Fenarimol

Last updated
Fenarimol
Fenarimol.svg
Names
IUPAC name
(R/S)-2,4′-Dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol
Other names
α-(2-Chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.056.432 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
    Key: NHOWDZOIZKMVAI-UHFFFAOYSA-N
  • InChI=1/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
    Key: NHOWDZOIZKMVAI-UHFFFAOYAN
  • Clc1ccc(cc1)C(O)(c2ccccc2Cl)c3cncnc3
Properties
C17H12Cl2N2O
Molar mass 331.20 g·mol−1
AppearanceColorless powder with aromatic odor
Melting point 117 to 119 °C (243 to 246 °F; 390 to 392 K) [1]
Boiling point 240 °C (464 °F; 513 K)(decomposition) [1]
13.7 mg/L at 25 °C
Solubility in other solventsSoluble in acetone, xylene and methanol [1]
Vapor pressure 65 μ Pa (25 °C) [1]
Hazards
Lethal dose or concentration (LD, LC):
>2000 mg·kg−1 (oral, Rat) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Fenarimol, sold under the tradenames Bloc, Rimidin and Rubigan, is a fungicide which acts against rusts, blackspot and mildew fungi. It is used on ornamental plants, trees, lawns, tomatoes, peppers, eggplants, cucumbers and melons. It is mainly used to control powdery mildew. It works by inhibiting the fungus's biosynthesis of important steroid molecules (via blockade of the CYP51 enzyme). [2]

Contents

History

Fenarimol was developed by Eli Lilly & Company around 1971. [3]

As of early 2018, derivatives of this compound are being researched in an open source manner for possible treatment of eumycetoma. [4]

Synthesis

Fenarimol is made by the reaction of 2,4'-dichlorobenzophenone with an organolithium pyrimidine made via bromine-lithium exchange. [2]

Fenarimolsynth.svg

Related Research Articles

Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. One of the three diazines, it has the nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine. In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U).

Uracil Chemical compound of RNA

Uracil is one of the four nucleobases in the nucleic acid RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. Uracil is a demethylated form of thymine.

Nucleobase Nitrogen-containing biological compounds that form nucleosides

Nucleobases, also known as nitrogenous bases or often simply bases, are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic building blocks of nucleic acids. The ability of nucleobases to form base pairs and to stack one upon another leads directly to long-chain helical structures such as ribonucleic acid (RNA) and deoxyribonucleic acid (DNA).

Nucleoside Any of several glycosylamines comprising a nucleobase and a sugar molecule

Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase and a five-carbon sugar whereas a nucleotide is composed of a nucleobase, a five-carbon sugar, and one or more phosphate groups. In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or the N1 of a pyrimidine. Nucleotides are the molecular building-blocks of DNA and RNA.

Deoxyuridine Chemical compound

Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as pyrimidine 2′-deoxyribonucleosides and closely resembles the chemical composition of uridine but without the presence of the 2′ hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF3 group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine.

Powdery mildew Fungal plant disease

Powdery mildew is a fungal disease that affects a wide range of plants. Powdery mildew diseases are caused by many different species of fungi in the order Erysiphales. Powdery mildew is one of the easier plant diseases to identify, as its symptoms are quite distinctive. Infected plants display white powdery spots on the leaves and stems. The lower leaves are the most affected, but the mildew can appear on any above-ground part of the plant. As the disease progresses, the spots get larger and denser as large numbers of asexual spores are formed, and the mildew may spread up and down the length of the plant.

Downy mildew Name for several species of fungus

Downy mildew refers to any of several types of oomycete microbes that are obligate parasites of plants. Downy mildews exclusively belong to Peronosporaceae. In commercial agriculture, they are a particular problem for growers of crucifers, grapes and vegetables that grow on vines. The prime example is Peronospora farinosa featured in NCBI-Taxonomy and HYP3. This pathogen does not produce survival structures in the northern states of the United States, and overwinters as live mildew colonies in Gulf Coast states. It progresses northward with cucurbit production each spring. Yield loss associated with downy mildew is most likely related to soft rots that occur after plant canopies collapse and sunburn occurs on fruit. Cucurbit downy mildew only affects leaves of cucurbit plants.

Fungal infection Fungal infection of animals, including humans

Fungal infection, also known as mycosis, is disease caused by fungi. Different types are traditionally divided according to the part of the body affected; superficial, subcutaneous, and systemic. Superficial fungal infections include common tinea of the skin, such as tinea of the body, groin, hands, feet and beard, and yeast infections such as pityriasis versicolor. Subcutaneous types include eumycetoma and chromoblastomycosis, which generally affect tissues in and beneath the skin. Systemic fungal infections are more serious and include cryptococcosis, histoplasmosis, pneumocystis pneumonia, aspergillosis and mucormycosis. Signs and symptoms range widely. There is usually a rash with superficial infection. Fungal infection within the skin or under the skin may present with a lump and skin changes. Pneumonia-like symptoms or meningitis may occur with a deeper or systemic infection.

Eumycetoma Medical condition

Eumycetoma, also known as Madura foot, is a persistent fungal infection of the skin and the tissues just under the skin, affecting most commonly the feet, although it can occur in hands and other body parts. It starts as a painless wet nodule, which may be present for years before ulceration, swelling, grainy discharge and weeping from sinuses and fistulae, followed by bone deformity.

Open research Research made available to the public

Open research is research conducted in the spirit of free and open-source software. Much like open-source schemes that are built around a source code that is made public, the central theme of open research is to make clear accounts of the methodology freely available via the internet, along with any data or results extracted or derived from them. This permits a massively distributed collaboration, and one in which anyone may participate at any level of the project.

Neglected tropical diseases Diverse group of tropical infection diseases which are common in developing countries

Neglected tropical diseases (NTDs) are a diverse group of tropical infections which are common in low-income populations in developing regions of Africa, Asia, and the Americas. They are caused by a variety of pathogens such as viruses, bacteria, protozoa and parasitic worms (helminths). These diseases are contrasted with the big three infectious diseases, which generally receive greater treatment and research funding. In sub-Saharan Africa, the effect of these diseases as a group is comparable to malaria and tuberculosis. NTD co-infection can also make HIV/AIDS and tuberculosis more deadly.

World Christian Encyclopedia is a reference work, with its third edition published by Edinburgh University Press in November 2019. The WCE is known for providing membership statistics for major world religions and Christian denominations including historical data and projections of future populations.

Pirimiphos-methyl Chemical compound

Pirimiphos-methyl, marketed as Actellic, and Sybol is a phosphorothioate used as an insecticide. It was originally developed by Imperial Chemical Industries Ltd., now Syngenta, at their Jealott's Hill site and first marketed in 1977, ten years after its discovery.

Mycetoma is a chronic infection in the skin caused by either bacteria (actinomycetoma) or fungi (eumycetoma), typically resulting in a triad of painless firm skin lumps, the formation of weeping sinuses, and a discharge that contains grains. 80% occur in feet.

ChEMBL Chemical database of bioactive molecules with drug-like properties

ChEMBL or ChEMBLdb is a manually curated chemical database of bioactive molecules with drug-like properties. It is maintained by the European Bioinformatics Institute (EBI), of the European Molecular Biology Laboratory (EMBL), based at the Wellcome Trust Genome Campus, Hinxton, UK.

TDR Targets

The TDR Targets database is a bioinformatics project that seeks to exploit the availability of diverse genomic and chemical datasets to facilitate the identification and prioritization of drugs and drug targets in neglected disease pathogens. TDR in the name of the database stands from the popular abbreviation for a special programme within the World Health Organization, whose focus is Tropical Disease Research. The project was jumpstarted by funds from this programme, and the initial focus of the resource was on organisms/diseases of high priority for this Programme.

Bupirimate Chemical compound

Bupirimate is an active ingredient of plant protection products, which has an effect as a fungicide. It belongs to the chemical family of pyrimidine sulfamates. Bupirimate has translaminar mobility and systemic translocation in the xylem. It acts mainly by inhibiting sporulation and is used for control of powdery mildew of apples, pears, stone fruit, cucurbits, roses and other ornamentals, strawberries, gooseberries, currants, raspberries, hops, beets and other crops. Bupirimate is not an insecticide. It is of low mammalian toxicity and is non-toxic to bees. However, it is used in many products which also contain insecticides.

Cumin Species of plant with seeds used as a spice

Cumin is a flowering plant in the family Apiaceae, native to the Irano-Turanian Region. Its seeds – each one contained within a fruit, which is dried – are used in the cuisines of many cultures in both whole and ground form. Although cumin is thought to have uses in traditional medicine, there is no high-quality evidence that it is safe or effective as a therapeutic agent.

<i>Erysiphe syringae</i> Species of fungus

Powdery mildew of lilac, or Erysiphe syringae is a fungal pathogen of lilacs.

Matthew Houghton Todd is a British chemist and the Professor and Chair of Drug Discovery of the School of Pharmacy at University College London. He is the founder of Open Source Malaria (OSM) and his research focuses on drug discovery and development for this disease. Recently, he has expanded to other areas, particularly neglected diseases such as tuberculosis and mycetoma in the Open Source Tuberculosis (OSTB) and Open Source Mycetoma (MycetOS) project, through a collaboration with the Drugs for Neglected Diseases Initiative and Erasmus MC. In addition, he has some research activity in catalysis and methodology.

References

  1. 1 2 3 4 5 EU-Data.
  2. 1 2 Clayden J, Greeves N, Warren S (2005). Organic chemistry (Reprinted (with corrections) ed.). Oxford [u.a.]: Oxford Univ. Press. pp.  216. ISBN   978-0-19-850346-0.
  3. GB 1218623 "Substituted-5-pyrimidine compounds "
  4. Reynolds, Todd B.; Lim, Wilson; Melse, Youri; Konings, Mickey; Phat Duong, Hung; Eadie, Kimberly; Laleu, Benoît; Perry, Benjamin; Todd, Matthew H.; Ioset, Jean-Robert; van de Sande, Wendy W. J. (2018). "Addressing the most neglected diseases through an open research model: The discovery of fenarimols as novel drug candidates for eumycetoma". PLOS Neglected Tropical Diseases. 12 (4): e0006437. doi: 10.1371/journal.pntd.0006437 . ISSN   1935-2735. PMC   5940239 . PMID   29698504.