Phenylamides

Figure 3. Proposed chemical reactions leading to stabilization of phenylamide, phenylcarbamate and phenylurea pesticides In soils. (From ACS Symposium Series No. 29, 1976) (173).

Figure 1 N-carboxylalkyl inhibitor of sfSTR, N-[(R)-carboxyl-ethyl]-(S)-(2-phenylethyl) glycyl-L-arginine-N-phenylamide [8]. The convention of Schechter and Berger [61 ] is used to describe the specificity subsites of the enzyme Si, S2, S3 which correspond to the side chains P/, P2, P3 of the inhibitor. (From Ref. 5.)... 

Displacement of the 3-hydroxyl group of 74 was carried out with Et2NSF3 (DAST) (DAST - diethylaminosulfur trifluoride) in dichloromethane. The expected fluorinated product 75 on treatment with aqueous perchloric acid led to regioselective epoxide ring opening to give 76, which on treatment with hydrazine hydrate at 100 °C for 18 h yielded 3,4-dihydroxy-8-oxo-octahydropyridazino[l,6-r/][l,2,4]triazine-l-carboxylic acid phenylamide 77 (Scheme 3) <1997T9357>. 

A different mechanism probably operates for the reaction of TV-hydroxy-TV-phenylamides in the presence of (m-Bu)3P, CCI4 and MeCN, with the 2-isomer in the product53 suggestive of some intramolecular pathway as outlined in Scheme 8. 

Several compounds may interfere with nucleic acid metabolism but commonly their effects are secondary to their primary mode of action, for example, the benzimidazoles. Compounds that inhibit nucleic acid biosynthesis directly are either phenylamides, pyrimidines or hydroxy-pyrimidines. Recently, the phenoxyquinolines were identified as exhibiting a novel mode of action in purine biosynthesis and are potentially useful fungicides. 

RNA Synthesis. The phenylamides comprise a diverse group of systemic compounds of which the acylalanines are the most successful (Figure 4.11). The acylalanine fungicides are systemic, mainly via the... 

In their studies the enzyme activity decreased when reagents were added that complex with thiols hence it was concluded that cysteine was probably the key enzymatic nucleophile. The production of this enzyme could be induced by exposure of the bacteria to various phenylamide- or phenylurea-containing herbicides and fungicides. The enzyme was also capable of hydrolyzing a variety of other phenylamides and phenylureas, albeit at somewhat different rates. 

Englehardt, G., P. R. Wallnofer, and R. Plapp, Purification and properties of an aryl acylamidase of Bacillus sphaericus, catalyzing the hydrolysis of various phenylamide herbicides and fungicides , Appl. Microbiol., 26,709-718 (1973). 

MA El-Dib, OA Aly. Colorimetric determination of phenylamide pesticides in natural waters. J Assoc Anal Chem 55 1276-1279, 1972. 

Reduction of 4-(65) gave aldehyde 42 in strong acid and carbinol 31 in acetate buffer.99 In alkaline electrolyte, 31 would be further reduced to the picoline (19) (Scheme 19). The IV-phenylamide gave a mixture of the carbinol... 

The reaction of phenylamide ions with Phi stimulated by K metal gave diphenylamine (19%), o- and p-phenylanilines (11% each)3. However, the photostimulated reaction of phenylamide ions with Phi, p-iodoanisole and p-iodobenzonitrile was quite sluggish (ca 8% in 3 h)223. 

S.G.P = denomination of-" permitted explosives in Belgium S-FI-process (RDX-synthesis) 68 shaped charge 42 67 283 sheathed explosives 284 shelf life (storage life) 114 285 Shellite (UK) = Tridite (USA) = mixtures of picric acid and hexanitrodi-phenylamide... 

The X-ray crystal structure of 3,4-dichoro-l//-pyrrole-2,5-dicarboxylic acid bis-phenylamide tetrabutylammonium salt reveals the formation of an unusual dimer in the solid state via amide NFI- -N pyrrole hydrogen bonds... 

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