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Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.
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Names | |
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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) |
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20920435 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.216.692 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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: | |
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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).
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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]
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 Class 29 by the Weed Science Society of America/Herbicide Resistance Action Committee.[11][12]
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]
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]
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]
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