Clothianidin

Clothianidin
Partially condensed, Kekulé, skeletal formula
Names
IUPAC name
1-(2-Chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine[1]
Identifiers
3D model (JSmol)
9196326, 8620724 (E)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.103.171 Edit this at Wikidata
KEGG
MeSH Clothianidin
UNII
  • InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11) checkY
    Key: PGOOBECODWQEAB-UHFFFAOYSA-N checkY
  • InChI=1/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)
    Key: PGOOBECODWQEAB-UHFFFAOYAT
  • CNC(N[N+]([O-])=O)=NCC1=CN=C(Cl)S1
Properties
C6H8ClN5O2S
Molar mass 249.67 g·mol−1
Appearance Colorless crystals
Density 1.61 g cm−3
Melting point 179 °C (354 °F; 452 K)
327 mg/L (at 20 °C)
log P 0.732
Acidity (pKa) 7.472
Basicity (pKb) 6.525
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 ?)

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.

A 2018 review by the European Food Safety Authority (EFSA) concluded that most uses of neonicotinoid pesticides such as clothianidin represent a risk to wild bees and honeybees.[2][3] In 2022 the United States Environmental Protection Agency (EPA) concluded that clothianidin is likely to adversely affect 67 percent of federally listed endangered or threatened species and 56 percent of critical habitats.[4] The pesticide has been banned for all outdoor use in the entire European Union since 2018, but has a conditional approval in the U.S. and other parts of the world, where it is widely used.[5][6]

Clothianidin is an alternative to organophosphate, carbamate, and pyrethroid pesticides. It poses lower risks to mammals, including humans, when compared to organophosphates and carbamates. It has helped prevent insect pests from building up resistance to organophosphate and pyrethroid pesticides.[7][8][9]

  1. ^ CID 213027 from PubChem
  2. ^ "Neonicotinoids: risks to bees confirmed | EFSA". www.efsa.europa.eu. 2018-02-28. Retrieved 2023-06-23.
  3. ^ European Food Safety Authority (16 January 2013) "Conclusion on the peer review of the pesticide risk assessment for bees for the active substance clothianidin" EFSA Journal 11(1):3066.
  4. ^ US EPA, OCSPP (2022-06-16). "EPA Finalizes Biological Evaluations Assessing Potential Effects of Three Neonicotinoid Pesticides on Endangered Species". www.epa.gov. Retrieved 2023-06-23.
  5. ^ Carrington, Damian (2018-04-27). "EU agrees total ban on bee-harming pesticides". The Guardian. ISSN 0261-3077. Retrieved 2023-06-23.
  6. ^ Milman, Oliver (2022-03-08). "Fears for bees as US set to extend use of toxic pesticides that paralyse insects". The Guardian. ISSN 0261-3077. Retrieved 2023-06-23.
  7. ^ "USEPA Clothianidin fact sheet" (PDF). U.S. Environmental Protection Agency. Retrieved 14 October 2013.
  8. ^ "Australian evaluation of the new active CLOTHIANIDIN" (PDF). Australian Pesticides and Veterinary Medicines Authority. Archived from the original (PDF) on 30 September 2011. Retrieved 15 August 2011.
  9. ^ "Background Information On Use Of Neonicotinoid Pesticides And Their Effects On Bees". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.