Chlortoluron

Last updated
Chlortoluron
Chlortoluron.svg
Chlortoluron 3D ball.png
Names
Preferred IUPAC name
N′-(3-Chloro-4-methylphenyl)-N,N-dimethylurea
Other names
CTU, chlorotoluron, 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, chlorotoluron and CTU 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]

Chlortoluron entered the British market in 1971, alongside isoproturon. CTU was more effective against black-grass, though suffered greater herbicide resistance, so by the 1980s isoproturon overtook it in popularity. Both saw large use as British agriculture was then moving towards earlier sowing, to reduce damage to soil structure, by sowing at drier times. Chlortoluron and isoproturon were useful to control blackgrass while growing winter wheat. [7]

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. [8] This interrupts the photosynthetic electron transport chain and kills the plant. [9]

Chlortoluron is in the Group C, (Australia), C2 (global), Group 7, (numeric), herbicide resistance class. [10]

Usage

Chlortoluron was first licensed for use in the European Union in 1994 [10] and this has been extended, currently until October 2021. [11] It is now mainly used in mixture with other herbicides including diflufenican and pendimethalin. [12]

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. [10] [12]

United Kingdom

Chlorotoluron was banned in the UK in 2010, but in 2014 was reapproved after new formulations came with lower application rates, 250 g/Ha down from (up to) 3500 g/Ha, though farmers must spray it earlier in weeds' growth cycles. Agform did this at the same time to the previously banned isoproturon; both reregistrations are mixes with diflufenican, chlorotoluron's Tower® also contains pendimethalin. [13]

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 kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by three to six times from 1900 to 2000.

<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">DCMU</span> Chemical compound

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

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

Pendimethalin is an herbicide of the dinitroaniline class used premergently and postemergently to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is a 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, and nuts, plus lawns and ornamental plants.

<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">Trifluralin</span> Weed control herbicide

Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia, and New Zealand, previously in the EU. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.

<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">Benfluralin</span> Chemical compound

Benfluralin is a herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development, same as trifluralin, from which benfluralin was developed in 1963.

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

Aminocyclopyrachlor (AMCP) is a selective, low-toxicity, auxin-mimicking herbicide that provides pre- and post-emergent control of broadleaf weeds on several non-food use sites including 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. Aminocyclopyrachlor belongs to the pyrimidine carboxylic acid chemical family and mimics auxin which is a growth-regulating hormone in dicots including broadleaf terrestrial plants. This causes undifferentiated cell division and elongation, with resulting appearance characteristic of auxin herbicide damage such as leaf twisting and curling.

<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.

<span class="mw-page-title-main">Diflufenican</span> Weed control herbicide

Diflufenican is a herbicide used to control weeds including wild radish and wild turnip weeds or suppress capeweed, crassula, marshmallow or shepherd's purse, in clover pasture, lupins, lentils or field peas. It has seen use in Australia, Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn.

<span class="mw-page-title-main">Isoproturon</span> Weed control herbicide

Isoproturon (IPU) is a urea class selective herbicide, which has been used to control annual grasses and many broad leafed weeds in wheat, barley, rye and triticale.

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

Difenoxuron is a phenylurea herbicide used to control annual broad-leaved weeds and grasses in allium crops, carrots, jojoba, and celery.

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. "Isoproturon – the great soil improver | NIAB". www.niab.com. 18 Nov 2016.
  8. 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.
  9. Oettmeier, Walter (1992). "Herbicides of photosystem II". The Photosystems. pp. 349–408. doi:10.1016/B978-0-444-89440-3.50018-7. ISBN   9780444894403.
  10. 1 2 3 Pesticide Properties Database. "Chlorotoluron". University of Hertfordshire. Retrieved 2021-03-27.
  11. "Commission implementing regulation (EU) 2020/1511". 2020-10-16. Retrieved 2021-03-27.
  12. 1 2 Adama (2017). "Tower" (PDF). pcs.agriculture.gov.ie. Archived from the original (PDF) on 2021-11-14. Retrieved 2021-03-27.
  13. "How agchem firms are breathing new life into old pesticide actives". Farmers Weekly. 15 September 2015.