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Spinetoram

Spinetoram is a semi-synthetic insecticide belonging to the spinosyn class, derived through chemical modification of spinosad—a natural product fermented from the soil bacterium Saccharopolyspora spinosa—and consisting of spinetoram J (3'-O-ethyl-3',4'-O-(1-methylethylidene)-spinosyn J) and spinetoram L (3'-O-ethyl-3',4'-O-(1-methylethylidene)-spinosyn L) in an approximate 3:1 ratio.^[1]^[2] With the molecular formula C₄₂H₆₉NO₁₀, it exhibits a macrocyclic structure featuring a tetracyclic aglycone core linked to D-forosamine and a modified rhamnose sugar moiety, enhancing its stability and potency over the parent compound.^[3] Developed by Dow AgroSciences in the early 2000s using a combination of microbial genetics, quantitative structure-activity relationship modeling, and synthetic chemistry, spinetoram was designed to address limitations in spinosad's residual activity and spectrum while maintaining its favorable safety profile for non-target organisms.^[4] As a broad-spectrum agent, spinetoram targets a range of insect pests, including lepidopterans (such as moths and caterpillars), thrips, and leaf miners, through both contact and ingestion routes, with translaminar movement in plant tissues but no systemic activity.^[5] Its mode of action involves allosteric modulation of nicotinic acetylcholine receptors and disruption of γ-aminobutyric acid-gated chloride channels in the insect nervous system, leading to hyperexcitation, paralysis, and death, and classifying it under Insecticide Resistance Action Committee (IRAC) Group 5.^[2] Registered by the U.S. Environmental Protection Agency since 2007 for use on crops like fruits, vegetables, cotton, and ornamentals, spinetoram offers rapid knockdown, a short pre-harvest interval, and reduced application rates compared to conventional insecticides, contributing to its recognition in the 2008 Presidential Green Chemistry Challenge Award for designing greener chemicals with lower environmental persistence and toxicity to mammals, birds, and beneficial insects.^[6]

History and Development

Discovery

Spinetoram's precursors originated from the soil actinomycete bacterium Saccharopolyspora spinosa, which was isolated in 1982 during a systematic screening program for novel microbial natural products with insecticidal potential conducted by researchers at Eli Lilly and Company (predecessor to Dow AgroSciences). The bacterium was discovered in soil samples collected from an abandoned sugar rum distillery on the island of Vieques in the U.S. Virgin Islands, as part of a broader effort to identify actinomycetes capable of producing bioactive metabolites through fermentation.^[7]^[8] Between 1982 and 1985, Dow AgroSciences screened over 20,000 microbial cultures, leading to the identification of insecticidal activity in fermentations of S. spinosa. Key researchers, including Howard A. Kirst, Glenn D. Thompson, and the natural products discovery team, isolated the active compounds, named spinosyns A and D, as the primary components responsible for the bioactivity; these macrolide glycosides were produced via aerobic fermentation of the bacterium.^[4]^[9]^[8] Spinetoram emerged as a semi-synthetic derivative of these spinosyns, achieved through targeted chemical modifications to improve spectrum and residual activity while retaining the natural core structure. Initial patents covering the spinosyns and their fermentation-based production were filed by Dow in the late 1980s, with U.S. Patent No. 5,362,634 (priority date 1989) detailing the process for obtaining the A83543 compounds (spinosyns).^[4]^[10]

Commercial Development

Spinetoram was developed by Dow AgroSciences as a semi-synthetic insecticide building on the natural spinosyns discovered earlier, involving targeted chemical modifications to enhance stability, residual activity, and efficacy against a broader spectrum of pests. Specifically, it consists of a 50:50 mixture of two key components: 3'-O-ethyl-5,6-dihydrospinosyn J (spinetoram J) and 3'-O-ethylspinosyn L (spinetoram L), derived from spinosyns J and L through selective ethoxylation at the 3' position of the forosamine moiety and hydrogenation to reduce the 5,6 double bond in the J factor. These modifications were patented by Dow AgroSciences in 2001 under CAS number 935545-74-7 for the mixture, addressing limitations in photostability and rainfastness observed in earlier spinosyn formulations.^[11]^[2]^[4] The commercial timeline began with U.S. Environmental Protection Agency (EPA) registration of spinetoram technical on September 28, 2007, under the Reduced Risk Pesticide Program, enabling market launch as Delegate™ WG for agricultural applications targeting lepidopterous pests in crops like fruits, vegetables, and cotton. This was followed by expanded approvals, including Radiant™ SC for similar uses, with tolerances established for residues in various commodities. In 2013, spinetoram entered the veterinary market with the introduction of Cheristin®, a topical spot-on formulation for flea control in cats, leveraging its rapid knockdown and low mammalian toxicity for household pest management.^[6]^[12]^[13]^[14]^[15] Commercial production of spinetoram relies on semi-synthetic fermentation, starting with the aerobic cultivation of a genetically modified strain of Saccharopolyspora spinosa engineered to yield primarily spinosyns J and L (up to 90% of total spinosyns), followed by purification and chemical processing steps including ethylation and selective hydrogenation. Early scalability challenges included optimizing fermentation yields and minimizing byproducts from the genetic block mutation, as well as reducing solvent volumes and waste in the multi-step synthesis, which initially posed cost barriers for large-scale output. By the 2010s, process improvements guided by green chemistry principles—such as aqueous hydrogenation and efficient extraction—achieved significant cost reductions, enabling broader market adoption with application rates one-tenth those of conventional insecticides while maintaining environmental safety.^[2]^[16]^[4]^[6]

Chemical Structure and Properties

Molecular Composition

Spinetoram is a semi-synthetic insecticide defined as a mixture consisting primarily of two closely related compounds: 3'-O-ethyl-5,6-dihydrospinosyn J (also known as spinetoram-J or XDE-175-J) at approximately 70% w/w and 3'-O-ethylspinosyn L (spinetoram-L or XDE-175-L) at approximately 30% w/w.^[2]^[17] This ratio can vary slightly in technical material, ranging from 70:30 to 90:10 for J:L.^[17] Both components share a core molecular formula of C₄₂H₆₉NO₁₀ for spinetoram-J, while spinetoram-L is C₄₃H₆₉NO₁₀, reflecting minor differences in their aglycone portions.^[3]^[18] The molecular structure of spinetoram is a tetracyclic macrolide derived from natural spinosyns produced by Saccharopolyspora spinosa, featuring a 21-carbon macrocyclic lactone ring system as the core backbone.^[19] This macrocycle is fused into a tetracyclic arrangement and glycosidically linked at C-9 and C-17 to two deoxysugars: D-forosamine (a 2,3,6-trideoxy-3-(dimethylamino)-L-lyxo-hexose) and a modified rhamnose (specifically, 3-O-ethyl-2,4-di-O-methyl-α-L-rhamnopyranose).^[19] The ethyl modification at the 3' position of the rhamnose and the partial hydrogenation in spinetoram-J enhance stability compared to the parent spinosyns.^[16] In commercial formulations, spinetoram is typically provided as a suspension concentrate (SC) with 11.7% active ingredient (w/v), ensuring high purity of the technical material at a minimum of 830 g/kg.^[18]^[20] Isomeric variations are minimal, with the defined J and L factors constituting the active mixture, and purity standards maintained to exclude significant impurities.^[18]

Physical and Chemical Properties

Spinetoram is a semi-synthetic derivative of the spinosyn core structure and appears as an off-white solid with a musty odor.^[18]^[21] It melts at 107.1 °C and decomposes before boiling, with a degradation point around 293 °C.^[18] The compound exhibits low solubility in water, approximately 29 mg/L at pH 7 and 20 °C, but is highly soluble in polar organic solvents such as methanol, acetone, and ethyl acetate (all >250 g/L at 20 °C), and moderately soluble in n-heptane (61 g/L).^[18]^[21] This profile, combined with an octanol-water partition coefficient (log K_ow) of 4.2 at pH 7 and 20 °C, indicates moderate lipophilicity, facilitating its partitioning into organic phases in environmental and biological systems.^[18]^[2] Spinetoram has a very low vapor pressure of 5.7 × 10^-5 Pa at 20 °C, rendering it non-volatile under typical conditions.^[18] It possesses a pK_a of 7.7 at 25 °C, consistent with weak acidity.^[18] The compound is stable to hydrolysis across pH 5–9 at 25 °C, with no significant degradation observed (DT₅₀ > 1 year at pH 7, 20 °C), though it undergoes rapid aqueous photolysis under simulated sunlight (DT₅₀ ≈ 0.4 days at pH 7).^[18]^[2] In practical applications, spinetoram is commonly formulated as suspension concentrates, emulsifiable concentrates, or water-dispersible granules to enhance handling and efficacy in pest control.^[21]^[22]

Mechanism of Action

Biological Target

Spinetoram primarily binds to nicotinic acetylcholine receptors (nAChRs) in the central nervous system of insects, acting as an allosteric modulator that causes persistent activation and overstimulation of these receptors. This interaction occurs at a distinct site on the α6 subunit of the nAChR, leading to hyperexcitation and disruption of normal neural signaling without causing receptor desensitization.^[23] Studies using genetic knockouts and binding assays have confirmed the α6 subunit as the major target site for spinosyns like spinetoram, with mutations in this subunit conferring high levels of resistance.^[24] As a secondary site of action, spinetoram interacts with GABA-gated chloride channels, where it modulates ion flow to further disrupt inhibitory neural transmission in insects.^[25] This dual targeting enhances its insecticidal efficacy by combining excitatory and inhibitory disruptions. Spinetoram exhibits higher affinity for insect nAChRs compared to mammalian counterparts, contributing to its selectivity and low toxicity in vertebrates.^[26] Unlike pyrethroids, spinetoram shows no significant binding to voltage-gated sodium or calcium channels, avoiding the prolongation of action potentials characteristic of those insecticides. This specificity underscores its unique mode of action within the spinosyn class.

Mode of Insecticidal Activity

Spinetoram exerts its insecticidal effects by binding to nicotinic acetylcholine receptors (nAChRs) and gamma-aminobutyric acid (GABA) channels in the insect nervous system, leading to hyperexcitation, involuntary muscle contractions, tremors, prostration, paralysis, and eventual lethargy within hours of exposure via contact or ingestion.^[27]^[1] This neurotoxic cascade disrupts normal nerve function, causing rapid cessation of feeding and movement, with mortality typically occurring in 1-3 days for larval stages.^[16]^[27] The compound demonstrates translaminar activity, allowing it to penetrate leaf tissues for effective control through both contact and ingestion routes.^[16]^[28] Residual effects persist for 14-28 days on foliage, providing prolonged protection against pests.^[29] For key Lepidoptera pests, LC50 values range from 0.1-1 ppm, illustrating its potency at low concentrations.^[16]^[1] Resistance to spinetoram can develop through target-site mutations in nAChR genes, such as the G275E substitution, which alters receptor sensitivity.^[30]^[31] However, this resistance typically shows low cross-resistance to other classes like organophosphates, supporting its integration into resistance management programs.^[16]^[32]

Applications and Uses

Agricultural Pest Control

Spinetoram plays a significant role in agricultural pest control, targeting key insect pests across diverse cropping systems through foliar and soil applications. It exhibits high efficacy against Lepidoptera species, such as the codling moth (Cydia pomonella) in apples and the diamondback moth (Plutella xylostella) in brassica vegetables, as well as Thysanoptera like thrips (Thrips spp.) in cotton and onions, and select Coleoptera including the Colorado potato beetle (Leptinotarsa decemlineata) in potatoes. These pests can cause substantial yield losses, and spinetoram provides rapid knockdown and control by disrupting nicotinic acetylcholine receptors in the insect nervous system via its neurotoxic mode of action. Field trials have demonstrated over 90% control rates against lepidopteran larvae, such as Spodoptera litura, when applied at recommended rates.^[33]^[34]^[35] The insecticide is registered for use on a wide array of crops globally, including pome fruits like apples, stone fruits, grapes, cotton, and various vegetables such as brassicas, leafy greens, and root crops, enabling its integration into production systems for over 50 crop types in regions like North America, Europe, and Asia. Application rates typically range from 50 to 200 g active ingredient per hectare, depending on the crop, pest pressure, and growth stage, with higher rates used for heavy infestations of lepidopteran larvae. For example, rates of 100-140 g ai/ha effectively suppress codling moth in pome fruits, while 60-120 g ai/ha control thrips in cotton seedlings. Efficacy studies in cabbage ecosystems have shown spinetoram at 60 g ai/ha achieving greater than 80% reduction in diamondback moth and cabbage looper populations across multiple applications.^[29]^[33]^[36]^[37] Spinetoram's compatibility with integrated pest management (IPM) programs stems from its selective toxicity, exhibiting minimal impact on beneficial predatory insects such as ladybugs and lacewings, which helps preserve natural enemy populations for sustained pest suppression. Although moderately toxic to bees under direct exposure, its low residue levels and rapid degradation reduce risks when applications avoid bloom periods, allowing pollinator activity in treated fields. Compared to its predecessor spinosad, spinetoram offers a broader spectrum of activity against thrips and certain leafminers, along with enhanced photostability for longer residual control, often extending efficacy by several days in field conditions.^[5]^[38]^[29]^[39]

Stored Grain Protection

Spinetoram serves as an effective protectant for stored grains, targeting major insect pests such as the rice weevil (Sitophilus oryzae) and lesser grain borer (Rhyzopertha dominica). It exhibits activity against Coleoptera orders commonly infesting commodities like wheat, maize, and rice. The insecticide is applied as dusts or liquid formulations directly to the grain mass at low concentrations of 1–5 ppm, ensuring even distribution for comprehensive coverage.^[40] Laboratory studies confirm spinetoram's high efficacy, achieving up to 100% mortality of adults from these species after 14 days of exposure at doses as low as 0.1–1 ppm on wheat. A 2023 study highlighted spinetoram as a promising grain protectant with high efficacy against several stored-product insect species, offering a potential alternative to traditional treatments like phosphine, and low mammalian toxicity.^[41]^[42] Residual activity of spinetoram persists for up to 8 months under typical storage conditions (e.g., 25–30°C and 60–70% relative humidity), providing extended protection against reinfestation while maintaining grain integrity. In practice, it is incorporated into integrated pest management programs for storage facilities, complementing aeration practices that cool grain to below 15°C to suppress insect activity and routine monitoring with traps or probes to detect early pest presence.

Veterinary and Household Uses

Spinetoram is employed in veterinary applications primarily through topical spot-on formulations for ectoparasite control in companion animals. The product Cheristin®, containing 11.8% spinetoram, is approved for treating and preventing flea infestations (Ctenocephalides felis) in cats and kittens at least 8 weeks old and weighing a minimum of 1.8 pounds.^[43] Applied monthly to the skin at the base of the skull, it provides up to 30 days of protection by killing adult fleas upon contact, with initial mortality occurring within 30 minutes and 98-100% efficacy achieved within 12 hours.^[44] This formulation also alleviates clinical signs of flea allergy dermatitis, significantly reducing symptoms such as pruritus and alopecia in affected cats.^[45] In livestock, spinetoram's use remains limited but includes topical applications for managing ectoparasites like flies and lice, leveraging its activity against Diptera and other pests. Formulations have been developed to provide systemic control of infestations in animals, with low toxicity and biodegradability supporting its potential in veterinary ectoparasiticide programs.^[46]^[47] For household pest management, spinetoram is available in products such as Radiant SC, which targets thrips and whiteflies on ornamental plants indoors and in home gardens. These applications suppress sap-feeding insects on foliage, offering effective control without broad-spectrum disruption to beneficial organisms when used as directed.^[48] Emerging research in 2025 has revealed spinetoram's antifungal activity against phytopathogens affecting tea plants, vegetables, and fruit trees, achieving up to 70.7% disease reduction in in vivo trials on tomato leaves and fruits. This broad-spectrum efficacy suggests opportunities for expanding its role in integrated pest management within households, potentially combining insecticidal and fungicidal benefits for ornamental and indoor plant care.^[49]

Safety, Toxicology, and Environmental Impact

Human and Animal Toxicity

Spinetoram demonstrates low acute toxicity in mammals. In rats, the acute oral LD₅₀ exceeds 5000 mg/kg body weight, the dermal LD₅₀ is greater than 5000 mg/kg, and the 4-hour inhalation LC₅₀ surpasses 5.44 mg/L air.^[17] These values indicate minimal risk from single exposures via common routes. The compound is non-irritating to rabbit skin and eyes, with transient ocular effects resolving within 24 hours, and it does not induce dermal sensitization in standard mouse models.^[17] Chronic exposure studies reveal limited effects at relevant doses. In a 2-year dietary study in rats, the no-observed-adverse-effect level (NOAEL) was 250 ppm, equivalent to 10.8 mg/kg bw/day in males and 13.2 mg/kg bw/day in females, with higher doses causing thyroid vacuolation and lymphoid depletion.^[17] No carcinogenic potential was evident in 2-year rat or 18-month mouse oncogenicity studies.^[50] Reproductive toxicity assessments, including multigeneration rat studies, established a NOAEL of 10 mg/kg bw/day for parental, reproductive, and offspring effects, with no developmental toxicity observed in rats (NOAEL 300 mg/kg bw/day) or rabbits (NOAEL 60 mg/kg bw/day).^[17] In veterinary applications, spinetoram is formulated as a topical spot-on for flea control in cats and is safe at labeled doses, with no reported reproductive or oncogenic risks.^[43] It is not approved for dogs due to species-specific sensitivity concerns, though general mammalian toxicity data suggest low risk. Human exposure primarily occurs occupationally through dermal contact and inhalation during pesticide application, where low absorption and rapid clearance minimize hazards.^[17] This profile stems from spinetoram's selectivity for insect nicotinic acetylcholine receptors over mammalian ones.^[51]

Environmental Fate and Effects

Spinetoram degrades relatively rapidly in soil under aerobic conditions, with laboratory DT50 values ranging from 1 to 9 days, primarily through microbial metabolism and photolysis.^[52] Its strong adsorption to soil particles, indicated by Koc values of 10,000 to 20,000 mL/g, results in low mobility and minimal leaching potential to groundwater. In aquatic environments, spinetoram exhibits fast dissipation, with DT50 values less than 1 day due to rapid photolysis and hydrolysis under natural sunlight conditions.^[53] Regarding impacts on non-target species, spinetoram shows high acute contact toxicity to honey bees, with an LD50 of approximately 0.024 µg/bee, though risks can be mitigated by applying it during times when bees are not actively foraging. Recent 2024-2025 studies indicate sublethal effects, including disrupted larval development, altered antioxidant enzyme activities, and behavioral changes at low exposure levels.^[54]^[55] It is highly toxic to aquatic invertebrates, such as Daphnia magna, with a 48-hour EC50 of 0.228 mg/L, potentially affecting survival, reproduction, and population dynamics in freshwater ecosystems.^[56] In contrast, it poses low toxicity to fish, with 96-hour LC50 values exceeding 100 mg/L for species like rainbow trout.^[57] Bioaccumulation of spinetoram in aquatic organisms is low, with bioconcentration factors (BCF) generally below 10, indicating limited potential for trophic magnification in food chains.^[53] Recent 2025 research has revealed spinetoram's unexpected antifungal activity against plant pathogens, suggesting possible benefits for integrated disease management, but it also raises concerns about adverse effects on beneficial soil microbial communities, including shifts in diversity and function.^[49]

Regulatory Status

Spinetoram was first registered by the U.S. Environmental Protection Agency (EPA) on September 28, 2007, under the Reduced Risk Pesticide Program due to its favorable safety profile compared to conventional alternatives.^[5] The EPA has established tolerances for spinetoram residues in numerous commodities to ensure safe use, including 0.20 ppm for pome fruits such as apples and 1.5 ppm for cotton gin byproducts.^[58] In 2015, the EPA updated these tolerances as part of ongoing registration reviews without imposing major changes to the product's approval status.^[50] Subsequent amendments in 2021 and 2023 expanded tolerances to additional crops, such as leafy greens and spices, reflecting continued alignment with agricultural needs.^[59]^[60] In the European Union, spinetoram received approval as an active substance under Regulation (EC) No 1107/2009, which governed its use in plant protection products until expiration on June 30, 2024, with no renewal application submitted by industry stakeholders. Following the approval lapse, existing maximum residue levels (MRLs) based on EU uses are subject to revocation, though some may persist for imported goods under transitional provisions.^[61] Spinetoram is banned or restricted in organic farming contexts within the EU owing to its semi-synthetic derivation from natural spinosyns, which does not qualify it for inclusion on the list of permitted substances in organic production. The World Health Organization classifies spinetoram as unlikely to present an acute hazard in normal use (Class U).^[62] For international trade, the Codex Alimentarius Commission has set harmonized MRLs for spinetoram in key crops to minimize trade barriers, including 0.5 mg/kg for pitaya and 4 mg/kg for dried chili peppers.^[63] Post-2020 regulatory updates, particularly in the U.S. and aligned markets, have incorporated resistance management requirements into product labeling, mandating rotation with unrelated modes of action to sustain efficacy against target pests. This low mammalian toxicity profile supports its continued classification as a reduced-risk option in approved jurisdictions.

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Radiant® SC Insecticide - Corteva Agriscience
This product delivers effective pest control against the following: Armyworm; Beetle; Cabbageworm; Caterpillar; Corn Borer; Cutworm; Drosphilia; Earworm ...
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Spinetoram, a Widely Used Insecticide, Demonstrates Strong ...
Sep 1, 2025 · This dual pesticidal-fungicidal activity positions spinetoram as a promising lead compound for integrated pest/disease management strategies and ...
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Spinetoram; Pesticide Tolerances - Federal Register
Dec 24, 2015 · There is no evidence of neurotoxicity, developmental/reproductive toxicity, immunotoxicity, mutagenicity, or carcinogenicity from spinetoram or ...
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[PDF] Spinetoram - Food and Agriculture Organization of the United Nations
Spinetoram is a macrocyclic lactone insecticide. It acts by causing ... Carbon dioxide was evolved slowly from all soils and accounted for 5.0–35% and ...
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[PDF] European Cherry Fruit Fly (Rhagoletis cerasi) Cooperative Control ...
Oct 4, 2022 · Acetamiprid is stable to hydrolysis but undergoes aqueous photolysis (half-life = 34 days) (USEPA 2017a). In anaerobic soil, the DT50 is ...
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[PDF] ERC2008-01 Evaluation Report - à www.publications.gc.ca
Application of spinetoram provides effective control or suppression of a variety of insect pests of fruit, vegetable and cereal crops. It is also compatible ...
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Residual Time to 25% Bee Mortality (RT25) Data | US EPA
Feb 18, 2025 · The honey bee toxicity of residues on foliage study is a ... <. 3. Honey bee (Apis mellifera). Spinetoram. GF-1640 (24.7). 0.109 lb ...
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Combined effects of the pesticide spinetoram and ... - ResearchGate
Acute toxicity test of spinetoram resulted in negative effects on survival, with a 48-h LC50 value of 37.71 μg L⁻¹. Under the long-time exposure to ...
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[PDF] SAFETY DATA SHEET - Corteva Agriscience
Material is very highly toxic to aquatic organisms on an acute basis (LC50/EC50 <0.1 mg/L in the most sensitive species). LC50, Rainbow trout (Oncorhynchus ...
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40 CFR 180.635 -- Spinetoram; tolerances for residues. - eCFR
Tolerances are established for residues of the insecticide spinetoram, including its metabolites and degradates, in or on the commodities in the table below.
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Spinetoram; Pesticide Tolerances - Federal Register
Dec 21, 2021 · SUMMARY: This regulation establishes tolerances for residues of spinetoram in or on multiple commodities which are identified and discussed ...
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Spinetoram; Pesticide Tolerances - Federal Register
Sep 5, 2023 · This regulation establishes tolerances for residues of spinetoram in or on Spice group 26, and Stalk and stem vegetable subgroup 22A.Missing: global | Show results with:global
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Evaluation of confirmatory data following the Article 12 MRL review ...
Oct 15, 2025 · The applicant Corteva Agriscience International Sàrl submitted a request to the competent national authority in Croatia to evaluate the ...Missing: soil DT50 aerobic Koc leaching potential FAO JMPR
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Spinetoram J (Ref: XDE-175-J ) - AERU - University of Hertfordshire
CLP classification 2013. Health: H317, H361 Environment: H400, H410. WHO Classification. U (Unlikely to present an acute hazard). UN Number. -. Waste disposal ...Top · Environmental Fate · Ecotoxicology
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Spinetoram - Pesticide Detail | CODEXALIMENTARIUS FAO-WHO
For compliance with MRLs for plant and animal commodities: Spinetoram. For estimation of dietary intake for plant and animal commodities: Spinetoram and N ...Missing: international | Show results with:international<|separator|>