Pyrrole- and Dihydropyrrole-Fused Neonicotinoids: Design, Synthesis, and Insecticidal Evaluation

• Published in: Journal of agricultural and food chemistry Vol. 61; no. 2; pp. 312 - 319
• Main Authors: Ye, Zhenjun, Shi, Lina, Shao, Xusheng, Xu, Xiaoyong, Xu, Zhiping, Li, Zhong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.01.2013; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; aluminum chloride; Anabasine - analogs & derivatives; Anabasine - chemical synthesis; Anabasine - chemistry; Animals; Aphids; Aphis craccivora; Biological and medical sciences; Chemistry; Chemistry, Applied; Drug Design; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; insecticidal properties; Insecticides - chemical synthesis; Insecticides - chemistry; Lethal Dose 50; Life Sciences & Biomedicine; mass spectrometry; Molecular Structure; neonicotinoid insecticides; nuclear magnetic resonance spectroscopy; Physical Sciences; Pyrroles - chemical synthesis; Pyrroles - chemistry; Science & Technology; Structure-Activity Relationship; neonicotinoid; dihydropyrrole; nAChR; Pyrrole; AZA-ENE; NICOTINIC ACETYLCHOLINE-RECEPTOR; CHEMISTRY; HETEROCYCLIC KETENE AMINALS; NITROMETHYLENE NEONICOTINOIDS; DERIVATIVES; Design; Evaluation; Neonicotinoid; Insecticide; Synthesis; Pesticides
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf3044132

Versatile pyrrole- and dihydropyrrole-fused neonicotinoids were obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum chloride (AlCl3) exhibited high catalytic selectivity for the synthesis of the titled etherified compounds at room temperature and the eliminated products under reflux conditions. The target molecules have been identified on the basis of satisfactory analytical and spectral [1H and 13C nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and X-ray] data. All synthesized compounds have been screened for insecticidal activity. The preliminary insecticidal activity results showed that some of the aimed compounds displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).