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]

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.

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

Cytochrome b within both molecular and cell biology, 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 an 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.

<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>Phaeosphaeria nodorum</i> Species of fungus

Phaeosphaeria nodorum is a major fungal pathogen of wheat, causing the disease Septoria nodorum blotch. It is a member of the Dothideomycetes, a large fungal taxon that includes many important plant pathogens affecting all major crop plant families.

<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 a plant to stand up to trouble

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.

<i>Fusarium oxysporum</i> f.sp. <i>cubense</i> Fungus, causes banana wilt/Panama disease

Fusarium oxysporum f. sp. cubense is a fungal plant pathogen that causes Panama disease of banana, also known as fusarium wilt of banana. The fungi and the related disease are responsible for widespread pressure on banana growing regions, destroying the economic viability of several commercially important banana varieties.

<span class="mw-page-title-main">Boxwood blight</span> Fungal disease affecting boxwoods

Boxwood blight is a widespread fungal disease affecting boxwoods, caused by Cylindrocladium buxicola. The disease causes widespread leaf loss and eventual death.

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

Folpet is the tradename for the organic compound with the formula C6H4(CO)2NSCCl3. It is a fungicide derived from phthalimide (C6H4(CO)2N-) and trichloromethylsulfenyl chloride. The compound is white although commercial samples can appear brownish. It is structurally related to Captan, which is also a trichloromethylsulfenyl-containing fungicide.

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

Metyltetraprole is a quinone outside inhibitor fungicide sold under the brand name Pavecto by its inventor, Sumitomo Chemical. It is the only tetrazolinone fungicide and the only one in the Fungicide Resistance Action Committee's subgroup 11A.

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 . Annual Reviews. 35 (1): 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.
  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 . Annual Reviews. 75 (1): 769–790. doi:10.1146/annurev.biochem.75.103004.142756. ISSN   0066-4154.