The synthesis of 38 compounds with structure R-SOn-CHe-SCN, in which R is a heterocyclic radical and n = 0, 1 , or 2 , is described and their fungicidal and phytotoxic activities are discussed.
IntroductionAs described and discussed in a previous paper from these Laboratories, arylsulfonyl-and arylsulfinyl-methyl thiocyanates showed high fungicidal activity, combined with low phytotoxicity. Those properties make these compounds very useful for phytopharmaceutical application. In continuation of this investigations a number of compounds of this type with an aromatic heterocyclic radical was synthesized and screened for fungicidal activity.
Durch Kondensation der Na‐Salze entsprechender heterocyclischer Mercaptane mit Chlormethyl‐thiocyanat in Methanol oder Acetonitril‐Wasser unter Zusatz von NaOH werden 14 Thioäther, z.B. (Ia) dargestellt, die zu den entsprechenden Sulfoxiden, z.B. (Ib), bzw. Sulfonen (Ic) oxidiert werden.
The synthesis and fungicidal and phytotoxic properties of a large number of arylsulfonyl-, arylsulfinyl-, and arylthio-alkyl thiocyanates are described and discussed.
IntroductionSince many thiocyanates exhibit fungicidal properties, the authors sought for a good synthesis of arylsulfonylmethyl thioxyanates and arylsulfkylmethyl thiocyanates. These compounds were unknown in literature until 1964, when Goerdeler and Rosenthal 1 found that 4-chlorobenzenesulfonyl thiocyanate reacted with diazomethane to yield 4-chlorophenylsulfonylmethyl thiocyanate. This method however is not very suitable for the synthesis of larger quantities of the arylsulfonylmethyl thiocyanates. Moreover as the arylsulfinylmethyl thiocyanates could not be obtained in this way other methods had to be developed for the synthesis of arylsulfonylalkyl thiocyanates and the corresponding sulfinyl derivatives, particularly the methyl derivatives.The synthesis and biological properties of aryloxymethyl thiocyanates 2, arylthiomethyl thiocyanates 2, arylthiomethyl isothiocyanates and arylsulfonylalkyl isothiocyanates 4 have already been described.
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