A series of new alkyl and arylalkyl ethers of 2-(2,4-dichlorophenyl)-3- (1H-1,2,4-triazol-1-yl)propanol, related to the fungicide tetraconazole, were synthesized and tested in vitro or in vivo against seven common pathogens in comparison with tetraconazole. In vitro, most of them exhibited a broad spectrum of activity and an efficacy of the same order of magnitude of the standard, but the activity was influenced by the nature of the substituents. A QSAR study showed that lipophilicity is a major positive parameter in affecting the activity; the second relevant parameter is μ, whereas geometrical descriptors indicate that linear and narrow substituents are more suitable than wide ones. In in vivo assays some compounds had good activity on bean rust, either protective or curative. Sterol analysis showed that the mechanism of action is due to inhibition of 14α-demethylase.

Synthesis, Fungicidal Activity, and QSAR of a Series of 2-Dichlorophenyl-3-triazolylpropyl Ethers / A. Arnoldi, R. Carzaniga, G. Morini, L. Merlini, G. Farina. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 48:6(2000), pp. 2547-2555.

Synthesis, Fungicidal Activity, and QSAR of a Series of 2-Dichlorophenyl-3-triazolylpropyl Ethers

A. Arnoldi
Primo
;
L. Merlini
Penultimo
;
G. Farina
Ultimo
2000

Abstract

A series of new alkyl and arylalkyl ethers of 2-(2,4-dichlorophenyl)-3- (1H-1,2,4-triazol-1-yl)propanol, related to the fungicide tetraconazole, were synthesized and tested in vitro or in vivo against seven common pathogens in comparison with tetraconazole. In vitro, most of them exhibited a broad spectrum of activity and an efficacy of the same order of magnitude of the standard, but the activity was influenced by the nature of the substituents. A QSAR study showed that lipophilicity is a major positive parameter in affecting the activity; the second relevant parameter is μ, whereas geometrical descriptors indicate that linear and narrow substituents are more suitable than wide ones. In in vivo assays some compounds had good activity on bean rust, either protective or curative. Sterol analysis showed that the mechanism of action is due to inhibition of 14α-demethylase.
Settore CHIM/10 - Chimica degli Alimenti
2000
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/181884
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