ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img
RETURN TO ISSUEPREVAgricultural and Env...Agricultural and Environmental ChemistryNEXT

Enantioselective Bioactivity, Toxicity, and Degradation in Vegetables and Soil of Chiral Fungicide Mandipropamid

  • Jing Zhang
    Jing Zhang
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    More by Jing Zhang
  • Qiqi Wu
    Qiqi Wu
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    More by Qiqi Wu
  • Yanru Zhong
    Yanru Zhong
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    More by Yanru Zhong
  • Zhen Wang
    Zhen Wang
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    More by Zhen Wang
  • Zongzhe He
    Zongzhe He
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    More by Zongzhe He
  • Yanqing Zhang
    Yanqing Zhang
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
  • , and 
  • Minghua Wang*
    Minghua Wang
    Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing 210095, China
    *Email: [email protected]. Tel/Fax: +86 25 84395479.
    More by Minghua Wang
Cite this: J. Agric. Food Chem. 2021, 69, 45, 13416–13424
Publication Date (Web):November 5, 2021
https://doi.org/10.1021/acs.jafc.1c04370
Copyright © 2021 American Chemical Society

    Article Views

    893

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Mandipropamid (MDP) is a widely used chiral fungicide to control oomycete pathogens with two enantiomers. In this study, the enantioselective bioactivity, toxicity, and degradation of MDP were investigated for the first time. The bioactivity of S-MDP was 118592 times higher than that of R-MDP and 1.141.67 times higher than that of Rac-MDP against six phytopathogens. Molecular docking found that S-MDP formed a strong halogen bond with HIS 693 of cellulose synthase and possessed a lower binding energy, which validated the results of the bioactivity assay. S-MDP showed lower toxicity toward Spirodela polyrhiza, while it exhibited higher toxicity in Danio rerio embryo and larva. S-MDP preferentially degraded in cowpea and pepper, while R-MDP preferentially degraded in soil. There is no significant difference between the two enantiomers in the toxicity of adult D. rerio and in cucumber degradation. Therefore, the development of the S-enantiomer was considered as a better option to exhibit high efficiency, which could reduce the residual risk of the pesticide and ensure environmental safety.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jafc.1c04370.

    • Linear regression parameters and LOQ for the MDP enantiomers in different matrices (Table S1); accuracy and precision of the method in the four matrices (Table S2); and chemical structures and typical chromatograms of MDP enantiomers (Figure S1) (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 11 publications.

    1. Jiajin Song, Conglai Zheng, Mengting Qiu, Xiu-ping Zhan, Zihan Zhang, Houpu Zhang, Nan Shi, Luqing Zhang, Yunlong Yu, Mogens Nicolaisen, Lihui Xu, Hua Fang. Mechanisms Underlying the Overlooked Chiral Fungicide-Driven Enantioselective Proliferation of Antibiotic Resistance in Earthworm Intestinal Microbiome. Environmental Science & Technology 2024, 58 (6) , 2931-2943. https://doi.org/10.1021/acs.est.3c07761
    2. Siman Ma, Hao Xin, Pengfei Zhao, Shiwen Feng, Jialin Chen, Shiliang Yin, Yanan Wei, Yitong Shi, Ge Jin, Xin Di, Hong Zhang. Comprehensive Stereoselectivity Assessment of Toxicokinetics, Tissue Distribution, Cytotoxicity, and Environmental Fate of Chiral Pesticide Propiconazole. Journal of Agricultural and Food Chemistry 2023, 71 (49) , 19760-19771. https://doi.org/10.1021/acs.jafc.3c05340
    3. Zhou Tong, Xu Dong, DanDan Meng, XiaoTong Yi, MingNa Sun, Yue Chu, JinSheng Duan. Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems. Journal of Agricultural and Food Chemistry 2023, 71 (3) , 1426-1433. https://doi.org/10.1021/acs.jafc.2c07924
    4. Siman Ma, Hong Zhang, Fei Li, Pengfei Zhao, Shiliang Yin, Jiaqi Sun, Jiayu Xu, Zhenqi Wang, Xin Xu, Xin Di. Systemic Stereoselectivity Study of Fenobucarb: Environmental Behaviors in Greenhouse Vegetables, Fruits, Earthworms, and Soils and Its Cytotoxicity. Journal of Agricultural and Food Chemistry 2022, 70 (7) , 2127-2135. https://doi.org/10.1021/acs.jafc.1c06420
    5. Hui Liu, Mengqi Liu, Kuiyuan Chen, Mei Shan, Yongye Li. Fertilization can modify the enantioselective persistence of penthiopyrad in relation to the co-influence on soil ecological health. Environmental Research 2023, 224 , 115514. https://doi.org/10.1016/j.envres.2023.115514
    6. Xiaokang An, Xinglu Pan, Runan Li, Fengshou Dong, Wentao Zhu, Jun Xu, Xiaohu Wu, Yongquan Zheng. Comprehensive evaluation of novel fungicide benzovindiflupyr at the enantiomeric level: Bioactivity, toxicity, mechanism, and dissipation behavior. Science of The Total Environment 2023, 860 , 160535. https://doi.org/10.1016/j.scitotenv.2022.160535
    7. Shiyin Mu, Li Dou, Yu Ye, Du Chi, Kankan Zhang. Effects of Household Processing on Residues of the Chiral Fungicide Mandipropamid in Four Common Vegetables. International Journal of Environmental Research and Public Health 2022, 19 (23) , 15543. https://doi.org/10.3390/ijerph192315543
    8. Zhiyuan Meng, Jiajia Cui, Ruisheng Li, Wei Sun, Xin Bao, Jianjun Wang, Zhiqiang Zhou, Wentao Zhu, Xiaojun Chen. Systematic evaluation of chiral pesticides at the enantiomeric level: A new strategy for the development of highly effective and less harmful pesticides. Science of The Total Environment 2022, 846 , 157294. https://doi.org/10.1016/j.scitotenv.2022.157294
    9. Lingxi Han, Yalei Liu, Jiyun Nie, Xiangwei You, Yiqiang Li, Xiuguo Wang, Jun Wang. Indigenous functional microbial degradation of the chiral fungicide mandipropamid in repeatedly treated soils: Preferential changes in the R-enantiomer. Journal of Hazardous Materials 2022, 435 , 128961. https://doi.org/10.1016/j.jhazmat.2022.128961
    10. Shanshan Di, Tao Cang, Zhenzhen Liu, Yunye Xie, Huiyu Zhao, Peipei Qi, Zhiwei Wang, Hao Xu, Xinquan Wang. Comprehensive evaluation of chiral pydiflumetofen from the perspective of reducing environmental risks. Science of The Total Environment 2022, 826 , 154033. https://doi.org/10.1016/j.scitotenv.2022.154033
    11. Jianmin Li, Tingting Lan, Guangqian Yang, Shiyin Mu, Kankan Zhang. Enantioselective evaluation of the chiral fungicide mandipropamid: Dissipation, distribution and potential dietary intake risk in tomato, cucumber, Chinese cabbage and cowpea. Ecotoxicology and Environmental Safety 2022, 232 , 113260. https://doi.org/10.1016/j.ecoenv.2022.113260

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect