The chiral pyrethroid cycloprothrin: Stereoisomer synthesis and separation and stereoselective insecticidal activity

Biao Jiang; Hua Wang; Qun Mei Fu; Zhu Yi Li

doi:10.1002/chir.20508

The chiral pyrethroid cycloprothrin: Stereoisomer synthesis and separation and stereoselective insecticidal activity

Biao Jiang, Hua Wang, Qun Mei Fu, Zhu Yi Li

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The synthesis and separation of the isomers of the pesticide cycloprothrin have been realized for the first time. Complete separation was achieved on a DAICEL CHIRALCEL® OJ-H column (25 x 0.46 cm) for (1R, a*)- cycloprothrin isomers and on a DAICEL CHIRALCEL OD-H column (25 x 0.46 cm) for (1S, a*)-cycloprothrin isomers. The insecticidal activity of (1R, αR)-cycloprothrin for the larvae of Mythimaseparata and Aphismedicagini was found to be about six times and four times higher, respectively, than that of racemic cycloprothrin.

Original language	English (US)
Pages (from-to)	96-102
Number of pages	7
Journal	Chirality
Volume	20
Issue number	2
DOIs	https://doi.org/10.1002/chir.20508
State	Published - Feb 2008
Externally published	Yes

Keywords

Chiral cycloprothrin
Chiral separation
Insecticidal activity
Pyrethroid

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.20508

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abstract = "The synthesis and separation of the isomers of the pesticide cycloprothrin have been realized for the first time. Complete separation was achieved on a DAICEL CHIRALCEL{\textregistered} OJ-H column (25 x 0.46 cm) for (1R, a*)- cycloprothrin isomers and on a DAICEL CHIRALCEL OD-H column (25 x 0.46 cm) for (1S, a*)-cycloprothrin isomers. The insecticidal activity of (1R, αR)-cycloprothrin for the larvae of Mythimaseparata and Aphismedicagini was found to be about six times and four times higher, respectively, than that of racemic cycloprothrin.",

keywords = "Chiral cycloprothrin, Chiral separation, Insecticidal activity, Pyrethroid",

author = "Biao Jiang and Hua Wang and Fu, {Qun Mei} and Li, {Zhu Yi}",

year = "2008",

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doi = "10.1002/chir.20508",

language = "English (US)",

volume = "20",

pages = "96--102",

journal = "Chirality",

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T1 - The chiral pyrethroid cycloprothrin

T2 - Stereoisomer synthesis and separation and stereoselective insecticidal activity

AU - Jiang, Biao

AU - Wang, Hua

AU - Fu, Qun Mei

AU - Li, Zhu Yi

PY - 2008/2

Y1 - 2008/2

N2 - The synthesis and separation of the isomers of the pesticide cycloprothrin have been realized for the first time. Complete separation was achieved on a DAICEL CHIRALCEL® OJ-H column (25 x 0.46 cm) for (1R, a*)- cycloprothrin isomers and on a DAICEL CHIRALCEL OD-H column (25 x 0.46 cm) for (1S, a*)-cycloprothrin isomers. The insecticidal activity of (1R, αR)-cycloprothrin for the larvae of Mythimaseparata and Aphismedicagini was found to be about six times and four times higher, respectively, than that of racemic cycloprothrin.

AB - The synthesis and separation of the isomers of the pesticide cycloprothrin have been realized for the first time. Complete separation was achieved on a DAICEL CHIRALCEL® OJ-H column (25 x 0.46 cm) for (1R, a*)- cycloprothrin isomers and on a DAICEL CHIRALCEL OD-H column (25 x 0.46 cm) for (1S, a*)-cycloprothrin isomers. The insecticidal activity of (1R, αR)-cycloprothrin for the larvae of Mythimaseparata and Aphismedicagini was found to be about six times and four times higher, respectively, than that of racemic cycloprothrin.

KW - Chiral cycloprothrin

KW - Chiral separation

KW - Insecticidal activity

KW - Pyrethroid

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The chiral pyrethroid cycloprothrin: Stereoisomer synthesis and separation and stereoselective insecticidal activity

Abstract

Keywords

ASJC Scopus subject areas

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