Imazethapyr (BioDeep_00000002808)

 

Secondary id: BioDeep_00000784069

human metabolite blood metabolite


代谢物信息卡片


5-ethyl-2-[5-methyl-4-oxo-5-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid

化学式: C15H19N3O3 (289.1426344)
中文名称: 咪草烟
谱图信息: 最多检出来源 Homo sapiens(blood) 1.65%

分子结构信息

SMILES: CCC1=CC(=C(N=C1)C2=NC(C(=O)N2)(C)C(C)C)C(=O)O
InChI: InChI=1S/C15H19N3O3/c1-5-9-6-10(13(19)20)11(16-7-9)12-17-14(21)15(4,18-12)8(2)3/h6-8H,5H2,1-4H3,(H,19,20)(H,17,18,21)

描述信息

Imazethapyr is a widely used imidazolinone herbicide worldwide, and its potential adverse effects on non-target plants have raised concerns. Understanding the mechanisms of imazethapyr phytotoxicity is crucial for its agro-ecological risk assessment.

同义名列表

6 个代谢物同义名

5-ethyl-2-[5-methyl-4-oxo-5-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid; 5-Ethyl-2-[5-methyl-4-oxo-5-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylate; 5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-3H-imidazol-2-yl)pyridine-3-carboxylic acid; Imazethapyr, amonium salt; Imazethapyr-ammonium; IMAZETHAPYR



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Mamta Kaswa, Anup Kumar, Mahendra Prasad, Deepak Upadhyay, Sonu Kumar Mahawer, Vinod Kumar Washnik, Pooja Tamboli. Exploring the influence of invasive weed biochar on the sorption and dissipation dynamics of imazethapyr in sandy loam soil. Environmental monitoring and assessment. 2024 Apr; 196(5):478. doi: 10.1007/s10661-024-12653-8. [PMID: 38664274]
  • Lijuan Liu, Ziyu Chen, Nan Zhang, Jiahui Liu, Zhongling Tian, Chengliang Sun. Transcriptomic and metabolomic analysis provides insight into imazethapyr toxicity to non-target plants. Environmental science and pollution research international. 2024 Apr; 31(19):28368-28378. doi: 10.1007/s11356-024-32967-x. [PMID: 38532215]
  • Qiushui Zhang, Jun Li, Hui Chen, Xuan Xuan, Dongmei Xu, Yuezhong Wen. Mechanisms Underlying Allelopathic Disturbance of Herbicide Imazethapyr on Wheat and Its Neighboring Ryegrass (Lolium perenne). Journal of agricultural and food chemistry. 2024 Feb; 72(7):3445-3455. doi: 10.1021/acs.jafc.3c09519. [PMID: 38325393]
  • Yanan Tang, Qianhang Zhai, Zhengyi Zhang, Zhou Lu, Ranhong Li, Hao Zhang. Exploration of the biodegradation pathway and enhanced removal of imazethapyr from soil by immobilized Bacillus marcorestinctum YN1. Chemosphere. 2024 Jan; 351(?):141178. doi: 10.1016/j.chemosphere.2024.141178. [PMID: 38218236]
  • Rajeev Kumar, V Visha Kumari, Ranjit Singh Gujjar, Mala Kumari, Sanjay Kumar Goswami, Jhuma Datta, Srikumar Pal, Sudhir Kumar Jha, Ashok Kumar, Ashwini Dutt Pathak, Milan Skalicky, Manzer H Siddiqui, Akbar Hossain. Evaluating the imazethapyr herbicide mediated regulation of phenol and glutathione metabolism and antioxidant activity in lentil seedlings. PeerJ. 2024; 12(?):e16370. doi: 10.7717/peerj.16370. [PMID: 38188166]
  • Jinye Huang, Jun Li, Hui Chen, Chensi Shen, Yuezhong Wen. Phytotoxicity alleviation of imazethapyr to non-target plant wheat: active regulation between auxin and DIMBOA. Environmental science and pollution research international. 2023 Oct; ?(?):. doi: 10.1007/s11356-023-30608-3. [PMID: 37897577]
  • Lei Cheng, Lixia Wang, Xinhong Wang, Yang Ou, Huiping Liu, Xia Hou, Liming Yan, Xinyi Li. The various effect of cow manure compost on the degradation of imazethapyr in different soil types. Chemosphere. 2023 Oct; 337(?):139325. doi: 10.1016/j.chemosphere.2023.139325. [PMID: 37356585]
  • Yihao Li, Nan Zhang, Jiarui Xu, Lijuan Liu, Xiaochuang Cao, Xianyong Lin, Chengliang Sun. Imazethapyr disrupts plant phosphorus homeostasis and acquisition strategies. Journal of hazardous materials. 2023 Aug; 460(?):132317. doi: 10.1016/j.jhazmat.2023.132317. [PMID: 37619275]
  • Ademir Sergio Ferreira Araujo, Mariane Pertile, Romário Martins Costa, Mayanna Karlla Lima Costa, Rhaiana Oliveira de Aviz, Lucas William Mendes, Erika Valente de Medeiros, Diogo Paes da Costa, Vania Maria Maciel Melo, Arthur Prudencio de Araujo Pereira. Short-term responses of plant growth-promoting bacterial community to the herbicides imazethapyr and flumioxazin. Chemosphere. 2023 Apr; 328(?):138581. doi: 10.1016/j.chemosphere.2023.138581. [PMID: 37019406]
  • Jinye Huang, Manxin Bao, Jun Li, Hui Chen, Dongmei Xu, Zunwei Chen, Yuezhong Wen. Enantioselective Response of Wheat Seedlings to Imazethapyr: From the Perspective of Fe and the Secondary Metabolite DIMBOA. Journal of agricultural and food chemistry. 2022 May; 70(18):5516-5525. doi: 10.1021/acs.jafc.1c07727. [PMID: 35476430]
  • Shivani, Satvir Kaur Grewal, Ranjit Kaur Gill, Harpreet Kaur Virk, Rachana D Bhardwaj. Methylglyoxal detoxification pathway - Explored first time for imazethapyr tolerance in lentil (Lens culinaris L.). Plant physiology and biochemistry : PPB. 2022 Apr; 177(?):10-22. doi: 10.1016/j.plaphy.2022.02.007. [PMID: 35219898]
  • Lynn Abou-Khater, Fouad Maalouf, Abdulqader Jighly, Alsamman M Alsamman, Diego Rubiales, Nicolas Rispail, Jinguo Hu, Yu Ma, Rind Balech, Aladdin Hamwieh, Michael Baum, Shiv Kumar. Genomic regions associated with herbicide tolerance in a worldwide faba bean (Vicia faba L.) collection. Scientific reports. 2022 01; 12(1):158. doi: 10.1038/s41598-021-03861-0. [PMID: 34996977]
  • Qing Chang, Weiping Ji, Qingxiang Lu, Jiaying Xue, Rimao Hua, Xiangwei Wu. Bioavailability and toxicity of imazethapyr in maize plant estimated by four chemical extraction techniques in different soils. The Science of the total environment. 2021 Dec; 801(?):149594. doi: 10.1016/j.scitotenv.2021.149594. [PMID: 34418631]
  • Jie Wang, Shiming Li, Lei Lan, Mushan Xie, Shu Cheng, Xiaolong Gan, Gang Huang, Guohua Du, Kang Yu, Xuemei Ni, Baolong Liu, Guoxiong Peng. De novo genome assembly of a foxtail millet cultivar Huagu11 uncovered the genetic difference to the cultivar Yugu1, and the genetic mechanism of imazethapyr tolerance. BMC plant biology. 2021 Jun; 21(1):271. doi: 10.1186/s12870-021-03003-8. [PMID: 34118890]
  • Catarine Markus, Ales Pecinka, Aldo Merotto. Insights into the Role of Transcriptional Gene Silencing in Response to Herbicide-Treatments in Arabidopsis thaliana. International journal of molecular sciences. 2021 Mar; 22(7):. doi: 10.3390/ijms22073314. [PMID: 33804990]
  • Paawan Kaur, Pervinder Kaur, Navjyot Kaur, Deepali Jain, Kuldip Singh, Makhan Singh Bhullar. Dissipation and phytotoxicity of imazethapyr and imazamox in soils amended with β-cyclodextrin-chitosan biocomposite. The Science of the total environment. 2020 Sep; 735(?):139566. doi: 10.1016/j.scitotenv.2020.139566. [PMID: 32485456]
  • Qianqiu Zhao, Wanyue Liu, Yan Li, Mingjing Ke, Qian Qu, Wenting Yuan, Xiangliang Pan, Haifeng Qian. Enantioselective effects of imazethapyr residues on Arabidopsis thaliana metabolic profile and phyllosphere microbial communities. Journal of environmental sciences (China). 2020 Jul; 93(?):57-65. doi: 10.1016/j.jes.2020.03.009. [PMID: 32446460]
  • Wanyue Liu, Qianqiu Zhao, Zhenyan Zhang, Yan Li, Nuohan Xu, Qian Qu, Tao Lu, Xiangliang Pan, Haifeng Qian. Enantioselective effects of imazethapyr on Arabidopsis thaliana root exudates and rhizosphere microbes. The Science of the total environment. 2020 May; 716(?):137121. doi: 10.1016/j.scitotenv.2020.137121. [PMID: 32059308]
  • Wanyue Liu, Mingjing Ke, Zhenyan Zhang, Tao Lu, Youchao Zhu, Yan Li, Xiangliang Pan, Haifeng Qian. Effects of imazethapyr spraying on plant growth and leaf surface microbial communities in Arabidopsis thaliana. Journal of environmental sciences (China). 2019 Nov; 85(?):35-45. doi: 10.1016/j.jes.2019.04.020. [PMID: 31471029]
  • Jian Li, Xingxiang Gao, Mei Li, Feng Fang. Resistance evolution and mechanisms to ALS-inhibiting herbicides in Capsella bursa-pastoris populations from China. Pesticide biochemistry and physiology. 2019 Sep; 159(?):17-21. doi: 10.1016/j.pestbp.2019.05.010. [PMID: 31400779]
  • Qian Wang, Lu'an Ge, Ning Zhao, Lele Zhang, Ludan You, Dandan Wang, Weitang Liu, Jinxin Wang. A Trp-574-Leu mutation in the acetolactate synthase (ALS) gene of Lithospermum arvense L. confers broad-spectrum resistance to ALS inhibitors. Pesticide biochemistry and physiology. 2019 Jul; 158(?):12-17. doi: 10.1016/j.pestbp.2019.04.001. [PMID: 31378346]
  • Zhaofeng Huang, Biaofeng Sui, Chaoxian Zhang, Hongjuan Huang, Shouhui Wei. The basis of resistance mechanism to mesosulfuron-methyl in Tausch's goatgrass (Aegilops tauschii Coss.). Pesticide biochemistry and physiology. 2019 Mar; 155(?):126-131. doi: 10.1016/j.pestbp.2019.01.015. [PMID: 30857622]
  • Maria Inês da Costa Marinho, Anna Isabel Guido Costa, Nívea Moreira Vieira, Maria Carolina Gomes Paiva, Francisco Cláudio Lopes de Freitas, Antonio Alberto da Silva. Validation and application of a QuEChERS based method for estimation of half-life of imidazolinone herbicides in soils by LC-ESI-MS/MS. Ecotoxicology and environmental safety. 2019 Jan; 167(?):212-217. doi: 10.1016/j.ecoenv.2018.09.075. [PMID: 30340086]
  • Scott C Anderson, Linh Chu, Chandra Bouma, Logan Beukelman, Rayna McLouth, Evan Larson, Amanda M Nienow. Comparison of the Photodegradation of Imazethapyr in Aqueous Solution, on Epicuticular Waxes, and on Intact Corn (Zea Mays) and Soybean (Glycine Max) Leaves. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2019; 54(2):129-137. doi: 10.1080/03601234.2018.1511400. [PMID: 30285550]
  • Kailin Liu, Ying He, Shiji Xu, Lifeng Hu, Kun Luo, Xiangying Liu, Min Liu, Xiaomao Zhou, Lianyang Bai. Mechanism of the effect of pH and biochar on the phytotoxicity of the weak acid herbicides imazethapyr and 2,4-D in soil to rice (Oryza sativa) and estimation by chemical methods. Ecotoxicology and environmental safety. 2018 10; 161(?):602-609. doi: 10.1016/j.ecoenv.2018.05.096. [PMID: 29929137]
  • Roman B Vercellino, Claudio E Pandolfo, Gabriela Breccia, Miguel Cantamutto, Alejandro Presotto. AHAS Trp574Leu substitution in Raphanus sativus L.: screening, enzyme activity and fitness cost. Pest management science. 2018 Jul; 74(7):1600-1607. doi: 10.1002/ps.4849. [PMID: 29314549]
  • Jian Li, Mei Li, Xingxiang Gao, Feng Fang. A novel amino acid substitution Trp574Arg in acetolactate synthase (ALS) confers broad resistance to ALS-inhibiting herbicides in crabgrass (Digitaria sanguinalis). Pest management science. 2017 Dec; 73(12):2538-2543. doi: 10.1002/ps.4651. [PMID: 28643897]
  • Alvaro S Larran, Valeria E Palmieri, Valeria E Perotti, Lucas Lieber, Daniel Tuesca, Hugo R Permingeat. Target-site resistance to acetolactate synthase (ALS)-inhibiting herbicides in Amaranthus palmeri from Argentina. Pest management science. 2017 Dec; 73(12):2578-2584. doi: 10.1002/ps.4662. [PMID: 28703943]
  • Vikas Kumar, Anupama Singh, T K Das, Dhruba Jyoti Sarkar, Shashi Bala Singh, Rashmi Dhaka, Anil Kumar. Release behavior and bioefficacy of imazethapyr formulations based on biopolymeric hydrogels. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2017 Jun; 52(6):402-409. doi: 10.1080/03601234.2017.1293446. [PMID: 28272993]
  • Scott C Anderson, Amy Christiansen, Alexa Peterson, Logan Beukelman, Amanda M Nienow. Statistical analysis of the photodegradation of imazethapyr on the surface of extracted soybean (Glycine max) and corn (Zea mays) epicuticular waxes. Environmental science. Processes & impacts. 2016 Oct; 18(10):1305-1315. doi: 10.1039/c6em00401f. [PMID: 27711795]
  • Chongchong Sun, Si Chen, Yujian Jin, Hao Song, Songlin Ruan, Zhengwei Fu, Muhammad Asad Ullah Asad, Haifeng Qian. Effects of the Herbicide Imazethapyr on Photosynthesis in PGR5- and NDH-Deficient Arabidopsis thaliana at the Biochemical, Transcriptomic, and Proteomic Levels. Journal of agricultural and food chemistry. 2016 Jun; 64(22):4497-504. doi: 10.1021/acs.jafc.6b01699. [PMID: 27215288]
  • Zhaofeng Huang, Jinyi Chen, Chaoxian Zhang, Hongjuan Huang, Shouhui Wei, Xinxin Zhou, Jingchao Chen, Xu Wang. Target-site basis for resistance to imazethapyr in redroot amaranth (Amaranthus retroflexus L.). Pesticide biochemistry and physiology. 2016 Mar; 128(?):10-5. doi: 10.1016/j.pestbp.2015.10.011. [PMID: 26969434]
  • Yuezhong Wen, Lijuan Zhang, Zunwei Chen, Xiaolin Sheng, Jiguo Qiu, Dongmei Xu. Co-exposure of silver nanoparticles and chiral herbicide imazethapyr to Arabidopsis thaliana: Enantioselective effects. Chemosphere. 2016 Feb; 145(?):207-14. doi: 10.1016/j.chemosphere.2015.11.035. [PMID: 26688257]
  • Jill F Lebov, Lawrence S Engel, David Richardson, Susan L Hogan, Jane A Hoppin, Dale P Sandler. Pesticide use and risk of end-stage renal disease among licensed pesticide applicators in the Agricultural Health Study. Occupational and environmental medicine. 2016 Jan; 73(1):3-12. doi: 10.1136/oemed-2014-102615. [PMID: 26177651]
  • Zunwei Chen, Hui Chen, Yuqin Zou, Jiguo Qiu, Yuezhong Wen, Dongmei Xu. Are Nutrient Stresses Associated with Enantioselectivity of the Chiral Herbicide Imazethapyr in Arabidopsis thaliana?. Journal of agricultural and food chemistry. 2015 Dec; 63(47):10209-17. doi: 10.1021/acs.jafc.5b04495. [PMID: 26566036]
  • Anahí Magdaleno, Marina Peralta Gavensky, Anabella V Fassiano, María C Ríos de Molina, Marina Santos, Hugo March, Juan Moretton, Ángela B Juárez. Phytotoxicity and genotoxicity assessment of imazethapyr herbicide using a battery of bioassays. Environmental science and pollution research international. 2015 Dec; 22(23):19194-202. doi: 10.1007/s11356-015-5103-5. [PMID: 26250814]
  • Jinyi Chen, Zhaofeng Huang, Chaoxian Zhang, Hongjuan Huang, Shouhui Wei, Jingchao Chen, Xu Wang. Molecular basis of resistance to imazethapyr in redroot pigweed (Amaranthus retroflexus L.) populations from China. Pesticide biochemistry and physiology. 2015 Oct; 124(?):43-7. doi: 10.1016/j.pestbp.2015.04.002. [PMID: 26453229]
  • Haifeng Qian, Haiping Lu, Haiyan Ding, Michel Lavoie, Yali Li, Weiping Liu, Zhengwei Fu. Analyzing Arabidopsis thaliana root proteome provides insights into the molecular bases of enantioselective imazethapyr toxicity. Scientific reports. 2015 Jul; 5(?):11975. doi: 10.1038/srep11975. [PMID: 26153126]
  • Raphael C Cusati, Luiz C A Barbosa, Célia R A Maltha, Antônio J Demuner, Alberto Oliveros-Bastidas, Antônio A Silva. Tetraoxanes as a new class of efficient herbicides comparable with commercial products. Pest management science. 2015 Jul; 71(7):1037-48. doi: 10.1002/ps.3891. [PMID: 25157959]
  • Geovane B Reimche, Sérgio L O Machado, Maria Angélica Oliveira, Renato Zanella, Valderi Luiz Dressler, Erico M M Flores, Fábio F Gonçalves, Filipe F Donato, Matheus A G Nunes. Imazethapyr and imazapic, bispyribac-sodium and penoxsulam: zooplankton and dissipation in subtropical rice paddy water. The Science of the total environment. 2015 May; 514(?):68-76. doi: 10.1016/j.scitotenv.2015.01.055. [PMID: 25659307]
  • Recep Liman, İbrahim Hakkı Ciğerci, Nur Serap Öztürk. Determination of genotoxic effects of Imazethapyr herbicide in Allium cepa root cells by mitotic activity, chromosome aberration, and comet assay. Pesticide biochemistry and physiology. 2015 Feb; 118(?):38-42. doi: 10.1016/j.pestbp.2014.11.007. [PMID: 25752428]
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  • Haifeng Qian, Yali Li, Chongchong Sun, Michel Lavoie, Jun Xie, Xiaocui Bai, Zhengwei Fu. Trace concentrations of imazethapyr (IM) affect floral organs development and reproduction in Arabidopsis thaliana: IM-induced inhibition of key genes regulating anther and pollen biosynthesis. Ecotoxicology (London, England). 2015 Jan; 24(1):163-71. doi: 10.1007/s10646-014-1369-5. [PMID: 25348600]
  • Haifeng Qian, Xiao Han, Xiaofeng Peng, Tao Lu, Weiping Liu, Zhengwei Fu. The circadian clock gene regulatory module enantioselectively mediates imazethapyr-induced early flowering in Arabidopsis thaliana. Journal of plant physiology. 2014 Mar; 171(5):92-8. doi: 10.1016/j.jplph.2013.11.011. [PMID: 24484962]
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