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MOLECULES · 2023 ·Vol. 28 ·期 12 ·4774 · IF 4.6

Enantioselective Toxic Effects of Prothioconazole toward Scenedesmus obliquus

Qingqing Xiang,Ying Zhou,Chengxia Tan

Prothioconazole (PTC) is a broad-spectrum triazole fungicide with one asymmetric center and consists of two enantiomers,R-(−)-PTC andS-(+)-PTC. To address the concern of its environmental safety, the enantioselective toxic effects of PTC onScendesmus obliquus(S. obliquus) were investigated. PTC racemates (Rac-PTC) and enantiomers exhibited dose-dependent acute toxicity effects againstS. obliquusat a concentration from 1 to 10 mg·L−1. The 72 h-EC50 value ofRac-,R-(−)-, andS-(+)-PTC is 8.15, 16.53, and 7.85 mg·L−1, respectively. The growth ratios and photosynthetic pigment contents of theR-(−)-PTC treatment groups were higher than theRac- andS-(+)-PTC treatment groups. Both catalase (CAT) activities and esterase activities were inhibited in theRac- andS-(+)-PTC treatment groups at high concentrations of 5 and 10 mg·L−1, and the levels of malondialdehyde (MDA) were elevated, which exceeded the levels in algal cells for theR-(−)-PTC treatment groups. PTC could disrupt the cell morphology ofS. obliquusand induce cell membrane damage, following the order ofS-(+)-PTC ≈Rac-PTC >R-(−)-PTC. The enantioselective toxic effects of PTC onS. obliquusprovide essential information for its ecological risk assessment.Keywords:prothioconazole;toxicity effects;Scenedesmus obliquus;enantioselectivity

CAS / MDL: 67-68-5
研究领域: 环境科学 · 毒理学 · 生态学
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Applied Nanoscience · 2022 ·Vol. 12 ·期 9 ·2683-2693 · IF 3.869

Fabrication and applications of a microencapsulated prothioconazole based on β-cyclodextrin

Chi Yu,Ye Zhenghe,Su Xianyan,Li Zhao,Ren Xuexiang

In this work, a compound was fabricated using β-cyclodextrin (β-CD) and propithiumazole (PTC). FTIR and TG were used to analyze the intermolecular force and thermal stability of the compound and results indicated. The intermolecular forces were van der Waals forces. According to previous research, the seed coat agent and suspension concentrate (SC) were prepared using this compound and auxiliary. The inhibitory effect on Fusarium graminearum was studied with a bioassay. The data suggested inhibition rate of microencapsulated PTC are about 7.8% and 5% higher than PTC at 72 h and 192 h, respectively. In addition, results of pot experiments suggested dry weight of crops were increased after using seed coat agent contained microencapsulated prothioconazole which indicates that the seed coat agent may be beneficial to protein synthesis. Compared to commercial PTC, field experiments were conducted to investigate the preventive effects of SC against fusarium head blight (FHB). The results of toxicity test and field experiment showed that this compound can improve the utilization efficiency about 5% of PTC and reduce pesticide injury to wheat seeds.

CAS / MDL: 7585-39-9 11138-66-2
研究领域: 植物保护 · 农药科学
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FOOD CHEMISTRY · 2023 · IF 8.8

Determination of chiral prothioconazole and its chiral metabolite in water, juice, tea, and vinegar using emulsive liquid–liquid microextraction combined with ultra-high performance liquid chromatography

Xingle Guo,Xiaojiao Zheng,Xu Guo,Junxue Wu,Xu Jing

Emulsive liquid–liquid microextraction (ELLME), a simple, rapid, and environmentally friendly technique, was established to identify chiral prothioconazole and its chiral metabolite in water, juice, tea, and vinegar using ultra-high-performance liquid chromatography (UPLC). Environmentally friendly extractant was mixed with pure water to prepare a high-concentration emulsion, which was added to samples to complete the emulsification and extraction in 1 s. Afterward, an electrolyte solution was added to complete the demulsification without centrifugation. ELLME did not use dispersants compared to the familiar dispersive liquid–liquid microextraction (DLLME), thus reducing the use of toxic solvents and avoiding the effect of dispersants on the partition coefficient. The linear range was from 0.01 to 1 mg/L. The limit of detection was 0.003 mg/L. The extraction recoveries ranged from 82.4 % to 101.6 %, with relative standard deviations of 0.7–5.2 %. The ELLME method developed has the potential to serve as an alternative to DLLME.

研究领域: 分析化学 · 环境科学 · 食品科学
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PEST MANAGEMENT SCIENCE · 2025 · IF 3.8

Pesticide–fertilizer interactions: nutrient effects on wheat detoxification of prothioconazole

Linlin Shi,Lei Yang,Zixuan Yan,Chang Xu,Wenhui Li,Tingting Wang,Quan Gao,Min Liao,Haiqun Cao,Qingkui Fang

Background Prothioconazole (PTC), a triazole fungicide, and its metabolite prothioconazole-desthio (dPTC) present potential phytotoxic risks in crops. However, the mechanisms governing their uptake and detoxification in wheat remain unknown. This study aimed to determine how macronutrients and endogenous signaling compounds regulate PTC absorption and metabolism in wheat seedlings. Results High potassium availability markedly enhanced PTC uptake, resulting in a > 600% increase in PTC uptake over 12 h compared to the low potassium. Exogenous application of indole-3-acetic acid and brassinolide led to significant increases in PTC accumulation by 121.7% and 94.4%, respectively. Transcriptomic analysis revealed that PTC activated detoxification pathways, with prominent up-regulation of adenosine triphosphate (ATP)-binding cassette transporters and mitogen-activated protein kinase (MAPK) signaling components. Under nitrogen-deficient conditions, 1493 genes were specifically down-regulated, including those related to ribosome biogenesis, phenylalanine metabolism, and membrane transport, indicating a reduced detoxification capacity and enhanced dPTC retention. Conclusion Nitrogen availability plays a pivotal role in modulating the molecular response of wheat to PTC exposure. Nitrogen deficiency markedly down-regulated key genes involved in detoxification processes, thereby aggravating PTC-induced phytotoxicity. These results underscore the critical interplay between nutrient status and pesticide metabolism, providing mechanistic evidence to inform integrated pesticide–fertilizer management strategies aimed at minimizing chemical residues in food crops and enhancing agroecosystem sustainability. © 2025 Society of Chemical Industry.

CAS / MDL: 64-18-6
研究领域: 植物生理学 · 农药代谢 · 作物营养 · 分子生物学 · 环境毒理学 · 农业可持续性
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Thiosulfonates Based on Prothioconazole for Enhancing Antifungal Activity and Mitigating Phytotoxicity in Plant Pathogen Management

Guangyao Yan,Jianhua Xiao,Gang Tang,Yulu Liu,Xiaohong Zhang,Gaohua Hu,Yuqi Huang,Weiyao Yan,Qing Guo,Jiawei Shi,Ruyue Han,Yongqian Liang,Xiaohan Meng,Yongsong Cao

Prothioconazole (Prot) has been widely used for over two decades in controlling cereal diseases. However, the continuous emergence of resistance in plant pathogens has necessitated the development of novel fungicides. Thiosulfonate compounds have great application prospects due to their unique structural features and multisite activity. Herein, 25 novel Prot-based thiosulfonates were synthesized, and related antifungal activities were evaluated. Among them, 17 arylthiosulfonates exhibited better antifungal efficacy against Fusarium graminearum (EC50 = 0.07–0.22 mg/L) than Prot (EC50 = 0.41 mg/L). Interestingly, the most efficient compound, Tosyl-Prot (I-08) could be hydrolyzed to Prot in the environment and exhibited superior safety toward germination of wheat seed (86.67%) compared to Prot (0%). The antifungal mechanism of compound I-08 was demonstrated by disrupting the membrane integrity, inhibiting biomass accumulation, and suppressing multiple metabolic pathways. Therefore, Prot-based thiosulfonates would offer innovative strategies for the development of next-generation agricultural fungicides with multimodal actions and enhanced environmental compatibility.

研究领域: 农业化学 · 杀菌剂开发 · 植物病理学 · 环境毒理学 · 有机合成
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Bioactivity, Uptake, and Distribution of Prothioconazole Loaded on Fluorescent Double-Hollow Shelled Mesoporous Silica in Soybean Plants

Jingyuan Wang,Rong Li,Zongyuan Zhao,Meiqing Zhu,Yi Wang

Prothioconazole (PTC) has been widely utilized for plant fungal disease control, but its metabolite prothioconazole-desthio (PTC-d) exhibits reproductive toxicity. In the present study, carbon quantum dot (CQD)-modified fluorescent double-hollow shelled mesoporous silica nanoparticles (FL-MSNs) loaded with PTC, referred to as PTC@FL-MSNs, were constructed with an average size of 369 nm and a loading capacity of 28.1 wt %, which could increase the antifungal efficiency of PTC. In addition, upright fluorescence microscope and UPLC-MS/MS studies showed that PTC@FL-MSNs could be effectively transported via root uptake and foliar spray in soybean plants. Compared to a 30% PTC dispersible oil suspension agent, the PTC@FL-MSN treatment group showed higher concentrations (leaves: 0.50 > 0.48 mg/kg), longer half-lives for degradation (leaves: 3.62 > 3.21 d; roots: 3.39 > 2.82 d), and fewer metabolites. These findings suggest that sustained pesticide release and toxicity reduction are potential applications for PTC nanofungicide delivery technology.

CAS / MDL: 78-10-4
研究领域: 农学 · 纳米技术 · 植物病理学 · 环境科学
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Analytical Methods · 2024 · IF 2.7

Quantitative determination of prothioconazole in wheat grain, soybean, and pond water based on a polyclonal antibody

Zhihui Guo,Mingya Deng,Wenwen Fang,Kang Zheng,Min Liao,Yulong Wang,Qingkui Fang

Prothioconazole and its metabolite are considered a potential threat to human health and environmental safety. Thus, the development of a sensitive and rapid detection method for prothioconazole is crucial to ensure the safety of agricultural products. In this study, a new hapten of prothioconazole was designed and synthesized, and a selective polyclonal antibody with high affinity against prothioconazole was produced, which was obtained from immunized New Zealand white rabbits. Based on the polyclonal antibody, an indirect competitive enzyme-linked immunosorbent assay (ic-ELISA) and indirect competitive chemiluminescence enzyme immunoassay (ic-CLEIA) were developed for detecting prothioconazole pesticides. Under optimized experimental conditions, the limit of quantification (LOQ) values for ic-CLEIA and ic-ELISA were 1.8 and 10.7 ng mL−1, respectively. The results demonstrated that the sensitivity (LOQ) achieved by ic-CLEIA was more than five times higher compared to that obtained with ic-ELISA. In addition, the recoveries obtained by adding standard prothioconazole to wheat grain, soybean, and pond water samples were in the range of 81.9 to 104.7% for ic-ELISA and 89.0 to 118.0% for ic-CLEIA.

研究领域: 农业化学 · 环境科学 · 分析化学 · 毒理学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2022 · IF 4.966

NMR-based metabolomics approach to assess the ecotoxicity of prothioconazole on the earthworm (Eisenia fetida) in soil

Xin Bao,Wangjin Xu,Jiajia Cui,Zixin Yan,Jianjun Wang,Xiaojun Chen,Zhiyuan Meng

Prothioconazole (PTC) is a widely used agricultural fungicide . In recent years, studies have confirmed that it exerts adverse effects on various species, including aquatic organisms , mammals, and reptiles. However, the toxicological effects of PTC on soil organisms are poorly understood. Here, we investigated the toxic effects, via oxidative stress and metabolic responses, of PTC on earthworms ( Eisenia fetida ). PTC exposure can induce significant changes in oxidative stress indicators, including the activities of superoxide dismutase (SOD) and catalase (CAT) and the content of glutathione (GSH), which in turn affect the oxidative defense system of earthworms. In addition, metabolomics revealed that PTC exposure caused significant changes in the metabolic profiles of earthworms. The relative abundances of 16 and 21 metabolites involved in amino acids , intermediates of the tricarboxylic acid (TCA) cycle and energy metabolism were significantly altered after 7 and 14 days of PTC exposure, respectively. Particularly, Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway analysis showed that multiple different metabolic pathways could be disturbed after 7 and 14 days of PTC exposure. Importantly, these alterations in oxidative stress and metabolic responses in earthworms reveal that the effects of PTC on earthworms were time dependent, and vary with exposure time. In conclusion, this study highlights that the effects of PTC on soil organisms are of serious concern.

CAS / MDL: 7789-20-0
研究领域: 环境科学 · 毒理学 · 代谢组学 · 土壤生态学
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