Chemistry of polyhalogenated nitrobutadienes, 8: Nitropolychlorobutadienes--precursors for insecticidal neonicotinoids.
Nitropolychlorobutadienes are valuable precursors for highly functionalized acyclic or (hetero)cyclic compounds. In this 8th part of our synthetically oriented series we focus on the application of these versatile starting materials in the synthesis of analogs of the heterocyclic insecticides imidacloprid and thiacloprid, and the acyclic counterpart clothianidin. In addition to the main synthetic part, leading to imidazolidines or oxazolidines, further promising types of compounds derived by subsequent chemical modifications, are introduced. Most of the new compounds show high insecticidal activity.
Zapol'skii
Viktor A
VA
Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany.
Fischer
Reiner
R
Namyslo
Jan C
JC
Kaufmann
Dieter E
DE
D002070:Butadienes / Q000138:chemical synthesis / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D048289:Imidazolidines / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry*; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry; D013843:Thiazines / Q000138:chemical synthesis / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
D002070:Butadienes; D006146:Guanidines; D007093:Imidazoles; D048289:Imidazolidines; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; D010080:Oxazoles; D011725:Pyridines; D013843:Thiazines; D013844:Thiazoles; C064210:oxazolidine; C480342:clothianidin; C082359:imidacloprid; C417209:thiacloprid