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Fipronil



Fipronil
IUPAC name 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-
(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile
Other names Fipronil
Fluocyanobenpyrazole
Termidor
Identifiers
CAS number 120068-37-3
SMILES ClC1=C(N2N=C(C#N)C(S(C(F)(F)F)=O)=C2N)C(Cl)=CC(C(F)(F)F)=C1
Properties
Molecular formula C12H4Cl2F6N4OS
Molar mass 437.15 g/mol
Density 1.477-1.626 g/cm³
Melting point

200.5 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Fipronil, is a broadspectrum insecticide that disrupts the insect's central nervous system by blocking the passage of chloride ions through the GABA receptor and glutamate receptor (GluCl), inhibitors of the central nervous system. This causes hyperexcitation of contaminated insects' nerves and muscles. Insect specificity of fipronil may come from a better efficacy on GABA receptor but also on the fact that GluCl does not exist in mammals.[1]

Additional recommended knowledge

Fipronil is a slow acting poison, when mixed with a bait it allows the poisoned insect time to return to the colony or haborage. In cockroaches the feces and carcass can contain sufficient residual pesticide to kill others in the same nesting site. In ants, the sharing of the bait among colony members assists in the spreading of the poison through out the colony. With the cascading effect, the projected kill rate is about 95% in 3 days for ants and cockroaches.

Fipronil is used as the active ingredient in Frontline Top Spot at about 9.8% concentration, and is used together with (S)-methoprene (8.8%) in Frontline Plus, a topical flea and tick control commonly used on dogs and cats. It kills adult fleas before they lay eggs.

After a local application, fipronil is slightly absorbed (approx. 15%) through the skin. Low levels of fipronil may be detected in the plasma, with a very high variability between dogs.

It is also the active ingredient of Regent, now marketed by BASF, which also sells Fipronil under the brand name Termidor for use as a conventional barrier treatment for termites and also as a dust to be blown into termite tunnels. In the US, commercial strength ant Fipronil based gels are sold under the MaxForce brand, and the consumer strength is sold under the Combat brand. Agricultural products include Chipco Choice for use against pests of field corn, golf courses and commercial turf.

It acts by binding to an allosteric site of GABAA receptors and GluCl receptor (of the insect), a form of non-competitive inhibition.

Acute oral LD50 (rat) 97 mg/kg
Acute dermal LD50 (rat) >2000 mg/kg

In humans, fipronil poisoning is characterized by vomiting, agitation, and seizures, and can usually be managed through supportive care and early treatment of seizures.[2] This risk may be associated with the withdrawal of the MaxForce tick management product.

In May 2003, the DGAL (Direction Générale de l'Alimentation du ministère de l'Agriculture ) indicated a case of bee mortality observed in Southern France related to Fipronil acute toxicity. Intoxication was linked to defective seed treatment, which generated dust. The seed treatment involved has since been forbidden.[citation needed]

References

  1. ^ Raymond-Delpech V, Matsuda K, Sattelle BM, Rauh JJ, Sattelle DB (2005) Ion channels: molecular targets of neuroactive insecticides. Invert Neurosci: 1-15.
  2. ^ Mohamed F, Senarathna L, Percy A, Abeyewardene M, Eaglesham G, Cheng R, Azher S, Hittarage A, Dissanayake W, Sheriff MH, Davies W, Buckley NA, Eddleston M., Acute human self-poisoning with the N-phenylpyrazole insecticide fipronil--a GABAA-gated chloride channel blocker, J Toxicol Clin Toxicol. 2004;42(7):955-63)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Fipronil". A list of authors is available in Wikipedia.
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