Oxazole and Isoxazole Chemistry in Crop Protection

Lamberth, Clemens

doi:10.1002/jhet.3252

Cited by 69 publications

(30 citation statements)

References 51 publications

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“…The fungicidal group, benzamide, constrains the development of unwanted wild plants linked with agronomical growth like onion, potato, corn, and ginseng [ 1 ]. Zoxamide, (RS)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-p-toluamide, is applied on weeds and grasses as a preemergent pest control with an administration degree of 5 L/ha [ 2 ]. Zoxamide, a relatively recent fungicide, operates by countering the oomycetes [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

[Retracted] Effective Remediation Strategy for Xenobiotic Zoxamide by Pure Bacterial Strains, Escherichia coli, Streptococcus pyogenes, and Streptococcus pneumoniae

Ahmad

Sajid

Gul

et al. 2020

BioMed Research International

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Zoxamide, a class IV hazardous fungicide, is perilous for the environment due to its highly persistent nature. Up till the current date, there are no reports on the biodegradation of zoxamide. The scarcity of knowledge in this domain led to the present research to evaluate the biodegradation of this benzamide fungicide by three bacterial strains, Escherichia coli (EC), Streptococcus pyogenes (SPy), and Streptococcus pneumoniae (SP). Biotransformation of zoxamide was scrutinized in nutrient broth assemblies for a period of 28 days followed by UV-visible spectrophotometer and GC-MS analysis of the metabolites. The results exhibited a low to medium biodegradation potential of the bacterial cells to metabolize zoxamide. The highest biotransformation percentage was observed by E. coli to be 29.8%. The order of half-life calculated for the degradation results was EC 42.5 < SPy 58.7 < SP 67.9 days. GC-MS analysis indicated the formation of several metabolites including, 2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyl-4H-1,3-oxazin-5(6H)-one, 3,5-dichloro-N-(3-hydroxy-1-ethyl-1-methyl--2-oxopropyl)-4-methylbenzamide and 3,5-dichloro-4-methylbenzamide. The research could influence the biotreatment strategies for the environmentally friendly eradication of xenobiotics.

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Section: Introductionmentioning

confidence: 99%

[Retracted] Effective Remediation Strategy for Xenobiotic Zoxamide by Pure Bacterial Strains, Escherichia coli, Streptococcus pyogenes, and Streptococcus pneumoniae

Ahmad

Sajid

Gul

et al. 2020

BioMed Research International

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“…Acetic acid (0.05 mmol) was added and the components were mixed thoroughly and ground well with a pestle at room temperature under neat conditions for appropriate time as indicated in Table 1. The progress of the reaction was monitored by TLC using ethyl acetate: (m, 1H, Ar), 7.10 to 7.09 (m, 1H, Ar), 6.91 to 6.88 (m, 2H, Ar), 1.58 (s, 1H, NH), 1.05 to 1.01 (m, 3H, CH 3 ); 13…”

Section: Methodsmentioning

confidence: 99%

“…3H, CH 3 );13 C NMR (400 MHz, DMSO): 189.27, 178.25, 162.13, 157.65, 157.13, 147.83, 143.03, 135.82, 134.38, 133.17, 132.52, 131.12, 126.36, 121.10, 120.70, 120.13, 109.86, 105.06, 94.88, 46.70, 9.17; HRMS (ESI) m/z Calculated for [M + H] + : 401.0886, found: 401.0891.…”

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confidence: 99%

Acetic acid catalysed solvent‐free synthesis of spiro‐isoxazolo[5,4‐b]pyridines/quinolines by mechano‐chemical grinding

Jindal

Meena

Magoo

2020

Journal of Heterocyclic Chem

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A simple and efficient three-component procedure has been developed for the synthesis of a series of spiro-isoxazolo[5,4-b]pyridines/quinolines by one-pot condensation of isatins, 3-methylisoxazol-5-amine and enolizable cyclic carbonyl compounds. The protocol has been accomplished under solvent-free conditions by grinding the components at room temperature in presence of catalytic CH 3 COOH. The described process offers environmentally benign reaction conditions for the synthesis of pharmacologically important spirooxindole fused heterocycles with the advantages ofoperational simplicity, short reaction time and good to excellent yields of isolated pure product.

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“…A widely used isoxazole ring synthesis steategy is 1,3‐dipolar cycloaddition of alkenes and alkynes with nitrile oxides and the reaction of hydroxylamine with a three‐carbon atom component, such as 1,3‐diketone or α,β‐unsaturated ketone (or similar chemical structure such as enaminone, enaminonitrile etc.) [67,68] . Because of its relatively easy synthesis, isoxazole ring has been as an object of interest for releated research groups all over the world.…”

Section: Formation Of Heterocycle Structures By Dmf‐dma Reactionsmentioning

confidence: 99%

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Gümüş

Koca

2020

ChemistrySelect

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N,N‐Dimethylformamide dimethyl acetal (DMF‐DMA) reagent can react with different functional groups of organic compounds. Enamines and dimethylamino imines are obtained, when the DMF‐DMA reagent is reacted with methylene, methyl and amino groups. These products are formed in the intermediate step in the synthesis of many hetero rings. These compounds are especially used as a starting material in the synthesis of heterostructures such as pyrimidine, pyridine, pyrazole, etc. Therefore, DMF‐DMA has been particularly prominent as a reagent in targeted synthesis and designs of many heterocyclic compounds. Herein, the reactions of DMF‐DMA reagent with different functional groups are categorized in four classes (methylene, methyl, amino, other groups) and the reactions of obtained enamine and dimethylamino imine compounds are investigated in detail such as nucleophilic addition, intramolecular cyclization or condensation reactions. The synthesis and continuation reactions of the enamine and dimethylamino imine compounds are also examined in terms of experimental conditions and reagents used.

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Oxazole and Isoxazole Chemistry in Crop Protection

Cited by 69 publications

References 51 publications

[Retracted] Effective Remediation Strategy for Xenobiotic Zoxamide by Pure Bacterial Strains, Escherichia coli, Streptococcus pyogenes, and Streptococcus pneumoniae

[Retracted] Effective Remediation Strategy for Xenobiotic Zoxamide by Pure Bacterial Strains, Escherichia coli, Streptococcus pyogenes, and Streptococcus pneumoniae

Acetic acid catalysed solvent‐free synthesis of spiro‐isoxazolo[5,4‐b]pyridines/quinolines by mechano‐chemical grinding

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

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