Enantioselective Bioaccumulation and Toxicity of the Neonicotinoid Insecticide Dinotefuran in Earthworms ( Eisenia fetida)

J Agric Food Chem. 2018 May 2;66(17):4531-4540. doi: 10.1021/acs.jafc.8b00285. Epub 2018 Apr 18.

Abstract

The enantioselective bioaccumulation and toxicity of dinotefuran in earthworms were studied in this study. The results showed that S-dinotefuran accumulated faster than Rac-dinotefuran and R-dinotefuran in earthworms. The acute toxicity of S-dinotefuran was 1.49 and 2.67 times that of the Rac-dinotefuran and R-dinotefuran in artificial soil during 14 days of exposure. At 1.0 mg/kg, the three tested chemicals inhibited the growth and reproduction as well as induced oxidative stress effects in earthworms; however, the toxic effects induced by S-dinotefuran were the most serious. The transcriptome sequencing results showed that S-dinotefuran had stronger interactions to biomacromolecules and influences on the endoplasmic reticulum (ER) than R-dinotefuran, which may be the main reason for enantioselectivities between the two enantiomers. The present results indicated that the risk of S-dinotefuran was higher than that of Rac-dinotefuran and R-dinotefuran in the soil environment to earthworms. Risk assessment of dinotefuran should be evaluated at the enantiomer level.

Keywords: biomarkers; chirality; molecular mechanism; residue analysis; transcriptome sequencing.

MeSH terms

  • Animals
  • Guanidines / chemistry
  • Guanidines / pharmacokinetics*
  • Guanidines / toxicity*
  • Insecticides*
  • Neonicotinoids / chemistry
  • Neonicotinoids / pharmacokinetics*
  • Neonicotinoids / toxicity*
  • Nitro Compounds / chemistry
  • Nitro Compounds / pharmacokinetics*
  • Nitro Compounds / toxicity*
  • Oligochaeta / drug effects*
  • Oligochaeta / metabolism*
  • Soil / chemistry
  • Soil Pollutants / pharmacokinetics
  • Soil Pollutants / toxicity
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Guanidines
  • Insecticides
  • Neonicotinoids
  • Nitro Compounds
  • Soil
  • Soil Pollutants
  • dinotefuran