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The conclusions of the European Food Safety Authority (EFSA) following the peer review of the initial risk assessments carried out by the competent authorities of the rapporteur Member State Poland and co-rapporteur Member State Hungary for the pesticide active substance triclopyr (variant triclopyr-butotyl) and the assessment of applications for maximum residue levels (MRLs) are reported. The context of the peer review was that required by Commission Implementing Regulation (EU) No 844/2012, as amended by Commission Implementing Regulation (EU) No 2018/1659. The conclusions were reached on the basis of the evaluation of the representative uses of triclopyr (variant triclopyr-butotyl) as a herbicide on established pasture and non-recreational amenity grassland (field use). MRLs were assessed in rice. The reliable end points, appropriate for use in regulatory risk assessment and the proposed MRLs, are presented. Missing information identified as being required by the regulatory framework is listed. Concerns are reported where identified.

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The herbicide triclopyr (3,5,6-trichloro-2-pyridinyloxyacetic acid) is already considered an environmental problem due to damage caused by incorrect disposal, leaching, and aerial dispersion, which may pose risks to the environment and human health. Studies have evaluated metabolism, absorption, excretion, and active transport but there is no clear information about its mode of action (MoA) and its cytotoxic action potential remains unknown. In this context, mitochondria have been used to assess the toxicity of xenobiotics, for this reason, to identify the toxic mechanism of triclopyr, hepatic mitochondria from Wistar rats were exposed in vitro to different concentrations of triclopyr (0.5-500 µM). There was neither formation/accumulation of reactive oxygen and nitrogen species, nor lipid peroxidation or changes in the mitochondrial antioxidant system, in addition to proper functioning of oxidative phosphorylation and ATP production. Changes were found in NAD(P)H oxidation, membrane potential dissipation and mitochondrial calcium gradient. These results demonstrate that mitochondria suffer damage related to their bioenergetics and redox status but not to their structure when exposed to concentrations of triclopyr considered higher than those described as found in the environment so far.HighlightsTriclopyr has a low mitochondrial uncoupling potential.The damage caused to the bioenergetics and redox state of the mitochondria is related to concentrations considered higher than those found in the environment.Even at high concentrations, triclopyr was not able to change the structure of the organelle after exposure.Oxidative phosphorylation and ATP production were not impaired after exposure.NAD(P)H oxidation resulted in potential membrane dissipation and mitochondrial calcium gradient dissipation.Triclopyr does not have RONS-forming properties, as well as it does not peroxide membrane lipids, it preserves membrane sulfhydryl groups and maintains the normality of the GSH/GSSG ratio.

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Triclopyr, an auxin-like herbicide that is widely employed for managing weeds in food crops and pastures, has been identified in various environmental settings, particularly aquatic ecosystems. Limited understanding of the environmental fate of this herbicide, its potential repercussions for both the environment and human health, and its insufficient monitoring in diverse environmental compartments has caused it to be recognized as an emerging contaminant of concern. In this study, we have investigated how triclopyr affects zebrafish, considering a new alternative methodology. We focused on the endpoints of developmental toxicity, neurotoxicity, and behavior of zebrafish embryos and larvae. We determined that triclopyr has a 96 h median lethal concentration of 87.46 mg/L (341.01 µM). When we exposed zebrafish embryos to sublethal triclopyr concentrations (0.5, 1, 5, 10, and 50 µM) for up to 144 h, we found that 50 µM triclopyr delayed zebrafish egg hatchability. Yolk sac malabsorption was significant at 0.5, 1, 5, and 10 µM triclopyr. In zebrafish larvae, uninflated swim bladder was significant only at 50 µM triclopyr. Furthermore, zebrafish larvae had altered swimming activity after exposure to 10 µM triclopyr for 144 h. In summary, these comprehensive results indicate that even low triclopyr concentrations can elicit adverse effects during early zebrafish development.

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In accordance with Article 6 of Regulation (EC) No 396/2005, the applicant Corteva Agriscience International Sàrl submitted a request to the competent national authority in the Netherlands to modify the existing maximum residue levels (MRLs) for the active substance triclopyr in animal commodities. The data submitted in support the request were found to be sufficient to derive MRL proposals for swine and ruminant edible commodities and for ruminant milks considering residue levels expected for the intended uses on grassland. Adequate analytical methods for enforcement are available to control the residues of triclopyr on the commodities under consideration at the validated limit of analytical quantification (LOQ) of 0.01 mg/kg. Based on the risk assessment results, EFSA concluded that the short-term and long-term intake of residues resulting from the uses of triclopyr according to the reported agricultural practices and the derived MRLs in products of animal origin is unlikely to present a risk to consumer health. The consumer risk assessment is indicative pending the submission of the confirmatory data requested under the MRL review.

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In accordance with Article 6 of Regulation (EC) No 396/2005, the applicant Agriphar SA submitted a request to the competent national authority in Ireland to modify the existing maximum residue levels (MRLs) for the active substance triclopyr in oranges, lemons and mandarins. The data submitted in support of the request were found to be sufficient to derive an MRL proposal for these commodities. Adequate analytical methods for enforcement are available to control the residues of triclopyr in the plant matrices under consideration at the validated LOQ of 0.01 mg/kg. Based on the risk assessment results, EFSA concluded that the short-term and long-term intake of residues resulting from the use of triclopyr according to the reported agricultural practice is unlikely to present a risk to consumer health.

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Polyaniline supported titanium dioxide nanoparticles (PTs) were fabricated using chemical oxidative aniline polymerization in the presence of titanium dioxide with ammonium peroxydisulfate as an oxidant. The synthesized PTs were thoroughly characterized for their morphological and functional features. PTs were employed for the photodegradation of acidic herbicides; 2,4-dichlorophenoxyacetic acid (2,4-D) and triclopyr acid (TCP). PT's surface modifications were imparted and their herbicide removal efficiencies were compared. The best operating conditions for adsorption/photocatalysis were 0.5 g/L photocatalyst, 10 mg/L concentration of individual herbicides resulted in 90.72% removal of TCP at pH 4 and 99.91% removal of 2,4-D at pH 5. Adsorption kinetics of herbicides, onto PT-1 showed the equilibrium attainment within 30 min and experimental data obeyed pseudo-second order model for TCP and 2,4-D removal which was governed by chemisorption. Analysis of TCP and 2,4-D adsorption indicated that the removal followed Sips model for TCP removal while Redlich-Peterson model explained the removal of 2,4-D by PT-1. Rate constants indicated that the amount of TiO2 in the PTs played an important role in removing the herbicides and PT-1 material excellent remarkable activity for three cycles of photodegradation. Thus, this work reports the polymerization of aniline onto TiO2 and their utility as photocatalyst for the expulsion of 2,4-D and TCP from water.

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Developmental toxicity studies have been conducted in the rabbit on triclopyr acid and its active-ingredient variants, triclopyr triethylamine salt (T-TEA) and triclopyr butoxyethyl ester (T-BEE), which are dissociated or hydrolysed in vivo to triclopyr acid. In this paper, the available developmental toxicity studies on triclopyr acid, T-TEA and T-BEE are summarised and evaluated. For triclopyr acid and T-TEA, there was no evidence of impaired reproductive performance, fetotoxicity, or teratogenicity, even at maternally toxic doses. The no-observed-adverse-effect levels (NOAELs) for developmental toxicity were 75 mg/kg bw per day for triclopyr acid and 100 mg/kg bw per day for T-TEA, equivalent to 72 mg/kg bw per day expressed as triclopyr acid. A study on T-BEE showed increased post-implantation loss and slight increases in skeletal anomalies and variants at the highest dose tested of 100 mg/kg bw per day, a maternally toxic dose. In a follow-up study on T-BEE, focusing on post-implantation loss, no general increase in post-implantation loss was observed, but one animal at 100 mg/kg bw per day with maternal toxicity had complete resorption of implants. The NOAEL for post-implantation loss was 60 mg/kg bw per day, equivalent to 44 mg/kg bw per day expressed as triclopyr acid. It cannot be excluded that T-BEE may be associated with increased post-implantation loss, but it was only seen in association with maternal toxicity. It is concluded that triclopyr acid and its variants are not specifically toxic to the rabbit embryo and fetus, since post-implantation loss only occurred at doses causing maternal toxicity.

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Reproductive and developmental toxicity studies have been conducted in rat and rabbit on triclopyr acid and its active-ingredient variants, triclopyr butoxyethyl ester (T-BEE) and triclopyr triethylamine salt (T-TEA). In this paper the results of a rat two-generation study on triclopyr acid are presented, together with a review of all the reproductive and developmental toxicity data available from the rat studies. In the rat two-generation study, triclopyr acid was administered in the diet, giving doses of 0, 5, 25 or 250 mg/kg bw per day. Parental toxicity, especially maternal toxicity, occurred at 250 mg/kg bw per day with reduced body weight and feed intake, organ weight changes, and kidney toxicity. Slight kidney toxicity was also evident at 25 mg/kg bw per day. Developmental toxicity, in the form of reduced postnatal survival in the F1 and F2 generations and reductions in pre-weaning offspring body weight in both generations, was seen only at a dose causing significant parental toxicity. There were no effects on any other reproductive or developmental parameters at any dose. It is concluded that the developmental toxicity, seen only at the highest dose, was most likely attributable to maternal toxicity. The no-observed-adverse-effect levels were 5 mg/kg bw per day for parental toxicity and 25 mg/kg bw per day for developmental toxicity. From the multigeneration and developmental toxicity studies on triclopyr and its variants, it can also be concluded that triclopyr is not specifically toxic to reproduction and is not selectively toxic to the embryo, fetus or neonate in the rat.

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Mechanism of direct UV photolysis of pyridine herbicide triclopyr (TRI) was revealed by the combination of nanosecond laser flash photolysis, steady-state photolysis coupled with high resolution LC-MS and DFT quantum-chemical calculations. Both the detection of short-lived intermediates and the detailed identification of final products were done for the first time. The quantum yield of TRI photodegradation is about 4% at both UVC (254 nm) and UVB (308 nm) excitation. The primary stage is the heterolytic cleavage of C-Cl bond in dissociative triplet state of TRI with the formation of phenyl cation followed by a fast nucleophilic attack by a solvent molecule. The minor channel is the photohydrolysis leading to the formation of 3,5,6-trichloropyridin-2-ol. Primary photoproducts undergo secondary photolysis by the mechanism similar to initial TRI with the formation of products of acetic group elimination, sequential substitution of chlorine atoms to hydroxyl groups and, finally, oxidation and opening of the pyridine ring. Obtained results can be important for understanding the fate of pyridine herbicides in the processes of UVC disinfection and in natural waters under action of the sunlight.

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Fluroxypyr-meptyl and triclopyr are synthetic auxin-like herbicides that are used to control woody and broadleaf weeds. Herein, we report a case of fatal intoxication involving fluroxypyr-meptyl and triclopyr. A 61-year-old man was found dead at his farm with several suicide notes, and a white plastic bottle and a plastic cup with traces of white emulsion were found next to him. The plastic bottle was labeled as an herbicide formulation containing fluroxypyr-meptyl and triclopyr. Forensic toxicological screening of the stomach contents revealed the presence of fluroxypyr-meptyl, fluroxypyr and triclopyr. However, no fluroxypyr-meptyl was detected in blood owing to its rapid hydrolysis to fluroxypyr. In this study, fluroxypyr and triclopyr in blood were extracted using solid-phase extraction, and analyzed by liquid chromatography-tandem mass spectrometry. The analytical method was validated in terms of linearity, precision, accuracy, recovery and matrix effect, and the acceptable criteria were satisfied. Toxicological analysis showed that fluroxypyr and triclopyr concentrations were 19.7 µg/mL and 137.4 µg/mL in peripheral blood and 16.5 µg/mL and 147.8 µg/mL in heart blood, respectively. Based on these toxicological results and autopsy findings, the cause of death was determined to be acute fatal intoxication by ingestion of the pesticide containing fluroxypyr-meptyl and triclopyr. This is the first report of the determination of fluroxypyr and triclopyr in a fatal intoxication case.

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INTRODUCTION: Triclopyr is a synthetic auxin-like herbicide. It is considered to have low toxicity and there are few reports of poisoning. We report two cases of life-threatening toxicity following ingestions of 250 mL of 50 g/L triclopyr co-formulated with diethylene glycol monoethyl ether (DEGEE). CASE REPORTS: A 79-year-old male with a background of hypertension and atrial fibrillation presented two hours after ingestion with sedation, a severe high anion gap metabolic acidosis, raised osmolar gap and an aspiration pneumonitis. He was ventilated and dialysed for 10 h with resolution of the acidaemia. He was discharged home on day 33. A 66-year-old male with a past history of alcoholism and hypertension presented following a collapse. He had sedation, a severe high anion gap metabolic acidosis with a raised osmolar gap, acute kidney injury and vasodilatory shock. He was ventilated and received dialysis for 43 h. He had poor neurological recovery and died on day 10. DISCUSSION: Ingestion of triclopyr formulations can produce life-threatening toxicity. In large poisonings of triclopyr co-formulated with DEGEE, a high anion gap metabolic acidosis appears to be due to the glycol ether solvent rather than triclopyr itself. Management should focus on good supportive care including dialysis for significant metabolic acidosis.

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One of the main challenges of electrochemical Fenton-based processes is the treatment of organic pollutants at near-neutral pH. As a potential approach to this problem, this work addresses the use of a low content of soluble chelated metal catalyst, formed between Fe(III) and ethylenediamine-N,N'-disuccinic (EDDS) acid (1:1), to degrade the herbicide triclopyr in 0.050 M Na2SO4 solutions at pH 7.0 by photoelectro-Fenton with UVA light or sunlight (PEF and SPEF, respectively). Comparison with electro-Fenton treatments revealed the crucial role of the photo-Fenton-like reaction, since this promoted the production of soluble Fe(II) that enhanced the pesticide removal. Hydroxyl radicals formed at the anode surface and in the bulk were the main oxidants. A boron-doped diamond (BDD) anode yielded a greater mineralization than an IrO2-based one, at the expense of reduced cost-effectiveness. The effect of catalyst concentration and current density on the performance of PEF with BDD was examined. The PEF trials in 0.25 mM Na2SO4 + 0.35 mM NaCl medium showed a large influence of generated active chlorine as oxidant, being IrO2 more suitable than RuO2 and BDD. In SPEF with BDD, the higher light intensity from solar photons accelerated the removal of the catalyst and triclopyr, with small effect on mineralization. A plausible route for the herbicide degradation by Fe(III)-EDDS-catalyzed PEF and SPEF is finally proposed based on detected byproducts: three heteroaromatic and four linear N-aliphatic compounds, formamide, and tartronic and oxamic acids.

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Herbicide use on boreal transmission line rights-of-way has been relatively limited compared to more temperate regions and therefore challenges exist in estimating and communicating the associated risks. Herbicides directly enter the ecosystem through deposition on vegetation and soils and can be a vector of contamination to browsing herbivores. Triclopyr drift and foliage concentrations were quantified following basal bark (Garlon RTU) and low-volume foliar (Garlon XRT) field treatments to aspen (Populus tremuloides) saplings and willow (Salix bebbiana) shrubs, respectively. Greater drift concentrations localized at the stem base were observed following basal bark treatments. Conversely, concentrations in foliage following the low-volume foliar treatment (DT50 = 5.7 days and DT90 = 34.6 days) were much higher than following basal bark treatment, which also required two days to translocate into the leaves. However, dissipation was rapid from both application methods and triclopyr in foliage was less than 20 µg g-1 a year following application. A risk assessment revealed an acceptable level of risk for acute toxicity to wildlife browsing on contaminated leaves from the residues detected in this study; however, an unacceptable level of risk for chronic toxicity to long-term browsing moose. Site-specific data regarding browsing behaviour on herbicide treated rights-of-ways and species-specific reference values are needed to improve confidence in the tier-two risk assessment. Basal bark application is ideal when stem density is lower and toxic effects for herbivores is of concern and low-volume foliar applications are best suited in areas with higher stem density when off-target herbicide deposition is less acceptable.

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Herbicides help increase agricultural yields significantly, but they may negatively impact the life of non-target organisms. Modifying the life cycle of primary producers can affect other organisms in the food chain, and consequently in the whole ecosystem. We investigated the effect of common herbicides Roundup® Classic Pro (active substance glyphosate) and Garlon New (triclopyr and fluroxypyr) on aquatic organisms duckweed Lemna minor and green algae Desmodesmus subspicatus, and on the enzymatic activity of soil. We also compared the effects of Roundup® Classic Pro to that of a metabolite of its active substance, aminomethylphosphonic acid (AMPA). The results of an algal growth test showed that AMPA has a 1.5× weaker inhibitory effect on the growth of D. subspicatus than the Roundup formula, and the strongest growth inhibition was caused by Garlon New (IC50Roundup = 267.3 µg/L, IC50Garlon = 21.0 µg/L, IC50AMPA = 117.8 mg/L). The results of the duckweed growth inhibition test revealed that Roundup and Garlon New caused 100% growth inhibition of L. minor even at significantly lower concentrations than the ready-to-use concentration. The total chlorophyll content in the fronds was lowest when Garlon New was used. The highest dehydrogenase activity was observed in soil treated with Garlon New, and the lowest in soil treated with Roundup® Classic Pro. The results of this study showed that all three tested substances were ecotoxic to the tested organisms.

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A review of pharmacokinetic and metabolism studies show that triclopyr is well absorbed from the oral route in numerous species (≥80%), primarily as parent compound. Absorption is quite rapid in rats, dogs and human volunteers. Plasma or blood clearance is also rapid (t1/2 3-9 h), except for dog (12-96 h). Systemic exposure is not dose-proportional: in the rat above 20 mg/kg (dietary) or between 3 and 60 mg/kg (gavage), or in dogs above 5 mg/kg, with systemic exposure in human more comparable to rat than dog. Triclopyr is highly bound to protein in rat, dog and human plasma (≥97% at or below 7 µg/mL), indicating that species differences in systemic exposure are not due to differences in the free fraction of this test material in plasma. An in vitro flux study in renal proximal tubule cells showed that net renal transport of triclopyr is in the direction of secretion in rat and human donors, while reabsorption predominated in the dog, possibly via organic anion transporters such as OAT1/3. These results fit well into the framework of utilizing metabolism and toxicokinetics across species and exposure levels to allow for toxicity testing in the most relevant species as well as at proper dose levels.

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In accordance with Article 6 of Regulation (EC) No 396/2005, the applicant Arysta LifeScience Benelux submitted a request to the competent national authority in Greece to modify the existing maximum residue levels (MRLs) for the active substance triclopyr in kiwi fruits. The data submitted in support of the request were found to be sufficient to derive an MRL proposal for kiwi fruits. Adequate analytical methods for enforcement are available to control the residues of triclopyr in the plant matrix under consideration (i.e. high acid content commodity) at the validated limit of quantification (LOQ) of 0.01 mg/kg. Based on the risk assessment results, EFSA concluded that the short-term and long-term intake of residues resulting from the use of triclopyr according to the reported agricultural practice is unlikely to present a risk to consumer health.

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The herbicide Triclopyr (TCP) is widely applied to minimize the growth of woody plants. Monitoring of TCP is of major environmental concern due to its adverse impact on aquatic organisms, soils and animals. Electrochemical behavior of TCP was investigated at C70 decorated PANI modified glassy carbon sensor (PANI/C70/GC). The experimental parameters, such as concentration, pH, amplitude, frequency, deposition potential were optimized. The modified sensor exhibited an excellent catalytic response towards the reduction of TCP with a well-defined reduction peak at 1.72 V. The developed sensor was characterized by scanning electron microscopy (SEM), fourier transform infrared spectroscopy (FTIR), X-Ray diffraction (XRD) and electrochemical impedance spectroscopy (EIS). The electrochemical measurements were carried out using square wave (SWV) and cyclic voltammetry (CV). The modified sensor exhibited linear calibration curve for TCP over a concentration range of 10 ngmL-1-100 ngmL-1 with detection limit of 1.9 ngmL-1. The developed sensor could detect TCP efficiently without any interference from the common metabolites. The voltammetric procedure was applied successfully to real sample analysis with high sensitivity and good selectivity.

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In this study, a new method for the simultaneous quantitative determination of triclopyr and aminopyralid in forage grass, hay, and soil was developed and validated using gas chromatography coupled with electron capture detector (GC-ECD). In this method, a simple and maneuverable esterification reaction was applied to convert the two acidic herbicides into their ester form with methanol. The target compounds were extracted with 1% hydrochloric acid-acetonitrile, esterified, purified by florisil solid-phase extraction cartridge, and detected in a single run by the GC-ECD. The average recoveries using this method, at different fortified levels, ranged from 80% to 104% with intra-day and inter-day RSDs in the range of 1.2-10.8% and 3.3-10.3% for both the herbicides, respectively. The LODs were below 0.02 mg/kg while the LOQs were below 0.05 mg/kg, both of which were much lower than the maximum residue limits (MRLs) of 25-700 mg/kg in pastures, as established by the USA (the code of federal regulations). The open field dissipation and residual analysis in pastures and soil were conducted with the commercial formulation at two locations. With time, both triclopyr and aminopyralid dissipated via first-order kinetics. In forage grass, both compounds degraded rapidly over the first 14- or 21-d period and at a slow rate over the remainder of experimental days. In soil, they degraded at a relatively slow rate, and dissipated steadily to below or close to the LOQ by 60-d post application. The half-lives of triclopyr were 1.4-1.8 d and 6.2-9.0 d and aminopyralid were 1.7-2.1 d and 8.2-10.6 d in terms of forage grass and soil, respectively. The terminal residue results indicated that on 7 d after the treatment, the residues of aminopyralid and triclopyr in forage grass and hay were lower than the MRLs set by the USA. This work can provide guidance on the reasonable use of these herbicides and also provide an analytical method for the determination of triclopyr and aminopyralid in pasture and soil.

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This study focused on the residue detection of the herbicides triclopyr and glufosinate ammonium in the runoff losses from the Tasik Chini oil palm plantation area and the Tasik Chini Lake under natural rainfall conditions in the Malaysian tropical environment. Triclopyr and glufosinate ammonium are post-emergence herbicides. Both herbicides were foliar-sprayed on 0.5 ha of oil palm plantation plots, which were individualized by an uneven slope of 10-15%. Samples were collected at 1, 3, 7, 15, 30, 45, 60, 90, and 120 days after treatment. The concentrations of both herbicides quickly diminished from those in the analyzed sample by the time of collection. The highest residue levels found in the field surface leachate were 0.031 (single dosage, triclopyr), 0.041 (single dosage, glufosinate ammonium), 0.017 (double dosage, triclopyr), and 0.037 µg/kg (double dosage, glufosinate ammonium). The chromatographic peaks were observed at "0" day treatment (2 h after herbicide application). From the applied active ingredients, the triclopyr and glufosinate losses were 0.025 and 0.055%, respectively. The experimental results showed that both herbicides are less potent than other herbicides in polluting water systems because of their short persistence and strong adsorption onto soil clay particles.

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Invasive plants impact amphibians by altering habitat, altering species interactions, and releasing potentially toxic secondary chemicals. Despite being costly and having the potential to affect nontarget wildlife, chemical management is commonly used to control invasive plants. Prior research has indicated that individual effects of invasive plants or herbicides can be harmful to aquatic organisms; however, information is lacking on the combined effect of these factors on amphibians. A laboratory experiment was performed to assess the impact of leachates of the invasive plants Eurasian watermilfoil (Myriophyllum spicatum) and European buckthorn (Rhamnus cathartica), the herbicide Renovate® 3 (triclopyr [3, 5, 6-trichloro-2-pyridinyloxyacetic acid]), and the combined effects of each plant leachate and the herbicide on the growth, morphology, and survival of northern leopard frog (Lithobates pipiens) tadpoles. No effects of treatment on survival were observed. Tadpole exposure to M. spicatum reduced body mass by 17%, exposure to R. cathartica increased body mass by 36%, and exposure to R. cathartica + low herbicide increased body mass by 38% (although only early in the experiment). Exposure to Renovate 3 induced a 16% and 29% decrease in tadpole size in lower (0.22 mg triclopyr active ingredient [a.i.]/L) and higher (0.92 mg triclopyr a.i./L) concentration treatments, respectively. Results from the present study highlight the importance of considering both individual and combined effects of invasive plants and herbicides because they may have different outcomes for tadpole growth and development. Environ Toxicol Chem 2017;36:2958-2964. © 2017 SETAC.

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