Indaziflam

Source: Wikipedia, the free encyclopedia.

Indaziflam
Names
IUPAC name
2-N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine[1]
Identifiers
3D model (
JSmol
)
20920435
ChEBI
ChemSpider
ECHA InfoCard
 100.216.692 Edit this at Wikidata
UNII
  • InChI=1S/C16H20FN5/c1-8-4-5-11-7-9(2)13(12(11)6-8)19-16-21-14(10(3)17)20-15(18)22-16/h4-6,9-10,13H,7H2,1-3H3,(H3,18,19,20,21,22)/t9-,10?,13+/m0/s1
    Key: YFONKFDEZLYQDH-BOURZNODSA-N
  • C[C@H]1CC2=C([C@@H]1NC3=NC(=NC(=N3)N)C(C)F)C=C(C=C2)C
Properties[2]
C16H20FN5
Molar mass 301.369 g·mol−1
Density 1.23 g/mL
Melting point 183 °C (361 °F; 456 K)
2.8 mg/L (20 °C)
log P 2.8
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Warning
H373, H410
P260, P273, P314, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.

History

In 1991, the Japanese company

Bayer scientists subsequently investigated this area of chemistry and identified indaziflam as having superior properties, which they patented and developed under the code number BCS-AA10717.[6][7] The compound was first registered for use in the USA in 2010.[8][9]

Mechanism of action

Indaziflam is an

Herbicide Resistance Action Committee.[11][12]

Resistance

As of March 2021[update] there are no resistant populations known[13] and none for the broader CBI class (discounting quinclorac).[11][14][15][16][17]

Brand names

Indaziflam composes all or part of the a.i. of several herbicides from Bayer Environmental Science (now owned by Cinven, aka Envu, per Bayer's and Envu's websites), [18]

Bayer CropScience (the inventor of the ingredient), like Alion.[26]

Uses

Indaziflam is approved in the United States for

tree nuts.[27] It is used as a preemergent.[28][27]

References

  1. ^ Weed Science Society of America. "Common and chemical names approved by WSSA" (PDF).
  2. ^ Pesticide Properties Database. "Indaziflam". University of Hertfordshire.
  3. ^ US patent 5169425, Takematsu T.; Hirata T. & Kobayashi I. et al., "Herbicidal compositions comprising 2-Amino-4-Arylalkylamino-6-Haloalkyl-1,3,5-Triazines and Chlorophenoxy Acids and, optionally, substituted ureas", issued 1992-12-08, assigned to Idemitsu Kosan Company Limited 
  4. S2CID 13128483
    .
  5. ^ "Triaziflam (ISO)". chem.nlm.nih.gov. Retrieved 21 March 2021.
  6. ^ WO patent 2004069814, Ahrens H.; Dietrich H. & Minn K. et al., "Amino 1,3,5-Triazines N-substituted with chiral bicyclic radicals", issued 2004-08-19, assigned to Bayer Cropscience GMBH 
  7. ^ a b Meyer, F.; Hanrahan, R.; Michel, J.; Monke, B.; Mudge, L.; Norton, L.; Olsen, C.; Parker, A.; Smith, J.; Spak, D. (2009). Indaziflam/BCS-AA10717-A new herbicide for pre-emergent control of grasses and broadleaf weeds for turf and ornamentals. WSSA Meeting Abstracts.
  8. ^ Mark D. Parrish; R. Darren Unland; William J. Bertges (7–10 December 2009). "Introduction of Indaziflam for Weed Control in Fruit, Nut, and Grape Crops". North Central Weed Science Society Proceedings. 64. Kansas City, Mo: North Central Weed Science Society: 164.
  9. ^ "Bayer CropSciences new herbicide indaziflam received first registration in U.S." Grainews. 6 September 2010. Retrieved 14 March 2021.
  10. S2CID 12250466
    .
  11. ^ a b Weed Science Society of America (3 December 2020). "WSSA-Herbicide Site of Action (SOA) Classification List".
  12. ^ Weed Science Society of America. "Summary of Herbicide Mechanism of Action According to the Weed Science Society of America (WSSA)" (PDF).
  13. Herbicide Resistance Action Committee
    . Retrieved 14 March 2021.
  14. Herbicide Resistance Action Committee
    . Retrieved 14 March 2021.
  15. S2CID 84092985
    .
  16. S2CID 84212641
    .
  17. S2CID 84794877
    .
  18. ^ "Bayer completes sale of its Environmental Science Professional business to Cinven". Envu. Retrieved 11 October 2023.
  19. ^ "Bayer completes sale of its Environmental Science Professional business to Cinven". Bayer Global. Retrieved 11 October 2023.
  20. ^ "Envu's Rejuvra (indaziflam) Herbicide". Envu, formerly Bayer Environmental Science. Retrieved 8 October 2023.
  21. ^ "Esplanade 200 SC IVM Product". Bayer Environmental Science US. Retrieved 14 March 2021.
  22. ^ "Esplanade EZ IVM Product". Bayer Environmental Science US. Retrieved 14 March 2021.
  23. ^ Spesard, Bruce (8 June 2018). "Broadleaf and Grassy Weed Control". Bayer Environmental Science. Retrieved 14 March 2021.
  24. ^ a b "Marengo (indaziflam) or Specticle". Extension Publications. NC State Ag Extension. 30 May 2014. Retrieved 14 March 2021.
  25. ^ "Specticle Flo". Bayer Environmental Science. Retrieved 14 March 2021.
  26. CropScience. Bayer
    . 1 November 2019.
  27. ^ a b "PRIA Label Amendment – IR-4 tolerance petition and related amendments: (R190) to establish new uses on Hops, Caneberry subgroup 13-07A, Coffee, Bushberry subgroup 13-07B, Tropicals 23A and another amendment, and (R175) for crop group conversions in Stone Fruits 12-12 and Tree Nuts 14-12 Product Name: Indaziflam 200 SC Herbicide EPA Registration Number: 264-1106 Petition Number: 6E8452 Application Date: February 18, 2016 Decision Number(s): 514431, 514432, 514435, 514436" (PDF). US EPA. 5 July 2017.
  28. ^ "Indaziflam". PubChem. NCBI, NLM, US NIH. Retrieved 14 March 2021. CID=CID 44146693 from PubChem
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