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| | Piperonyl butoxide Basic information |
| | Piperonyl butoxide Chemical Properties |
| Melting point | <25 °C | | Boiling point | 180 °C | | density | 1.059 g/mL at 25 °C(lit.) | | vapor pressure | 0.02 hPa (60 °C) | | refractive index | n20/D 1.498(lit.) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | water: slightly soluble0.0289g/L at 20.4°C | | form | Liquid | | color | Clear yellow | | Specific Gravity | 1.060 (20/4℃) | | Odor | mild odor or odorless | | Water Solubility | <0.1 g/100 mL at 18 ºC | | Merck | 14,7476 | | BRN | 288063 | | Stability: | Stable. Combustible. Incompatible with oxidizing agents. | | InChIKey | HHZWGSFIZRNPFB-UHFFFAOYSA-N | | LogP | 4.750 | | CAS DataBase Reference | 51-03-6(CAS DataBase Reference) | | IARC | 3 (Vol. 30, Sup 7) 1987 | | NIST Chemistry Reference | Piperonyl butoxide(51-03-6) | | EPA Substance Registry System | Piperonyl butoxide (51-03-6) |
| | Piperonyl butoxide Usage And Synthesis |
| 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 | 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. | | Uses | Insecticide synergist, especially for pyrethroids and rotenone | | Uses | Piperonyl butoxide is used as a synergist for pyrethrins and their
synthetic analogues. | | Definition | ChEBI: Piperonyl butoxide is a member of benzodioxoles. It has a role as a pesticide synergist. | | 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. | | 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. | | 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. |
| | Piperonyl butoxide Preparation Products And Raw materials |
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