Thiacloprid
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Basic Info
| Common Name | Thiacloprid(F05877) |
| 2D Structure | |
| FRCD ID | F05877 |
| CAS Number | 111988-49-9 |
| PubChem CID | 115224 |
| Formula | C10H9ClN4S |
| IUPAC Name | [3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]cyanamide |
| InChI Key | HOKKPVIRMVDYPB-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H9ClN4S/c11-9-2-1-8(5-13-9)6-15-3-4-16-10(15)14-7-12/h1-2,5H,3-4,6H2 |
| Canonical SMILES | C1CSC(=NC#N)N1CC2=CN=C(C=C2)Cl |
| Isomeric SMILES | C1CSC(=NC#N)N1CC2=CN=C(C=C2)Cl |
| Synonyms |
(3-((6-Chloro-3-pyridinyl)methyl)-2-thiazolidinylidene)cyanamide
Thiacloprid
111988-49-9
Calypso
Calypso 70WG
Thiacloprid [ISO:BSI]
(Z)-thiacloprid
UNII-DSV3A944A4
HSDB 7268
CHEMBL451432
|
| 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 - Thiazolidine - Heteroaromatic compound - Isothiourea - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Azacycle - Hydrocarbon derivative - Organonitrogen compound - Organochloride - Organohalogen compound - Imine - Organopnictogen compound - Organic nitrogen compound - 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 | 252.72 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 324 |
| Monoisotopic Mass | 252.024 |
| Exact Mass | 252.024 |
| XLogP | 2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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 |
|---|---|---|---|---|---|
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 11/08/2016 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.02* | 11/08/2016 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 1 | 11/08/2016 | |
| Litchis/lychees (Longans, Marulas, Salaks/snake fruits, Spanish limes/mamoncillos/genips, Baels,) | 0162020 | European Union | 0.01* | 11/08/2016 | |
| Passionfruits/maracujas (Banana passionfruits, Giant granadillas, Granadillas, Monstera fruits, Wingedstem passionflower fruits,) | 0162030 | European Union | 0.01* | 11/08/2016 | |
| Courgettes (Angled luffas/teroi, Bottle gourds/calabashes/lauki, Chayotes/christophines, Ivy gourds, Pointed gourds/parwals, Snake gourds, Sopropos/bitter melons/balsam pears, Summer squashes/zucch... | 0232030 | European Union | 0.5 | 11/08/2016 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.01* | 11/08/2016 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 5 | 11/08/2016 | |
| Borage seeds (Corn gromwell seeds, Evening primrose seeds, Honesty seeds, Honesty seeds, Perilla seeds, Purple viper's bugloss seeds,) | 0401120 | European Union | 0.02* | 11/08/2016 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 11/08/2016 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 50 | 11/08/2016 | |
| Black caraway/black cumin (Nigella,) | 0810020 | European Union | 0.08 | 11/08/2016 | |
| Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,) | 0820060 | European Union | 0.05* | 11/08/2016 | |
| Edible offals (other than liver and kidney) | 1016050 | European Union | 0.02 | 11/08/2016 | |
| Amphibians and Reptiles (Crocodiles, Frog legs, Snakes, Turtles, Other Amphibians and Reptiles, Other frog legs from frogs not belonging to the genus Rana,) | 1050000 | European Union | 0.01* | 11/08/2016 | |
| Others (2) | 0401990 | European Union | 0.02* | 11/08/2016 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 11/08/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 11/08/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 11/08/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 11/08/2016 |
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 |
| First evidence of neonicotinoid residues in a long-distance migratory raptor, theEuropean honey buzzard (Pernis apivorus). | Sci Total Environ | 2018 Oct 15 | 29929331 |
| High-Throughput Quantitation of Neonicotinoids in Lyophilized Surface Water byLC-APCI-MS/MS. | J AOAC Int | 2018 May 21 | 29784072 |
| Metabolic Effects of a Chronic Dietary Exposure to a Low-Dose Pesticide Cocktail in Mice: Sexual Dimorphism and Role of the Constitutive Androstane Receptor. | Environ Health Perspect | 2018 Jun 25 | 29950287 |
| 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 |
| Persistence of thiacloprid and deltamethrin residues in tea grown at differentlocations of North-East India. | Food Chem | 2018 Jul 1 | 29502848 |
| Increased survival of honeybees in the laboratory after simultaneous exposure to low doses of pesticides and bacteria. | PLoS One | 2018 Jan 31 | 29385177 |
| Development and Validation of an Ultra-Sensitive UHPLC-MS/MS Method forNeonicotinoid Analysis in Milk. | J Agric Food Chem | 2018 Aug 15 | 30025459 |
| Identification and characterization of pesticide metabolites in Brassica species by liquid chromatography travelling wave ion mobility quadrupole time-of-flightmass spectrometry (UPLC-TWIMS-QTOF-MS). | Food Chem | 2018 Apr 1 | 29120785 |
| 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 |
| Efficacy of Chemicals for the Potential Management of the Queensland Fruit FlyBactrocera tryoni (Froggatt) (Diptera: Tephritidae). | Insects | 2017 May 9 | 28486404 |
| Evaluation of Matrix Effects in Multiresidue Analysis of Pesticide Residues inVegetables and Spices by LC-MS/MS. | J AOAC Int | 2017 May 1 | 28300025 |
| The disappearance rate and risk assessment of thiacloprid residues in Asian pear using liquid chromatography confirmed with tandem mass spectrometry. | Biomed Chromatogr | 2017 May | 27696449 |
| Degradation Dynamics and Dietary Risk Assessments of Two NeonicotinoidInsecticides during Lonicera japonica Planting, Drying, and Tea BrewingProcesses. | J Agric Food Chem | 2017 Mar 1 | 28177236 |
| Agricultural pesticides and veterinary substances in Uruguayan beeswax. | Chemosphere | 2017 Jun | 28284118 |
| Single basal application of thiacloprid for the integrated management of Meloidogyne incognita and Bemisia tabaci in tomato crops. | Sci Rep | 2017 Jan 25 | 28120937 |
| Exposure to neonicotinoid insecticides induces embryotoxicity in mice andrabbits. | Toxicology | 2017 Dec 1 | 29061322 |
| Comparative Efficacy of Insecticides on Bactrocera tryoni and Zeugodacus cucumis (Diptera: Tephritidae) in Laboratory and Semifield Trials in Fruiting Vegetables. | J Econ Entomol | 2017 Aug 1 | 28486631 |
| Use of the synergist piperonyl butoxide can slow the development ofalpha-cypermethrin resistance in the whitefly Bemisia tabaci. | Insect Mol Biol | 2017 Apr | 27869336 |
| Multi-residue detection of pesticides using a sensitive immunochip assay based onnanogold enhancement. | Anal Chim Acta | 2016 Sep 28 | 27619097 |
Targets
- General Function:
- Extracellular ligand-gated ion channel activity
- Gene Name:
- CHRFAM7A
- Uniprot ID:
- Q494W8
- Molecular Weight:
- 46217.335 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 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 ]