Alkylating reactivity and herbicidal activity of chloroacetamides

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The relationship between S- and N-alkylating reactivity and herbicidal activity within a series of chloroacetamides, including several commercial herbicides and newly synthesised analogues was studied. The S-alkylating reactivity of selected chloroacetamides, as well as those of atrazine and chlorfenprop-methyl, was determined by in vitro GSH conjugation at a ratio of GSH to alkylating agent of 25:1. A spectrophotometric reaction using 4-(4-nitrobenzyl)pyridine was used to characterise the N-alkylating reactivity of the chemicals. Our results indicate that a reduced level of N-alkylating reactivity correlates with an improved herbicidal efficacy at a practical rate. However, the phytoxicity of the molecules is not simply dependent on chemical reactivities, but strictly related to the molecular structure, indicating that lipophilicity, uptake, mobility and induction of detoxifying enzymes may also be decisive factors in the mode of action.

Original languageEnglish
Pages (from-to)443-450
Number of pages8
JournalPest Management Science
Volume59
Issue number4
DOIs
Publication statusPublished - Apr 1 2003

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pyridines
gene induction
atrazine
hydrophobicity
chemical structure
mechanism of action
herbicides

Keywords

  • Alkylating reactivity
  • Chloroacetamides
  • Herbicide

ASJC Scopus subject areas

  • Agronomy and Crop Science
  • Insect Science

Cite this

Alkylating reactivity and herbicidal activity of chloroacetamides. / Jablonkai, I.

In: Pest Management Science, Vol. 59, No. 4, 01.04.2003, p. 443-450.

Research output: Contribution to journalArticle

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