Anilinopyrimidine
   HOME

TheInfoList



OR:

Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their
spore In biology, a spore is a unit of sexual or asexual reproduction that may be adapted for dispersal and for survival, often for extended periods of time, in unfavourable conditions. Spores form part of the life cycles of many plants, algae, f ...
s. A
fungistatic Fungistatics are anti-fungal agents that inhibit the growth of fungus (without killing the fungus). The term ''fungistatic'' may be used as both a noun and an adjective. Fungistatics have applications in agriculture, the food industry, the paint ind ...
inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, and
profit Profit may refer to: Business and law * Profit (accounting), the difference between the purchase price and the costs of bringing to market * Profit (economics), normal profit and economic profit * Profit (real property), a nonpossessory intere ...
. Fungicides are used both in agriculture and to fight
fungal infections in animals 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 ti ...
. Chemicals used to control
oomycetes Oomycota forms a distinct phylogenetic lineage of fungus-like eukaryotic microorganisms, called oomycetes (). They are filamentous and heterotrophic, and can reproduce both sexually and asexually. Sexual reproduction of an oospore is the result ...
, which are not fungi, are also referred to as fungicides, as oomycetes use the same mechanisms as fungi to infect 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 upwardly. Most fungicides that can be bought retail are sold in a liquid form. A very common active ingredient is
sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
, 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 and are very toxic. Other active ingredients in fungicides include neem oil, rosemary oil, jojoba oil, the bacterium '' Bacillus subtilis'', and the beneficial fungus ''
Ulocladium ''Ulocladium'' is a genus of fungi. Species of this genus contain both plant pathogens and food spoilage agents. Other species contain enzymes that are biological control agents. Some members of the genus can invade homes and are a sign of mo ...
oudemansii''. Fungicide
residues Residue may refer to: Chemistry and biology * An amino acid, within a peptide chain * Crop residue, materials left after agricultural processes * Pesticide residue, refers to the pesticides that may remain on or in food after they are appli ...
have been found on food for human consumption, mostly from post-harvest treatments. Some fungicides are dangerous to human health, such as
vinclozolin Vinclozolin (trade names Ronilan, Curalan, Vorlan, Touche) is a common Dicarboximide fungicides, dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, let ...
, which has now been removed from use. Ziram is also a fungicide that is toxic to humans with long-term exposure, and fatal if ingested. A number of fungicides are also used in human health care.


Types


Organic chemicals

* Mancozeb * Myclobutanil


Inorganic chemicals

* Copper *
Sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
* Phosphorous acid


Mycoviruses

Some of the most common
fungal crop pathogen Plant pathology (also phytopathology) is the scientific study of diseases in plants caused by pathogens (infectious organisms) and environmental conditions (physiological factors). Organisms that cause infectious disease include fungi, oomyc ...
s are known to suffer from
mycovirus Mycoviruses (Ancient Greek: μύκης ' ("fungus") + Latin '), also known as mycophages, are viruses that infect fungi. The majority of mycoviruses have double-stranded RNA (dsRNA) genomes and isometric particles, but approximately 30% have po ...
es, and it is likely that they are as common as for plant and animal viruses, although not as well studied. Given the obligately parasitic nature of mycoviruses, it is likely that all of these are detrimental to their hosts, and thus are potential biocontrols/biofungicides.


Natural fungicides

Proponents of natural pest management claim that certain plant-based chemical have fungicidal activity. Plants and other organisms have chemical defenses that give them an advantage against microorganisms such as fungi. Some of these compounds are used as fungicides, although their efficacy is doubted: *
α-Cadinol α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol. Natural occurrence This compound is found in essential oils and extracts of many plants, such as *'' Agrotaxis selaginoides'', * ''Tabernaemontana catharin ...
(present in essential oils of different plants) * Citronella oil *
Gmelinol Gmelinol is a lignan. (+)-Gmelinol can be isolated from the heartwood of ''Gmelina arborea''. This compound, along with four other chemicals also found in the same species, (+)-7′-O-ethyl arboreol, (+)- paulownin, (+)-epi eudesmin and (−)-β-s ...
(isolated from '' Gmelina arborea'') * Hinokitiol (isolated from ''
Cupressaceae Cupressaceae is a conifer family, the cypress family, with worldwide distribution. The family includes 27–30 genera (17 monotypic), which include the junipers and redwoods, with about 130–140 species in total. They are monoecious, subdio ...
'' trees) * Jojoba oil *
Mesquitol Mesquitol is a flavan-3-ol, a type of flavonoid. ''Prosopis juliflora'', an invasive New World mesquite now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood. Mesquitol, with its pyrogallol-type A-ring, is more susceptib ...
(isolated from '' Prosopis'' trees) * Nimbin (isolated from neem)


Resistance

Pathogens respond to the use of fungicides by evolving
resistance Resistance may refer to: Arts, entertainment, and media Comics * Either of two similarly named but otherwise unrelated comic book series, both published by Wildstorm: ** ''Resistance'' (comics), based on the video game of the same title ** ''T ...
. In the field several mechanisms of resistance have been identified. The evolution of fungicide resistance can be gradual or sudden. In qualitative or discrete resistance, a mutation (normally to a single gene) produces a race of a fungus with a high degree of resistance. Such resistant varieties also tend to show stability, persisting after the fungicide has been removed from the market. For example,
sugar beet A sugar beet is a plant whose root contains a high concentration of sucrose and which is grown commercially for sugar production. In plant breeding, it is known as the Altissima cultivar group of the common beet (''Beta vulgaris''). Together wi ...
leaf blotch remains resistant to azoles years after they were no longer used for control of the disease. This is because such mutations have a high selection pressure when the fungicide is used, but there is low selection pressure to remove them in the absence of the fungicide. In instances where resistance occurs more gradually, a shift in sensitivity in the pathogen to the fungicide can be seen. Such resistance is polygenic – an accumulation of many mutations in different genes, each having a small additive effect. This type of resistance is known as quantitative or continuous resistance. In this kind of resistance, the pathogen population will revert to a sensitive state if the fungicide is no longer applied. Little is known about how variations in fungicide treatment affect the selection pressure to evolve resistance to that fungicide. Evidence shows that the doses that provide the most control of the disease also provide the largest selection pressure to acquire resistance, and that lower doses decrease the selection pressure. In some cases when a pathogen evolves resistance to one fungicide, it automatically obtains resistance to others – a phenomenon known as
cross resistance Cross-resistance is when something develops resistance to several substances that have a similar mechanism of action. For example, if a certain type of bacteria develops resistance to one antibiotic, that bacteria will also have resistance to sev ...
. These additional fungicides are normally of the same chemical family or have the same mode of action, or can be detoxified by the same mechanism. Sometimes negative cross resistance occurs, where resistance to one chemical class of fungicides leads to an increase in sensitivity to a different chemical class of fungicides. This has been seen with
carbendazim Carbendazim is a widely used, systemic, broad-spectrum benzimidazole fungicide and a metabolite of benomyl. It is also employed as a casting worm control agent in amenity turf situations such as golf greens, tennis courts etc. and in some countr ...
and diethofencarb. There are also recorded incidences of the evolution of multiple drug resistance by pathogens – resistance to two chemically different fungicides by separate mutation events. For example, '' Botrytis cinerea'' is resistant to both azoles and
dicarboximide fungicides Dicarboximide (or dicarboxamide) fungicides are a family of agricultural fungicides that include vinclozolin, iprodione, and procymidone. Dicarboximides are believed to inhibit triglyceride biosynthesis in sclerotia-forming fungi, including ''Bot ...
. There are several routes by which pathogens can evolve fungicide resistance. The most common mechanism appears to be alteration of the target site, in particular as a defence against single site of action fungicides. For example, Black Sigatoka, an economically important pathogen of banana, is resistant to the
QoI 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 ...
fungicides, due to a single nucleotide change resulting in the replacement of one amino acid (glycine) by another (alanine) in the target protein of the QoI fungicides, cytochrome b. It is presumed that this disrupts the binding of the fungicide to the protein, rendering the fungicide ineffective. Upregulation of target genes can also render the fungicide ineffective. This is seen in DMI-resistant strains of '' Venturia inaequalis''. Resistance to fungicides can also be developed by efficient
efflux Efflux may refer to: * Efflux (microbiology), a mechanism responsible for moving compounds out of cells * e-flux, a publishing platform and archive See also * Efflux time, part of a measure of paint viscosity * Flux (biology) In general, flux ...
of the fungicide out of the cell. ''
Septoria tritici ''Zymoseptoria tritici'', synonyms ''Septoria tritici'', ''Mycosphaerella graminicola'', is a species of filamentous fungus, an ascomycete in the family ''Mycosphaerellaceae''. It is a wheat plant pathogen causing septoria leaf blotch that is ...
'' has developed multiple drug resistance using this mechanism. The pathogen had five ABC-type transporters with overlapping
substrate Substrate may refer to: Physical layers *Substrate (biology), the natural environment in which an organism lives, or the surface or medium on which an organism grows or is attached ** Substrate (locomotion), the surface over which an organism lo ...
specificities that together work to pump toxic chemicals out of the cell. In addition to the mechanisms outlined above, fungi may also develop metabolic pathways that circumvent the target protein, or acquire enzymes that enable metabolism of the fungicide to a harmless substance.


Fungicide resistance management

The Fungicide Resistance Action Committee (FRAC) has several recommended practices to try to avoid the development of fungicide resistance, especially in at-risk fungicides including ''Strobilurins'' such as azoxystrobin. FRAC assigns groups of fungicides into classes where cross-resistance is likely, usually because the active ingredients share a common mode of action. FRAC is organized by
CropLife International CropLife International is an international trade association of agrochemical companies founded in 2001. It was previously known as ''Global Crop Protection Federation'' and started out as ''International Group of National Associations of Manufactur ...
. Products should not always be used in isolation, but rather as mixture, or alternate sprays, with another fungicide with a different mechanism of action. The likelihood of the pathogen's developing resistance is greatly decreased by the fact that any resistant isolates to one fungicide will be killed by the other; in other words, two mutations would be required rather than just one. The effectiveness of this technique can be demonstrated by Metalaxyl, a
phenylamide Anilides (or phenylamides) are a class of chemical compounds, which are amide derivatives of aniline. Preparation Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chlorid ...
fungicide. When used as the sole product in Ireland to control potato blight ('' Phytophthora infestans''), resistance developed within one growing season. However, in countries like the UK where it was marketed only as a mixture, resistance problems developed more slowly. Fungicides should be applied only when absolutely necessary, especially if they are in an at-risk group. Lowering the amount of fungicide in the environment lowers the selection pressure for resistance to develop. Manufacturers’
dose Dose or Dosage may refer to: Music * ''Dose'' (Gov't Mule album), 1998 * ''Dose'' (Latin Playboys album) * ''Dosage'' (album), by the band Collective Soul * "Dose" (song), a 2018 song by Ciara * "Dose", song by Filter from the album '' Short ...
s should always be followed. These doses are normally designed to give the right balance between controlling the disease and limiting the risk of resistance development. Higher doses increase the selection pressure for single-site mutations that confer resistance, as all strains but those that carry the mutation will be eliminated, and thus the resistant strain will propagate. Lower doses greatly increase the risk of polygenic resistance, as strains that are slightly less sensitive to the fungicide may survive. It is better to use an integrative pest management approach to disease control rather than relying on fungicides alone. This involves the use of resistant varieties and hygienic practices, such as the removal of potato discard piles and stubble on which the pathogen can overwinter, greatly reducing the titre of the pathogen and thus the risk of fungicide resistance development.


See also

* Antifungal drug * Index of pesticide articles * List of fungicides * PHI-base (Pathogen-Host-Interaction database) *
Phytopathology Plant pathology (also phytopathology) is the scientific study of diseases in plants caused by pathogens (infectious organisms) and environmental conditions (physiological factors). Organisms that cause infectious disease include fungi, oomyc ...
* Plant disease forecasting


References


External links


Fungicide Resistance Action CommitteeFungicide Resistance Action Group
United Kingdom

- National Pesticide Information Center, Oregon State University, United States {{Authority control Mycology Biocides