indaziflam
{{Use dmy dates|date=May 2022}}
{{short description|Preemergent herbicide discovered in 2009}}
{{Chembox
|IUPACName = 2-N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine
|ImageFile = Indaziflam.svg
|Section1 = {{Chembox Identifiers
| CASNo = 950782-86-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M64ZDU291E
| Beilstein = 20920435
| ChEBI = 133237
| ChemSpiderID = 21442049
| PubChem = 44146693
| StdInChI=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
| StdInChIKey = YFONKFDEZLYQDH-BOURZNODSA-N
| SMILES = C[C@H]1CC2=C([C@@H]1NC3=NC(=NC(=N3)N)C(C)F)C=C(C=C2)C
}}
|Section2 = {{Chembox Properties
|C=16|H=20|F=1|N=5
| Density = 1.23 g/mL
| MeltingPtC = 183
| BoilingPt =
| Solubility = 2.8 mg/L (20 °C)
| LogP = 2.8
}}
|Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|373|410}}
| PPhrases = {{P-phrases|260|273|314|391|501}}
}}
}}
Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.
History
In 1991, the Japanese company Idemitsu Kosan filed a patent to 2-amino 6-fluoroalkyl triazine derivatives as herbicides.{{cite patent |country=US |number=5169425 |status=patent |gdate=1992-12-08 |fdate=1991-06-17 |pridate=1990-06-29 |invent1 =Takematsu T. |invent2=Hirata T. |invent3=Kobayashi I. |invent4=Kikkawa N. |title=Herbicidal compositions comprising 2-Amino-4-Arylalkylamino-6-Haloalkyl-1,3,5-Triazines and Chlorophenoxy Acids and, optionally, substituted ureas |assign1=Idemitsu Kosan Company Limited}} One of these compounds was subsequently given the ISO common name triaziflam but had limited success as a commercial herbicide.{{cite journal |doi=10.1515/znc-2001-7-814 |title=Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites |year=2001 |last1=Grossmann |first1=Klaus |last2=Tresch |first2=Stefan |last3=Plath |first3=Peter |journal=Zeitschrift für Naturforschung C |volume=56 |issue=7–8 |pages=559–569 |pmid=11531090 |s2cid=13128483 |doi-access=free }}{{cite web |url=https://chem.nlm.nih.gov/chemidplus/name/triaziflam%20%5Biso%5D |website=chem.nlm.nih.gov |title=Triaziflam (ISO)|access-date=2021-03-21}} 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.{{cite patent |country=WO |number=2004069814 |status=patent |gdate=2004-08-19 |fdate=2004-01-23 |pridate=2003-02-05 |invent1 =Ahrens H. |invent2=Dietrich H. |invent3=Minn K. |invent4=Auler T., Bieringer H., Hills M., Kehne H., Menne H. |title=Amino 1,3,5-Triazines N-substituted with chiral bicyclic radicals |assign1=Bayer Cropscience GMBH}} The compound was first registered for use in the USA in 2010.
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 and proven in 2014. The cellulose biosynthesis inhibitors (CBIs) are identified as Class 29 by the Weed Science Society of America/Herbicide Resistance Action Committee.
Resistance
{{as of|March 2021}} there are no resistant populations known and none for the broader CBI class (discounting quinclorac).
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),
{{cite web |title=Bayer completes sale of its Environmental Science Professional business to Cinven |url=https://www.bayer.com/en/agriculture/environmental-science |website=Bayer Global |access-date=11 October 2023}} including Rejuvra,{{cite web |title=Envu's Rejuvra (indaziflam) Herbicide |url=https://www.us.envu.com/vegetation-management/range-and-pasture/products/rejuvra |website=Envu, formerly Bayer Environmental Science |access-date=8 October 2023}} the Esplanade line (sometimes mixed with diquat dibromide and glyphosate isopropylamine), Marengo, Specticle, and Bayer CropScience (the inventor of the ingredient), like Alion.
Uses
Indaziflam is approved in the United States for hops, Rubus spp., Coffea spp., bushberries, tropical crops, drupes/stone fruit, and tree nuts. It is used as a preemergent.{{cite web | title=Indaziflam | website=PubChem | publisher=NCBI, NLM, US NIH | url=http://pubchem.ncbi.nlm.nih.gov/compound/44146693 | access-date=2021-03-14}} CID={{PubChem|44146693}}
References
{{reflist|refs=
{{cite web | title=Esplanade 200 SC IVM Product | website=Bayer Environmental Science US | url=http://www.environmentalscience.bayer.us/vegetation-management/industrial-vegetation-management/products/esplanade-200-sc | access-date=2021-03-14}}
{{cite web | title=Esplanade EZ IVM Product | website=Bayer Environmental Science US | url=http://www.environmentalscience.bayer.us/vegetation-management/industrial-vegetation-management/products/esplanade-ez | access-date=2021-03-14}}
{{cite web | title=Marengo (indaziflam) or Specticle | website=Extension Publications | publisher=NC State Ag Extension | date=30 May 2014 | url=http://content.ces.ncsu.edu/marengo-indaziflam | access-date=2021-03-14}}
{{cite web | last=Spesard | first=Bruce | title=Broadleaf and Grassy Weed Control | website=Bayer Environmental Science | date=8 June 2018 | url=http://www.environmentalscience.bayer.us/turf-and-ornamentals-management/production-ornamentals/ornamentals-insights/broadleaf-and-grassy-weed-control | access-date=2021-03-14}}
{{cite web | title=Specticle Flo | website=Bayer Environmental Science | url=http://www.environmentalscience.bayer.us/-/media/prfunitedstates/documents/resource-library/product-labels/specticle-flo.ashx | access-date=2021-03-14}}
{{cite web | url=http://wssa.net/wp-content/uploads/WSSA-Herbicide-SOA-20201203.xlsx | title=WSSA-Herbicide Site of Action (SOA) Classification List | date=3 December 2020 | author=Weed Science Society of America}}
{{cite web | url=http://wssa.net/wp-content/uploads/WSSA-Mechanism-of-Action.pdf | title=Summary of Herbicide Mechanism of Action According to the Weed Science Society of America (WSSA) | author=Weed Science Society of America}}
{{cite web | url=http://www3.epa.gov/pesticides/chem_search/ppls/000264-01106-20170705.pdf | publisher=US EPA | title=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 | date=5 July 2017
}}
{{cite web | url=http://www.cropscience.bayer.us/products/herbicides/alion/label-msds | title=US84467332F (170705Fv2) ALION SC 32 FOZ ETL 0119.indd | date=1 November 2019 | website=CropScience | publisher=Bayer}}
{{cite journal|title=Introduction of Indaziflam for Weed Control in Fruit, Nut, and Grape Crops|author1=Mark D. Parrish |author2=R. Darren Unland |author3=William J. Bertges |date=7-10 December 2009|journal=North Central Weed Science Society Proceedings|publisher=North Central Weed Science Society|volume=64|page=164|location=Kansas City, Mo}}
{{cite journal | last1=Brabham | first1=C. | last2=Lei | first2=L. | last3=Gu | first3=Y. | last4=Stork | first4=J. | last5=Barrett | first5=M. | last6=DeBolt | first6=S. | title=Indaziflam Herbicidal Action: A Potent Cellulose Biosynthesis Inhibitor | journal=Plant Physiology| publisher=American Society of Plant Biologists (OUP) | volume=166 | issue=3 | date=30 July 2014 | issn=0032-0889 | doi=10.1104/pp.114.241950 | pages=1177–1185 | pmid=25077797 | pmc=4226351 | s2cid=12250466}}
{{cite web | title=List of Herbicide Resistant Weeds by Herbicide Mode of Action (L/26) | url=http://www.weedscience.org/summary/MOA.aspx?MOAID=19 | website=International Survey of Herbicide Resistant Weeds | publisher=Herbicide Resistance Action Committee | language=en | access-date=2021-03-14}}
{{cite journal | last1=Tresch | first1=Stefan | last2=Grossmann | first2=Klaus | title=Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots | journal=Pesticide Biochemistry and Physiology | publisher=Elsevier | volume=75 | issue=3 | year=2003 | issn=0048-3575 | doi=10.1016/s0048-3575(03)00013-0 | pages=73–78 | bibcode=2003PBioP..75...73T | s2cid=84212641}}
{{cite journal | last1=Tresch | first1=Stefan | last2=Grossmann | first2=Klaus | title=Erratum to "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots" | journal=Pesticide Biochemistry and Physiology | publisher=Elsevier | volume=76 | issue=2 | year=2003 | issn=0048-3575 | doi=10.1016/s0048-3575(03)00064-6 | pages=70–71 | s2cid=84794877| doi-access=free }}
{{cite web | title=Herbicide Resistant Weeds by Individual Herbicide | url=http://www.weedscience.org/summary/ResistByActive.aspx | language=en | website=International Survey of Herbicide Resistant Weeds | publisher=Herbicide Resistance Action Committee | access-date=2021-03-14}}
{{cite journal | last1=Grossmann | first1=Klaus | last2=Kwiatkowski | first2=Jacek | title=The Mechanism of Quinclorac Selectivity in Grasses | journal=Pesticide Biochemistry and Physiology | publisher=Elsevier | volume=66 | issue=2 | year=2000 | issn=0048-3575 | doi=10.1006/pest.1999.2461 | pages=83–91 | bibcode=2000PBioP..66...83G | s2cid=84092985}}
{{cite web | url=http://wssa.net/wp-content/uploads/WSSA-Approved-Chem-Names.pdf | title=Common and chemical names approved by WSSA | author=Weed Science Society of America}}
}}
{{herbicides}}