Degradation and Leaching Behavior of the Pyrethroid Insecticide Fenpropathrin in Soils

Sakata, Shinoi; Yoshimura, Jun; Nambu, Kenji; Mikami, Nobuyoshi; Yamada, Hirohiko

doi:10.1584/jpestics.15.363

Cited by 7 publications

(6 citation statements)

References 3 publications

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“…At a moisture content greater than 50%, the degradation profiles of I were close to those found in the aerobic and anaerobic soil metabolism. 3 The degradation pathways changed to the ester cleavage finally forming X and hydroxylation at the 3-phenoxybenzyl moiety from the formation of VI and VII. Therefore, it was strongly suggested that the surface acidity of clay dependent on a moisture content mainly determined the degradation rate of I as well as a formation of VI.…”

Section: Discussionmentioning

confidence: 99%

“…25 mm layer thickness, E. Merck) chromatography with the solvent systems, benzene saturated with formic acid/ diethyl ether (10/3) and hexane/toluene/acetic acid (3/15/2), was conducted to separate and quantify photoproducts derived from I, as previously reported.3,5) To separate IV and V more clearly by TLC, the other solvent system (hexane/acetone, 4/1) was used in the multiple development (twice in the same direction). 3 The resolved radioactive spots were detected by autoradiography with the developed TLC plates held under X-ray SB film (Eastman Kodak Company) at 4C for a week. The chemical identity of each photoproduct was confirmed by cochromatography with the unlabeled standard chemicals.…”

Section: Tlcmentioning

confidence: 99%

“…10,11 The soil thin-layers used in the photodegradation are in an air-dried state, 5,9,11 while soils in the metabolism studies have been moistened to 40-50% of a maximum waterholding capacity. 3,8,10) The effect of a moisture content on the aerobic soil metabolism has been briefly examined for I and more amount of the amide derivative has been detected in the soil at a lower moisture content,12) but its mechanism is not clear.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Moisture Content and UV Irradiation on Degradation of Fenpropathrin on Soil Surfaces

Katagi¹

1993

J. Pestic. Sci.

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The effect of a moisture content and UV irradiation on the degradation of the pyrethroid insecticide fenpropathrin (I) [(RS)-a-cyano-3-phenoxybenzy12,2,3,3-tetramethylcyclopropanecarboxylate] on soil surfaces was examined using a xenon lamp (A>290 nm). I was rapidly degraded at a lower moisture content of soil via hydration of the a-cyano group and UV irradiation was found to slightly facilitate the degradation.As with an increase of moisture, the degradation pathways previously reported in aerobic and anaerobic soil metabolism became predominant on the soil surfaces. The marked change of a surface acidity of clay with a moisture content was likely to account for the moisture dependency of the degradation.

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Section: Discussionmentioning

confidence: 99%

Section: Tlcmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of Moisture Content and UV Irradiation on Degradation of Fenpropathrin on Soil Surfaces

Katagi¹

1993

J. Pestic. Sci.

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“…We paid attention to the facts that they are minor products in soil metabolism under the water content kept at ca. 50% of a maximum waterholding capacity (MWHC), 41) and that the slower dissipation of fenpropathrin had been reported in the field by the soil mixing application of its formulation, as compared with its spray application to the soil surface. 42) Incidentally, the α-amide derivative was formed significantly (4-36%) on the soil thin-layer without controlling the soil water content in the photodegradation study, and the insignificant differences in its formation were observed between sunlight exposure and dark conditions, 43) showing that photolysis is of minor importance.…”

Section: Chemical Reactions In/on Soilmentioning

confidence: 99%

Theoretical and organic chemical approaches to environmental behavior and metabolism of pesticides

Katagi

2020

J. Pestic. Sci.

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Investigation of the dissipation and transformation of pesticide through laboratory experiments, conducted in accordance with standard and newly developed designs, gives us valuable information to understand their environmental behavior. We have also been investigating the mechanisms of partition and transformation reactions of pesticides, not only through kinetic analyses, but also through theoretical approaches based on their molecular properties estimated using various spectroscopies and molecular orbital calculations. Furthermore, synthetic iron porphyrin with a peroxide was shown to be a good model to simulate the P450catalyzed oxidation in the metabolism of pesticides. Through these investigations, the knowledge of surface water, soil, sediment, and plants, such as their properties and constituents, was found indispensable to a deep understanding of the mechanism in the hydrolysis, photolysis, and metabolism of pesticides.

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“…Hydrolysis of the ester linkage producing 3-phenoxybenzoic acid (3-PBA) and 3-(2′,2′-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (DCCA) is the main degradation pathway of cypermethrin in soil (structures B and C of Figure ). DCCA and 3-PBA are frequently detected in the environment and humans. − As a general degradation product of pyrethroids, 3-PBA is classified as an endocrine disrupting chemical, owning to its antiestrogenic activity. Furthermore, 3-PBA also has higher mobility than the parent compounds, causes widespread contamination in soil, , and thus, may pose potential influence on soil organisms.…”

Section: Introductionmentioning

confidence: 99%

Chiral Insecticide α-Cypermethrin and Its Metabolites: Stereoselective Degradation Behavior in Soils and the Toxicity to Earthworm Eisenia fetida

Yao

Jing

Wang

et al. 2015

J. Agric. Food Chem.

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The enantioselective degradation of the widely used chiral insecticide α-cypermethrin in soils has been investigated, and its main metabolites cis-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (cis-DCCA) and 3-phenoxybenzoic acid (3-PBA), which have potential environmental problems, have also been determined. The enantiomers of α-cypermethrin were separated on Chiralcel OD chiral columns by high-performance liquid chromatography (HPLC) under normal phase, and the metabolites were detected by gas chromatography (GC) after derivatization. The results of the degradation showed that α-cypermethrin dissipated in soils with relatively long half-lives of 12.70-47.08 days and obvious stereoselective degradation of the two enantiomers was observed in the five soils, with enantiomeric fraction (EF) from 0.55 to 0.61 after 42 days, indicating that (+)-(1R,cis,αS) enantiomer was preferentially degraded. cis-DCCA and 3-PBA were formed in all of the soils, and it was found that the amount generated was related to the soil pH. cis-DCCA was easily generated in the acidic soils, while more 3-PBA tended to be generated in the soil of pH over 7. To evaluate the impact on soil animals, the toxicity, including the combined toxicity of cis-DCCA, 3-PBA, and α-cypermethrin, to earthworm (Eisenia fetida) was studied. The results of enantioselective transformation of α-cypermethrin in soils and the toxicity of α-cypermethrin and its metabolites to earthworm have some implications for environmental risk and food safety evaluations.

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Degradation and Leaching Behavior of the Pyrethroid Insecticide Fenpropathrin in Soils

Cited by 7 publications

References 3 publications

Effect of Moisture Content and UV Irradiation on Degradation of Fenpropathrin on Soil Surfaces

Effect of Moisture Content and UV Irradiation on Degradation of Fenpropathrin on Soil Surfaces

Theoretical and organic chemical approaches to environmental behavior and metabolism of pesticides

Chiral Insecticide α-Cypermethrin and Its Metabolites: Stereoselective Degradation Behavior in Soils and the Toxicity to Earthworm Eisenia fetida

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