Indaziflam

Preemergent herbicide discovered in 2009 From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
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).
Close

History

In 1991, the Japanese company Idemitsu Kosan filed a patent to 2-amino 6-fluoroalkyl triazine derivatives as herbicides.[3] One of these compounds was subsequently given the ISO common name triaziflam but had limited success as a commercial herbicide.[4][5] 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 inhibitor of cellulose biosynthesis. This mechanism of action was theorized to be responsible for indaziflam's effect in 2009[7] and proven in 2014.[10] The cellulose biosynthesis inhibitors (CBIs) are identified as Group 29 (Aus: Group O, WSSA: Group L) by the Weed Science Society of America/Herbicide Resistance Action Committee.[11][12]

Resistance

As of March 2021 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] [19] including Rejuvra,[20] the Esplanade[21] line (sometimes mixed with diquat dibromide and glyphosate isopropylamine),[22] Marengo,[23][24] Specticle,[25][24] and Bayer CropScience (the inventor of the ingredient), like Alion.[26]

Uses

Indaziflam is approved in the United States for hops, Rubus spp., Coffea spp., bushberries, tropical crops, drupes/stone fruit, and tree nuts.[27] It is used as a preemergent.[28][27]

References

Related Articles

Wikiwand AI