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

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of clothianidin on Bombus impatiens (Hymenoptera: Apidae) colony health and foraging ability.
2004 Apr
Evaluation and validation of a commercially available enzyme-linked immunosorbent assay for the neonicotinoid insecticide imidacloprid in agricultural samples.
2004 May 19
Desensitizing and non-desensitizing subtypes of alpha-bungarotoxin-sensitive nicotinic acetylcholine receptors in cockroach neurons.
2004 Oct
Comparative analysis of neonicotinoid binding to insect membranes: I. A structure-activity study of the mode of [3H]imidacloprid displacement in Myzus persicae and Aphis craccivora.
2004 Oct
Neonicotinoid insecticide toxicology: mechanisms of selective action.
2005
Toxicity of four systemic neonicotinoids to adults of Anoplophora glabripennis (Coleoptera: Cerambycidae).
2005 Dec
Evaluation of insecticides and application methods against Contarinia nasturtii (Diptera: Cecidomyiidae), a new invasive insect pest in the United States.
2006 Feb
Effect of Bacillus thuringiensis subsp. israelensis and neonicotinoid insecticides on the fungus gnat Bradysia sp nr. coprophila (Lintner) (Diptera: Sciaridae).
2006 Feb
Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides.
2006 Jan
Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam.
2006 Jun 30
Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice.
2006 Nov
A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides.
2006 Nov
Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae).
2006 Oct
Neonicotinoid insecticides display partial and super agonist actions on native insect nicotinic acetylcholine receptors.
2006 Oct
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 Dec 6
Resistance and cross-resistance to imidacloprid and thiamethoxam in the Colorado potato beetle Leptinotarsa decemlineata.
2007 Jan
Exposure to clothianidin seed-treated canola has no long-term impact on honey bees.
2007 Jun
Insect nicotinic acetylcholine receptor gene families: from genetic model organism to vector, pest and beneficial species.
2007 Mar
Repellency of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), on exposure to synthetic insecticides in a soil-less bioassay.
2008 Apr
Pesticides linked to bee deaths.
2008 Aug 26
Seasonal phenology and management of Tomarus subtropicus (Coleoptera: Scarabaeidae) in St. Augustinegrass.
2008 Dec
Differences in Phyllotreta cruciferae and Phyllotreta striolata (Coleoptera: Chrysomelidae) responses to neonicotinoid seed treatments.
2008 Feb
Early timing and new combinations to increase the efficacy of neonicotinoid-entomopathogenic nematode (Rhabditida: Heterorhabditidae) combinations against white grubs (Coleoptera: Scarabaeidae).
2008 Jul
Correlated responses to neonicotinoid insecticides in clones of the peach-potato aphid, Myzus persicae (Hemiptera: Aphididae).
2008 Nov
Surface-applied insecticide treatments for quarantine control of Japanese beetle, Popillia japonica Newman (Coleoptera: Scarabaeidae), larvae in field-grown nursery plants.
2009 Apr
Wireworm management I: stand protection versus wireworm mortality with wheat seed treatments.
2009 Dec
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 Dec
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 Feb
Multiresidue analysis of pesticides with hydrolyzable functionality in cooked vegetables by liquid chromatography tandem mass spectrometry.
2009 Jul
Systemic insecticides for control of black vine weevil (Coleoptera: Curculionidae) in container- and field-grown nursery crops.
2009 Jun
Enzymes and inhibitors in neonicotinoid insecticide metabolism.
2009 Jun 10
Chemistry of polyhalogenated nitrobutadienes, 8: Nitropolychlorobutadienes--precursors for insecticidal neonicotinoids.
2009 Jun 15
Comparative acute toxicity of neonicotinoid and pyrethroid insecticides to non-target crayfish (Procambarus clarkii) associated with rice-crayfish crop rotations.
2009 Nov
Agonist actions of clothianidin on synaptic and extrasynaptic nicotinic acetylcholine receptors expressed on cockroach sixth abdominal ganglion.
2009 Nov
Curative activity of insecticides on Rhagoletis pomonella (Diptera: Tephritidae) in apples.
2009 Oct
Translocation of neonicotinoid insecticides from coated seeds to seedling guttation drops: a novel way of intoxication for bees.
2009 Oct
Effect of pesticides on adult rove beetle Atheta coriaria (Coleoptera: Staphylinidae) survival in growing medium.
2009 Oct
Ecotoxicity of neonicotinoid insecticides to bees.
2010
Effect of thiamethoxam on cockroach locomotor activity is associated with its metabolite clothianidin.
2010 Dec
Neonicotinoid insecticides disrupt predation on the eggs of turf-infesting scarab beetles.
2010 Dec
Effective use of neonicotinoids for protection of citrus seedlings from invasion by Diaphorina citri (Hemiptera: Psyllidae).
2010 Feb
Effects of the neonicotinoids thiametoxam and clothianidin on in vivo dopamine release in rat striatum.
2010 Feb 15
Risk assessment of insecticides used in rice on miridbug, Cyrtorhinus lividipennis Reuter, the important predator of brown planthopper, Nilaparvata lugens (Stal.).
2010 Jul
Unreliable pesticide control of the vector psyllid Diaphorina citri (Hemiptera: Psyllidae) for the reduction of microorganism disease transmission.
2010 Jul
Biotransformation of thianicotinyl neonicotinoid insecticides: diverse molecular substituents response to metabolism by bacterium Stenotrophomonas maltophilia CGMCC 1.1788.
2010 Jun
Amplification of a cytochrome P450 gene is associated with resistance to neonicotinoid insecticides in the aphid Myzus persicae.
2010 Jun 24
High levels of miticides and agrochemicals in North American apiaries: implications for honey bee health.
2010 Mar 19
(E)-5-Benzyl-1-methyl-N-nitro-1,3,5-triazinan-2-imine.
2010 Mar 20
Sudden deaths and colony population decline in Greek honey bee colonies.
2010 Nov
Determination of the effects on learning and memory performance and related gene expressions of clothianidin in rat models.
2014 Oct
Patents
Name Type Language
CLOTHIANIDIN
ISO   MI  
Common 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
ARENA
Brand 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 Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
Code System Code Type Description
ALANWOOD
clothianidin
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
MERCK INDEX
m3668
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY Merck Index
HSDB
7281
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
PUBCHEM
213027
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
CAS
131748-59-9
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
MESH
C480342
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID2034465
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
WIKIPEDIA
CLOTHIANIDIN
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
CAS
210880-92-5
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
CHEBI
82044
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
CHEBI
39177
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
SMS_ID
300000026892
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY
FDA UNII
2V9906ABKQ
Created by admin on Sat Dec 16 01:32:20 GMT 2023 , Edited by admin on Sat Dec 16 01:32:20 GMT 2023
PRIMARY