title: Design, Synthesis, and Structure-Activity Relationship of New Pyrimidinamine Derivatives Containing an Aryloxy Pyridine Moiety.
abstract: The pyrimidinamine diflumetorim is an ideal template for the discovery of agrochemical lead compounds due to its unique mode of action, novel chemical structure, and lack of reported resistance. To develop a new pyrimidinamine fungicide effective against cucumber downy mildew (CDM), a series of new pyrimidinamine derivatives containing an aryloxy pyridine moiety were designed and synthesized by employing the recently reported intermediate derivatization method (IDM). The structures of all compounds were identified by1H NMR, elemental analyses, HRMS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Compound 9 gave the best activity (EC50= 0.19 mg/L), which is significantly better than the commercial fungicides diflumetorim, flumorph, and cyazofamid. The relationship between structure and fungicidal activity of the synthesized pyrimidinamines was explored. The study showed that compound 9 is a promising fungicide candidate for further development.
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, People's Republic of China.|State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Aiying
authors.identifier: http://orcid.org/0000-0001-9134-9280
authors.initials: A
authors.lastname: Guan
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Changling
authors.initials: C
authors.lastname: Liu
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Fan
authors.initials: F
authors.lastname: Yang
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Xie
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Jinbo
authors.initials: J
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd. , Shenyang 110021, People's Republic of China.
authors.forename: Zhinian
authors.initials: Z
authors.lastname: Li
authors.affiliation: Department of Applied Chemistry, China Agricultural University , Beijing 100193, People's Republic of China.
authors.forename: Mingan
authors.initials: M
authors.lastname: Wang
mesh_terms: D060326:Chemistry Techniques, Synthetic; D018553:Cucumis sativus / Q000187:drug effects / Q000382:microbiology; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009868:Oomycetes / Q000472:pathogenicity; D010935:Plant Diseases / Q000382:microbiology; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D005659:Fungicides, Industrial; D011725:Pyridines
keywords: cucumber downy mildew; fungicidal activities; intermediate derivatization method (IDM); structure−activity relationship