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+
| Molecular Formula | C10H11ClN4 |
| Molecular Weight | 222.674 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Effect of seven new orchard pesticides on Galendromus occidentalis in laboratory studies. | 2009-06 |
|
| [The effect of pesticide acetamiprid on biochemical markers in tissues of fresh water bivalve mussels Anodonta cygnea L. (Unionidae)]. | 2009-03-03 |
|
| Kinetics of acetamiprid photolysis in solution. | 2009-02 |
|
| Subchronic exposure of honeybees to sublethal doses of pesticides: effects on behavior. | 2009-01 |
|
| Determination of neonicotinoid insecticides residues in bovine milk samples by solid-phase extraction clean-up and liquid chromatography with diode-array detection. | 2008-12-19 |
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| Relative repellency and lethality of the neonicotinoids thiamethoxam and acetamiprid and an acetamiprid/bifenthrin combination to Reticulitermes flavipes termites. | 2008-12 |
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| Impact of decreasing ratios of insecticide-treated seed on flea beetle (Coleoptera: Chrysomelidae, Phyllotreta spp.) feeding levels and canola seed yields. | 2008-12 |
|
| Applied aspects of neonicotinoid uses in crop protection. | 2008-11 |
|
| [Acute poisoning with neonicotinoid insecticide acetamiprid]. | 2008-10 |
|
| Persistence of a neonicotinoid insecticide, acetamiprid on chili (Capsicum annum L.). | 2008-10 |
|
| Resistance of codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae), larvae in Michigan to insecticides with different modes of action and the impact on field residual activity. | 2008-09 |
|
| N-demethylation of neonicotinoid insecticide acetamiprid by bacterium Stenotrophomonas maltophilia CGMCC 1.1788. | 2008-09 |
|
| Toxicity, repellency, and effects of acetamiprid on western subterranean termite (Isoptera: Rhinotermitidae). | 2008-08 |
|
| The presence of Rickettsia is associated with increased susceptibility of Bemisia tabaci (Homoptera: Aleyrodidae) to insecticides. | 2008-08 |
|
| Effect of light on the degradation of two neonicotinoids viz acetamiprid and thiacloprid in soil. | 2008-08 |
|
| Potential of 11 pesticides to initiate downstream drift of stream macroinvertebrates. | 2008-08 |
|
| [Study on determination of acetamiprid and interaction between acetamiprid and deoxyribonucleic acid by resonance light scattering]. | 2008-06 |
|
| Development of a method for the determination of 9 currently used cotton pesticides by gas chromatography with electron capture detection. | 2008-05-30 |
|
| Effects of sublethal doses of acetamiprid and thiamethoxam on the behavior of the honeybee (Apis mellifera). | 2008-05 |
|
| Advances in control of onion thrips (Thysanoptera: Thripidae) in cabbage. | 2008-04 |
|
| Mortality of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), after topical application of various insecticides. | 2008-04 |
|
| Effectiveness of attract-and-kill systems using methyl eugenol incorporated with neonicotinoid insecticides against the oriental fruit fly (Diptera: Tephritidae). | 2008-04 |
|
| Intestinal absorption of the acetamiprid neonicotinoid by Caco-2 cells: transepithelial transport, cellular uptake and efflux. | 2008-03-28 |
|
| Nitrate reductase, arginine deaminase, urease and dehydrogenase activities in natural soil (ridges with forest) and in cotton soil after acetamiprid treatments. | 2008-03 |
|
| Neural actions of imidacloprid and their involvement in resistance in the Colorado potato beetle, Leptinotarsa decemlineata (Say). | 2008-01 |
|
| Temporal synergism can enhance carbamate and neonicotinoid insecticidal activity against resistant crop pests. | 2008-01 |
|
| 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 |
|
| Laboratory studies to elucidate the residual toxicity of eight insecticides to Anystis baccarum (Acari: Anystidae). | 2007-08 |
|
| Toxicity of seven foliar insecticides to four insect parasitoids attacking citrus and cotton pests. | 2007-08 |
|
| Current status of the greenhouse whitefly, Trialeurodes vaporariorum, susceptibility to neonicotinoid and conventional insecticides on strawberries in southern California. | 2007-08 |
|
| [Quantum chemistry study on fluorescence spectra of three aromatic hydrocarbons]. | 2007-07 |
|
| [Insecticide resistance of Bemisia tabaci field populations]. | 2007-07 |
|
| In vitro evaluation of the genotoxicity of acetamiprid in human peripheral blood lymphocytes. | 2007-07 |
|
| Agonist actions of neonicotinoids on nicotinic acetylcholine receptors expressed by cockroach neurons. | 2007-07 |
|
| Toxicity of insecticides to the sweetpotato whitefly (Hemiptera: Aleyrodidae) and its natural enemies. | 2007-07 |
|
| Acetamiprid, carbendazim, diuron and thiamethoxam sorption in two Brazilian tropical soils. | 2007-06-15 |
|
| Selection of a field population of diamondback moth (Lepidoptera: Plutellidae) with acetamiprid maintains, but does not increase, cross-resistance to pyrethroids. | 2007-06 |
|
| Persistence of acetamiprid in soil. | 2007-05 |
|
| Activity of an essential oil derived from Chenopodium ambrosioides on greenhouse insect pests. | 2007-04 |
|
| [High performance liquid chromatography for determination of acetamiprid in serum]. | 2007-03 |
|
| Development of polyclonal antibody based enzyme-linked immunosorbent assay for the analysis of the agricultural insecticide imidacloprid: food quality and safety. | 2007 |
|
| Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice. | 2006-11 |
|
| A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. | 2006-11 |
|
| Immunoassay for acetamiprid detection: application to residue analysis and comparison with liquid chromatography. | 2006-11 |
|
| Susceptibility of immature stages of Homalodisca coagulata (Hemiptera: Cicadellidae) to selected insecticides. | 2006-10 |
|
| Patterns of insecticide resistance in onion thrips (Thysanoptera: Thripidae) in onion fields in New York. | 2006-10 |
|
| Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae). | 2006-10 |
|
| Response of superoxide dismutase, catalase, and ATPase activity in bacteria exposed to acetamiprid. | 2006-08 |
|
| Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam. | 2006-06-30 |
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).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:56:49 GMT 2025
by
admin
on
Mon Mar 31 18:56:49 GMT 2025
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| Record UNII |
5HL5N372P0
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
99050
Created by
admin on Mon Mar 31 18:56:49 GMT 2025 , Edited by admin on Mon Mar 31 18:56:49 GMT 2025
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| Code System | Code | Type | Description | ||
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5HL5N372P0
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160430-64-8
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ALTERNATIVE | |||
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Acetamiprid
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DTXSID0034300
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7274
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acetamiprid
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135410-20-7
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39164
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C464485
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m1318
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PRIMARY | Merck Index |