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) | |
20920435 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.216.692 |
PubChem CID | |
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: | |
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.
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]
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 kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by 3x to 6x from 1900 to 2000.
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.
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.
Alachlor is an herbicide from the chloroacetanilide family. It is an odorless, white solid. The greatest use of alachlor is for control of annual grasses and broadleaf weeds in crops. Use of alachlor is illegal in the European Union and no products containing alachlor are currently registered in the United States.
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.
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.
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.
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.
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.
Mesotrione is a selective herbicide used mainly in maize crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. 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.
Quinclorac is an organic compound with the formula C9NH4Cl2CO2H. A colorless solid, it is soluble in hydrocarbons and alcohols. The compound is the carboxylic acid of 3,7-dichloroquinoline.
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.".
Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a 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.
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.
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.
Sethoxydim is a postemergent herbicide for control of grass weeds in a wide variety of horticultural crops.
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.
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.