Names | |
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Preferred IUPAC name N-(3,4-Dichlorophenyl)propanamide | |
Other names N-(3,4-Dichlorophenyl)propionamide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.832 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C9H9Cl2NO | |
Molar mass | 218.08 g/mol |
Appearance | White crystalline solid (pure), Brown powder (impure) |
Melting point | 91 to 93 °C (196 to 199 °F; 364 to 366 K) |
225 ppm | |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 1384 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [2] Propanil is said to be in use in approximately 400,000 acres of rice production each year. [3]
The principal mode of propanil's herbicidal action against weeds is inhibition of their photosynthesis and CO2 fixation. Plants photosynthesize in two stages. In stage I photosynthetic reactions capture sunlight energy and yield molecules with high energy content. In stage II these molecules react to capture CO2, yielding carbohydrate precursors. In the stage I reaction a chlorophyll molecule absorbs one photon (light) and loses one electron, starting an electron transport chain reaction leading to the stage II reactions. Propanil inhibits the electron transport chain reaction and its conversion of CO2 to carbohydrate precursors. That inhibits further development of the weed. [4]
Rice is relatively immune to propanil but most weeds are susceptible to it. The reason for the selectivity is that rice contains a high level of the enzyme aryl acylamidase (AAA), which rapidly metabolizes propanil to relatively nontoxic 3,4-dichloroaniline. Susceptible weeds lack the gene(s) coding for the AAA enzyme and thus succumb to propanil. However, intensive use of propanil and natural selection have caused some weeds to become resistant to propanil. [5]
Propanil is made industrially by nitration of 1,2-dichlorobenzene (1) to give 1,2-dichloro-4-nitrobenzene (2), followed by hydrogenation of the nitro group with Raney nickel to give 3,4-dichloroaniline (3). Acylation of the amine with propanoyl chloride yields propanil (4). [6] The resulting product is white or brown crystals. [7]
Propanil was the subject of several patent infringement suits. In one, Monsanto Co. v. Rohm and Haas Co. , [8] the United States Court of Appeals for the Third Circuit held that Monsanto committed fraud on the Patent Office in procuring its patent on propanil.
Monsanto obtained the patent by providing data to the Patent Office showing that propanil "had "unusual and valuable herbicidal activity" and that its activity was "surprising" because "related compounds possess little or no herbicidal efficiency." Monsanto had conducted a number of tests and submitted test data to the Patent Office that indicated that propanil was superior to other similar chemicals, including one chemical that differed from propanil only in eliminating the CH2 group to the left of the CH3 group at the far right of the diagram shown at above right. (The two chemicals are so-called adjacent homologues.)
But Monsanto had withheld data on those tests that showed that other similar compounds also had herbicidal activity similar to that of propanil. The court said that this amounted to a misrepresentation and Monsanto was not entitled to a patent, so that the patent was invalid or unenforceable. In an earlier case, however, a judge had accepted Monsanto's argument that Monsanto "did nothing more than put their best foot forward" with the Patent Office. [9]
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.
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.
Paraquat (trivial name; ), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is an organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. This salt is one of the most widely used herbicides. It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic (lethal) to human beings and animals due to its redox activity, which produces superoxide anions. It has been linked to the development of Parkinson's disease and is banned in several countries.
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.
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.
Chlortoluron or chlorotoluron are the common names for an organic compound of the phenylurea class of herbicides used to control broadleaf and annual grass weeds in cereal crops.
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.
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.
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.
Dithiopyr is a preemergent herbicide for crabgrass control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds. Dithiopyr inhibits root growth of susceptible weeds as well as turf grass and thus should be used only on established turf with a well-developed root system. Its duration of efficacy is approximately 4 months, so lawns should not be reseeded during this time frame following application of the chemical. Dithiopyr acts primarily as a preemergent herbicide but can also be used in early postemergent control of crabgrass.
John E. Franz is an organic chemist who discovered the herbicide glyphosate while working at Monsanto Company in 1970. The chemical became the active ingredient in Roundup, a broad-spectrum, post-emergence herbicide. Franz has earned much acclaim and many rewards for this breakthrough. He also has over 840 patents to his name worldwide.
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.
4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class, and is used to treat an orphan disease, type I tyrosinemia.
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.
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.
Monsanto Co. v. Rohm and Haas Co., 456 F.2d 592, is a 1972 decision of the United States Court of Appeals for the Third Circuit interpreting what conduct amounts to fraudulent procurement of a patent.
Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.
Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO) 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.
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.
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.
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