Enantioselective Toxicity and Potential Endocrine-Disruptive Effects of the Insecticides Flufiprole and Ethiprole on Danio rerio

J Agric Food Chem. 2024 Jan 24;72(3):1509-1515. doi: 10.1021/acs.jafc.3c07896. Epub 2024 Jan 8.

Abstract

Phenylpyrazole insecticides are widely used as chiral pesticides. However, the enantioselective toxicity and potential endocrine-disrupting effects of these insecticides on aquatic organisms remain unclear. Herein, the enantioselective toxicity and potential endocrine-disrupting effects of flufiprole and ethiprole were investigated by using zebrafish embryos/larvae as a model. The acute toxicity of R-flufiprole and R-ethiprole toward zebrafish embryos and larvae was 1.8-3.1-fold higher than that of the S-configuration. Additionally, R-flufiprole and R-ethiprole had a greater effect on the expression of genes related to the hypothalamus-pituitary-gonad axis in zebrafish compared with the S-configuration. Nevertheless, both S-flufiprole and S-ethiprole exhibited a greater interference effect on the expression of genes related to the hypothalamus-pituitary-thyroid axis and a greater teratogenic effect on zebrafish than the R-configuration. Thus, this study demonstrates that both flufiprole and ethiprole exhibit enantioselective acute toxicity and developmental toxicity toward zebrafish. Furthermore, those pesticides potentially possess enantioselective endocrine-disrupting effects.

Keywords: enantioselectivity; endocrine-disruptive effects; ethiprole; flufiprole; toxicity.

MeSH terms

  • Animals
  • Insecticides* / metabolism
  • Larva
  • Pesticides* / metabolism
  • Pyrazoles*
  • Stereoisomerism
  • Water Pollutants, Chemical* / metabolism
  • Zebrafish / metabolism

Substances

  • Insecticides
  • ethiprole
  • 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(N-(2-methylprop-2-enyl)amino)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
  • Pesticides
  • Water Pollutants, Chemical
  • Pyrazoles