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. 2023 Aug;30(38):89877-89888.
doi: 10.1007/s11356-023-28571-0. Epub 2023 Jul 17.

Photodegradation of the insecticide fipronil in aquatic environments: photo-dechlorination processes and products

Soichiro Hirashima  1 , Tomoko Amimoto  2 , Yoko Iwamoto  1   3 , Kazuhiko Takeda  4   5
Affiliations

Photodegradation of the insecticide fipronil in aquatic environments: photo-dechlorination processes and products

Soichiro Hirashima et al. Environ Sci Pollut Res Int. 2023 Aug.

Abstract

Fipronil (FIP) is a phenylpyrazole insecticide that, along with neonicotinoid insecticides, is regularly used worldwide. Photodegradation of FIP in aqueous systems is thought mainly to involve the reaction of desulfinylation to give fipronil desulfinyl (FIP-desulfinyl); however, little is known about further degradation reactions. We investigated FIP photodegradation by analyzing photodegradation products by liquid chromatography and liquid chromatography high-resolution tandem mass spectrometry using an Orbitrap instrument. A wide range of products, including dechlorinated compounds, was detected, and the structures were identified. FIP-desulfinyl has previously been found to be an important and persistent FIP photodegradation product; however, we also found that FIP-desulfinyl was photochemically decomposed to a didechlorinated product via a monodechlorinated product. The main photodegradation pathway was probably similar to that of ethiprole, which has a similar skeleton. The photodegradation rate constant was 22.6 times lower for FIP-desulfinyl (0.00372 min-1) than FIP (0.0839 min-1). The photodegradation rate constant was lower for the newly found didechlorinated product (0.001 min-1 or below) than FIP-desulfinyl, suggesting that the product is persistent in aquatic environments and could be an important indicator of long-term FIP contamination.

Keywords: Aquatic environments; Dechlorinated products; High-resolution mass spectrometry; LC-MS/MS; Phenylpyrazole insecticide.

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