Systemic activity of simeconazole and its derivatives in plants.
The systemic activity of simeconazole (RS-2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpropan-2-ol) and a number of its derivatives in plants has been investigated to establish which portion of the structure of the molecule contributes to this outstanding activity. The results revealed that the hydroxyl group of the simeconazole moiety is essential for vapour-phase activity and translocation from roots of the compound. They showed that the presence of a fluorine atom in the structure was not indispensable for vapour-phase activity or translocation from roots, although the fluorine atom contributed to these systemic movements. In addition, it was found that the fungicidal activity of simeconazole against Rhizoctonia solani Kühn and Blumeria graminis DC fsp hordei Marchal is potentiated by the fluorine atom, since the activity of a compound which lacked fluorine in the 4-position of the phenyl ring was inferior to that of simeconazole. A compound in which the silicon atom of simeconazole was replaced by a carbon atom showed lower antifungal activity than simeconazole, while phytotoxicity was caused in rice plants by soil drench of the compound. Therefore, the silicon atom of simeconazole may contribute to its selectivity between fungi and plants.
Tsuda
Mikio
M
Agroscience Research Laboratories, Sankyo Agro Co Ltd, 894 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, Japan. mktuda@sankyo-agro.co.jp
Itoh
Hiroyuki
H
Kato
Shigehiro
S
D001203:Ascomycota / Q000187:drug effects / Q000254:growth & development; D002463:Cell Membrane Permeability / Q000187:drug effects; D005461:Fluorine / Q000737:chemistry / Q000378:metabolism; D005638:Fruit / Q000378:metabolism / Q000382:microbiology; D005658:Fungi / Q000187:drug effects* / Q000254:growth & development; D005659:Fungicides, Industrial / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D001467:Hordeum / Q000382:microbiology*; D012275:Oryza / Q000382:microbiology*; D010935:Plant Diseases / Q000382:microbiology; D019441:Plant Epidermis / Q000378:metabolism / Q000382:microbiology; D018515:Plant Leaves / Q000378:metabolism / Q000382:microbiology; D018517:Plant Roots / Q000378:metabolism / Q000382:microbiology; D012232:Rhizoctonia / Q000187:drug effects / Q000254:growth & development; D012825:Silicon / Q000737:chemistry / Q000378:metabolism; D014230:Triazoles / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D014297:Trimethylsilyl Compounds / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*
C494052:2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpropan-2-ol; D005659:Fungicides, Industrial; D014230:Triazoles; D014297:Trimethylsilyl Compounds; D005461:Fluorine; D012825:Silicon