Quantitative structure–transformation relationships of sulfonylurea herbicides

Berger, B.; Müller, M.; Eing, Andreas

doi:10.1002/ps.519

Cited by 14 publications

(13 citation statements)

References 30 publications

(57 reference statements)

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“…As neither bacterial numbers nor community heterogeneity of the bacterial community was severely affected by pesticide application, it may be that microbial degradation and utilization of these products caused community differences. Degradation of (77) and in situ (26), but with the exception of the sulfonureas most of the research has been carried out on photodegradation, physical degradation, and chemical degradation of these chemicals (5,41,45). Seasonal variation again resulted in the greatest differentiation between the active fungal communities, with clustering patterns similar to those observed for bacterial communities (Fig.…”

Section: Discussionmentioning

confidence: 69%

Responses of Active Bacterial and Fungal Communities in Soils under Winter Wheat to Different Fertilizer and Pesticide Regimens

Girvan

Bullimore

Ball

et al. 2004

Appl Environ Microbiol

156

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The composition of the active microbial (bacterial and fungal) soil community in an arable wheat field subjected to different management practices was examined at five times during a 1-year period. Field sections were fertilized either at good agricultural practice (GAP) levels or at reduced levels (0.5؋ GAP) and were inoculated with vesicular arbuscular mycorrhizae (VAM) at the same time. Field subsections were treated either with or without pesticides. Changes in the active microbial communities were investigated by denaturing gradient gel electrophoresis analysis of reverse transcription-PCR-amplified 16S and 18S rRNA. Microbial community structure was primarily determined by season, and the seasonal trends were similar for the fungal and bacterial components. Between-sample microbial heterogeneity decreased under a mature crop in the summer but increased following harvesting and plowing. Although similar overall trends were seen for the two microbial components, sample variability was greater for the fungal community than for the bacterial community. The greatest management effects were due to GAP fertilization, which caused increases in the bacterial numbers in the total and culturable communities. Microbial biomass similarly increased. GAP fertilization also caused large shifts in both the active bacterial community structure and the active fungal community structure and additionally resulted in a decrease in the heterogeneity of the active bacterial community. Pesticide addition did not significantly affect bacterial numbers or heterogeneity, but it led to major shifts in the active soil bacterial community structure. PCR primers specific for Glomales 25S rRNA genes were used to monitor the VAM population following inoculation. Glomales were detected initially only in VAM-inoculated field sections but were subsequently detected in noninoculated field sections as the season progressed. After plowing, the level of Glomales was reduced in noninoculated field sections but remained high in VAMinoculated field sections. Inoculation of VAM correlated with elevated soil phosphate and carbon levels.

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Section: Discussionmentioning

confidence: 69%

Responses of Active Bacterial and Fungal Communities in Soils under Winter Wheat to Different Fertilizer and Pesticide Regimens

Girvan

Bullimore

Ball

et al. 2004

Appl Environ Microbiol

156

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“…The sulfonylureas represent a large and very successful class of selective herbicides [113] originally discovered by DuPont. They are the most active commercial herbicides to be developed, with a typical use rate of only grams per hectare.…”

Section: Sulfonylureasmentioning

confidence: 99%

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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The task of inventing and developing active ingredients with useful biological activities requires a search for novel chemical substructures. This process may trigger the discovery of whole classes of chemicals of potential commercial interest. Similar biological effects can often be achieved by completely different compounds. However, compounds within a given structural family may exhibit quite different biological activities depending on their interactions with different intracellular proteins like enzymes or receptors. By varying the functional groups and structural elements of a lead compound, its interaction with the active site of the target protein, as well as its physicochemical, pharmacokinetic, and dynamic properties can be improved. In this context, the introduction of fluorine into active ingredients has become an important concept in the quest for a modern crop protection product with optimal efficacy, environmental safety, user friendliness, and economic viability. Fluorinated organic compounds represent an important and growing family of commercial agrochemicals. A number of recently developed agrochemical candidates represent novel classes of chemical compounds with new modes of action; several of these compounds contain new fluorinated substituents. However, the complex structure-activity relationships associated with biologically active molecules mean that the introduction of fluorine can lead to either an increase or a decrease in the efficacy of a compound depending on its changed mode of action, physicochemical properties, target interaction, or metabolic susceptibility and transformation. Therefore, it is still difficult to predict the sites in a molecule at which fluorine substitution will result in optimal desired effects.

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“…The polarizability α was involved in many equations (Tables S3, S4, S6 to S9), but the atom self-polarizability (ALP ij ;Berger et al, 2001;Berger et al, 2002;Tehan et al, 2002b;Von Oepen et al, 1991), the second (α 2 ) and third (α 3 ) principal polarizabilities (Dunnivant et al, 1992), and the polarizability of the hydroxyl oxygen atom in an acid (α O ) were also used. Other polarizability terms are specially used in linear solvation energy relationships (LSER) equations (see section 2.8).…”

Section: Quantum-chemical Descriptorsmentioning

confidence: 99%

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

Mamy¹,

Patureau²,

Barriuso³

et al. 2014

Critical Reviews in Environmental Science and Technology

117

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A comprehensive review of quantitative structure-activity relationships (QSAR) allowing the prediction of the fate of organic compounds in the environment from their molecular properties was done. The considered processes were water dissolution, dissociation, volatilization, retention on soils and sediments (mainly adsorption and desorption), degradation (biotic and abiotic), and absorption by plants. A total of 790 equations involving 686 structural molecular descriptors are reported to estimate 90 environmental parameters related to these processes. A significant number of equations was found for dissociation process (pKa), water dissolution or hydrophobic behavior (especially through the KOW parameter), adsorption to soils and biodegradation. A lack of QSAR was observed to estimate desorption or potential of transfer to water. Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight. Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters. This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

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Quantitative structure–transformation relationships of sulfonylurea herbicides

Cited by 14 publications

References 30 publications

Responses of Active Bacterial and Fungal Communities in Soils under Winter Wheat to Different Fertilizer and Pesticide Regimens

Responses of Active Bacterial and Fungal Communities in Soils under Winter Wheat to Different Fertilizer and Pesticide Regimens

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

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