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Design, Synthesis, and Structure-Activity Relationship of New Pyrimidinamine Derivatives Containing an Aryloxy Pyridine Moiety.
- Source :
-
Journal of agricultural and food chemistry [J Agric Food Chem] 2017 Feb 15; Vol. 65 (6), pp. 1272-1280. Date of Electronic Publication: 2017 Feb 06. - Publication Year :
- 2017
-
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 by <superscript>1</superscript> H 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 (EC <subscript>50</subscript> = 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.
- Subjects :
- Chemistry Techniques, Synthetic
Cucumis sativus drug effects
Cucumis sativus microbiology
Drug Design
Drug Evaluation, Preclinical
Fungicides, Industrial chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Structure
Oomycetes pathogenicity
Plant Diseases microbiology
X-Ray Diffraction
Fungicides, Industrial chemistry
Fungicides, Industrial pharmacology
Pyridines chemistry
Structure-Activity Relationship
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5118
- Volume :
- 65
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Journal of agricultural and food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28118711
- Full Text :
- https://doi.org/10.1021/acs.jafc.6b05580