Imidacloprid and Related Compounds : Structure and Water Solubility of N-Alkyl Derivatives of Imidacloprid
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概要
- 論文の詳細を見る
An intramolecular hydrogen bond between NH…O_2N in insecticide, imidacloprid (1), and its nitromethylene analog 15 was proved by NMR and IR spectra. That electron delocalization over their planar moieties was disrupted by alkylation at the imidazolidine nitrogen atom is demonstrated by the hypsochromic shifts in UV and deshielding effect in NMR spectra. Interestingly, the N-alkyl derivatives (C1-5) had greater water solubility than 1,although increasing alkyl chain length decreased the solubility. The hydrophilicity of the alkyl derivatives would result from remote charge heads being formed as a result of the conjugation disruption by alkylation, while the hydrophobicity of 1 could be ascribed to the charge distribution over the conjugated system coupled with the intramolecular H-bonding. The greater water solubility of 15 than 1 and contrastively small solubility of the cyanoimine analogue are discussed based on the difference in their steric crowding.
- 社団法人日本農芸化学会の論文
- 1998-06-23
著者
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Tanaka Masahiro
Department of Fixed Prosthodontics and Occlusion, Osaka Dental University
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YOKOYAMA Kazuhito
Department of Epidemiology and Environmental Health, Juntendo University School of Medicine
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Tanaka Masahiro
Department Of Applied Chemistry
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Tanaka Masahiro
Department Of Chemistry Faculty Of Education Gifu University
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KAGABU Shinzo
Department of CHemistry, Faculty of Education, Gifu University
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Kagabu Shinzo
Department Of Chemistry Faculty Of Education Gifu University
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IWAYA Kazuko
Department of Chemistry, Faculty of Education, Gifu University
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Iwaya Kazuko
Department Of Chemistry Faculty Of Education Gifu University
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Yokoyama Kazuhito
Department Of Chemistry Faculty Of Education Gifu University
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Tanaka Masahiro
Department Fixed Prosthodontics And Occlusion Osaka Dental University
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