Antifungal and Plant Growth Inhibitory Activities of Stereo and Optical Isomers of 2-Triazolylcycloalkanol Derivatives

Abstract

The cis-and traps-isomers of 1-(4-chlorophenyl)-2-(1 H-1, 2, 4-triazol-l-yl) cycloheptanol (1, 2) were compared in antifungal and plant growth-inhibitory activities. The cis-isomer of triazolylcycloheptanol had stronger antifungal activity against most fungi than the transisomer in vitro. Against Rosellinia nacatrix, however, the traps-isomer showed much stronger antifungal activity than the cis-isomer. In preventive activity against cucumber gray mold, powdery mildew, sclerotinia rot and rice blast, the cis-isomer was much stronger than the traps-isomer. In disease-controlling activity against wheat powdery mildew and oat crown rust, the cis-isomer was slightly stronger than the traps-isomer, whereas against rice sheath blight both isomers were similarly active. On the other hand, the traps-isomer had much stronger inhibitory activity than the cis-isomer on the growth of rice seedlings. Diastereomers of 1-substituted-2-(1 H-1, 2, 4-triazol-l-yl) cyclohexanols (3-8) were also compared in biological activity. In disease-controlling activity the cis-isomers were more effective than the corresponding traps-isomers against cucumber gray mold and powdery mildew. In plant growth inhibitory activity the traps-isomers were more effective than the cis-isomers on rice seedlings. Between the two enantiomers of cis-1-(4-chlorophenyl)-2-(1 H-1, 2, 4-triazol-1-yl)cycloheptanol (1), the preventive activity of the (l)-enantiomer was about two times stronger than that of the (d)-enantiomer against cucumber gray mold and powdery mildew. The (l)-enantiomer also had stronger growth inhibitory activity on rice seedlings than the (d)-enantiomer.

Synthesis of New Bis-1,2,4-Triazole Derivatives

“…1,2,4-triazoles and their derivatives are found to be associated with various biological activities such as anticonvulsant [1][2], antifungal [3][4][5], anticancer [6][7][8][9], antiinflammatory [10][11][12] and antibacterial properties [13][14][15][16]. Several compounds ( Figure 1) containing 1,2,4-triazole rings are well known as drugs.…”

Perfil químico y biológico de aceites esenciales de plantas aromáticas de interés agro-industrial en Castilla-La Mancha (España)

“…Para determinar la actividad antifúngica se empleó el método de dilución en agar (Murabayashi et al, 1991) con ligeras modificaciones (Giménez-Mariño, 2006). Se emplearon 5 concentraciones diferentes: 1, 0.5, 0.05 y 0.01 mg de extracto por cada ml de medio.…”

Synthesis of Stereoisomers of Ipconazole and Their Fungicidal and Plant Growth Inhibitory Activities

“…2. Isopropyl group was introduced into methyl 2-oxocyclopentanecarboxylate (1), the resulting product was subjected to Dieckmann recyclization reaction5> to form methyl 3-isopropyl-2-oxocyclopentanecarboxylate (2), and subsequently, 4-chlorobenzyl group was introduced,6 followed by hydrolysis and decarboxylation7 to obtain 2-(4-chlorobenzyl)-5-isopropylcyclopentanone (3). To obtain four racemic diastereomers of 4-(4-chlorobenzyl)-7-isopropyl-l-oxaspiro [2.4] heptane (4), two methods (A and B) were examined.…”

“…Enantiomer (-)-SSF-109 is more active than (+)-SSF-109 in fungicidal and plant growth inhibitory activities. 3 It is particularly interesting to investigate the relationship between stereochemical structure and biological activity in the viewpoint of the elucidation of the optimum threedimensional structure for the target enzyme. 4 In this paper the synthesis of stereoisomers of Ipconazole and fungicidal and plant growth inhibitory activities of each isomer are described.…”