Sulfentrazone
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Sulfentrazone is the
ISO The International Organization for Standardization (ISO ; ; ) is an independent, non-governmental, international standard development organization composed of representatives from the national standards organizations of member countries. Me ...
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 con ...
for an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
used as a broad-spectrum
herbicide Herbicides (, ), also commonly known as weed killers, 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 f ...
. It acts by inhibiting the enzyme protoporphyrinogen oxidase. It was first marketed in the US in 1997 by FMC Corporation with the
brand name A brand is a name, term, design, symbol or any other feature that distinguishes one seller's goods or service from those of other sellers. Brands are used in business, marketing, and advertising for recognition and, importantly, to create and ...
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 In botany, chlorosis is a condition in which leaves produce insufficient chlorophyll. As chlorophyll is responsible for the green color of leaves, chlorotic leaves are pale, yellow, or yellow-white. The affected plant has little or no ability to ...
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. The ...
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 Photosensitizers are light absorbers that alter the course of a photochemical reaction. They usually are catalysts. They can function by many mechanisms; sometimes they abstract an electron from the substrate, and sometimes they abstract a hydro ...
which activates oxygen, leading to
lipid peroxidation Lipid peroxidation, or lipid oxidation, is a complex chemical process that leads to oxidative degradation of lipids, resulting in the formation of peroxide and hydroperoxide derivatives.{{Cite journal , last1=Ayala , first1=Antonio , last2=Muñoz ...
. Both light and oxygen are required for this process to kill the plant.


Usage

In the
United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
, the Environmental Protection Agency (EPA) is responsible for regulating pesticides under the
Federal Insecticide, Fungicide, and Rodenticide Act The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) is a United States federal law that set up the basic U.S. system of pesticide regulation to protect applicators, consumers, and the environment. It is administered and regulated by t ...
(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 The Cyperaceae () are a family of graminoid (grass-like), monocotyledonous flowering plants known as sedges. The family is large; botanists have described some 5,500 known species in about 90 generathe largest being the "true sedges" (genu ...
and newly emerged broadleaf weeds including purple and yellow nutsedge, '' Kyllinga'', plantain,
clover Clovers, also called trefoils, are plants of the genus ''Trifolium'' (), consisting of about 300 species of flowering plants in the legume family Fabaceae originating in Europe. The genus has a cosmopolitan distribution with the highest diversit ...
, spurge, woodsorrel, knotweed,
chickweed ''Stellaria media'', chickweed, is an annual flowering plant in the family Caryophyllaceae. It is native to Eurasia and naturalized throughout the world, where it is a weed of waste ground, farmland and gardens. It is sometimes grown as a salad ...
, curly dock, wild onion, and
wild garlic Plant species in the genus ''Allium ''Allium'' is a large genus of monocotyledonous flowering plants with around 1000 accepted species, making ''Allium'' the largest genus in the family Amaryllidaceae and among the largest plant genera in the wo ...
. It is also effective on many grasses including '' Poa annua'', '' Poa trivialis'', creeping bentgrass, 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,
Bermuda grass ''Cynodon dactylon'', commonly known as Bermuda grass, also known as couch grass in Australia and New Zealand, is a grass found worldwide. It is native to Europe, Africa, Australia and much of Asia. It has been introduced to the Americas. Contra ...
, buffalograss, carpetgrass, centipedegrass, kikuyugrass, seashore paspalum, St. Augustine grass, and
zoysia ''Zoysia'' (;"Zoysia."
entry at CollinsDictionary.com. Retrieved 5 September 2021.
, -, ...
grass. 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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
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 union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...
, 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 An active ingredient is any ingredient that provides biologically active or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease or to affect the structure or any function of the body of humans or animals. ...
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 Group 14 herbicides