Chlorsulfuron

Last updated
Chlorsulfuron
Chlorosulfuron 200.svg
Names
Preferred IUPAC name
2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzene-1-sulfonamide
Other names
DPX4189
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.059.316 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 265-268-5
KEGG
PubChem CID
UNII
UN number 3077 2588
  • InChI=1S/C12H12ClN5O4S/c1-7-14-10(17-12(15-7)22-2)16-11(19)18-23(20,21)9-6-4-3-5-8(9)13/h3-6H,1-2H3,(H2,14,15,16,17,18,19) Yes check.svgY
    Key: VJYIFXVZLXQVHO-UHFFFAOYSA-N Yes check.svgY
  • O=C(NC1=NC(=NC(=N1)C)OC)NS(=O)(=O)C=2C=CC=CC2Cl
Properties [1]
C12H12ClN5O4S
Molar mass 357.78
AppearanceWhite crystalline solid
Density 1.48 g/cm3
Melting point 173 °C (343 °F; 446 K)
12500 mg/L (20 °C)
log P -0.99
Acidity (pKa)3.4
Hazards [2]
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorsulfuron is an ALS (acetolactate synthase) inhibitor herbicide, and is a sulfonylurea compound. [3] [4] It was discovered by George Levitt in February 1976 while working at DuPont, which was the patent assignee. [5] [6] [7]

Contents

Brand names

Originally introduced in 1982 under the brand name Glean by DuPont, [1] [7] later also as Telar, [3] in North America.

Chemistry

The first synthesis of chlorsulfuron was disclosed in a patent filed by the American chemical company DuPont in 1977. 2-Chlorobenzenesulfonyl isocyanate was condensed with 2-amino-4-methoxy-6-methyl-1,3,5-triazine to form the sulfonylurea product. [6]

Chlorsulfuron synthesis.svg

Mode of action

Chlorsulfuron is an herbicide of the acetolactate synthase inhibitor (ALS inhibitor) class, HRAC (Herbicide Resistance Action Committee) group 2 [4] [3] (legacy HRAC Group B). [4]

Efficacy

Triticum aestivum is naturally resistant via aryl hydroxylation then conjugation with glucose compounds into non-herbicidal conjugates. [8] Widespread weed resistance to chlorsulfuron has been found across North America and around the world. T. aestivum's close relative Lolium rigidum was found to be using the same mechanism by Christopher et al 1991 and Cotterman & Saari 1992. [8] A North American population of Stellaria media was found by Hall and Devine 1990 to be resistant by way of an ALS target mutation rather than by improved disposal. [8] Increased P450 activity can also be effective, such as in Alopecurus myosuroides (found by Letouzé and Gasquez 2003), and L. rigidum (by Tardif and Powles 1999). [9] Another such mechanism - the acetolactate synthase target-site mutation Pro-197–Ser - was found by Roux et al 2004 to be accompanied by a 37% recessive fitness cost in a model ( Arabidopsis thaliana ). [10]

Use in genetic engineering

Genes conveying resistance to chlorsulfuron are used as selectable markers when attempting transformation with other genes, [11] [12] for example in Dianthus caryophyllus [11] and Marchantia polymorpha . [12]

Crops have also been deliberately made resistant, for example in maize/corn by McCabe et al 1988 using bombardment with the relevant gene attached to tungsten particles. [13]

Applications

US Geological Survey estimate of chlorsulfuron use in the USA to 2017 Chlorsulfuron usage USA.png
US Geological Survey estimate of chlorsulfuron use in the USA to 2017

Chlorsulfuron 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. Its properties mean that it can be applied to soil so emerging weeds take it up and are controlled. Alternatively, spraying after weeds are already present in the crop will also lead to control. The product is used at application rates of 0.008–0.0155 pounds per acre (9.0–17.4 g/ha). [14] The estimated use in US agriculture is mapped by the US Geological Service and shows that from 1992 to 2017, the latest date for which figures are available, up to 120,000 pounds (54,000 kg) were applied each year. The compound is used mainly in wheat but also in pasture. [15]

Chlorsulfuron is recommended alone or with aminocyclopyrachlor for control of Centaurea solstitialis , Centaurea calcitrapa , and Centaurea iberica in the Pacific Northwest of North America. [3]

Related Research Articles

<span class="mw-page-title-main">Herbicide</span> Type of 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 (sometimes called total weed killers kill plants indiscriminately. Due to herbicide resistance – a major concern in agriculture – a number of products combine herbicides with different means of action. Integrated pest management may use herbicides alongside other pest control methods.

<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">Glyphosate</span> Systemic herbicide and crop desiccant

Glyphosate is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.

<span class="mw-page-title-main">Sulfonylurea</span> Class of organic compounds used in medicine and agriculture

Sulfonylureas or sulphonylureas are a class of organic compounds used in medicine and agriculture. The functional group consists of a sulfonyl group (-S(=O)2) with its sulphur atom bonded to a nitrogen atom of a ureylene group (N,N-dehydrourea, a dehydrogenated derivative of urea). The side chains R1 and R2 distinguish various sulfonylureas. Sulfonylureas are the most widely used herbicide.

<i>Centaurea calcitrapa</i> Species of flowering plant

Centaurea calcitrapa is a species of flowering plant known by several common names, including red star-thistle and purple star thistle. It is native to Europe but is rarely found there, it is known across the globe as an introduced species and often a noxious weed. The species name calcitrapa comes from the word caltrop, a type of weapon covered in sharp spikes.

<i>Centaurea solstitialis</i> Species of flowering plant

Centaurea solstitialis, the yellow star-thistle, is a species of thorny plant in the genus Centaurea, which is part of the family Asteraceae. A winter annual, it is native to the Mediterranean Basin region and invasive in many other places. It is also known as golden starthistle, yellow cockspur and St. Barnaby's thistle.

<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">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.

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

Propanil is a widely used contact herbicide. With an estimated use of about 8 million pounds in 2001, it is one of the more widely used herbicides in the United States. Propanil is said to be in use in approximately 400,000 acres of rice production each year.

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

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.

<span class="mw-page-title-main">EPSP synthase</span> Enzyme produced by plants and microorganisms

5-enolpyruvylshikimate-3-phosphate (EPSP) synthase is an enzyme produced by plants and microorganisms. EPSPS catalyzes the chemical reaction:

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">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.

The agricultural weed syndrome is the set of common traits which make a plant a successful agricultural weed. Most of these traits are not, themselves, phenotypes but are instead methods of rapid adaptation. So equipped, plants of various origins - invasives, natives, mildly successful marginal weeds of agriculture, weeds of other settings - accumulate other characteristics which allow them to compete in an environment with a high degree of human management.

<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">Halosulfuron-methyl</span> Chemical compound

Halosulfuron-methyl is a sulfonylurea post-emergence herbicide used to control some annual and perennial broad-leaved weeds and sedges in a range of crops, established landscape woody ornamentals and turfgrass. It is marketed under several tradenames including Sedgehammer and Sandea.

References

  1. 1 2 Pesticide Properties Database. "Chlorsulfuron". University of Hertfordshire.
  2. PubChem Database. "Chlorsulfuron".
  3. 1 2 3 4 "Starthistle, yellow (Centaurea solstitialis), purple (Centaurea calcitrapa), and Iberian (Centaurea iberica)". Pacific Northwest Pest Management Handbooks. Pacific Northwest Extension (Oregon, Washington, Idaho). 2015-11-10. Retrieved 2021-03-03.
  4. 1 2 3 "HRAC MOA 2020 Revision Description and Master Herbicide List". Herbicide Resistance Action Committee . 2020-09-14. Retrieved 2021-04-01.
  5. DE 2715786,George Levitt,"Herbicidal sulfonamides",issued 1977, assigned to E. I. du Pont de Nemours and Company
  6. 1 2 US 4127405,George Levitt,"Herbicidal sulfonamides",issued 1978, assigned to E. I. du Pont de Nemours and Company
  7. 1 2 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.
  8. 1 2 3 Holt, Jodie S.; Powles, Steven B.; Holtum, Joseph A. M. (1993). "Mechanisms and Agronomic Aspects of Herbicide Resistance". Annual Review of Plant Physiology and Plant Molecular Biology . Annual Reviews. 44 (1): 203–229. doi:10.1146/annurev.pp.44.060193.001223. ISSN   1040-2519.
  9. Powles, Stephen B.; Yu, Qin (2010-06-02). "Evolution in Action: Plants Resistant to Herbicides". Annual Review of Plant Biology . Annual Reviews. 61 (1): 317–347. doi:10.1146/annurev-arplant-042809-112119. ISSN   1543-5008. PMID   20192743.
  10. Vila-Aiub, M M; Neve, P; Roux, F (2011-05-04). "A unified approach to the estimation and interpretation of resistance costs in plants". Heredity . The Genetics Society (Nature). 107 (5): 386–394. doi:10.1038/hdy.2011.29. ISSN   0018-067X. PMC   3199924 . PMID   21540885.
  11. 1 2 Tanaka, Yoshikazu; Brugliera, Filippa (2013-02-19). "Flower colour and cytochromes P450". Philosophical Transactions of the Royal Society B: Biological Sciences . The Royal Society. 368 (1612): 20120432. doi:10.1098/rstb.2012.0432. ISSN   0962-8436. PMC   3538422 . PMID   23297355.
  12. 1 2 Kohchi, Takayuki; Yamato, Katsuyuki T.; Ishizaki, Kimitsune; Yamaoka, Shohei; Nishihama, Ryuichi (2021-06-17). "Development and Molecular Genetics of Marchantia polymorpha". Annual Review of Plant Biology . Annual Reviews. 72 (1): 677–702. doi:10.1146/annurev-arplant-082520-094256. ISSN   1543-5008. PMID   33684298. S2CID   232159593.
  13. Klein, Theodore M.; Arentzen, Rene; Lewis, Paul A.; Fitzpatrick-McElligott, Sandra (1992). "Transformation of Microbes, Plants and Animals by Particle Bombardment". Nature Biotechnology . Nature Portfolio. 10 (3): 286–291. doi:10.1038/nbt0392-286. ISSN   1087-0156. PMID   1368100. S2CID   26707595.
  14. FMC Corporation (2019). "Glean XP herbicide US label" (PDF).
  15. US Geological Survey. "Estimated Agricultural Use for chlorsulfuron, 2017" . Retrieved 2021-09-28.