Thiamethoxam

Thiamethoxam

E isomer

Z isomer
Names
Preferred IUPAC name
{3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide
Other names
CGA293343
Identifiers
  • Compounds
  • EZ: Thiamethoxam
  • E: E-isomer
  • Z: Z-isomer
3D model (JSmol)
8555232
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.102.703 Edit this at Wikidata
EC Number
  • EZ: 428-650-4
  • E: 604-921-4
KEGG
UNII
  • InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3 checkY
    Key: NWWZPOKUUAIXIW-UHFFFAOYSA-N checkY
  • E: InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8+
    Key: NWWZPOKUUAIXIW-DHZHZOJOSA-N
  • Z: InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-
    Key: NWWZPOKUUAIXIW-FLIBITNWSA-N
  • Z: Clc1ncc(s1)CN2/C(=N\[N+]([O-])=O)N(C)COC2
Properties[1]
C8H10ClN5O3S
Molar mass 291.71 g·mol−1
Density 1.57 g/cm3
Melting point 139.1 °C (282.4 °F; 412.2 K)
4.1 g/L
log P -0.13
Hazards[2]
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H410
P264, P270, P273, P301+P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thiamethoxam is the ISO common name[3] for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

A 2018 review by the European Food Safety Authority (EFSA) concluded that most uses of neonicotinoid pesticides such as Thiamethoxam represent a risk to wild bees and honeybees.[4][5] In 2022 the United States Environmental Protection Agency (EPA) concluded that Thiamethoxam is likely to adversely affect 77 percent of federally listed endangered or threatened species and 81 percent of critical habitats.[6] The pesticide has been banned for all outdoor use in the entire European Union since 2018, but has a partial approval in the U.S. and other parts of the world, where it is widely used.[7][8]

  1. ^ Pesticide Properties Database. "Thiamethoxam". University of Hertfordshire. Retrieved 2022-01-22.
  2. ^ PubChem Database (2022-01-15). "N-[3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene]nitramide". Retrieved 2022-01-22.
  3. ^ "Compendium of Pesticide Common Names". BCPC.
  4. ^ "Neonicotinoids: risks to bees confirmed | EFSA". www.efsa.europa.eu. 2018-02-28. Retrieved 2023-06-23.
  5. ^ "Conclusion on the peer review of the pesticide risk assessment for bees for the active substance clothianidin". EFSA Journal. 11: 3066. 2013. doi:10.2903/j.efsa.2013.3066.
  6. ^ US EPA O (2022-06-16). "EPA Finalizes Biological Evaluations Assessing Potential Effects of Three Neonicotinoid Pesticides on Endangered Species". www.epa.gov. Retrieved 2023-06-23.
  7. ^ Carrington D (2018-04-27). "EU agrees total ban on bee-harming pesticides". The Guardian. ISSN 0261-3077. Retrieved 2023-06-23.
  8. ^ Milman O (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.