Acetamiprid
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Basic Info
| Common Name | Acetamiprid(F06104) |
| 2D Structure | |
| FRCD ID | F06104 |
| CAS Number | 160430-64-8 |
| PubChem CID | 213021 |
| Formula | C10H11ClN4 |
| IUPAC Name | N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-methylethanimidamide |
| InChI Key | WCXDHFDTOYPNIE-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H11ClN4/c1-8(14-7-12)15(2)6-9-3-4-10(11)13-5-9/h3-5H,6H2,1-2H3 |
| Canonical SMILES | CC(=NC#N)N(C)CC1=CN=C(C=C1)Cl |
| Isomeric SMILES | CC(=NC#N)N(C)CC1=CN=C(C=C1)Cl |
| Synonyms |
Acetamiprid
135410-20-7
Mospilan
160430-64-8
Intruder
Stonkat
Assail
Piorun
Prize
Acetamiprid [ISO]
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Halopyridines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 2-halopyridines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | 2-halopyridine - Aryl chloride - Aryl halide - Heteroaromatic compound - Amidine - Carboxylic acid amidine - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Azacycle - Organochloride - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organohalogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 222.676 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 280 |
| Monoisotopic Mass | 222.067 |
| Exact Mass | 222.067 |
| XLogP | 1.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Breadfruits (Jackfruits, Other species of genus Artocarpus, not elsewhere mentioned,) | 0163090 | European Union | 0.01* | 27/04/2017 | |
| Durians | 0163100 | European Union | 0.01* | 27/04/2017 | |
| Others (2) | 0830990 | European Union | 0.05* | 27/04/2017 | |
| Citrus fruits | 0110000 | European Union | 0.9 | 27/04/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.9 | 27/04/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.9 | 27/04/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.9 | 27/04/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.9 | 27/04/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.9 | 27/04/2017 | |
| Others (2) | 0110990 | European Union | 0.9 | 27/04/2017 | |
| Tree nuts | 0120000 | European Union | 0.07 | 27/04/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.07 | 27/04/2017 | |
| Brazil nuts | 0120020 | European Union | 0.07 | 27/04/2017 | |
| Cashew nuts | 0120030 | European Union | 0.07 | 27/04/2017 | |
| Chestnuts | 0120040 | European Union | 0.07 | 27/04/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.07 | 27/04/2017 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.07 | 27/04/2017 | |
| Macadamias | 0120070 | European Union | 0.07 | 27/04/2017 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.07 | 27/04/2017 | |
| Pistachios | 0120100 | European Union | 0.07 | 27/04/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Sub-lethal effects of six neonicotinoids on avoidance behavior and reproduction of earthworms (Eisenia fetida). | Ecotoxicol Environ Saf | 2018 Oct 30 | 30015188 |
| Pesticide residues in honey bees, pollen and beeswax: Assessing beehive exposure. | Environ Pollut | 2018 Oct | 29803024 |
| Effects of acetamiprid on life cycle development of predatory mite Amblyseius cucumeris (Acari: Phytoseiidae) after contact exposure. | Chemosphere | 2018 Nov | 30208548 |
| Simultaneous determination of neonicotinoid insecticides and insect growthregulators residues in honey using LC-MS/MS with anion exchanger-disposablepipette extraction. | J Chromatogr A | 2018 Jul 6 | 29735281 |
| Hapten-Grafted Programmed Probe as a Corecognition Element for a CompetitiveImmunosensor to Detect Acetamiprid Residue in Agricultural Products. | J Agric Food Chem | 2018 Jul 25 | 29944365 |
| Apta-nanosensors for detection and quantitative determination of acetamiprid - A pesticide residue in food and environment. | Talanta | 2018 Jan 1 | 28917776 |
| Determination of acetamiprid, imidacloprid, and spirotetramat and their relevant metabolites in pistachio using modified QuEChERS combined with liquidchromatography-tandem mass spectrometry. | Food Chem | 2018 Feb 1 | 28946322 |
| Industrial prune processing and its effect on pesticide residue concentrations. | Food Chem | 2018 Dec 1 | 30064756 |
| Development and Validation of an Ultra-Sensitive UHPLC-MS/MS Method forNeonicotinoid Analysis in Milk. | J Agric Food Chem | 2018 Aug 15 | 30025459 |
| Development of an upconversion fluorescence DNA probe for the detection ofacetamiprid by magnetic nanoparticles separation. | Food Chem | 2018 Aug 15 | 29622212 |
| Binary mixtures of alcohol ethoxylates, nonylphenol ethoxylates and pesticidesexhibit comparative bioactivity against three pests and toxicological risks toaquatic organisms. | Chemosphere | 2018 Aug | 29649663 |
| Neonicotinoids act like endocrine disrupting chemicals in newly-emerged bees and winter bees. | Sci Rep | 2017 Sep 8 | 28887455 |
| Alteration of membrane integrity and respiratory function of brain mitochondriain the rats chronically exposed to a low dose of acetamiprid. | Environ Sci Pollut Res Int | 2017 Oct | 28799110 |
| Exposure of amateur gardeners to pesticides via the non-gloved skin per day. | Food Chem Toxicol | 2017 Oct | 28778749 |
| Semiautomated determination of neonicotinoids and characteristic metabolite inurine samples using TurboFlow™ coupled to ultra high performance liquidchromatography coupled to Orbitrap analyzer. | J Pharm Biomed Anal | 2017 Nov 30 | 28918328 |
| Estimated exposure of hands inside the protective gloves used by non-occupationalhandlers of agricultural pesticides. | J Expo Sci Environ Epidemiol | 2017 Nov | 27578185 |
| Efficacy of Chemicals for the Potential Management of the Queensland Fruit FlyBactrocera tryoni (Froggatt) (Diptera: Tephritidae). | Insects | 2017 May 9 | 28486404 |
| Neonicotinoids transference from the field to the hive by honey bees: Towards apesticide residues biomonitor. | Sci Total Environ | 2017 Mar 1 | 28073057 |
| Monitoring of Pesticide Residues in Commonly Used Fruits and Vegetables inKuwait. | Int J Environ Res Public Health | 2017 Jul 25 | 28757570 |
| SERS-active metal-organic frameworks with embedded gold nanoparticles. | Analyst | 2017 Jul 10 | 28612075 |
Targets
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA2
- Uniprot ID:
- Q15822
- Molecular Weight:
- 59764.82 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]