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14C-labelling of optically active fenvalerate, α-cyano-3-phenoxy-benzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate (I)

✍ Scribed by Akira Yoshitake; Hiroshi Kanamaru; Fumiaki Shono; Iwao Nakatsuka

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
473 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

(S)‐Fenvalerate (α‐cyano‐3‐phenoxybenzyl) (S)‐2‐(4‐chlorophenyl)‐3‐methylbutyrate, a novel insecticide, was labelled with carbon‐14 individually at the carbonyl (1a), the cyano (1b) and the alcoholic methyne (1c) carbons for use in metabolic studies. Isopropylation of 4‐chlorophenylacetonitrile‐^14^C with isopropyl bromide followed by hydrolysis gave racemic 2‐(4‐chlorophenyl)‐3‐methylbutyric‐1‐^14^C acid, which on optical resolution with (−)‐1‐phenylethylamine gave the (S)‐acid. Esterification of the (S)‐acid with α‐cyano‐3‐phenoxybenzyl bromide gave 1a in 18% yield from potassium cyanide‐^14^C. Esterification of α‐cyano‐^14^C‐3‐phenoxybenzyl alcohol with (S)‐2‐4‐chlorophenyl‐3‐methyl‐butanoyl chloride (9) gave 1b in 65% yield. Condensation of 3‐phenoxybenzaldehyde‐(carbonyl‐^14^C), prepared from 3‐phenoxybenzoic‐^14^ C acid, with 9 and sodium cyanide gave 1c in 54% yield from barium carbonate‐^14^C.

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14C-labeling of a novel fungicide. I. Sy
14C-labeling of a novel fungicide. I. Syntheses of optically active (E)-and (Z)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-[14C]-1-YL)-1-penten-3-OLS
✍ Iwao Nakatsuka; Hiroshi Kanamaru; Takeshi Kamada; Kazuo Kawahara; Akira Yoshitak 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 French ⚖ 384 KB

A novel fungicide, (-) (E)-1-( 2,4-di chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (S-3308 L) and i t s three o p t i c a l l y active stereoisaners were labeled w i t h carbon-14 a t the t r i a z o l e r i n g f o r use i n the metabolic and environmental f a t e studies. 1 ,2,