Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part

Autor:	Naoko Yasui, Eiichi Yamada, Kenji Kodaka, Nobuyuki Kawahara, Katsutoshi Kinoshita, Takeo Wakita
Rok vydání:	2004
Předmět:	chemistry.chemical_compound Nitroguanidine chemistry Stereochemistry Health Toxicology and Mutagenesis Insect Science Neonicotinoid Moiety Nephotettix cincticeps Guanidine Dinotefuran
Zdroj:	Journal of Pesticide Science. 29:348-355
ISSN:	1349-0923 1348-589X
DOI:	10.1584/jpestics.29.348
Popis:	Dinotefuran ((RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine) is a new neonicotinoid which has a characteristic (±)-tetrahydro-3-furylmethyl moiety instead of the pyridine-like moiety of other neonicotinoids. A series of dinotefuran derivatives were synthesized and tested against hemiptera. SAR (structure-activity relationships) of the nitroguanidine part of dinotefuran are summarized as follows: (1) the mono-methyl group as a N-substituent gave the best activity for the acyclic nitroimino and nitromethylene compounds, (2) the acyclic compounds showed the same activity as the cyclic compounds against Nephotettix cincticeps and were superior to them against Laodelphax striatellus, (3) N-acylation of this series scarcely changed the level of activity. On the basis of these results, we selected dinotefuran for development. © Pesticide Science Society of Japan
Databáze:	OpenAIRE
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