3-Chloro-5-trifluoromethylpyridine-2-carboxylic acid, a Metabolite of the Fungicide Fluopyram, Causes Growth Disorder in Vitis vinifera

J Agric Food Chem. 2019 Jul 3;67(26):7223-7231. doi: 10.1021/acs.jafc.8b05567. Epub 2019 Jun 25.

Abstract

The aim of this study was to investigate the effect of 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid (PCA), a metabolite of the fungicide fluopyram, on grapevine. During spring and summer 2015, grapevine growth disorders were observed in several countries in Europe. An unprecedented herbicide-like damage was diagnosed on leaves and flowers, causing significant loss of harvest. This study proposes PCA as the causing agent of the observed growth disorders. PCA was shown to cause leaf epinasty, impaired berry development that leads to crop loss, and root growth anomalies in Vitis vinifera similar to auxin herbicides in a dose-dependent manner. Using both field trials and greenhouse experiments, the present study provides first evidence for a link between the application of fluopyram in vineyards 2014, the formation of PCA, and the emergence of growth anomalies in 2015. Our data could be useful to optimize dosage, application time point, and other conditions for an application of fluopyram without phytotoxic effects.

Keywords: crop protection; fungicides; grapevine; grapevine phytotoxicity; growth anomalies; leaf epinasty; pesticides.

MeSH terms

  • Benzamides / adverse effects
  • Benzamides / metabolism*
  • Carboxylic Acids / adverse effects*
  • Carboxylic Acids / metabolism
  • Flowers / drug effects
  • Flowers / growth & development
  • Flowers / metabolism
  • Fruit / drug effects
  • Fruit / growth & development
  • Fruit / metabolism
  • Fungicides, Industrial / adverse effects*
  • Fungicides, Industrial / metabolism
  • Plant Leaves / drug effects
  • Plant Leaves / growth & development
  • Plant Leaves / metabolism
  • Pyridines / adverse effects*
  • Pyridines / metabolism*
  • Vitis / drug effects*
  • Vitis / growth & development*
  • Vitis / metabolism

Substances

  • Benzamides
  • Carboxylic Acids
  • Fungicides, Industrial
  • Pyridines
  • trifluoromethylpyridine
  • N-(2-(3-chloro-5-(trifluoromethyl)-2-pyridyl)ethyl)-alpha,alpha,alpha-trifluoro-o-toluamide