(Nitroethenyl)salicylic Acid Anilides and Related Substances, a New Group of Molluscicidal and Microbicidal Compounds

Abstract

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'.

Nitro-functionalized analogues of 1,3-Butadiene: An overview of characteristic, synthesis, chemical transformations and biological activity

“…The authors mentioned that the addition in chlororoform proceeds slowly and in effect the reaction leads to only one product which is 3,4-dibromo-2-nitro-1-butene (13). In turn, application of a more polar solvent such as acetic acid led to formation of 1,2,3,4-tetrabromo-2-nitro-1-butene (14). Scheme 8.…”

“…1 What is more, the presence of nitro group conjugated with ethylene moiety >C=C< additionally stimulates the biological activity of the compounds. In the effect, CNAs are characterised by antibacterial [3][4] and antifungal 14 properties. A question arises, since CNAs can be useful building block for application in chemical synthesis, thanks to the presence of nitrovinyl moiety, what possibilities can be offered by a molecule containing a double bond conjugated with this nitrovinyl fragment?…”

Synthesis of Furo‐salicylanilides and Their Heterocyclic Derivatives with Anticipated Molluscicidal Activity

“…The toxicity of the products towards Biomphalaria alexandrina snails, the intermediate host of Schistosoma mansoni, which affects the intestinal system in man, was carried out according to the standard method [3,19,20].…”

(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

“…Among all nitro compounds, a class of conjugated nitroalkenes (CNAs) deserves special attention [ 3 , 4 ]. These compounds exhibit various biological activities such as antibacterial [ 5 , 6 ] or antifungal [ 7 ]. This makes CNAs often used in many reactions such as Michael addition [ 8 , 9 ] as well as cycloaddition (CA) reactions, to synthesize heterocycles, especially for the preparation of five-membered rings [ 10 ] like pyrazolines [ 11 , 12 ], isoxazolines [ 13 , 14 , 15 , 16 ] or pyrrolidine [ 17 , 18 ], and six-membered rings in the Diels-Alder reaction [ 19 , 20 , 21 ].…”