N-Sulfonyl Amino Acid Amides, a Novel Class of Compounds with Fungicidal Activity [1]

Abstract

Novel types of oomycete fungicides have been designed and prepared. The synthetic approach to these N-sulfonyl amino acid amides is outlined. Bioassays demonstrate their high efficacy against important plant diseases like Phytophthora infestans (tomato and potato late blight) and Plasmopara viticola (grape downy mildew). Structure–activity relationship studies are discussed.

The Significance of Organosulfur Compounds in Crop Protection: Current Examples from Fungicide Research

“…25 Its concise synthesis starts from 4-methoxy-2-methylaniline (32), which is converted by Skraup-type cyclization 26 5). 28,29 The N-terminal group of the phenylglycinamides plays an important role for the fungicidal efficacy. 29 A free NH 2 (entry 1) or the incorporation of this amino group into an amide or carbamate function (entries 2 and 3) led to totally inactive compounds (Table 2).…”

“…28,29 The N-terminal group of the phenylglycinamides plays an important role for the fungicidal efficacy. 29 A free NH 2 (entry 1) or the incorporation of this amino group into an amide or carbamate function (entries 2 and 3) led to totally inactive compounds (Table 2). Therefore it has been an important discovery that the substitution with an alkylsulfonyl group delivers completely different results.…”

“…The nucleophilic substitution of its bromine substituent by an ethylthiolate anion delivers the O,S-acetal 41, which is further converted by standard ester saponification and amide coupling into the target compound 43, a close analog of 37, in which only one methyl group was shifted from one part of the molecule to another one (Scheme 4).3.3. Cellulose synthase inhibitorsN-sulfonyl-and N-sulfamoylphenylglycinamides, such as 51, belong together with other amino acid amides, such as valinamides and also with -alkoxycarboxamides, such as mandelamides, to a family of Cellulose synthase inhibitors, which are highly active against downy mildew diseases 28,29. The synthesis of 51 starts from vanilline (44), which is converted into its cyanohydrine 45.…”

Syntheses, Crystal Structures, and Thermal Properties of Two Transition Metal Complexes With 4-Chlorobenzenesulfonyl-glycine Acid Ligand

“…In addition, N-sulfonyl-amino acids may act not only as the hydrogen bond donors but also as acceptors, which make it a wonderful candidate for the construction of supramolecular structures. Therefore, it is of great interest to study the coordination chemistry of N-sulfonyl-amino acids [16][17][18][19] . In our previous studies, we have successfully prepared three N-sulfonyl-amino acids complexes.…”

Synthesis of Substituted Mandelic Acid Derivatives via Enantioselective Hydrogenation: Homogeneous versus Heterogeneous Catalysis

“…Substrates: Methyl phenylglyoxylates (9a and 9b) were prepared according to standard Friedel±Crafts acylation procedures, [8,9] 4-chlorophenylglyoxylic acid amide (6a; mp 119 ± 120 8C) was obtained from 4-chlorophenylglyoxylic acid [9] and 2-(4-hydroxy-3-methoxyphenethyl)amine [10] under standard peptide coupling conditions with the aid of Castro×s reagent and H¸nig×s base. Subsequent acetylation with acetic anhydride and potassium carbonate or benzylation with benzyl chloride led to the amides 6b (mp 131 ± 133 8C) and 6c, respectively.…”