Indoxacarb
Indoxacarb acts against lepidopteran larvae. It has a role as a voltage-gated sodium channel blocker. In 2021, the European Union chose not to renew Indoxacarb for use as an insecticide. The United Kingdom still allows use of the compound until 2025
General
Type : Insecticide, Carboxamide, Carbamate, Trifluoro, Not AlphaBeta Hydrolase target
Chemical_Nomenclature : methyl (4aS)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
Canonical SMILES : COC(=O)C12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl
InChI : InChI=1S\/C22H17ClF3N3O7\/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26\/h3-9H,10-11H2,1-2H3\/t21-\/m0\/s1
InChIKey : VBCVPMMZEGZULK-NRFANRHFSA-N
Other name(s) : (S)-Indoxacarb || Steward || Provaunt || Advion || Avaunt || CHEBI:38630 || SCHEMBL22073 || CHEMBL197676 || ZINC28527855 || (+-)-Indoxacarb || (+\/-)-Indoxacarb || (R)-Indoxacarb || Indoxacarb, (-)-
MW : 527.8
Formula : C22H17ClF3N3O7
CAS_number : 173584-44-6, 144171-61-9, 185608-75-7
PubChem : 107720, 9936739, 18772464
UniChem : VBCVPMMZEGZULK-NRFANRHFSA-N
Wikipedia : Indoxacarb
Target
Structures : No structure
Families : Carb_B_Arthropoda
References (18)
| Title : Low concentration of indoxacarb interferes with the growth and development of silkworm by damaging the structure of midgut cells - Wang_2023_Pestic.Biochem.Physiol_195_105567 |
| Author(s) : Wang W , Su Y , Liu X , Qi R , Li F , Li B , Sun H |
| Ref : Pestic Biochem Physiol , 195 :105567 , 2023 |
| Abstract : |
| PubMedSearch : Wang_2023_Pestic.Biochem.Physiol_195_105567 |
| PubMedID: 37666598 |
| Title : Inducible Gut-Specific Carboxylesterase SlCOE030 in Polyphagous Pests of Spodoptera litura Conferring Tolerance between Nicotine and Cyantraniliprole - Li_2023_J.Agric.Food.Chem__ |
| Author(s) : Li J , Lv Y , Liu Y , Bi R , Pan Y , Shang Q |
| Ref : Journal of Agricultural and Food Chemistry , : , 2023 |
| Abstract : |
| PubMedSearch : Li_2023_J.Agric.Food.Chem__ |
| PubMedID: 36877657 |
| Gene_locus related to this paper: spolt-SlCOE030 |
| Title : Contribution of multiple overexpressed carboxylesterase genes to indoxacarb resistance in Spodoptera litura - Shi_2022_Pest.Manag.Sci__ |
| Author(s) : Shi Y , Li W , Zhou Y , Liao X , Shi L |
| Ref : Pest Manag Sci , : , 2022 |
| Abstract : |
| PubMedSearch : Shi_2022_Pest.Manag.Sci__ |
| PubMedID: 35066991 |
| Title : Comprehensive Detoxification Mechanism Assessment of Red Imported Fire Ant (Solenopsis invicta) against Indoxacarb - Siddiqui_2022_Molecules_27_ |
| Author(s) : Siddiqui JA , Zhang Y , Luo Y , Bamisile BS , Rehman NU , Islam W , Qasim M , Jiang Q , Xu Y |
| Ref : Molecules , 27 : , 2022 |
| Abstract : |
| PubMedSearch : Siddiqui_2022_Molecules_27_ |
| PubMedID: 35164134 |
| Title : Mechanisms of Increased Indoxacarb Toxicity in Methoxyfenozide-Resistant Cotton Bollworm Helicoverpa armigera (Lepidoptera: Noctuidae) - Wang_2020_Toxics_8_ |
| Author(s) : Wang Q , Rui C , Wang L , Li F , Nahiyoon SA , Yuan H , Cui L |
| Ref : Toxics , 8 : , 2020 |
| Abstract : |
| PubMedSearch : Wang_2020_Toxics_8_ |
| PubMedID: 32957560 |
| Title : Purification and characterization of a thermoalkaliphilic esterase from Bacillus cereus WZZ006 for enantioselective resolution of indoxacarb intermediate - Zhang_2019_Int.J.Biol.Macromol_140_358 |
| Author(s) : Zhang H , Xia Y , Zhou M , Zheng J , Wang Z , Zhang Y |
| Ref : Int J Biol Macromol , 140 :358 , 2019 |
| Abstract : |
| PubMedSearch : Zhang_2019_Int.J.Biol.Macromol_140_358 |
| PubMedID: 31430490 |
| Title : A systemic study of indoxacarb resistance in Spodoptera litura revealed complex expression profiles and regulatory mechanism - Shi_2019_Sci.Rep_9_14997 |
| Author(s) : Shi L , Shi Y , Zhang Y , Liao X |
| Ref : Sci Rep , 9 :14997 , 2019 |
| Abstract : |
| PubMedSearch : Shi_2019_Sci.Rep_9_14997 |
| PubMedID: 31628365 |
| Title : Identification and detection of indoxacarb resistance mutations in the para sodium channel of the tomato leafminer, Tuta absoluta - Roditakis_2017_Pest.Manag.Sci_73_1679 |
| Author(s) : Roditakis E , Mavridis K , Riga M , Vasakis E , Morou E , Rison JL , Vontas J |
| Ref : Pest Manag Sci , 73 :1679 , 2017 |
| Abstract : |
| PubMedSearch : Roditakis_2017_Pest.Manag.Sci_73_1679 |
| PubMedID: 28019074 |
| Title : Detection of carboxylesterase and esterase activity in culturable gut bacterial flora isolated from diamondback moth, Plutella xylostella (Linnaeus), from India and its possible role in indoxacarb degradation - Ramya_2016_Braz.J.Microbiol_47_327 |
| Author(s) : Ramya SL , Venkatesan T , Srinivasa Murthy K , Jalali SK , Verghese A |
| Ref : Braz J Microbiol , 47 :327 , 2016 |
| Abstract : |
| PubMedSearch : Ramya_2016_Braz.J.Microbiol_47_327 |
| PubMedID: 26991291 |
| 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 |
| Ref : J Econ Entomol , 108 :362 , 2015 |
| Abstract : |
| PubMedSearch : Haddi_2015_J.Econ.Entomol_108_362 |
| PubMedID: 26470140 |
| Title : Determination of baseline susceptibility of European populations of Tuta absoluta (Meyrick) to indoxacarb and chlorantraniliprole using a novel dip bioassay method - Roditakis_2013_Pest.Manag.Sci_69_217 |
| Author(s) : Roditakis E , Skarmoutsou C , Staurakaki M , Martinez-Aguirre Mdel R , Garcia-Vidal L , Bielza P , Haddi K , Rapisarda C , Rison JL , Bassi A , Teixeira LA |
| Ref : Pest Manag Sci , 69 :217 , 2013 |
| Abstract : |
| PubMedSearch : Roditakis_2013_Pest.Manag.Sci_69_217 |
| PubMedID: 23034903 |
| Title : Biochemical analysis and synergistic suppression of indoxacarb resistance in Plutella xylostella L. - Nehare_2010_J.Asia.Pac.Entomol_13_91 |
| Author(s) : Nehare S , Moharil MP , Ghodki BS , Lande GK , Bisane KD , Thakare AS , Barkhade UP |
| Ref : Journal of Asia-Pacific Entomology , 13 :91 , 2010 |
| Abstract : |
| PubMedSearch : Nehare_2010_J.Asia.Pac.Entomol_13_91 |
| PubMedID: |
| Title : Effects of the synergist S,S,S-tributyl phosphorotrithioate on indoxacarb toxicity and metabolism in the European corn borer, Ostrinia nubilalis (Hubner) - Alves_2008_Pestic.Biochem.Physiol_90_26 |
| Author(s) : Alves AP , Allgeier WJ , Siegfried BD |
| Ref : Pesticide Biochemistry and Physiology , 90 :26 , 2008 |
| Abstract : |
| PubMedSearch : Alves_2008_Pestic.Biochem.Physiol_90_26 |
| PubMedID: |
| Title : Evaluation of indoxacarb, an oxadiazine insecticide for the control of pyrethroid-resistant Anopheles gambiae (Diptera: Culicidae) - N'Guessan_2007_J.Med.Entomol_44_270 |
| Author(s) : N'Guessan R , Corbel V , Bonnet J , Yates A , Asidi A , Boko P , Odjo A , Akogbeto M , Rowland M |
| Ref : Journal of Medical Entomology , 44 :270 , 2007 |
| Abstract : |
| PubMedSearch : N'Guessan_2007_J.Med.Entomol_44_270 |
| PubMedID: 17427696 |
| Title : The effect of indoxacarb and five other insecticides on Phytoseiulus persimilis (Acari: Phytoseiidae), Amblyseius fallacis (Acari: Phytoseiidae) and nymphs of Orius insidiosus (Hemiptera: Anthocoridae) - Bostanian_2006_Pest.Manag.Sci_62_334 |
| Author(s) : Bostanian NJ , Akalach M |
| Ref : Pest Manag Sci , 62 :334 , 2006 |
| Abstract : |
| PubMedSearch : Bostanian_2006_Pest.Manag.Sci_62_334 |
| PubMedID: 16493722 |
| Title : The contact toxicity of indoxacarb and five other insecticides to Orius insidiosus (Hemiptera: Anthocoridae) and Aphidius colemani (Hymenoptera: Braconidae), beneficials used in the greenhouse industry - Bostanian_2004_Pest.Manag.Sci_60_1231 |
| Author(s) : Bostanian NJ , Akalach M |
| Ref : Pest Manag Sci , 60 :1231 , 2004 |
| Abstract : |
| PubMedSearch : Bostanian_2004_Pest.Manag.Sci_60_1231 |
| PubMedID: 15578604 |
| Title : Indoxacarb, an oxadiazine insecticide, blocks insect neuronal sodium channels - Lapied_2001_Br.J.Pharmacol_132_587 |
| Author(s) : Lapied B , Grolleau F , Sattelle DB |
| Ref : British Journal of Pharmacology , 132 :587 , 2001 |
| Abstract : |
| PubMedSearch : Lapied_2001_Br.J.Pharmacol_132_587 |
| PubMedID: 11159709 |
| Title : The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides - McCann_2001_Pest.Manag.Sci_57_153 |
| Author(s) : McCann SF , Annis GD , Shapiro R , Piotrowski DW , Lahm GP , Long JK , Lee KC , Hughes MM , Myers BJ , Griswold SM , Reeves BM , March RW , Sharpe PL , Lowder P , Barnette WE , Wing KD |
| Ref : Pest Manag Sci , 57 :153 , 2001 |
| Abstract : |
| PubMedSearch : McCann_2001_Pest.Manag.Sci_57_153 |
| PubMedID: 11455646 |