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Synthesis and fungicidal activities of new 1,2,4-triazolo[1,5-a]pyrimidines. 2009

Qiong Chen, and Zu-Ming Liu, and Chao-Nan Chen, and Li-Li Jiang, and Guang-Fu Yang
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, PR China.

A series of new acetohydrazone-containing 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized for the purpose of searching for novel agrochemicals with higher fungicidal activity. Their in vitro fungicidal activities against Rhizoctonia solani were evaluated, and the most promising compound, 2-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanyl]-2'-[(2-hydroxyphenyl)methylidene]acetohydrazide (2-17), showed a lower EC(50) value (5.34 microg ml(-1)) than that of commercial carbendazim (EC(50)=7.62 microg ml(-1)). Additionally, compound 2-17 was also found to display broad-spectrum fungicidal activities, and its EC(50) value (4.56 microg ml(-1)) against Botrytis cinereapers was very similar to that of carbendazim. Qualitative structure-activity relationships (QSARs) of the synthesized compounds were also discussed.

UI MeSH Term Description Entries
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.
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
D012232 Rhizoctonia A mitosporic Ceratobasidiaceae fungal genus that is an important plant pathogen affecting potatoes and other plants. There are numerous teleomorphs. Rhizoctonias
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D016573 Agrochemicals Chemicals used in agriculture. These include pesticides, fumigants, fertilizers, plant hormones, steroids, antibiotics, mycotoxins, etc. Agrichemical,Agricultural Chemical,Agricultural Chemicals,Agrochemical,Agrichemicals,Chemicals, Agricultural,Chemical, Agricultural
D020128 Inhibitory Concentration 50 The concentration of a compound needed to reduce population growth of organisms, including eukaryotic cells, by 50% in vitro. Though often expressed to denote in vitro antibacterial activity, it is also used as a benchmark for cytotoxicity to eukaryotic cells in culture. IC50,Concentration 50, Inhibitory

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