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MOLECULES · 2024 ·Vol. 29 ·期 6 ·1353 · IF 4.2

In Vitro and Ex Vivo Antifungal Activities of Metconazole against the Rice Blast Fungus Pyricularia oryzae

Liwang Fei,Lingyun Hao

Rice blast, caused by the filamentous fungusPyricularia oryzae, has long been one of the major threats to almost all rice-growing areas worldwide. Metconazole, 5-(4-chlorobenzyl)-2, 2-dimethyl-1-(1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol, is a lipophilic, highly active triazole fungicide that has been applied in the control of various fungal pathogens of crops (cereals, barley, wheat), such as theFusariumandAlternariaspecies. However, the antifungal activity of metconazole againstP. oryzaeis unknown. In this study, metconazole exhibited broad spectrum antifungal activities against sevenP. oryzaestrains collected from rice paddy fields and the wild type strain P131. Scanning electron microscopic analysis and fluorescein diacetate staining assays revealed that metconazole treatment damaged the cell wall integrity, cell membrane permeability and even cell viability ofP. oryzae, resulting in deformed and shrunken hyphae. The supplementation of metconazole in vitro increased fungal sensitivity to different stresses, such as sodium dodecyl sulfate, congo red, sodium chloride, sorbitol and oxidative stress (H2O2). Metconazole could inhibit key virulence processes ofP. oryzae, including conidial germination, germ tube elongation and appressorium formation. Furthermore, this chemical preventedP. oryzaefrom infecting barley epidermal cells by disturbing appressorium penetration and subsequent invasive hyphae development. Pathogenicity assays indicated a reduction of over 75% in the length of blast lesions in both barley and rice leaves when 10 μg/mL of metconazole was applied. This study provides evidence to understand the antifungal effects of metconazole againstP. oryzaeand demonstrates its potential in rice blast management.

CAS / MDL: 7558-80-7 125116-23-6
研究领域: 植物病理学 · 农学
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LANGMUIR · 2025 · IF 3.9

Development of a pH/Cellulase Dual-Responsive Fe-MOFs Delivery System for Targeted Control of Maize Fungal Diseases

Yuanbo Li,Taiming Zhang,Yanru Ding,Yuhao Chen,Yukui Rui

The iron-based metal–organic frameworks (Fe-MOFs) NH2-MIL-101(Fe) (MIL) has gained widespread attention as a drug carrier material in agriculture. In this study, a multifunctional nanocomposite, MIL@A@D@C, was successfully synthesized by loading the fungicide azoxystrobin (AZOX) and immunoinducer d-cellobiose (D) onto MIL, followed by surface modification with carboxymethyl cellulose (CMC). The loading capacity of MIL was optimized by varying solvent conditions and the mass ratio of MIL to AZOX, revealing that ethanol as the reaction solvent and a MIL: AZOX mass ratio of 1:4 resulted in the highest loading efficiency (6.73%). MIL@A@D@C exhibited pH- and cellulase-responsive controlled release behavior. In vitro antifungal assays demonstrated that MIL@A@D@C at a low concentration of 1 ppm effectively inhibited Colletotrichum graminicola (the causal agent of maize anthracnose). Foliar application experiments further confirmed that the composite formulation achieved significant inhibition at a low dosage of 10 ppm, outperforming commercial azoxystrobin products. Plant and animal safety assessments indicated that MIL@A@D@C possessed enhanced biosafety. These findings highlight the potential of MIL@A@D@C as an environmentally friendly and highly effective nanodelivery system for crop disease management.

研究领域: 农业纳米技术 · 植物病理学 · 药物递送系统 · 材料科学 · 环境科学
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PEST MANAGEMENT SCIENCE · 2022 ·Vol. 79 ·期 1 ·114-124 · IF 4.462

Conversion of fungicide cyprodinil to salts with organic acids: preparation, characterization, advantages

Qiuxiao Wang,Tao Wang,Yifei Zhou,Haixiang Gao

BACKGROUND As an effective strategy to improve the basic properties of drugs, salt formation was less used in the field of pesticides than the medicine field. It is worth trying to improve the inherent shortcomings of cyprodinil (high K ow values; polymorphism) in this way to enhance its practicality. RESULTS Eight cyprodinil salts (CYP-Salts) were prepared. The properties of CYP-Salts, including solubility in various solvents, polymorphic behavior, soil absorption, photolysis in aquatic water, in vitro fungicidal activity and curative activity, were assessed. It was observed that compared with those of cyprodinil, CYP-Salts had lower soil adsorption, while also having lower log K ow values and could be more easily photodegraded in water. That is, CYP-Salts have lower impacts on water bodies and aquatic organisms than cyprodinil. Three CYP-Salts showed higher in vitro antifungal activities and curative activity. CYP-Salts have enhanced practicality, as they could avoid possible agglomeration caused by recrystallization. CONCLUSION Salt forming enhanced the properties of Cyprodinil in many aspects. CYP-Salts may potentially become a better substitute for cyprodinil. This study offers a more economical and effective strategy to prepare better alternatives to existing fungicides. © 2022 Society of Chemical Industry.

研究领域: 农药化学 · 环境科学 · 药学
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BIOMEDICAL CHROMATOGRAPHY · 2024 ·Vol. 38 ·期 9 ·e5935 · IF 1.8

Simultaneous determination of four fungicide residues in figs using liquid chromatography tandem mass spectrometry

Feng Lan,Xinyu Wang,Xuejing Wang,Yinwei Ruan,Li Ding,Daliang Liu,Tongliang Zhang,Jianping Wang

Dissipative behavior and final residue levels of difenoconazole, prochloraz, propiconazole, and pyraclostrobin in figs were investigated using field trials and laboratory assays. A three-factor, three-level orthogonal test was designed to optimize the pretreatment conditions of the method. A method was established using high-performance liquid chromatography tandem mass spectrometry for the determination of difenoconazole, prochloraz, propiconazole, and pyraclostrobin residues in figs. The limit of quantification for all four targets in figs was 0.002 mg/kg. Difenoconazole, prochloraz, propiconazole, and pyraclostrobin are readily digestible pesticides in figs with half-lives of 6.4, 6.2, 4.8, and 7.9 days, respectively. Residues of difenoconazole, prochloraz, propiconazole, and pyraclostrobin in figs were below the European Union established residue levels of 0.1, 0.03, 0.01, and 0.02 mg/kg, respectively, at day 7 after application. Pyraclostrobin, propiconazole, difenoconazole, and prochloraz were applied twice at doses of 75, 125, 150, and 200 mg a.i./kg at 7-day intervals, and the residues of the four fungicides in figs were acceptable 7 days after the last application. Therefore, the safety interval can be set at 7 days for 70% difenoconazole-prochloraz wettable powder and 40% pyraclostrobin-propiconazole aqueous emulsion according to the protocol.

CAS / MDL: 64-18-6
研究领域: 食品科学 · 分析化学 · 植物保护
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ENVIRONMENT INTERNATIONAL · 2019 · IF 7.943

The fungicide azoxystrobin perturbs the gut microbiota community and enriches antibiotic resistance genes in Enchytraeus crypticus

Qi Zhang,Dong Zhu,Jing Ding,Fei Zheng,Shuyidan Zhou,Tao Lu,Yong-Guan Zhu,Haifeng Qian

The use of pesticides to ensure global food security is the most important pest control strategy in modern agriculture but causes extensive soil pollution. This pollution involves potential risks to human health and ecosystems. In addition to soil animal growth, the adverse impact of pesticides on the gut microbiomes of nontarget soil fauna remains largely unknown. Here, the effect of the fungicide azoxystrobin (AZ) on soil and the gut microbiota of soil animals ( Enchytraeus crypticus ) was studied. The tested concentrations of AZ altered the bacterial community in the soil and E. crypticus gut and were slightly toxic with respect to E. crypticus adult mortality and reproduction. The most abundant bacterial phylum, Proteobacteria, significantly increased in response to the 2 and 5 mg/kg AZ treatments, which implied a disordered unhealthy gut bacterial community. Furthermore, bacterial community analysis between the soil and gut showed that the main effect of AZ on the gut microbiota was directly through AZ, not soil microbiota. In addition, AZ exposure significantly enhanced the number and total abundance of antibiotic resistance genes (ARGs) in the E. crypticus gut; these genes may enter the soil food web to affect higher trophic levels and cause a more serious ecological risk. Our study reported the effect of pesticides on the gut of soil animals and on the enrichment of ARGs as global emerging contaminants, revealing unknown potential impacts of fungicides on ecosystem services and sustainable food production.

研究领域: 环境科学 · 微生物学 · 生态毒理学 · 土壤学
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2013 · IF 2.487

Ultrasound-assisted surfactant-enhanced emulsification microextraction with solidification of floating organic droplet followed by high performance liquid chromatography for the determination of strobilurin fungicides in fruit juice samples

Pei Liang,Guojiao Liu,Fang Wang,Wanting Wang

A novel method, ultrasound-assisted surfactant-enhanced emulsification microextraction with solidification of floating organic droplet (UASEME-SFOD), has been developed for the extraction of four strobilurin fungicides (kresoxim-methyl, picoxystrobin, pyraclostrobin and trifloxystrobin) in fruit juices. In the UASEME-SFOD technique, Tween 80 was used as emulsifier, and 1-undecanol was used as extraction solvent without using any organic dispersive solvent. Several parameters that affect the extraction efficiency, such as the kind and volume of extraction solvent, the type and concentration of the surfactant, extraction time, extraction temperature and salt addition were investigated and optimized. Under the optimum extraction condition, the method yields a linear calibration curve in the concentration range from 5 to 10,000   ng   mL −1 for the targeted analytes with the correlation coefficient ranging from 0.9991 to 0.9998. The enrichment factors were in the range between 95 and 135, and the limits of detection of the method were 2–4   ng   mL −1 . The fruit juice samples were successfully analyzed using the proposed method, and the relative recoveries at fortified levels of 50 and 100   ng   mL −1 were in the range of 82.6–97.5%.

CAS / MDL: 112-53-8 112-42-5
研究领域: 分析化学 · 食品科学
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Environmental Science-Nano · 2023 · IF 7.3

Antifungal activity and mechanisms of AgNPs and their combination with azoxystrobin against Magnaporthe oryzae

Huanbin Shi,Hui Wen,Shuwei Xie,Yuan Li,Ya Chen,Zhiquan Liu,Nan Jiang,Jiehua Qiu,Xueming Zhu,Fucheng Lin,Yanjun Kou

Silver nanoparticles (AgNPs) exhibit a broad spectrum of antimicrobial activity against various fungal pathogens, including the devastating rice blast fungus Magnaporthe oryzae, which threatens rice production worldwide. However, the antifungal molecular mechanisms of AgNPs against M. oryzae are still poorly understood. Here, it was found that the mycelial growth and virulence of M. oryzae strains were significantly reduced by AgNPs. Two nm-AgNPs at an EC50 concentration of 2.0 μg mL−1 almost impaired 100% virulence of M. oryzae. Further studies revealed that AgNP treatment changes cell wall morphology and suppresses appressorium formation. The defects in appressorium development upon AgNP treatment were caused by the reduced phosphorylation level of the MAPK MoPmk1 and impaired conidial autophagy. Importantly, the combination of AgNPs and azoxystrobin at appropriate ratios enhanced fungitoxicity to azoxystrobin-sensitive/resistant M. oryzae strains. Due to the excellent control effect of AgNPs on rice blast, we established a method for the biosynthesis of AgNPs by using the biocontrol Bacillus strain Tu27 to reduce waste environmental pollution and synthesis costs. Infection assays showed that the biosynthesized AgNPs displayed similar fungal toxicity. Taken together, our results revealed that AgNPs display the antifungal activity by a unique mechanism of damaging cell wall integrity, reducing phosphorylation of the MAPK MoPmk1, and impairing autophagy, and have an additive synergy with azoxystrobin on M. oryzae.

研究领域: 植物病理学 · 分子生物学 · 纳米技术 · 农业科学
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EUROPEAN JOURNAL OF PLANT PATHOLOGY · 2023 · IF 1.8

Effect of azoxystrobin on the physiology, morphology, and sclerotial formation of Rhizoctonia solani from tobacco

Xiang Ligang,Yu Zhihe,Wang Hancheng,Cai Liuti,Hsiang Tom,Li Wenhong,Guo Moyan,Li Tong,Sun Meili

Tobacco, as one of the major cash crops in Guizhou province, China, is severely affected by diseases caused by Rhizoctonia solani . Azoxystrobin is a quinone outside inhibitor (QoI) fungicide extensively used to control various crop diseases in China. To evaluate the potential effect of azoxystrobin on the physiology, morphology, and sclerotial formation of Rhizoctonia solani , 104 isolates of R. solani from tobacco collected in Guizhou were evaluated for in vitro sensitivity to azoxystrobin, and scanning electron microscopy was used to observe the effects of azoxystrobin on mycelial morphology. The effects of azoxystrobin on reactive oxygen species (ROS), superoxide dismutase (SOD), catalase (CAT), and succinate dehydrogenase (SDH) in hyphae at three time points (at 5, 10 and 15 days) and on sclerotial differentiation were examined. The effective concentration that caused 50% growth inhibition (EC 50 ) ranged from 0.3 to 552 μg/mL with a geometric mean of 8.4 μg/mL, and the frequency distribution of EC 50 values was unimodal. Scanning electron microscopy revealed that azoxystrobin caused folding, collapse and crumpling of hyphae. Under azoxystrobin stress, sclerotial differentiation was inhibited, and the production of hydrogen peroxide (H 2 O 2 ) and superoxide anion (O 2− ) as well as activities of SOD, CAT and SDH in hyphae increased significantly compared to the untreated control at day 5; while at day 10 or 15, H 2 O 2 production decreased significantly, CAT activity increased significantly, and O 2− , SOD, and SDH concentrations returned to normal levels. In general, the results provide a better understanding of the physiological effects of azoxystrobin on R. solani .

CAS / MDL: 89-73-6
研究领域: 植物病理学 · 真菌生物学 · 农业科学
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FOOD CHEMISTRY · 2022 · IF 9.231

Magnetic deep eutectic solvent-based dispersive liquid–liquid microextraction for enantioselectively determining chiral mefentrifluconazole in cereal samples via ultra-high-performance liquid chromatography

Xu Jing,Haoyue Xue,Xiaoyan Sang,Xiaowen Wang,Liyan Jia

A simple, rapid, and efficient pretreatment method of mefentrifluconazole enantiomers in cereal samples was established by dispersive liquid–liquid microextraction coupled with ultra-high-performance liquid chromatography-diode array detector (UHPLC-DAD). In this study, a novel ternary magnetic deep eutectic solvent (MDES) [octyltrimethylammonium bromide][cobalt chloride][acetic acid] was synthesized as the extractant. Acetic acid was used as the dispersant to promote the in situ dispersion of binary MDES [octyltrimethylammonium bromide][cobalt chloride]. The microdroplets of binary MDES containing mefentrifluconazole were separated by an external magnet. Device-assisted dispersion and time-consuming centrifugation steps were eliminated to ensure simplicity and rapidity of the pretreatment. Good linearity ranging from 0.01 μg g −1 to 2 μg g −1 was obtained. The extraction recovery varied from 82.9 to 95.0%. The limit of detection was 0.003 μg g −1 . Finally, this established approach has been applied for the enantioselective detection of chiral mefentrifluconazole in corn, rice, wheat, millet, and sorghum samples.

研究领域: 分析化学 · 农业化学 · 食品科学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Rationally designing renewable plant oil-based polymers as efficient nanocarriers for sustained pesticide delivery

You Wang,Xiaomiao Xu,Xinzi Fang,Nan Yao,Handan Lei,Guang Yang,Zhongkai Wang,Yongcheng Dong,Zan Hua

Nanopesticides, which have great potential to revolutionize modern agriculture present the major forms of nanocarriers and loaded active ingredients (AIs) such as insecticides, fungicides or herbicides. Conventional petroleum-based polymers as nanocarriers with poor degradability have the potential detriment to human health and the environment. In contrast, efficient nanocarriers from renewable biomass could not only decrease the consumption of limited fossil resources, but also reduce the environmental concerns. However, the fabrication of highly efficient biomass-based nanocarriers for nanopesticides has rarely been explored owing to the limited functional groups and poor structural variations of biomass. In this work, we have reported four distinct amphiphilic renewable plant oil-based copolymers with the same chemical compositions and significantly different bottlebrush or linear molecular structures. They all have the renewable plant oil-based monomer as the hydrophobic block and easily available and degradable poly (ethylene glycol) (PEG) as the hydrophilic block. These amphiphilic copolymers, including ABA and BAB-type bottlebrush copolymers, and AB and ABA-type linear copolymers are excellent carriers, which all form well-defined spherical nanostructures of similar sizes. Among all nanopesticides with different nanocarriers and azoxystrobin, a bottlebrush copolymer with two hydrophobic domains at both ends and a diblock linear copolymer present a high pesticide-loading capacity. Further study on release and antifungal behaviors shows that the bottlebrush copolymer with two hydrophobic domains is a superior nanocarrier with long sustained release efficacy and exhibits outstanding bioactivity. This work presents a novel and sustainable approach to fabricating highly efficient nanopesticides by elegantly designing molecular structures of biomass-based nanocarriers.

研究领域: 材料科学 · 纳米技术 · 农业科学 · 环境科学 · 聚合物化学
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CHEMISTRY & BIODIVERSITY · 2019 ·Vol. 17 ·期 2 ·e1900570 · IF 1.449

Natural Product-Based Fungicides Discovery: Design, Synthesis and Antifungal Activities of Some Sarisan Analogs Containing 1,3,4-Oxadiazole Moieties

Hongyu Xu,Ao Jia,Enhua Hou,Zhiyan Liu,Rui Yang,Ruige Yang,Yong Guo

A series of sarisan analogs containing 1,3,4-oxadiazole moieties were synthesized by iodine-mediated oxidative cyclization and screened in vitro for their antifungal activities at 50 μg/mL against five phytopathogenic fungi such as Valsa mali , Curvularia lunata , Alternaria alternate , Fusarium solani and Fusarium graminearum . 1,3,4-Oxadiazole derivatives 7e , 7p , 7r , 7t and 7u exhibited potent and a broad spectrum of antifungal activities against at least three phytopathogenic fungi at the concentration of 50 μg/mL. Especially, compound 7r displayed more potent antifungal activities against five phytopathogenic fungi than the positive control hymexazol. The EC 50 of 7r against V. mali , C. lunata and A. alternate were 12.6, 14.5 and 17.0 μg/mL, respectively. Additionally, some interesting results of structure-activity relationships (SARs) were also observed.

CAS / MDL: 533-31-3
研究领域: 药物化学 · 植物病理学 · 有机合成
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ACS Nano · 2024 · IF 15.8

Salinity-Driven Interface Self-Assembly of a Biological Amphiphilic Emulsifier to Form Stable Janus Core–Shell Emulsion for Enhancing Agrichemical Delivery

Yanling Wu,Zhenping Bao,Songhao Zhang,Rui Liu,Yuan Ping,Min Ma,Yuxia Gao,Chengyi He,Tianyue Wu,Yongqiang Ma,Chenhui Zhang,Fengpei Du

Agrichemical losses are a severe threat to the ecological environment. Additionally, some agrichemical compounds contain abundant salt, which increases the instability of formulations, leading to a lower agrichemical utilization and soil hardening. Fortunately, the biological amphiphilic emulsifier sodium deoxycholate alleviates these problems by forming stable Janus core–shell emulsions through salinity-driven interfacial self-assembly. According to the interfacial behavior, dilational rheology, and molecular dynamics simulations, Janus-emulsion molecules are more closely arranged than traditional-emulsion molecules and generate an oil–water interfacial film that transforms into a gel film. In addition, at the same spray volume, the deposition area of the Janus emulsion increased by 37.70% compared with that of the traditional emulsion. Owing to the topology effect and deformation, the Janus emulsion adheres to rice micropapillae, achieving better flush resistance. Meanwhile, based on response of the Janus emulsion to stimulation by carbon dioxide (CO2), the emulsion lost to the soil can form a rigid shell for inhibiting the release of pesticides and metal ions from harming the soil. The pyraclostrobin release rate decreased by 50.89% at 4 h after the Janus emulsion was exposed to CO2. The Chao1 index of the Janus emulsion was increased by 12.49% as compared to coconut oil delivery in soil microbial community. The Janus emulsion ingested by harmful organisms can be effectively absorbed in the intestine to achieve better control effects. This study provides a simple and effective strategy, which turns waste into treasure, by combining metal ions in agrichemicals with natural amphiphilic molecules to prepare stable emulsions for enhancing agrichemical rainfastness and weakening environmental risk.

研究领域: 农业化学 · 环境科学 · 材料科学 · 生物技术
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