Synthesis and Systemic Fungicidal Activity of Silicon-Containing Azole Derivatives.

Itoh, Hiroyuki; Yoneda, Rieko; Tobitsuka, Junzo; Matsuhisa, Tadashi; Kajino, Hisaki; Ohta, Hiroshi; Hayashi, Noriki; Takahi, Yukiyoshi; Tsuda, Mikio; Takeshiba, Hideo

doi:10.1248/cpb.48.1148

Cited by 18 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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“…The organic layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated to give 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-4-trimethylsilylbut-3-en-2-ol (98 mg, 55%) as colorless crystals (recrystallized from diisopropyl ether), mp 118-120°C. 1 2-(4-Fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-5-trimethylsilyl-2-pentanol (4a) A solution of sodium hydride (60% mineral oil dispersion, 880 mg, 22.0 mmol) in dimethyl sulfoxide (20 ml) was heated at 70°C for 1 h. When the hydrogen gas ceased to evolve, the mixture was cooled to room temperature and trimethylsulfoxonium iodide (4.8 g, 21.8 mmol) was added. After stirring at room temperature for 0.5 h, 1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 5a (2.05 g, 10.0 mmol) was added and the mixture was stirred for 4 h at the same temperature.…”

Section: -(24-dichlorophenyl)-1-(1h-124-triazol-1-yl)-4-trimethylmentioning

confidence: 99%

“…The reaction mixture was partitioned between ethyl acetate and brine, the organic layer was dried over magnesium sulfate and concentrated to give a solid, and the solid obtained was chromatographed on silica gel (ethyl acetate-hexane, 1 : 1, v/v) to afford 1-{[2-(4-fluorophenyl)oxetane-2-yl]methyl}-1H-1,2,4-triazole 9a (1.29 g, 55%) as an oil. 1 8.30 (1H, s). This product was used for the next reaction without further purification.…”

Section: -(24-dichlorophenyl)-1-(1h-124-triazol-1-yl)-4-trimethylmentioning

confidence: 99%

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Synthesis of 1-Triazolyl-4-trimethylsilyl-2-butanol and 1-Triazolyl-5-trimethylsilyl-2-pentanol Derivatives and an Investigation of Their Fungicidal Activities

Itoh¹,

Yoneda²,

Tobitsuka³

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new series of azole derivatives of 1-triazolyl-4-trimethylsilyl-2-butanol and 1-triazolyl-5-trimethylsilyl-2-pentanol were synthesized and evaluated for fungicidal activities against rice blast, sheath blight, and powdery mildew on barley. The derivatives of 2,4-difluorobenzene exhibited high antifungal activities when applied by spray, but exhibited no fungicidal activity by submerged application.

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“…In a previous paper, 1) we reported synthesis and antifungal activity of triazole compounds 1 with a trimethylsilylmethyl moiety (Fig. 1).…”

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confidence: 98%

Synthesis and Fungicidal Activities of Silicon-Containing Derivatives of 2-Aryl-3-(1H-1,2,4-triazol-1-yl)propanenitriles.

Itoh¹,

Tanaka²,

Ohta³

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Synthesis and Systemic Fungicidal Activity of Silicon-Containing Azole Derivatives.

Cited by 18 publications

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Systemic activity of simeconazole and its derivatives in plants

Systemic activity of simeconazole and its derivatives in plants

Synthesis of 1-Triazolyl-4-trimethylsilyl-2-butanol and 1-Triazolyl-5-trimethylsilyl-2-pentanol Derivatives and an Investigation of Their Fungicidal Activities

Synthesis and Fungicidal Activities of Silicon-Containing Derivatives of 2-Aryl-3-(1H-1,2,4-triazol-1-yl)propanenitriles.

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