Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H11ClN4 |
| Molecular Weight | 222.674 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CC1=CC=C(Cl)N=C1)C(\C)=N\C#N
InChI
InChIKey=WCXDHFDTOYPNIE-RIYZIHGNSA-N
InChI=1S/C10H11ClN4/c1-8(14-7-12)15(2)6-9-3-4-10(11)13-5-9/h3-5H,6H2,1-2H3/b14-8+
Acetamiprid is a carboxamidine that is acetamidine in which the amino hydrogens are substituted by a (6-chloropyridin-3-yl)methyl and a methyl group while the hydrogen attached to the imino nitrogen is replaced by a cyano group. It has a role as a neonicotinoid insectide, an environmental contaminant and a xenobiotic. It is a monochloropyridine, a nitrile and a carboxamidine. It derives from a 2-chloropyridine. Acetamiprid is an insecticide that is currently approved for EU use. It is highly soluble in water and is volatile. Based on its chemical properties it would not be expected to leach to groundwater. It is not persistence in soil systems but may be very persistent in aquatic systems under certain conditions. It has a moderate mammalian toxicity and it has a high potential for bioaccumulation. Acetamiprid is a recognised irritant. It is highly toxic to birds and earthworms and moderately toxic to most aquatic organisms. Acetamiprid is a nicotinic agonist that reacts with nicotinic acetylcholine receptors (nACh-R). The activation of the nACh-R receptors causes hyperactivity and muscle spasms, and eventually death.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Study on the interaction between nucleic acids and acetamiprid. | 2003 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 |
|
| Rapid report acetamiprid resistance and cross-resistance in the diamondback moth, Plutella xylostella. | 2004 Sep |
|
| Monitoring multi-class pesticide residues in fresh fruits and vegetables by liquid chromatography with tandem mass spectrometry. | 2004 Sep 10 |
|
| Effects of a neonicotinoid insecticide (acetamiprid) on acetylcholinesterase activity and cuticular hydrocarbons profil in German cockroaches. | 2005 |
|
| Role of neonicotinyl insecticides in Washington apple integrated pest management. Part II. Nontarget effects on integrated mite control. | 2005 |
|
| Biotypes B and Q of Bemisia tabaci and their relevance to neonicotinoid and pyriproxyfen resistance. | 2005 Apr |
|
| Activity of selected neonicotinoids and dicrotophos on nontarget arthropods in cotton: implications in insect management. | 2005 Jun |
|
| Persistence of Acetamiprid in/on Mustard (Brassica juncea L.). | 2006 Feb |
|
| Susceptibility of pest Nezara viridula (Heteroptera: Pentatomidae) and parasitoid Trichopoda pennipes (Diptera: Tachinidae) to selected insecticides. | 2006 Jun |
|
| Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam. | 2006 Jun 30 |
|
| Insect nicotinic acetylcholine receptors: neonicotinoid binding site specificity is usually but not always conserved with varied substituents and species. | 2006 May 3 |
|
| Patterns of insecticide resistance in onion thrips (Thysanoptera: Thripidae) in onion fields in New York. | 2006 Oct |
|
| Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae). | 2006 Oct |
|
| Current status of the greenhouse whitefly, Trialeurodes vaporariorum, susceptibility to neonicotinoid and conventional insecticides on strawberries in southern California. | 2007 Aug |
|
| [Insecticide resistance of Bemisia tabaci field populations]. | 2007 Jul |
|
| In vitro evaluation of the genotoxicity of acetamiprid in human peripheral blood lymphocytes. | 2007 Jul |
|
| Studies on residues of pesticides used in rape plants protection in surface waters of intensively exploited arable lands in Wielkopolska Province of Poland. | 2008 |
|
| Olfactory interference during inhibitory backward pairing in honey bees. | 2008 |
|
| Toxicity, repellency, and effects of acetamiprid on western subterranean termite (Isoptera: Rhinotermitidae). | 2008 Aug |
|
| The presence of Rickettsia is associated with increased susceptibility of Bemisia tabaci (Homoptera: Aleyrodidae) to insecticides. | 2008 Aug |
|
| Effect of light on the degradation of two neonicotinoids viz acetamiprid and thiacloprid in soil. | 2008 Aug |
|
| Relative repellency and lethality of the neonicotinoids thiamethoxam and acetamiprid and an acetamiprid/bifenthrin combination to Reticulitermes flavipes termites. | 2008 Dec |
|
| Impact of decreasing ratios of insecticide-treated seed on flea beetle (Coleoptera: Chrysomelidae, Phyllotreta spp.) feeding levels and canola seed yields. | 2008 Dec |
|
| Determination of neonicotinoid insecticides residues in bovine milk samples by solid-phase extraction clean-up and liquid chromatography with diode-array detection. | 2008 Dec 19 |
|
| Neural actions of imidacloprid and their involvement in resistance in the Colorado potato beetle, Leptinotarsa decemlineata (Say). | 2008 Jan |
|
| [Study on determination of acetamiprid and interaction between acetamiprid and deoxyribonucleic acid by resonance light scattering]. | 2008 Jun |
|
| Applied aspects of neonicotinoid uses in crop protection. | 2008 Nov |
|
| [Acute poisoning with neonicotinoid insecticide acetamiprid]. | 2008 Oct |
|
| Persistence of a neonicotinoid insecticide, acetamiprid on chili (Capsicum annum L.). | 2008 Oct |
|
| [The effect of pesticide acetamiprid on biochemical markers in tissues of fresh water bivalve mussels Anodonta cygnea L. (Unionidae)]. | 2008 Sep-Oct |
|
| Kinetics of acetamiprid photolysis in solution. | 2009 Feb |
|
| Subchronic exposure of honeybees to sublethal doses of pesticides: effects on behavior. | 2009 Jan |
|
| Effect of seven new orchard pesticides on Galendromus occidentalis in laboratory studies. | 2009 Jun |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Male mice, rats or rabbits were administered single doses of acetamiprid by gavage, intraperitoneal injection (i.p.) or intravenous injection (i.v.) up to 60 mg/kg. The animals were assessed for a variety of neurobehavioral parameters. Based on a number of neuromuscular, behavioral and physiological effects of acetamiprid in male mice, under the conditions of this study, a overall NOAEL of 10 mg/kg (threshold) and LOAEL of 20 mg/kg could be estimated for a single dose by various exposure routes. https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-099050_15-Mar-02.pdf
In mice and rats, the oral median lethal dose (LD50) was in the range of 140–417 mg/kg body weight (bw). In a 13-week study in mice, the no-observed-adverse-effect level (NOAEL) was 400 ppm (equal to 53.2 mg/kg bw per day), on the basis of a significant decrease in total cholesterol level in females at 800 ppm (equal to 106.1 mg/kg bw per day).
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Two-electrode voltage-clamp electrophysiology was used to characterize the pharmacology of three neonicotinoid insecticides on nicotinic α7 receptors expressed in Xenopus oocytes. Single and combined application of clothianidin, acetamiprid and thiamethoxam were tested.
Pretreatment with clothianidin and acetamiprid (10 uM) ACh significantly enhanced the subsequent currents evoked by ACh (100 uM).
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
EPA PESTICIDE CODE |
99050
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
5HL5N372P0
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
160430-64-8
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
ALTERNATIVE | |||
|
Acetamiprid
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
DTXSID0034300
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
7274
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
acetamiprid
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
135410-20-7
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
39164
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
C464485
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | |||
|
m1318
Created by
admin on Fri Dec 15 17:54:14 GMT 2023 , Edited by admin on Fri Dec 15 17:54:14 GMT 2023
|
PRIMARY | Merck Index |
SUBSTANCE RECORD
