Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide DOI
Yihao Li, Tingting Zhang, Haoyun Ma

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(16), P. 6249 - 6267

Published: April 14, 2023

Novel fungicidal agents were designed based on the combination of two privileged scaffolds, thiohydantoin and spirocyclic butenolide, which are widely found in natural products. The synthesized compounds characterized by 1H NMR, 13C high-resolution electrospray ionisation mass spectrometry. vitro antioomycete activity evaluation showed that most exhibited excellent inhibitory activities against different developmental stages life cycle pathogenic oomycete Phytophthora capsici. Compound 5j could inhibit mycelial growth, sporangium production, zoospore release, cystospore germination significantly with EC50 values 0.38, 0.25, 0.11, 0.026 μg/mL, respectively. vivo antifungal/antioomycete bioassay results revealed series generally outstanding control efficacies Pseudoperonospora cubensis, 5j, 5l, 7j, 7k, 7l possessed broad-spectrum antifungal test phytopathogens. protective curative P. capsici representative compound excellent, better than those azoxystrobin. More prominently, promoted biomass accumulation root system reinforced cell wall callose deposition. pronounced upregulation immune response-related genes indicated active inhibitor also functioned as a plant elicitor. Transmission electron microscopy observation enzyme demonstrated mechanism action was to bind pivotal protein, complex III respiratory chain, resulted shortage energy supply. Molecular docking appropriately matched Qo pocket had no interaction commonly mutated site Gly-142, may be significant benefit fungicide resistance management. great advantages potential control, management, induction disease resistance. A further investigation unique structure might have direct implications for creation novel inhibitors plant-pathogenic oomycetes.

Language: Английский

Eu3+-postdoped MOFs are used for fluorescence sensing of TNP, TC and pesticides and for anti-counterfeiting ink application DOI
Lu Liu, Xiaoli Chen, Lu Shang

et al.

Dyes and Pigments, Journal Year: 2022, Volume and Issue: 202, P. 110253 - 110253

Published: March 26, 2022

Language: Английский

Citations

25

Finding Fluorine: Photoproduct Formation during the Photolysis of Fluorinated Pesticides DOI Creative Commons
Akash P. Bhat, William C. K. Pomerantz, William A. Arnold

et al.

Environmental Science & Technology, Journal Year: 2022, Volume and Issue: 56(17), P. 12336 - 12346

Published: Aug. 16, 2022

The photolysis of pesticides with different fluorine motifs was evaluated to quantify the formation fluorinated products in buffered aqueous systems, advanced oxidation (AOP) and reduction processes (ARP), river water. Simulated sunlight quantum yields at pH 7 were 0.0033, 0.0025, 0.0015, 0.00012 for penoxsulam, florasulam, sulfoxaflor, fluroxypyr, respectively. bimolecular rate constants hydroxyl radicals 2 5.7 × 1010 M–1 s–1 and, sulfate radicals, 1.6 2.6 108 sulfoxaflor 100-fold lower. Using quantitative 19F-NMR, complete mass balances obtained. maximum fluoride 53.4 87.4% penoxsulam florasulam under ARP conditions, 6.1 100% fluroxypyr AOP conditions. Heteroaromatic CF3 aliphatic CF2 groups retained multiple photoproducts. Aryl F heteroaromatic readily defluorinated fluoride. formed trifluoroacetate difluoroacetate, increased oxidizing 19F-NMR chemical shifts coupling analysis provided information on hydrogen loss adjacent bonds or changes chirality. Mass spectrometry results consistent observed products. These will assist selecting treatment specific design agrochemicals reduce byproduct formation.

Language: Английский

Citations

25

Aquatic toxicity, ecological effects, human exposure pathways and health risk assessment of liquid crystal monomers DOI
Wei He,

Yuhan Cui,

Hao Yang

et al.

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 461, P. 132681 - 132681

Published: Sept. 30, 2023

Language: Английский

Citations

14

PFAS in Landfill Leachate: Practical Considerations for Treatment and Characterization DOI Creative Commons
Fabrizio Sabba,

Christian Kassar,

Teng Zeng

et al.

Journal of Hazardous Materials, Journal Year: 2024, Volume and Issue: unknown, P. 136685 - 136685

Published: Nov. 1, 2024

Language: Английский

Citations

5

Rational design, synthesis, and antimicrobial evaluation of novel 1,2,4-trizaole-substituted 1,3,4-oxadiazole derivatives with a dual thioether moiety DOI
Qiang Fei, Chunyi Liu,

Yanbi Luo

et al.

Molecular Diversity, Journal Year: 2024, Volume and Issue: 29(1), P. 255 - 267

Published: April 30, 2024

Language: Английский

Citations

4

Fluoride induces immunotoxicity by regulating riboflavin transport and metabolism partly through IL-17A in the spleen DOI

Yurou Qiao,

Yukun Cui,

Yanjia Tan

et al.

Journal of Hazardous Materials, Journal Year: 2024, Volume and Issue: 476, P. 135085 - 135085

Published: July 3, 2024

Language: Английский

Citations

4

Artificial Intelligence-Based Microfluidic Platform for Detecting Contaminants in Water: A Review DOI Creative Commons
Yihao Zhang, Jiaxuan Li, Zhou Yu

et al.

Sensors, Journal Year: 2024, Volume and Issue: 24(13), P. 4350 - 4350

Published: July 4, 2024

Water pollution greatly impacts humans and ecosystems, so a series of policies have been enacted to control it. The first step in performing is detect contaminants the water. Various methods proposed for water quality testing, such as spectroscopy, chromatography, electrochemical techniques. However, traditional testing require utilization laboratory equipment, which large not suitable real-time field. Microfluidic devices can overcome limitations instruments become an efficient convenient tool analysis. At same time, artificial intelligence ideal means recognizing, classifying, predicting data obtained from microfluidic systems. based on machine learning are being developed with great significance next generation monitoring This review begins brief introduction algorithms involved materials used fabrication detection techniques platforms. Then, latest research development combining two pollutant bodies, including heavy metals, pesticides, micro- nanoplastics, microalgae, mainly introduced. Finally, challenges encountered future directions industrial chips discussed.

Language: Английский

Citations

4

A practical fluorometric and colorimetric dual-mode sensing platform based on two-dimensional porous organic nanosheets for rapid determination of trifluralin DOI
Xue Liu, Zhenyu Lu,

Shijun Huang

et al.

Analytical Methods, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Trifluralin, a widely used dinitroaniline herbicide, poses significant toxic risks, necessitating the development of rapid detection methods for food safety. In this study, we prepared ultrathin two-dimensional triphenylamine porous organic nanosheets (TPA-PONs) through facile liquid-phase exfoliation process. The TPA-PONs, characterized by their exceptional fluorescence properties and nanoscale thickness (1.65 ± 0.3 nm), demonstrated remarkable quenching response upon exposure to trifluralin. Spectroscopic analysis combined with DFT calculations revealed that mechanism is driven electron energy transfer. TPA-PONs-based sensor exhibited linear trifluralin concentrations ranging from 0.01 10.0 μmol L-1 limit as low 3.50 nmol L-1. Additionally, was applied detect residues in vegetables, achieving recoveries 89.08-102.84%. To facilitate on-site detection, novel colorimetric film has been developed, enabling visual using smartphone. This dual-mode sensing platform holds potential enhancing safety monitoring.

Language: Английский

Citations

0

The Rise and Risks of Fluorinated Pesticides: A Call for Comprehensive Research to Address Environmental and Health Concerns DOI Creative Commons
Ravikumar Jagani, Haridarshan Patel,

Jasmin Chovatiya

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

InfoMetricsFiguresRef. Journal of Agricultural and Food ChemistryASAPArticle This publication is free to access through this site. Learn More CiteCitationCitation abstractCitation referencesMore citation options ShareShare onFacebookX (Twitter)WeChatLinkedInRedditEmailJump toExpandCollapse ViewpointJanuary 13, 2025The Rise Risks Fluorinated Pesticides: A Call for Comprehensive Research Address Environmental Health ConcernsClick copy article linkArticle link copied!Ravikumar JaganiRavikumar JaganiLautenberg Sciences Laboratory, Department Medicine Climate Science, Icahn School at Mount Sinai, New York, York 10029, United StatesMore by Ravikumar Jaganihttps://orcid.org/0000-0002-7680-860XHiraj PatelHiraj PatelLautenberg Hiraj PatelJasmin ChovatiyaJasmin ChovatiyaLautenberg Jasmin ChovatiyaSyam S. Andra*Syam AndraLautenberg States*[email protected]More Syam Andrahttps://orcid.org/0000-0003-2839-6417Open PDFJournal ChemistryCite this: J. Agric. Chem. 2025, XXXX, XXX, XXX-XXXClick citationCitation copied!https://pubs.acs.org/doi/10.1021/acs.jafc.4c12827https://doi.org/10.1021/acs.jafc.4c12827Published January 2025 Publication History Received 20 December 2024Published online 13 2025article-commentary© American Chemical Society. available under these Terms Use. Request reuse permissionsThis licensed personal use The ACS Publications© SocietyThe Agrochemicals: Double-Edged SwordClick section linkSection copied!The agricultural sector has witnessed a dramatic shift in pest management strategies over the past few decades, with fluorinated pesticides emerging as dominant force. (1−4) From modest 9% market share turn century, compounds now account more than half newly approved pesticides, nearly 70% agrochemicals recent years containing fluorine. (4) surge popularity driven unique properties that fluorination imparts, including enhanced stability, lipophilicity, bioavailability. (5) While characteristics have undoubtedly contributed improved control productivity, they also given rise pressing environmental health concerns demand urgent attention from food chemistry research community. Table 1 lists key aspects findings, sections below outline priorities address issues.Table 1. : Key Aspects Concerns, Listed Alphabetically, Findings Regarding Pesticidesaspect or concerndetailsresearch findingsimplicationsrefaactive ingredient fluorinationhigh level proportion active ingredientsin decade, 61% U.S. conventional pesticide components were organofluorines 30% PFAS, up 23% 14%, respectively, between 2012 2021widespread potential accumulation (1)bioaccumulationaccumulation various organismsfound honeybees (≤140 ng per bee), aquatic organisms, terrestrial wildlifepotential biomagnification chains ecosystem disruption (4)detection challengesneed effective monitoring methodsdevelopment novel fluorescent probe N-(purinyl)-2-chromene-3-carbohydrazide (PCC)improved detection specific (10)endocrine disruptioninterference hormone systemsepoxiconazole inhibits monooxygenases activity steroidogenesis rats human cell linespotential reproductive developmental issues wildlife humans (4)environmental justicedisproportionate exposure certain communitieshigher levels PFAS application near water systems serving Latinx non-Latinx People Color.unequal distribution risks (7)environmental persistencehigh stability carbon–fluorine bonds, long half-lives pesticidesC–F bond energy 485 kJ mol–1; many exceeding 30 days, some 365 days (2416 pydiflumetofen 500 bixafen)long-term contamination bioaccumulation (2), (4)food contaminationresidues found productsepoxiconazole detected 17.6 μg/kg crops; freshwater fish livestockhuman diet (4)formation toxic byproducts metabolitesphotolysis can produce potentially compounds; partial degradation lead formation metaboliteslevels trifluoroacetate difluoroacetate increased oxidizing conditions; multiple photoproducts retained structures similar those parent metabolites may be persistent compoundspotential toxicity products, additional breakdown products wastewater (6), (11)genotoxicityDNA chromosomal damagefipronil, λ-cyhalothrin, cyfluthrin cause genetic damagepotential long-term effects, risk cancer (4)groundwater threatpotential drinking sourcesPFAS-contaminated used within km 732 serviced 18.5 million Californians; 229 978 mg PFOS, PFBS, PFBA applied public supply wells via (2019–2021)ongoing resources risks, widespread (7)immunotoxicityimpacts on immune system functionflupyradifurone impairs pathways bees sublethal concentrations; fipronil shown immunosuppressive effects micepotential susceptibility diseases exposed organisms (4)impact microbial communitiesfluorinated affect populations treatment systemsinhibitory observed involved processespotential reduction efficiency (6)incomplete degradationeven when degrade, often remaincomplete fluorine mass balances demonstrated retention byproducts; maximal defluorination ranged 6.1% 100% depending chemical conditionscontinued presence organic even after (11)increasing prevalencerapid growth approvalsnearly new latter decade fluorinatedpotential (4)industrial trendscontinued importance halogenated agrochemicalsincrease production halogen-substituted agrochemicals: F (40%) > F/Cl (13%) Cl/Br (3%) = F/Br (3%); 77% (2016–2022) are substituted halogenongoing development (3)lack transparencynondisclosure inert ingredientsinert ingredients adjuvants not required labelsdifficulty assessing full profile formulations (12)oxidative stressfluorinated induce reactive oxygen species (ROS) formationenzymes, lipids, protein expression changedcellular damage physiological disruptions (5)persistence wastewaterhigh resistance plantssome remain largely unaffected biological bodies receiving treated effluent (6)plastic interactionadsorption microplasticsepoxiconazole shows high adsorption polyethylene microplasticsenhanced persistence long-range transport (4)recalcitrance biodegradationmicroorganisms struggle break down compoundsfew known enzymes catalyze reactions; biodegradation leaves metabolitesaccumulation environment (9)regulatory comprehensive assessment inadequate compoundsexclusion proposed restrictions REACH, European chemicals regulation; current evaluations fully pesticidespotential gaps regulation underestimation impacts (8), (12)soil contaminationwidespread soil programsbroflanilide epoxiconazole frequently most common pollutants soils because their affinity soillong-term crop uptake (4)structural complexityincreasing stereogenic centers molecules∼48% modern chiral moleculeschallenges varied (2)TFA potentialpesticides substantial source TFA143 C–CF3 groups forming TFA currently EU, USA, China; estimated maximum emissions ≤83 kg/km2 year across Europesignificant contribution (8)types fluorine-containing groupscommon substituents pesticides52% contain trifluoromethyl (F3C) groups, 20% difluoromethyl (F2HC) 4% trifluoromethoxy (F3C–O) groupsdiverse range entering (3)variability degradationdifferent motifs varying photolysis conditionsaryl heteroaromatic easily defluorinated, while CF3 CF2 stablechallenges predicting fate designing processes (11)water contaminationpresence surface groundwatercyfluthrin 1380 ng/L fluometuron 1270 environmentsthreat ecosystems (4)aThis refers primary one provides citations article.The Urgent Need Fate StudiesClick critical issue requires immediate focus. Studies ecosystems, environments wildlife. (4,6−8) Some exhibit soil, indicating contamination. only affects area but leads spread nontarget mechanisms.Research Priority. studies urgently needed. These should include (1) detailed investigations metabolite different compartments (soil, water, air), (2) factors influencing mobility compounds, (3) evaluation impact conditions (pH, temperature, activity) transformation pesticides.Bioaccumulation Chain Impacts: Growing ConcernClick lipophilic nature contributes propensity living organisms. Evidence been ranging animals. raises significant about chains, affecting higher trophic levels, humans. (4)Research In-depth crucial. areas focus mechanisms uptake, accumulation, biotransformation transfer rates magnification accumulate edible crops livestock, implications safety.Ecotoxicological Unraveling Complex InteractionsClick copied!Ecotoxicological unveiled adverse endocrine disruption, toxicity, immunotoxicity. However, our understanding impacts, particularly complex remains limited.Research Expanded ecotoxicological essential, focusing long-term, multigenerational assess chronic species, investigation synergistic interact other contaminants, ecosystem-level understand broader ecological use.Human Implications: Bridging Critical Knowledge GapsClick growing concern demands rigorous investigation. blood samples, raising questions effects. (7) linked issues, kidney cancer, cardiovascular problems, (1)Research needed, epidemiological endocrine, reproductive, systems, biomonitoring extent (occupational, dietary, environmental), transgenerational epigenetic exposure.Metabolite Toxicity: An Overlooked DimensionClick equally compounds. (4,9) aspect overlooked traditional assessments.Research Focused crucial, identification characterization major formed persistence, metabolites, analytical methods detecting quantifying matrices.Alternative Development: Pursuing Safer SolutionsClick copied!As grow, there an increasing need explore alternative develop less agrochemicals. presents opportunity innovation field chemistry.Research Development safer alternatives focus, design synthesis nonfluorinated match efficacy minimizing exploration biopesticides synthetic delivery could reduce pesticides.Analytical Challenges: Improving Detection MonitoringClick complexity diversity pose challenges. (10,11) Improved matrices essential assessment.Research Advancement techniques sensitive, high-throughput simultaneous standardization protocols ensure comparability data regions, techniques, such nontargeted analysis, identify unknown matrices.Regulatory Science: Informing Policy Robust DataClick copied!Current regulatory frameworks approval challenges posed There approaches consider cumulative degradates ingredients.Research support evidence-based decisions models inform mixture assessments, thresholds adequacy protecting health.Conclusion: Interdisciplinary ResearchClick time action now. We must prioritize bridges knowledge gaps, develops alternatives, scientific basis sound decisions. Only efforts we hope balance benefits imperative health.Author InformationClick copied!Corresponding AuthorSyam Andra - Lautenberg States; https://orcid.org/0000-0003-2839-6417; Email: [email protected]AuthorsRavikumar Jagani https://orcid.org/0000-0002-7680-860XHiraj Patel StatesJasmin Chovatiya StatesFundingThis work was partially funded National Institute Institutes Health, Grant P30 ES023515 Robert O. Wright [Mount Sinai Center Environment Across LifeSpan (HEALS)], U2CES026561 (Mount HHEAR Targeted Analysis Laboratory), U2CES030859 Manish Arora Untargeted Laboratory).NotesThe authors declare no competing financial interest.ReferencesClick copied! references 12 publications. 1Donley, N.; Cox, C.; Bennett, K.; Temkin, A. M.; Andrews, D. Q.; Naidenko, V. Forever Source Contamination Environment. Environ. Perspect. 2024, 132 (7), 75003, DOI: 10.1289/EHP13954 Google ScholarThere corresponding record reference.2Jeschke, P. Recent developments pesticides. Pest Manage. Sci. 80 3065– 3087, 10.1002/ps.7921 reference.3Jeschke, Active Ingredients Sustainable Modern Crop Protection Agriculture. ChemSusChem e202401042 10.1002/cssc.202401042 reference.4Alexandrino, Almeida, C. M. R.; Mucha, P.; Carvalho, F. Revisiting pollution: case Pollut. 2022, 292, 118315, 10.1016/j.envpol.2021.118315 Scholar4Revisiting pesticidesAlexandrino, Diogo Marisa Ana Maria F.Environmental Pollution (Oxford, Kingdom) (2022), 292 (Part_A), 118315CODEN: ENPOEK; ISSN:0269-7491. (Elsevier Ltd.) review. acquired agrochem. due fluoroorg. last two decades. trend accompanied framework entailing all neg. environment, esp. considering hazardous result incorporation into org. mols. review aims safe/hazardous dichotomy assocd. providing updated outlook relevancy how it role pollutants. Specifically, discussed, analyzing act substances non-target >> SciFinder ®https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BB3MXit1ektL%252FJ&md5=7ced1326803e2dacae7dcc28170a7ab15Mesquita, F.; Gonçalves, Lethal Sub-Lethal Effects Copper-Based Pesticides-A Review. Int. Res. Public 2023, (4), 3706, 10.3390/ijerph20043706 reference.6Omotola, Adekilekun, K. T.; Solomon, O.; Muizzat, I.; Oluranti, B. Compounds Wastewater Treatment Plants. In Fluoride Fluorocarbon Sources, Issues, Remediation; Kumar, N., Ed.; Springer Nature: Singapore, 2024; pp 367– 387.Google reference.7Libenson, A.; Karasaki, S.; Cushing, L. J.; Tran, Rempel, L.; Morello-Frosch, Pace, E. PFAS-Contaminated Pesticides Applied Supply Wells Disproportionately Impact Communities Color California. ES&T Water 4 2495– 2503, 10.1021/acsestwater.3c00845 reference.8Joerss, H.; Freeling, van Leeuwen, Hollender, Liu, X.; Nödler, Wang, Z.; Yu, B.; Zahn, D.; Sigmund, G. (TFA) resources. 193, 109061, 10.1016/j.envint.2024.109061 reference.9Alexandrino, Atlas Reviews Biotechnology 42 991– 1009, 10.1080/07388551.2021.1977234 reference.10Liu, Y.; Sun, Jia, Yue, Yang, Fu, Ye, Novel (2,6-difluorobenzoyl)urea-activated fluorine-containing-pesticide detection. Engineering (3), 112786, 10.1016/j.jece.2024.112786 reference.11Bhat, Pomerantz, W. Arnold, Finding Fluorine: Photoproduct Formation during Photolysis Pesticides. Technol. 56 (17), 12336– 12346, 10.1021/acs.est.2c04242 Scholar11Finding fluorine: photoproduct pesticidesBhat, Akash William A.Environmental Science & Technology 12336-12346CODEN: ESTHAG; ISSN:1520-5851. (American Society) evaluated quantify buffered aq. advanced oxidn. (AOP) redn. (ARP), river water. Simulated sunlight quantum yields pH 7 0.0033, 0.0025, 0.0015, 0.00012 penoxsulam, florasulam, sulfoxaflor, fluroxypyr, resp. bimol. rate consts. hydroxyl radicals 2 5.7 x 1010 M-1 s-1 and, sulfate radicals, 1.6 2.6 108 sulfoxaflor 100-fold lower. Using quant. 19F-NMR, complete obtained. max. fluoride 53.4 87.4% penoxsulam florasulam ARP conditions, 6.1 fluroxypyr AOP conditions. Heteroarom. aliph. photoproducts. Aryl heteroarom. readily defluorinated fluoride. difluoroacetate, 19F-NMR chem. shifts coupling anal. provided information hydrogen loss adjacent bonds changes chirality. Mass spectrometry results consistent obsd. products. will assist selecting agrochems. byproduct formation. ®https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BB38XitFaiu7nJ&md5=697e37bc463631bc935bdcf06cb0b25812Sehgal, Barr, Eick, Invited Perspective: Far Reach PFAS-Inert Adjuvants Pesticide Formulations. 71304, 10.1289/EHP15445 reference.Cited By Click copied!This yet cited publications.Download PDFFiguresReferences Get e-AlertsGet e-AlertsJournal copied!https://doi.org/10.1021/acs.jafc.4c12827Published 2025© permissionsArticle Views-Altmetric-Citations-Learn metrics closeArticle Views COUNTER-compliant sum text downloads since November 2008 (both PDF HTML) institutions individuals. regularly reflect usage leading days.Citations number articles citing article, calculated Crossref daily. Find counts.The Altmetric Attention Score quantitative measure received online. Clicking donut icon load page altmetric.com details score social media article. calculated.Recommended Articles FiguresReferencesAbstractHigh Resolution ImageDownload MS PowerPoint SlideReferences 4Revisiting 387.There 11Finding reference.

Language: Английский

Citations

0

Nontarget Analysis and Characterization of a Group of Abundant Polyfluoroalkyl Substances─Fluorinated Benzoylurea Pesticides and Their Analogues and Transformation Products in Fish by LC-HRMS and Chemical Species-Specific Algorithms DOI
Caiming Tang,

Yizhe Zhu,

Yiyang Liang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

Poly- and perfluoroalkyl substances (PFASs) are a large class of fluorinated chemicals used in various industrial agrochemical products such as benzoylurea (FBU) pesticides. Initiated from an incidental preliminary finding three high-abundance FBUs fish, this study implemented nontarget analysis characterization for together with their analogues transformation (TPs) fish using liquid chromatography, high-resolution mass spectrometry, chemical species-specific algorithms. A total 23 FBU-relevant compounds were found tentatively/accurately elucidated structures, including 18 PFASs 5 non-PFAS compounds, which 4 original FBUs, 8 FBU analogues, 11 FBU-TPs. The concentrations 0.8–1919.3 ng/g the samples. strategy data-processing algorithms can be extended to other fluorine-containing pesticides, results provide new understanding PFAS pollution unveil important source pollutants, utilization FBUs.

Language: Английский

Citations

0