Hexaconazole is a kind of broad-spectrum systemic trazole fungicide. It can be used for the treatment of many kind of fungi diseases caused by ascomycetes, basidiomycetes, and imperfect fungi. It is especially suitable for the treatment of fungi diseases such as powdery mildew, rust, scab, brown blotch and anthracnose caused by ascomycetes and basidiomycetes. In China, India and some other Asian countries, it is mainly used for the control of rice sheath blight. It is applicable to apples, grapes, bananas, vegetables, peanuts, and cereal crops as well as ornament plants. Its mechanism of action is through inhibiting the biosynthesis of ergosterol (a key component of the fungi membrane) of fungi.
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Hexaconazole is a broad-spectrum triazole fungicide that inhibits ergosterol biosynthesis via inhibition of the cytochrome P450-dependent 14α-demethylation of lanosterol, which results in disruption of the fungal cell membrane and cell death. It is fungicidal against the powdery mildews B. graminis and S. cucurbitae on cucumber plants in a concentration-dependent manner and is curative against powdery mildew on barley plants when used at a concentration of 6.7 mg/L. It also inhibits growth of R. bataticola and S. rolfsii (ED50s = 6.35 and 1.27 mg/L, respectively). Exogenous application of hexaconazole (15 mg/L) to M. chamomilla plants improves water, proline, and protein contents as well as increases non-enzymatic and enzymatic antioxidant and apigenin-7-glucoside content during a water deficit stress tolerance test. Hexaconazole inhibits the differentiation of mouse embryonic stem cells into cardiomyocytes (EC50 = 16.6 μM). It also induces bone morphological defects in mouse fetuses when administered to pregnant adult females during gestation.
Off-White to Pale Yellow Solid
Hexaconazole is a systematic fungicide of the triazole class. Hexaconazole has a broad spectrum antifungal activity and is commonly used in the control of apple, coffee and peanut diseases.
Hexaconazole is a systemic fungicide used for the control of
many fungi, particularly Ascomycetes and Basidiomycetes on a variety
of crops. It controls powdery mildews, scabs and rusts of vines, pome
fruits, vegetables and major diseases of small grain cereals.
ChEBI: 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol is a member of the class of triazoles that is 1-hexyl-1H-1,2,4-triazole in which the hydrogens at position 2 of the hexyl chain are replaced by hydroxy and 2,4-dichlorophenyl groups. It has a role as a chelator. It is a tertiary alcohol, a member of triazoles and a dichlorobenzene.
General procedure: butylmagnesium bromide was prepared according to the literature method. Under nitrogen protection, magnesium bromide diethyl ether compound (0.28 g, 1.08 mmol) was slowly added to a dichloromethane solution (2 mL) of (2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone (0.10 g, 0.45 mmol) in stirring. The reaction mixture was stirred at room temperature for 90 min and then cooled to 0°C, followed by the slow dropwise addition of an ether solution of methylmagnesium bromide (3.0 M, 0.41 mL, 1.21 mmol). The reaction system was slowly warmed to room temperature and stirring was continued for 12 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (2 mL) and extracted with dichloromethane (3 x 5 mL). The organic phases were combined and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: methanol/dichloromethane=5:95, Rf=0.20) to afford the target compound 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (0.035 g, 33% yield) as a white solid.
Metabolism of hexaconazole in plants involves primarily oxidation of the
alkyl side chain.
Hexaconazole is stable for at least 6 years at ambient temperature. It is
stable to hydrolysis and photolysis in water.
[1] European Journal of Medicinal Chemistry, 2017, vol. 133, p. 309 - 318
