Piperonyl butoxide

Piperonyl butoxide
Identifiers
CAS number 51-03-6 Y
KEGG C18880 N
ChEMBL CHEMBL1201131 N
Jmol-3D images Image 1
Properties
Molecular formula C19H30O5
Molar mass 338.438 g/mol
Density 1.05 g/cm3
Boiling point

180 °C (0.13 kPa)

Hazards
Flash point 170 °C
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa)
Infobox references

Piperonyl butoxide (PBO) is an organic compound used as pesticide synergist, especially for pyrethroids and rotenone. It does not by itself have pesticidal properties. However, when added to insecticide mixtures, typically pyrethrin, pyrethroid, and carbamate insecticides, their potency is increased considerably.[1] It is a semisynthetic derivative of safrole.[2] The exposure of pregnant women to this compound has become a cause for concern.

Mechanism of action

Piperonyl butoxide is a potent inhibitor of cytochrome P450 enzymes, which detoxify insecticides for many pests. Therefore, inhibiting the P450s allows higher unmetabolised systemic concentrations of the insecticide (such as pyrethroid) to remain within the target animal for a longer period.[3]

Safety and toxicity

Its acute oral and dermal toxicity in mammals is low[4] with LD50 of 7,500 to 6,150 mg/kg when orally administered to rats.[2]

A 2011 study found a significant association between piperonyl butoxide in personal air collected during the third trimester of pregnancy and delayed mental development at 36 months. Children who were more highly exposed in personal air samples (≥4.34 ng/m3) scored 3.9 points lower on the Mental Developmental Index than those with lower exposures. The lead researcher stated, "This drop in IQ points is similar to that observed in lead exposure. While perhaps not impacting an individual's overall function, it is educationally meaningful and could shift the distribution of children in the society who would be in need of early intervention services."[5]

References

  1. ^ National Pesticide Information Center - Piperonyl Butoxide General Fact Sheet
  2. ^ a b Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
  3. ^ Moores, G. D., Philippou, D., Borzatta, V., Trincia, P., Jewess, P., Gunning, R., Bingham, G. (2009). "An analogue of piperonyl butoxide facilitates the characterisation of metabolic resistance". Pest Manag. Sci. 65 (2): 150–154. doi:10.1002/ps.1661. PMID 18951417. 
  4. ^ National Pesticide Information Center - Piperonyl Butoxide Technical Fact Sheet
  5. ^ Common Insecticide Used in Homes Associated With Delayed Mental Development of Young Children, ScienceDaily, Feb. 10, 2011