Chlortoluron

Last updated
Chlortoluron
Chlortoluron.svg
Chlortoluron 3D ball.png
Names
Preferred IUPAC name
N′-(3-Chloro-4-methylphenyl)-N,N-dimethylurea
Other names
3-(3-Chloro-4-methylphenyl)-1,1-dimethylurea
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.035.978 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 239-592-2
PubChem CID
UNII
  • InChI=1S/C10H13ClN2O/c1-7-4-5-8(6-9(7)11)12-10(14)13(2)3/h4-6H,1-3H3,(H,12,14) Yes check.svgY
    Key: JXCGFZXSOMJFOA-UHFFFAOYSA-N Yes check.svgY
  • Clc1cc(NC(=O)N(C)C)ccc1C
Properties [1]
C10H13ClN2O
Molar mass 212.67602
Melting point 148 °C (298 °F; 421 K)
log P 2.41
Hazards [2]
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H351, H361d, H410
P201, P202, P273, P281, P308+P313, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlortoluron or chlorotoluron are the common names [3] for an organic compound of the phenylurea class of herbicides used to control broadleaf and annual grass weeds in cereal crops.

Contents

History

In 1952, chemists at E. I. du Pont de Nemours and Company patented a series of aryl urea derivatives as herbicides. Several compounds covered by this patent were commercialized as herbicides: monuron (4-chlorophenyl), diuron (3,4-dichlorophenyl) and chlortoluron, the 3-chloro-4-methylphenyl example. [4] [5] Subsequently, over thirty related urea analogs with the same mechanism of action reached the market worldwide. [6]

Synthesis

As described in the du Pont patent, the starting material is a substituted aryl amine, an aniline, which is treated with phosgene to form its isocyanate derivative. This is subsequently reacted with dimethylamine to give the final product. [4]

Aryl-NH2 + COCl2 → Aryl-NCO
Aryl-NCO + NH(CH3)2 → Aryl-NHCON(CH3)2

Mechanism of action

The phenylurea class of herbicides including chlortoluron are inhibitors of photosynthesis. They block the QB plastoquinone binding site of photosystem II, preventing electron flow from QA to QB. [7] This interrupts the photosynthetic electron transport chain and kills the plant. [8]

Usage

Chlortoluron was first licensed for use in the European Union in 1994 [9] and this has been extended, currently until October 2021. [10] It is now mainly used in mixture with other herbicides including diflufenican and pendimethalin. [11]

It can be used to control broadleaf weeds and grasses including Alopecurus myosuroides , Anthemis arvensis , Atriplex prostrata , Calendula spp. , Convolvulaceae spp. , Galeopsis spp. , Lamium spp. , Papaver rhoeas , Paspalum distichum , Poa annua , Solanaceae spp. , Stellaria media and Veronica spp. It is mainly used in cereal crops including wheat and barley. [9] [11]

Related Research Articles

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

MCPA is a widely used phenoxy herbicide introduced in 1945. It selectively controls broad-leaf weeds in pasture and cereal crops. The mode of action of MCPA is as an auxin, which are growth hormones that naturally exist in plants.

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

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

<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">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.

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

Fenoprop, also called 2,4,5-TP, is the organic compound 2-(2,4,5-trichlorophenoxy)propionic acid. It is a phenoxy herbicide and a plant growth regulator, an analog of 2,4,5-T in which the latter's acetic acid sidechain is replaced with a propionate group (with an extra CH3). The addition of this extra methyl group creates a chiral centre in the molecule and useful biological activity is found only in the (2R)-isomer. The compound's mechanism of action is to mimic the auxin growth hormone indoleacetic acid (IAA). When sprayed on plants it induces rapid, uncontrolled growth. As with 2,4,5-T, fenoprop is toxic to shrubs and trees.

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

Sulfentrazone is the ISO common name for an organic compound used as a broad-spectrum herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase. It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.

<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">Monolinuron</span> Chemical compound

Monolinuron is a pesticide, more specifically a selective systemic herbicide and an algaecide. As an herbicide, it is used to control broad-leaved weeds and annual grasses in vegetable crops such as leeks, potatoes, and dwarf French beans. Monolinuron affects the photosynthesis in weeds. Following uptake of monolinuron through roots and leaves of weeds, monolinuron causes early symptoms of yellowing and die-back of the leaves, eventually resulting in weed death. In fishkeeping, it is used to control blanket weed and hair algae.

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

Saflufenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf weeds in crops including soybeans and corn.

<span class="mw-page-title-main">2,4-Dichlorophenoxyacetic acid</span> Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula C8H6Cl2O3 which is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide which kills most broadleaf weeds by causing uncontrolled growth in them but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

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

Acifluorfen 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 acifluorfen and its salts, via metabolic disposal by glutathione S-transferase. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.

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

Aminocyclopyrachlor is a selective, low-toxicity herbicide that provides pre- and post-emergent control of broadleaf weeds, woody species, vines and grasses on several non-food use sites, such as rights of way, wildlife management areas, recreational areas, turf/lawns, golf courses and sod farms. It was conditionally registered as Imprelis by DuPont in August 2010, and first used in Fall 2010. The chemical is a systemic herbicide and acts by disrupting gene expression. This causes undifferentiated cell division and elongation.

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

Bifenox 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.

<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">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">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">Butafenacil</span> Chemical compound

Butafenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf and some grass weeds in crops including cereals and canola.

<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. EPA Comptox database. "Chlorotoluron". comptox.epa.gov. Retrieved 2021-03-26.
  2. PubChem database. "Chlorotoluron". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-03-27.
  3. "Compendium of Pesticide Common Names". alanwood.net.
  4. 1 2 USpatent 2655445,Todd C.W.,"3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same",issued 1953-10-13, assigned to E. I. du Pont de Nemours & Co.
  5. Liu, Jing (2010). "Phenylurea Herbicides". Hayes' Handbook of Pesticide Toxicology. pp. 1725–1731. doi:10.1016/B978-0-12-374367-1.00080-X. ISBN   9780123743671.
  6. "Urea herbicides". alanwood.net. Retrieved 2021-03-26.
  7. Broser, Matthias; Glöckner, Carina; Gabdulkhakov, Azat; Guskov, Albert; Buchta, Joachim; Kern, Jan; Müh, Frank; Dau, Holger; Saenger, Wolfram; Zouni, Athina (2011). "Structural Basis of Cyanobacterial Photosystem II Inhibition by the Herbicide Terbutryn". Journal of Biological Chemistry. 286 (18): 15964–15972. doi: 10.1074/jbc.M110.215970 . PMC   3091205 . PMID   21367867.
  8. Oettmeier, Walter (1992). "Herbicides of photosystem II". The Photosystems. pp. 349–408. doi:10.1016/B978-0-444-89440-3.50018-7. ISBN   9780444894403.
  9. 1 2 Pesticide Properties Database. "Chlorotoluron". University of Hertfordshire. Retrieved 2021-03-27.
  10. "Commission implementing regulation (EU) 2020/1511". 2020-10-16. Retrieved 2021-03-27.
  11. 1 2 Adama (2017). "Tower" (PDF). pcs.agriculture.gov.ie. Archived from the original (PDF) on 2021-11-14. Retrieved 2021-03-27.