Syntheses and biological activities of octahydro-1H-cyclopenta[d]pyrimidine derivatives

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 1, 2007, Pages 143-147

  Tian, Zhongzhen ^a   Jiang, Zhaoxing ^a   Li, Zhong ^a   Song, Gonghua ^a   Huang, Qingchun ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Biological activity; Hydrophobicity; Nitromethylene derivatives; Regioselective; Synthesis

Indexed keywords

AMINE; FORMALDEHYDE; INSECTICIDE; PYRIMIDINE DERIVATIVE;

ANIMAL; APHID; ARTICLE; CHEMISTRY; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINES; ANIMALS; APHIDS; FORMALDEHYDE; HYDROPHOBICITY; INSECTICIDES; MAGNETIC RESONANCE SPECTROSCOPY; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

APHIS CRACCIVORA;

EID: 33846061236     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf062845l     Document Type: Article

References (16)

1. Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K.; Kagabu, S. 1-(6-Chloronicotinyl)-2-nitroiminoimidazolidines and related compounds as potential new insecticides. Biosci. Biotechnol. Biochem. 1992, 56, 364-365.
2. Bai, D.; Lummis, S. C. R.; Leicht, W.; Breer, H.; Sattelle, D. B. Actions of Imidacloprid and a Related Nitromethylene on Cholinergic Receptors of an Identified Insect Motor Neurone. Pestic. Sci. 1991, 33, 197-204.
3. 3H] Imidacloprid in the Insect Acetylcholine Receptor. Pestic. Biochem. Physiol. 1993, 46, 40-46.
4. Nishimura, K.; Kanda, Y.; Okazawa, A.; Ueno, T. Relationship Between Insecticidal and Neurophysiological Activities of Imidacloprid and Related Compounds. Pestic. Biochem. Physiol. 1994, 50, 51-59.
5. Mori, K.; Okumoto, T.; Kawahara, N.; Ozoe, Y. Interaction of Dinotefuran and Its Analogues with Nicotinic Acetylcholine Receptors of Cockroach Nerve Cords. Pest Manage. Sci. 2001, 58, 190-196.
6. Zhang, N.; Tomizawa, M.; Casida, J. E. α-Nitro Ketone as an Electrophile and Nucleophile: Synthesis of 3-Substituted 2- Nitromethylenetetrahydrothiophene and tetrahydrofuran as Drosophila Nicotinic Receptor Probes. J. Org. Chem. 2004, 69, 876-881.
7. Markley, L. D.; Sparks, T. C.; Dripps, J. E.; Gifford, J. M.; Schoonover, J. R.; Neese, P. A.; Dintenfass, L. P.; Karr, L. L.; Benko, Z. L.; Amicis, C. V.; Erickson, W. R.; Samaritoni, J. G.; Demeter, D. A.; Watson, G. B.; Rau, C. L. Preparation of novel heterocyclic nitroalkenes as potential acaricides and insecticides and processes for using and making them. PCT. Int. Appl. WO2002018339, 2002.
8. Samaritoni, J. G.; Demeter, D. A.; Gifford, J. M.; Watson, G. B.; Kempe, M. S.; Bruce, T. J. Dihydropiperazine Neonicotinoid Compounds. Synthesis and Insecticidal Activity. J. Agric. Food. Chem. 2003, 51, 3035-3042.
9. Kagabu, S.; Nishiwaki, H.; Sato, K.; Hibi, M.; Yamaoka, N.; Nakagawa, Y. Nicotinic Acetylcholine Receptor Binding of Imidacloprid-related Diaza Compounds with Various Ring Sizes and Their Insecticidal Activity against Musca Domestica. Pest Manage. Sci. 2002, 58, 483-490.
10. Yamamoto, I. Nicotine to Nicotinoids: 1962 to 1997, in Nicotinoid insecticides and the nicotinic acetylcholine receptor; Yamamoto, I., Casida, J. E., Eds.; Springer-Verlag: Tokyo, 1999; pp 3-27.
11. Yamamoto, I.; Tomizawa, M.; Satio, T.; Miyamoto, T.; Walcott, E. C.; Sumikawa, W. Structural factors contributing to insecticidal and selective actions of neonicotinoids. Arch. Insect. Biochem. Physiol. 1998, 37, 24-32.
12. Tomizawa, M.; Yamamoto, I. Binding of nicotinoids and the related compounds to the insect nicotinic acetylcholine receptor. J. Pestic. Sci. 1993, 18, 91-98.
13. Schroeder, H. E.; Rigby, G. W. The Cyclization of Acetylated p-Iminonitriles: 4-Amino-2-hydroxy-6,7-dihydropyridine. J. Am. Chem. Soc. 1949, 71, 2205-2209.
14. FAO. Recommended methods for the detection and measurement of resistance of agricultural pests to pesticides: method for adult aphids-FAO method No 17. FAO. Plant. Protect. Bull. 1979, 18, 6-9.
15. Obase, H.; Nakamizo, N.; Takai, H.; Teranishi, M. Synthesis of 3-(4-Piperidylidene)-1,3-dihydro-2H-indol-2-one Derivatives. Bull. Chem. Soc. Jpn. 1983, 56, 2853-2854.
16. Kollmeyer, W. D.; Flattum, R. F.; Foster, J. P.; Poewll, J. E.; Schroeder, M. E.; Soloway, S. B. Discovery of the nitromethylene hetercycle insecticides. In Nicotinoid insecticides and the nicotinic acetylcholine receptor, Yamamoto, I., Casida, J. E., Eds.; Springer-Verlag, Tokyo, 1999; pp 71-89.