Synthesis and fungistatic activity of new groups of 2,4-dihydroxythiobenzoyl derivatives against phytopathogenic fungi.
Twenty-six compounds, derivatives of amides, hydrazines, hydrazides, hydrazones, and semicarbazides, with a 2,4-dihydroxythiobenzoyl moiety, were synthesized from sulfinyl-bis(2,4-dihydroxythiobenzoyl). The compositions and chemical structures of these compounds were confirmed by IR, (1)H NMR, EI-MS, and elemental analysis. Antifungal properties of chemicals under in vitro conditions against five phytopathogenic fungi were estimated. In vivo studies against Erisiphe graminis were also carried out. The compounds N-substituted with an 2,4-dihydroxythiobenzamide group proved to be the most active. N-2-(1-Cinnamylbenzene ester)-2,4-dihydroxythiobenzamide, under in vitro conditions, showed activity at the level of 80-100% development of most pathogens at a concentration of 20 microg/mL and partially at a concentration of 200 microg/mL. For compounds with -HN-NH- or -NH-N= moiety, weak or no fungistatic properties were found at the concentrations studied.
Legocki
Jan
J
IPO, Annopol 6, 03-236 Warsaw, Poland, and Department of Chemistry, University of Agriculture, Akademicka 15, 20-950 Lublin, Poland.
Matysiak
Joanna
J
Niewiadomy
Andrzej
A
Kostecka
Małgorzata
M
D000528:Alternaria / Q000187:drug effects; D001203:Ascomycota / Q000187:drug effects; D001549:Benzamides / Q000138:chemical synthesis / Q000494:pharmacology; D020171:Botrytis / Q000187:drug effects; D002934:Cinnamates / Q000138:chemical synthesis / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D005670:Fusarium / Q000187:drug effects; D015394:Molecular Structure; D010944:Plants / Q000382:microbiology*; D012232:Rhizoctonia / Q000187:drug effects; D013329:Structure-Activity Relationship
D001549:Benzamides; D002934:Cinnamates; D005659:Fungicides, Industrial; C471214:N-2-(1-Cinnamylbenzene ester)-2,4-dihydroxythiobenzamide