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Spirotetramat

Spirotetramat is a broad-spectrum, systemic insecticide belonging to the keto-enol chemical class, developed by Bayer CropScience for the control of sucking pests such as aphids, whiteflies, psyllids, mealybugs, and scales, as well as certain mites and nematodes in various crops including fruits, vegetables, and ornamentals.^[1]^[2] It is the active ingredient in commercial products like Movento, Ultor, and Kontos, and was first registered for use in 2007 in Tunisia and 2008 in the United States, not approved in the European Union as of 2025, but with approval in Great Britain until July 31, 2029, and ongoing approvals in various other regions worldwide.^[2]^[3] Chemically known as cis-4-(ethoxycarbonyloxy)-8-methoxy-3-(2,5-xylyl)-1-azaspiro[4.5]dec-3-en-2-one, it has the molecular formula C₂₁H₂₇NO₅ and CAS number 203313-25-1, existing as a chiral molecule with the active cis-isomer predominant in technical formulations.^[2] Spirotetramat's mode of action involves the inhibition of lipid biosynthesis in target insects, primarily through acetyl-CoA carboxylase disruption, leading to starvation and halted growth; it is effective when ingested and translocates bidirectionally within plants via both xylem (upward from roots) and phloem (downward and laterally), providing comprehensive protection to foliage, fruits, and roots against hidden or newly emerging pests.^[4]^[5] This systemic mobility distinguishes it in integrated pest management (IPM) programs, where it is applied as a suspension concentrate at low rates, compatible with many other pesticides and fertilizers, and supports long-lasting residual activity in dense canopies.^[1]^[2] From a toxicological perspective, spirotetramat exhibits low acute mammalian toxicity, with an oral LD₅₀ greater than 2000 mg/kg in rats, though it is classified as a skin and eye irritant, a potential skin sensitizer, and associated with reproductive and developmental effects in chronic studies, leading to an acceptable daily intake (ADI) of 0.05 mg/kg body weight per day.^[2]^[4] Ecotoxicologically, it poses moderate risks to aquatic organisms like fish and daphnia but low acute toxicity to honeybees (LD₅₀ >100 μg/bee) and earthworms, with non-persistent behavior in the environment—soil half-life of about 0.19 days and moderate soil mobility (Koc 289 mL/g)—minimizing long-term accumulation.^[2] In plants, it metabolizes primarily to spirotetramat-enol via ester bond hydrolysis, with residues declining rapidly (RL₅₀ around 13 days), ensuring compliance with maximum residue limits (MRLs) such as 0.8 mg/kg in grapes when pre-harvest intervals are observed.^[4]

Development and history

Discovery and synthesis

Spirotetramat was discovered through research conducted by Bayer CropScience in the early 2000s, focusing on tetramic acid derivatives to enhance herbicidal and miticidal activities.^[6] The compound emerged from efforts to optimize spirocyclic structures within this class, building on prior patents such as WO 98/05638, which described foundational tetramic acid scaffolds for pesticidal applications.^[7] Initial explorations targeted broad-spectrum control, with the novel spirocyclic design providing a unique keto-enol tautomer framework that distinguished it from existing insecticides.^[7] The synthesis of spirotetramat involved modifications to tetramic acid derivatives, employing processes like the Strecker synthesis starting from intermediates such as 4-methoxy-1-amino-cyclohexane-carbonitrile.^[7] This approach yielded mixtures of isomers, with the biologically active form identified through iterative optimization, as detailed in subsequent patents like WO 02/002532.^[7] Researchers, including R. Fischer and H.-C. Weiß, refined the structure to emphasize the tetramic acid scaffold's spirocyclic elements, which contributed to its systemic properties.^[7] A key developmental milestone occurred around 2005, when laboratory testing of lead compound 1b demonstrated excellent efficacy against sucking pests, such as the green peach aphid (Myzus persicae), approaching the performance of established insecticides like imidacloprid.^[7] This validation shifted focus toward its potential as a specialized insecticide within the keto-enol class, paving the way for further refinement.^[7] The compound was later commercialized by Bayer CropScience under the brand name Movento.^[6]

Commercial introduction

Spirotetramat received its first commercial regulatory approval in Tunisia in 2007, marking the initial market entry for this novel insecticide developed by Bayer CropScience.^[2] This approval paved the way for broader commercialization, with the product launched under the primary brand name Movento, an oil dispersion formulation containing 150 g/L spirotetramat.^[8] Following closely, the United States Environmental Protection Agency granted registration for Movento in 2008, enabling its use in North American agriculture.^[9] Bayer expanded the product's portfolio with the introduction of Ultor, another spirotetramat-based insecticide, initially approved by the EPA in 2008 for applications including vegetable crops, though the approval was vacated in 2009 and re-approved in 2010 following a federal court challenge over risks to pollinators.^[10]^[11] By 2010, Movento had achieved a global rollout, becoming available in over 70 countries including Brazil, Argentina, Mexico, Australia, and several European nations.^[12] This rapid international adoption was supported by its origins in tetramic acid derivative synthesis, which facilitated efficient scaling for agricultural markets.^[2] In 2025, Bayer announced it would not seek renewal of approvals for spirotetramat products like Movento in the European Union, leading to the expiration of authorizations by mid-2025, while approvals continue in other regions such as Great Britain until at least 2029.^[13]^[2] From its inception, spirotetramat was positioned as a key component in integrated pest management (IPM) programs, emphasizing selective control to minimize impacts on beneficial insects.^[14] Early adoption focused on high-value crops, particularly in cotton-producing regions where it addressed sucking pests like whiteflies, and in citrus orchards for managing aphids and scales, enhancing overall crop protection strategies without disrupting natural predators.^[15]

Chemical identity

Molecular structure

Spirotetramat has the molecular formula C₂₁H₂₇NO₅, CAS number 203313-25-1, and a molar mass of 373.45 g/mol.^[16] Its IUPAC name is cis-3-(2,5-xylyl)-4-(ethoxycarbonyloxy)-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one, also expressed as (5S,8S)-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate.^[16]^[2] The molecule possesses a spirocyclic core based on a 1-azaspiro[4.5]decane system, where a five-membered lactam ring shares a spiro carbon with a six-membered cyclohexane ring, substituted at the 3-position with a 2,5-dimethylphenyl group and at the 8-position with a methoxy group.^[16] This structure includes a tetramic acid moiety, consisting of a five-membered ring with an α,β-unsaturated ketone and an adjacent amide functionality, which defines its classification as a tetramic acid derivative.^[17] The overall architecture can be visualized as a central spiro junction linking the heterocyclic tetramic acid unit to the carbocyclic ring, with the ethyl carbonate ester at the 4-position contributing to its lipophilicity.^[16]

Physical and chemical properties

Spirotetramat is a white to off-white crystalline solid in its technical form.^[16] It has a melting point of 142 °C at 99.2% purity.^[16] The compound exhibits low solubility in water, with values ranging from 19.1 mg/L at pH 9 to 33.5 mg/L at pH 4, and 29.9 mg/L at pH 7 and 20 °C.^[16] In contrast, it shows higher solubility in organic solvents at 20 °C, such as 67 g/L in ethyl acetate, 100–120 g/L in acetone, and 200–300 g/L in dimethyl sulfoxide.^[16] Its octanol-water partition coefficient (log Pow) is 2.5 at pH 7 and 20 °C, indicating moderate lipophilicity that influences its distribution in biological and environmental systems.^[16] Spirotetramat also displays low volatility, with a vapor pressure of 5.6 × 10−9 Pa at 20 °C.^[16] Regarding stability, spirotetramat is non-persistent in soil under aerobic conditions, with a laboratory DT50 of 0.19 days at 20 °C and a field DT50 of 0.7 days.^[2] It undergoes hydrolysis with a DT50 of 13 days at pH 7 and 20 °C, producing the enol degradate as the primary product.^[16]

Mechanism of action

Biochemical inhibition

Spirotetramat functions as an inhibitor of acetyl-CoA carboxylase (ACC), a key enzyme in the lipid biosynthesis pathway that is crucial for the growth, development, and reproduction of insects. This disruption prevents the carboxylation of acetyl-CoA to malonyl-CoA, the first committed step in fatty acid synthesis, thereby halting the production of lipids essential for membrane formation and energy storage in target pests. Classified under IRAC mode of action group 23 as a lipid biosynthesis inhibitor, spirotetramat's activity is highly specific to insects, particularly affecting their metabolic processes without broadly impacting non-target organisms in the same manner.^[18]^[19] The inhibited reaction catalyzed by ACC can be represented as:

\text{Acetyl-CoA} + \text{HCO}_3^- + \text{ATP} \xrightarrow{\text{ACC}} \text{Malonyl-CoA} + \text{ADP} + \text{P}_i

By blocking this step, spirotetramat induces a cascade of physiological disruptions in insects, leading to severe metabolic stress.^[20] In juvenile stages, the compound primarily manifests its effects through growth inhibition and incomplete ecdysis, where nymphs or larvae fail to properly molt due to insufficient lipid reserves for new cuticle formation. This results in reduced fecundity, as surviving adults produce fewer offspring, and starvation-like symptoms characterized by lethargy and halted development from lipid depletion. These outcomes are most pronounced in piercing-sucking insects, such as aphids and whiteflies, where ingestion of the compound triggers rapid metabolic interference. Notably, spirotetramat exhibits no significant cross-resistance to major insecticide classes like neonicotinoids or organophosphates, owing to its novel target site.^[21]^[6]^[22]

Systemic translocation

Spiro tetramat exhibits ambimobile systemic action within plants, enabling translocation through both the xylem and phloem tissues. Following application, the compound moves acropetally via the xylem for upward transport from roots or lower leaves, while phloem-mediated redistribution allows bidirectional movement, including basipetal flow to roots and emerging tissues.^[6]^[23] This dual-pathway mobility ensures comprehensive distribution to all plant parts, including new growth areas that develop post-treatment, providing prolonged protection against pests.^[6] Upon uptake, spirotetramat undergoes rapid in planta conversion to its active enol metabolite, spirotetramat-enol (also known as BYI 08330-enol), primarily through hydrolytic cleavage. This metabolic transformation occurs within plant tissues shortly after absorption, with the enol form accounting for a significant portion of the total residues, such as approximately 45% in shoot tissues after several days.^[23]^[6] The enol metabolite, being more polar and acidic, exhibits enhanced phloem mobility compared to the parent compound, facilitating its accumulation in younger leaves and other metabolically active sites.^[23] This conversion not only activates the insecticide but also improves its persistence and tissue penetration, contributing to effective pest control over extended periods.^[6] Uptake of spirotetramat occurs primarily through foliar application, where it penetrates leaf cuticles and enters the vascular system, though root absorption is also feasible from soil or hydroponic solutions.^[6]^[23] Once translocated, the compound and its metabolites reach the feeding sites of phloem- or xylem-feeding pests, such as aphids and whiteflies, primarily through ingestion rather than contact, allowing the active enol form to interfere with lipid biosynthesis in target insects.^[6] This targeted distribution minimizes exposure to non-target plant areas while maximizing efficacy against hidden or mobile sucking pests.^[6]

Agricultural applications

Target pests and crops

Spirotetramat is primarily effective against a range of sucking pests, including aphids such as the green peach aphid (Myzus persicae) and cotton aphid (Aphis gossypii), whiteflies like the silverleaf whitefly (Bemisia tabaci), psyllids including the Asian citrus psyllid (Diaphorina citri), mealybugs such as the vine mealybug (Planococcus ficus), and various soft scale insects.^[1]^[2] It demonstrates particularly high efficacy against nymphal and immature stages of these pests, with studies showing significant reductions in fecundity and fertility in aphids and whiteflies feeding on treated plants.^[24]^[6] The insecticide is registered for use on over 100 crops globally, encompassing citrus fruits, pome and stone fruits (such as apples, pears, peaches, and cherries), grapes, tree nuts including walnuts, a variety of vegetables like brassicas (broccoli, cabbage, kale), potatoes, tomatoes, and peppers, as well as field crops such as cotton and soybeans.^[1]^[25] It is commonly integrated into integrated pest management (IPM) programs to manage resistant pest strains, providing a valuable tool for sustainable control of these insects.^[26] Spirotetramat is generally less effective against mobile adult stages of target pests due to its reliance on ingestion by feeding individuals.^[6] Documented cases of resistance have emerged in some populations, such as in A. gossypii, where a resistant strain exhibited 441.26-fold resistance in adults and 11.97-fold in nymphs compared to susceptible strains.^[27]

Application guidelines

Spirotetramat is typically formulated as a 240 g/L suspension concentrate, such as in the commercial product Movento 240 SC.^[28] It is applied as a foliar spray at rates ranging from 96 to 400 mL/ha, with the specific rate depending on the crop, pest pressure, and regional guidelines.^[29]^[28] Up to three applications per season are recommended, separated by a minimum interval of 7 days to allow for effective systemic uptake while minimizing residue accumulation.^[28] The withholding period before harvest varies by crop but is generally 3 to 7 days to ensure safe consumption.^[30] For optimal efficacy, applications should be timed early in the growing season when targeting the nymph stages of sucking pests, as the compound's systemic action is most pronounced during active plant growth and early pest development.^[6] This approach maximizes control while aligning with the insecticide's translocation properties in the plant vascular system.^[31] Spirotetramat integrates well into integrated pest management (IPM) strategies and should be alternated with insecticides from different modes of action to delay resistance development in target populations.^[32] During preparation, the formulation requires thorough mixing with a non-ionic spreading and penetrating adjuvant at recommended rates, and applicators must follow precautions to minimize off-target drift, such as using low-pressure nozzles and applying under calm wind conditions.^[30]

Regulation and approvals

Global regulatory status

Sprirotetramat received its initial regulatory approval in Tunisia in 2007. This was followed by approval from the United States Environmental Protection Agency (EPA) in 2008 for use as an insecticide. In the European Union, approval was granted through Commission Implementing Regulation (EU) No 1177/2013, which took effect on 1 May 2014 specifically for representative uses on citrus and lettuce following the European Food Safety Authority (EFSA) peer review. In Australia, the Australian Pesticides and Veterinary Medicines Authority (APVMA) approved spirotetramat in the 2010s for application on brassica vegetables and other crops. As of 2025, spirotetramat is approved for use in more than 50 countries worldwide, including Canada, China, Mexico, Morocco, New Zealand, and Turkey. Within the European Union, it holds national approvals in numerous Member States, such as Austria, Belgium, Bulgaria, France, and Germany, often through mutual recognition or national regulations, with Austria serving as the rapporteur Member State. However, it lacks EU-wide approval under Regulation (EC) No 1107/2009 after the expiration of its previous authorization on 30 April 2024, as the manufacturer, Bayer, chose not to pursue renewal. In Great Britain, spirotetramat remains approved under the Control of Pesticides Regulations (COPR) with inclusion set to expire on 31 July 2029. The EFSA's 2013 peer review evaluated spirotetramat for its representative uses on citrus and lettuce, supporting the initial EU approval. No major global bans have been enacted, though regulatory bodies conduct periodic re-evaluations, including assessments of potential risks to pollinators. Commercial launches of spirotetramat-based products, such as Movento, have been directly linked to these regulatory milestones.

Residue limits and guidelines

The residue definition for spirotetramat in plant commodities for enforcement purposes is the sum of spirotetramat and its enol metabolite (BYI 08330-enol), expressed as spirotetramat; for dietary risk assessment and exposure purposes, it includes the ketohydroxy metabolite as well.^[33] Maximum residue limits (MRLs) for spirotetramat have been established by the Codex Alimentarius Commission and harmonized in part with U.S. Environmental Protection Agency (EPA) tolerances. Under Codex, the MRL for brassica leafy vegetables is 7 mg/kg, while flowerhead brassicas (including Brussels sprouts) are set at 1 mg/kg; for fruits, values range from 0.5 mg/kg for citrus to 2 mg/kg for grapes.^[33]^[34] The EPA tolerances align closely, with 8.0 mg/kg for brassica leafy greens (subgroup 5B), 2.5 mg/kg for brassica head and stem (subgroup 5A, including Brussels sprouts), 0.60 mg/kg for citrus fruits (group 10-10), and 2.0 mg/kg for grapes.^[34] Dietary exposure assessments for spirotetramat utilize an acceptable daily intake (ADI) of 0.05 mg/kg body weight per day and an acute reference dose (ARfD) of 1.0 mg/kg body weight, established by the Joint FAO/WHO Meeting on Pesticide Residues (JMPR).^[35] These reference values support low chronic and acute risk from residues, as international estimates of short-term intake (IESTI) for relevant population groups are below 10% of the ARfD, and long-term intake (IEDI) represents 2–20% of the ADI.^[35] The rapid dissipation of spirotetramat in soil, with a half-life (DT50) of 0.3–1.0 days under field conditions, further minimizes residue carryover and environmental persistence risks.^[6]

Safety and toxicology

Mammalian toxicity

Spirotetramat exhibits low acute toxicity in mammals via oral and dermal routes, with an oral LD₅₀ greater than 2000 mg/kg body weight (bw) in rats and a dermal LD₅₀ greater than 2000 mg/kg bw in rats and rabbits.^[28]^[36] Inhalation toxicity is also low, with an LC₅₀ greater than 4.183 mg/L air (4-hour exposure) in rats.^[37] The compound is an eye irritant (EPA Toxicity Category II), causing serious eye irritation but reversible effects in animal studies, and acts as a skin sensitizer, potentially leading to allergic reactions upon repeated contact.^[38] Possible respiratory effects include irritation, observed in acute inhalation exposures.^[39] Chronic exposure studies indicate that spirotetramat is non-carcinogenic, with no evidence of tumor formation in long-term rat and mouse bioassays.^[40] For reproductive and developmental toxicity, a no-observed-effect level (NOEL) of 5 mg/kg bw/day was established based on dog studies showing effects such as delayed fetal growth at higher doses.^[28] The acceptable daily intake (ADI) is set at 0.05 mg/kg bw/day, derived from this NOEL with a 100-fold safety factor to account for inter- and intraspecies variability.^[41] Primary exposure routes for mammals, particularly in occupational settings, are dermal contact and inhalation during handling and application, with ocular exposure also possible.^[28] In Australia, spirotetramat is classified as a Schedule 6 poison under the Standard for the Uniform Scheduling of Medicines and Poisons, reflecting its irritant and sensitizing properties along with potential reproductive risks, corresponding to risk phrases R36 (irritating to eyes), R43 (may cause sensitization by skin contact), R62 (possible risk of impaired fertility), and R63 (possible risk to the unborn child).^[28] Its low environmental persistence helps limit long-term mammalian exposure risks.^[2]

Ecotoxicological effects

Spirotetramat exhibits moderate acute toxicity to fish (96-hour LC₅₀ 1.96-2.84 mg/L for species such as rainbow trout and bluegill sunfish) and algae, but low acute toxicity to daphnia (48-hour EC₅₀ >42.7 mg/L for Daphnia magna), indicating potential risks from direct exposure depending on concentrations.^[9] For invertebrates, chronic exposure shows moderate effects with a 21-day NOEC of 2.0 mg/L for reproduction and growth.^[2] Algal species like Skeletonema costatum display moderate sensitivity, with a 72-hour ErC₅₀ of 0.96 mg/L.^[2] Potential risks from agricultural runoff exist due to foliar application, but these are mitigated by the compound's rapid degradation in water and soil, limiting long-term exposure.^[28] In terrestrial ecosystems, spirotetramat poses low acute risks to key non-target species. For bees, contact and oral LD₅₀ values exceed 100 μg/bee and 107.3 μg/bee, respectively, classifying it as practically non-toxic under acute scenarios, though sublethal effects on brood may occur at higher chronic exposures.^[28] Birds experience negligible acute toxicity, with oral LD₅₀ >2000 mg/kg body weight in species like bobwhite quail.^[2] Earthworms show low acute sensitivity (14-day LC₅₀ >1000 mg/kg dry soil), but moderate chronic impacts are noted, particularly from metabolites like spirotetramat-enol, with reproduction NOEC at 32 mg/kg dry soil.^[28] Predatory mites exhibit variable responses, with moderate harm to some species (IOBC categories III-IV) but compatibility with others like Neoseiulus californicus in integrated pest management contexts.^[19] Overall, spirotetramat's environmental profile supports low ecological impact due to limited bioaccumulation potential, evidenced by a log Pₒw of 2.51 and bioconcentration factor (BCF) below 100, preventing significant trophic magnification.^[2] Its low leaching potential, indicated by a GUS index of -0.24, minimizes groundwater contamination risks.^[2] The compound's selectivity for sucking pests, combined with rapid soil degradation (DT₅₀ 0.08–0.33 days under aerobic conditions), enhances its suitability for integrated pest management while reducing broader ecosystem disruption.^[28]

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