Design, synthesis and fungicidal activity of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines. 2009

Hui-Chao Li, and Chang-Ling Liu, and Bao-Shan Chai, and Miao Li, and Zhi-Nian Li, and Ji-Chun Yang
Agrochemical Discovery Department, Shenyang Research Institute of Chemical Industry, Shenyang 110021, China.

A series of novel compounds (5-8) was designed and synthesized by integrating the active pharmacophore of the N-phenylpyrimidin-2-amine fungicide with the structure of strobilurin fungicide. The rationale of this approach was to determine if these new compounds exhibit unique biological activity (selectivity and potency) compared with the commercial standards. The title compounds were prepared from 2-(phenylamino)pyrimidin-4-ols (3) by treatment with one equivalent of intermediates (4) containing strobilurin pharmacophores. 2-(Phenylamino)pyrimidin-4-ols (3) were in turn prepared from phenylguanidines (1) and substituted beta-ketoesters (2). Biological activities evaluated in the greenhouse indicated that compounds 5a, 6a and 7a have good fungicidal activity at 25 mg/L, comparable with that of the commercial standards, cyprodinil and azoxystrobin.

UI MeSH Term Description Entries
D008689 Methacrylates Acrylic acids or acrylates which are substituted in the C-2 position with a methyl group. Methacrylate
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D005658 Fungi A kingdom of eukaryotic, heterotrophic organisms that live parasitically as saprobes, including MUSHROOMS; YEASTS; smuts, molds, etc. They reproduce either sexually or asexually, and have life cycles that range from simple to complex. Filamentous fungi, commonly known as molds, refer to those that grow as multicellular colonies. Fungi, Filamentous,Molds,Filamentous Fungi,Filamentous Fungus,Fungus,Fungus, Filamentous,Mold
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D013055 Spectrophotometry, Infrared Spectrophotometry in the infrared region, usually for the purpose of chemical analysis through measurement of absorption spectra associated with rotational and vibrational energy levels of molecules. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) IR Spectra,Infrared Spectrophotometry,IR Spectras,Spectra, IR

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