Workflows for the Structure Elucidation of Impurities in Synthetic Agrochemicals Using Mass Spectrometry

Zu, Chengli; Knueppel, Daniel; Gilbert, Jeff J.

doi:10.1021/bk-2019-1334.ch003

Cited by 2 publications

(2 citation statements)

References 41 publications

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“…To the best of our knowledge, only a few reports on the impurities in commercial agrochemical samples are available in the literature. The reports include impurity profiling of chlorpyrifos using GC–MS and haloxyfop‐P methyl ester using LC–MS, 16 bifenthrin using GC–MS, 2 pendimethalin using HPLC, 17 malathion, 18,19 d‐allethrin, 20 azoxystrobins, emamectin, metalaxyl, and benalaxyl fungicides. However, there are many agrochemicals in the current market without comprehensive information on their impurity profiles.…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of impurities in an insecticide, commercial chlorantraniliprole using liquid chromatography–tandem mass spectrometry

Kannoujia,

Chirra,

Rodda

et al. 2024

Rapid Comm Mass Spectrometry

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RationaleEnsuring the global safety and effectiveness of agrochemicals has become imperative. An in‐depth understanding of impurity profiles of products is crucial, especially for high‐demand agrochemicals, where impurities may be more toxic and persistent than original agrochemicals. This study focuses on the detection and identification of impurities in a commercial chlorantraniliprole (CAP), an anthranilic diamide class broad‐spectrum insecticide.MethodsCommercial CAP was collected from an agrochemical supplier in India and was analyzed using a high‐performance liquid chromatography‐photodiode array (HPLC‐PDA) (Agilent 1260; wavelength, 220 nm) with a Zorbax RP SB‐C18 (250 × 4.6 mm, 5 μm) column and liquid chromatography–mass spectrometry (LC–MS) (Agilent 6545 quadrupole time of flight (Q‐TOF)) techniques to identify the impurities. The impurities were isolated by preparative HPLC using a Zorbax‐DB C18 (250 × 9.4 mm, 5 μm) column. liquid chromatography– tandem mass spectrometry (LC–MS/MS) experiments (Q‐TOF) were performed on CAP and its impurities to obtain their structural data.ResultsHPLC‐PDA analysis of CAP showed four major impurities (IM‐1 to IM‐4) ranging from 0.76% to 4.1%. The positive ion electrospray ionization (ESI) mass spectra of CAP and its impurities showed dominant [M + H]+ ions in addition to [M + Na]+, [M + K]+, and [2M + Na]+ ions. High‐resolution mass spectrometry (HRMS) data provided the elemental composition of the compounds, and isotopic distribution patterns revealed the number of Cl and/or Br atoms present in them. The structures of impurities were proposed based on the LC–MS/MS) data and further confirmed by nuclear magnetic resonance (NMR) data on isolated impurities/synthesis.ConclusionThe quality and impurities of CAP, a popular insecticide, must be assessed and described for its efficacy and safety. In this study, four impurities of CAP were detected using HPLC and successfully characterized using LC‐HRMS, LC–MS/MS, and NMR data. The method is useful for verifying the purity of CAP as well as helping in the identification of its possible impurities.

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Section: Introductionmentioning

confidence: 99%

Identification and characterization of impurities in an insecticide, commercial chlorantraniliprole using liquid chromatography–tandem mass spectrometry

Kannoujia,

Chirra,

Rodda

et al. 2024

Rapid Comm Mass Spectrometry

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“…Furthermore, the use of high-resolution mass spectrometry (HRMS), employing quadrupole timeof-fight (Q-TOF) detector, is gaining more popularity in profling pharmaceutical impurity since it is capable of high-resolution mass detection (up to submilli-Dalton level) which would then provide high accuracy for structure and reaction mechanism prediction. Electrospray ionization in the positive mode is the preferred method in pharmaceutical impurity analysis, mainly due to its ability to detect thermally labile, nonvolatile, and polar compounds [20][21][22][23][24][25][26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Structure Identification and Risk Assurance of Unknown Impurities in Pramipexole Oral Drug Formulation

Tjandrawinata,

Cahyana,

Nugroho

et al. 2024

Advances in Pharmacological and Pharmaceutical Sciences

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Impurities compounds in any pharmaceutical product or drug substance are inevitable from a chemistry point of view. The quality and safety of a pharmaceutical product are also significantly affected by these impurities content; therefore, impurities need to be identified and characterized through the use of appropriate analytical methods. Pramipexole is a nonergot dopamine agonist used to treat various Parkinson’s disease symptoms. Two unknown impurities were detected from a pramipexole dihydrochloride solid dosage form. These impurities were identified and characterized using ultra-performance liquid chromatography coupled with high-resolution mass spectroscopy (UPLC-HRMS). These impurities were found to be enriched when mannitol existed in the formulation. The structure and mechanism involved in the existence of the impurities were proposed. Furthermore, observation of the binding affinity potential risk of these impurities to the pramipexole receptor has also been demonstrated through molecular docking and molecular dynamics simulation study. The binding energy result showed that pramipexole interaction with dopamine receptors D2 and D3 was higher than pramipexole mannose adduct and pramipexole ribose adduct.

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Workflows for the Structure Elucidation of Impurities in Synthetic Agrochemicals Using Mass Spectrometry

Cited by 2 publications

References 41 publications

Identification and characterization of impurities in an insecticide, commercial chlorantraniliprole using liquid chromatography–tandem mass spectrometry

Identification and characterization of impurities in an insecticide, commercial chlorantraniliprole using liquid chromatography–tandem mass spectrometry

Structure Identification and Risk Assurance of Unknown Impurities in Pramipexole Oral Drug Formulation

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