𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Labelled organophosphorus pesticides. II. Synthesis of carbon-14 labelled N-sec-butyl O-ethyl O-(5-methyl–2-nitrophenyl) phosphoramidothioate (cremart®)

✍ Scribed by Akira Yoshitake; Fumiaki Shono; Takeshi Kamada; Iwao Nakatsuka

Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
260 KB
Volume
13
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

N‐sec‐Butyl O‐ethyl O‐(5‐methyl–2‐nitrophenyl) phosphoramidothioate (Cremart) (I), an organophosphorus herbicide, was labelled with carbon‐14 at the aryl methyl group for metabolic studies. The synthetic procedures are shown in Fig. 1. 1‐Methoxy‐3‐methyl‐^14^C‐benzene was nitrated with fuming nitric acid‐acetic anhydride to give 2‐methoxy‐4‐methyl‐^14^C‐1‐nitrobenzene which on O‐demethylation with boron tribromide gave 5‐methyl‐^14^C‐2‐nitrophenol. Condensation of the latter with N‐sec‐butyl O‐ethyl phosphoramidochloridothioate in the presence of potassium carbonate afforded Cremart‐(aryl methyl‐^14^C)(I) in the overall yield of 9.2% from methanol‐^14^C, which had a specifie activity of 5.96 mCi/mmole.

📜 SIMILAR VOLUMES

Labelled organophosphorus pesticides. I.
Labelled organophosphorus pesticides. I. Synthesis of carbon-14 labelled O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate (sumithion®)
✍ Akira Yoshitake; Kazuo Kawahara; Takeshi Kamada; Michio Endo 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 French ⚖ 366 KB

## Abstract O,O‐Dimethyl O‐(3‐methyl‐4‐nitrophenyl) phosphorothioate (I) (Sumithion®), an organophosphorus insecticide, was labelled with carbon‐14 individually at the aryl methyl and the phenyl ring. The synthetic procedures are shown in Fig. 1 and 2. Coupling reaction of 3‐methoxyphenylmagnesium

Synthesis of phenyl-14C6-labeled o-(4-br
Synthesis of phenyl-14C6-labeled o-(4-bromo-2,5-dichlorophenyl) o-methyl phenylphosphonothioate and o-(4-nitrophenyl) o-ethyl phenylphosphonothioate using a phasetransfer procedure
✍ H. H. Kaegi; W. P. Duncan 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 French ⚖ 169 KB

A recent paper by Yoshitake et. a1.l describing the synthesis of carbon-14 labeled optically active 0-aryl 0-ethyl phenylphosphonothioates prompts us to report on our preparation of two labeled substances of the same compound class, although not in their optically active form. PhosvelTM, 0-(4-bromo-