Methyl parathion (BioDeep_00000001404)
Secondary id: BioDeep_00001871698
human metabolite blood metabolite Industrial Pollutants
代谢物信息卡片
Phosphorothioic acid, O,O-dimethyl O-(4-nitrophenyl) ester
化学式: C8H10NO5PS (263.0017)
中文名称: 甲基对硫磷
谱图信息:
最多检出来源 Homo sapiens(blood) 25.74%
Reviewed
Last reviewed on 2024-08-21.
Cite this Page
Methyl parathion. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/methyl_parathion (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000001404). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: COP(=S)(OC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI: InChI=1S/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3
描述信息
Methyl parathion is an insecticide that does not occur naturally in the environment. Pure methyl parathion exists as white crystals. Impure methyl parathion is a brownish liquid that smells like rotten eggs.Methyl parathion is used to kill insects on farm crops, especially cotton. The EPA now restricts how methyl parathion can be used and applied; only trained people are allowed to spray it. Methyl parathion can no longer be used on food crops commonly consumed by children.
Methyl parathion is a white crystalline solid which is often dissolved in a liquid solvent carrier. The commercial product is a tan liquid (xylene solution) with a pungent odor. It is slightly soluble to insoluble in water. Usually with the liquid solvent it is a combustible liquid. It is toxic by inhalation, ingestion and skin absorption. It is used as an insecticide.
Parathion-methyl is a C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an acaricide, an agrochemical, a genotoxin, an environmental contaminant and an antifungal agent. It is an organic thiophosphate, an organothiophosphate insecticide and a C-nitro compound. It is functionally related to a 4-nitrophenol.
同义名列表
24 个代谢物同义名
Phosphorothioic acid, O,O-dimethyl O-(4-nitrophenyl) ester; Phosphorothioic acid, O,O-dimethyl-O-p-nitrophenyl ester; Phosphorothioate, O,O-dimethyl O-(4-nitrophenyl) ester; Phosphorothioate, O,O-dimethyl-O-p-nitrophenyl ester; O,O-Dimethyl O-(p-nitrophenyl) thionophosphoric acid; O,O-Dimethyl O-(p-nitrophenyl) thionophosphate; O,O-dimethyl O-4-nitrophenyl phosphorothioate; Dimethyl p-nitrophenyl thiophosphoric acid; Dimethyl p-nitrophenyl thiophosphate; Dimethyl parathion; METHYL PARATHIONE; Parathion-methyl; Methyl parathion; Parathion methyl; Methylparathion; Metacid 50; Metaphos; Wofatox; Vofatox; α-gro; Dalf; PATM; Parathion-methyl; Methyl parathion
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:38746
- KEGG: C14228
- PubChem: 4130
- HMDB: HMDB0256125
- Metlin: METLIN44552
- ChEMBL: CHEMBL346516
- Wikipedia: Parathion methyl
- MeSH: Methyl Parathion
- chemspider: 3987
- CAS: 298-00-0
- MoNA: AU261603
- MoNA: AU261601
- MoNA: SM848103
- MoNA: AU261602
- MoNA: AU261605
- MoNA: AU261606
- PMhub: MS000000452
- NIKKAJI: J2.981E
- RefMet: Parathion-methyl
- PubChem: 7847038
- KNApSAcK: 38746
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
6 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(6)
- methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate - methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate - methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate - methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate - methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate - methyl parathion degradation:
H2O + methyl parathion ⟶ 4-nitrophenol + H+ + dimethylthiophosphate
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
- Rafael J G Rubira, Victor R G Batista, Rafael R Correia, Wallance M Pazin, Mateus D Maximino, Gilia C M Ruiz, Giovana R Teixeira, Aldo E Job. Biological responses to imazapic and methyl parathion pesticides in bioinspired lipid membranes and Tilapia fish.
Journal of hazardous materials.
2023 09; 458(?):131943. doi:
10.1016/j.jhazmat.2023.131943. [PMID: 37390683] - Shivani Chhillar, Vipul Batra, Arumugam Kumaresan, Rakesh Kumar, Ankit Pal, Tirtha Kumar Datta. Acute exposure to organophosphorus pesticide metabolites compromises buffalo sperm function and impairs fertility.
Scientific reports.
2023 06; 13(1):9102. doi:
10.1038/s41598-023-35541-6. [PMID: 37277402] - Zhao Ma, Yuanbo Li, Chao Lu, Meng Li. On-site screening method for bioavailability assessment of the organophosphorus pesticide, methyl parathion, and its primary metabolite in soils by paper strip biosensor.
Journal of hazardous materials.
2023 May; 457(?):131725. doi:
10.1016/j.jhazmat.2023.131725. [PMID: 37295330] - Hongyuan Zhao, Bo Li, Runqiang Liu, Yuqi Chang, Hongliang Wang, Lin Zhou, Sridhar Komarneni. Ultrasonic-assisted preparation of halloysite nanotubes/zirconia/carbon black nanocomposite for the highly sensitive determination of methyl parathion.
Materials science & engineering. C, Materials for biological applications.
2021 Apr; 123(?):111982. doi:
10.1016/j.msec.2021.111982. [PMID: 33812610] - Huiyu Zhao, Barbara Bojko, Fengmao Liu, Janusz Pawliszyn, Wei Peng, Xinquan Wang. Mechanism of interactions between organophosphorus insecticides and human serum albumin: Solid-phase microextraction, thermodynamics and computational approach.
Chemosphere.
2020 Aug; 253(?):126698. doi:
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Toxicology.
2020 05; 438(?):152463. doi:
10.1016/j.tox.2020.152463. [PMID: 32294493] - Michael Eddleston, R Eddie Clutton, Matthew Taylor, Adrian Thompson, Franz Worek, Harald John, Horst Thiermann, Colin Scott. Efficacy of an organophosphorus hydrolase enzyme (OpdA) in human serum and minipig models of organophosphorus insecticide poisoning.
Clinical toxicology (Philadelphia, Pa.).
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Environment international.
2019 12; 133(Pt B):105243. doi:
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Analytica chimica acta.
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Aquatic toxicology (Amsterdam, Netherlands).
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Ecotoxicology and environmental safety.
2011 Oct; 74(7):2112-8. doi:
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Human & experimental toxicology.
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Fish physiology and biochemistry.
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Toxicology and applied pharmacology.
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Chemosphere.
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Ecotoxicology and environmental safety.
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Environmental science & technology.
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Toxicology and applied pharmacology.
2006 Oct; 216(2):216-24. doi:
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Archives of toxicology.
2006 Jul; 80(7):449-57. doi:
10.1007/s00204-006-0071-7. [PMID: 16496128] - Hui-fang Yan, Ya-juan Pan, Jian Wang, Fu-gang Zhang, Xiao-shuang Xie, Jing Zhang, Chun-ling Li. [High performance thin layer chromatography quality assessment of Rogor, methyl parathion, methamidophos and dichlorvos in serum].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2006 Jul; 24(7):437-8. doi:
NULL. [PMID: 16889713] - M T Moore, E R Bennett, C M Cooper, S Smith, J L Farris, K G Drouillard, R Schulz. Influence of vegetation in mitigation of methyl parathion runoff.
Environmental pollution (Barking, Essex : 1987).
2006 Jul; 142(2):288-94. doi:
10.1016/j.envpol.2005.10.009. [PMID: 16314013] - Diana Amaral Monteiro, Jeane Alves de Almeida, Francisco Tadeu Rantin, Ana Lúcia Kalinin. Oxidative stress biomarkers in the freshwater characid fish, Brycon cephalus, exposed to organophosphorus insecticide Folisuper 600 (methyl parathion).
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2006 Jun; 143(2):141-9. doi:
10.1016/j.cbpc.2006.01.004. [PMID: 16546452] - Yu-Ji Jiang, You-Jin Deng, Xin-Rui Liu, Bao-Gui Xie, Fang-Ping Hu. [Isolation and identification of a bacterial strain JS018 capable of degrading several kinds of organophosphate pesticides].
Wei sheng wu xue bao = Acta microbiologica Sinica.
2006 Jun; 46(3):463-6. doi:
. [PMID: 16933622] - Ping Liu, Wei-Hua Wen, Xiao-Xiao Song, Wei-Hong Yuan. [Effects of mixed cypermethrin and methylparathion on endocrine hormone levels and immune functions in rats: I. Dose-response relationship].
Wei sheng yan jiu = Journal of hygiene research.
2006 May; 35(3):257-60. doi:
. [PMID: 16921741] - Axel Muttray, Gerhard Bäcker, Detlev Jung, Georg Hill, Stephan Letzel. External and internal exposure of wine growers spraying methyl parathion.
Toxicology letters.
2006 Apr; 162(2-3):219-24. doi:
10.1016/j.toxlet.2005.09.013. [PMID: 16242869] - Michael A Caprio, Tim Nowatzki, Blair Siegfried, Lance J Meinke, Robert J Wright, Larry D Chandler. Assessing risk of resistance to aerial applications of methyl-parathion in western corn rootworm (Coleoptera: Chrysomelidae).
Journal of economic entomology.
2006 Apr; 99(2):483-93. doi:
10.1603/0022-0493-99.2.483. [PMID: 16686151] - Eloisa Caldas, Andreia Jardim, Arpad Ambrus, Luiz Cesar Souza. Variability of organophosphorus insecticide residues in large size crops grown in commercial farms in Brazil.
Food additives and contaminants.
2006 Feb; 23(2):148-58. doi:
10.1080/02652030500479708. [PMID: 16449057] - Kushik Jaga, Chandrabhan Dharmani. Methyl parathion: an organophosphate insecticide not quite forgotten.
Reviews on environmental health.
2006 Jan; 21(1):57-67. doi:
10.1515/reveh.2006.21.1.57. [PMID: 16700430] - E Suprun, G Evtugyn, H Budnikov, F Ricci, D Moscone, G Palleschi. Acetylcholinesterase sensor based on screen-printed carbon electrode modified with prussian blue.
Analytical and bioanalytical chemistry.
2005 Oct; 383(4):597-604. doi:
10.1007/s00216-005-0002-0. [PMID: 16163484] - Celine Chouteau, Sergei Dzyadevych, Claude Durrieu, Jean-Marc Chovelon. A bi-enzymatic whole cell conductometric biosensor for heavy metal ions and pesticides detection in water samples.
Biosensors & bioelectronics.
2005 Aug; 21(2):273-81. doi:
10.1016/j.bios.2004.09.032. [PMID: 16023954] - Jenny A Stebbing, Lance J Meinke, Steve E Naranjo, Blair D Siegfried, Robert J Wright, Laurence D Chandler. Flight behavior of methyl-parathion-resistant and -susceptible western corn rootworm (Coleoptera: Chrysomelidae) populations from Nebraska.
Journal of economic entomology.
2005 Aug; 98(4):1294-304. doi:
10.1603/0022-0493-98.4.1294. [PMID: 16156583] - Swen Follak, Frank Walker, Karl Hurle. Short- and long-term response of sunflower to airborne bromoxynil-octanoate under controlled and field conditions.
Ecotoxicology (London, England).
2005 Jul; 14(5):503-11. doi:
10.1007/s10646-005-0007-7. [PMID: 16220358] - Ender Içen, Ferah Armutçu, Kemal Büyükgüzel, Ahmet Gürel. Biochemical stress indicators of greater wax moth exposure to organophosphorus insecticides.
Journal of economic entomology.
2005 Apr; 98(2):358-66. doi:
. [PMID: 15889724] - Sukhdeep Kaur, C K Dhanju. Biochemical effects of some organophosphorus pesticides on the ovaries of albino rats.
Indian journal of physiology and pharmacology.
2005 Apr; 49(2):148-52. doi:
". [PMID: 16170982] - Naoki Kunugita, Tsunehiro Oyama, Toshihiro Kawamoto. [p-Nitrophenol].
Nihon rinsho. Japanese journal of clinical medicine.
2004 Dec; 62 Suppl 12(?):495-7. doi:
NULL. [PMID: 15658373] - Sukhdeep Kaur, C K Dhanju. Enzymatic changes induced by some organophosphorus pesticides in female rats.
Indian journal of experimental biology.
2004 Oct; 42(10):1017-9. doi:
NULL. [PMID: 15511008] - C D Milam, J L Bouldin, J L Farris, R Schulz, M T Moore, E R Bennett, C M Cooper, S Smith. Evaluating acute toxicity of methyl parathion application in constructed wetland mesocosms.
Environmental toxicology.
2004 Oct; 19(5):471-9. doi:
10.1002/tox.20052. [PMID: 15352263] - H Tsoukali, N Raikos, G Theodoridis, D Psaroulis. Headspace solid phase microextraction for the gas chromatographic analysis of methyl-parathion in post-mortem human samples. Application in a suicide case by intravenous injection.
Forensic science international.
2004 Jul; 143(2-3):127-32. doi:
10.1016/j.forsciint.2004.02.032. [PMID: 15240032] - Lucia Helena de Aguiar, Gilberto Moraes, Ive Marchioni Avilez, Alexandre Eneas Altran, Cristina Ferro Corrêa. Metabolical effects of Folidol 600 on the neotropical freshwater fish matrinxã, Brycon cephalus.
Environmental research.
2004 Jun; 95(2):224-30. doi:
10.1016/s0013-9351(03)00119-1. [PMID: 15147928] - R Gonzalez Ortíz, L Martínez-Tabche, S O Terrón. Effects of cimetidine and phenobarbital on methylparathion metabolism in Hyalella azteca.
Bulletin of environmental contamination and toxicology.
2004 Jun; 72(6):1247-52. doi:
10.1007/s00128-004-0377-1. [PMID: 15362456] - André Wolters, Minze Leistra, Volker Linnemann, Michael Klein, Andreas Schäffer, Harry Vereecken. Pesticide volatilization from plants: improvement of the PEC model PELMO based on a boundary-layer concept.
Environmental science & technology.
2004 May; 38(10):2885-93. doi:
10.1021/es035061m. [PMID: 15212264] - Lei Sun, Yanjie Dong, Yafeng Zhou, Maojun Yang, Chenggang Zhang, Zihe Rao, Xian-en Zhang. Crystallization and preliminary X-ray studies of methyl parathion hydrolase from Pseudomonas sp. WBC-3.
Acta crystallographica. Section D, Biological crystallography.
2004 May; 60(Pt 5):954-6. doi:
10.1107/s0907444904005669. [PMID: 15103151] - Subramanya Karanth, Jing Liu, Kenneth Olivier, Carey Pope. Interactive toxicity of the organophosphorus insecticides chlorpyrifos and methyl parathion in adult rats.
Toxicology and applied pharmacology.
2004 Apr; 196(2):183-90. doi:
10.1016/j.taap.2003.12.014. [PMID: 15081265] - Dílson Silva, Célia M Cortez, Jayme Cunha-Bastos, Sônia R W Louro. Methyl parathion interaction with human and bovine serum albumin.
Toxicology letters.
2004 Feb; 147(1):53-61. doi:
10.1016/j.toxlet.2003.10.014. [PMID: 14700528] - Elizabeth Pennisi. Society for Integrative and Comparative Biology meeting. Estrogen may disrupt nitrogen fixation.
Science (New York, N.Y.).
2004 Feb; 303(5660):950. doi:
10.1126/science.303.5660.950b. [PMID: 14963305] - Thomas Kromer, Holger Ophoff, Andreas Stork, Fritz Führ. Photodegradation and volatility of pesticides: chamber experiments.
Environmental science and pollution research international.
2004; 11(2):107-20. doi:
10.1007/bf02979710. [PMID: 15108858] - Hong Fang, Weida Tong, William S Branham, Carrie L Moland, Stacy L Dial, Huixiao Hong, Qian Xie, Roger Perkins, William Owens, Daniel M Sheehan. Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
Chemical research in toxicology.
2003 Oct; 16(10):1338-58. doi:
10.1021/tx030011g. [PMID: 14565775] - André Wolters, Thomas Kromer, Volker Linnemann, Andreas Schäffer, Harry Vereecken. A new tool for laboratory studies on volatilization: extension of applicability of the photovolatility chamber.
Environmental toxicology and chemistry.
2003 Apr; 22(4):791-7. doi:
10.1002/etc.5620220417. [PMID: 12685714] - Anna Yu Kolosova, Jung-Hyun Park, Sergey A Eremin, Sung-Jo Kang, Duck-Hwa Chung. Fluorescence polarization immunoassay based on a monoclonal antibody for the detection of the organophosphorus pesticide parathion-methyl.
Journal of agricultural and food chemistry.
2003 Feb; 51(5):1107-14. doi:
10.1021/jf025801v. [PMID: 12590442] - Srinivas Parimi, Michael E Scharf, Lance J Meinke, Laurence D Chandler, Blair D Siegfried. Inheritance of methyl-parathion resistance in Nebraska western corn rootworm populations (Coleoptera: Chrysomelidae).
Journal of economic entomology.
2003 Feb; 96(1):131-6. doi:
10.1603/0022-0493-96.1.131. [PMID: 12650355] - Dana B Barr, Wayman E Turner, Emily DiPietro, P Cheryl McClure, Samuel E Baker, John R Barr, Kimberly Gehle, Raymond E Grissom, Roberto Bravo, W Jack Driskell, Donald G Patterson, Robert H Hill, Larry L Needham, James L Pirkle, Eric J Sampson. Measurement of p-nitrophenol in the urine of residents whose homes were contaminated with methyl parathion.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1085-91. doi:
10.1289/ehp.02110s61085. [PMID: 12634145] - Yunxiu Hou, Fenghua Fu, Shiwen Liu, Chenghua Liu, Yihua Sun, Shicui Qiu. [The profiles of free organophosphorus poisons in the bile of rabbits poisoned with different organophosphates].
Zhonghua nei ke za zhi.
2002 Dec; 41(12):795-7. doi:
NULL. [PMID: 12654229] - Kenneth G McCann, C Michael Moomey, Kenny D Runkle, Daniel O Hryhorczuk, J Milton Clark, Dana B Barr. Chicago area methyl parathion response.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1075-8. doi:
10.1289/ehp.02110s61075. [PMID: 12634143] - Daniel O Hryhorczuk, Mike Moomey, Ann Burton, Ken Runkle, Edwin Chen, Tiffanie Saxer, Jennifer Slightom, John Dimos, Ken McCann, Dana Barr. Urinary p-nitrophenol as a biomarker of household exposure to methyl parathion.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1041-6. doi:
10.1289/ehp.02110s61041. [PMID: 12634137] - Carol Rubin, Emilio Esteban, Stephanie Kieszak, Robert H Hill, Boadie Dunlop, Rebecca Yacovac, Janine Trottier, Kathy Boylan, Terri Tomasewski, Ken Pearce. Assessment of human exposure and human health effects after indoor application of methyl parathion in Lorain County, Ohio, 1995-1996.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1047-51. doi:
10.1289/ehp.02110s61047. [PMID: 12634138] - Robert H Hill, Susan Head, Dana B Barr, Carol Rubin, Emilio Esteban, Samuel E Baker, Sandra Bailey, Larry L Needham. Public health decisions: the laboratory's role in the Lorain County, Ohio, investigation.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1057-9. doi:
10.1289/ehp.02110s61057. [PMID: 12634140] - J Milton Clark, John Bing-Canar, Steve Renninger, Ralph Dollhopf, Jason El-Zein, Dave Star, Dea Zimmerman, Abul Anisuzzaman, Kathline Boylan, Terrence Tomaszewski, Ken Pearce, Rebecca Yacovac, Bobby Erlwein, John Ward. Methyl parathion in residential properties: relocation and decontamination methodology.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1061-70. doi:
10.1289/ehp.02110s61061. [PMID: 12634141] - Carol Rubin, Emilio Esteban, Robert H Hill, Ken Pearce. Introduction--the methyl parathion story: a chronicle of misuse and preventable human exposure.
Environmental health perspectives.
2002 Dec; 110 Suppl 6(?):1037-40. doi:
10.1289/ehp.02110s61037. [PMID: 12634136] - Fadwa I Y Mostafa, Charles S Helling. Impact of four pesticides on the growth and metabolic activities of two photosynthetic algae.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.
2002 Sep; 37(5):417-44. doi:
10.1081/pfc-120014873. [PMID: 12369760] - D B Fragoso, R N C Guedes, R N C Guedes, M C Picanço, L Zambolim. Insecticide use and organophosphate resistance in the coffee leaf miner Leucoptera coffeella (Lepidoptera: Lyonetiidae).
Bulletin of entomological research.
2002 Jun; 92(3):203-12. doi:
10.1079/ber2002156. [PMID: 12088537]
