Persistence of the sulfonylurea herbicide iodosulfuron-methyl in the soil of winter wheat crops

Rouchaud, Jean; Moulard, Claude; Eelen, Hilde; Bulcke, Robert

doi:10.1080/02772240410001665409

Cited by 9 publications

(3 citation statements)

References 20 publications

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“…Overall, trends indicate a steady increase in demand for this type of herbicides worldwide [ 9 ]. Currently, one of the most effective sulfonylurea-based herbicides globally is sodium salt of iodosulfuron-methyl presented in the Figure 1 [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

et al. 2021

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Efficient use of herbicides for plant protection requires the application of auxiliary substances such as surfactants, stabilizers, wetting or anti-foaming agents, and absorption enhancers, which can be more problematic for environment than the herbicides themselves. We hypothesized that the combination of sulfonylurea (iodosulfuron-methyl) anion with inexpensive, commercially available quaternary tetraalkylammonium cations could lead to biologically active ionic liquids (ILs) that could become a convenient and environment-friendly alternative to adjuvants. A simple one-step synthesis allowed for synthesizing iodosulfuron-methyl based ILs with high yields ranging from 88 to 96% as confirmed by UV, FTIR, and NMR. The obtained ILs were found to possess several favorable properties compared to the currently used sodium salt iodosulfuron-methyl, such as adjustable hydrophobicity (octanol-water partition coefficient) and enhanced stability in aqueous solutions, which was supported by molecular calculations showing cation–anion interaction energies. In addition, soil mobility and volatility of ILs were more beneficial compared to the parental herbicide. Herbicidal activity tests toward oil-seed rape and cornflower revealed that ILs comprising at least one alkyl chain in the decyl to octadecyl range had similar or better efficacy compared to the commercial preparation without addition of any adjuvant. Furthermore, results of antimicrobial activity indicated that they were practically harmless or slightly toxic toward model soil microorganisms such as Pseudomonas putida and Bacillus cereus.

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Section: Introductionmentioning

confidence: 99%

Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

et al. 2021

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“…Villaverde et al, reported that the DT 50 of flupyrsulfuron-methyl was 5.6 days in soil with pH 7.9, and 9.4 days at pH 8.4 [ 22 ]. Rouchaud et al, found that iodosulfuron-methyl degraded rapidly at pH 8.0, with a DT 50 of 30-40 days [ 23 ]. Tang et al, reported that the DT 50 of iodosulfuron-methyl was 6–23.9 days at pH 5.14–9.42 [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

Alkaline Soil Degradation and Crop Safety of 5-Substituted Chlorsulfuron Derivatives

Hua

et al. 2022

Molecules

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Sulfonylurea herbicides can lead to serious weed resistance due to their long degradation times and large-scale applications. This is especially true for chlorsulfuron, a widely used acetolactate synthase inhibitor used around the world. Its persistence in soil often affects the growth of crop seedlings in the following crop rotation, and leads to serious environmental pollution all over the world. Our research goal is to obtain chlorsulfuron-derived herbicides with high herbicidal activities, fast degradation times, as well as good crop safety. On account of the slow natural degradation of chlorsulfuron in alkaline soil, based on the previously reported results in acidic soil, the degradation behaviours of 5-substituted chlorsulfuron analogues (L101–L107) were investigated in a soil with pH 8.39. The experimental data indicated that 5-substituted chlorsulfuron compounds could accelerate degradation rates in alkaline soil, and thus, highlighted the potential for rational controllable degradation in soil. The degradation rates of these chlorsulfuron derivatives were accelerated by 1.84–77.22-fold, compared to chlorsulfuron, and exhibited excellent crop safety in wheat and corn (through pre-emergence treatment). In combination with bioassay activities, acidic and alkaline soil degradation, and crop safety, it was concluded that compounds L104 and L107, with ethyl or methyl groups, are potential green sulfonylurea herbicides for pre-emergence treatment on wheat and corn. This paper provides a reference for the further design of new sulfonylurea herbicides with high herbicidal activity, fast, controllable degradation rates, and high crop safety.

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“…Various analytical methods have been used to detect metsulfuron-methyl residue in the environment, such as high performance liquid chromatography (HPLC) [ 1 , 6 ], gas chromatography (GC) [ 7 ], mass spectrometry (MS) [ 8 ], HPLC-MS [ 9 ], GC-MS [ 10 ], immunoassays [ 11 ], fluorimetry, and capillary electrophoresis [ 12 ]. These methods are highly sensitive and selective, but involve costly instruments and complex, time-consuming operations performed in laboratories.…”

Section: Introductionmentioning

confidence: 99%

Visual and Colorimetric Sensing of Metsulfuron-Methyl by Exploiting Hydrogen Bond-Induced Anti-Aggregation of Gold Nanoparticles in the Presence of Melamine

Liu

Zhang

Huang

et al. 2018

Sensors

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Various highly sensitive and selective analytical methods have been used to monitor metsulfuron-methyl residue in the environment. However, these methods involve costly instruments and complex, time-consuming operations performed in laboratories. Here, a rapid, convenient, and sensitive colorimetric sensor based on anti-aggregation of gold nanoparticles (AuNPs) is demonstrated for the rapid detection of metsulfuron-methyl in agricultural irrigation water. The AuNPs could be induced to aggregate in the presence of melamine and exhibited a distinct color change from wine-red to blue. The aggregation was suppressed by a strong hydrogen-bonding interaction between metsulfuron-methyl and melamine. The differences of the absorbance at 523 nm (ΔA523) and the color change was linearly related to metsulfuron-methyl concentration over the range 0.1–100 mg/L, as observed visually and by UV-vis (Ultraviolet-visible) spectrometry. The detection limit of the sensor was as low as 0.05 mg/L (signal/noise = 3), and was used to determine metsulfuron-methyl in spiked water and in agricultural irrigation water samples. Recoveries were in the range of 71.2–100.4%, suggesting that the colorimetric sensor was suitable for the determination of metsulfuron-methyl in agricultural water samples.

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Persistence of the sulfonylurea herbicide iodosulfuron-methyl in the soil of winter wheat crops

Cited by 9 publications

References 20 publications

Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

Alkaline Soil Degradation and Crop Safety of 5-Substituted Chlorsulfuron Derivatives

Visual and Colorimetric Sensing of Metsulfuron-Methyl by Exploiting Hydrogen Bond-Induced Anti-Aggregation of Gold Nanoparticles in the Presence of Melamine

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