Metolachlor (BioDeep_00000001166)

 

Secondary id: BioDeep_00001871666

human metabolite blood metabolite


代谢物信息卡片


2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide

化学式: C15H22ClNO2 (283.1338982)
中文名称: 异丙甲草胺
谱图信息: 最多检出来源 Homo sapiens(blood) 8.11%

分子结构信息

SMILES: CCC1=C(N(C(C)COC)C(=O)CCl)C(C)=CC=C1
InChI: InChI=1S/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3

描述信息

CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9405; ORIGINAL_PRECURSOR_SCAN_NO 9403
CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9416; ORIGINAL_PRECURSOR_SCAN_NO 9412
CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9435; ORIGINAL_PRECURSOR_SCAN_NO 9432
CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9411; ORIGINAL_PRECURSOR_SCAN_NO 9409
CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9432; ORIGINAL_PRECURSOR_SCAN_NO 9430
CONFIDENCE standard compound; INTERNAL_ID 988; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9555; ORIGINAL_PRECURSOR_SCAN_NO 9554
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 1082
CONFIDENCE standard compound; EAWAG_UCHEM_ID 268
CONFIDENCE standard compound; INTERNAL_ID 4040
CONFIDENCE standard compound; INTERNAL_ID 8418
CONFIDENCE standard compound; INTERNAL_ID 3556
D010575 - Pesticides > D006540 - Herbicides
D016573 - Agrochemicals

同义名列表

6 个代谢物同义名

2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide; 2-chloro-N-(2-Ethyl-6-methylphenyl)-N-(2-methoxyethyl)acetamide; metolachlor [ANSI, WSSA]; metolachloor; metolachlor; pennant



数据库引用编号

50 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

  • Yannan Shi, Jinping Wang, Zhifang Wang, Zhiyin Jiao, Qi Du, Xinyue Jia, Jingtian Niu, Ruiheng Du, Guisu Ji, Pengwei Duan, Peng Lv, Junfeng Cao. Integrating transcriptome and physiological analyses to elucidate the molecular responses of sorghum to fluxofenim and metolachlor herbicide. Pesticide biochemistry and physiology. 2023 Dec; 197(?):105692. doi: 10.1016/j.pestbp.2023.105692. [PMID: 38072547]
  • Przemysław Bernat, Anna Jasińska, Katarzyna Niedziałkowska, Mirosława Słaba, Sylwia Różalska, Katarzyna Paraszkiewicz, Lidia Sas-Paszt, Hermann J Heipieper. Adaptation of the metolachlor-degrading fungus Trichoderma harzianum to the simultaneous presence of low-density polyethylene (LDPE) microplastics. Ecotoxicology and environmental safety. 2023 Nov; 267(?):115656. doi: 10.1016/j.ecoenv.2023.115656. [PMID: 37944463]
  • P V Silva, B F Schedenffeldt, E S Medeiros, D Z Molina, M K Pagliarini, P A V Salmazo, M Mauad, P A Monquero, F C Munaro, L Y Shirota, G P Silva, M S Monteiro, R D C Dias, R P N Borges. Selectivity of herbicides used in corn on Crotalaria ochroleuca G. Don. Brazilian journal of biology = Revista brasleira de biologia. 2023; 83(?):e277798. doi: 10.1590/1519-6984.277798. [PMID: 38126645]
  • Lirui Ren, Wenjing Li, Qingjie Li, Daqi Zhang, Wensheng Fang, Dongdong Yan, Yuan Li, Qiuxia Wang, Xi Jin, Aocheng Cao. Metolachlor metal-organic framework nanoparticles for reducing leaching, ecotoxicity and improving bioactivity. Pest management science. 2022 Dec; 78(12):5366-5378. doi: 10.1002/ps.7159. [PMID: 36057859]
  • Juan Cruz Carrizo, Sung Vo Duy, Gabriel Munoz, Guido Marconi, María Valeria Amé, Sébastien Sauvé. Suspect screening of pharmaceuticals, illicit drugs, pesticides, and other emerging contaminants in Argentinean Piaractus mesopotamicus, a fish species used for local consumption and export. Chemosphere. 2022 Dec; 309(Pt 1):136769. doi: 10.1016/j.chemosphere.2022.136769. [PMID: 36209849]
  • Yuxin Zhang, Qinghao Liu, Wangcang Su, Lanlan Sun, Hongle Xu, Fei Xue, Chuantao Lu, Renhai Wu. The mechanism of exogenous gibberellin A3 protecting sorghum shoots from S-metolachlor Phytotoxicity. Pest management science. 2022 Nov; 78(11):4497-4506. doi: 10.1002/ps.7068. [PMID: 35797427]
  • Zhuanzhuan Sun, Mawuli Dzakpasu, Dongxian Zhang, Guochen Liu, Zhenzhen Wang, Miaowen Qu, Rong Chen, Xiaochang C Wang, Yucong Zheng. Enantioselectivity and mechanisms of chiral herbicide biodegradation in hydroponic systems. Chemosphere. 2022 Nov; 307(Pt 1):135701. doi: 10.1016/j.chemosphere.2022.135701. [PMID: 35842049]
  • Anna Jasińska, Sylwia Różalska, Volha Rusetskaya, Mirosława Słaba, Przemysław Bernat. Microplastic-Induced Oxidative Stress in Metolachlor-Degrading Filamentous Fungus Trichoderma harzianum. International journal of molecular sciences. 2022 Oct; 23(21):. doi: 10.3390/ijms232112978. [PMID: 36361770]
  • Kang Ou-Yang, Tangqi Feng, Yifang Han, Guangyu Li, Jianhong Li, Hongju Ma. Bioaccumulation, metabolism and endocrine-reproductive effects of metolachlor and its S-enantiomer in adult zebrafish (Danio rerio). The Science of the total environment. 2022 Jan; 802(?):149826. doi: 10.1016/j.scitotenv.2021.149826. [PMID: 34455281]
  • Seth A Strom, Aaron G Hager, Jeanaflor Crystal T Concepcion, Nicholas J Seiter, Adam S Davis, James A Morris, Shiv S Kaundun, Dean E Riechers. Metabolic Pathways for S-Metolachlor Detoxification Differ Between Tolerant Corn and Multiple-Resistant Waterhemp. Plant & cell physiology. 2021 Dec; 62(11):1770-1785. doi: 10.1093/pcp/pcab132. [PMID: 34453831]
  • Qian Qu, Yan Li, Zhenyan Zhang, Hengzheng Cui, Qianqiu Zhao, Wanyue Liu, Tao Lu, Haifeng Qian. Effects of S-metolachlor on wheat (Triticum aestivum L.) seedling root exudates and the rhizosphere microbiome. Journal of hazardous materials. 2021 06; 411(?):125137. doi: 10.1016/j.jhazmat.2021.125137. [PMID: 33858101]
  • Xile Deng, Wenna Zheng, Can Jin, Qingcai Zhan, Lianyang Bai. Novel phenylpyrimidine derivatives containing a hydrazone moiety protect rice seedlings from injury by metolachlor. Bioorganic chemistry. 2021 03; 108(?):104645. doi: 10.1016/j.bioorg.2021.104645. [PMID: 33493931]
  • Manuela D Machado, Eduardo V Soares. Exposure of the alga Pseudokirchneriella subcapitata to environmentally relevant concentrations of the herbicide metolachlor: Impact on the redox homeostasis. Ecotoxicology and environmental safety. 2021 Jan; 207(?):111264. doi: 10.1016/j.ecoenv.2020.111264. [PMID: 32911184]
  • Nuohan Xu, Qian Qu, Zhenyan Zhang, Wenting Yuan, Hengzheng Cui, Yijia Shen, Wei Lin, Tao Lu, Haifeng Qian. Effects of residual S-metolachlor in soil on the phyllosphere microbial communities of wheat (Triticum aestivum L.). The Science of the total environment. 2020 Dec; 748(?):141342. doi: 10.1016/j.scitotenv.2020.141342. [PMID: 32818888]
  • Xile Deng, Wenna Zheng, Qingcai Zhan, Yanan Deng, Yong Zhou, Lianyang Bai. New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy. Molecules (Basel, Switzerland). 2020 Oct; 25(21):. doi: 10.3390/molecules25214986. [PMID: 33126493]
  • Paola Olaya-Arenas, Kayleigh Hauri, Michael E Scharf, Ian Kaplan. Larval pesticide exposure impacts monarch butterfly performance. Scientific reports. 2020 09; 10(1):14490. doi: 10.1038/s41598-020-71211-7. [PMID: 32879347]
  • Ehssan Torabi, Charline Wiegert, Benoît Guyot, Stéphane Vuilleumier, Gwenaël Imfeld. Dissipation of S-metolachlor and butachlor in agricultural soils and responses of bacterial communities: Insights from compound-specific isotope and biomolecular analyses. Journal of environmental sciences (China). 2020 Jun; 92(?):163-175. doi: 10.1016/j.jes.2020.02.009. [PMID: 32430119]
  • Lan Wei, Yufen Huang, Lianxi Huang, Yanliang Li, Qing Huang, Guizhi Xu, Karin Müller, Hailong Wang, Yong Sik Ok, Zhongzhen Liu. The ratio of H/C is a useful parameter to predict adsorption of the herbicide metolachlor to biochars. Environmental research. 2020 05; 184(?):109324. doi: 10.1016/j.envres.2020.109324. [PMID: 32163771]
  • Justyna Nykiel-Szymańska, Sylwia Różalska, Przemysław Bernat, Mirosława Słaba. Assessment of oxidative stress and phospholipids alterations in chloroacetanilides-degrading Trichoderma spp. Ecotoxicology and environmental safety. 2019 Nov; 184(?):109629. doi: 10.1016/j.ecoenv.2019.109629. [PMID: 31509783]
  • Ivan Panfili, Maria Luce Bartucca, Giovanni Marrollo, Giovanni Povero, Daniele Del Buono. Application of a Plant Biostimulant To Improve Maize (Zea mays) Tolerance to Metolachlor. Journal of agricultural and food chemistry. 2019 Nov; 67(44):12164-12171. doi: 10.1021/acs.jafc.9b04949. [PMID: 31600067]
  • Jeanne Dollinger, Chung-Ho Lin, Ranjith P Udawatta, Valérie Pot, Pierre Benoit, Shibu Jose. Influence of agroforestry plant species on the infiltration of S-Metolachlor in buffer soils. Journal of contaminant hydrology. 2019 Aug; 225(?):103498. doi: 10.1016/j.jconhyd.2019.103498. [PMID: 31103926]
  • Alzbeta Stara, Jan Kubec, Eliska Zuskova, Milos Buric, Caterina Faggio, Antonin Kouba, Josef Velisek. Effects of S-metolachlor and its degradation product metolachlor OA on marbled crayfish (Procambarus virginalis). Chemosphere. 2019 Jun; 224(?):616-625. doi: 10.1016/j.chemosphere.2019.02.187. [PMID: 30849622]
  • Irene B Gutiérrez, Andreia F C Mesquita, Cláudia Nunes, Manuel A Coimbra, Fernando J M Gonçalves, João C Marques, Ana M M Gonçalves. Impacts of S-metolachlor and terbuthylazine in fatty acid and carbohydrate composition of the benthic clam Scrobicularia plana. Ecotoxicology and environmental safety. 2019 May; 173(?):293-304. doi: 10.1016/j.ecoenv.2019.02.034. [PMID: 30776562]
  • Josef Velisek, Alzbeta Stara, Eliska Zuskova, Jan Kubec, Milos Buric, Antonin Kouba. Chronic toxicity of metolachlor OA on growth, ontogenetic development, antioxidant biomarkers and histopathology of early life stages of marbled crayfish. The Science of the total environment. 2018 Dec; 643(?):1456-1463. doi: 10.1016/j.scitotenv.2018.06.309. [PMID: 30189562]
  • Dubravka Špoljarić Maronić, Ivna Štolfa Čamagajevac, Janja Horvatić, Tanja Žuna Pfeiffer, Filip Stević, Neven Žarković, Georg Waeg, Morana Jaganjac. S-metolachlor promotes oxidative stress in green microalga Parachlorella kessleri - A potential environmental and health risk for higher organisms. The Science of the total environment. 2018 Oct; 637-638(?):41-49. doi: 10.1016/j.scitotenv.2018.04.433. [PMID: 29751315]
  • Sohaib Aslam, Akhtar Iqbal, François Lafolie, Sylvie Recous, Pierre Benoit, Patricia Garnier. Mulch of plant residues at the soil surface impact the leaching and persistence of pesticides: A modelling study from soil columns. Journal of contaminant hydrology. 2018 07; 214(?):54-64. doi: 10.1016/j.jconhyd.2018.05.008. [PMID: 29871763]
  • Amelie Schmolke, Richard Brain, Pernille Thorbek, Daniel Perkins, Valery Forbes. Assessing and mitigating simulated population-level effects of 3 herbicides to a threatened plant: Application of a species-specific population model of Boltonia decurrens. Environmental toxicology and chemistry. 2018 06; 37(6):1545-1555. doi: 10.1002/etc.4093. [PMID: 29341229]
  • Nathalie Coquillé, Dominique Ménard, Julien Rouxel, Valentin Dupraz, Mélissa Éon, Patrick Pardon, Hélène Budzinski, Soizic Morin, Édith Parlanti, Sabine Stachowski-Haberkorn. The influence of natural dissolved organic matter on herbicide toxicity to marine microalgae is species-dependent. Aquatic toxicology (Amsterdam, Netherlands). 2018 May; 198(?):103-117. doi: 10.1016/j.aquatox.2018.02.019. [PMID: 29529466]
  • Devashan Naidoo, Lenka Poštová Slavětínská, Adeyemi O Aremu, Jiri Gruz, Ondrej Biba, Karel Doležal, Johannes Van Staden, Jeffrey F Finnie. Metabolite profiling and isolation of biologically active compounds from Scadoxus puniceus, a highly traded South African medicinal plant. Phytotherapy research : PTR. 2018 Apr; 32(4):625-630. doi: 10.1002/ptr.6000. [PMID: 29226479]
  • Ramdas G Kanissery, Allana Welsh, Andres Gomez, Lynn Connor, Gerald K Sims. Identification of metolachlor mineralizing bacteria in aerobic and anaerobic soils using DNA-stable isotope probing. Biodegradation. 2018 04; 29(2):117-128. doi: 10.1007/s10532-017-9817-6. [PMID: 29285669]
  • Dongzhi Li, Qinggang Gao, Li Xu, Sen Pang, Zhiqian Liu, Chengju Wang, Weiming Tan. Characterization of glutathione S-transferases in the detoxification of metolachlor in two maize cultivars of differing herbicide tolerance. Pesticide biochemistry and physiology. 2017 Nov; 143(?):265-271. doi: 10.1016/j.pestbp.2016.12.003. [PMID: 29183603]
  • Li Chen, Dezhen Wang, Zhongnan Tian, Shanshan Di, Wenjun Zhang, Fang Wang, Zhiqiang Zhou, Jinling Diao. Comparative toxic responses of male and female lizards (Eremias argus) exposed to (S)-metolachlor-contaminated soil. Environmental pollution (Barking, Essex : 1987). 2017 Aug; 227(?):476-483. doi: 10.1016/j.envpol.2017.05.006. [PMID: 28494399]
  • Elżbieta Wołejko, Piotr Kaczyński, Bożena Łozowicka, Urszula Wydro, Andrzej Borusiewicz, Izabela Hrynko, Rafał Konecki, Krystyna Snarska, Dorota Dec, Paweł Malinowski. Dissipation of S-metolachlor in plant and soil and effect on enzymatic activities. Environmental monitoring and assessment. 2017 Jul; 189(7):355. doi: 10.1007/s10661-017-6071-7. [PMID: 28656556]
  • Matthew T Moore, Martin A Locke, Robert Kröger. Mitigation of atrazine, S-metolachlor, and diazinon using common emergent aquatic vegetation. Journal of environmental sciences (China). 2017 Jun; 56(?):114-121. doi: 10.1016/j.jes.2016.09.009. [PMID: 28571845]
  • C Quintaneiro, D Patrício, S C Novais, A M V M Soares, M S Monteiro. Endocrine and physiological effects of linuron and S-metolachlor in zebrafish developing embryos. The Science of the total environment. 2017 May; 586(?):390-400. doi: 10.1016/j.scitotenv.2016.11.153. [PMID: 28209406]
  • Lan Wei, Yufen Huang, Yanliang Li, Lianxi Huang, Nyo Nyo Mar, Qing Huang, Zhongzhen Liu. Biochar characteristics produced from rice husks and their sorption properties for the acetanilide herbicide metolachlor. Environmental science and pollution research international. 2017 Feb; 24(5):4552-4561. doi: 10.1007/s11356-016-8192-x. [PMID: 27957688]
  • C Bedos, L Alletto, B Durand, O Fanucci, A Brut, M Bourdat-Deschamps, S Giuliano, B Loubet, E Ceschia, P Benoit. Observed volatilization fluxes of S-metolachlor and benoxacor applied on soil with and without crop residues. Environmental science and pollution research international. 2017 Feb; 24(4):3985-3996. doi: 10.1007/s11356-016-8124-9. [PMID: 27915427]
  • Dongzhi Li, Li Xu, Sen Pang, Zhiqian Liu, Kai Wang, Chengju Wang. Variable Levels of Glutathione S-Transferases Are Responsible for the Differential Tolerance to Metolachlor between Maize (Zea mays) Shoots and Roots. Journal of agricultural and food chemistry. 2017 Jan; 65(1):39-44. doi: 10.1021/acs.jafc.6b04129. [PMID: 27992212]
  • Roberto Busi, Stephen B Powles. Cross-resistance to prosulfocarb + S-metolachlor and pyroxasulfone selected by either herbicide in Lolium rigidum. Pest management science. 2016 Sep; 72(9):1664-72. doi: 10.1002/ps.4253. [PMID: 26864800]
  • Elodie Maillard, Jens Lange, Steffi Schreiber, Jeanne Dollinger, Barbara Herbstritt, Maurice Millet, Gwenaël Imfeld. Dissipation of hydrological tracers and the herbicide S-metolachlor in batch and continuous-flow wetlands. Chemosphere. 2016 Feb; 144(?):2489-96. doi: 10.1016/j.chemosphere.2015.11.027. [PMID: 26630289]
  • 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]
  • Stephanie Hedrei Helmer, Anahi Kerbaol, Philippe Aras, Catherine Jumarie, Monique Boily. Effects of realistic doses of atrazine, metolachlor, and glyphosate on lipid peroxidation and diet-derived antioxidants in caged honey bees (Apis mellifera). Environmental science and pollution research international. 2015 Jun; 22(11):8010-21. doi: 10.1007/s11356-014-2879-7. [PMID: 24728576]
  • Sohaib Aslam, Akhtar Iqbal, Marjolaine Deschamps, Sylvie Recous, Patricia Garnier, Pierre Benoit. Effect of rainfall regimes and mulch decomposition on the dissipation and leaching of S-metolachlor and glyphosate: a soil column experiment. Pest management science. 2015 Feb; 71(2):278-91. doi: 10.1002/ps.3803. [PMID: 24753267]
  • A Cassigneul, L Alletto, P Benoit, V Bergheaud, V Etiévant, V Dumény, A L Le Gac, D Chuette, C Rumpel, E Justes. Nature and decomposition degree of cover crops influence pesticide sorption: quantification and modelling. Chemosphere. 2015 Jan; 119(?):1007-1014. doi: 10.1016/j.chemosphere.2014.08.082. [PMID: 25303661]
  • Xinke Tang, Xiaomao Zhou, Jing Wu, Jingbo Li, Lianyang Bai. A novel function of sanshools: the alleviation of injury from metolachlor in rice seedlings. Pesticide biochemistry and physiology. 2014 Mar; 110(?):44-9. doi: 10.1016/j.pestbp.2014.02.006. [PMID: 24759050]
  • Sohaib Aslam, Patricia Garnier, Cornelia Rumpel, Serge E Parent, Pierre Benoit. Adsorption and desorption behavior of selected pesticides as influenced by decomposition of maize mulch. Chemosphere. 2013 Jun; 91(11):1447-55. doi: 10.1016/j.chemosphere.2012.12.005. [PMID: 23434076]
  • Yongnian Ni, Fangyuan Zhang, Serge Kokot. Enantioselective binding interaction of the metolachlor pesticide enatiomers with bovine serum albumin--a spectroscopic analysis study. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2012 Nov; 97(?):753-61. doi: 10.1016/j.saa.2012.07.063. [PMID: 22898111]
  • Min Zhang, Xiao-Hua Xu, Yan Cui, Long-Guan Xie, Chui-Hua Kong. Synthesis and herbicidal potential of substituted aurones. Pest management science. 2012 Nov; 68(11):1512-22. doi: 10.1002/ps.3339. [PMID: 22718431]
  • Huijun Liu, Ruonan Huang, Fei Xie, Shuxian Zhang, Jiang Shi. Enantioselective phytotoxicity of metolachlor against maize and rice roots. Journal of hazardous materials. 2012 May; 217-218(?):330-7. doi: 10.1016/j.jhazmat.2012.03.037. [PMID: 22483442]
  • Zisis Vryzas, Emmanuel Nikolaos Papadakis, E Papadopoulou-Mourkidou. Leaching of Br-, metolachlor, alachlor, atrazine, deethylatrazine and deisopropylatrazine in clayey vadoze zone: a field scale experiment in north-east Greece. Water research. 2012 Apr; 46(6):1979-89. doi: 10.1016/j.watres.2012.01.021. [PMID: 22325931]
  • Alison L Clune, P Barry Ryan, Dana Boyd Barr. Have regulatory efforts to reduce organophosphorus insecticide exposures been effective?. Environmental health perspectives. 2012 Apr; 120(4):521-5. doi: 10.1289/ehp.1104323. [PMID: 22251442]
  • Fabiola G Zuno-Floriano, Marion G Miller, Maria L Aldana-Madrid, Matt J Hengel, Nilesh W Gaikwad, Vladimir Tolstikov, Ana G Contreras-Cortés. Effect of Acinetobacter sp on metalaxyl degradation and metabolite profile of potato seedlings (Solanum tuberosum L.) alpha variety. PloS one. 2012; 7(2):e31221. doi: 10.1371/journal.pone.0031221. [PMID: 22363586]
  • Hui J Liu, Ming Y Xiong, Bao L Tian. Comparative phytotoxicity of Rac-metolachlor and S-metolachlor on rice seedlings. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2012; 47(5):410-9. doi: 10.1080/03601234.2012.657046. [PMID: 22424066]
  • Sen Pang, Liusheng Duan, Zhiqian Liu, Xiaoyu Song, Xuefeng Li, Chengju Wang. Co-induction of a glutathione-S-transferase, a glutathione transporter and an ABC transporter in maize by xenobiotics. PloS one. 2012; 7(7):e40712. doi: 10.1371/journal.pone.0040712. [PMID: 22792398]
  • Francielle Tatiane Mathias, Renata Marino Romano, Hanan Kaled Sleiman, Claudio Alvarenga de Oliveira, Marco Aurelio Romano. Herbicide metolachlor causes changes in reproductive endocrinology of male wistar rats. ISRN toxicology. 2012; 2012(?):130846. doi: 10.5402/2012/130846. [PMID: 23724293]
  • Sen Pang, Zhaojin Ran, Zhiqian Liu, Xiaoyu Song, Liusheng Duan, Xuefeng Li, Chengju Wang. Enantioselective induction of a glutathione-S-transferase, a glutathione transporter and an ABC transporter in maize by Metolachlor and its (S)-isomer. PloS one. 2012; 7(10):e48085. doi: 10.1371/journal.pone.0048085. [PMID: 23144728]
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