The Synthesis and Herbicidal Evaluation of Fluorine-Containing Phenoxyacetoxyalkylphosphonate Derivatives

Abstract

To investigate the influence of a fluorine moiety on the biological activity of phenoxyacetoxyalkylphosphonates, a series of fluorine-containing phenoxyacetoxyalkylphosphonates were synthesized and screened for herbicidal activity in a greenhouse. The majority of the title compounds showed better preemergence activity than postemergence activity against the test plants, especially on monocotyledon. Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity.

Keywords:

• 1-hydroxyl alkylphosphonate
• fluorophenoxyacetic acid
• herbicidal activity
• synthesis

Acknowledgments

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400) and the National Natural Science Foundation of China (Project No. 20372023).

Notes

^a Ech: Echinochloa Crusgalli Beava; Dig: Digitaria Sanguinalis scop; Bra: Brassica napus L. Ama: Amaranthus retroflerus L.; Med: Medicago sativa

^a IC₅₀ value is defined as the micromolar concentration required for 50% inhibition in the growth of a root length of Cucumber (Cucumis sativa L.)

^bThe fiducial limit was 95%.