Synthesis and insecticidal activity of 4‐(aminomethyl)‐2 H ‐1‐benzothiopyran‐2‐ones (thiocoumarins) and related compounds | Zendy

Nakazumi Hiroyuki | Zendy; Kobara Yuzoh | Zendy; Kitao Teijiro | Zendy

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Synthesis and insecticidal activity of 4‐(aminomethyl)‐2 H ‐1‐benzothiopyran‐2‐ones (thiocoumarins) and related compounds

Author(s) -

Nakazumi Hiroyuki,

Kobara Yuzoh,

Kitao Teijiro

Publication year - 1992

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570290124

Subject(s) - chemistry , spodoptera litura , tetranychus urticae , bromine , stereochemistry , organic chemistry , medicinal chemistry , botany , lepidoptera genitalia , biology , acari

Bromination of 4‐methyl‐2 H ‐1‐benzothiopyran‐2‐ones (4‐methylthiocoumarins) with bromine under irradiation of high‐pressure mercury lamp gave 3‐bromo‐4‐methylthiocoumarin, which reacted with secondary amine to give 4‐(aminomethyl)thiocoumarins. The structure was determined by X‐ray crystallographic analysis. A series of 4‐methylthiocoumarin and related compounds were tested for insecticidal activity, and 4,6‐dimethylthiocoumarin shows the most significant insecticidal activity against Nilaparvata lugens and Aphis gossypii . An introduction of an aminomethyl group in thiocoumarin results in improvement of activity against Tetranychus urticae and Spodoptera litura .

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