A new pyrethroid‐type ester with strong knockdown activity

Hirano, Masachika; Itaya, Nobushige; Ohno, Isao; Fujita, Yoshio; Yoshioka, Hirosuke

doi:10.1002/ps.2780100403

Cited by 10 publications

(14 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1. The total 14 C recovery was 86.4-107.5% of the applied 14 C. As with incubation, extractable 14 C gradually decreased finally to 6.1-12.9% at day 60 with a significant formation of CO 2 amounting to 51.0-68.0%. The amount of soil-bound residues also increased with time and peaked at day 30 (24.8-32.6%) but slightly decreased afterwards.…”

Section: Aerobic Soil Metabolism Of Ipmentioning

confidence: 90%

“…(1R)-Cis and (1R)-trans isomers of IP, separately labeled with 14 C at the 5-position of the imidazolidinyl ring (Fig. 4) were synthesized in our laboratory.…”

Section: Chemicalsmentioning

confidence: 99%

“…The non-radiolabeled isomers of IP, PGH (1-propargylimidazolidine-2,4-dione), CPG-Me (methyl Ncarbamoyl-N-propargylglycinate) and PG (N-propargylglycine), whose chemical structures are shown in Table 1, were also synthesized in our laboratory according to the reported methods. 14,20,21) The chemical purity of each standard was determined to be Ͼ93% by high-performance liquid chromatography.…”

Section: Chemicalsmentioning

confidence: 99%

“…The unextractable soil-bound residues were powdered after drying in a vacuum desiccator and their portion was subjected to combustion analysis using a Packard Model 307 sample oxidizer under the 14 C recovery of Ͼ95%. Details of these measurements have been previously reported.…”

Section: Radioassaymentioning

confidence: 99%

“…12) Therefore, pyrethroids are most unlikely to contaminate groundwater as compared with atrazine and sulfonylurea herbicides showing much less adsorption to soil. 13) Imiprothrin (IP) [Pralle ® , 2,5-dioxo-3-prop-2-ynylimidazolidin-1-ylmethyl (1R)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-carboxylate] (cis/transϭ20/80) is a potent knock-down insecticide 14) uniquely having an imidazolydinyl ring instead of 3-phenoxybenzyl or a-cyano-phenoxybenzyl moiety in phenothrin and cyphenothrin. Although rat metabolism 15,16) and abiotic hydrolysis 17,18) have been studied for IP, its environmental profiles such as metabolism and mobility in soil have not been examined because of its indoor usage for public hygiene (i.e.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Aerobic metabolism and adsorption of pyrethroid insecticide imiprothrin in soil

2006

View full text Add to dashboard Cite

Imiprothrin, a unique type of pyrethroid having an imidazolidinyl ring in its alcohol moiety, was rapidly degraded in two aerobic U.S. soils. The half-lives of biologically active trans isomer were estimated by assuming the first-order kinetics to be 1.6-2.5 days, shorter than those of the cis isomer (3.3-12.5 days). The primary metabolic pathway was ester cleavage followed by instantaneous elimination of a hydroxylmethyl group from the alcohol moiety to form PGH (1-propargylimidazolidine-2,4-dione). The opening of the imidazolidinyl ring with subsequent release of the carbamoyl group resulted in the formation of PG (N-propargylglycine). The soil adsorption coefficients (K oc ) of the trans isomer, the main component of imiprothrin (80%), to the two soils were determined to be 376 and 428 (ml/g o.c.) by the batch equilibrium method and these lower values as compared with other pyrethroids were likely to stem from the hydrophilic character of the alcohol moiety. Based on the metabolic half-lives and K oc values, the groundwater concentration of imiprothrin was calculated to be 0.039 mg/L by using the screening simulation model SCI-GROW known to give a conservative groundwater concentration. This significant lower concentration clearly indicates that imiprothrin is most unlikely to contaminate the groundwater, mainly due to its rapid degradation in soil.

show abstract

Section: Aerobic Soil Metabolism Of Ipmentioning

confidence: 90%

“…(1R)-Cis and (1R)-trans isomers of IP, separately labeled with 14 C at the 5-position of the imidazolidinyl ring (Fig. 4) were synthesized in our laboratory.…”

Section: Chemicalsmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

Section: Radioassaymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Aerobic metabolism and adsorption of pyrethroid insecticide imiprothrin in soil

2006

View full text Add to dashboard Cite

show abstract

Synthetic pyrethroids containing a C-C triple bond

Matsuo

1998

Pestic. Sci.

View full text Add to dashboard Cite

:The three commercial synthetic pyrethroids containing a carbonÈ carbon triple bond, a-ethynyl-2-methylpent-2-enyl (1R)-trans-chrysanthemate, (S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-trans,cis-chrysanthemate and [2,5-dioxo-3-(2-propynyl)-1-imidazolidinyl]methyl (1R)-trans-chrysanthemate are reviewed with emphasis on their inventive histories. Their chemistry and efficacy are described brieÑy. The relationship between stereochemistry and the biological activity is also discussed.

show abstract

Pyrethroids

Pap¹

2002

Encyclopedia of Agrochemicals

View full text Add to dashboard Cite

The insecticidal synthetic pyrethroids are chemical analogs of the natural pyrethrins occurring in the flower of the Chrysanthemum cinerariaefolium plant. They represent an extensively developed insecticide group with 40 established compounds. Of the 40 commercialized active ingredients, 37 are esters. The application rate of the most potent agricultural pyrethroids is very low, ranging between 5 and 20 g/ha, representing an acceptable environmental load. Pyrethroids are also regarded as safe compounds to warm‐blooded animals and generally to the environment; however, they have some adverse effects on mites, beneficial insects, and aquatic organisms. Pyrethroids are contact nerve poisons acting on gating kinetics of sodium channel in nerve membrane. This action is highly stereoselective. Due to this specific action and their extensive use, the risk of resistance development is relatively high in the targeted insect pest populations. Consequently, resistance management strategies are urgently needed to sustain their appropriate field performance. The registered tendencies of pyrethroid usage and the recent trends in R&D both suggest that this particular group of compounds has been playing an integrated part in present pest management as it is described in our comprehensive survey. Natural Pyrethrin PyrethrinI as the Lead Structure of the Synthetic Pyrethroids Stereochemistry How to Define Pyrethroids Nomenclature Physicochemical Properties Agricultural Use Chemistry Biological Activity, Mode of Action, Metabolism

show abstract

A new pyrethroid‐type ester with strong knockdown activity

Cited by 10 publications

References 6 publications

Aerobic metabolism and adsorption of pyrethroid insecticide imiprothrin in soil

Aerobic metabolism and adsorption of pyrethroid insecticide imiprothrin in soil

Synthetic pyrethroids containing a C-C triple bond

Pyrethroids

Contact Info

Product

Resources

About