Fungitoxicity of acid and alkaline hydrolysis products of drazoxolon and related arylhydrazonoisoxazolones

Abstract

Drazoxolon and related 3-methyl-4-arylhydrazono-5-isoxazolones are hydrolysed by acid to 2-arylhydrazono-3-oxobutyric acids and by alkali to l-arylhydrazono-2-hydroxyiminopropanes and 2-arylhydrazono-3-hydroxyiminobutyric acids. Although many of the hydrolysis products show good antifungal activity in spore germination tests they are inferior to drazoxolon as protectants for the control of Uromyces fabae on broad bean and as protectants and eradicants against Erysiphe graminis on wheat. Neither drazoxolon nor its hydrolysis products show much activity as therapeutants. 357

Investigations on fungicides: XIV. Fungitoxicity of N‐(2,2,2–trichloro‐1–methoxyethyl)‐formamide and related compounds

“…The methods used for assessing inhibition of spore germination, evaluating protectant and eradicant activity and measuring activity in a leaf disk test are described by Lehtonen, Summers & Carter (1972) and only a brief outline of these tests will be given here.…”

Asymmetric Addition and Cycloaddition Reactions with Ylidene‐Five‐Membered Heterocycles

“…Isoxazolin‐5‐ones are versatile five‐membered heterocycles that can be found in natural products isolated from bacteria, [50] fungi, [51] insects [52] or seedlings [53] . This moiety an its derivate 4‐ylidene‐isoxazolin‐5‐one are present in some biologically active compounds including anti‐fungal agents, [54] PTP 1 B inhibitors with anti‐obesity activity, [55] antimicrobial agents [56] or anti‐cancer agents [57] . Moreover, the 4‐ylidene‐isoxazolin‐5‐one core is present in new photoluminescent materials [58] and donor‐acceptor molecules that can act as dyes (Figure 3).…”

Stepwise Microhydration of Isoxazole: Infrared Spectroscopy of Isoxazole-(Water)n≤2 Clusters in Helium Nanodroplets

“…Because of their high water solubility and large thermal stability, azoles are frequently used in therapeutic and natural product synthesis . Among these species, oxazole and its structural isomer isoxazole have attracted considerable attention due to their efficacy in interacting with a wide spectrum of protein targets, which results in antifungal, antibacterial, − antimicrobial, antitumor, antiviral, and anti-TB activities. Isoxazole is a five-membered heterocyclic ring, which features two different neighboring heteroatoms, nitrogen (N) and oxygen (O).…”