Insecticidal phosphorinanylaminothio derivatives of the carbamate methomyl

Abstract

derivatives of methomyl. Results of those investigations are reported in the following paper (Dutton et al., 1981).

Insecticide metabolism and selective toxicity

“…In the case of phosphorinanylaminothio derivatives of methomyl such as (16) in figure 1, derivatization improved both mammalian (rat oral LD,, > 8000 mg/kg) and plant safety, while preserving the toxicity of the parent carbamate towards a range of lepidopteran pests (Dutton et al 1981). Derivatization of appropriate carbamates with hydrophilic moieties is also under exploration, in an attempt to combine favourable toxicological properties with plant systemic insecticidal activity (Jojima et al 1983).…”

Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity

“…It is possible, for example, to react halogen containing compounds, such as chloroanhydrides of varios P(III) acids with amines giving a P(III)-N bond. In the work of Dutton and coworkers [8], chloro-2-dimethyl-5,5-dioxaphosporinane-1,3,2 was reacted with various amines, such as tert-butylamine resulting in the formation of several 1,3,2 dioxaphosporinanes. A similar approach was adopted by Browne et al [9] where phosporochloridite was reacted with amines followed by reaction with elemental sulfur to obtain potential insecticides.…”

Multiphase photodegradation of methyl N-[[[[[(1,1-dimethylethyl)(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)amino]thio]methylamino]carbonyl]oxy]ethanimidothioate

“…Methyl (5,5-dimethyl-2-thioxo-l,3,2-dioxaphosphorinan-2-yl)amino]thio]methylamino] carbonyl] oxy] ethanimidothioate (I) is an experi- Thiophosphoramide (III) mental compound that has shown good activity for control of various lepidopterous pests in several agronomic and horticultural crops (Dutton et al, 1981). The structure of I shows that the carbamate portion is methomyl (II),…”