ELISA for the detection of the triazole fungicide myclobutanil.

Székacs, András; Hammock, Bruce D.

doi:10.1021/jf00056a024

Cited by 22 publications

(28 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Myclobutanil (MT), (RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl) hexanenitrile, is a typical triazole fungicide used for the control of powdery mildew and scabbing of plants. 5 Fungicidal action occurs through inhibition of the sterol 14-demethylase enzyme. 6 It has a single chiral center and consists of two enantiomers.…”

Section: ■ Introductionmentioning

confidence: 99%

Enantioselective Distribution, Degradation, and Metabolite Formation of Myclobutanil and Transcriptional Responses of Metabolic-Related Genes in Rats

Wang

Zhu

et al. 2018

Environ. Sci. Technol.

View full text Add to dashboard Cite

Myclobutanil (MT), a chiral fungicide, can be metabolized enantioselectively in organisms. In this work, the associated absorption, distribution, metabolism and transcriptional responses of MT in rats were determined following a single-dose (10 mg·kg body weight) exposure to rac-, (+)- or (-)-MT. The enantiomer fractions (EFs) were less than 0.5 with time in the liver, kidney, heart, lung, and testis, suggesting preferential enrichment of (-)-MT in these tissues. Furthermore, there was conversion of (+)-form to (-)-form in the liver and kidney after 6 h exposure to enantiopure (+)-MT. Enrichment and degradation of the two enantiomers differed between rac-MT and MT-enantiomers groups, suggesting that MT bioaccumulation is enantiomer-specific. Interestingly, the degradation half-life of MT in the liver with rac-MT treatment was shorter than that with both MT-enantiomer treatments. One reason may be that the gene expression levels of cytochrome P450 1a2 ( cyp1a2) and cyp3a2 genes in livers treated with rac-MT were the highest among the three exposure groups. In addition, a positive correlation between the expression of cyp2e1 and cyp3a2 genes and rac-MT concentration was found in livers exposed to rac-MT. Simultaneously, five chiral metabolites were detected, and the enantiomers of three metabolites, RH-9090, RH-9089, and M2, were separated. The detected enantiomers of (+)-MT metabolites were in complete contrast with those of (-)-MT metabolites. According to the results, a metabolic pathway of MT in male rats was proposed, which included the following five metabolites: RH-9089, RH-9090, RH-9090 Sulfate, M1, and M2. The possible metabolic enzymes were marked in the pathway. The findings of this study provide more specific insights into the enantioselective metabolic mechanism of chiral triazole fungicides.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Enantioselective Distribution, Degradation, and Metabolite Formation of Myclobutanil and Transcriptional Responses of Metabolic-Related Genes in Rats

Wang

Zhu

et al. 2018

Environ. Sci. Technol.

View full text Add to dashboard Cite

show abstract

“…Several antibody-based tests for triazole fungicides have been developed, including for triadimefon, tetraconazole, penconazole, myclobutanil, tebuconazole and hexaconazole (Chen, Dwyre-Gygax, Hadfield, Willetts, & Breuil, 1996;Danks, Chaudhry, Parker, Barker, & Banks, 2001;Forlani, Arnoldi, & Pagani, 1992;Newsome, 1986;Szekacs & Hammock, 1995). To date, no immunoassay for diniconazole has been reported.…”

Section: Introductionmentioning

confidence: 99%

Development of an enzyme-linked immunosorbent assay for diniconazole in agricultural samples

Jiang

Shi

et al. 2011

Food Chemistry

View full text Add to dashboard Cite

“…The pH value may play a significant role in molecular adsorption onto metallic surfaces. 27 The p K a (logarithm of the dissociation constant) values of triazole 28 and MCB 29 are 2.2 and 2.3, respectively. We found that MCB exhibited strong SERS spectra in the Ag NPs only under acidic conditions at pH values below 5 (see Fig.…”

Section: Resultsmentioning

confidence: 99%

Interactions between the Antifungal Drug Myclobutanil and Gold and Silver Nanoparticles in Penicillium digitatum Investigated by Surface-Enhanced Raman Scattering

et al. 2014

View full text Add to dashboard Cite

Surface-enhanced Raman scattering (SERS) of an antifungal reagent, myclobutanil (MCB), was performed on Au and Ag nanoparticles (NPs) to estimate the drug-release behaviors in fungal cells. A density functional theory (DFT) calculation was introduced to predict a favorable binding site of MCB to either the Ag or Au atom. Myclobutanil was presumed to bind more strongly to Au than to Ag in their most stable, optimized geometries of the N4 atom in its 1,2,4-triazole unit binding to the metal atom. Strong intensities were observed in the Ag SERS spectra only at acidic pH values, whereas the most prominent peaks in the Au SERS spectra of MCB matched quite well with those of 1,2,4-triazole regardless of pH conditions. The Raman spectral intensities of the MCB-assembled Ag and Au NPs decreased after treatment with either potato dextrose agar (PDA) or glutathione (GSH). Darkfield microscopy and confocal SERS were performed to analyze the MCB-assembled metal NPs inside Penicillium digitatum fungal cells. The results suggested that MCB was released from the metal NPs in the intracellular GSH in the fungi because we observed only fungal cell peaks.

show abstract

ELISA for the detection of the triazole fungicide myclobutanil.

Cited by 22 publications

References 28 publications

Enantioselective Distribution, Degradation, and Metabolite Formation of Myclobutanil and Transcriptional Responses of Metabolic-Related Genes in Rats

Enantioselective Distribution, Degradation, and Metabolite Formation of Myclobutanil and Transcriptional Responses of Metabolic-Related Genes in Rats

Development of an enzyme-linked immunosorbent assay for diniconazole in agricultural samples

Interactions between the Antifungal Drug Myclobutanil and Gold and Silver Nanoparticles in Penicillium digitatum Investigated by Surface-Enhanced Raman Scattering

Contact Info

Product

Resources

About