U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H8ClN5O2S
Molecular Weight 249.678
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLOTHIANIDIN

SMILES

CN\C(NCC1=CN=C(Cl)S1)=N/[N+]([O-])=O

InChI

InChIKey=PGOOBECODWQEAB-UHFFFAOYSA-N
InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)

HIDE SMILES / InChI

Molecular Formula C6H8ClN5O2S
Molecular Weight 249.678
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Determination of the effects on learning and memory performance and related gene expressions of clothianidin in rat models.
2014-10
Effect of thiamethoxam on cockroach locomotor activity is associated with its metabolite clothianidin.
2010-12
Neonicotinoid insecticides disrupt predation on the eggs of turf-infesting scarab beetles.
2010-12
Sudden deaths and colony population decline in Greek honey bee colonies.
2010-11
Risk assessment of insecticides used in rice on miridbug, Cyrtorhinus lividipennis Reuter, the important predator of brown planthopper, Nilaparvata lugens (Stal.).
2010-07
Unreliable pesticide control of the vector psyllid Diaphorina citri (Hemiptera: Psyllidae) for the reduction of microorganism disease transmission.
2010-07
Amplification of a cytochrome P450 gene is associated with resistance to neonicotinoid insecticides in the aphid Myzus persicae.
2010-06-24
Biotransformation of thianicotinyl neonicotinoid insecticides: diverse molecular substituents response to metabolism by bacterium Stenotrophomonas maltophilia CGMCC 1.1788.
2010-06
(E)-5-Benzyl-1-methyl-N-nitro-1,3,5-triazinan-2-imine.
2010-03-20
High levels of miticides and agrochemicals in North American apiaries: implications for honey bee health.
2010-03-19
Effects of the neonicotinoids thiametoxam and clothianidin on in vivo dopamine release in rat striatum.
2010-02-15
Effective use of neonicotinoids for protection of citrus seedlings from invasion by Diaphorina citri (Hemiptera: Psyllidae).
2010-02
Ecotoxicity of neonicotinoid insecticides to bees.
2010
Wireworm management I: stand protection versus wireworm mortality with wheat seed treatments.
2009-12
Responses of the cabbage seedpod weevil, Ceutorhynchus obstrictus (Marsham) (Coleoptera: Curculionidae), to seed treatments of canola (Brassica napus L.) with the neonicotinoid compounds clothianidin and imidacloprid.
2009-12
Comparative acute toxicity of neonicotinoid and pyrethroid insecticides to non-target crayfish (Procambarus clarkii) associated with rice-crayfish crop rotations.
2009-11
Agonist actions of clothianidin on synaptic and extrasynaptic nicotinic acetylcholine receptors expressed on cockroach sixth abdominal ganglion.
2009-11
Curative activity of insecticides on Rhagoletis pomonella (Diptera: Tephritidae) in apples.
2009-10
Translocation of neonicotinoid insecticides from coated seeds to seedling guttation drops: a novel way of intoxication for bees.
2009-10
Effect of pesticides on adult rove beetle Atheta coriaria (Coleoptera: Staphylinidae) survival in growing medium.
2009-10
Multiresidue analysis of pesticides with hydrolyzable functionality in cooked vegetables by liquid chromatography tandem mass spectrometry.
2009-07
Chemistry of polyhalogenated nitrobutadienes, 8: Nitropolychlorobutadienes--precursors for insecticidal neonicotinoids.
2009-06-15
Enzymes and inhibitors in neonicotinoid insecticide metabolism.
2009-06-10
Systemic insecticides for control of black vine weevil (Coleoptera: Curculionidae) in container- and field-grown nursery crops.
2009-06
Surface-applied insecticide treatments for quarantine control of Japanese beetle, Popillia japonica Newman (Coleoptera: Scarabaeidae), larvae in field-grown nursery plants.
2009-04
Impact of currently used or potentially useful insecticides for canola agroecosystems on Bombus impatiens (Hymenoptera: Apidae), Megachile rotundata (Hymentoptera: Megachilidae), and Osmia lignaria (Hymenoptera: Megachilidae).
2009-02
Seasonal phenology and management of Tomarus subtropicus (Coleoptera: Scarabaeidae) in St. Augustinegrass.
2008-12
Correlated responses to neonicotinoid insecticides in clones of the peach-potato aphid, Myzus persicae (Hemiptera: Aphididae).
2008-11
Applied aspects of neonicotinoid uses in crop protection.
2008-11
Application timing and efficacy of alternatives for the insecticidal control of Tipula paludosa Meigen (Diptera: Tipulidae), a new invasive pest of turf in the northeastern United States.
2008-10
Pesticides linked to bee deaths.
2008-08-26
Evaluation of management strategies for bean leaf beetles (Coleoptera: Chrysomelidae) and Bean pod mottle virus (Comoviridae) in soybean.
2008-08
Early timing and new combinations to increase the efficacy of neonicotinoid-entomopathogenic nematode (Rhabditida: Heterorhabditidae) combinations against white grubs (Coleoptera: Scarabaeidae).
2008-07
Lethal and sublethal effects of imidacloprid on Osmia lignaria and clothianidin on Megachile rotundata (Hymenoptera: Megachilidae).
2008-06
Crystal structures of Lymnaea stagnalis AChBP in complex with neonicotinoid insecticides imidacloprid and clothianidin.
2008-06
Mortality of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), after topical application of various insecticides.
2008-04
Transitional sublethal and lethal effects of insecticides after dermal exposures to five economic species of wireworms (Coleoptera: Elateridae).
2008-04
Effectiveness of attract-and-kill systems using methyl eugenol incorporated with neonicotinoid insecticides against the oriental fruit fly (Diptera: Tephritidae).
2008-04
Repellency of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), on exposure to synthetic insecticides in a soil-less bioassay.
2008-04
Differences in Phyllotreta cruciferae and Phyllotreta striolata (Coleoptera: Chrysomelidae) responses to neonicotinoid seed treatments.
2008-02
1-(2-Chloro-1,3-thia-zol-5-ylmeth-yl)-3,5-dimethyl-2-nitrimino-1,2,3,4,5,6-hexa-hydro-1,3,5-triazine.
2007-12-06
Toxicity of systemic neonicotinoid insecticides to avocado thrips in nursery avocado trees.
2007-09
Linear alcohol ethoxylates: insecticidal and synergistic effects on German cockroaches (Blattodea: Blattellidae) and other insects.
2007-06
Exposure to clothianidin seed-treated canola has no long-term impact on honey bees.
2007-06
Insect nicotinic acetylcholine receptor gene families: from genetic model organism to vector, pest and beneficial species.
2007-03
Resistance and cross-resistance to imidacloprid and thiamethoxam in the Colorado potato beetle Leptinotarsa decemlineata.
2007-01
Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice.
2006-11
Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae).
2006-10
Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam.
2006-06-30
Epizootics of an entomopathogenic fungus Entomophthora aphidis Hoggman on the pomegranate aphid aphispunicae passerini (Homoptera: Aphididae).
2006
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:53:40 GMT 2025
Edited
by admin
on Mon Mar 31 20:53:40 GMT 2025
Record UNII
2V9906ABKQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOTHIANIDIN
ISO   MI  
Common Name English
ARENA
Preferred Name English
(E)-1-(2-CHLORO-1,3-THIAZOLE-5-YLMETHYL)-3-METHYL-2-NITROGUANIDINE
Systematic Name English
TI-435
Code English
CGA-322704
Code English
CLOTHIANIDIN [MI]
Common Name English
PONCHO
Brand Name English
(E)-1-(2-CHLORO-1,3-THIAZOL-5-YL METHYL)-3-METHYL-2-NITROGUANIDINE
Systematic Name English
N-((2-CHLORO-5-THIAZOLYL)METHYL)-N'-METHYL-N''-NITROGUANIDINE
Systematic Name English
CLOTHIANIDIN [ISO]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 44309
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
Code System Code Type Description
ALANWOOD
clothianidin
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
MERCK INDEX
m3668
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY Merck Index
HSDB
7281
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
PUBCHEM
213027
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
CAS
131748-59-9
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
MESH
C480342
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID2034465
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
WIKIPEDIA
CLOTHIANIDIN
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
CAS
210880-92-5
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
CHEBI
82044
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
CHEBI
39177
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
SMS_ID
300000026892
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
FDA UNII
2V9906ABKQ
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY
DAILYMED
2V9906ABKQ
Created by admin on Mon Mar 31 20:53:40 GMT 2025 , Edited by admin on Mon Mar 31 20:53:40 GMT 2025
PRIMARY