Synthesis and fungicidal activity against Pyricularia oryzae of 6-(1,2,4-triazol-4-yl) chromone and -1-thiochromone derivatives

Abstract

: A series of novel 6-(1,2,4-triazol-4-yl) chromone and -1-thiochromone (benzo [b]thiazin-4-one) derivatives was obtained by cyclisation via thiosemicarbazides which were prepared by reaction of hydrazines and the corresponding isothiocyanates. Their fungicidal activity was evaluated against the rice blast fungus Pyricularia oryzae. Of this series, 2,5,8-trimethyl-6-(1-propyl-5-thioxo-3-triÑuoromethyl-1,2,4-triazol-4-yl) chromone, 6-(1-butyl-5-thioxo-3-triÑuoro-methyl-1,2,4-triazol-4-yl)-2,5,8-trimethylchromone, 6-(1-hexyl-3-methyl-5-thioxo-1,2,4-triazol-4-yl)-2,5,8-trimethylchromone and 6-(1-allyl-5-thioxo-3-triÑuoro-methyl-1,2,4-triazol-4-yl)-2,5,8-trimethylchromone were highly active (pEC 50 [ StructureÈactivity relationship studies using the capacity factor k@ as a 6É0). hydrophobicity index suggested that the log k@ optimum for 2,5,8-trimethylchromone and -1-thiochromone derivatives was around 1É0, equivalent to a log value of c. 4É4. 1998 SCI P ow ( Pestic. Sci., 52, 309È320 (1998)

Electrolytic Partial Fluorination of Organic Compounds. 54.1 Anodic Mono- and Trifluorination of Thiochroman-4-one Derivatives and the Factors Affecting Product Selectivity

“…Thiochroman-4-one and 1-thiochromone derivatives are interesting classes of heterocycles due to their broad pharmacological and medicinal importance. , In this work, we successfully performed anodic fluorination of ( E )-3-benzylidene-2,3-dihydrothiochroman-4-ones 1 to provide the corresponding mono- and trifluorinated products. Anodic fluorination of an isomer of 1 , a 1-thiochromone derivative, also provided the same fluorinated products derived from 1 .…”

Synthesis and antidiabetic activity of some new chromonyl-2,4-thiazolidinediones

“…2,4-Thiazolidinediones (2,4-TZDs) are a new class of antidiabetic agents that increase insulin sensitivity, enhance glucose control, improve the lipid profile, suppress inflammatory cytokines, and improve vascular structure and function 2 . Chromones, occurring widely throughout the plant kingdom, are one of the most representative families of plant secondary metabolites and display a remarkable spectrum of biological activities such as anticancer, antimicrobial, and antidiabetic activities [3][4][5][6] .…”

Synthesis and molluscicidal structure–activity relationships of some novel 1,2,4‐triazole N‐methyl carbamates

“…1,2,4‐Triazoles constitute an important group of heterocylic nitrogen derivatives showing a broad spectrum of biological activity as herbicides, cotton defoliants, growth regulators,9 insecticides10 and fungicides 11. In our recent research, 2‐[(1,2,4‐triazol‐1‐ylmethyl)amino]‐3‐methylpyridine, as well as (1 H ‐1,2,4‐triazol‐1‐ylmethyl)anilines, N ‐alkylanilines and N,N ‐dialkylanilines exhibited promising molluscicidal activity 12.…”