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ACTIVITY:
Fungicide
(conazole)
CAS Name:
?-(4-fluorophenyl)-?-[(trimethylsilyl)methyl]-1H-1,2,4-triazole-1-ethanol
Structure:
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15382502
Pest Manag Sci. 2004 Sep;60(9):881-6.
Systemic activity of simeconazole and its
derivatives in plants.
Tsuda M, Itoh H, Kato S.
Agroscience Research Laboratories, Sankyo
Agro Co Ltd, 894 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342,
Japan. mktuda@sankyo-agro.co.jp
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 Kuhn 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.
PMID: 15382502 [PubMed - in process]
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15382501
Pest Manag Sci. 2004 Sep;60(9):875-80.
Evaluation of the systemic activity of
simeconazole in comparison with that of other DMI fungicides.
Tsuda M, Itoh H, Kato S.
Agroscience Research Laboratories, Sankyo
Agro Co Ltd, 894, Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342,
Japan. mktuda@sankyo-agro.co.jp
The systemic activity of simeconazole (RS-2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpropan-2-ol)
in plants was compared with those of eight other sterol demethylation
inhibitor (DMI) fungicides. Simeconazole prevented the infection
of Blumeria graminis (DC) Speer f sp hordei Marchal on barley
leaves within a radius of several centimeters from the edge of
local treatment on the leaves when the compound was separated
from the leaves by glass coverslips. This reveals that simeconazole
has prominent vapour-phase activity. Simeconazole showed excellent
curative activity against barley powdery mildew when treated 1-3
days after inoculation. Furthermore, this indicates that simeconazole
has notable translaminar activity because, when the compound was
applied onto either the adaxial or abaxial leaf surface, it showed
excellent efficacy against powdery mildew on the opposite side
of the leaf surface of barley and cucumber. Simeconazole also
showed excellent efficacy against barley powdery mildew by soil
drench 24h after inoculation. This suggests that simeconazole
was absorbed very quickly into the barley plant after treatment.
The permeability of the compound through cuticular membranes prepared
from tomato fruits was about 20% at 22 h after the treatment and
was much superior to that of the other DMI fungicides tested.
PMID: 15382501 [PubMed - in process]
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