Clomazone

Last updated
Clomazone
Clomazon.svg
Clomazone 3D ball.png
Names
Preferred IUPAC name
2-[(2-Chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one
Other names
Dimethazone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.125.682 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C12H14ClNO2/c1-12(2)8-16-14(11(12)15)7-9-5-3-4-6-10(9)13/h3-6H,7-8H2,1-2H3 Yes check.svgY
    Key: KIEDNEWSYUYDSN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H14ClNO2/c1-12(2)8-16-14(11(12)15)7-9-5-3-4-6-10(9)13/h3-6H,7-8H2,1-2H3
    Key: KIEDNEWSYUYDSN-UHFFFAOYAD
  • Clc1ccccc1CN2OCC(C2=O)(C)C
Properties
C12H14ClNO2
Molar mass 239.69806
Appearancewhite solid
Melting point 33.9 °C (93.0 °F; 307.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Clomazone is an agricultural herbicide, and has been the active ingredient of products named "Command" and "Commence". The molecule consists of a 2-chlorobenzyl group bound to a N-O heterocycle called isoxazolidinone. It is a white solid.

Clomazone was first registered by the USEPA on March 8, 1993, and was commercialized by FMC Corporation. It is used for broadleaf weed control in several crops, including soybeans, peas, maize, oilseed rape, sugar cane, cassava, pumpkins and tobacco. [1] It may be applied pre-emergence of incorporated before planting the crop. Clomazone is relatively volatile (vapor pressure is 19.2 mPa) and vapors induce striking visual symptoms on non-target sensitive plants. Clomazone undergoes biological degradation, exhibiting a soil half life of one to four months. [2] Adsorption of the herbicide to soil solids slows degradation and volatilization. [3] Encapsulation helps reduce volatility and therefore reduces off-target damage to sensitive plants. [4]

Clomazone suppresses the biosynthesis of chlorophyll and other plant pigments. [5] [6]

Related Research Articles

Volatilization is the process whereby a dissolved sample is vaporised. In atomic spectroscopy this is usually a two-step process. The analyte is turned into small droplets in a nebuliser which are entrained in a gas flow which is in turn volatilised in a high temperature flame in the case of AAS or volatilised in a gas plasma torch in the case of ICP spectroscopy.

<span class="mw-page-title-main">Herbicide</span> 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 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">Glyphosate</span> Broad-spectrum 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. 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">Cover crop</span> Crop planted to manage erosion and soil quality

In agriculture, cover crops are plants that are planted to cover the soil rather than for the purpose of being harvested. Cover crops manage soil erosion, soil fertility, soil quality, water, weeds, pests, diseases, biodiversity and wildlife in an agroecosystem—an ecological system managed and shaped by humans. Cover crops may be an off-season crop planted after harvesting the cash crop. Cover crops are nurse crops in that they increase the survival of the main crop being harvested, and are often grown over winter. In the United States, cover cropping may cost as much as $35 per acre.

<span class="mw-page-title-main">Mulch</span> Layer of material applied to the surface of soil

A mulch is a layer of material applied to the surface of soil. Reasons for applying mulch include conservation of soil moisture, improving fertility and health of the soil, reducing weed growth and enhancing the visual appeal of the area.

<span class="mw-page-title-main">Plastic mulch</span> Plastic film used in the role of mulch

Plastic mulch is a product used in plasticulture in a similar fashion to mulch, to suppress weeds and conserve water in crop production and landscaping. Certain plastic mulches also act as a barrier to keep methyl bromide, both a powerful fumigant and ozone depleter, in the soil. Crops grow through slits or holes in thin plastic sheeting. Plastic mulch is often used in conjunction with drip irrigation. Some research has been done using different colors of mulch to affect crop growth. Use of plastic mulch is predominant in large-scale vegetable growing, with millions of acres cultivated under plastic mulch worldwide each year.

Microencapsulation is a process in which tiny particles or droplets are surrounded by a coating to give small capsules, with useful properties. In general, it is used to incorporate food ingredients, enzymes, cells or other materials on a micro metric scale. Microencapsulation can also be used to enclose solids, liquids, or gases inside a micrometric wall made of hard or soft soluble film, in order to reduce dosing frequency and prevent the degradation of pharmaceuticals.

<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 crop fields 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">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">Living mulch</span> Cover crop grown with a main crop as mulch

In agriculture, a living mulch is a cover crop interplanted or undersown with a main crop, and intended to serve the purposes of a mulch, such as weed suppression and regulation of soil temperature. Living mulches grow for a long time with the main crops, whereas cover crops are incorporated into the soil or killed with herbicides.

<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">Dimethenamid</span> Chemical compound

Dimethenamid is a widely used herbicide. In 2001, about 7 million pounds (3,200 t) of dimethenamid were used in the United States. Dimethenamid is registered for control of annual grasses, certain annual broadleaf weeds and sedges in field corn, seed corn, popcorn and soybeans. Supplemental labeling also allows use on sweet corn, grain sorghum, dry beans and peanuts. In registering dimethinamide, EPA concluded that the primary means of dissipation of dimethenamid applied to the soil surface is photolysis, whereas below the surface loss was due largely to microbial metabolism. The herbicide was found to undergo anaerobic microbial degradation under denitrifying, iron-reducing, sulfate-reducing, or methanogenic conditions. In that study, more than half of the herbicide carbon added was found to be incorporated irreversibly into soil-bound residue.

<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">Wine chemistry</span> Chemistry of wine

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals.

<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">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">Dazomet</span> Chemical compound

Dazomet is a common soil fumigant that acts as a herbicide, fungicide, slimicide, and nematicide.

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

Fluridone is an organic compound that is used as aquatic herbicide often used to control invasive plants. It is used in the United States to control hydrilla and Eurasian watermilfoil among other species. Fluridone is sold as a solution and as a slow release solid because the herbicide level must be maintained for several weeks. The compound is a colorless solid.

<span class="mw-page-title-main">Cumin</span> Species of plant with seeds used as a spice

Cumin is a flowering plant in the family Apiaceae, native to the Irano-Turanian Region. Its seeds – each one contained within a fruit, which is dried – are used in the cuisines of many cultures in both whole and ground form. Although cumin is used in traditional medicine, there is no high-quality evidence that it is safe or effective as a therapeutic agent.

<span class="mw-page-title-main">Passion fruit (fruit)</span> Fruit of several passion flower species

The passion fruit is the fruit of a number of plants in the genus Passiflora.

References

  1. Tomlin, CD. 1997. The pesticide manual, 11th edition. British Crop Protection Council. Farnham, Surrey, UK. p 256-257. ISBN   978-1901396881.
  2. Mervosh, T. L., G.K. Sims, and E.W. Stoller. 1995. Clomazone fate in soil as affected by microbial activity, temperature, and soil moisture. J. Agric. Food Chem. 43:537-543. https://doi.org/10.1021/jf00050a052.
  3. Mervosh, T. L., G.K. Sims, E.W. Stoller, and T.R. Ellsworth. 1995. Clomazone sorption in soil: Incubation time, temperature, and soil moisture effects. J. Agric. Food Chem. 43:2295-2300. https://doi.org/10.1021/jf00056a062.
  4. Mervosh, T. L., E.W. Stoller, T.R. Ellsworth, and G.K. Sims. 1995. Effects of starch encapsulation on clomazone and atrazine movement in soil and clomazone volatilization. Weed Science. 43:445-453. DOI: https://doi.org/10.1017/S0043174500081455.
  5. Storzer, Werner "The residue behaviour of new herbicides in crop plants" Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 2002, vol. 54, 193-203.
  6. Gara, Pedro M. David; Rosso, Janina A.; Martin, Marcela V.; Bosio, Gabriela N.; Gonzalez, Monica C.; Martire, Daniel O. "Characterization of humic substances and their role in photochemical processes of environmental interest" Trends in Photochemistry & Photobiology 2011, vol. 13, pages 51-70.