Thiamethoxam
Thiamethoxam is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Neonicotinoids, like nicotine, bind to nicotinic acetylcholine receptors
General
Type : Insecticide, Neonicotinoid, Thiazole, Sulfur Compound, Not AlphaBeta Hydrolase target, Derivative of Nicotine, Nicotinic agonist
Chemical_Nomenclature : (NE)-N-[3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene]nitramide
Canonical SMILES : CN\\1COCN(\/C1=N\/[N+](=O)[O-])CC2=CN=C(S2)Cl
InChI : InChI=1S\/C8H10ClN5O3S\/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6\/h2H,3-5H2,1H3\/b11-8+
InChIKey : NWWZPOKUUAIXIW-DHZHZOJOSA-N
Other name(s) : Actara || Cruiser || Diacloden || Adage || CHEBI:39185 || RefChem:389311 || CGA 293343 || SCHEMBL22916 || CHEBI:39186
MW : 291.72
Formula : C8H10ClN5O3S
CAS_number : 153719-23-4
PubChem : 5821911
UniChem : NWWZPOKUUAIXIW-DHZHZOJOSA-N
Target
Structures : No structure
Families : Carb_B_Arthropoda
References (38)
| Title : Life-stage-specific resistance to imidacloprid and thiamethoxam in COI-confirmed Bemisia tabaci MEAM1 and adult detoxification enzyme activity - Mohammad_2026_Sci.Rep__ |
| Author(s) : Mohammad Nejad Havestin M , Sabahi Q , Amiri A , Sheikhi Garjan A , Bandani AR |
| Ref : Sci Rep , : , 2026 |
| Abstract : |
| PubMedSearch : Mohammad_2026_Sci.Rep__ |
| PubMedID: 42086709 |
| Title : Demographic, physiological, and transcriptomic responses of Fopius arisanus to sublethal beta-cypermethrin and thiamethoxam - Lin_2026_Pest.Manag.Sci__ |
| Author(s) : Lin J , Ding W , Liang Y , Yue G , Chen J , Song Y , Li Y , Ji Q , Lu Y |
| Ref : Pest Manag Sci , : , 2026 |
| Abstract : |
| PubMedSearch : Lin_2026_Pest.Manag.Sci__ |
| PubMedID: 41786339 |
| Title : Comparative Transcriptomic Analysis of Detoxification Enzyme Gene Families in Parent and Offspring Riptortus pedestris After Sublethal Thiamethoxam Treatment - Zhao_2026_Insects_17_ |
| Author(s) : Zhao S , Wang Z , Chen S , Li R , Du Z , Huang X , Yuan H , Shi S , Zhou Y , Gao Y |
| Ref : Insects , 17 : , 2026 |
| Abstract : |
| PubMedSearch : Zhao_2026_Insects_17_ |
| PubMedID: 42355381 |
| Title : In Vitro Evidence of Thiamethoxam Toxicity in Tubifex tubifex: Implications for Aquatic Risk Assessment - Mandal_2026_J.Appl.Toxicol__ |
| Author(s) : Mandal AH , Ghosh S , Sadhu A , Saha NC , Saha S |
| Ref : J Appl Toxicol , : , 2026 |
| Abstract : |
| PubMedSearch : Mandal_2026_J.Appl.Toxicol__ |
| PubMedID: 42517655 |
| Title : Systemic Assessment of Chronic Toxicity of Thiamethoxam on Honeybees (Apis mellifera) - Li_2025_Insects_16_936 |
| Author(s) : Li MJ , He QB , Wu YF , Gao Q , Wang AL , Xiao JJ , Liao M , Huang Y , Wang YH , Cao HQ |
| Ref : Insects , 16 :936 , 2025 |
| Abstract : |
| PubMedSearch : Li_2025_Insects_16_936 |
| PubMedID: 41009116 |
| Title : Acute toxicity and sublethal effects of thiamethoxam on the stingless bee Scaptotrigona postica: Survival, neural morphology, and enzymatic responses - Maloni_2025_Environ.Pollut_369_125864 |
| Author(s) : Maloni G , Miotelo L , Otero IVR , Souza FC , Nocelli RCF , Malaspina O |
| Ref : Environ Pollut , 369 :125864 , 2025 |
| Abstract : |
| PubMedSearch : Maloni_2025_Environ.Pollut_369_125864 |
| PubMedID: 39954757 |
| Title : Thiamethoxam toxicity on the stingless bee Friesiomelitta varia: LC(50), survival time, and enzymatic biomarkers assessment - de Souza_2024_Chemosphere_363_142853 |
| Author(s) : de Souza FC , Miotelo L , Maloni G , Otero IVR , Nocelli RCF , Malaspina O |
| Ref : Chemosphere , 363 :142853 , 2024 |
| Abstract : |
| PubMedSearch : de Souza_2024_Chemosphere_363_142853 |
| PubMedID: 39019173 |
| Title : The protective role of L-carnitine on oxidative stress, neurotransmitter perturbations, astrogliosis, and apoptosis induced by thiamethoxam in the brains of male rats - Abd_2023_Naunyn.Schmiedebergs.Arch.Pharmacol__ |
| Author(s) : Abd Elkader HAE , Hussein MM , Mohammed NA , Abdou HM |
| Ref : Naunyn Schmiedebergs Arch Pharmacol , : , 2023 |
| Abstract : |
| PubMedSearch : Abd_2023_Naunyn.Schmiedebergs.Arch.Pharmacol__ |
| PubMedID: 38099937 |
| Title : Transcriptomic investigation of the molecular mechanisms underlying resistance to the neonicotinoid thiamethoxam and the pyrethroid lambda-cyhalothrin in Euschistus heros (Hemiptera: Pentatomidae) - Lira_2023_Pest.Manag.Sci__ |
| Author(s) : Lira EC , Nascimento ARB , Bass C , Omoto C , Consoli FL |
| Ref : Pest Manag Sci , : , 2023 |
| Abstract : |
| PubMedSearch : Lira_2023_Pest.Manag.Sci__ |
| PubMedID: 37624650 |
| Title : Multibiomarker responses after exposure to a sublethal concentration of thiamethoxam in the African honeybee (Apis mellifera intermissa) - Benchaabane_2022_Comp.Biochem.Physiol.C.Toxicol.Pharmacol_257_109334 |
| Author(s) : Benchaabane S , Ayad AS , Loucif-Ayad W , Soltani N |
| Ref : Comparative Biochemistry & Physiology C Toxicol Pharmacol , 257 :109334 , 2022 |
| Abstract : |
| PubMedSearch : Benchaabane_2022_Comp.Biochem.Physiol.C.Toxicol.Pharmacol_257_109334 |
| PubMedID: 35351619 |
| Title : Antioxidant enzyme activity and pathophysiological responses in the freshwater walking catfish, Clarias batrachus Linn under sub-chronic and chronic exposures to the neonicotinoid, Thiamethoxam - Mukherjee_2022_Sci.Total.Environ__155716 |
| Author(s) : Mukherjee D , Saha S , Chukwuka AV , Ghosh B , Dhara K , Saha NC , Pal P , Faggio C |
| Ref : Sci Total Environ , :155716 , 2022 |
| Abstract : |
| PubMedSearch : Mukherjee_2022_Sci.Total.Environ__155716 |
| PubMedID: 35526629 |
| Title : Acute thiamethoxam exposure induces hepatotoxicity and neurotoxicity in juvenile Chinese mitten crab (Eriocheir sinensis) - Yang_2022_Ecotoxicol.Environ.Saf_249_114399 |
| Author(s) : Yang Y , Yu Q , Zhang C , Wang X , He L , Huang Y , Li E , Qin J , Chen L |
| Ref : Ecotoxicology & Environmental Safety , 249 :114399 , 2022 |
| Abstract : |
| PubMedSearch : Yang_2022_Ecotoxicol.Environ.Saf_249_114399 |
| PubMedID: 36508784 |
| Title : Effect of thiamethoxam on the behavioral profile alteration and toxicity of adult zebrafish at environmentally relevant concentrations - Yang_2022_Sci.Total.Environ_858_159883 |
| Author(s) : Yang J , Guo C , Luo Y , Fan J , Wang W , Yin X , Xu J |
| Ref : Sci Total Environ , 858 :159883 , 2022 |
| Abstract : |
| PubMedSearch : Yang_2022_Sci.Total.Environ_858_159883 |
| PubMedID: 36356732 |
| Title : Sublethal Effects of Thiamethoxam on Biological Traits and Detoxification Enzyme Activities in the Small Brown Planthopper, Laodelphax striatellus (Falln) - Cai_2022_J.Econ.Entomol__ |
| Author(s) : Cai Y , Dou T , Gao F , Wang G , Dong Y , Song N , An S , Yin X , Liu X , Ren Y |
| Ref : J Econ Entomol , : , 2022 |
| Abstract : |
| PubMedSearch : Cai_2022_J.Econ.Entomol__ |
| PubMedID: 36351784 |
| Title : Imidacloprid and thiamethoxam affect synaptic transmission in zebrafish - Zhang_2021_Ecotoxicol.Environ.Saf_227_112917 |
| Author(s) : Zhang JG , Ma DD , Xiong Q , Qiu SQ , Huang GY , Shi WJ , Ying GG |
| Ref : Ecotoxicology & Environmental Safety , 227 :112917 , 2021 |
| Abstract : |
| PubMedSearch : Zhang_2021_Ecotoxicol.Environ.Saf_227_112917 |
| PubMedID: 34678628 |
| Title : Enzymatic responses in the head and midgut of Africanized Apis mellifera contaminated with a sublethal concentration of thiamethoxam - Decio_2021_Ecotoxicol.Environ.Saf_223_112581 |
| Author(s) : Decio P , Miotelo L , Pereira FDC , Roat TC , Marin-Morales MA , Malaspina O |
| Ref : Ecotoxicology & Environmental Safety , 223 :112581 , 2021 |
| Abstract : |
| PubMedSearch : Decio_2021_Ecotoxicol.Environ.Saf_223_112581 |
| PubMedID: 34352576 |
| Title : Acute Toxicity of Insecticide Thiamethoxam to Crayfish (Astacus leptodactylus): Alterations in Oxidative Stress Markers, ATPases and Cholinesterase - Uckun_2021_Acta.Chim.Slov_68_521 |
| Author(s) : Uckun M , Yolo Lu E , Uckun AA , Oz O BM |
| Ref : Acta Chim Slov , 68 :521 , 2021 |
| Abstract : |
| PubMedSearch : Uckun_2021_Acta.Chim.Slov_68_521 |
| PubMedID: 34897546 |
| Title : Symbiotic Fungus Affected the Asian Citrus Psyllid (ACP) Resistance to Imidacloprid and Thiamethoxam - Yi_2020_Front.Microbiol_11_522164 |
| Author(s) : Yi T , Lei L , He L , Yi J , Li L , Dai L , Hong Y |
| Ref : Front Microbiol , 11 :522164 , 2020 |
| Abstract : |
| PubMedSearch : Yi_2020_Front.Microbiol_11_522164 |
| PubMedID: 33391190 |
| Title : Cross-resistance and Fitness Cost Analysis of Resistance to Thiamethoxam in Melon and Cotton Aphid (Hemiptera: Aphididae) - Zhang_2020_J.Econ.Entomol__ |
| Author(s) : Zhang H , Chen A , Shan T , Dong W , Shi X , Gao X |
| Ref : J Econ Entomol , : , 2020 |
| Abstract : |
| PubMedSearch : Zhang_2020_J.Econ.Entomol__ |
| PubMedID: 32372079 |
| Title : Chronic exposure to imidacloprid or thiamethoxam neonicotinoid causes oxidative damages and alters carotenoid-retinoid levels in caged honey bees (Apis mellifera) - Gauthier_2018_Sci.Rep_8_16274 |
| Author(s) : Gauthier M , Aras P , Paquin J , Boily M |
| Ref : Sci Rep , 8 :16274 , 2018 |
| Abstract : |
| PubMedSearch : Gauthier_2018_Sci.Rep_8_16274 |
| PubMedID: 30390008 |
| Title : Study on neurotoxicity of dinotefuran, thiamethoxam and imidacloprid against Chinese lizards (Eremias argus) - Wang_2018_Chemosphere_217_150 |
| Author(s) : Wang Y , Zhang Y , Li W , Han Y , Guo B |
| Ref : Chemosphere , 217 :150 , 2018 |
| Abstract : |
| PubMedSearch : Wang_2018_Chemosphere_217_150 |
| PubMedID: 30419375 |
| Title : Toxicity and effects of the neonicotinoid thiamethoxam on Scaptotrigona bipunctata lepeletier, 1836 (Hymenoptera: Apidae) - Moreira_2018_Environ.Toxicol_33_463 |
| Author(s) : Moreira DR , Sinopolis Gigliolli AA , Falco JRP , Julio AHF , Volnistem EA , Chagas FD , Toledo VAA , Ruvolo-Takasusuki MCC |
| Ref : Environ Toxicol , 33 :463 , 2018 |
| Abstract : |
| PubMedSearch : Moreira_2018_Environ.Toxicol_33_463 |
| PubMedID: 29377569 |
| Title : Exposure of larvae to thiamethoxam affects the survival and physiology of the honey bee at post-embryonic stages - Tavares_2017_Environ.Pollut_229_386 |
| Author(s) : Tavares DA , Dussaubat C , Kretzschmar A , Carvalho SM , Silva-Zacarin ECM , Malaspina O , Berail G , Brunet JL , Belzunces LP |
| Ref : Environ Pollut , 229 :386 , 2017 |
| Abstract : |
| PubMedSearch : Tavares_2017_Environ.Pollut_229_386 |
| PubMedID: 28618362 |
| Title : Identification and functional characterization of esterases in Euschistus heros (Hemiptera, Pentatomidae) and their relationship with thiamethoxam and lambda-cyhalothrin - Hegeto_2015_Genet.Mol.Res_14_11079 |
| Author(s) : Hegeto LA , Ronqui L , Lapenta AS , Albuquerque FA |
| Ref : Genet Mol Res , 14 :11079 , 2015 |
| Abstract : |
| PubMedSearch : Hegeto_2015_Genet.Mol.Res_14_11079 |
| PubMedID: 26400338 |
| Title : Thiamethoxam Resistance in the House Fly, Musca domestica L.: Current Status, Resistance Selection, Cross-Resistance Potential and Possible Biochemical Mechanisms - Khan_2015_PLoS.One_10_e0125850 |
| Author(s) : Khan HA , Akram W , Iqbal J , Naeem-Ullah U |
| Ref : PLoS ONE , 10 :e0125850 , 2015 |
| Abstract : |
| PubMedSearch : Khan_2015_PLoS.One_10_e0125850 |
| PubMedID: 25938578 |
| Title : Transcriptomic comparison of thiamethoxam-resistance adaptation in resistant and susceptible strains of Aphis gossypii Glover - Pan_2014_Comp.Biochem.Physiol.Part.D.Genomics.Proteomics_13C_10 |
| Author(s) : Pan Y , Peng T , Gao X , Zhang L , Yang C , Xi J , Xin X , Bi R , Shang Q |
| Ref : Comparative Biochemistry & Physiology Part D Genomics Proteomics , 13C :10 , 2014 |
| Abstract : |
| PubMedSearch : Pan_2014_Comp.Biochem.Physiol.Part.D.Genomics.Proteomics_13C_10 |
| PubMedID: 25528611 |
| Title : Synthesis and biological activity of fluorescent neonicotinoid insecticide thiamethoxam - Taillebois_2014_Bioorg.Med.Chem.Lett_24_3552 |
| Author(s) : Taillebois E , Langlois P , Cunha T , Seraphin D , Thany SH |
| Ref : Bioorganic & Medicinal Chemistry Lett , 24 :3552 , 2014 |
| Abstract : |
| PubMedSearch : Taillebois_2014_Bioorg.Med.Chem.Lett_24_3552 |
| PubMedID: 24915877 |
| 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 : |
| PubMedSearch : Gao_2014_Pestic.Biochem.Physiol_114_90 |
| PubMedID: 25175655 |
| Title : Transcriptome profiling of the whitefly Bemisia tabaci reveals stage-specific gene expression signatures for thiamethoxam resistance - Yang_2013_Insect.Mol.Biol_22_485 |
| Author(s) : Yang N , Xie W , Jones CM , Bass C , Jiao X , Yang X , Liu B , Li R , Zhang Y |
| Ref : Insect Molecular Biology , 22 :485 , 2013 |
| Abstract : |
| PubMedSearch : Yang_2013_Insect.Mol.Biol_22_485 |
| PubMedID: 23889345 |
| Title : Neonicotinoid formaldehyde generators: possible mechanism of mouse-specific hepatotoxicity\/hepatocarcinogenicity of thiamethoxam - Swenson_2013_Toxicol.Lett_216_139 |
| Author(s) : Swenson TL , Casida JE |
| Ref : Toxicol Lett , 216 :139 , 2013 |
| Abstract : |
| PubMedSearch : Swenson_2013_Toxicol.Lett_216_139 |
| PubMedID: 23220038 |
| Title : Development of biomarkers of exposure to xenobiotics in the honey bee Apis mellifera: application to the systemic insecticide thiamethoxam - Badiou-Beneteau_2012_Ecotoxicol.Environ.Saf_82_22 |
| Author(s) : Badiou-Beneteau A , Carvalho SM , Brunet JL , Carvalho GA , Bulete A , Giroud B , Belzunces LP |
| Ref : Ecotoxicology & Environmental Safety , 82 :22 , 2012 |
| Abstract : |
| PubMedSearch : Badiou-Beneteau_2012_Ecotoxicol.Environ.Saf_82_22 |
| PubMedID: 22683234 |
| Title : Thiamethoxam, a poor agonist of nicotinic acetylcholine receptors expressed on isolated cell bodies, acts as a full agonist at cockroach cercal afferent\/giant interneuron synapses - Thany_2011_Neuropharmacol_60_587 |
| Author(s) : Thany SH |
| Ref : Neuropharmacology , 60 :587 , 2011 |
| Abstract : |
| PubMedSearch : Thany_2011_Neuropharmacol_60_587 |
| PubMedID: 21172360 |
| Title : Effect of thiamethoxam on cockroach locomotor activity is associated with its metabolite clothianidin - Benzidane_2010_Pest.Manag.Sci_66_1351 |
| Author(s) : Benzidane Y , Touinsi S , Motte E , Jadas-Hecart A , Communal PY , Leduc L , Thany SH |
| Ref : Pest Manag Sci , 66 :1351 , 2010 |
| Abstract : |
| PubMedSearch : Benzidane_2010_Pest.Manag.Sci_66_1351 |
| PubMedID: 20824681 |
| Title : Behavioral and biochemical effects of neonicotinoid thiamethoxam on the cholinergic system in rats - Rodrigues_2010_Ecotoxicol.Environ.Saf_73_101 |
| Author(s) : Rodrigues KJ , Santana MB , Do Nascimento JL , Picanco-Diniz DL , Maues LA , Santos SN , Ferreira VM , Alfonso M , Duran R , Faro LR , Faro LRF |
| Ref : Ecotoxicology & Environmental Safety , 73 :101 , 2010 |
| Abstract : |
| PubMedSearch : Rodrigues_2010_Ecotoxicol.Environ.Saf_73_101 |
| PubMedID: 19481804 |
| 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 : |
| PubMedSearch : Feng_2010_Pest.Manag.Sci_66_313 |
| PubMedID: 19937914 |
| Title : Effects of sublethal doses of acetamiprid and thiamethoxam on the behavior of the honeybee (Apis mellifera) - El Hassani_2008_Arch.Environ.Contam.Toxicol_54_653 |
| Author(s) : El Hassani AK , Dacher M , Gary V , Lambin M , Gauthier M , Armengaud C |
| Ref : Archives of Environmental Contamination & Toxicology , 54 :653 , 2008 |
| Abstract : |
| PubMedSearch : El Hassani_2008_Arch.Environ.Contam.Toxicol_54_653 |
| PubMedID: 18026773 |
| Title : Comparative Toxicities of Pyriproxyfen and Thiamethoxam against the Sweetpotato Whitefly, Bemisia tabaci (Homoptera: Aleyrodidae) - Lee_2002_J.Asia.Pac.Entomol_5_117 |
| Author(s) : Lee YS , Lee SY , Park EC , Kim JH , Kim GH |
| Ref : Journal of Asia-Pacific Entomology , 5 :117 , 2002 |
| Abstract : |
| PubMedSearch : Lee_2002_J.Asia.Pac.Entomol_5_117 |
| PubMedID: |
| Title : Chemistry and biology of thiamethoxam: a second generation neonicotinoid - Maienfisch_2001_Pest.Manag.Sci_57_906 |
| Author(s) : Maienfisch P , Angst M , Brandl F , Fischer W , Hofer D , Kayser H , Kobel W , Rindlisbacher A , Senn R , Steinemann A , Widmer H |
| Ref : Pest Manag Sci , 57 :906 , 2001 |
| Abstract : |
| PubMedSearch : Maienfisch_2001_Pest.Manag.Sci_57_906 |
| PubMedID: |