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Fipronil information


Fipronil
2D chemical structure of fipronil
3D chemical structure of fipronil
Names
Preferred IUPAC name
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile[1]
Other names
Fipronil
Fluocyanobenpyrazole
Taurus
Termidor
Identifiers
CAS Number
  • 120068-37-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5063 checkY
ChEMBL
  • ChEMBL101326 checkY
ChemSpider
  • 3235 checkY
ECHA InfoCard 100.102.312 Edit this at Wikidata
KEGG
  • D01042 checkY
PubChem CID
  • 3352
UNII
  • QGH063955F checkY
CompTox Dashboard (EPA)
  • DTXSID4034609 Edit this at Wikidata
InChI
  • InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2 checkY
    Key: ZOCSXAVNDGMNBV-UHFFFAOYSA-N checkY
  • InChI=1/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2
    Key: ZOCSXAVNDGMNBV-UHFFFAOYAP
SMILES
  • FC(F)(F)S(=O)c2c(C#N)nn(c1c(Cl)cc(cc1Cl)C(F)(F)F)c2N
Properties
Chemical formula
C12H4Cl2F6N4OS
Molar mass 437.14 g·mol−1
Density 1.477-1.626 g/cm3
Melting point 200.5 °C (392.9 °F; 473.6 K)
Pharmacology
ATCvet code
QP53AX15 (WHO)
Hazards
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Lethal dose or concentration (LD, LC):
LD50 (median dose)
97 mg/kg (rat, oral)
LC50 (median concentration)
0.25 mg/L (rainbow trout, aquatic)
Safety data sheet (SDS) Fipronil
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals.[3] As of 2017, there does not appear to be significant resistance among fleas to fipronil.[4]

Because of its effectiveness on various pests, fipronil is used as the active ingredient in flea control products for pets and home roach baits as well as field pest control for corn, golf courses, and commercial turf. Its widespread use makes its specific effects the subject of considerable attention. Observations on possible harm to humans or ecosystems are ongoing as well as the monitoring of pesticide resistance development.[5]

  1. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  2. ^ "Safety Date Sheet" (PDF). Santa Cruz Biotechnology, Inc. 23 April 2019. SC-201546 - Fipronil. Retrieved 30 October 2023.
  3. ^ Raymond-Delpech, Valérie; Matsuda, Kazuhiko; Sattelle, Benedict M.; Rauh, James J.; Sattelle, David B. (2005). "Ion channels: molecular targets of neuroactive insecticides". Invertebrate Neuroscience. 5 (3–4): 119–133. doi:10.1007/s10158-005-0004-9. ISSN 1354-2516. PMID 16172884. S2CID 12654353.
  4. ^ Todd-Jenkins, Karen (18 June 2017). "Perception Versus Reality: Insecticide Resistance in Fleas". American Veterinarian. 2 (3). Archived from the original on 11 April 2020.{{cite journal}}: CS1 maint: unfit URL (link)
  5. ^ Maddison, Jill E.; Page, Stephen W. (2008). Small Animal Clinical Pharmacology (2nd ed.). Elsevier Health Sciences. p. 229. ISBN 978-0-7020-2858-8.

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Fipronil

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Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking...

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2017 fipronil eggs contamination

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The 2017 fipronil eggs contamination is an incident in Europe and Asia involving the spread of fipronil insecticide which contaminated human-consumed chicken...

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Roach bait

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temperatures for one year. Fipronil is an extremely active molecule and is a potent disruptor of the insect central nervous system. Fipronil bait is more effective...

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Flea treatments

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fipronil, imidacloprid) showed that selamectin reduced larval cat fleas ≥93.5% after 24 h at doses of ≥0.3 μg. In contrast, at 24 h neither fipronil nor...

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Phenylpyrazole insecticides

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adversely impact human health. Examples include: acetoprole ethiprole fipronil flufiprole pyraclofos pyrafluprole pyriprole pyrolan vaniliprole Vidau...

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Colony collapse disorder

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their impacts had occurred. Fipronil is a phenylpyrazole insecticide, with a broad-spectrum systemic mode of action. Fipronil is designed to eliminate insects...

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Ear mite

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MDR1 mutations. A single treatment with a topical formulation containing fipronil, (S)-methoprene, eprinomectin and praziquantel was shown to be efficient...

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Midge

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Michiel Adriaan; Espindola, Evaldo Luiz Gaeta (2021). "Impact of 2,4-D and fipronil on the tropical midge Chironomus sancticaroli (Diptera: Chironomidae)"...

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Insecticide

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susceptibility of rice to planthopper attacks. Phenylpyrazole insecticides, such as fipronil are a class of synthetic insecticides that operate by interfering with...

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Mange

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the same MDR1 dog restrictions apply. Affected cats can be treated with fipronil and milbemycin oxime. Topical 0.01% ivermectin in oil (Acarexx) has been...

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Fluralaner

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L-glutamate-gated chloride channels (GluCls). Potency of fluralaner is comparable to fipronil (a related GABA-antagonist insecticide and acaricide). Fluralaner is being...

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Nosema ceranae

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shown to act in a synergistic fashion with diverse insecticides such as fipronil or neonicotinoids, by increasing the toxicity of pesticides for bees, leading...

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Phenibut

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(+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones...

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Hydramethylnon

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Protection Agency classifies hydramethylnon as a possible human carcinogen. Fipronil, another insecticide used for similar purposes "Hydramethylnon". PubChem...

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Permethrin

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Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime)...

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Selamectin

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(Interceptor) for heartworms, imidacloprid and moxidectin (Advocate), fipronil (Frontline) or lufenuron (Program) for fleas, or the combination milbemycin...

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Baclofen

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(+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones...

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Yellow crazy ant

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784 hectares (1,940 acres) of the island. A very low concentration of fipronil bait (0.1%) was used to control the ants. Monthly monitoring of these baited...

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Eggs as food

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Netherlands, Belgium, and Germany because of contamination with the insecticide fipronil. One of the most common food allergies in infants is eggs. Infants usually...

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Furosemide

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(+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones...

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Cheyletiella

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pesticide appropriate for the affected animal, often an antiflea product. Fipronil works well, especially in cats. Cats can also be treated with a lime sulfur...

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Pesticide toxicity to bees

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use of the neonicotinoids thiamethoxam, clothianidin, and imidacloprid. Fipronil was also banned for use on maize and sunflowers. In 2015, the US Environmental...

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Termite

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United states, application of a soil termiticide with the active ingredient Fipronil, such as Termidor SC or Taurus SC, by a licensed professional, is a common...

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Cockroach

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been proposed as repellents. Poisoned bait containing hydramethylnon or fipronil, and boric acid powder is effective on adults. Baits with egg killers are...

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Boric acid

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Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime)...

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List of veterinary drugs

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antiparasitic - another medication "febantel" is metabolized to fenbendazole fipronil – antiparasitic flumazenil - reversal agent for benzodiazepines flunixin...

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Christmas Island

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the supercolonies that emerged with aerial spraying of the insecticide Fipronil. Radio broadcasts to Christmas Island from Australia include ABC Radio...

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Pyrazole

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pesticides as fungicides, insecticides and herbicides, including fenpyroximate, fipronil, tebufenpyrad and tolfenpyrad. Pyrazole moieties are listed among the highly...

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Pest control

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Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime)...

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