51-03-6 Usage
Description
Piperonyl butoxide (PBO) is a water insoluble colorless to pale
yellow liquid that was developed in the 1940s to increase the
effectiveness of various pesticides. It is currently registered as an
active ingredient in more than 1500 products used for indoor
or outdoor pesticides, including agricultural maintenance of
some food crops.
Chemical Properties
Light Yellow Liquid
Uses
Different sources of media describe the Uses of 51-03-6 differently. You can refer to the following data:
1. Piperonyl butoxide is used as a synergist for pyrethrins and their
synthetic analogues.
2. Insecticide synergist, especially for pyrethroids and rotenone
3. PBO is a pesticide synergist. It is typically added to carbamate,
pyrethrin, pyrethroid, and rotenone pesticides to greatly
enhance their potency. PBO alone does not have pesticidal
properties.
General Description
Pale yellow to light brown liquid with a mild odor and a faint bitter taste.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Piperonyl butoxide can react with oxidizing materials.
Fire Hazard
Piperonyl butoxide is combustible.
Agricultural Uses
Insecticide synergist: A U.S. EPA restricted Use Pesticide (RUP). Not listed for use in EU countries. Piperonyl butoxide is a synergist, i.e., not a pesticide itself, but enhances the properties of other chemicals. It is used with other pesticides such as pyrethrins, pyrethroids, rotenone and carbamates in food and non-food agricultural products, home and garden products, termite and mosquito products, and veterinary pesticide products. It inhibits the insect’s ability to break down an insecticide before it takes effect, thereby prolonging the action, and reduces the necessity for using a stronger formulation.
Trade name
The U.S. EPA lists 7,340 products containing this substance, 1,622 of which are active
Safety Profile
Poison by skin contact.
Moderately toxic by ingestion and
intraperitoneal routes. An experimental
teratogen. Experimental reproductive
effects. Many glycol ether compounds have
dangerous human reproductive effects,
Questionable carcinogen with experimental
tumorigenic data. Mutation data reported.
Combustible when exposed to heat or
flame; can react with oxidizing materials. To
fight fire, use foam, CO2, dry chemical.
When heated to decomDosition it emits
PLATINOL 0 cis-PLATlNUM(II) DIAMMINE-
DICHLORIDE
Environmental Fate
PBO is rapidly degraded (half-life 8 h) in the environment by
photolysis and is metabolized by soil microorganisms. Its
estimated atmospheric half-life is approximately 3 h.
Metabolic pathway
Piperonyl butoxide is used primarily in admixture with pyrethrins and
some of the pyrethroids to enhance and prolong their insecticidal action.
Much of this use is in domestic and industrial situations. Metabolism
studies were conducted soon after its discovery and first use in the 1950s
and 1960s. The main impetus initially was to understand the mode of
action as a synergist. When this was shown to be due to the inhibition of
oxidative metabolism, further studies were conducted to address possible
toxic interactions with other pesticides and drugs in man.
Piperonyl butoxide undergoes rapid photodegradation and microbial
degradation in soil. It is also rapidly metabolised in insects and mammals
by oxidative attack at the methylenedioxy carbon atom and in the side
chain. A comprehensive review by Casida (1970) describes the chemistry,
mode of action and metabolism of piperonyl butoxide and several related
methylenedioxyphenyl compounds. Though published nearly 30 years
ago, the review remains a very useful compilation of a large amount of
information, supported by more than 300 references.
Degradation
Piperonyl butoxide is stable to hydrolysis at pH 5,7 and 9 in sterile buffers
in the dark at 25 °C. It is rapidly degraded in aqueous solution at pH 7 in
sunlight with a DT50 of 8.4 hours (PM). The compound was found to be
relatively stable under a variety of irradiation conditions as a thin film on
glass or in organic solvent (methanol, benzene and cyclohexane). Loss of
the butoxyethoxy side chain was observed to give 5-methyl-6-propyl-l,3-
benzodioxole (2), butoxyethanol (3) and ethanediol (4) (Fishbein and
Gaibel, 1970). These studies did not utilise radiolabelled compound. The
partial pathways are shown in Scheme 1.
Toxicity evaluation
As a synergist, PBO inhibits mixed-function oxidases, including
cytochrome P450, and resistance-associated esterases that allow
insects to degrade an insecticide, allowing enhanced insecticide
efficacy. It does not effectively act as a synergist in mammals.
Check Digit Verification of cas no
The CAS Registry Mumber 51-03-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 51-03:
(4*5)+(3*1)+(2*0)+(1*3)=26
26 % 10 = 6
So 51-03-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O3.C4H10O3/c1-3-5-7-16-10-13-9-15-14(17-11-18-15)8-12(13)6-4-2;5-1-3-7-4-2-6/h8-9H,3-7,10-11H2,1-2H3;5-6H,1-4H2
51-03-6Relevant articles and documents
AN EFFICIENT PROCESS FOR PREPARATION OF ACYL DERIVATIVES OF ALKYLENEDIOXYBENZENES
-
, (2021/08/20)
The present disclosure provides a process of preparation of compounds of Formula I comprising the step of : reacting an alkylenedioxybenzene compound of Formula II with an acyl halide of Formula III in presence of a solvent, wherein the step of reacting the alkylenedioxybenzene compound of Formula II with the acyl halide of Formula III is effected in presence of an amphoteric oxide and a Lewis acid so as to immediately quench the compound of formula H-X, formed during the course of the reaction, to substantially eliminate degradation of the compound of any of Formula I and II. The present disclosure also provides for process(es) for preparation of compound of Formula IVa, IVb and IVc.
Synthetic and mechanistic investigation of piperonyl butoxide from dihydrosafrole
Wang, Shuai,Liu, Jinqiang,Qian, Chao,Chen, Xinzhi
experimental part, p. 147 - 160 (2012/05/20)
Piperonyl butoxide (PBO) 1 was prepared via the successive chloromethylation and etherification of dihydrosafrole 3. In this work, during the chloromethylation of 3, several by-products such as 5 (the isomer of chloromethyldihydrosafrole 4), 6-propylpiperonyl alcohol 6, bis(chloromethyl)- dihydrosafrole 7 and 8, bis(2-propyl-4,5-methylenedioxyphenyl)methane 9 and di(2-propyl-4,5-methy lene-dioxybenzyl)ether 10 were found. However, it was found that 5, 6, 7, and 8 could undergo a further reaction to the final product (PBO), rather than its derivatives, though the by-products 9 and 10 still existed. Based on these results, the plausible mechanism of the chloromethylation and etherification of 3 was proposed. Furthermore, the reliability of the plausible mechanism was verified by quantum chemical calculations using DFT. In addition, the final product (PBO) was produced with a high selectivity and yield by reducing the by-products 9 and 10. Springer Science+Business Media B.V. 2011.
Cyclodextrin inclusion complex of piperonyl butoxide
-
, (2008/06/13)
The invention relates to new inclusion complexes of piperonyl butoxide formed with cyclodextrin. The new complex of the invention can be prepared by reacting cyclodextrin or a solution thereof formed with water and/or an organic solvent having 1-4 carbon atoms, preferably ethanol with piperonyl butoxide or a solution thereof formed with an organic solvent having 1-4 carbon atoms, preferably ethanol at a temperature between 20° C. and 90° C., whereby the piperonyl butoxide is used in an amount of 0.6-1.5 moles related to 1 mole of cyclodextrin. The complexes of the present invention synergize the pesticidal effect of known insecticides and fungicides to a much higher extent of known insecticides and fungicides to a much higher extent than piperonyl butoxide used per se.
