Tribenuron

Last updated
Tribenuron methyl
Tribenuron methyl.svg
Names
IUPAC name
Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-methylcarbamoyl]sulfamoyl]benzoate
Other names
DPX L5300
Identifiers
3D model (JSmol)
ECHA InfoCard 100.100.313 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC
Properties [1]
C15H17N5O6S
Molar mass 395.39 g·mol−1
AppearanceWhite to off-white solid
Density 1.46 g/cm3
Melting point 142
2483 mg/L (20 °C)
log P 0.38
Acidity (pKa)4.65
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tribenuron in the form of tribenuron-methyl is a sulfonylurea herbicide. [2] Its mode of action is the inhibition of acetolactate synthase, group 2 of the Herbicide Resistance Action Committee's classification scheme. [3] [4]

Contents

Chemistry

In the 1970s, chemists at DuPont worked extensively on sulfonylurea herbicides, following the invention of this class of herbicides by George Levitt which had led to the commercialisation of chlorsulfuron. [5] Tribenuron (the carboxylic acid) and its methyl ester [6] were first disclosed in general terms in one of Levitt's patents [7] and subsequently the ester was subject to further patenting [8] and selected for development under the code name DPX L5300. [1] In the final step of its synthesis, 2-methoxycarbonylbenzenesulfonyl isocyanate was condensed with 2-methylamino-4-methoxy-6-methyl-1,3,5-triazine to form the sulfonylurea product. [8]

Tribenuron synthesis.svg

Mode of action

Tribenuron is an herbicide that acts as an acetolactate synthase inhibitor. [2] [3] For the purposes of herbicide resistance management, the Herbicide Resistance Action Committee has placed it in group 2 (legacy HRAC Group B). [4]

Applications

US Geological Survey estimate of tribenuron methyl use in the USA to 2018 Tribenuron usage USA.png
US Geological Survey estimate of tribenuron methyl use in the USA to 2018

Tribenuron has a broad spectrum of activity on commercially important broadleaf weeds and grasses but at the recommended use rate it is safe to important crops such as wheat. When introduced by DuPont, its recommended application rate was 0.015–0.03 pounds per acre (17–34 g/ha). [9] The estimated use in US agriculture is mapped by the US Geological Service and shows that from 1992 to 2018, up to 120,000 pounds (54,000 kg) were applied each year. The compound is used mainly in wheat but also in pasture. [10]

Physicochemistry

In a clay-water suspension, tribenuron has increased sorption with decreasing pH and even more so with suspended load. [11]

Resistant crops

A tribenuron-resistance transformation has been achieved in watermelon and validated by survival of the als mutants but not the controls, under tribenuron treatment. [12]

Two oilseed type sunflower cultivars have been produced by USDA-ARS by conventional breeding. [13]

Related Research Articles

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

Herbicides, also commonly known as weedkillers, 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 the pesticide lacks 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">MCPA</span> Organic compound used as an herbicide

MCPA is a powerful, selective, widely used phenoxy herbicide. The pure compound is a brown-colored powder. MCPA has been extensively used in agriculture to control broad-leaf weeds as a growth regulator primarily in pasture and cereal crops field since 1945. The mode of action of MCPA is as an auxin, which are growth hormones that naturally exist in plants. Overdose application of MCPA acts as an herbicide and results in abnormal growth.

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

Chlortoluron or chlorotoluron are the common names for an organic compound of the phenylurea class of herbicides used to control broadleaf and annual grass weeds in cereal crops.

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

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">DCMU</span> Chemical compound

DCMU is an algicide and herbicide of the arylurea class that inhibits photosynthesis. It was introduced by Bayer in 1954 under the trade name of Diuron.

A mode of action (MoA) describes a functional or anatomical change, resulting from the exposure of a living organism to a substance. In comparison, a mechanism of action (MOA) describes such changes at the molecular level.

<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">Acetolactate synthase</span> Class of enzymes

The acetolactate synthase (ALS) enzyme is a protein found in plants and micro-organisms. ALS catalyzes the first step in the synthesis of the branched-chain amino acids.

<i>Orobanche aegyptiaca</i> Species of flowering plant

Orobanche aegyptiaca, the Egyptian broomrape, is a plant which is an obligate holoparasite from the family Orobanchaceae with a complex lifecycle. This parasite is most common in the Middle East and has a wide host range including many economically important crops.

<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">Imazaquin</span> Chemical compound

Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan.

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

Flazasulfuron is an organic compound that is used as a herbicide. It is classified as a sulfonylurea, because it contains that functional group. The mode of action of flazasulfuron is the inhibition of the enzyme acetolactate synthase (ALS), which results in the inhibition of amino acid synthesis, cell division and ultimately plant growth. Flazasulfuron can be used on both pre-emergent weeds and post-emergent weeds. Growth ceases within hours of the application of the compound. Symptoms include leaf discolouration, desiccation, necrosis and ultimately plant death within 20 – 25 days of application. It is a white, water-soluble solid.

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

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase 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 ISO common name 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">Indaziflam</span> Preemergent herbicide discovered in 2009

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

<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">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. 1 2 Pesticide Properties Database. "Tribenuron-methyl". University of Hertfordshire.
  2. 1 2 Herbicide Resistance Action Committee (HRAC) (2 June 2020). "Global HRAC MOA Classification Working Group Report" (PDF).
  3. 1 2 Scott Senseman (3 December 2020). "Weed Science Society of America - Herbicide Site of Action (SOA) Classification List".
  4. 1 2 "Herbicide Classification Master: March 11, 2020". Herbicide Resistance Action Committee (HRAC). 11 March 2020.
  5. Bhardwaj, Gaurab (2007). "From Pioneering Invention to Sustained Innovation: The Story of Sulfonylurea Herbicides" (PDF). Chemical Heritage NewsMagazine. 25 (1). Archived from the original (PDF) on 2006-11-18.
  6. Weed Science Society of America (WSSA) (2014). "Common and Chemical Names of Herbicides Approved by the Weed Science Society of America". Weed Science . Cambridge University Press (CUP). 62 (4): 679–687. doi:10.1614/0043-1745-62.4.679. ISSN   0043-1745. S2CID   198130304.
  7. USpatent 4383113,George Levitt,"Agricultural sulfonamides",issued 1983-05-10, assigned to E. I. du Pont de Nemours and Company
  8. 1 2 USpatent 4740234,Gerald E. Lepone,"Herbicidal ortho-carbomethoxysulfonylureas",issued 1988-04-26, assigned to E. I. du Pont de Nemours and Company
  9. DuPont (2004). "DuPont Tribenuron Methyl 50SG" (PDF).
  10. US Geological Survey. "Estimated Agricultural Use for tribenuron methyl, 2018" . Retrieved 2023-01-13.
  11. Salbu, Brit; Steinnes, Eiliv (1992). "Applications of nuclear analytical techniques in environmental research. Plenary lecture". The Analyst . Royal Society of Chemistry (RSC). 117 (3): 243–9. Bibcode:1992Ana...117..243S. doi:10.1039/an9921700243. ISSN   0003-2654. PMID   1580364. p. 248.
  12. Wang, Tian; Zhang, Hongyan; Zhu, Hongliang (2019-06-15). "CRISPR technology is revolutionizing the improvement of tomato and other fruit crops". Horticulture Research . Nature Research. 6 (1): 77. doi:10.1038/s41438-019-0159-x. ISSN   2052-7276. PMC   6570646 . PMID   31240102.
  13. Miller, J.F.; Al‐Khatib, Kassim (2004). "Registration of Two Oilseed Sunflower Genetic Stocks, SURES‐1 and SURES‐2 Resistant to Tribenuron Herbicide". Crop Science . Crop Science Society of America (Wiley). 44 (3): 1037–1038. doi:10.2135/cropsci2004.1037. ISSN   0011-183X. S2CID   85001003.

Further reading