Thiacloprid

Thiacloprid
Names
IUPAC name
{(2Z)-3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide
Other names
[3-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]cyanamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.129.728 Edit this at Wikidata
KEGG
UNII
  • 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/b14-10- checkY
    Key: HOKKPVIRMVDYPB-UVTDQMKNSA-N checkY
  • Clc1ncc(cc1)CN2C(=N\C#N)\SCC2
Properties[2]
C10H9ClN4S
Molar mass 252.72 g·mol−1
Appearance Yellowish crystalline solid
Density 1.46 g·cm−3 at 20 °C
Melting point 136 °C (277 °F; 409 K)
185 mg/L at 20°C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Thiacloprid is an insecticide of the neonicotinoid class. Its mechanism of action is similar to other neonicotinoids and involves disruption of the insect's nervous system by stimulating nicotinic acetylcholine receptors. Thiacloprid was developed by Bayer CropScience for use on agricultural crops to control of a variety of sucking and chewing insects, primarily aphids and whiteflies.[2][3]

Regulation

See also: Neonicotinoid § European Union

Thiacloprid has been banned in France since September 1, 2018.[4] The 5 neonicotinoids banned in France are Acetamiprid, Clothianidin, Imidacloprid, Thiacloprid and Thiamethoxam.[5]

References

  1. ^ "Thiacloprid". Bayer CropScience Crop Compendium. Bayer CropScience. Archived from the original on 23 October 2011. Retrieved 30 November 2011. (June 2019, website structure changed; site search gives 16 search results for thiacloprid, all apparently under 'Crop Science', none in the compendium)
  2. ^ a b Thiacloprid Pesticide Fact Sheet, United States Environmental Protection Agency Archived 2012-06-27 at the Wayback Machine
  3. ^ Schuld M, Schmuck R (2000). "Effects of Thiacloprid, a New Chloronicotinyl Insecticide, On the Egg Parasitoid Trichogramma cacaoeciae". Ecotoxicology. 9 (3): 197–205. doi:10.1023/A:1008994705074. ISSN 0963-9292. S2CID 83596241.
  4. ^ LOI No. 2016-1087 du 8 août 2016 pour la reconquête de la biodiversité, de la nature et des paysages, article 125, accessed 3 July 2019
  5. ^ Décret n° 2018-675 du 30 juillet 2018 relatif à la définition des substances actives de la famille des néonicotinoïdes présentes dans les produits phytopharmaceutiques, accessed 3 July 2019

Thiacloprid listing at pubchem pubchem.ncbi.nlm.nih.gov

Thiacloprid listing at toxnet toxnet.nlm.nih.gov (Reviewed 3/28/2019)[dead link‍]

Thiacloprid, as active substance and as formulation, poses a substantial risk to honey bees by disrupting learning and memory functions. Honey bees (Apis mellifera carnica) were exposed chronically to thiacloprid in the field for several weeks at a sublethal concentration. Foraging behavior, homing success, navigation performance, and social communication were impaired, and thiacloprid residue levels increased both in the foragers and the nest mates over time. Thiacloprid exposed free-flying bumblebee colonies were more likely to die prematurely, and those that survived reached a lower final weight and produced 46% fewer reproductives than colonies placed at control farms.

Thiacloprid; Pesticide Tolerances: A Rule by the Environmental Protection Agency on 02/06/2013 federalregister.gov

Pesticide Fact Sheet Name of Chemical: ThiaclopridReason for Issuance: Conditional RegistrationDate Issued: September 26, 2003 www3.epa.gov

D. Beneficial Insects:. Based upon the results of core bee toxicity tests, it is predicted that thiacloprid will not adversely affect bees. In addition, thiacloprid toxicity is unlike other neonicotinoid insecticides (i.e.: imidacloprid, and clothianidin) which have demonstrated very high to high acute toxicity to bees. (p. 10)

PPDB: Pesticide Properties DataBase at University of Hertfordshire Describes Toxicity to Apis mellifera as 'Moderate' Briefing: Thiacloprid: A bee harming pesticide friendsoftheearth.uk (ca. 2014)

Conclusion ...Evidence from independent scientific research indicates that thiacloprid is harmful to bees especially when its use is combined with other pressures on these insects. Thiacloprid has been approved for use on the basis of an inadequate testing regime which does not look for impacts on wild bees, does not assess sub lethal effects of longer term exposure or the interaction between the active ingredient and other substances or even other pressures on bees...