Names | |
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Preferred IUPAC name 2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-N-[methyl(propan-2-yl)sulfamoyl]benzamide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.124.700 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties [1] | |
C17H17ClF4N4O5S | |
Molar mass | 500.85 g·mol−1 |
Density | 1.595 g/mL |
Melting point | 189.9 °C (373.8 °F; 463.0 K) |
2100 mg/L (20 °C) | |
Hazards [2] | |
GHS labelling: | |
Warning | |
H410 | |
P273, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Saflufenacil is the ISO common name [3] for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf weeds in crops including soybeans and corn.
In 1985, chemists at the Dr R. Maag subsidiary of Hoffmann-La Roche filed patents to 3-aryl uracil derivatives which had herbicidal activity. [4] The work was continued by Ciba-Geigy and further patents claiming additional esters were published, including to butafenacil (CGA276854), which was marketed in 2001. [5] [6] BASF scientists investigated the chemistry and patented an analog where the carboxylic ester of butafenacil was replaced by a sulfamoyl carboxamide. It was developed under the code number BAS800H and first marketed in 2008 with the brand name Kixor. [7] [1]
As described in the BASF patent, the key step in the preparation of saflufenacil involved the reaction between a substituted aniline and an oxazinone. 2-chloro-4-fluoro-5-aminobenzoic acid and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one were heated in acetic acid to form the ring systems of the herbicide in over 90% yield, with further standard chemical transformations to generate the final product. [7]
Saflufenacil works by inhibiting protoporphyrinogen IX oxidase (PPO), preventing chlorophyll formation, and resulting in accumulation of protoporphyrin IX which is a potent photosensitizer. This activates oxygen, causing lipid peroxidation with rapid loss of membrane integrity and function. The effects visible on whole plants are chlorosis and necrosis. [8] In corn and some varieties of soyabean the effects are insufficient to cause serious damage, leading to useful selectivity. [9] [10]
Saflufenacil is registered for use in the United States, where the Environmental Protection Agency (EPA) is responsible for regulating pesticides under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), the Food Quality Protection Act (FQPA) and the Pesticide Registration Improvement Act (PRIA). A pesticide can only be used legally according to the directions on the label that is included at the time of the sale. [9] [11]
The herbicide controls only broadleaf weeds but is effective both pre- and post-emergence on a very wide range of these species including Abutilon theophrasti , Acalypha virginica , Acanthospermum hispidum , Amaranthus hybridus , Amaranthus palmeri , Amaranthus powellii , Amaranthus retroflexus , Ambrosia artemisiifolia , Chenopodium album , Conyza canadensis , Datura stramonium , Galinsoga parviflora , Helianthus annuus , Hibiscus trionum , Ipomoea hederacea , Ipomoea purpurea , Kochia scoparia , Mollugo verticillata , Physalis angulata , Polygonum convolvulus , Polygonum persicaria , Portulaca oleracea , Richardia scabra , Salsola kali , Sicyos angulatus , Sinapis arvensis , Solanum nigrum , Stellaria media , Thlaspi arvense , Tribulus terrestris and Xanthium strumarium . The product is typically used at application rates of 0.1 lb a.i. per acre and may also be applied for crop desiccation pre-harvest. [9]
The estimated annual use of saflufenacil in US agriculture is mapped by the US Geological Service and shows that in 2018, the latest date for which figures are available, approximately 600,000 pounds (270,000 kg) were applied — mainly in corn and soybean. [12] The compound is also registered for use in Australia but not in the European Union. [1]
Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.
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.
Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the PPOX gene.
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."
Acibenzolar-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.
Dichlorprop is a chlorophenoxy herbicide similar in structure to 2,4-D that is used to kill annual and perennial broadleaf weeds. It is a component of many common weedkillers. About 4 million pounds of dichlorprop are used annually in the United States.
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.
Dimethenamid is a widely used herbicide belonging to the chloroacetamide class. Group 15 herbicides inhibit synthesis of certain long-chain fatty acids, thus reducing plant growth. 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.
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.
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.
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.
Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.
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.
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.
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.