naturally in various plants.
• Reaction with chloroacetone. Piperonal is reacted with chloroacetone to form a compound known as piperonylacetone.
• Reaction with sodium methoxide. Piperonylacetone is reacted with sodium methoxide to open the methylenedioxy bridge.
• Reaction with 2,3-dibromobutane The resulting compound is reacted with 2,3-dibromobutane to form piperonyl butoxide.

What it is for and where

Cosmetics

Skin protectant. It creates a protective barrier on the skin to defend it from harmful substances, irritants, allergens, pathogens that can cause various inflammatory conditions. These products can also improve the natural skin barrier and in most cases more than one is needed to achieve an effective result.

It is used in some countries in organic farming, while in others it is not allowed.

Piperonil butoxide function is to lengthen the effectiveness time of insecticides.

Piperonil butoxide studies

• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.444 g/mol
• UNII: LWK91TU9AH
• CAS: 51-03-6  12750-92-4  63993-73-7
• EC Number: 200-076-7
• PubChem Substance ID 24857511
• MDL number MFCD00005842
• Beilstein Registry Number 288063

Sinonimi:

• Butacide
• Butocide
• Ethanol butoxide
• 2-(2-Butoxyethoxy)ethyl 6-propylpiperonyl ether
• Pyrenone 606
• 6-(Propylpiperonyl)butylcarbityl ether
• Piperonylbutoxide
• (Butylcarbityl)(6-propylpiperonyl)ether
• 1,3-Benzodioxole, 5-[[2-(2-butoxyethoxy)ethoxy]methyl]-6-propyl-
• 3,4-Methylenedioxy-6-propylbenzyl n-butyl diethyleneglycol ether
• 6-Propylpiperonyl butyl diethylene glycol ether
• 6-(Propylpiperonyl)-butyl carbityl ether
• 1,3-Benzodioxole, 5-((2-(2-butoxyethoxy)ethoxy)methyl)-6-propyl-
• 5-Propyl-4-(2,5,8-trioxa-dodecyl)-1,3-benzodioxole
• Butylcarbityl (6-propylpiperonyl) ether
• 3,4-Methylenedioxy-6-propylbenzyl n-butyldiethyleneglycol ether
• 5-[2-(2-Butoxyethoxy)ethoxymethyl]-6-propyl-1,3-benzodioxole
• 5-Propyl-4-(2,5,8-trioxa-dodecyl)-1,3-benzodioxol [German]
• 5-((2-(2-Butoxyethoxy)ethoxy)methyl)-6-propyl-1,3-benzodioxole
• 5-{[2-(2-butoxyethoxy)ethoxy]methyl}-6-propyl-1,3-benzodioxole
• (3,4-Methylenedioxy-6-propylbenzyl) (butyl) diethylene glycol ether
• 3,4-Methylendioxy-6-propylbenzyl-n-butyl-diaethylenglykolaether [German]
• alpha-(2-(2-Butoxyethoxy)ethoxy)-4,5-methylenedioxy-2-propyltoluene
• .alpha.(2-(2-Butoxyethoxy)ethoxy)-4,5-methylenedioxy-2-propyltoluene
• .alpha.-(2-(2-n-Butoxyethoxy)-ethoxy)-4,5-methylenedioxy-2-propyltoluene
• .alpha.-[2-(2-N-Butoxyethoxy)-ethoxy]-4,5-methylenedioxy-2-propyltoluene
• .alpha.[2-(2-Butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene
• alpha-(2-(2-n-Butoxyethoxy)-ethoxy)-4,5-methylenedioxy-2-propyltoluene
• Butyl-carbityl (6-propylpiperonyl) ether
• 3,4-Methylendioxy-6-propylbenzyl-n-butyl-diaethylenglykolaether
• 5-((2-(2-Butoxyethoxy)ethoxy)methyl)-6-propylbenzo[d][1,3]dioxole
• Butyl carbitol 6-propylpiperonyl ether