Thiophanate-methyl

Last updated
Thiophanate-methyl
Thiophanate Methyl.png
Names
Preferred IUPAC name
Dimethyl N,N′-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamate
Other names
Dimethyl 4,4′-(o-phenylene)bis(3-thioallophanate)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.041.567 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H14N4O4S2/c1-19-11(17)15-9(21)13-7-5-3-4-6-8(7)14-10(22)16-12(18)20-2/h3-6H,1-2H3,(H2,13,15,17,21)(H2,14,16,18,22)
    Key: QGHREAKMXXNCOA-UHFFFAOYSA-N
  • COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
Properties
C12H14N4O4S2
Molar mass 342.39 g·mol−1
Appearancewhite powder
Melting point 172 °C (342 °F; 445 K)
26.6 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thiophanate-methyl is an organic compound with the formula C6H4(NHC(S)NH(CO)OCH3)2. The compound is a colorless or white solid, although commercial samples are generally tan-colored. It is prepared from o-phenylenediamine. It is a widely used fungicide used on tree, vine, and root crops. [1] In Europe it is applied to tomato, wine grapes, beans, wheat, and aubergine. [2]

Methods for its analysis have received considerable attention. [3] [4] [5] It is commonly used to treat botrytis bunch rot and gray mold caused by Botrytis cinerea strawberry in California. [6] Thiophanate-methyl acts as a fungicide via its primary metabolite carbendazim.

Related Research Articles

<i>Botrytis cinerea</i> Species of fungus

Botrytis cinerea is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" or "gray mold".

<span class="mw-page-title-main">Electron ionization</span> Ionization technique

Electron ionization is an ionization method in which energetic electrons interact with solid or gas phase atoms or molecules to produce ions. EI was one of the first ionization techniques developed for mass spectrometry. However, this method is still a popular ionization technique. This technique is considered a hard ionization method, since it uses highly energetic electrons to produce ions. This leads to extensive fragmentation, which can be helpful for structure determination of unknown compounds. EI is the most useful for organic compounds which have a molecular weight below 600 amu. Also, several other thermally stable and volatile compounds in solid, liquid and gas states can be detected with the use of this technique when coupled with various separation methods.

<span class="mw-page-title-main">Ethyl carbamate</span> Chemical compound

Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks.

Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals. Fungicides are also used to control oomycetes, which are not taxonomically/genetically fungi, although sharing similar methods of infecting plants. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward.

<span class="mw-page-title-main">Vinclozolin</span> Fungicide used on fruits and vegetables

Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are Botrytis cinerea and Sclerotinia sclerotiorum. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency. In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects.

<span class="mw-page-title-main">Liquid chromatography–mass spectrometry</span> Analytical chemistry technique

Liquid chromatography–mass spectrometry (LC–MS) is an analytical chemistry technique that combines the physical separation capabilities of liquid chromatography with the mass analysis capabilities of mass spectrometry (MS). Coupled chromatography – MS systems are popular in chemical analysis because the individual capabilities of each technique are enhanced synergistically. While liquid chromatography separates mixtures with multiple components, mass spectrometry provides spectral information that may help to identify each separated component. MS is not only sensitive, but provides selective detection, relieving the need for complete chromatographic separation. LC–MS is also appropriate for metabolomics because of its good coverage of a wide range of chemicals. This tandem technique can be used to analyze biochemical, organic, and inorganic compounds commonly found in complex samples of environmental and biological origin. Therefore, LC–MS may be applied in a wide range of sectors including biotechnology, environment monitoring, food processing, and pharmaceutical, agrochemical, and cosmetic industries. Since the early 2000s, LC–MS has also begun to be used in clinical applications.

<span class="mw-page-title-main">Electroextraction</span>

Electroextraction (EE) is a sample enrichment technique that focuses charged analytes from a large volume of one phase into a small volume of aqueous phase through the application of an electric current. The technique was originally developed as a separation technique for chemical engineering, but has since been coupled to capillary electrophoresis and liquid chromatography–mass spectrometry as a means of improving limits of detection, analysis time, and selectivity. The use of EE-CE has made capillary electrophoresis more applicable to use in the pharmaceutical industry.

<span class="mw-page-title-main">Cytochrome b</span> Membrane protein involved in the electron transport chain

Cytochrome b is a protein found in the membranes of aerobic cells. In eukaryotic mitochondria and in aerobic prokaryotes, cytochrome b is a component of respiratory chain complex III — also known as the bc1 complex or ubiquinol-cytochrome c reductase. In plant chloroplasts and cyanobacteria, there is a homologous protein, cytochrome b6, a component of the plastoquinone-plastocyanin reductase, also known as the b6f complex. These complexes are involved in electron transport, the pumping of protons to create a proton-motive force (PMF). This proton gradient is used for the generation of ATP. These complexes play a vital role in cells.

<span class="mw-page-title-main">Zearalenone</span> Chemical compound

Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species. Specifically, the Gibberella zeae, the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as Fusarium graminearum. Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti, Fusarium verticillioides, and Fusarium incarnatum. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the presence of other toxins.

<span class="mw-page-title-main">ABT-202</span> Chemical compound

ABT-202 is a drug developed by Abbott, which acts as an agonist at neural nicotinic acetylcholine receptors and has been researched for use as an analgesic, although it has not passed clinical trials.

<span class="mw-page-title-main">Yessotoxin</span> Chemical compound

Yessotoxins are a group of lipophilic, sulfur bearing polyether toxins that are related to ciguatoxins. They are produced by a variety of dinoflagellates, most notably Lingulodinium polyedrum and Gonyaulax spinifera.

<i>N</i>-Desalkylflurazepam Benzodiazepine analog

N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.

<span class="mw-page-title-main">Dichlofluanid</span> Chemical compound

Dichlofluanid is a fungicide used to protect strawberries, grapes, berries, apples, pears and other fruit, vegetables and ornamental plants from diseases such as apple scab, black spot, leather rot, gray mold, downy mildew and others caused by the fungi Botrytis, Alternaria, Sclerotinia, and Monilinia. It is also used to protect against diseases of fruit during storage, and as a wood preservative, often as part of a paint undercoat.

<span class="mw-page-title-main">Homosildenafil</span> Chemical compound

Homosildenafil is a synthetic drug which acts as a phosphodiesterase inhibitor. It is an analog of sildenafil and vardenafil. Homosildenafil was first identified as an adulterant in sex enhancement products in 2003 and was more recently detected in dietary supplements.

<span class="mw-page-title-main">Fludioxonil</span> Chemical compound

Fludioxonil is a synthetic phenylpyrrole chemical introduced by Ciba-Geigy in 1993 for use as a non-systemic fungicide. It is a structural analog of the natural fungicide pyrrolnitrin.

4-Ethylamphetamine (4-EA) is a substituted amphetamine derivative which has been sold as a designer drug. It is mainly known as a synthetic intermediate used as a building block to manufacture larger molecules, but 4-EA is closely related in chemical structure to designer drugs such as 4-methylamphetamine and 4-ethylmethcathinone, and is both a synthetic precursor and a metabolite of the 25-NB derivative 4-EA-NBOMe.

<span class="mw-page-title-main">4-Methoxyestriol</span> Chemical compound

4-Methoxyestriol (4-MeO-E3) is an endogenous estrogen metabolite. It is the 4-methyl ether of 4-hydroxyestriol and a metabolite of estriol and 4-hydroxyestriol. 4-Methoxyestriol has very low affinities for the estrogen receptors. Its relative binding affinities (RBAs) for estrogen receptor alpha (ERα) and estrogen receptor beta (ERβ) are both about 1% of those of estradiol. For comparison, estriol had RBAs of 11% and 35%, respectively.

<span class="mw-page-title-main">Pyraclostrobin</span> Agricultural fungicide, QoI, strobilurin

Pyraclostrobin is a quinone outside inhibitor (QoI)-type fungicide used in agriculture. Among the QoIs, it lies within the strobilurin chemical class.

cv. 'Camino Real' is a cultivar of strawberry produced by the Shaw & Larson era of the UC Davis breeding program.

<span class="mw-page-title-main">Strawberry cultivation in California</span>

Strawberries in the United States are almost entirely grown in California – 86% of fresh and 98% of frozen in 2017 – with Florida a distant second. Of that 30.0% was from Monterey, 28.6% from Ventura, 20.0% from Santa Barbara, 10.0% from San Luis Obispo, and 9.2% from Santa Cruz. The Watsonville/Salinas strawberry zone in Santa Cruz/Monterey, and the Oxnard zone in Ventura, contribute heavily to those concentrations.

References

  1. "Thiophanate-methyl" (PDF). Environmental Protection Agency.
  2. European Food Safety Authority; et al. (2018). "Peer review of the pesticide risk assessment of the active substance thiophanate-methyl". EFSA Journal. 16 (1): e05133. doi: 10.2903/j.efsa.2018.5133 . PMC   7009477 . PMID   32625680. S2CID   79538931.
  3. Mol, Hans G. J.; Plaza-Bolaños, Patricia; Zomer, Paul; De Rijk, Theo C.; Stolker, Alida A. M.; Mulder, Patrick P. J. (2008). "Toward a Generic Extraction Method for Simultaneous Determination of Pesticides, Mycotoxins, Plant Toxins, and Veterinary Drugs in Feed and Food Matrixes". Analytical Chemistry. 80 (24): 9450–9459. doi:10.1021/ac801557f. PMID   19072261.
  4. Romero-González, R.; Garrido Frenich, A.; Martínez Vidal, J.L.; Prestes, O.D.; Grio, S.L. (2011). "Simultaneous determination of pesticides, biopesticides and mycotoxins in organic products applying a quick, easy, cheap, effective, rugged and safe extraction procedure and ultra-high performance liquid chromatography–tandem mass spectrometry". Journal of Chromatography A. 1218 (11): 1477–1485. doi:10.1016/j.chroma.2011.01.034. PMID   21292276.
  5. Kiljanek, Tomasz; Niewiadowska, Alicja; Semeniuk, Stanisław; Gaweł, Marta; Borzęcka, Milena; Posyniak, Andrzej (2016). "Multi-residue method for the determination of pesticides and pesticide metabolites in honeybees by liquid and gas chromatography coupled with tandem mass spectrometry—Honeybee poisoning incidents". Journal of Chromatography A. 1435: 100–114. doi:10.1016/j.chroma.2016.01.045. PMID   26830634.