Diethyl-maleate

Not an inhibitor of alpha/beta hydrolases. Glutathione depleting agent. Used to test the involvment of glutathione-S-transferases in the resistance to insecticides. One of the key uses for the compound is in production of the pesticide Malathion

General

Type : Synergist of insecticide,Not A\/B H target

Chemical_Nomenclature : diethyl (Z)-but-2-enedioate

Canonical SMILES : CCOC(=O)C=CC(=O)OCC

InChI : InChI=1S\/C8H12O4\/c1-3-11-7(9)5-6-8(10)12-4-2\/h5-6H,3-4H2,1-2H3\/b6-5-

InChIKey : IEPRKVQEAMIZSS-WAYWQWQTSA-N

Other name(s) : DEM,Ethyl maleate,Diethylmaleate,Diethyl maleate,Maleic acid, diethyl ester,CHEBI:68508,CHEMBL2037000,ZINC100004207,SCHEMBL60423


MW : 172.18

Formula : C8H12O4

CAS_number : 141-05-9

PubChem : 5271566

UniChem : IEPRKVQEAMIZSS-WAYWQWQTSA-N

IUPHAR :

Wikipedia :

Target

Families :

Stucture :

Protein :

References (41)

Title : Solvent-dependent activity of Candida antarctica lipase B and its correlation with a regioselective mono aza-Michael addition - experimental and molecular dynamics simulation studies - Nazarian_2022_Heliyon_8_e10336
Author(s) : Nazarian Z , Arab SS
Ref : Heliyon , 8 :e10336 , 2022
Abstract : Nazarian_2022_Heliyon_8_e10336
ESTHER : Nazarian_2022_Heliyon_8_e10336
PubMedSearch : Nazarian_2022_Heliyon_8_e10336
PubMedID: 36090210

Title : Associations between acetylcholinesterase-1 mutations and chlorpyrifos resistance in beet armyworm, Spodoptera exigua - Teng_2022_Pestic.Biochem.Physiol_184_105105
Author(s) : Teng H , Zuo Y , Jin Z , Wu Y , Yang Y
Ref : Pestic Biochem Physiol , 184 :105105 , 2022
Abstract : Teng_2022_Pestic.Biochem.Physiol_184_105105
ESTHER : Teng_2022_Pestic.Biochem.Physiol_184_105105
PubMedSearch : Teng_2022_Pestic.Biochem.Physiol_184_105105
PubMedID: 35715044
Gene_locus related to this paper: spolt-ACHE1

Title : Multiple Mechanisms Conferring Broad-Spectrum Insecticide Resistance in the Tropical Bed Bug (Hemiptera: Cimicidae) - Dang_2021_J.Econ.Entomol__
Author(s) : Dang K , Doggett SL , Leong XY , Veera Singham G , Lee CY
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Abstract : Dang_2021_J.Econ.Entomol__
ESTHER : Dang_2021_J.Econ.Entomol__
PubMedSearch : Dang_2021_J.Econ.Entomol__
PubMedID: 34693975

Title : Metabolic Resistance in Permethrin-Resistant Florida Aedes aegypti (Diptera: Culicidae) - Schluep_2021_Insects_12_
Author(s) : Schluep SM , Buckner EA
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Abstract : Schluep_2021_Insects_12_
ESTHER : Schluep_2021_Insects_12_
PubMedSearch : Schluep_2021_Insects_12_
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Title : Field-evolved resistance to chlorpyrifos by Spodoptera frugiperda (Lepidoptera: Noctuidae): inheritance mode, cross-resistance patterns, and synergism - Garlet_2021_Pest.Manag.Sci__
Author(s) : Garlet CG , Gubiani PDS , Palharini RB , Moreira RP , Godoy DN , Farias JR , Bernardi O
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Abstract : Garlet_2021_Pest.Manag.Sci__
ESTHER : Garlet_2021_Pest.Manag.Sci__
PubMedSearch : Garlet_2021_Pest.Manag.Sci__
PubMedID: 34310024

Title : The overexpression of three cytochrome P450 genes CYP6CY14, CYP6CY22 and CYP6UN1 contributed to metabolic resistance to dinotefuran in melon\/cotton aphid, Aphis gossypii Glover - Chen_2020_Pestic.Biochem.Physiol_167_104601
Author(s) : Chen A , Zhang H , Shan T , Shi X , Gao X
Ref : Pestic Biochem Physiol , 167 :104601 , 2020
Abstract : Chen_2020_Pestic.Biochem.Physiol_167_104601
ESTHER : Chen_2020_Pestic.Biochem.Physiol_167_104601
PubMedSearch : Chen_2020_Pestic.Biochem.Physiol_167_104601
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Title : Biochemical Mechanisms, Cross-resistance and Stability of Resistance to Metaflumizone in Plutella xylostella - Shen_2020_Insects_11_
Author(s) : Shen J , Li Z , Li D , Wang R , Zhang S , You H , Li J
Ref : Insects , 11 : , 2020
Abstract : Shen_2020_Insects_11_
ESTHER : Shen_2020_Insects_11_
PubMedSearch : Shen_2020_Insects_11_
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Title : Fine-scale spatial and temporal variations in insecticide resistance in Culex pipiens complex mosquitoes in rural south-eastern Tanzania - Matowo_2019_Parasit.Vectors_12_413
Author(s) : Matowo NS , Abbasi S , Munhenga G , Tanner M , Mapua SA , Oullo D , Koekemoer LL , Kaindoa E , Ngowo HS , Coetzee M , Utzinger J , Okumu FO
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Abstract : Matowo_2019_Parasit.Vectors_12_413
ESTHER : Matowo_2019_Parasit.Vectors_12_413
PubMedSearch : Matowo_2019_Parasit.Vectors_12_413
PubMedID: 31443737

Title : Overexpression of multiple cytochrome P450 genes associated with sulfoxaflor resistance in Aphis gossypii Glover - Ma_2019_Pestic.Biochem.Physiol_157_204
Author(s) : Ma K , Tang Q , Zhang B , Liang P , Wang B , Gao X
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Abstract : Ma_2019_Pestic.Biochem.Physiol_157_204
ESTHER : Ma_2019_Pestic.Biochem.Physiol_157_204
PubMedSearch : Ma_2019_Pestic.Biochem.Physiol_157_204
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Title : Effect of Synergists on Deltamethrin Resistance in the Common Bed Bug (Hemiptera: Cimicidae) - Gonzalez-Morales_2019_J.Econ.Entomol_112_786
Author(s) : Gonzalez-Morales MA , Romero A
Ref : J Econ Entomol , 112 :786 , 2019
Abstract : Gonzalez-Morales_2019_J.Econ.Entomol_112_786
ESTHER : Gonzalez-Morales_2019_J.Econ.Entomol_112_786
PubMedSearch : Gonzalez-Morales_2019_J.Econ.Entomol_112_786
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Title : Determination of metabolic resistance mechanisms in pyrethroid-resistant and fipronil-tolerant brown dog ticks - Eiden_2017_Med.Vet.Entomol_31_243
Author(s) : Eiden AL , Kaufman PE , Oi FM , Dark MJ , Bloomquist JR , Miller RJ
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PubMedSearch : Eiden_2017_Med.Vet.Entomol_31_243
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Title : Pyrethroid resistance in Phytoseiulus macropilis (Acari: Phytoseiidae): cross-resistance, stability and effect of synergists - Queiroz_2016_Exp.Appl.Acarol_68_71
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PubMedSearch : Queiroz_2016_Exp.Appl.Acarol_68_71
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Title : Insecticides resistance in the Culex quinquefasciatus populations from northern Thailand and possible resistance mechanisms - Yanola_2015_Acta.Trop_149_232
Author(s) : Yanola J , Chamnanya S , Lumjuan N , Somboon P
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Abstract : Yanola_2015_Acta.Trop_149_232
ESTHER : Yanola_2015_Acta.Trop_149_232
PubMedSearch : Yanola_2015_Acta.Trop_149_232
PubMedID: 26091622

Title : Metabolic and Behavioral Mechanisms of Indoxacarb Resistance in Sitophilus zeamais (Coleoptera: Curculionidae) - Haddi_2015_J.Econ.Entomol_108_362
Author(s) : Haddi K , Mendonca LP , Dos Santos MF , Guedes RN , Oliveira EE
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Abstract : Haddi_2015_J.Econ.Entomol_108_362
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PubMedSearch : Haddi_2015_J.Econ.Entomol_108_362
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Title : Enzymes mediating resistance to lambda-cyhalothrin in Eriopis connexa (Coleoptera: Coccinellidae) - Rodrigues_2014_Pestic.Biochem.Physiol_110_36
Author(s) : Rodrigues AR , Siqueira HA , Torres JB
Ref : Pestic Biochem Physiol , 110 :36 , 2014
Abstract : Rodrigues_2014_Pestic.Biochem.Physiol_110_36
ESTHER : Rodrigues_2014_Pestic.Biochem.Physiol_110_36
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Title : Thiamethoxam resistance selected in the western flower thrips Frankliniella occidentalis (Thysanoptera: Thripidae): Cross-resistance patterns, possible biochemical mechanisms and fitness costs analysis - Gao_2014_Pestic.Biochem.Physiol_114_90
Author(s) : Gao CF , Ma SZ , Shan CH , Wu SF
Ref : Pestic Biochem Physiol , 114 :90 , 2014
Abstract : Gao_2014_Pestic.Biochem.Physiol_114_90
ESTHER : Gao_2014_Pestic.Biochem.Physiol_114_90
PubMedSearch : Gao_2014_Pestic.Biochem.Physiol_114_90
PubMedID: 25175655

Title : [Resistance mechanisms and cross-resistance of phoxim-resistant Frankliniella occidentalis Pergande population] - Wang_2012_Ying.Yong.Sheng.Tai.Xue.Bao_23_1933
Author(s) : Wang SY , Zhou XH , Zhang AS , Li LL , Men XY , Zhang SC , Liu YJ , Yu Y
Ref : Ying Yong Sheng Tai Xue Bao , 23 :1933 , 2012
Abstract : Wang_2012_Ying.Yong.Sheng.Tai.Xue.Bao_23_1933
ESTHER : Wang_2012_Ying.Yong.Sheng.Tai.Xue.Bao_23_1933
PubMedSearch : Wang_2012_Ying.Yong.Sheng.Tai.Xue.Bao_23_1933
PubMedID: 23173470

Title : Cross-resistance of bisultap resistant strain of Nilaparvata lugens and its biochemical mechanism - Ling_2011_J.Econ.Entomol_104_243
Author(s) : Ling S , Zhang R
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PubMedSearch : Ling_2011_J.Econ.Entomol_104_243
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Title : Cross-resistance study and biochemical mechanisms of thiamethoxam resistance in B-biotype Bemisia tabaci (Hemiptera: Aleyrodidae) - Feng_2010_Pest.Manag.Sci_66_313
Author(s) : Feng Y , Wu Q , Wang S , Chang X , Xie W , Xu B , Zhang Y
Ref : Pest Manag Sci , 66 :313 , 2010
Abstract : Feng_2010_Pest.Manag.Sci_66_313
ESTHER : Feng_2010_Pest.Manag.Sci_66_313
PubMedSearch : Feng_2010_Pest.Manag.Sci_66_313
PubMedID: 19937914

Title : Effects of spinosad on Helicoverpa armigera (Lepidoptera: Noctuidae) from China: tolerance status, synergism and enzymatic responses - Wang_2009_Pest.Manag.Sci_65_1040
Author(s) : Wang D , Qiu X , Ren X , Zhang W , Wang K
Ref : Pest Manag Sci , 65 :1040 , 2009
Abstract : Wang_2009_Pest.Manag.Sci_65_1040
ESTHER : Wang_2009_Pest.Manag.Sci_65_1040
PubMedSearch : Wang_2009_Pest.Manag.Sci_65_1040
PubMedID: 19533589

Title : Resistance selection and biochemical mechanism of resistance to two Acaricides in Tetranychus cinnabarinus (Boiduval) - Lin_2009_Pestic.Biochem.Physiol_93_47
Author(s) : Lin H , Chuan-hua X , Jin-jun W , Ming L , Wen-cai L , Zhi-mo Z
Ref : Pesticide Biochemistry and Physiology , 93 :47 , 2009
Abstract : Lin_2009_Pestic.Biochem.Physiol_93_47
ESTHER : Lin_2009_Pestic.Biochem.Physiol_93_47
PubMedSearch : Lin_2009_Pestic.Biochem.Physiol_93_47
PubMedID:

Title : Mechanisms of organophosphate resistance in a field population of oriental migratory locust, Locusta migratoria manilensis (Meyen) - Yang_2009_Arch.Insect.Biochem.Physiol_71_3
Author(s) : Yang ML , Zhang JZ , Zhu KY , Xuan T , Liu XJ , Guo YP , Ma EB
Ref : Archives of Insect Biochemistry & Physiology , 71 :3 , 2009
Abstract : Yang_2009_Arch.Insect.Biochem.Physiol_71_3
ESTHER : Yang_2009_Arch.Insect.Biochem.Physiol_71_3
PubMedSearch : Yang_2009_Arch.Insect.Biochem.Physiol_71_3
PubMedID: 18615705

Title : Inhibition of AChE by malathion and some structurally similar compounds - Krstic_2008_J.Enzyme.Inhib.Med.Chem_23_562
Author(s) : Krstic DZ , Colovic M , Kralj MB , Franko M , Krinulovic K , Trebse P , Vasic V
Ref : J Enzyme Inhib Med Chem , 23 :562 , 2008
Abstract : Krstic_2008_J.Enzyme.Inhib.Med.Chem_23_562
ESTHER : Krstic_2008_J.Enzyme.Inhib.Med.Chem_23_562
PubMedSearch : Krstic_2008_J.Enzyme.Inhib.Med.Chem_23_562
PubMedID: 18608787

Title : Inhibition of AChE by single and simultaneous exposure to malathion and its degradation products - Krstic_2007_Gen.Physiol.Biophys_26_247
Author(s) : Krstic D , Colovic M , Krinulovic K , Djuric D , Vasic V
Ref : Gen Physiol Biophys , 26 :247 , 2007
Abstract : Krstic_2007_Gen.Physiol.Biophys_26_247
ESTHER : Krstic_2007_Gen.Physiol.Biophys_26_247
PubMedSearch : Krstic_2007_Gen.Physiol.Biophys_26_247
PubMedID: 18281741

Title : Insecticide toxicity and synergism by enzyme inhibitors in 18 species of pest insect and natural enemies in crucifer vegetable crops - Wu_2007_Pest.Manag.Sci_63_500
Author(s) : Wu G , Miyata T , Kang CY , Xie LH
Ref : Pest Manag Sci , 63 :500 , 2007
Abstract : Wu_2007_Pest.Manag.Sci_63_500
ESTHER : Wu_2007_Pest.Manag.Sci_63_500
PubMedSearch : Wu_2007_Pest.Manag.Sci_63_500
PubMedID:

Title : Mediation of pyrethroid insecticide toxicity to honey bees (Hymenoptera: Apidae) by cytochrome P450 monooxygenases - Johnson_2006_J.Econ.Entomol_99_1046
Author(s) : Johnson RM , Wen Z , Schuler MA , Berenbaum MR
Ref : J Econ Entomol , 99 :1046 , 2006
Abstract : Johnson_2006_J.Econ.Entomol_99_1046
ESTHER : Johnson_2006_J.Econ.Entomol_99_1046
PubMedSearch : Johnson_2006_J.Econ.Entomol_99_1046
PubMedID: 16937654

Title : Parasitization by Cotesia plutellae enhances detoxifying enzyme activity in Plutella xylostella - Takeda_2006_Pestic.Biochem.Physiol_86_15
Author(s) : Takeda T , Nakamatsu Y , Tanaka T
Ref : Pesticide Biochemistry and Physiology , 86 :15 , 2006
Abstract : Takeda_2006_Pestic.Biochem.Physiol_86_15
ESTHER : Takeda_2006_Pestic.Biochem.Physiol_86_15
PubMedSearch : Takeda_2006_Pestic.Biochem.Physiol_86_15
PubMedID:

Title : Metabolic mechanisms of insecticide resistance in the western flower thrips, Frankliniella occidentalis (Pergande) - Espinosa_2005_Pest.Manag.Sci_61_1009
Author(s) : Espinosa PJ , Contreras J , Quinto V , Gravalos C , Fernandez E , Bielza P
Ref : Pest Manag Sci , 61 :1009 , 2005
Abstract : Espinosa_2005_Pest.Manag.Sci_61_1009
ESTHER : Espinosa_2005_Pest.Manag.Sci_61_1009
PubMedSearch : Espinosa_2005_Pest.Manag.Sci_61_1009
PubMedID: 15912569

Title : Susceptibilities to methamidophos and enzymatic characteristics in 18 species of pest insects and their natural enemies in crucifer vegetable crops - Wu_2005_Pestic.Biochem.Physiol_82_79
Author(s) : Wu G , Miyata T
Ref : Pesticide Biochemistry and Physiology , 82 :79 , 2005
Abstract : Wu_2005_Pestic.Biochem.Physiol_82_79
ESTHER : Wu_2005_Pestic.Biochem.Physiol_82_79
PubMedSearch : Wu_2005_Pestic.Biochem.Physiol_82_79
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Title : Chlorpyrifos resistance in mosquito Culex quinquefasciatus - Liu_2005_J.Med.Entomol_42_815
Author(s) : Liu H , Xu Q , Zhang L , Liu N
Ref : Journal of Medical Entomology , 42 :815 , 2005
Abstract : Liu_2005_J.Med.Entomol_42_815
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PubMedID: 16363165

Title : Activation of hepatic Nrf2 in vivo by acetaminophen in CD-1 mice - Goldring_2004_Hepatology_39_1267
Author(s) : Goldring CE , Kitteringham NR , Elsby R , Randle LE , Clement YN , Williams DP , McMahon M , Hayes JD , Itoh K , Yamamoto M , Park BK
Ref : Hepatology , 39 :1267 , 2004
Abstract : Goldring_2004_Hepatology_39_1267
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Title : Resistance to coumaphos and diazinon in Boophilus microplus (Acari: Ixodidae) and evidence for the involvement of an oxidative detoxification mechanism - Li_2003_J.Med.Entomol_40_482
Author(s) : Li AY , Davey RB , Miller RJ , George JE
Ref : Journal of Medical Entomology , 40 :482 , 2003
Abstract : Li_2003_J.Med.Entomol_40_482
ESTHER : Li_2003_J.Med.Entomol_40_482
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Title : Insecticide use and organophosphate resistance in the coffee leaf miner Leucoptera coffeella (Lepidoptera: Lyonetiidae) - Fragoso_2002_Bull.Entomol.Res_92_203
Author(s) : Fragoso DB , Guedes RN , Picanco MC , Zambolim L
Ref : Bull Entomol Res , 92 :203 , 2002
Abstract : Fragoso_2002_Bull.Entomol.Res_92_203
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Title : Evaluation of the developmental toxicity of thalidomide using frog embryo teratogenesis assay-xenopus (FETAX): biotransformation and detoxification - Fort_2000_Teratog.Carcinog.Mutagen_20_35
Author(s) : Fort DJ , Stover EL , Bantle JA , Finch RA
Ref : Teratog Carcinog Mutagen , 20 :35 , 2000
Abstract : Fort_2000_Teratog.Carcinog.Mutagen_20_35
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Title : Synergism of tebufenozide in resistant and susceptible strains of obliquebanded leafroller (Lepidoptera: Tortricidae) and resistance to new insecticides - Waldstein_2000_J.Econ.Entomol_93_1768
Author(s) : Waldstein DE , Reissig WH
Ref : J Econ Entomol , 93 :1768 , 2000
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PubMedSearch : Waldstein_2000_J.Econ.Entomol_93_1768
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Title : Characterization of malathion resistance in a Mexican population of Rhizopertha dominica - Guedes_1998_Pest.Sci_53_15
Author(s) : Guedes RNC , Zhu KY
Ref : Pest Sci , 53 :15 , 1998
Abstract : Guedes_1998_Pest.Sci_53_15
ESTHER : Guedes_1998_Pest.Sci_53_15
PubMedSearch : Guedes_1998_Pest.Sci_53_15
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Title : Toxicity of spinosad to susceptible and resistant strains of house flies, Musca domestica - Scott_1998_Pest.Sci_54_131
Author(s) : Scott JG
Ref : Pest Sci , 54 :131 , 1998
Abstract : Scott_1998_Pest.Sci_54_131
ESTHER : Scott_1998_Pest.Sci_54_131
PubMedSearch : Scott_1998_Pest.Sci_54_131
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Title : Effect of insecticide synergist combinations on the survival of Spodoptera exigua - Van Laecke_1993_Pest.Sci_37_283
Author(s) : Van Laecke K , Degheele D
Ref : Pest Sci , 37 :283 , 1993
Abstract : Van Laecke_1993_Pest.Sci_37_283
ESTHER : Van Laecke_1993_Pest.Sci_37_283
PubMedSearch : Van Laecke_1993_Pest.Sci_37_283
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Title : Differential toxicity of cocaine and its isomers, (+)-cocaine and (-)-psi-cocaine, is associated with stereoselective hydrolysis by hepatic carboxylesterases in cultured rat hepatocytes - Melchert_1992_Chem.Biol.Interact_84_243
Author(s) : Melchert RB , Goldlin C , Zweifel U , Welder AA , Boelsterli UA
Ref : Chemico-Biological Interactions , 84 :243 , 1992
Abstract : Melchert_1992_Chem.Biol.Interact_84_243
ESTHER : Melchert_1992_Chem.Biol.Interact_84_243
PubMedSearch : Melchert_1992_Chem.Biol.Interact_84_243
PubMedID: 1423743

Title : Synergism of organophosphorus insecticides by diethyl maleate and related compounds in house flies - Welling_1985_Pestic.Biochem.Physiol_23_358
Author(s) : Welling W , de Vries JW
Ref : Pesticide Biochemistry and Physiology , 23 :358 , 1985
Abstract : Welling_1985_Pestic.Biochem.Physiol_23_358
ESTHER : Welling_1985_Pestic.Biochem.Physiol_23_358
PubMedSearch : Welling_1985_Pestic.Biochem.Physiol_23_358
PubMedID:

Title : Parathion and methyl parathion toxicity and metabolism in piperonyl butoxide and diethyl maleate pretreated mice -
Author(s) : Mirer FE , Levine BS , Murphy SD
Ref : Chemico-Biological Interactions , 17 :99 , 1977
PubMedID: 872271