Synthesis and Biological Activity of 1‐(Substituted phenoxyacetoxy)‐1‐(pyridin‐2‐yl or thien‐2‐yl)methylphosphonates

Abstract

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1 H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50 mg/L.

Synthesis and Biological Activity of 4‐[(Substituted Phenoxyacetoxy)methyl]‐2,6,7‐trioxa‐1‐phosphabicyclo[2.2.2]octane‐1‐one

“…The 4‐(hydroxy methyl)‐2,6,7‐trioxa‐1‐phosphabicyclo[2.2.2]octane‐1‐one 1 could be prepared by the treatment of the pentaerythritol with phosphorus oxychloride in dioxane. Substituted phenoxyacetic acids 2 and substituted phenoxyacetyl chlorides 3 were prepared according to the reported methods .…”

“…In our previous work, a series of 1-(substituted phenoxyacetoxy)alkylphosphonates, as potent pyruvate dehydrogenase complex (PDHc) inhibitors, were synthesized and showed notable bioactivities [1][2][3] (Scheme 1). To determine the effect of heterocyclic groups on the bioactivity, a series of heterocycle-containing 1-(substituted phenoxyacetoxy)alkylphosphonates [3] and phosphinates [4] were designed and synthesized, and some of them exhibited excellent herbicidal and fungicidal activities [3,4].…”

“…As an important class of pesticides, organic phosphorus compounds display a wide range of biological activities and have attracted considerable attention as the main source of lead compounds in agrochemicals. In our previous work, a series of 1‐(substituted phenoxyacetoxy)alkylphosphonates, as potent pyruvate dehydrogenase complex (PDHc) inhibitors, were synthesized and showed notable bioactivities (Scheme ). To determine the effect of heterocyclic groups on the bioactivity, a series of heterocycle‐containing 1‐(substituted phenoxyacetoxy)alkylphosphonates and phosphinates were designed and synthesized, and some of them exhibited excellent herbicidal and fungicidal activities .…”

Synthesis and Biological Activity of O‐Methyl Methyl 1‐(Substituted Phenoxyacetoxy)‐1‐(thien‐2‐yl)methylphosphinates

“…The fungicidal activity measurement method was adapted from Ref [11]. The phosphonates were dissolved in DMF (0.5-1.0 mL) to the concentration of 1000 mg/L.…”

“…And as typical heterocyclic groups, pyridinyl and thienyl are often introduced in the design of bioactive compounds [8][9][10]. Therefore, a series of O, O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyrid-2-yl or thien-2-yl)methylphosphonates were synthesized, and some of them exhibited excellent herbicidal and fungicidal activities [11].…”