Developmental toxicity and inhibition of the fungicide hymexazol to melanin biosynthesis in zebrafish embryos

Fan, Yongmei; Miao, Weiguo; Lai, Kehua; Huang, Weikang; Song, RuiXue; Li, Qing X.

doi:10.1016/j.pestbp.2017.10.007

Cited by 16 publications

(9 citation statements)

References 10 publications

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“…The fish embryo acute toxicity test (FET) with zebrafish embryos, which is a general model in ecotoxicology and toxicology had been established in our labs [ 15 , 16 ]. The mortality in the positive control was 40% greater than 30% and survival in the negative control was 100%.…”

Section: Resultsmentioning

confidence: 99%

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

et al. 2018

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In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL−1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL−1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

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Section: Resultsmentioning

confidence: 99%

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

et al. 2018

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“…Seed treatment with HML at 10.5–14 g/kg seed was recommended by Payne and William [ 8 ]. However, it is highly toxic to embryo fish and can cause cardiac edema, growth retardation, and swing abnormalities [ 9 ]. European Food Safety Authority (EFSA) has identified the HML hymexazol as a toxic agent for humans.…”

Section: Introductionmentioning

confidence: 99%

A Comprehensive Study on the Mechanistic Way of Hexaflumuron and Hymexazol Induced Neurobehavioral Toxicity in Rats

et al. 2022

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Pesticides are widely used in agriculture to kill pests, but their action is non-selective and results in several hazardous effects on humans and animals. Pesticide toxicity has been demonstrated to alter a variety of neurological functions and predisposes to various neurodegenerative diseases. Although, there is no data available for hexaflumuron (HFM) and hymexazol (HML) neurotoxicity. Hence, the present study aims to investigate the possible mechanisms of HFM and HML neurotoxicity. 21 male Wistar rats were divided into three groups and daily received the treatment via oral gavage for 14 days as follows: group (1) normal saline, group (2) HFM (1/100LD50), and group (3) HML (1/100 LD50). Our results revealed that both HFM and HML produced a significant increase in MDA levels and a decrease in GSH and CAT activity in some brain areas. There were severe histopathological alterations mainly neuronal necrosis and gliosis in different examined areas. Upregulation of mRNA levels of JNK and Bax with downregulation of Bcl-2 was also recorded in both pesticides exposed groups. In all studied toxicological parameters, HML produced neurotoxicity more than HFM. HFM targets the cerebral cortex and striatum, while HML targets the cerebral cortex, striatum, hippocampus, and cerebellum. We can conclude that both HFM and HML provoke neurobehavioral toxicity through oxidative stress that impairs the mitochondrial function and activates the JNK-dependent apoptosis pathway.

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“…Additionally, HYM can be directly absorbed by plant roots and metabolized quickly into two glycoside metabolites (Figure ), an N -connection hymexazol glucoside, 2-(β- d -glucopyranosyl)-5-methyl-4-isoxazoline-3-one, and an O -connection hymexazol glucoside, 3-(β- d -glucopyranosyl)-5-methylisoxazole. Interestingly, HYM O -glucoside has a weaker antifungal activity than HYM, and N -glucoside even has no antifungal ability. , This means that only a part of HYM can be converted into active antifungal molecules when HYM is absorbed in plants, which causes a decreased control efficiency. Therefore, the selective O -glycosylation of HYM could maintain the active structure in vitro and in vivo by simulating plant glycosylation of HYM in vitro.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy

Gao

Qin

Wang

et al. 2022

J. Agric. Food Chem.

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Hymexazol (HYM) is irreplaceable for treating soil-borne diseases due to its high efficiency and low cost, as a broad-spectrum fungicide. However, when HYM is absorbed by plants, it is rapidly converted into two glycoside metabolites, and the antifungal activities of these glycosides are inferior to that of HYM. Therefore, in this study, to maintain strong antifungal activity in vitro and in vivo, HYM was glycosylated with amino sugars that have diverse biological activities to simulate plant glycosylation. The antifungal experiment proved that glycoside 15 has the highest antifungal activity, and N-acetyl glucosamine and HYM had obvious synergistic effects. According to the structure–activity relationship studies, glycoside 15 had greater numbers of active electron-rich regions and front-line orbital electrons due to the introduction of N-acetyl glucosamine. Moreover, glycoside 15 can significantly promote plant growth and induce an increase in plant defense enzyme activity. Additionally, compared to HYM, the results of electron microscopy and proteomics revealed that glycoside 15 has a unique antifungal mechanism. The promising antifungal activity and interactions with plants mean that glycoside 15 is a potential green fungicide candidate. Furthermore, this research conducted an interesting exploration of the agricultural applications of amino sugars.

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Developmental toxicity and inhibition of the fungicide hymexazol to melanin biosynthesis in zebrafish embryos

Cited by 16 publications

References 10 publications

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

A Comprehensive Study on the Mechanistic Way of Hexaflumuron and Hymexazol Induced Neurobehavioral Toxicity in Rats

Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy

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