Synthesis of 3-Substituted Isoxazolecarboxamides as Potential Fungicides

Gucma, Mirosław; Golebiewski, W. Marek; Morytz, B.; Charville, Hayley; Whiting, Andrew

doi:10.2174/157017810793362235

Cited by 6 publications

(3 citation statements)

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“…Structures of isoxazole derivatives showing fungicidal activity previously described by our group are displayed in Figure . Those compounds include amides: 4‐pyridine ( N ‐aryl)‐3‐aryl‐5‐isoxazolecarboxamides ( 4 , 5 ) (Gucma, Gołębiewski, & Michalczyk, ; Gucma, Gołębiewski, Morytz, Charville, & Whiting, ), 4‐pyridine‐3‐aryl (3‐alkyl)‐2‐isoxazoline‐carboxamides ( 8 , 9 ) (Gucma, Gołębiewski, & Michalczyk, ; Gucma, Gołębiewski, Morytz, et al, ), ( N ‐aryl)‐3‐aryl‐2‐isoxazoline‐5‐carboxamides ( 6 , 7 ) (Gucma & Gołębiewski, ), 3‐aryl‐2‐isoxazoline‐5‐carboxylic acid 10 (Gucma, Gołębiewski, & Michalczyk, ), 3‐aryl‐2‐isoxazoline‐ester derivatives: cycloadducts of 4‐trifluoromethylbenzonitrile oxide to methyl (2 E )‐3‐[(4 S )‐4‐(prop‐1‐en‐2‐yl)cyclohex‐1‐en‐1‐yl]prop‐2‐enoate 11 (Gucma, Gołębiewski, & Michalczyk, ), to methyl E ‐3‐bicyclo[2.2.1]hept‐5‐en‐2‐ylprop‐2‐enoate 12 (Gucma et al, ), and a cycloadduct of 4‐trifluoromethylbenzonitrile oxide to sesquiterpene C 15 trans , trans , trans ‐2,6,6,9‐tetramethyl‐1,4,8‐cycloundecatriene 13 (Gucma et al, ).…”

Section: Resultsmentioning

confidence: 99%

“…Structures of isoxazole derivatives showing fungicidal activity previously described by our group are displayed in Figure 2. Those compounds include amides: 4-pyridine (N-aryl)-3-aryl-5-isoxazolecarboxamides (4, 5) (Gucma, Gołębiewski, & Michalczyk, 2010;Gucma, Gołębiewski, Morytz, Charville, & Whiting, 2010), 4-pyridine-3-aryl (3-alkyl)-2-isoxazoline-carboxamides (8, 9) (Gucma, Gołębiewski, & Michalczyk, 2010;Gucma, Gołębiewski, Morytz, et al, 2010), (N-aryl)-3-aryl-2-isoxazoline-5carboxamides (6, 7) , 3-aryl-2-isoxazoline-5-carboxylic acid 10 (Gucma, Gołębiewski, & Michalczyk, 2015), 3-aryl-2-isoxazoline-ester derivatives: cycloadducts of 4trifluoromethylbenzonitrile oxide to methyl (2E)-3-[(4S)-4-(prop-1en-2-yl)cyclohex-1-en-1-yl]prop-2-enoate 11 (Gucma, Gołębiewski, & Michalczyk, 2014),…”

Section: Methyl 5-methoxy-3-[4-(trifluoromethyl) Phenyl]-2-isoxazolmentioning

confidence: 99%

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The influence of the structure of various isoxazole derivatives on photosynthetic apparatus of tomato plants grown in the field and greenhouse. Effect of various stages of plant growth in different seasons

et al. 2018

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The aim of this study was to determine how various derivatives of isoxazole affect photosynthetic apparatus of different tomato species grown in a greenhouse and under field conditions. Measurements of chlorophyll fluorescence of photosystem II (PSII) were used as an indicator of the stress induced by isoxazoles on photosynthetic energy conversion. Chlorophyll fluorescence yield provides quantitative information not only on steady‐state photosynthesis, but also on various mechanisms of protection against stress‐induced damage and the extent to which performance of photosynthesis is limited by photochemical and non‐photochemical processes. Measurements were made on tomato plants in various stages of growth (from the 3rd to 15th leaf), in different seasons of the year. The data show that the age of plants does not have a significant influence on Fv/Fm values and it seems that younger plants are more sensitive to the used isoxazole derivatives. Selected isoxazoles did not affect the plant photosynthesis. Practical applications The isoxazole derivatives show inhibitory activity against growth of the fungus pathogens. The objective of this work was to test the ability of the chlorophyll fluorescence measurements as an indicator of the changes induced by isoxazole compounds on photosynthetic energy conversion of tomato plants. Regarding importance of tomato as a very popular and widely consumed all over the world vegetable, the effect of different isoxazole derivatives with different fungicidal activity on tomato plant was examined. The use of some of the tested isoxazolines due to their lack of toxicity for the plants is very promising.

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Section: Resultsmentioning

confidence: 99%

Section: Methyl 5-methoxy-3-[4-(trifluoromethyl) Phenyl]-2-isoxazolmentioning

confidence: 99%

The influence of the structure of various isoxazole derivatives on photosynthetic apparatus of tomato plants grown in the field and greenhouse. Effect of various stages of plant growth in different seasons

et al. 2018

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“…We carried out many cycloaddition reactions of 21 nitrile oxides to two unsaturated alcohols, 14 esters, and 12 amides mediated by complexes of lanthanides and other Lewis acids with chiral ligands obtaining products with variable regioselectivities and enantioselectivities up to 99%, including several biologically active carboxamides . Herein, we wish to present the results of a thorough analysis of the reaction mixtures that showed the presence of several side products, some of which were quite unexpected and interesting from the synthetic point of view.…”

Section: Introductionmentioning

confidence: 99%