Names | |
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Preferred IUPAC name 2,4-Dichloro-1-(4-nitrophenoxy)benzene | |
Other names Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.015.824 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties [1] | |
C12H7Cl2NO3 | |
Molar mass | 284.09 g·mol−1 |
Appearance | Colorless, crystalline solid |
Density | 1.80 g/cm3 at 83 °C |
Melting point | 64–71 °C (147–160 °F; 337–344 K)(technical) |
0.7-1.2 mg/L at 22 °C | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Nitrofen is an herbicide of the diphenyl ether class. Because of concerns about its carcinogenicity, the use of nitrofen has been banned in the European Union [2] and in the United States since 1996. [1] [3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.
In 2002, Nitrofen was detected in organic feed, organic eggs, and organic poultry products in Germany prompting a scandal which caused a decline in all organic meat sales in Europe. [4] [5]
Nitrofen is listed as an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans". [6]
Roundup is the brand name of a systemic, broad-spectrum glyphosate-based herbicide originally produced by Monsanto, which Bayer acquired in 2018. Glyphosate is the most widely used herbicide in the United States. As of 2009, sales of Roundup herbicides still represented about 10 percent of Monsanto's revenue despite competition from Chinese producers of other glyphosate-based herbicides. The overall Roundup line of products, which includes genetically modified seeds, represented about half of Monsanto's yearly revenue. The product is marketed to consumers by Scotts Miracle-Gro Company.
Mothballs are small balls of chemical pesticide and deodorant, sometimes used when storing clothing and other articles susceptible to damage from mold or moth larvae.
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. It was discovered to be an herbicide 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.
The nitrite ion has the chemical formula NO−
2. Nitrite is widely used throughout chemical and pharmaceutical industries. Nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite can also refer to organic compounds with the -ONO group, which are esters of nitrous acid.
Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite salt. It is a precursor to a variety of organic compounds, such as pharmaceuticals, dyes, and pesticides, but it is probably best known as a food additive used in processed meats and (in some countries) in fish products.
Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and sometimes incorrectly called benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.
Carbon black is a material produced by the incomplete combustion of heavy petroleum products such as FCC tar, coal tar, ethylene cracking tar, or vegetable matter. Carbon black is a form of paracrystalline carbon that has a high surface-area-to-volume ratio, albeit lower than that of activated carbon. It is dissimilar to soot in its much higher surface-area-to-volume ratio and significantly lower polycyclic aromatic hydrocarbon (PAH) content. However, carbon black is widely used as a model compound for diesel soot for diesel oxidation experiments. Carbon black is mainly used as a reinforcing filler in tires and other rubber products. In plastics, paints, and inks, carbon black is used as a color pigment. It is used in some places, such as the EU, as a food colourant if produced from vegetable matter (E153).
Persistent organic pollutants (POPs), sometimes known as "forever chemicals" are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. Because of their persistence, POPs bioaccumulate with potential adverse impacts on human health and the environment. The effect of POPs on human and environmental health was discussed, with intention to eliminate or severely restrict their production, by the international community at the Stockholm Convention on Persistent Organic Pollutants in 2001.
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also collects and publishes surveillance data regarding the occurrence of cancer worldwide.
Diethyl sulfate (DES) is a highly toxic, combustible, and likely carcinogenic chemical compound with the formula (C2H5)2SO4. It occurs as a colorless, oily liquid with a faint peppermint odor and is corrosive to tissue and metals. Diethyl sulfate is used as an alkylating agent to prepare ethyl derivatives of phenols, amines, and thiols. It is also used as a potent ethylating agent. It is used to manufacture dyes and textiles.
Endosulfan is an off-patent organochlorine insecticide and acaricide that is being phased out globally. The two isomers, endo and exo, are known popularly as I and II. Endosulfan sulfate is a product of oxidation containing one extra O atom attached to the S atom. Endosulfan became a highly controversial agrichemical due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban has taken effect in mid-2012, with certain uses exempted for five additional years. More than 80 countries, including the European Union, Australia, New Zealand, several West African nations, the United States, Brazil, and Canada had already banned it or announced phase-outs by the time the Stockholm Convention ban was agreed upon. It is still used extensively in India, China despite laws banning it, and few other countries. It is produced by Makhteshim Agan and several manufacturers in India and China. Although, the Supreme Court had, by an order dated 13.05.2011, put a ban on the production and sale of endosulfan in India till further orders.
Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. Chlorothalonil-containing products are sold under the names Bravo, Echo, and Daconil. It was first registered for use in the US in 1966. In 1997, the most recent year for which data are available, it was the third most used fungicide in the US, behind only sulfur and copper, with 12 million pounds used in agriculture that year. Including nonagricultural uses, the United States Environmental Protection Agency (EPA) estimates, on average, almost 15 million lb (6.8 million kg) were used annually from 1990 to 1996.
Hexachlorobenzene, or perchlorobenzene, is an organochloride with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.
Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of Mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.
Organic food is food produced by methods complying with the standards of organic farming. Standards vary worldwide, but organic farming features practices that cycle resources, promote ecological balance, and conserve biodiversity. Organizations regulating organic products may restrict the use of certain pesticides and fertilizers in the farming methods used to produce such products. Organic foods typically are not processed using irradiation, industrial solvents, or synthetic food additives.
Chlorobenzilate is a pesticide that is not currently used in the United States or Europe. It was originally developed by Ciba-Geigy and introduced in 1952. It was used as an acaricide against mites on citrus trees, including deciduous fruit trees. It has been detected as a residue on tomatoes found in Japanese markets in 2005. It is a non-systemic pesticide that works through contact and as a neurotoxin: it disrupts the functioning of the nervous system.
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 selectively kills most broadleaf weeds by causing uncontrolled growth in them but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.
Glyphosate-based herbicides are usually made of a glyphosate salt that is combined with other ingredients that are needed to stabilize the herbicide formula and allow penetration into plants. The glyphosate-based herbicide Roundup was first developed by Monsanto in the 1970s. It is used most heavily on corn, soy, and cotton crops that have been genetically modified to be resistant to the herbicide. Some products include two active ingredients, such as Enlist Duo which includes 2,4-D as well as glyphosate. As of 2010, more than 750 glyphosate products were on the market. The names of inert ingredients used in glyphosate formulations are usually not listed on the product labels.
Fomesafen 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 fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.
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.