Nuclear Magnetic Resonance Spectra and Mosquito Repellent Properties of Some Oxazolidine Derivatives of 5-Methyl-4-Hexenal

Taylor, Wesley G.; Schreck, C. E.

doi:10.1002/jps.2600780207

Cited by 4 publications

(1 citation statement)

References 11 publications

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“…Chemical ionization mass spectra (CI-MS) with isobutane as the reagent gas were obtained on a Hewlett-Packard 5985B mass spectrometer equipped with 30 m capillary columns of DB-5 (J & W Scientific, Folsom, CA) or SPB-1 (Supelco Inc., Bellefonte, PA). 1 H (400.1 MHz) and 13 C (100.6 MHz) NMR spectra as well as DEPT and XHDEPT experiments were acquired as previously described (Taylor and Schreck, 1989) on a Bruker AM-400 spectrometer. Chemical shifts are reported relative to internal tetramethylsilane (TMS; 0 ppm).…”

Section: Generalmentioning

confidence: 99%

Synthesis and Larvicidal Properties of Some Cyclopropylcarboxamides Related tocis-Permethrin

Taylor

Hall

Vedres

1998

J. Agric. Food Chem.

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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 13C 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. Keywords: Pyrethroid amides; synthesis; purification; spectroscopy; mosquitoes; larvicidal activity

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Section: Generalmentioning

confidence: 99%

Synthesis and Larvicidal Properties of Some Cyclopropylcarboxamides Related tocis-Permethrin

Taylor

Hall

Vedres

1998

J. Agric. Food Chem.

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Synthesis and Mosquito Repellent Properties of 2,2-Dialkyl- and 2-Alkyl-4,4-dimethyl-N-acetyloxazolidines

1996

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Nineteen novel N-acetyl-2,2-dialkyloxazolidines (2) and N-acetyl-2-alkyl-4,4-dimethyloxazolidines (3) were synthesized from commercially available carbonyl compounds and ethanolamine or 2-amino-2-methyl-I-propanol. Their bioactivity against laboratory-reared mosquitoes was compared in patch tests to known N-acetyl-2-alkyloxazolidines (1) and N,N-diethyl-m-toluamide (deet insect repellent). Isomeric composition measurements by ["ClNMR spectroscopy favoured the Z rotational isomer for samples of 2 (91-96% Z) and the E rotational isomer for samples of 3 (66-71% E), in agreement with molecular mechanics calculations on rotational isomers of model oxazolidines. Samples of 1 were previously shown to exist in solution mostly as the Z isomer (60-70% Z). Within the optimal molecular weight range for these experimental chemicals, the duration of repellency against Aedes aegypti (L.), Anopheles quadrimaculatus Say and Anopheles albimanus Wiedemann generally followed the order: 1 > 2 > deet > 3. Bioassay data are discussed in relation to the equilibrium populations of rotational isomers for substituted N-acetyloxazolidines.

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Synthesis and mosquito repellent properties of some 2‐alkyl‐N‐acetyloxazolidines

Taylor

Schreck

1991

Pestic. Sci.

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Twenty 2,3-disubstituted oxazolidines, mostly with an alkyl group at C-2 and an acetyl group at N-3 have been synthesized and evaluated in the laboratory as mosquito repellents. Repellent activity was assessed in two bioassays with three mosquito species, using a human arm as bait. In patch tests, oxazolidines with an n-hexyl, n-heptyl or n-octyl group showed better activity than those with shorter or longer side chains. In stocking tests, prolonged repellency of selected oxazolidines was evident against Anopheles quadrimaculatus. Some of these experimental chemicals, for example N-acetyl-2-octyl oxazolidine, warrant further investigations as potentially useful insect repellents.

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Nuclear Magnetic Resonance Spectra and Mosquito Repellent Properties of Some Oxazolidine Derivatives of 5-Methyl-4-Hexenal

Cited by 4 publications

References 11 publications

Synthesis and Larvicidal Properties of Some Cyclopropylcarboxamides Related tocis-Permethrin

Synthesis and Larvicidal Properties of Some Cyclopropylcarboxamides Related tocis-Permethrin

Synthesis and Mosquito Repellent Properties of 2,2-Dialkyl- and 2-Alkyl-4,4-dimethyl-N-acetyloxazolidines

Synthesis and mosquito repellent properties of some 2‐alkyl‐N‐acetyloxazolidines

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