Famoxadone

Last updated
Famoxadone
Famoxadone.svg
Names
IUPAC name
(RS)-5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione
Other names
Famoxate; FMX
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.114.714 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3 Yes check.svgY
    Key: PCCSBWNGDMYFCW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3
    Key: PCCSBWNGDMYFCW-UHFFFAOYAG
  • O=C2OC(C(=O)N2Nc1ccccc1)(c4ccc(Oc3ccccc3)cc4)C
Properties
C22H18N2O4
Molar mass 374.396 g·mol−1
Melting point 140.3-141.8 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Famoxadone is a fungicide to protect agricultural products against various fungal diseases on fruiting vegetables, tomatoes, potatoes, curcurbits, lettuce and grapes. [1] It is used in combination with cymoxanil. [1] [2] Famoxadone is a QoI, albeit with a chemistry different from most QoIs. (It is an oxazolidine-dione while most are strobilurins.) [3] [4] [5] It is commonly used against Plasmopara viticola , [3] Alternaria solani , [3] [4] Phytophthora infestans , [3] [4] and Septoria nodorum . [3] [4]

Contents

Molecular interaction

Famoxadone is of lesser interaction strength at the Qp pocket than some other QoIs, for example, azoxystrobin. This is because azoxystrobin and such interact more centrally in the Qp pocket than does famoxadone. [6]

Resistance management

Although it has a different chemistry, famoxadone shows full cross-resistance with the rest of the main FRAC group 11 [4] that it belongs to, which is almost entirely strobs. It has not shown cross-resistance with the 11A subgroup however. As with all QoIs there is a high risk of resistance development and so pesticide stewardship is important. [5] [4]

Populations of P. infestans and A. solani in northern and western Europe are not known to be resistant to famoxadone. [4]

Great Britain approval withdrawn

On June 30 2024, approval for famoxadone's use in Great Britain was withdrawn by the Health and Safety Executive due to the risk it presents to birds. [7] Its use was already banned in the European Union, and there was in 2024 concern about the levels of allowed residue particularly on table grapes being too high. [8]

Related Research Articles

Q<sub>o</sub>I Kind of chemicals used to kill fungus

Qo inhibitors (QoI), or quinone outside inhibitors, are a group of fungicides used in agriculture. Some of these fungicides are among the most popular in the world. QoI are chemical compounds which act at the quinol outer binding site of the cytochrome bc1 complex.

<i>Phytophthora infestans</i> Species of single-celled organism

Phytophthora infestans is an oomycete or water mold, a fungus-like microorganism that causes the serious potato and tomato disease known as late blight or potato blight. Early blight, caused by Alternaria solani, is also often called "potato blight". Late blight was a major culprit in the 1840s European, the 1845–1852 Irish, and the 1846 Highland potato famines. The organism can also infect some other members of the Solanaceae. The pathogen is favored by moist, cool environments: sporulation is optimal at 12–18 °C (54–64 °F) in water-saturated or nearly saturated environments, and zoospore production is favored at temperatures below 15 °C (59 °F). Lesion growth rates are typically optimal at a slightly warmer temperature range of 20 to 24 °C.

<span class="mw-page-title-main">Pesticide resistance</span> Decreased effectiveness of a pesticide on a pest

Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then that will reduce the pesticide's efficacy – efficacy and resistance are inversely related.

Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, and profit. 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. Most fungicides that can be bought retail are sold in liquid form, the active ingredient being present at 0.08% in weaker concentrates, and as high as 0.5% for more potent fungicides. Fungicides in powdered form are usually around 90% sulfur.

A Biopesticide is a biological substance or organism that damages, kills, or repels organisms seens as pests. Biological pest management intervention involves predatory, parasitic, or chemical relationships.

<i>Venturia inaequalis</i> Species of fungus

Venturia inaequalis is an ascomycete fungus that causes the apple scab disease.

<i>Rhizoctonia solani</i> Species of fungus

Rhizoctonia solani is a species of fungus in the order Cantharellales. Basidiocarps are thin, effused, and web-like, but the fungus is more typically encountered in its anamorphic state, as hyphae and sclerotia. The name Rhizoctonia solani is currently applied to a complex of related species that await further research. In its wide sense, Rhizoctonia solani is a facultative plant pathogen with a wide host range and worldwide distribution. It causes various plant diseases such as root rot, damping off, and wire stem. It can also form mycorrhizal associations with orchids.

<i>Alternaria solani</i> Species of fungus

Alternaria solani is a fungal pathogen that produces a disease in tomato and potato plants called early blight. The pathogen produces distinctive "bullseye" patterned leaf spots and can also cause stem lesions and fruit rot on tomato and tuber blight on potato. Despite the name "early," foliar symptoms usually occur on older leaves. If uncontrolled, early blight can cause significant yield reductions. Primary methods of controlling this disease include preventing long periods of wetness on leaf surfaces and applying fungicides. Early blight can also be caused by Alternaria tomatophila, which is more virulent on stems and leaves of tomato plants than Alternaria solani.

<i>Helminthosporium solani</i> Species of fungus

Helminthosporium solani is a fungal plant pathogen responsible for the plant disease known as silver scurf. Silver scurf is a blemish disease, meaning the effect it has on tubers is mostly cosmetic and affects "fresh market, processing and seed tuber potatoes." There are some reports of it affecting development, meaning growth and tuber yield. This is caused by light brown lesions, which in turn change the permeability of tuber skin and then it causes tuber shrinkage and water loss, which finally causes weight loss. The disease has become economically important because silver scurf affected potatoes for processing and direct consumption have been rejected by the industry. The disease cycle can be divided into two stages: field and storage. It is mainly a seed borne disease and the primary source of inoculum is mainly infected potato seed tubers. Symptoms develop and worsen in storage because the conditions are conducive to sporulation. The ideal conditions for the spread of this disease are high temperatures and high humidity. There are also many cultural practices that favor spread and development. There are multiple ways to help control the disease.

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

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

Potato virus X (PVX) is a plant pathogenic virus of the family Alphaflexiviridae and the order Tymovirales.

<span class="mw-page-title-main">Plant disease resistance</span> Ability of plants to withstand pathogens

Plant disease resistance protects plants from pathogens in two ways: by pre-formed structures and chemicals, and by infection-induced responses of the immune system. Relative to a susceptible plant, disease resistance is the reduction of pathogen growth on or in the plant, while the term disease tolerance describes plants that exhibit little disease damage despite substantial pathogen levels. Disease outcome is determined by the three-way interaction of the pathogen, the plant, and the environmental conditions.

Copper pesticides are copper compounds used as bactericides, algaecides, or fungicides. They can kill bacteria, oomycetes and algae, and prevent fungal spores from germinating. Common forms of fixed copper fungicides include copper sulfate, copper sulfate pentahydrate, copper hydroxide, copper oxychloride sulfate, cuprous oxide, and copper octanoate.

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

Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia. Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals, soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.

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

Mepronil is a fungicide used as a seed treatment or foliar spray in agriculture to protect crops from fungal diseases. It was first marketed by Kumiai Chemical Industries in 1981 using their brand name Basitac. The compound is a benzanilide which combines 2-methylbenzoic acid with the O-isopropyl derivative of 3-aminophenol to give an inhibitor of succinate dehydrogenase (SDHI).

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

Fluazinam is a broad-spectrum fungicide used in agriculture. It is classed as a diarylamine and more specifically an arylaminopyridine. Its chemical name is 3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine. The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria and also having high reactivity with thiols. It is unique amongst uncouplers in displaying broad-spectrum activity against fungi and also very low toxicity to mammals due to it being rapidly metabolised to a compound without uncoupling activity. It was first described in 1992 and was developed by researchers at the Japanese company Ishihara Sangyo Kaisha.

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

Fluxapyroxad is a broad-spectrum pyrazole-carboxamide fungicide used on a large variety of commercial crops. It stunts fungus growth by inhibiting the succinate dehydrogenase (SQR) enzyme. Application of fluxapyroxad helps prevent many wilts and other fungal infections from taking hold. As with other systemic pesticides that have a long chemical half-life, there are concerns about keeping fluxapyroxad out of the groundwater, especially when combined with pyraclostrobin. There is also concern that some fungi may develop resistance to fluxapyroxad.

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

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

<span class="mw-page-title-main">Agriculture in California</span> Sector of the Californian economy

Agriculture is a significant sector in California's economy, producing nearly US$50 billion in revenue in 2018. There are more than 400 commodity crops grown across California, including a significant portion of all fruits, vegetables, and nuts in the United States. In 2017, there were 77,100 unique farms and ranches in the state, operating across 25.3 million acres of land. The average farm size was 328 acres (133 ha), significantly less than the average farm size in the U.S. of 444 acres (180 ha).

<span class="mw-page-title-main">Pydiflumetofen</span> Chemical compound used to kill fungi

Pydiflumetofen is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2016 using their brand name Miravis. The compound is an amide which combines a pyrazole acid with a substituted phenethylamine to give an inhibitor of succinate dehydrogenase, an enzyme that inhibits cellular respiration in almost all living organisms.

References

  1. 1 2 Famoxadone Pesticide Fact Sheet, United States Environmental Protection Agency
  2. Phillip Brannen. "Fungicide resistance management for powdery and downy mildews" (PDF).
  3. 1 2 3 4 5 Knight, S. C.; Anthony, V. M.; Brady, A. M.; Greenland, A. J.; Heaney, S. P.; Murray, D. C.; Powell, K. A.; Schulz, M. A.; Spinks, C. A.; Worthington, P. A.; Youle, D. (1997). "Rationale and Perspectives on the Development of Fungicides". Annual Review of Phytopathology . 35 (1). Annual Reviews: 349–372. doi:10.1146/annurev.phyto.35.1.349. ISSN   0066-4286.
  4. 1 2 3 4 5 6 7 Schepers, Huub T. A. M.; Cooke, Louise R. (2015). "Potato Pathogens in Northern and Western Europe". In Ishii H., Hollomon D. (ed.). Fungicide Resistance in Plant Pathogens. Tokyo: Springer Japan. pp. 355–378. ISBN   978-4-431-55641-1.
  5. 1 2 FRAC (Fungicide Resistance Action Committee) (March 2021). "FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels)" (PDF). pp. 1–17. Archived from the original (PDF) on 2021-11-05. Retrieved 2021-07-12.
  6. Cramer, William A.; Zhang, Huamin; Yan, Jiusheng; Kurisu, Genji; Smith, Janet L. (2006). "Transmembrane Traffic in the Cytochrome b6f Complex". Annual Review of Biochemistry . 75 (1). Annual Reviews: 769–790. doi:10.1146/annurev.biochem.75.103004.142756. ISSN   0066-4154.
  7. "Expiry of the approval of the active substance famoxadone". Pesticides: expiry of the approval of active substances. Health and Safety Executive. August 7, 2024.
  8. "Targeted risk assessment for famoxadone". European Food Safety Authority. March 9, 2023.