Monolinuron

Last updated
Monolinuron
Monolinuron.svg
Monolinuron-3D-balls.png
Names
Preferred IUPAC name
N′-(4-Chlorophenyl)-N-methoxy-N-methylurea
Identifiers
3D model (JSmol)
2212523
ChemSpider
ECHA InfoCard 100.015.572 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-129-5
KEGG
MeSH Monolinuron
PubChem CID
RTECS number
  • YS6425000
UNII
  • InChI=1S/C9H11ClN2O2/c1-12(14-2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13) Yes check.svgY
    Key: LKJPSUCKSLORMF-UHFFFAOYSA-N Yes check.svgY
  • Clc1ccc(NC(=O)N(OC)C)cc1
Properties
C9H11ClN2O2
Molar mass 214.65 g·mol−1
Melting point 80 to 83 °C (176 to 181 °F; 353 to 356 K)
0.735 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Monolinuron is a pesticide, [1] more specifically a selective systemic herbicide [2] and an algaecide. [3] As an herbicide, it is used to control broad-leaved weeds and annual grasses in vegetable crops such as leeks, potatoes, [2] and dwarf French beans. [4] 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. [4] In fishkeeping, it is used to control blanket weed and hair algae. [3]

As a herbicide, it is used in a range of food and non-food crops, e.g. beans and other vegetables, onions, fruits, cereals, potatoes, vines and ornamental plants. It was introduced to use in circa 1965. It is an inhibitor of photosystem II of photosynthesis. It is a derivative of urea and related to paraquat. It is available under various trade names including Monamex, Gramonol, and Aresin. [5]

It is soluble in water (0.735 g/L), and very soluble in organic solvents (200 g/L in acetone, methanol, and toluene, 3.9 g/L in hexane). Its volatility is low and its leachability is high. It is moderately persistent and moderately mobile in soil, stable in water, and fast degraded in water sediments (DT50 of 22 days). It has low toxicity for mammals (LD50 oral for a rat is 2100 mg/kg). [5]

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 3x to 6x from 1900 to 2000.

<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">Alachlor</span> Chemical compound; herbicide

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.

<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">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">Dicamba</span> Chemical compound used as herbicide

Dicamba is a selective systemic herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid. It has been described as a "widely used, low-cost, environmentally friendly herbicide that does not persist in soils and shows little or no toxicity to wildlife and humans."

<span class="mw-page-title-main">2,6-Dichlorobenzonitrile</span> Chemical compound

2,6-Dichlorobenzonitrile (DCBN or dichlobenil) is an organic compound with the chemical formula C6H3Cl2CN. It is a white solid that is soluble in organic solvents. It is widely used as a herbicide and organic chemistry building block.

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

Aminopyralid is a selective herbicide used for control of broadleaf weeds, especially thistles and clovers. It is in the picolinic acid family of herbicides, which also includes clopyralid, picloram, triclopyr, and several less common herbicides. It was first registered for use in 2005, in the USA under the brand name "Milestone" and later under various names starting with "Grazon". In the UK it is sold under the brand names Banish, Forefront, Halcyon, Pharaoh, Pro-Banish, Runway, Synero, and Upfront.

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

Bensulide is a selective organophosphate herbicide. It is one of a few organophosphate compounds that are used as an herbicide. Most of the others are used as insecticides. It is used on vegetable crops such as carrots, cucumbers, peppers, and melons and in cotton and turfgrass to control annual grasses such as bluegrass and crabgrass and broadleaf weeds. It is often applied before the weed seeds germinate (pre-emergence) in order to prevent them from germinating. It is available as granules or an emulsifiable concentrate. Estimates place the total use of bensulide in the United States at about 632,000 pounds annually. Application rates may be relatively heavy when it is used. The EPA classifies bensulide as a general use pesticide.

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

Lactofen is a complex ester of acifluorfen and is a nitrophenyl ether selective herbicide and fungicide. It is used in postemergence applications to certain crops which are resistant to its action. The name "Lactofen" is approved by the American National Standards Institute and the Weed Science Society of America, and is also approved in China (乳氟禾草灵).

<span class="mw-page-title-main">Organic beans</span>

Organic beans are produced and processed without the use of synthetic fertilizers and pesticides. In 2008, over 2,600,000 acres (11,000 km2) of cropland were certified organic in the United States. Dry beans, snap beans, and soybeans were grown on 16,000 acres (65 km2), 5,200 acres (21 km2), and 98,000 acres (400 km2), respectively.

<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">2,4-Dichlorophenoxyacetic acid</span> Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

<span class="mw-page-title-main">Crop desiccation</span>

Pre-harvest crop desiccation refers to the application of an agent to a crop just before harvest to kill the leaves and/or plants so that the crop dries out from environmental conditions, or "dry-down", more quickly and evenly. In agriculture, the term desiccant is applied to an agent that promotes dry down, thus the agents used are not chemical desiccants, rather they are herbicides and/or defoliants used to artificially accelerate the drying of plant tissues. Desiccation of crops through the use of herbicides is practiced worldwide on a variety of food and non-food crops.

<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">Butamifos</span> Chemical compound

Butamifos is an herbicide that is used to control weeds.

<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.

References

  1. Rossoff, Irving S. (2002). Encyclopedia of clinical toxicology. p. 718.
  2. 1 2 Milne, George W. A. (2005). Gardner's commercially important chemicals. p. 44.
  3. 1 2 "Pesticides: HSE registered products". Archived from the original on 2009-07-24. Retrieved 2009-07-31.
  4. 1 2 "Department for Environment, Food and Rural Affairs, Evaluation of Fully Approved or Provisionally Approved Products, Evaluation on: Monolinuron, May 1995" (PDF). Retrieved 2011-08-19.
  5. 1 2 "Monolinuron (Ref: HOE 002747)".