Methylene Group Modifications of the N-(Isothiazol-5-yl)phenylacetamides. Synthesis and Insecticidal Activity
| Autor: | Jon M. Babcock, Michelle L. Schlenz, George W. Johnson, Jack Geno Samaritoni |
|---|---|
| Rok vydání: | 1999 |
| Předmět: |
chemistry.chemical_classification
Insecticides Insecta Molecular Structure Chemistry Thio General Chemistry Moths Spodoptera Chemical synthesis Enol Amino acid Structure-Activity Relationship Thiazoles chemistry.chemical_compound Aphids Amide Acetamides Functional group Animals Organic chemistry Methylene General Agricultural and Biological Sciences Acetamide |
| Zdroj: | Journal of Agricultural and Food Chemistry. 47:3381-3388 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/jf990095s |
| Popis: | It has been shown that oxidation at the α-carbon of N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl]acetamide (1) is conveniently brought about using dimethylformamide dimethylacetal to give N-(4-chloro-3-methyl-5-isothiazolyl)-β-(dimethylamino)-p-[(α,α,α-trifluoro-p-tolyl)oxy]atropamide (2), which has served as a common starting point for a variety of functional group transformations. These transformations were found to proceed in moderate to good yields to give derivatives of 1 that retained much of the efficacy associated with the parent amide and have allowed for an expansion of the SAR to be developed. Examples of enamines, enols, enol (thio)ethers, oximes, and hydrazones were prepared. In particular, the enamines derived from low molecular weight amines and amino acids were most active as broad-spectrum insecticides and were found to be even more active than 1 on root-knot nematode. Keywords: Isothiazolylatropamide; isothiazolylglyoxylamide; isothiazolylphenylacetamide... |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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