Fenvalerate
Fenvalerate is an insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha (or SS) configuration is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.
General
Type : Pyrethroid, Phenoxyphenyl
Chemical_Nomenclature : [cyano-(3-phenoxyphenyl)methyl] 2-(4-chlorophenyl)-3-methylbutanoate
Canonical SMILES : CC(C)C(C1=CC=C(C=C1)Cl)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
InChI : InChI=1S\/C25H22ClNO3\/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21\/h3-15,17,23-24H,1-2H3
InChIKey : NYPJDWWKZLNGGM-UHFFFAOYSA-N
Other name(s) : Pydrin || Phenvalerate || Sumicidin || CHEBI:5014 || SCHEMBL26911 || CHEMBL492491 || Belmark || Tirade || Aqmatrine || Phenoxin || Agrofen || Ectrin || Fenaxin || Fenkem || Fenkill || Fenoxin || Fenval || Furitrothion || Insectral || Sanmarton || Sumibac || Sumifleece || Sumifly || Sumipower || Sumitick || Sumkidin || Tribute
MW : 419.9
Formula : C25H22ClNO3
CAS_number : 51630-58-1
PubChem : 3347
UniChem : NYPJDWWKZLNGGM-UHFFFAOYSA-N
Target
Structures : No structure
Families : Carb_B_Arthropoda, Carb_B_Chordata, HNLyase_Bact
References (23)
| Title : Heterologous expression, biochemical characterization and prospects for insecticide biosensing potential of carboxylesterase Ha006a from Helicoverpa armigera - Kaur_2024_Pestic.Biochem.Physiol_200_105844 |
| Author(s) : Kaur H , Rode S , Lonare S , Demiwal P , Narasimhappa P , Arun E , Kumar R , Das J , Ramamurthy PC , Sircar D , Sharma AK |
| Ref : Pestic Biochem Physiol , 200 :105844 , 2024 |
| Abstract : |
| PubMedSearch : Kaur_2024_Pestic.Biochem.Physiol_200_105844 |
| PubMedID: 38582571 |
| Gene_locus related to this paper: helam-d5g3e0 |
| Title : SlCarE054 in Spodoptera litura (Lepidoptera: Noctuidae) showed direct metabolic activity to beta-cypermethrin with stereoselectivity - Xu_2024_Bull.Entomol.Res__1 |
| Author(s) : Xu L , Liu H , Li B , Li G , Liu R , Li D |
| Ref : Bull Entomol Res , :1 , 2024 |
| Abstract : |
| PubMedSearch : Xu_2024_Bull.Entomol.Res__1 |
| PubMedID: 38708572 |
| Gene_locus related to this paper: spolt-SlCarE054 |
| Title : Overexpression of PxalphaE14 Contributing to Detoxification of Multiple Insecticides in Plutella xylostella (L.) - Li_2022_J.Agric.Food.Chem_70_5794 |
| Author(s) : Li R , Zhu B , Hu XP , Shi XY , Qi LL , Liang P , Gao XW |
| Ref : Journal of Agricultural and Food Chemistry , 70 :5794 , 2022 |
| Abstract : |
| PubMedSearch : Li_2022_J.Agric.Food.Chem_70_5794 |
| PubMedID: 35510781 |
| Gene_locus related to this paper: pluxy-PxalphaE14 |
| Title : Two single mutations in carboxylesterase 001C improve fenvalerate hydrolase activity in Helicoverpa armigera - Xu_2021_Pestic.Biochem.Physiol_179_104969 |
| Author(s) : Xu JJ , Chang YM , Lu M , Tie Y , Dong YL , Chen GY , Ma ZQ , Liu XL , Li YQ |
| Ref : Pestic Biochem Physiol , 179 :104969 , 2021 |
| Abstract : |
| PubMedSearch : Xu_2021_Pestic.Biochem.Physiol_179_104969 |
| PubMedID: 34802519 |
| Gene_locus related to this paper: helam-d5kx87 |
| Title : Pyrethroid Carboxylesterase PytH from Sphingobium faniae JZ-2: Structure and Catalytic Mechanism - Xu_2020_Appl.Environ.Microbiol_86_e02971 |
| Author(s) : Xu D , Gao Y , Sun B , Ran T , Zeng L , He J , Wang W |
| Ref : Applied Environmental Microbiology , 86 :e02971 , 2020 |
| Abstract : |
| PubMedSearch : Xu_2020_Appl.Environ.Microbiol_86_e02971 |
| PubMedID: 32303545 |
| Gene_locus related to this paper: sphwj-c0la90 |
| Title : Metabolism of bifenthrin, beta-cyfluthrin, -cyhalothrin, cyphenothrin and esfenvalerate by rat and human cytochrome P450 and carboxylesterase enzymes - Hedges_2020_Xenobiotica__1 |
| Author(s) : Hedges L , Brown S , MacLeod AK , Moreau M , Yoon M , Creek MR , Osimitz TG , Lake BG |
| Ref : Xenobiotica , :1 , 2020 |
| Abstract : |
| PubMedSearch : Hedges_2020_Xenobiotica__1 |
| PubMedID: 32672501 |
| Title : Development and Application of a Life-Stage Physiologically Based Pharmacokinetic (PBPK) Model to the Assessment of Internal Dose of Pyrethroids in Humans - Mallick_2020_Toxicol.Sci_173_86 |
| Author(s) : Mallick P , Moreau M , Song G , Efremenko AY , Pendse SN , Creek MR , Osimitz TG , Hines RN , Hinderliter P , Clewell HJ , Lake BG , Yoon M |
| Ref : Toxicol Sci , 173 :86 , 2020 |
| Abstract : |
| PubMedSearch : Mallick_2020_Toxicol.Sci_173_86 |
| PubMedID: 31593217 |
| Title : Identification and biochemical characterization of carboxylesterase 001G associated with insecticide detoxification in Helicoverpa armigera - Bai_2019_Pestic.Biochem.Physiol_157_69 |
| Author(s) : Bai LS , Zhao CX , Xu JJ , Feng C , Li YQ , Dong YL , Ma ZQ |
| Ref : Pestic Biochem Physiol , 157 :69 , 2019 |
| Abstract : |
| PubMedSearch : Bai_2019_Pestic.Biochem.Physiol_157_69 |
| PubMedID: 31153479 |
| Gene_locus related to this paper: helam-d5g3d4 |
| Title : Bacterial Expression and Kinetic Analysis of Carboxylesterase 001D from Helicoverpa armigera - Li_2016_Int.J.Mol.Sci_17_ |
| Author(s) : Li Y , Liu J , Lu M , Ma Z , Cai C , Wang Y , Zhang X |
| Ref : Int J Mol Sci , 17 : , 2016 |
| Abstract : |
| PubMedSearch : Li_2016_Int.J.Mol.Sci_17_ |
| PubMedID: 27049381 |
| Gene_locus related to this paper: helam-d5kxa9 |
| Title : Sub-lethal toxicity of environmentally relevant concentrations of esfenvalerate to Chironomus riparius - Rodrigues_2015_Environ.Pollut_207_273 |
| Author(s) : Rodrigues AC , Gravato C , Quintaneiro C , Barata C , Soares AM , Pestana JL |
| Ref : Environ Pollut , 207 :273 , 2015 |
| Abstract : |
| PubMedSearch : Rodrigues_2015_Environ.Pollut_207_273 |
| PubMedID: 26412267 |
| Title : Organophosphate and pyrethroid hydrolase activities of mutant Esterases from the cotton bollworm Helicoverpa armigera - Li_2013_PLoS.One_8_e77685 |
| Author(s) : Li Y , Farnsworth CA , Coppin CW , Teese MG , Liu JW , Scott C , Zhang X , Russell RJ , Oakeshott JG |
| Ref : PLoS ONE , 8 :e77685 , 2013 |
| Abstract : |
| PubMedSearch : Li_2013_PLoS.One_8_e77685 |
| PubMedID: 24204917 |
| Gene_locus related to this paper: helam-d5g3c9 , helam-d5g3d2 , helam-d5g3d3 , helam-d5g3d4 , helam-d5g3d5 , helam-d5kx87 , helam-d5kx99 , helam-d5kxa9 , helam-d9iv61 , helam-d9iv62 , helam-h9zvh4 , helam-s4wfz6 |
| Title : Overexpressed esterases in a fenvalerate resistant strain of the cotton bollworm, Helicoverpa armigera - Wu_2011_Insect.Biochem.Mol.Biol_41_14 |
| Author(s) : Wu S , Yang Y , Yuan G , Campbell PM , Teese MG , Russell RJ , Oakeshott JG , Wu Y |
| Ref : Insect Biochemistry & Molecular Biology , 41 :14 , 2011 |
| Abstract : |
| PubMedSearch : Wu_2011_Insect.Biochem.Mol.Biol_41_14 |
| PubMedID: 20875855 |
| Gene_locus related to this paper: helam-h9zvh4 |
| Title : Cloning of a novel pyrethroid-hydrolyzing carboxylesterase gene from Sphingobium sp. strain JZ-1 and characterization of the gene product - Wang_2009_Appl.Environ.Microbiol_75_5496 |
| Author(s) : Wang BZ , Guo P , Hang BJ , Li L , He J , Li SP |
| Ref : Applied Environmental Microbiology , 75 :5496 , 2009 |
| Abstract : |
| PubMedSearch : Wang_2009_Appl.Environ.Microbiol_75_5496 |
| PubMedID: 19581484 |
| Gene_locus related to this paper: sphwj-c0la90 |
| Title : Potentiation between pyrethroid and organophosphate insecticides in resistant field populations of cotton bollworm Helicoverpa armigera (Lepidoptera: Noctuidae) in Pakistan - Ahmad_2008_Pestic.Biochem.Physiol_91_24 |
| Author(s) : Ahmad M |
| Ref : Pesticide Biochemistry and Physiology , 91 :24 , 2008 |
| Abstract : |
| PubMedSearch : Ahmad_2008_Pestic.Biochem.Physiol_91_24 |
| PubMedID: |
| Title : Hydrolysis of individual isomers of fluorogenic pyrethroid analogs by mutant carboxylesterases from Lucilia cuprina - Devonshire_2007_Insect.Biochem.Mol.Biol_37_891 |
| Author(s) : Devonshire AL , Heidari R , Huang HZ , Hammock BD , Russell RJ , Oakeshott JG |
| Ref : Insect Biochemistry & Molecular Biology , 37 :891 , 2007 |
| Abstract : |
| PubMedSearch : Devonshire_2007_Insect.Biochem.Mol.Biol_37_891 |
| PubMedID: 17681228 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Species differences in the in vitro metabolism of deltamethrin and esfenvalerate: differential oxidative and hydrolytic metabolism by humans and rats - Godin_2006_Drug.Metab.Dispos_34_1764 |
| Author(s) : Godin SJ , Scollon EJ , Hughes MF , Potter PM , DeVito MJ , Ross MK |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 34 :1764 , 2006 |
| Abstract : |
| PubMedSearch : Godin_2006_Drug.Metab.Dispos_34_1764 |
| PubMedID: 16855054 |
| Title : Individual variability in esterase activity and CYP1A levels in Chinook salmon (Oncorhynchus tshawytscha) exposed to esfenvalerate and chlorpyrifos - Wheelock_2005_Aquat.Toxicol_74_172 |
| Author(s) : Wheelock CE , Eder KJ , Werner I , Huang H , Jones PD , Brammell BF , Elskus AA , Hammock BD |
| Ref : Aquat Toxicol , 74 :172 , 2005 |
| Abstract : |
| PubMedSearch : Wheelock_2005_Aquat.Toxicol_74_172 |
| PubMedID: 16011852 |
| Title : Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes - Stok_2004_J.Biol.Chem_279_29863 |
| Author(s) : Stok JE , Huang H , Jones PD , Wheelock CE , Morisseau C , Hammock BD |
| Ref : Journal of Biological Chemistry , 279 :29863 , 2004 |
| Abstract : |
| PubMedSearch : Stok_2004_J.Biol.Chem_279_29863 |
| PubMedID: 15123619 |
| Gene_locus related to this paper: mouse-Ces2a , mouse-Ces2e |
| Title : Molecular and cellular biomarker responses to pesticide exposure in juvenile chinook salmon (Oncorhynchus tshawytscha) - Eder_2004_Mar.Environ.Res_58_809 |
| Author(s) : Eder KJ , Leutenegger CM , Wilson BW , Werner I |
| Ref : Mar Environ Research , 58 :809 , 2004 |
| Abstract : |
| PubMedSearch : Eder_2004_Mar.Environ.Res_58_809 |
| PubMedID: 15178118 |
| Title : Joint acute toxicity of esfenvalerate and diazinon to larval fathead minnows (Pimephales promelas) - Denton_2003_Environ.Toxicol.Chem_22_336 |
| Author(s) : Denton DL , Wheelock CE , Murray SA , Deanovic LA , Hammock BD , Hinton DE |
| Ref : Environ Toxicol Chem , 22 :336 , 2003 |
| Abstract : |
| PubMedSearch : Denton_2003_Environ.Toxicol.Chem_22_336 |
| PubMedID: 12558165 |
| Title : Esterases and Fenvalerate Resistance in a Field Population of Helicoverpa punctigera (Lepidoptera: Noctuidae) in Australia - Gunning_1997_Pestic.Biochem.Physiol_58_155 |
| Author(s) : Gunning RV , Moores GD , Devonshire AL |
| Ref : Pesticide Biochemistry and Physiology , 58 :155 , 1997 |
| Abstract : |
| PubMedSearch : Gunning_1997_Pestic.Biochem.Physiol_58_155 |
| PubMedID: |
| Title : Esterases and Esfenvalerate Resistance in Australian Helicoverpa armigera(Hubner) Lepidoptera:Noctuidae - Gunning_1996_Pestic.Biochem.Physiol_54_12 |
| Author(s) : Gunning RV , Moores GD , Devonshire AL |
| Ref : Pesticide Biochemistry and Physiology , 54 :12 , 1996 |
| Abstract : |
| PubMedSearch : Gunning_1996_Pestic.Biochem.Physiol_54_12 |
| PubMedID: |
| Title : Hydrolysis of pyrethroid insecticides by soluble mouse brain esterases - Ghiasuddin_1984_Toxicol.Appl.Pharmacol_74_390 |
| Author(s) : Ghiasuddin SM , Soderlund DM |
| Ref : Toxicol Appl Pharmacol , 74 :390 , 1984 |
| Abstract : |
| PubMedSearch : Ghiasuddin_1984_Toxicol.Appl.Pharmacol_74_390 |
| PubMedID: 6740686 |