Imazapyr

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Imazapyr
Category Agricultural
Catalog number BBF-05902
CAS 81334-34-1
Molecular Weight 261.28
Molecular Formula C13H15N3O3

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Description

Imazapyr is a broad-spectrum herbicide used in weed control.

Specification

Synonyms Imazapyr acid; Charper; Chopper
IUPAC Name 2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid
Canonical SMILES CC(C)C1(C(=O)NC(=N1)C2=C(C=CC=N2)C(=O)O)C
InChI InChI=1S/C13H15N3O3/c1-7(2)13(3)12(19)15-10(16-13)9-8(11(17)18)5-4-6-14-9/h4-7H,1-3H3,(H,17,18)(H,15,16,19)
InChI Key CLQMBPJKHLGMQK-UHFFFAOYSA-N

Properties

Application Pesticide

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).

Reference Reading

1. Exposure impacts of Imazapyr formulation on larval development and thyroid histology of Xenopus laevis
Oluwaseun Olusegun Babalola, Johannes Hannes van Wyk Environ Sci Pollut Res Int. 2021 Oct;28(37):50967-50974. doi: 10.1007/s11356-021-14227-4. Epub 2021 May 11.
There are increased concerns about the thyroidal effects of many anthropogenic substances in the environment. These substances include agricultural pesticides and industrial and pharmaceutical chemicals among others. Their potential thyroidal effects are of serious health and ecological concerns, as thyroid hormones mediate numerous physiological processes, including growth regulation, general metabolism and metamorphosis in metamorphic animals. This study assessed thyroidal activities of Arsenal formulation (Imazapyr) at environmentally relevant concentrations of 0.5, 2.0 and 3.5 mg/L following a Xenopus metamorphosis assay (XEMA). The result shows that the Arsenal formulation significantly delayed the tadpole development, reduced the hind-limb length (HLL) and increased the whole-body mass (WBM) at a concentration of 3.5 mg/L relative to the control exposure. In histopathology, the formulation increased the epithelium height, at all exposure concentrations, but reduced the colloidal area at 0.5 and 2 mg/L, respectively, and the gland area at 2 mg/L relative to the control. Consequently, the Arsenal formulation is thyroid-active at environmentally relevant concentrations and poses a threat to both human and wildlife, especially metamorphic organisms. With this exposure impact, more studies are imperative to further characterise other endocrine-disrupting potential of this formulation, while future applications should be reduced or restricted to less risk environment, if it cannot be stopped from sensitive aquatic systems.
2. Cumulative potential and half-life of [imazapic + imazapyr] in lowland soils of Rio Grande Do Sul grown with clearfield® rice
Thais Stradioto Melo, Caroline Hernke Thiel, Laryssa Barbosa Xavier da Silva, Sidnei Deuner, André Andres, Gabriele Espinel Ávila, Stefânia Nunes Pires, Germani Concenço J Environ Sci Health B. 2022;57(6):450-457. doi: 10.1080/03601234.2022.2063613. Epub 2022 Apr 12.
The objectives of this study were to estimate the residual and half-life of [imazapic + imazapyr] and to infer on the impact of these residuals over time. The first experiment comprised the application of [imazapic + imazapyr] to Clearfield® rice. On the following summer cropping season (365 days later), undeformed soil samples 0-5 cm depth were collected and seeds of six species or varieties were sown as bioindicators of residuals (experiment 2), being assessed plant height and dry mass 20 days after emergence start. The third experiment comprised the cultivation of the same species submitted to ten increasing herbicide doses (0-280 g ha-1) to establish standard response curves, also assessing plant height and dry mass 20 days after emergence start. About 2.1-5.8% of the applied imazapic remains in soil after one year, for the label doses. Imazapyr was considered to be at negligible doses as its half-life is short, and less than 0.0000001% of the applied dose is expected to be in soil 365 days later. The expected imazapic half-life in lowland areas of Southern Brazil is longer than for dryland, being estimated as between 63 and 77 days (95% confidence interval), contrasting to the 60 days half-life previously estimated for dryland soils.
3. Residues and Dissipation of the Herbicide Imazapyr after Operational Use in Irrigation Water
Tony M Dugdale, Kym L Butler, Mark J Finlay, Zhiqian Liu, David B Rees, Daniel Clements Int J Environ Res Public Health. 2020 Apr 2;17(7):2421. doi: 10.3390/ijerph17072421.
Imazapyr is a herbicide that can be used in irrigation canals to control a range of aquatic weed species, however, its residual nature, combined with its phytotoxicity to crops at low concentrations, means that the water in canals must be carefully managed following imazapyr application. Residues of the herbicide imazapyr (isopropylamine salt) in irrigation water were analysed and modelled after application to irrigation canals in south-eastern Australia. A treatment program to control delta arrowhead (sagittaria; Sagittaria platyphylla (Engelm.) J.G. Sm.) in over 400 km of irrigation canals was enacted by applying imazapyr to dewatered canals during winter. Following imazapyr application, canals were left dewatered for a period (up to eight weeks) and then refilled. After refilling, canals were ponded for a period (up to 28 days) to allow degradation of imazapyr in the water via photolysis. Upon refilling canals, ~650 water samples containing imazapyr were collected across the treatment area and data modelled to measure the extent of water contamination and to guide efforts to reduce the subsequent irrigation hazard to crops. Modelled data demonstrates that imazapyr behaviour in irrigation water following canal refilling was predictable when 1) amount of imazapyr applied, 2) the dewatered period following herbicide application, 3) the water ponding period, and 4) solar exposure during water ponding were taken into account. Minimising the amount applied (g imazapyr per km of canal) and maximising the time between spraying and refilling (dewatered period) reduced the initial concentration in the water following canal refilling. The amount of imazapyr in the canal water following refilling was reduced by half for every 16 days (confidence interval = 10-38 days) that the canal remained dewatered after imazapyr application. Imazapyr dissipation during the ponding period following canal refilling occurred at a rate that depended on solar exposure. Dissipation did not occur when solar exposure was 10 MJ m-2, imazapyr concentration in the water reduced by half for every 4.4 days of ponding period (confidence interval = 2.9-9.5 days). Our two models, combined with local climate data on solar exposure, can be used by canal managers to determine the optimal time to refill canals so that imazapyr dissipation is maximised, and thus risk of damaging irrigated crops is minimised.

Spectrum

LC-MS/MS Spectrum - 20V, Positive

Predicted LC-MS/MS Spectrum - 10V, Negative

Experimental Conditions

Ionization Mode: Negative
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

1H NMR Spectrum

Experimental Conditions

Solvent: CDCl3
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS

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