Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings

Scientific Reports
Yuanyuan LiuJinyuan Xu

Abstract

A series of novel strobilurin analogues (1a-1f, 2a-2e, 3a-3e) containing arylpyrazole rings were synthesized and characterized by NMR spectroscopy. The structures of 1f, 2b and 3b were also determined by single crystal X-ray diffraction analysis. These analogues were collected together with other twenty-eight similar compounds 4a-4f, 5a-5h, 6a-6h and 7a-7f from our previous studies, for in vitro bioassays and thorough structure-activity relationships (SARs) studies. Most compounds exhibited excellent-to-good fungicidal activity against Rhizoctonia solani, especially 5c, 7a, 6c, and 3b with 98.94%, 83.40%, 71.40% and 65.87% inhibition rates at 0.1 μg mL-1, respectively, better than commercial pyraclostrobin. Comparative molecular field analysis (CoMFA) was employed to study three-dimensional quantitative structure-activity relationships (3D-QSARs). Density functional theory (DFT) calculation was also carried out to provide more information regarding SARs. The present work provided some hints for developing novel strobilurin fungicides.

References

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Citations

Oct 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Loana MussoSabrina Dallavalle
Aug 29, 2020·Journal of Agricultural and Food Chemistry·Hui XiongQingchun Huang

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Methods Mentioned

BETA
NMR
X-ray
column chromatography

Software Mentioned

SAMPLS
DPS
97
SHELXS
SYBYL X
SHELXL
GuassView
MEP
Gaussian

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