Chemical Reactivity of Oxidation Products of the Dithiolanylidenemalonate Fungicide, Isoprothiolane.
Diisopropyl dithiolanylidenemalonate (isoprothiolane) was oxidized with m-chloroperbenzoic acid to give a monosulfoxide, disulfoxide, and disulfone. The monosulfoxide was subjected to addition reactions with such nucleophiles as methanol, thiols, and amines at the thioacetal carbon to open the dithiolane ring, affording a thiosulfinate, sulfinate and disulfide. The presence of a small amount of sodium carbonate accelerated the reactions and, moreover, reformed isoprothiolane from the ring-opened addition products. The further oxidation products were transformed into dithianes by reacting with nucleophiles. Isoprothiolane monosulfoxide inhibited alcohol dehydrogenase, an SH enzyme.
a Department of Agricultural Chemistry , Kyushu University , Fukuoka 812 , Japan.
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Ikeda
a Department of Agricultural Chemistry , Kyushu University , Fukuoka 812 , Japan.
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Ishibashi
a Department of Agricultural Chemistry , Kyushu University , Fukuoka 812 , Japan.
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Shiotsuki
a Department of Agricultural Chemistry , Kyushu University , Fukuoka 812 , Japan.
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E
Kuwano
a Department of Agricultural Chemistry , Kyushu University , Fukuoka 812 , Japan.
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Eto