Flupyradifurone

Flupyradifurone
Flupyradifurone
Flupyradifurone
Names
IUPAC name
4-[(6-Chloropyridine-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one
Other names
Flupyradifurone, Sivanto
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.231.094
EC Number
  • 804-373-8
UNII
  • InChI=1S/C12H11ClF2N2O2/c13-10-2-1-8(4-16-10)5-17(6-11(14)15)9-3-12(18)19-7-9/h1-4,11H,5-7H2
    Key: QOIYTRGFOFZNKF-UHFFFAOYSA-N
  • C1C(=CC(=O)O1)N(CC2=CN=C(C=C2)Cl)CC(F)F
Properties
C12H11ClF2N2O2
Molar mass 288.68 g·mol−1
Appearance White to beige solid
Odor None
Density 1.43 g/mL
Melting point 69 °C (156 °F; 342 K)
3.2 g/L (pH 4)

3.0 g/L (pH 7)

Solubility in Other 0.0005 g/L (n-Heptane)

>250 g/L (Methanol)

Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H373, H410
P260, P264, P270, P273, P301+P312, P314, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Flupyradifurone is a systemic butenolide insecticide developed by Bayer CropScience under the name Sivanto.[1] Flupyradifurone protects crops from sap-feeding pests such as aphids and is safer for non-target organisms compared to other insecticides. Sivanto was launched in 2014 since it obtained its first commercial registration in central America (Guatemala and Honduras).[2] Insecticide Resistance Action Committee (IRAC) classified Flupyradifurone as 4D subset (butenolide) and it is the first pesticide in the butenolide category.[3][4] It was approved by European Union in 2015.[5]

Characteristics

Aphid

Flupyradifurone is used to control sucking pests such as aphids, leafhoppers, psyllids, and whiteflies.[6] It is a systemic insecticide that is absorbed by plants and transported through the xylem. It can be applied on leaves, soil, or seed.[7]

Flupyradifurone is structurally related to the natural insecticide, stemofoline which occurs in the plant species Stemona japonica.[8][2] Stemofoline has some advantageous features, such as being fast-acting and an effective antifeedant, but does not efficiently bind to insect nicotinic acetylcholine receptors.[9][10]

Mode of action

Flupyradifurone is an agonist of insect nicotinic acetylcholine receptors,[2] causing depolarization of nerve cells membranes.[11] Insects cannot detoxify flupyradifurone according to the research of CYP6CM1-mediated metabolism.[2] Since flupyradifurone cannot be inactivated by acetylcholinesterase, it will lead to the failure of nerve system of insects and end up with the death of insects.[11]

Toxicological and ecotoxicological safety

Using the U.S. Environmental Protection Agency guidelines to classify carcinogenic effects, flupyradifurone is categorized as "not likely to be carcinogenic to humans." It is not irritant to humans' eyes and skin,[2][12] and the EPA is not concerned about occupational exposure.[12]

Flupyradifurone is considered a reduced risk insecticide for beneficial insects or other non-target organisms, especially compared to broad-spectrum insecticides such as pyrethroids, neonicotinoids, and organophosates.[13][14] Its toxicity to honey bees is categorized as very low with a contact LD50 of > 100µg/bee and generally does not have adverse effects on honey bees or bumble bees.[6] Flupyradifurone will bind to the nicotinic acetylcholine receptors of honey bees; however, it will only affect the taste and appetitive learning performance at the highest labeled concentration.[15] However, it is highly toxic to aquatic invertebrates.[16]

References

  1. ↑ Jeschke, Peter; Nauen, Ralf; Beck, Michael Edmund (2013). "Nicotinic Acetylcholine Receptor Agonists: A Milestone for Modern Crop Protection". Angewandte Chemie International Edition. 52 (36): 9464–9485. Bibcode:2013ACIE...52.9464J. doi:10.1002/anie.201302550. ISSN 1521-3773. PMID 23934864.
  2. 1 2 3 4 5 Nauen, Ralf; Jeschke, Peter; Velten, Robert; Beck, Michael E.; Ebbinghaus-Kintscher, Ulrich; Thielert, Wolfgang; Wölfel, Katharina; Haas, Matthias; Kunz, Klaus; Raupach, Georg (2015). "Flupyradifurone: a brief profile of a new butenolide insecticide". Pest Management Science. 71 (6): 850–862. Bibcode:2015PMSci..71..850N. doi:10.1002/ps.3932. ISSN 1526-4998. PMC 4657471. PMID 25351824.
  3. ↑ "Interactive MoA Classification | Insecticide Resistance Action Committee (IRAC)". IRAC. Retrieved 2021-11-30.
  4. ↑ "Regulations.gov". www.regulations.gov. Retrieved 2021-11-30.
  5. ↑ Commission Implementing Regulation (EU) 2015/2084 of 18 November 2015 approving the active substance flupyradifurone, in accordance with Regulation (EC) No 1107/2009 of the European Parliament and of the Council concerning the placing of plant protection products on the market, and amending the Annex to Commission Implementing Regulation (EU) No 540/2011 (Text with EEA relevance), 2015-11-19, retrieved 2021-12-01
  6. 1 2 Umetsu, Noriharu; Shirai, Yuichi (20 February 2026). "A comprehensive review of new pesticides developed between 2015 and 2025". Journal of Pesticide Science. 51 (1) D25-078: 1–43. doi:10.1584/jpestics.D25-078. PMC 13021355. PMID 41908034.
  7. ↑ Satpathy, S.; Gotyal, B.S.; Ramesh Babu, V. (5 March 2020). "Role of novel insecticides in crop protection and their selectivity to natural enemies: A review". Journal of Environmental Biology. 41 (2): 149–160. Bibcode:2020JEnvB..41..149S. doi:10.22438/jeb/41/2/MRN-1275.
  8. ↑ Yamamoto, Izuru; Casida, John E., eds. (1999). Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. p. 46. doi:10.1007/978-4-431-67933-2. ISBN 978-4-431-68011-6. S2CID 34374399.
  9. ↑ Kaltenegger, Elisabeth; Brem, Brigitte; Mereiter, Kurt; Kalchhauser, Hermann; Kählig, Hanspeter; Hofer, Otmar; Vajrodaya, Srumya; Greger, Harald (August 2003). "Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species". Phytochemistry. 63 (7): 803–816. Bibcode:2003PChem..63..803K. doi:10.1016/s0031-9422(03)00332-7. ISSN 0031-9422. PMID 12877922.
  10. ↑ Mungkornasawakul, Pitchaya; Pyne, Stephen G.; Jatisatienr, Araya; Supyen, Damrat; Jatisatienr, Chaiwat; Lie, Wilford; Ung, Alison T.; Skelton, Brian W.; White, Allan H. (2004-03-02). "Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-a]azepine Stemona Alkaloid". Journal of Natural Products. 67 (4): 675–677. Bibcode:2004JNAtP..67..675M. doi:10.1021/np034066u. ISSN 0163-3864. PMID 15104502.
  11. 1 2 "Bayer Sivanto :: The science behind Sivanto". www.sivanto.bayer.com. Retrieved 2021-11-30.
  12. 1 2 "New Active Ingredient and New Use Special Registration Reviews". Minnesota Department of Agriculture. Retrieved 2021-12-01.
  13. ↑ Pinero, Jaime. "New Insecticide Alternative to Neonicotinoids, Safer for Bees". Division of Plant Sciences. ipm.missouri.edu. University of Missouri. Retrieved 21 July 2026.
  14. ↑ "Low Impact Pesticides". Cornell Cooperative Extension. Retrieved 21 July 2026.
  15. ↑ Hesselbach, Hannah; Scheiner, Ricarda (2018-03-21). "Effects of the novel pesticide flupyradifurone (Sivanto) on honeybee taste and cognition". Scientific Reports. 8 (1): 4954. Bibcode:2018NatSR...8.4954H. doi:10.1038/s41598-018-23200-0. ISSN 2045-2322. PMC 5862975. PMID 29563522.
  16. ↑ "Flupyradifurone" (PDF), New Active Ingredient and New Use Special Registration Reviews, Minnesota Department of Agriculture, Pesticide Technical Unit
This page is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.