Sulfentrazone
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Sulfentrazone is the
ISO ISO is the most common abbreviation for the International Organization for Standardization. ISO or Iso may also refer to: Business and finance * Iso (supermarket), a chain of Danish supermarkets incorporated into the SuperBest chain in 2007 * Iso ...
common name In biology, a common name of a taxon or organism (also known as a vernacular name, English name, colloquial name, country name, popular name, or farmer's name) is a name that is based on the normal language of everyday life; and is often contrast ...
for an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
used as a broad-spectrum
herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page fo ...
. It acts by inhibiting the enzyme
protoporphyrinogen oxidase Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the ''PPOX'' gene. Protoporphyrinogen oxidase is responsible for the seventh step in biosynthesis of protoporphyrin IX. This porphyrin is the precursor to hemoglobin, ...
. It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.


History

In 1985, scientists at FMC Corporation filed patents on a new class of herbicides containing a triazolinone ring. Sulfentrazone was subsequently developed for market under the code number F6285, with first sales in 1991 and achieving registration in the US in 1997, branded Authority. Other compounds now in the triazolinone class include amicarbazone and carfentrazone.


Mechanism of action

The effects visible on whole plants are chlorosis and
desiccation Desiccation () is the state of extreme dryness, or the process of extreme drying. A desiccant is a hygroscopic (attracts and holds water) substance that induces or sustains such a state in its local vicinity in a moderately sealed container. ...
caused by the inhibition of the enzyme protoporphyrinogen oxidase, which leads to an accumulation of protoporphyrin IX in the plant cells. This is a potent photosensitizer which activates oxygen, leading to
lipid peroxidation Lipid peroxidation is the chain of reactions of oxidative degradation of lipids. It is the process in which radical (chemistry), free radicals "steal" electrons from the lipids in cell membranes, resulting in cell damage. This process proceeds by ...
. Both light and oxygen are required for this process to kill the plant.


Usage

In the
United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...
, the
Environmental Protection Agency A biophysical environment is a biotic and abiotic surrounding of an organism or population, and consequently includes the factors that have an influence in their survival, development, and evolution. A biophysical environment can vary in scale f ...
(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 of the pesticide. The purpose of the label is "to provide clear directions for effective product performance while minimizing risks to human health and the environment". A label is a legally binding document that mandates how the pesticide can and must be used and failure to follow the label as written when using the pesticide is a federal offence. The label includes use for removal of sedges and newly emerged broadleaf weeds including purple and yellow
nutsedge ''Cyperus'' is a large genus of about 700 species of sedges, distributed throughout all continents in both tropical and temperate regions. Description They are annual or perennial plants, mostly aquatic and growing in still or slow-moving w ...
, ''
Kyllinga ''Kyllinga'' is genus of flowering plants in the sedge family known commonly as spikesedges. They are native to tropical and warm temperate areas of the world, especially tropical Africa. These sedges vary in morphology, growing to heights from ...
'', plantain,
clover Clover or trefoil are common names for plants of the genus ''Trifolium'' (from Latin ''tres'' 'three' + ''folium'' 'leaf'), consisting of about 300 species of flowering plants in the legume or pea family Fabaceae originating in Europe. The genus ...
,
spurge ''Euphorbia'' is a very large and diverse genus of flowering plants, commonly called spurge, in the family Euphorbiaceae. "Euphorbia" is sometimes used in ordinary English to collectively refer to all members of Euphorbiaceae (in deference to t ...
, woodsorrel,
knotweed Knotweed is a common name for plants in several genera in the family Polygonaceae. Knotweed may refer to: * ''Fallopia'' * ''Persicaria'' * ''Polygonum'' * ''Reynoutria japonica ''Reynoutria japonica'', synonyms ''Fallopia japonica'' and ''Poly ...
, chickweed, curly dock,
wild onion Wild onion can refer to * any uncultivated species in the genus ''Allium'', especially: **''Allium bisceptrum'' ** ''Allium canadense'' ** ''Allium tricoccum'' ** ''Allium validum'' ** ''Allium vineale'' * ''Asphodelus tenuifolius'' * ''Cyperus bulb ...
, and
wild garlic Plant species in the genus ''Allium'' known as wild garlic include the following: *''Allium canadense'', wild onion *'' Allium carinatum'', keeled garlic *'' Allium drummondii'', Drummond's onion *''Allium ochotense'', Siberian onion *'' Allium ole ...
. It is also effective on many grasses including '' Poa annua'', '' Poa trivialis'',
creeping bentgrass ''Agrostis stolonifera'' (creeping bentgrass, creeping bent, fiorin, spreading bent or carpet bentgrass) is a perennial grass species in the family Poaceae. Description ''Agrostis stolonifera'' is stoloniferous and may form mats or tufts. The ...
, fine & tall
fescue ''Festuca'' (fescue) is a genus of flowering plants belonging to the grass family Poaceae (subfamily Pooideae). They are evergreen or herbaceous perennial tufted grasses with a height range of and a cosmopolitan distribution, occurring on every ...
, perennial ryegrass, Kentucky & rough bluegrass,
bahiagrass ''Paspalum notatum'', known commonly as bahiagrass, common bahia, and Pensacola bahia, is a tropical to subtropical perennial grass (family Poaceae). It is known for its prominent V-shaped inflorescence consisting of two spike-like racemes contai ...
, Bermuda grass, buffalograss, carpetgrass, centipedegrass, kikuyugrass, seashore paspalum,
St. Augustine grass St. Augustine grass (''Stenotaphrum secundatum''), also known as buffalo turf in Australia and buffalo grass in South Africa, is a species of grass in the family Poaceae. It is a warm-season lawn grass that is popular for cultivation in tropical ...
, and zoysiagrass. Sulfentrazone can be used both pre- and post-emergence and is rapidly metabolised by soybean at the
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
group of the triazolinone ring, which confers a level of safety to that crop. The estimated annual use of sulfentrazone in US agriculture is mapped by the US Geological Service and shows that in 2017, the latest date for which figures are available, approximately were applied — mainly in soybean. The compound is not registered for use in the
European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been des ...
, although another triazolinone, carfentrazone-ethyl, is available there. Sulfentrazone also has uses outside agriculture: it controls vegetation on roadside verges and railroads. The active ingredient has been sold alone or in combination with other herbicides under a large number of brand names including Dismiss, Solitaire and Spartan. Suppliers and brand names in the United States are listed in the National Pesticide Information Retrieval System.


Human safety

The LD50 of sulfentrazone is more than 2800 mg/kg (rats, oral), which means that it is of low toxicity by oral ingestion. The US Code of Federal Regulations records the maximum residue tolerances in various food products.


References


External links

* {{Herbicides PPO herbicides Organofluorides Sulfonamides Chloroarenes