Fungicide

Fungicides are agents that kill, repel, prevent, or otherwise mitigate a fungus.

From: Encyclopedia of Environmental Health, 2011

Plant Health Management: Fungicides and Antibiotics

A.J. Leadbeater, in Encyclopedia of Agriculture and Food Systems, 2014

Fungicide Resistance and Its Management

Fungicide resistance is the naturally occurring, inheritable adjustment in the ability of individuals in a population to survive a plant-protection product treatment that would normally give effective control (OEPP/EPPO, 1999). Although resistance can often be demonstrated in the laboratory (and is, indeed, an important part of resistance-risk assessment for new fungicides), this does not necessarily mean that disease control in the field is reduced. ‘Practical resistance’ is the term used for the loss of field control due to a shift in the pathogen′s sensitivity to a fungicide. When it occurs in the field, fungicide resistance affects all those concerned with crop health; the growers, advisors, and the industry that provides these with the advice and products necessary to ensure a healthy, productive crop. Without successful resistance management, the effectiveness and eventually the number of modern fungicides available to the farmer and grower will diminish rapidly, leading to poor yields and reduced crop quality. Such a scenario could quickly lead to overuse of affected fungicides as users strive to get products to work (e.g., higher dose rates being used, or an increase in the frequency of application), leading in turn to increased and undesirable loading on the environment.

Growers and the agrochemical industry have lived with resistance problems for many years. Resistance was not considered to be a real problem in the early 1960s – fungicides had been used over many years, quite intensively in several crops, with no obvious signs of problems. At that time, the fungicide market consisted largely of nonsite-specific, nonsystemic, and moderately effective fungicides. There were some reports of resistance to diphenyl and sodium-o-phenylphenate in Penicillium digitatum in citrus at that time (Harding, 1962), and a failure of hexachlorbenzene to control Tilletia foetida in Australia (Kuiper, 1965); in addition, some isolates of Pyrenophora avenae in oats in Scotland were found to be resistant to organomercurial seed treatment (Noble et al., 1966), but these were a small number of cases and were not considered to be very economically significant. Moreover, the fungicides had been in use for many years and so were not considered to have important consequences in terms of relevance to other fungicide and disease combinations.

However, the cases of practical resistance to the benzimidazole fungicide benomyl after only 2 years of commercial use in the USA on cucurbit powdery mildew caused far more concern (Schroeder and Provvidenti, 1969). Other reports of resistance to benomyl and other related fungicides followed quite quickly afterward. Reports of resistance to fungicides became more frequent following these early cases and, in the 1970s, reports were published documenting resistance to important fungicides such as dodine, kasugamycin, and the phenyltins. Since the 1970s, cases of resistance to fungicides have increased in number, significance, and geographical spread, with the phenylamides, dicarboximides, SMIs (e.g., triazoles), QoIs (e.g., strobilurins), and, more recently, the SDHIs all suffering from to shifts in sensitivity or full practical resistance in key crops and diseases.

From the above, it can be easily realized that fungicide resistance is a real threat to the effectiveness of many fungicide groups and must be managed, to ensure good product performance in the field for the grower and also to justify sustainable investment by the agrochemical industry into new fungicides. Fortunately, despite a general widespread occurrence of resistance to several fungicides, effective management strategies have limited the impact of this on crop protection and production. Fungicide resistance has been much researched and with the expert knowledge that such research has provided, effective resistance management strategies have been developed and implemented. Because the risk of the impact of resistance being high is directly related to the degree of exposure of the plant pathogen to a fungicide (or a group of fungicides belonging to the same cross-resistance group as defined by FRAC), most resistance management strategies involve limiting the number of applications of the ‘at-risk’ fungicide in a disease-control program. The other fungicides used in the disease control program must have different modes of action to the fungicide in consideration. Other fundamentals of resistance management include the use of mixtures of fungicides from different cross-resistance groups to avoid reliance on a single mode of action, starting the fungicide spray program early in disease epidemics (to reduce the probability that a chance mutation conferring resistance has happened in the fungal population) and to avoid long persistence of a single ‘at-risk’ fungicide in a crop such as might be experienced by a soil application targeted to control foliar disease in the crop. It is clear from these basic principles of fungicide resistance management that there is a high requirement for many fungicides with different modes of action to be available for the grower to choose from, which includes the preservation in the market place of the older modes of action such as multisites, which have a low resistance risk (Leadbeater et al., 2008; Leadbeater, 2011). The importance of fungicide resistance management becomes more clear when the fungicide market is considered. In 2011, considering the highest selling fungicides and their classes, 62% of the world fungicide market (by value) consisted of only six single-site modes of action (Table 3). These six mode-of-action groups are the QoIs, the azoles, benzimidazoles, SDHIs, phenylamides, and amines. Of these six, five are classified by FRAC as high risk or between medium and high risk of resistance occurring. Only 18% fall into the category of low resistance risk (23% if ‘resistance not known’ fungicides are included; Table 4). These statistics do not give the complete picture with regard to treated areas with each mode of action of course, but show clearly what fungicides growers depend on most to provide disease control.

Table 4. Resistance risk classification of fungicides according to the Fungicide Resistance Action Committee (FRAC) Code List 2012a

Resistance risk classificationNumber of fungicide groups (FRAC code list)Number of fungicidesWorldwide sales 2011a (US$×1000)b
High4304 041
High to medium424836
Medium8513 868
Medium to low11361 269
Low11232 348
Not known1932718
Others (bactericides, etc.)225
Total5719613 305
a
Excluding biologicals.
b
Calculated values based on data from AMIS., 2012. Crop Protection and Seeds Database. Midlothian, UK: AMIS and Phillips McDougall (2012) (www.Phillipsmcdougall.com).

In recognition of the challenge set by the possibility of fungicide resistance developing., and with the experiences of the benzimidazoles and phenylamides, FRAC was formed following a course in resistance in 1980 and a subsequent seminar in Brussels in 1981; FRAC is still extremely active today (Leadbeater, 2012b, www.FRAC.info). The purpose of FRAC is to provide fungicide resistance management guidelines to prolong the effectiveness of ‘at-risk’ fungicides and to limit crop losses should resistance occur. FRAC members are recognized industry experts in the field of fungicide resistance and are actively engaged in scientific work and discussions and are frequent contributors at educational events such as scientific symposia and symposia. Important resources have been produced by FRAC and are available on the FRAC website, including educational monographs, sensitivity testing methods, classification tables of fungicide mode of action grouping, summaries of records of fungicide resistance cases, and much more. Importantly, the updated situation with regard to resistance to the most important groups of ‘at-risk’ fungicides is available on the website for consultation and downloading. FRAC does not work in isolation, of course, and the key is cooperation and consultation between FRAC members and researchers, consultants, advisors, and officials in public and private organizations in order to share scientific information and enable all to come to common, supported conclusions, practical advice, and recommendations.

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Biodegradation of Pesticides

Mukesh Doble, Anil Kumar, in Biotreatment of Industrial Effluents, 2005

Fungicides

Fungicides are substances used to kill fungi. They can be of biological or chemical origin, and can be broadly classified into two major types:

Preventive fungicides–These are substances that prevent fungal infections from occurring in a plant. They include compounds such as sulfur, dichlorocarbamates, organometallics, pthalimides, and benzimides.

Curative fungicides–These are substances that move to the place where the infection has occurred and prevent further development of the pathogen. They include compounds such as acetimides, dicarboxymides, sterol inhibitors, and many others.

Pentachlorophenol (PCP) is one of the most commonly used fungicides. It acts as both a preventive and a curative fungicide. Many white rot fungi, including Phaneiochaete chrysosporium, are effective in breaking down PCP as well as other compounds like DDT and phenanthrene. Tiametes versicolor is another fungus that degrades PCP when it is in aerobic mode in a continuous fluidized bed; This fungus was also effective in batch reactors when the biomass was immobilized on foam cubes.

The fungicide mefenoxam was effectively degraded in 21 days (78%) by a rhizosphere system containing Zinnia angustifolia (Tropic Snow) in a bark and sand potting mix, whereas only 44% of the fungicide was degraded in the absence of the plant. Pure cultures of Pseudomonas flurescens and Chyrsobacterium indologenes isolated from the rhizosphere system could degrade the fungicide within 54 h (Pai et al., 2001).

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Diseases of rubber trees: Malaysia as a case study

Murnita Mohmad Mahyudin, ... Khairulmazmi Ahmad, in Forest Microbiology, 2023

Fungicide drenching

Fungicide drenching is a popular treatment as it is less labor intensive compared to the application of collar protectant. This method is simple, quick, and suitable in areas with labor shortages. This technique also avoids damaging the roots as no excavation of the tree collar is required. So, it is applicable for immature trees as it is difficult to treat immature plants with collar-protectant dressing without damaging the root system. The effectiveness of the fungicide drenching technique depends on the tree’s age, the severity of infection, the dosage, and frequency of drenching (Tan and Hashim, 1992).

Several fungicides have been tested to observe their effectiveness on R. microporus. For example, triadimefon, triadimenol, tebuconazole, and hexaconazole are effective systemic fungicides for white root disease control (Jayaratne et al., 2001). However, if cost involved is a consideration, only tebuconazole and hexaconazole are recommended for use. The half-life of hexaconazole and tebuconazole in tropical soil is approximately 2 months with only 15% of chemical residue remains in the soil 6 months after application (Atreya, 1990). Thus, the effectiveness of fungicides is reduced within 2–4 months after application. A follow-up application is important to achieve an effective control and to prevent re-occurrence of the disease. In general, two drenchings applied at 5–6-month intervals are required to achieve a satisfactory control.

Three different fungicides, triadimefon, triadimenol, and tridemorph, were effective in controlling White Root Disease on both mature and immature rubber trees (Ng and Yap, 1990). However, it is important to note that different tree ages require different rates of fungicides, i.e., older trees require higher effective rate compared to younger trees. Chan et al. (1991) and Hashim and Chew (1997) have recommended the use of propiconazole, triadimefon, and triadimenol to control white root disease on immature rubber trees. Meanwhile, Lam and Chiu (1993) recommended the use of hexaconazole at 0.5 g a.i/plant in 2 L of water at the base of a one-year-old rubber trees followed by a repeat application 4 months later as it was found to be more efficient and cost-effective compared to propiconazole.

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Maneb

J.R. Roede, G.W. Miller, in Encyclopedia of Toxicology (Third Edition), 2014

Uses

MB is employed as a fungicide used to control over 400 fungal pathogens and is applied to more than 100 different crops. Some of these crops include grapes, potatoes, citrus, and apples. It is used to control early and late blights on these crops as well as ornamental plants. MB and other EBDC are key components of fungicide resistance management programs due to a multisite mode of action; therefore, in over 40 years of use, no resistance has ever developed to MB or any of the EBDC fungicides. MB is available as granular, wettable powder, flowable concentrate, and ready-to-use formulations, in addition to being a component of fungicide mixtures. It should also be noted that MB is also used by the plastics and rubber industries as accelerators and catalysts.

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Humans & Conservation

Paul C. Jepson, in Encyclopedia of Biodiversity (Third Edition), 2013

Inorganic

Inorganic fungicides are derived from sulfur or simple metal salts. They are generally stable, persistent, and insoluble in water. They include sulfur, which was originally applied as flowers of sulfur, in dust form, and which is still used, but in a more highly ground colloidal suspension. It has both direct contact and fumigant activity at temperatures above 20 °C, but above 32 °C the vapor may cause phytotoxicity (toxic harm to the target plant). Environmental damage and toxicological impacts to nontarget organisms are otherwise limited. Copper-based fungicides include Bordeaux mixture, an early fungicide that consists of a solution of copper sulfate and hydrated lime. With 12% copper, this fungicide has low mammalian toxicity. A more stable form of copper (e.g., copper oxychloride) is used in modern formulations, enabling the slow release of copper into leaf surface water film and toxic buildup in fungal tissue. Other inorganic fungicides have included heavy-metal-containing materials that incorporate mercury, zinc, nickel, or chromium. These are normally highly toxic and persistent, and they have been banned internationally.

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Volume 5

C. Bolognesi, F.D. Merlo, in Encyclopedia of Environmental Health (Second Edition), 2019

Fungicides

Fungicides are agents that kill, repel, prevent, or otherwise mitigate a fungus. Fungicides, according to the role of protection in plants, are classified as: protectant or preventive if they prevent the infection from occurring, antisporulants if they prevent spores from being produced, and curative if they inhibit the development of a disease following an infection. According to their mobility in plant, they are categorized as contact and systemic.

A large number of active ingredients are used as fungicides with different mechanisms of actions (Table 2). Single-site fungicides are active only at one point in a metabolic pathway in a fungus or on a single critical enzyme or protein needed by the fungus. Multisite fungicides affect a number of different metabolic sites within the fungus.

Table 2. Most common classes of synthetic fungicides

Chemical groupChemical classesActive ingredientsMode of action
Inhibition of mitosis and cell division
Benzimidazoles and benzimidazole precursorsBenzimidazolesBenomyl, carbendazimBeta-tubulin assembly in mitosis
Empty CellThiophanatesMethyl-thiophanates
N-PhenylcarbamatesDiethofencarb
BenzamidesZoxamide
PhenylureasPencycuronCell division
Inhibition of nucleic acid synthesis
Hydroxy-(2-amino) pyrimidinesBupirimate, dimethirimol, ethirimolPurine metabolism
AcylalaninesPhenylamidesBenalaxilRNA polymerases I
ButyrolactonesMethalaxyl
Empty CellOxazolidinonesFuralaxyl
HeteroaromaticsIsoxazolesHymexazolDNA, RNA synthesis
Empty CellIsothiazolonesOcthilinone
Carboxylic acidsOxolinic acidDNA supercoiling
Inhibition of lipid and membrane synthesis
Phosphoro-thiolates, dithiolanesPhosphorothiolatesPyrazofos, IprobenfosPhospholipid biosynthesis
Empty CellDithiolanesIsoprothiolane
Aromatic hydrocarbon and heteroaromaticsNitrobenzenesDicloran, quintozeneLipid peroxidation
BenzenesChloroneb, biphenyl
Empty CellThiadiazolesEtridiazole
CarbamatesPropamocarb, iodocarbCell membrane permeability
Carboxylic acid amidesCinnamic acid amidesDimethomorph, flumorphPhospholipid biosynthesis
Mandelic acid amidesMandipropamid
Empty CellValinamide carbamatesIprovalicarb, valiphenal
Inhibition of amino acid and protein synthesis
Anilino pyrimidinesCyprodinyl, mepanipirymMethionine biosynthesis
AntibioticsEnopyranuronic acidBlasticidin SProtein synthesis
HexopyranosylKasugamycin
GlucopyranosylStreptomycin
Empty CellTetracyclinOxytetracyclin
Inhibition of sterol biosynthesis
ConazolesTriazolesAzaconazole, cyproconazole, triadimefom, triticonazolesDemethylation inhibition
ImidazolesAmisulbrom, bitertanol, fluotrimazole
PyrimidinesPyrifenox
PiperazinesTriforine
Empty CellImidazolesImazalil, prochloraz, triflumizole
Inhibition of signal transduction
QuinolinesQuinoxifenG-protein in early cell –signaling
DicarboximidesIprodione, chlozolinate, procymidone, vinclozolinOsmotic signal transduction
PhenylpyrrolesPenpiclonil, fludioxonil
Inhibition of respiration
Pyrimidine aminesDifluometorimInhibition of complex I
CarboxamidesBenzamidesBenodanil, mepronil, flutolanil, carboxin, flutolanil, oxycarboxinInhibition of complex II (succinate dehydrogenase)
Furan carboxamidesFenfuran
Triazole carboxamidesThifluzamide
Oxathiin carboxamidesOxycarboxim, carboxim
Pyrazole carboxamidesPenthiopyrad, furametpyr
Empty CellPyridine carboxamides
Quinone outside inhibitorsMethoxyacrilatesAzoxystrobin, picoxystrobin, enestrobinInhibition of complex III (cytochrome bc1 (ubiquinol oxidase)) at Qo site
Methoxy-carbamatesPyraclostrobin
Oximino acetatesKresoxim methyl
Oxazolidine-dionesFamoxadone
DinitrophenolDinocap, binapacrylUncouplers of oxidative phosphorylation
Empty CellPyridineFluazinam
OrganotinFentin acetate, fentin chloride, fentin hydroxideInhibition of ATP synthase
Multisite action
InorganicSulfur, copperInactivation of enzymes
DithiocarbamatesFerbam, metiram, maneb, mancozeb, propineb, zineb, ziramInhibition of enzyme activity by complexing with metal-containing enzymes
PhthalimidesCaptan, captafol, folpet
TriazinesAnilazine
AnthraquinonesDithianon
SulphamidesDichlofluanid, tolyfluanid
GuanidinesDodine, iminoctadine

Benzimidazoles, for example, suppress the reassembly of depolymerized spindle microtubule division. Although these compounds exhibit a specific sensitivity against fungal organisms, they target also mammalian microtubule assembly dynamics, disrupt the microtubule–kinetochore interactions, and activate spindle checkpoint protein in mammalian cells, inhibiting mitosis and cell division.

Conazoles as another example have a broad antifungal activity and are used as pharmaceuticals to treat topical and systemic fungal infections, and as agrichemicals to protect various fruit, vegetable and cereal crops, and seeds. Their antifungal characteristic is due to their ability to block the synthesis of ergosterol that is an essential component of the fungal cell membrane. The primary enzyme blocked by the conazoles is the cytochrome P450 (CYP)-51 or lanosterol-14α-demethylase, the only member of the cytochrome family present in animals, plants, fungi, and prokaryotes. In mammalian systems, conazoles modulate many CYP enzymes involved in the phase 1 metabolism of xenobiotics, sterols, steroids, vitamin D, and other endobiotics. In addition to altered expression and activity of cytochromes, other enzyme activities, the phase 2 enzymes are also altered (e.g., uridine diphosphate glucuronyltransferase (DPGT) and glutathione S-transferase (GST)). Inorganic active ingredients, such as sulfur or copper, and the widely used dithiocarbamates have a multisite action inhibiting different enzymes by complexing with metal-containing molecules.

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Federal Insecticide, Fungicide, and Rodenticide Act, US

P. Krishnan, in Encyclopedia of Toxicology (Third Edition), 2014

Abstract

The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) governs the selling and distribution of pesticides in the United States. Replacing the Insecticide Act of 1910, FIFRA made pesticide registration mandatory for the sale and distribution. Advances in the field of toxicology and the increased public awareness in the matter of environmental safety have resulted in periodic amendments of this Act. In its current form, FIFRA ensures that the pesticide in use is not only registered but also is safe for human beings, including infants and children; harmless to nontarget living organisms; and poses no unreasonable adverse effects on the environment.

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Fungicide and pesticide fallout on aquatic fungi

Abdullah Kaviani Rad, ... Hassan Etesami, in Freshwater Mycology, 2022

4 Future perspectives

Chemical fungicides play a significant role in modern agriculture (Skevas, Oude Lansink, & Stefanou, 2013). There can be no doubt that pesticide use may pose risks to the environment and human health [Sustainable Use Directive 2009/128/EC and Plant Protection Products Regulation (EC) 1107/2009]. But the benefits of fungicides would outweigh the risks if they are implemented following recommended application rates. Non-target effects of synthetic fungicides can be minimized by developments in organic chemistry and distribution systems that reduce the fungicide doses (Thind, 2017). For example, water-soluble bags and carriers for pesticide preparation as starch, chitosan, clay, lignin, sodium alginate, synthetic polymers, and activated carbon (Yang, Zang, Zhang, Wang, & Yang, 2019). These technologies have advantages such as the controlled release of pesticides, lower toxicity, reduced risk of pesticide residues in soil and water, and enhanced product effectiveness to target organisms.

Innovations in biotechnology are the future perspectives of fungicides; ; ; .

New-generation fungicides have a novel mode of action. These plant protection products are very effective even at low application rates, are more target unique, and produce no or minimal residue on harvested crops (Adeniyi, Kunwar, Dongo, Animasaun, & Aravind, 2020).

An integrated approach combining biocontrol agents with synthetic fungicides also reduces pest pressure (Ons et al., 2020; Zhang, Godana, et al., 2020). Bio-fungicides are the focused areas of research in fungicide discovery. However, the recent study shows that bio fungicides have not attained the required application level to displace chemical fungicides. There are several problems in terms of stability, the field uses and distribution systems (Koul, 2019). Use of nanoformulations of Ag, Cu, SiO2, and ZnO, nanobiofungicides, and financing in exploiting the increasingly accessible genome sequences of the most harmful phytopathogenic fungi. The molecular genetic approaches are the powerful alternatives for ecologically sustainable pest management in the nearest future (Abd-Elsalam, Al-Dhabaan, Alghuthaymi, Njobeh, & Almoammar, 2019). Nanotechnology can also help overcome the limitations of common fungicides in plant disease management and contribute to creating a safe ecosystem (Lipsa, Ursu, Ursu, Ulea, & Cazacu, 2020).

In conclusion, the efforts of chemistry, biotechnology and the role of genetic engineering will possibly help to reduce the chances of resistance development and minimize the negative consequences to the environment and human health. These innovations are impossible without efficient and environmentally sound pest control management (Popp, Petö, & Nagy, 2013). Management measures should also be taken to protect the biodiversity of fungi (Irga, Dominici, & Torpy, 2020). Total investment in pest management and new scientific knowledge should be grown to satisfy the food requirements of a growing population and prevent unnecessary damage to the environment.

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Lead and Public Health

Paul Mushak, in Trace Metals and other Contaminants in the Environment, 2011

25.5.5 The Federal Insecticide, Fungicide, and Rodenticide Act

FIFRA, with respect to research, data collection, and analysis with any eye to multimedia lead considerations, enables the U.S. EPA to do research to achieve the legislation's ends, while §§20(a) and 20(b) direct the U.S. EPA Administrator to cooperate with other Federal agencies in executing the Act's provisions. FIFRA requires the Agency to register all pesticides, to set standards for the use of restricted pesticides, and to initiate cancellation or suspension for those substances posing unreasonable adverse effects on the environment.

Section 3(c)(5) requires pesticides’ entry to the market have their chemical composition support claims for use, meet labeling requirements, and perform the claimed function without “unreasonable adverse effects on the environment.” This requirement that there not be unreasonable risks of harm to humans or ecosystems foretells analysis for costs versus benefits and is assumed to include the cumulative effects of multimedia exposures to the pesticide.

EPA's legal actions in the earlier years of the act's existence principally involved those pesticides showing some evidence of carcinogenic action. Carcinogenicity is one toxicological behavior of paramount importance in addressing cumulative loading into environmental compartments encountered by human populations. Cumulative contributions in human exposures certainly call forth a multimedia dimension. Pesticides have primarily been those with organic chemical structures. Lead-based pesticides were phased out from heavy use in orchard crop production, e.g., apple orchards, long ago. Lead as a larvicide included its application as lead arsenate, the arsenate having recognized high carcinogenic potency in exposed humans at particularly high risk.

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Chitosan conjugates, microspheres, and nanoparticles with potential agrochemical activity

Tirupaati Swaroopa Rani, ... Appa Rao Podile, in Agrochemicals Detection, Treatment and Remediation, 2020

Abstract

Chemical fungicides and pesticides are used for effective control of phytopathogens. However, the deleterious effects of these chemicals on human health and environment strongly demand the search for an alternative eco-friendly approach for pathogen control. Chitosan is a biodegradable, biocompatible, and nontoxic cationic polymer and has received great attention as a biopesticide. Chitosan and its derivatives are known for their potential diverse bioactivities, to mention a few, antimicrobial activity, plant growth promotion, disease control, drug delivery systems, etc. Chitosan(s) with their polycationic nature can chelate with many organic and inorganic compounds and thus can improve the bioavailability, stability, and biocidal activity of a variety of fungicides or pesticides or bioactive molecules. This property of chitosan(s) is exploited to some extent, particularly, for the development of micro- and/or nano-formulations. The adsorption enhancing effect of chitosan microspheres and nanoparticles improves the bioavailability of the encapsulated active ingredients, extending the interaction time between active ingredients and the target. In addition, a controlled and sustainable release of agrochemicals or micronutrients will be achieved. This chapter highlights the advantages of chitosan, and their derivatives, as potential delivery systems for sustainable improvement of agriculture.

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