Potential new fungicides: N-acyl-5-methyl-3(2H)-isoxazolone derivatives

Abstract

Various 2-N-acyl-5-methylisoxazolone derivatives were prepared, and their antifungal activities were evaluated in vitro with mycelial growth inhibition tests. In contrast with N-alkyl derivatives, the acyl compounds showed significant activity against Pyrenophora graminea, Fusarium graminearum, Alternaria alternata, Cercospora beticola, Rhynchosporium secalis, Septoria tritici, Microdochium nivale, Rhizoctonia solani and Gaeumannomyces graminis. Of note, cinnamoyl, 3-furan-3-ylacryloyland 3-thiophen-3-yl-acryloylamides, and t-butylacetyl and pivaloyl derivatives showed high inhibition rates at 25 mg/L against R. solani and G. graminis, respectively.

Potential fungicidal activity of 3-(substituted oxy)-5-methylisoxazoles

“…The acetyl derivative (45) also showed activity against P. graminea, A. alternate, C. beticola, R. secalis, S. tritici, Microdochium nivale, and Gaeumannomyces graminis. 12) These results coincided well with the previous result that the CO-bond linkage bound to the 2N-position was crucial for antifungal activity against P. graminea, A. alternata, C. beticola, R. secalis, and S. tritici. 12) However, interestingly, the non-acyl compound (4) showed significant activity.…”

“…12) These results coincided well with the previous result that the CO-bond linkage bound to the 2N-position was crucial for antifungal activity against P. graminea, A. alternata, C. beticola, R. secalis, and S. tritici. 12) However, interestingly, the non-acyl compound (4) showed significant activity. Considering that the activity pattern of the compound was similar to hymexazol, hymexazol may be produced from this silylamine derivative (4) due to the fragile N-Si bond.…”

“…[7][8][9][10][11] In a previous study, we reported that the antifungal activities of 2N-acyl hymexazol derivatives against some pathogens such as Rhizoctonia solani were higher than those of hymexazol. 12) In this study, we examined the antifungal activities or disease control activities of the 3O-esters of 3-hydroxy-5-methylisoxazol ( Fig. 1) against several plant pathogens.…”

Crystal structure and Hirshfeld surface analysis of (Z)-3-methyl-4-(thiophen-2-ylmethylidene)isoxazol-5(4H)-one

“…They are used for the treatment of cerebrovascular disorders and as muscle relaxants. They are also herbicides (Tomita et al, 1977) and fungicides (Miyake et al, 2012). On other hand, isoxazolone derivatives constitute excellent intermediates for the synthesis of various heterocycles such as pyridopyrimidines (Tu et al, 2006), quinolines (Abbiati et al, 2003) and undergo various chemical transformations (Batra & Bhaduri, 1994).…”

2,2′-((1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid)

“…They may be treated as useful tools in organic synthesis since they are small and easy to functionalize molecules that can be utilized to design novel bioactive compounds. It has been proven that these synthetic products exhibit antibacterial [1][2][3][4][5][6][7][8], antifungal [7][8][9][10][11][12][13][14][15][16], antitubercular [3], anticancer [3,6,17,18], antileucemic [5], antinflammatory [19][20][21], antiviral [22], anticonvulsant [1], antioxidant [2,7], and antiandrogenic [23,24] properties. They may act as inhibitors of p38 MAP kinases [25], protein kinase C [26], and protein-tyrosine phosphatase 1B, which consequently cause antiobesity effect [27,28].…”