Synthesis of silicon-containing azole derivatives with magnesium bromide diethyl etherate, and an investigation of their fungicidal activities

Itoh, Hiroyuki; Kajino, Hisaki; Tsukiyama, Takahiro; Tobitsuka, Junzo; Ohta, Hiroshi; Takahi, Yukiyoshi; Tsuda, Mikio; Takeshiba, Hideo

doi:10.1016/s0968-0896(02)00302-4

Cited by 24 publications

(9 citation statements)

References 14 publications

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“…The structures of the compounds tested are shown in Fig 1. All compounds were synthesized9–11 by the Agroscience Research Laboratories, Sankyo Agro Co Ltd. The compounds were dissolved in acetone + methanol (90 + 10 by volume) at 10 g litre −1 and stored at −20 °C.…”

Section: Methodsmentioning

confidence: 99%

Systemic activity of simeconazole and its derivatives in plants

Tsuda¹,

Itoh²,

Kato³

2004

Pest Management Science

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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.

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Section: Methodsmentioning

confidence: 99%

Systemic activity of simeconazole and its derivatives in plants

Tsuda¹,

Itoh²,

Kato³

2004

Pest Management Science

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“…13) 4-(4-Chlorophenyl)-2-phenyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol (4a) was prepared and the Grignard reaction performed as described previously. 14) A solution of 1-phenyl-2-(1H-1,2,4-triazol-1-yl) ethanone (3a) (2.0 mmol) in dichloromethane (4 mL) was added to a suspension of magnesium bromide diethyl etherate (4.0 mmol) in dichloromethane (6 mL) at room temperature and stirred for 0.5 hr. A solution of [3-(4-chlorophenyl) propyl] magnesium bromide in THF was added to ice.…”

Section: Chemistrymentioning

confidence: 99%

Tebuconazole derivatives are potent inhibitors of strigolactone biosynthesis

et al. 2013

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To find strigolactone (SL) biosynthesis inhibitors, we screened the azolecontaining chemicals that reduce the level of 2′-epi-5-deoxystrigol (epi-5DS) in rice. As a result of the screening, tebuconazole, a known fungicide targeting ergosterol biosynthesis, was selected as a potent SL biosynthesis inhibitor. A structure-activity relationship study of tebuconazole was carried out to discover more potent SL biosynthesis inhibitors. By evaluating the inhibitory activity on epi-5DS biosynthesis, we found that 2-(2-chlorophenyl)-4-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol (4b) and 4-(4-chlorophenyl)-2-(4-phenoxyphenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (4e) showed potent ability to reduce epi-5DS biosynthesis.

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“…Simeconazole was synthesized (Itoh et al , 2002 and formulated as 15 g kg −1 granules (Mongarit granule) by Agroscience Research Laboratories, Sankyo Agro.…”

Section: Fungicidementioning

confidence: 99%

Optimal application timing of simeconazole granules for control of rice kernel smut and false smut

Tsuda¹,

Sasahara

Ohara³

et al. 2006

J Gen Plant Pathol

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We investigated the optimal timing of simeconazole (RS-2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpropan-2-ol) application for controlling rice kernel smut in field trials in Miyagi Prefecture, Japan, using formulations of simeconazole (1.5% granules). The field tests revealed that a submerged application of simeconazole granules (450-600 g ai/ha) at 1-5 weeks before heading was highly effective against kernel smut, with treatments 1-2 weeks before heading being the most effective. Submerged application of the fungicide at 2-5 weeks before heading was also highly effective against false smut, with treatment 3 weeks before heading being the most effective. These periods overlap the timing for optimal application of simeconazole to control rice sheath blight and ear blight. Consequently, we concluded that treatment with simeconazole 2-3 weeks before heading can be a useful tool for controlling all four diseases.

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Synthesis of silicon-containing azole derivatives with magnesium bromide diethyl etherate, and an investigation of their fungicidal activities

Cited by 24 publications

References 14 publications

Systemic activity of simeconazole and its derivatives in plants

Systemic activity of simeconazole and its derivatives in plants

Tebuconazole derivatives are potent inhibitors of strigolactone biosynthesis

Optimal application timing of simeconazole granules for control of rice kernel smut and false smut

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