Design, synthesis, crystal structure and bioactivity evaluation of novel diethyl (arylfuranyl)(arylpyrazolylamino)methanephosphonates

GRAPHICAL ABSTRACT

ABSTRACT

A series of novel arylpyrazole derivatives containing aminomethanephosphonate and phenylfuran moieties were designed, synthesized and characterized by ¹H NMR, ³¹P NMR and IR spectroscopy and elemental analyses. The single crystal structure of diethyl [5-(4-chlorophenyl)furan-2-yl][3-cyano-1-(2,3,4-trifluorophenyl)-1H-pyrazol-5-ylamino]methanephosphonate (4l) was determined by X-ray diffraction. Preliminary bioassays showed that these phosphonates exhibit satisfactory insecticidal activities against Culexpipiens and Musca domestica at 0.1%. In particular, compound 4l exhibited a most promising KT50 value, which is superior to that of Dextraltetramethrin® and similar to Prallehtrin®. The structure-activity relationship was also preliminarily investigated.

KEYWORDS:

• Aminomethanephosphonate
• arylpyrazole
• bioactivity
• crystal structure
• synthesis

Acknowledgments

This work was supported by the Key Technology R&D Program of the Science and Technology Department of Jiangsu Province (No. BE 2011352) for financial support.