Design, Synthesis, and Evaluation of Fungicidal Activity of Novel Pyrazole‐Containing Strobilurin Derivatives^†

Abstract

Drug design | Strobilurins | Biological activity | Structure-activity relationships |Cytochrome bc 1 complexIn searching for novel fungicidal leads, a series of pyrazole-containing strobilurins were rationally designed, synthesized and characterized. Bioassay indicated that compound I-7 displayed excellent fungicidal activity against a broad spectrum of plant pathogens such as Gibberella zeae, Rhizoctonia cerealis, Sclerotinia sclerotiorum, Phytophthora infestans, Physalospora piricola and Pellicularia sasakii with EC 50 of 0.16, 0.02, 0.72, 0.07, 0.77 and 0.65 μg/mL, respectively, which were 3-10 times more potent than the positive control azoxystrobin against the corresponding pathogens. Moreover, like azoxystrobin and kresoxim methyl, I-7, displayed excellent protective activity against P. sorghi. Molecular docking validated that I-7 and azoxystrobin would share a similar binding mode with cytochrome bc 1 complex. This study demonstrates that I-7 is a promising fungicidal candidate for further development.

Design and Synthesis of Pyrimidine Amine Containing Isothiazole Coumarins for Fungal Control

“…13 7.08 (d, J = 8.9 Hz, 1H), 6.56 (s, 1H), 4.28 (t, J = 5.7 Hz, 2H), 3.82 (q, J = 5.5 Hz, 2H), 2.20 (s, 3H), 2.10 (s, 3H). 13 8.06 (t, J = 5.7 Hz, 1H), 7.25 (d, J = 8.9 Hz, 1H), 7.08 (d, J = 9.0 Hz, 1H), 7.05 (t, J = 53.1 Hz, 1H), 6.56 (s, 1H), 4.31 (t, J = 5.7 Hz, 2H), 3.90 (q, J = 5.7 Hz, 2H), 2.17 (s, 3H). 13 .0 Hz, 1H), 6.56 (s, 1H), 4.28 (t, J = 5.9 Hz, 2H), 3.84 (q, J = 5.7 Hz, 2H), 2.36 (s, 3H), 2.18 (s, 3H).…”

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

“…Compound 20 exhibited outstanding in vitro fungicidal activity against Rhizoctonia cerealis , P. infestans , G. zeae , Pellicularia sasakii , Sclerotinia sclerotiorum , and P. piricola with EC 50 values ranging from 0.02 to 0.77 μg/mL, which were much more potent than those of azoxystrobin. A molecular docking study showed that compound 20 could bind with cytochrome bc 1 complex as well as azoxystrobin …”

“…A molecular docking study showed that compound 20 could bind with cytochrome bc 1 complex as well as azoxystrobin. 43 These results demonstrated that the pyrazole ring could act as important side chain in the research and development of novel β-methoxyacrylate fungicides.…”

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

“…(EC 50 = 53.26 mg/L). In the past few years, BASF had reported several aminoalkylpyrimidine derivates 30–37 [ 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 ]. As shown in the Figure 6 , phenoxypyridine was linked to aminoalkylpyrimidine in various link arms resulting in some molecules with good protective fungicidal activity.…”