Fipronil

June 14, 2021
I offer a cautionary tale about pesticide use.
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Image of Fipronil 3D Image of Fipronil

Fipronil is a broad-spectrum insecticide. It disrupts insects’ central nervous systems by blocking chloride channels that are gated by γ-aminobutyric acid (GABA) or glutamate. These receptors are weaker or nonexistent in mammals.

Fipronil has a chiral center at the sulfur atom in the sulfoxide group; the two enantiomers have been isolated and verified. The article of commerce is a racemic mixture of the two.

Fipronil formulations sold worldwide include flea-control products for pets, cockroach traps, and insecticides for agrciultural crops, lawns, golf courses, and the like. But despite its wide range of uses and relative harmlessness toward mammals, fipronil is a significant environmental hazard. It is highly toxic to fish and other waterborne wildlife, birds, and beneficial insects. It has been cited as one of the primary causes of honeybee die-off.

In 2017, fipronil was the culprit in a food-contamination scandal in the Netherlands. Molecule of the Week’s Dutch reader who suggested this molecule provided this narrative:

  • Egg-laying chickens in the Netherlands are plagued by red mites (bloodmites, Dermanyssus gallinae), which cause anemia and reduce egg output.
  • To combat these mites, farmers turned to a tiny company in the Netherlands called Chickfriend. The company offered an effective way to exterminate the mites by fumigation.
  • Chickfriend helped hundreds of chicken farmers get rid of the mites for months.
  • But—it turned out that Chickfriend’s fumigant contained fipronil, which was banned in the Netherlands. Contamination of Dutch eggs, which are sold worldwide, plunged the industry into a tailspin, with estimated damages running into the hundreds of millions of euros.

A recent article in the Dutch newspaper De Stentor chronicles the fipronil scandal, including the subsequent legal fallout and a better way to combat red mites. (Note: The article is in Dutch, but it is easily translated by major Web browsers.)


Fipronil hazard information

Hazard class* Hazard statement
Acute toxicity, oral, category 3 H301—Toxic if swallowed Chemical Safety Warning
Acute toxicity, dermal, category 3 H311—Toxic in contact with skin Chemical Safety Warning
Serious eye damage/eye irritation, category 2A H319—Causes serious eye irritation Chemical Safety Warning
Acute toxicity, inhalation, category 3 H331—Toxic if inhaled Chemical Safety Warning
Specific target organ toxicity, repeated exposure, oral, category 1 H372—Causes damage to organs through prolonged or repeated exposure if swallowed Chemical Safety Warning
Short-term (acute) aquatic hazard, category 1 H400—Very toxic to aquatic life Chemical Safety Warning
Long-term (chronic) aquatic hazard, category 1 H410—Very toxic to aquatic life with long-lasting effects Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals.  
Explanation of pictograms.

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Fipronil 
fast facts

CAS Reg. No. 120068-37-3
SciFinder
nomenclature
1H-Pyrazole-3-carbonitrile, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)
phenyl]-4-[(trifluoromethyl)
sulfinyl]-
Empirical formula C12H4Cl2F6N4OS
Molar mass 437.15 g/mol
Appearance White to yellow powder
Melting point 200.5 ºC
Water solubility 2 mg/L
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