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Fluopyram

Fluopyram is a broad-spectrum systemic and belonging to the inhibitor (SDHI) class of the pyridinyl-ethyl- chemical group, with the molecular formula C₁₆H₁₁ClF₆N₂O and IUPAC name N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl). Developed by CropScience and first registered for commercial use by the U.S. EPA in 2012, it exhibits preventive, curative, and translaminar activity by inhibiting spore , germ tube , , and sporulation in target pathogens. Fluopyram is primarily applied as a foliar spray, , or drench in crops such as fruits, , cereals, and turf to control diseases caused by ascomycetes and basidiomycetes, including Botrytis spp., , Sclerotinia spp., and Monilinia spp., as well as certain plant-parasitic s like root-knot and species. Its nematicidal properties, discovered post-development as a , stem from disruption of nematode energy metabolism and motility, providing benefits. The compound's low volatility, moderate water solubility (16 mg/L at 20 °C, 7), and DT₅₀ of 200–350 days contribute to its persistence and efficacy in field conditions. Regulatory assessments by agencies like the U.S. Environmental Protection Agency (EPA) and the (EFSA) have established tolerances for fluopyram residues in food commodities, emphasizing its role in modern agriculture while monitoring potential environmental impacts such as groundwater leaching and effects on non-target organisms; as of 2025, its EU approval has been extended to 2026 amid ongoing legal challenges regarding health and environmental risks. Ongoing focuses on strategies, given its FRAC Group 7 classification, to sustain long-term effectiveness against evolving populations.

Development and history

Discovery and synthesis

Fluopyram was developed by CropScience as part of research into inhibitor (SDHI) fungicides, with initial announcements and presentations occurring around 2009. The compound, initially tested under the code USF 2015, emerged from efforts to create novel broad-spectrum agents targeting fungal pathogens, with its nematicidal properties identified subsequently during development. Fluopyram belongs to the chemical class of pyridinyl-ethyl-benzamides, a new group of SDHI fungicides designed for enhanced efficacy against soil-borne diseases. Its primary synthesis involves the condensation of with 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine, forming the benzamide linkage central to its structure. This method, typical for commercial production, proceeds through amidation, yielding the active ingredient with high purity for agricultural formulations. The initial research emphasized fluopyram's potential for broad-spectrum control of fungal and pests, positioning it as a versatile tool in crop protection from the outset of its discovery phase.

Regulatory approvals

Fluopyram received its initial approval from the U.S. Environmental Protection Agency (EPA) on February 2, 2012, as a new for use as a under registration number 264-1077. This approval was accompanied by the establishment of tolerances for residues in multiple commodities, including fruits such as apples, grapes, and peaches, as well as like tomatoes and leafy greens, to ensure safe dietary exposure levels. In the , fluopyram was approved as an active substance on August 22, 2013, pursuant to Commission Implementing Regulation (EU) No 802/2013, which implemented Regulation (EC) No 1107/2009 concerning the placing of plant protection products on the market. This approval facilitated its inclusion in plant protection products across member states, with initial maximum residue levels (MRLs) set for various commodities to align with the substance's safety profile. Following these key approvals, fluopyram became commercially available in select markets starting in 2012, with registrations expanding globally to over 70 crops by the mid-2010s, including cereals, fruits, , and field crops. Early residue tolerances were also established in other regions, such as and , mirroring the U.S. and EU frameworks for commodities like fruits and to support compliance. The EU approval has since been extended, with the current expiration set for June 30, 2026.

Chemical properties

Molecular structure

Fluopyram has the molecular formula C16H11ClF6N2O. Its IUPAC name is 2-(trifluoromethyl)-N-[2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl]benzamide. The molecule features a benzamide core, consisting of a benzene ring substituted at the ortho position with a trifluoromethyl group (-CF3) and an amide linkage, which connects via an ethyl bridge (-CH2CH2-) to the 2-position of a pyridine ring; the pyridine bears a chlorine atom at the 3-position and another trifluoromethyl group at the 5-position, accounting for the six fluorine atoms across the two -CF3 moieties. This structural arrangement, particularly the amide bond and the electron-withdrawing trifluoromethyl and chloro substituents, contributes to its classification as a inhibitor (SDHI), where the pyridyl and moieties facilitate binding to the site (Qo site) of the enzyme through hydrogen bonding and π-π interactions.

Physical and chemical characteristics

Fluopyram is an off-white to white crystalline solid at room temperature. It has a of 115.6–117.6 °C, which supports its stability during storage and formulation processes under typical agricultural conditions. The compound exhibits low solubility in water, approximately 16 mg/L at 20 °C and 7, limiting its direct dissolution but facilitating targeted delivery in formulations. In contrast, it shows high solubility in organic solvents, such as acetone (up to 250 g/L at 20 °C) and (62 g/L at 20 °C), which aids in the development of emulsifiable concentrates and other products. These solubility characteristics reflect fluopyram's moderate , quantified by a log Kow of 3.3 at 7 and 20 °C. Fluopyram demonstrates hydrolytic stability across a range of environmentally relevant values, remaining largely unchanged (>99% recovery) at 4, 7, and 9 after exposure at 50 °C for 5 days, with a exceeding one year at 25 °C. It is photostable in matrices but undergoes degradation when exposed to light in aqueous solutions, with a of approximately 21 days under simulated conditions at 7. These properties ensure reliable handling and efficacy in field applications while influencing formulation strategies to mitigate risks.

Mechanism of action

Fungicidal mode

Fluopyram is a inhibitor (SDHI) , classified by the Fungicide Resistance Action Committee (FRAC) in Group 7 due to its shared mode of action with other SDHIs. This group targets of the fungal mitochondrial , disrupting energy production essential for fungal survival. At the biochemical level, fluopyram binds to the ubiquinone-binding site (Qp site) at the interface of the SDHB, SDHC, and SDHD subunits of the (SDH) enzyme complex. This binding blocks from succinate to ubiquinone, halting the tricarboxylic acid and , which ultimately inhibits ATP synthesis and leads to fungal . The single-site action makes fluopyram highly effective against a broad spectrum of fungal pathogens but also increases the risk of resistance development through mutations in the SDH genes. Fluopyram exerts its fungicidal effects by inhibiting key stages of fungal development, including spore germination, germ tube elongation, mycelium growth, and sporulation, with germ tube elongation identified as the most sensitive stage. These disruptions prevent fungal and reproduction, providing both preventative and curative control. Within , fluopyram demonstrates translaminar movement, allowing penetration through leaf tissues, and limited systemic activity for redistribution to untreated areas.

Nematicidal effects

Fluopyram demonstrates significant nematicidal activity by disrupting the and of plant-parasitic s through interference with their energy metabolism. It specifically targets (SDH) in complex II of the mitochondrial , thereby inhibiting ATP generation critical for viability and leading to and reduced . This SDHI-based mechanism exhibits high selectivity, potently inhibiting SDH in while showing minimal effects on mammalian, , or enzymes. The compound is particularly effective against soil-borne nematodes, such as root-knot species (Meloidogyne spp.) and cyst-forming species (Heterodera spp.), which are major pests in agricultural systems. Fluopyram's nematicidal effects overlap briefly with its fungicidal , as both involve inhibition of mitochondrial via SDH targeting. In assays, exposure to fluopyram at concentrations as low as 1 μg/mL has been shown to immobilize juvenile nematodes within hours, underscoring its rapid impact on nematode physiology. In (IPM) strategies, fluopyram's dual efficacy against s and fungal pathogens allows for consolidated applications, reducing the need for multiple treatments and supporting sustainable crop protection practices. Field trials have provided evidence of its suppressive effects; for instance, in field trials with crops infested with Meloidogyne arenaria, in-furrow applications of fluopyram improved pod yields in some seasons compared to untreated controls, though it did not consistently reduce populations. Similarly, in fields targeting Meloidogyne incognita, fluopyram treatments at rates around 480–640 g/ha reduced populations of the and root damage, improving vigor and production. These results highlight fluopyram's role in managing pressure without compromising crop productivity.

Agricultural applications

Target diseases and crops

Fluopyram is primarily employed as a broad-spectrum targeting several key fungal pathogens in . It effectively controls gray mold caused by , a common disease affecting and , providing reliable suppression in crops like grapes and strawberries. Additionally, it manages on various hosts, including and grapes, through its inhibitory action on fungal . Sclerotinia rot, incited by , is another major target, particularly in and soybeans, where fluopyram reduces stem and root infections. For stone fruits, it addresses Monilinia blight caused by Monilinia species, preventing blossom and twig blights. Apple scab, driven by , is controlled in fruits, minimizing leaf and fruit lesions. Alternaria leaf spots, resulting from species, are suppressed in crops such as tomatoes and cucurbits, reducing foliar damage and yield loss. Beyond fungal pathogens, fluopyram exhibits strong nematicidal activity against plant-parasitic nematodes. It targets root-knot nematodes (Meloidogyne spp.), including M. incognita and M. arenaria, which cause and stunting in roots of susceptible . Lesion nematodes (Pratylenchus spp.), such as P. penetrans, are also managed, with reductions in population densities observed in corn and soybean fields. This dual fungicidal and nematicidal profile stems from its interference with mitochondrial respiration in these pests. The compound is applied across a diverse array of crops, encompassing fruits like apples, grapes, strawberries, and bananas; vegetables including tomatoes, peppers, and cucumbers; cereals such as wheat; and nuts like peanuts. Its efficacy spans preventative, curative, and systemic protection, enabling use on over 70 crops worldwide for integrated disease and nematode management.

Formulations and application methods

Fluopyram is commercially available in several formulations designed for effective delivery in agricultural settings, primarily as suspension concentrates (SC) for foliar and soil applications. Common products include Velum Prime, a liquid SC containing 41.5% fluopyram, used for nematode and disease suppression; Luna Experience, an SC formulation with 17.6% fluopyram combined with 17.6% for broad-spectrum fungal control; and Velum Rise, a co-formulation of fluopyram and penflufen approved in 2023 for in-furrow application in potatoes to suppress nematodes and soil-borne diseases like Rhizoctonia. Seed treatment formulations, such as ILEVO, are also suspension concentrates applied as flowable suspensions to protect against soilborne pathogens and nematodes. Application methods for fluopyram vary by crop and target , including foliar sprays for systemic uptake into tissues, seed treatments to coat prior to planting, and applications such as in-furrow placement or . Foliar applications, as in Luna Experience, are typically sprayed uniformly to cover leaves and stems, allowing penetration into buds and new growth. Seed treatments involve mixing the formulation with commercial equipment for direct injection or application, ensuring protection for emerging . methods, like those for Velum Prime, deliver the directly to the zone via in-furrow or drench to target nematodes and fungi. Typical application rates depend on the method and crop; for foliar sprays, rates range from 100 to 250 g per , with maximum annual limits of 250 g/ to prevent residue accumulation. Seed treatments commonly use 30 to 60 g per 100 kg of , equivalent to about 0.15 mg per for soybeans at standard seeding densities. In-furrow soil applications follow similar soil rates of 100 to 250 g/, adjusted for row spacing and . Fluopyram formulations are often compatible with other pesticides, enabling tank mixes with fungicides like or trifloxystrobin in products such as Luna Experience and Luna Sensation, though jar tests are recommended to confirm physical stability.

Environmental fate

Degradation and

Fluopyram is highly persistent in under aerobic conditions, with laboratory-determined DT50 values ranging from 162 to 746 days across various types and temperatures (20–25°C), reflecting slow microbial as the primary breakdown pathway. Field dissipation studies report DT50 values of 21 to 539 days, influenced by environmental factors such as temperature and . Under conditions, is even slower, with extrapolated DT50 values exceeding 1000 days in silt loam s. The primary degradates include 2,2-difluoro-benzamide (BZM) and pyridyl (PCA), which form through cleavage of the amide bond and subsequent oxidation, typically reaching low percentages of the total radioactive residue (TAR). In , fluopyram undergoes rapid uptake from or foliar application and systemic translocation via the , with occurring primarily through and . The DT50 in plant foliage ranges from 10 to 20 days, as observed in crops like (13.7–15.8 days in leaves) and (9.1–14.4 days), leading to residues dominated by the parent compound (up to 98% TRR) alongside minor degradates such as BZM and . Plant degradation is faster than in due to metabolic processes, though persistence can vary with crop type and growth stage. Photodegradation of fluopyram on the surface under is limited, showing with no significant breakdown after 23 days of artificial irradiation (λ ≥ 290 nm) in sandy loam . In contrast, aqueous photolysis under simulated yields a DT50 of 21–25 days, primarily forming the degradate (12–13% TAR). These processes contribute minimally to overall environmental dissipation compared to microbial activity.

Mobility and bioaccumulation

Fluopyram demonstrates moderate mobility in soil, characterized by organic carbon adsorption coefficients (Koc) ranging from 138 to 1,090 mL/g, with a mean value of 540 mL/g, indicating limited potential for deep leaching but possible surface movement via runoff in areas with heavy precipitation or irrigation. This moderate adsorption behavior contributes to its retention in upper soil layers, reducing widespread vertical transport while allowing occasional lateral dispersion. In aquatic environments, fluopyram persists moderately under light exposure, with a phototransformation of 21–25 days in buffered at 7 and 25°C, though it remains stable to across 4–9. Aerobic in water-sediment systems yields much longer half-lives, exceeding 1,000 days, highlighting its overall durability in low-light aquatic compartments. Bioaccumulation of fluopyram in aquatic organisms is low, with in ranging from 15 to 22, attributed to rapid and that prevent significant tissue buildup. This low BCF underscores minimal risk of trophic transfer in food webs. Detection of fluopyram in has been reported, though residues at depths of 30–90 cm reach up to 4% of applied amount in high-irrigation agricultural settings; in soils, to remains negligible under typical conditions. As of 2025, monitoring in Europe's has detected fluopyram in over 90% of samples, highlighting ongoing concerns for in intensive agricultural areas.

Toxicology

Human health impacts

Fluopyram demonstrates low in mammals. The oral LD50 in rats exceeds 2000 mg/kg body weight, classifying it in Toxicity Category III. Dermal LD50 values are similarly greater than 2000 mg/kg in rats, and the 4-hour inhalation LC50 exceeds 5.1 mg/L in rats, placing it in Category IV. The compound is non-irritating to and eyes and does not cause sensitization in standard tests. In studies, fluopyram's (NOAEL) is 1.2 mg/kg/day in rats, based on effects such as liver and alterations observed at higher doses. disruption, including increased levels and follicular , occurs in at doses above this NOAEL, though these effects are linked to a non-genotoxic involving liver . Subchronic studies in dogs establish a higher NOAEL of 28.5 mg/kg/day, with liver as the primary concern. Overall, dietary risks are considered low, with population-adjusted doses () showing exposures below 100% for sensitive groups like children. A 2025 study on fluopyram-based formulations reported cytogenotoxic effects in non-target models, suggesting potential implications for , though the pure compound remains classified as non-genotoxic. Human to fluopyram primarily occurs through dermal contact and during agricultural application, with applicators facing the highest risks, though margins of exposure (MOEs) exceed 100, indicating minimal concern. For the general , dietary intake via residues in and represents the main route, with estimated chronic exposures at 31-78% of the chronic PAD for adults and children, respectively. The U.S. Environmental Protection Agency classifies fluopyram as "not likely to be carcinogenic to humans" at doses below those inducing liver or cellular . This determination stems from the absence of in multiple and assays, including Ames tests and chromosomal aberration studies. Rodent tumors in the liver and are attributed to species-specific mechanisms not relevant to humans.

Ecotoxicological effects

Fluopyram exhibits moderate to high to aquatic organisms, with LC50 values for ranging from 0.69 to >0.98 mg/L, indicating potential risks at environmentally relevant concentrations. For , EC50 values vary by but are generally in the range of >1.1 to 16.1 mg/L, suggesting moderate , particularly to . Invertebrates such as show similar sensitivity, with 48-hour values around 0.8 mg/L. These toxicities stem from fluopyram's inhibition, which disrupts energy production in aquatic . Sublethal effects on include behavioral alterations, such as increased activity, feeding, and sociability, observed at concentrations as low as 3.5–321 µg/L in ( auratus). Fluopyram also inhibits (AChE) activity by 26–30% at these low levels, potentially impairing neurological function and increasing vulnerability to predators. Chronic exposure leads to elevated muscle lipid content (up to 3.7-fold), which may affect long-term fitness. A 2025 study further documented , , and metabolism effects in , reinforcing sublethal risks to aquatic vertebrates. In terrestrial ecosystems, fluopyram poses low acute risk to birds and bees, with oral LD50 values exceeding 2000 mg/kg body weight for bobwhite quail and >100 µg/bee for honeybees via contact and oral routes. However, chronic exposure in soil can impact earthworms, with a reproduction NOEC of 11.42 mg/kg dry weight soil for Eisenia fetida, indicating potential reproductive and growth disruptions at higher persistent residues. Nontarget fungi, including mycorrhizal communities, face suppression, as fluopyram formulations are rated as incompatible and suppressive to both endomycorrhizal and ectomycorrhizal fungi, potentially altering soil symbiosis and plant nutrient uptake. Field studies in agricultural settings, such as , reveal fluopyram residues in bee-collected exceeding 4000 ng/g, leading to detectable levels in and wild near treated areas. These residues, combined with other pesticides, may contribute to sublethal effects like reduced efficiency, though acute mortality remains low. In field margins, fluopyram was among the most frequently detected compounds in bee samples, highlighting exposure risks to populations dependent on orchard habitats. As of February 2025, environmental advocacy groups like have called for a ban on fluopyram in the due to contamination and risks to life and via . A 2025 study screened fluopyram formulations for cytogenotoxic and ecotoxicological effects on non-target organisms, finding potential DNA damage and , underscoring ongoing concerns for and ecosystems.

Regulation and legal status

Global approvals and tolerances

The (EPA) has established tolerances for residues of fluopyram in over 70 commodities, encompassing a broad array of fruits, , grains, and animal-derived products to protect consumer health. For example, the tolerance level for the pome fruit group 11-10, including apples, is set at 0.80 , while for grains such as it is 0.02 . These tolerances reflect extensive residue data and risk assessments ensuring safe dietary exposure. Post-2020 regulatory updates by the EPA include expansions and amendments to tolerances, such as revisions for the cereal grain crop group 15 (except corn and ) at 0.5 ppm in 2022 and new tolerances for green beans at 0.03 ppm in 2023. Additionally, an import tolerance for was established in 2019 at 2.0 ppm within the low-growing berry subgroup 13-07G, supporting while aligning with standards. In the , maximum residue levels (MRLs) for fluopyram are established under Regulation (EC) No 396/2005 and vary by crop, generally ranging from 0.01 mg/kg to 4.0 mg/kg based on intended uses and residue trials. Specific examples include 0.6 mg/kg for fruits such as apples and 0.4 mg/kg for pumpkin seeds following a 2024 increase from the default 0.01 mg/kg. For grains and cereals, MRLs are typically at the limit of quantification of 0.01 mg/kg. Many MRLs are harmonized with Commission standards, such as 0.9 ppm for grain and 1 ppm for canola, to facilitate agricultural exports. Fluopyram received registration in from the Australian Pesticides and Veterinary Medicines Authority (APVMA) in 2015, approving its use as a on crops including fruits and vegetables with corresponding MRLs aligned to domestic and export needs. In , the Institute for the Control of Agrochemicals, Ministry of Agriculture and Rural Affairs (ICAMA), granted registration in 2015 for technical material import and formulation uses on similar crops, establishing MRLs to support and trade. Approvals in other Asian markets, such as and , followed comparable timelines, enabling broader regional application while adhering to international residue guidelines.

Restrictions and controversies

Fluopyram's approval in the has faced significant opposition, particularly from environmental advocacy groups. In January 2025, Pesticide Action Network (PAN) Europe issued a formal call for an immediate ban on the , citing its role in contaminating through the persistent degradate (TFA). Despite this advocacy, the extended fluopyram's approval until June 2026, prompting criticism that the decision prioritizes industry interests over . In July 2025, banned fluopyram and other PFAS-containing pesticides to protect from TFA contamination. Additionally, in November 2025, EU environment ministers adopted conclusions urging action to address pollution, including from pesticides like fluopyram, at the source. Groundwater contamination by fluopyram and its metabolites has raised alarms in both the EU and the US, leading to enhanced monitoring efforts. In Europe, studies have detected fluopyram in over 90% of soil and water samples from Germany's Rhine Valley, with TFA frequently found in surface, groundwater, and even drinking water supplies. In the US, the Environmental Protection Agency (EPA) has noted fluopyram's high mobility in soil, predicting its potential leaching into groundwater, which has contributed to broader pesticide monitoring programs under the USGS National Water-Quality Assessment. These detections have fueled calls for stricter oversight to mitigate long-term aquifer pollution. The emergence of resistance to fluopyram in fungal populations, particularly , has prompted warnings from the Fungicide Resistance Action Committee (FRAC). As a inhibitor (SDHI) under FRAC code 7, fluopyram carries a medium-to-high risk of resistance development, with studies documenting resistant isolates in fields across and other regions, where up to 30% of populations showed reduced sensitivity to some SDHIs such as boscalid, with lower frequencies (around 7%) for fluopyram. FRAC recommends integrated resistance management strategies, such as alternating with unrelated fungicides, to preserve efficacy against . Advocacy groups have intensified scrutiny of fluopyram's fluorine-containing degradates, highlighting their environmental persistence and potential toxicity. TFA, a key breakdown product, is classified as a persistent, mobile, and toxic () substance that resists natural degradation and bioaccumulates in aquatic systems, exacerbating PFAS-related concerns. Organizations like PAN Europe and Beyond Pesticides argue that these degradates' long-term impacts on ecosystems and human health via water exposure have been inadequately addressed in regulatory approvals.

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