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5-(2-Nitroethenyl)salicyloyl chloride (2 b) condenses with anilines affording the anilides 3a-h. The compound 3a reacts with isocyanates to give the corresponding carbarnates 5a-c, whereas at higher temperatures the anilide 3a as well as the acid 2a give the same benzoxazinedione 4 a which affords 5-formyl-N-methylsalicylamide (6) upon treatment with alkali. 3a and 3d react with thionyl chloride to give the corresponding 2-chloro-5-(2-nitroetheny1)benzanilides 8a and 8b. Spectral features of the compounds are discussed and their molluscicidal and microbicidal activities are presented. Mit Thionylchlorid reagieren 3a und 3d zu den entspechenden 2-Chlor-5-(2-nitroethenyl)-benzaniliden 8 a bzw. 8 b. Die spektroskopischen Merkmale der Verbindungen werden diskutiert, und iiber die molluskiziden und mikrobiziden Eigenschaften wird berichtet.Several synthetic organic compounds proved to be toxic to aquatic snails and some of these compounds are now used as molluscicides in prevention of parasitic diseases. An important group of molluscicides are the salicylanilides, the most active member of which turned out to be 2',5-dichloro-4'-nitrosalicylanilide (1) which is now used successfully in combating snails for control of schistosomiasis in endemic areas1). On the other hand, it has been shown in our laboratory that some aryl-and heteroaryl-substituted nitroalkenes possess molluscicidal properties characterized by a well defined knock-down effect".In the light of the aforementioned reports and in the course of our program in search of new molluscicides, it was interesting to construct molecules incorporating both the salicylanilide and nitroethenyl moieties in an attempt to obtain compounds which possibly would combine the biological properties of both or synergize any of these activities.For this purpose, 5-formylsalicylic acid was condensed with nitromethane in acetic acid in the presence of n-butylamine'), to give 5-(2-nitroethenyl)salicylic * ) This procedure proved to be superior to that previously described using ammonium 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1985 acetate in acetic acid3'.

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ChemInform Abstract Cyclocondensation of the 2-hydroxychalcones (I) with the isocyanates (II) in the presence of potassium hydroxide yields directly the title compounds (III), whereas reaction of (I) with methyl isocyanate (IIa) in the presence of triethylamine forms the carbamates (IV). These are cyclized upon treatment with potassium hydroxide, giving the benzoxazinone derivatives (IIIa) which are also obtained by condensation reaction of the 4-hydroxydihydrobenzoxazinones (V) with the acetophenones (VI). Methyl isothiocyanate (VII) reacts similarly with (I), forming the thiones (VIII) which are converted to the corresponding oxo compounds (IIIa) by oxidation with yellow mercury oxide. The tosylates (X) are also prepared.