Synthesis, Crystal Structure, and Biological Activities of 2-Cyanoacrylates Containing Furan or Tetrahydrofuran Moieties

Abstract

A series of novel cyanoacrylates containing furan or tetrahydrofuran moieties were synthesized, and their structures were characterized by 1H NMR, elemental analysis, and single-crystal X-ray diffraction analysis. The herbicidal, plant growth regulatory, fungicidal, and antiviral activities of these cyanoacrylates were evaluated. The results of herbicidal activities showed that most of these cyanoacrylates exhibited higher herbicidal activities against dicotyledonous weeds than monocotyl-edonous weeds, and the compounds containing the tetrahydrofuran moiety gave higher herbicidal activities than corresponding furan analogues; (Z)-ethoxyethyl 2-cyano-3-isopropyl-3-(tetrahydrofuran-3-yl)methaneaminoacrylate showed excellent herbicidal activities against amaranth pigweed in postemergence treatment at a dose of 375 g/ha. At the same time, these cyanoacrylates had interesting plant growth regulatory activities, and some compounds stimulated radicle growth of cucumber, whereas some compounds had an inhibitory effect. These cyanoacrylates showed fungicidal activities as well.

Design, Synthesis, and Trypanocidal Activity of Novel 5‐Nitroimidazolyl O‐Benzyloxime Ethers

“…This intermediate 8 was isolated, but its physicochemical properties and spectroscopic analysis were not performed because of its great chemical instability. Next, the desired oxime ( 10 ) was synthesized in 85% yield from the condensation reaction between the hydroxylamine and the aldehyde ( 8 ) in water . The analysis of 1 H NMR spectrum of ( 10 ) indicated the selective formation of the diastereomer presenting relative configuration ( E ) at the imine double bond level, as previously reported for other aldoximes .…”

Phosphosulfonic acid‐catalyzed green synthesis and bioassay of α‐aryl‐α′‐1,3,4‐thiadiazolyl aminophosphonates

“…They are receiving much attention as peptide analogs due to their structural similarity to natural α‐amino acids . Compounds bearing the α ‐ aminophosphonate moiety play an important role in agriculture as plant growth regulators, herbicides, and insecticides . In medicine, they act as cytotoxic, antioxidant, antimicrobial, and antiviral agents, and as enzyme inhibitors .…”

Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains

“…The compounds, 1-3, were generally prepared on refluxing the corresponding aldehyde with hydroxylamine in an aqueous solution containing potassium carbonate, following a general procedure [22]: a mixture of an aldehyde (2 mmol), hydoxyamine.hydrochloride (2.2 mmol) and potassium carbonate (4 mmol) in water (20 mL) was refluxed for 1 hour. The reaction mixture was extracted into ether, dried over magnesium sulphate and rotary evaporated.…”