Indaziflam

Last updated

Indaziflam
Indaziflam.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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.

Contents

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 Class 29 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]

Related Research Articles

<span class="mw-page-title-main">Herbicide</span> Chemical used to kill unwanted plants

Herbicides, also commonly known as weed killers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides can be used to clear waste ground, industrial and construction sites, railways and railway embankments as they kill all plant material with which they come into contact. Apart from selective/non-selective, other important distinctions include persistence, means of uptake, and mechanism of action. Historically, products such as common salt and other metal salts were used as herbicides, however, these have gradually fallen out of favor, and in some countries, a number of these are banned due to their persistence in soil, and toxicity and groundwater contamination concerns. Herbicides have also been used in warfare and conflict.

<span class="mw-page-title-main">Pesticide resistance</span> Decreased effectiveness of a pesticide on a pest

Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then that will reduce the pesticide's efficacy – efficacy and resistance are inversely related.

<span class="mw-page-title-main">Weed control</span> Botanical component of pest control for plants

Weed control is a type of pest control, which attempts to stop or reduce growth of weeds, especially noxious weeds, with the aim of reducing their competition with desired flora and fauna including domesticated plants and livestock, and in natural settings preventing non native species competing with native species.

<span class="mw-page-title-main">Hexazinone</span> Chemical compound

Hexazinone is an organic compound that is used as a broad spectrum herbicide. It is a colorless solid. It exhibits some solubility in water but is highly soluble in most organic solvents except alkanes. A member of the triazine class herbicides, it is manufactured by DuPont and sold under the trade name Velpar.

<span class="mw-page-title-main">Phenoxy herbicide</span> Class of herbicide

Phenoxy herbicides are two families of chemicals that have been developed as commercially important herbicides, widely used in agriculture. They share the part structure of phenoxyacetic acid.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

<span class="mw-page-title-main">Pendimethalin</span> Chemical compound

Pendimethalin is an herbicide of the dinitroaniline class used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals, corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

Dicamba is a broad-spectrum herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid.

<span class="mw-page-title-main">Dithiopyr</span> Chemical compound

Dithiopyr is a preemergent herbicide for crabgrass control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds. Dithiopyr inhibits root growth of susceptible weeds as well as turf grass and thus should be used only on established turf with a well-developed root system. Its duration of efficacy is approximately 4 months, so lawns should not be reseeded during this time frame following application of the chemical. Dithiopyr acts primarily as a preemergent herbicide but can also be used in early postemergent control of crabgrass.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

Mesotrione is the ISO common name for an organic compound that is used as a selective herbicide, especially in maize. A synthetic inspired by the natural substance leptospermone, it inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class, and is used to treat an orphan disease, type I tyrosinemia.

<span class="mw-page-title-main">Quinclorac</span> Herbicide, synthetix auxin

Quinclorac is a selective herbicide used primarily to control weeds in rice crops, but is also used on other agricultural crops and is found in some household herbicides for lawn use. Most lawn maintenance companies use the product for the control of annual grass weeds like crabgrass.

<span class="mw-page-title-main">Weed science</span>

Weed science is a scientific discipline concerned with plants that may be considered weeds, their effects on human activities, and their management "a branch of applied ecology that attempts to modify the environment against natural evolutionary trends.".

<span class="mw-page-title-main">Cyanazine</span> Chemical compound

Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.

<span class="mw-page-title-main">Fomesafen</span> PPOi herbicide

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO) which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.

<span class="mw-page-title-main">Fluazifop</span> ACCase herbicide, fop, anti-grass

Fluazifop is the common name used by the ISO for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.

<span class="mw-page-title-main">Aclonifen</span> Chemical compound

Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

<span class="mw-page-title-main">Sethoxydim</span> Chemical compound

Sethoxydim is a postemergent herbicide for control of grass weeds in a wide variety of horticultural crops.

<span class="mw-page-title-main">Tribenuron</span> Chemical compound

Tribenuron in the form of tribenuron-methyl is a sulfonylurea herbicide. Its mode of action is the inhibition of acetolactate synthase, group 2 of the Herbicide Resistance Action Committee's classification scheme.

<span class="mw-page-title-main">Chlorsulfuron</span> ALS inhibitor herbicide

Chlorsulfuron is an ALS inhibitor herbicide, and is a sulfonylurea compound. It was discovered by George Levitt in February 1976 while working at DuPont, which was the patent assignee.

References

  1. Weed Science Society of America. "Common and chemical names approved by WSSA" (PDF).
  2. Pesticide Properties Database. "Indaziflam". University of Hertfordshire.
  3. USpatent 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. Grossmann, Klaus; Tresch, Stefan; Plath, Peter (2001). "Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites". Zeitschrift für Naturforschung C. 56 (7–8): 559–569. doi: 10.1515/znc-2001-7-814 . PMID   11531090. S2CID   13128483.
  5. "Triaziflam (ISO)". chem.nlm.nih.gov. Retrieved 21 March 2021.
  6. WOpatent 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. 1 2 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. Kansas City, Mo: North Central Weed Science Society. 64: 164.
  9. "Bayer CropSciences new herbicide indaziflam received first registration in U.S." Grainews. 6 September 2010. Retrieved 14 March 2021.
  10. Brabham, C.; Lei, L.; Gu, Y.; Stork, J.; Barrett, M.; DeBolt, S. (30 July 2014). "Indaziflam Herbicidal Action: A Potent Cellulose Biosynthesis Inhibitor". Plant Physiology . American Society of Plant Biologists (OUP). 166 (3): 1177–1185. doi:10.1104/pp.114.241950. ISSN   0032-0889. PMC   4226351 . PMID   25077797. S2CID   12250466.
  11. 1 2 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 Resistant Weeds by Individual Herbicide". International Survey of Herbicide Resistant Weeds. Herbicide Resistance Action Committee . Retrieved 14 March 2021.
  14. "List of Herbicide Resistant Weeds by Herbicide Mode of Action (L/26)". International Survey of Herbicide Resistant Weeds. Herbicide Resistance Action Committee . Retrieved 14 March 2021.
  15. Grossmann, Klaus; Kwiatkowski, Jacek (2000). "The Mechanism of Quinclorac Selectivity in Grasses". Pesticide Biochemistry and Physiology . Elsevier. 66 (2): 83–91. doi:10.1006/pest.1999.2461. ISSN   0048-3575. S2CID   84092985.
  16. Tresch, Stefan; Grossmann, Klaus (2003). "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots". Pesticide Biochemistry and Physiology . Elsevier. 75 (3): 73–78. doi:10.1016/s0048-3575(03)00013-0. ISSN   0048-3575. S2CID   84212641.
  17. Tresch, Stefan; Grossmann, Klaus (2003). "Erratum to "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots"". Pesticide Biochemistry and Physiology . Elsevier. 76 (2): 70–71. doi: 10.1016/s0048-3575(03)00064-6 . ISSN   0048-3575. 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. 1 2 "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. "US84467332F (170705Fv2) ALION SC 32 FOZ ETL 0119.indd". CropScience . Bayer. 1 November 2019.
  27. 1 2 "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