Synthesis and larvicidal properties of some cyclopropylcarboxamides related to cis-permethrin
Taylor, WG; Hall, TW; Vedres, DD
| HERO ID | 3588205 |
|---|---|
| In Press | No |
| Year | 1998 |
| Title | Synthesis and larvicidal properties of some cyclopropylcarboxamides related to cis-permethrin |
| Authors | Taylor, WG; Hall, TW; Vedres, DD |
| Journal | Journal of Agricultural and Food Chemistry |
| Volume | 46 |
| Issue | 4 |
| Page Numbers | 1572-1576 |
| Abstract | Twenty-seven carboxamide derivatives of (+/-)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (permethrin acid) have been synthesized and evaluated in the laboratory against mosquito larvae (Aedes aegypti). These cis-cyclopropylcarboxamides, with N-(substituted)phenyl, N-(substituted)phenylmethyl, N-(substituted)phenylethyl, N-phenylpropyl, and N-phenylbutyl groups, were synthesized from the acid chloride of permethrin acid and various arylamines in methylene chloride. The samples were characterized by C-13 NMR spectroscopy and mass spectrometry. Secondary amides with electron-donating (e.g., methoxy) and electron-withdrawing (e.g., trifluoromethyl) substituents on the phenyl ring as well as nine tertiary amides were investigated. 3-(2,2-Dichloroethenyl)-2,2-dimethyl-N-(3-phenoxyphenyl)methylcyclopropanecarboxamide was the most active experimental compound and was 25 times less potent than (+/-)-cis-permethrin. Cyclopropylcarboxamides of the N-(substituted)phenyl, N-(substituted)phenylethyl, and N-phenylpropyl types were essentially inactive in the larvicidal tests. |
| Wosid | WOS:000073312000065 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | pyrethroid amides; synthesis; purification; spectroscopy; mosquitoes; larvicidal activity |