Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 1, 2012, Pages 322-330

  Lu, Siyuan ^a   Shao, Xusheng ^a   Li, Zhong ^a   Xu, Zhiping ^a   Zhao, Shishuai ^a   Wu, Yinli ^a   Xu, Xiaoyong ^a  

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

Author keywords

chain opening; cis configuration; neonicotinoids; repellent effects; tetrahydropyridine

Indexed keywords

CHAIN-OPENING; CIS CONFIGURATION; NEONICOTINOIDS; REPELLENT EFFECTS; TETRAHYDROPYRIDINE;

BIOASSAY;

SYNTHESIS (CHEMICAL);

INSECTICIDE; NITRO DERIVATIVE;

ANIMAL; APHID; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; MOTH; SYNTHESIS;

ANIMALS; APHIDS; DRUG DESIGN; INSECTICIDES; MOLECULAR STRUCTURE; MOTHS; NITRO COMPOUNDS;

APHIS CRACCIVORA; MYTHIMNA SEPARATA;

EID: 84862937502     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203068a     Document Type: Article

References (22)

1. Tomizawa, M.; Casida, J. E. Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors Annu. Rev. Entomol. 2003, 48, 339-364 (Pubitemid 37365396)
2. Jeschke, P.; Nauen, R.; Schindler, M.; Elbert, A. Overview of the status and global strategy for neonicotinoids J. Agric. Food Chem. 2011, 59, 2897-2908
3. Matsuda, K.; Shimomura, M.; Ihara, M.; Akamatsu, M.; Sattelle, D. B. Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: electrophysiology, molecular biology, and receptor modeling studies Biosci., Biotechnol., Biochem. 2005, 69, 442-1452
4. Tomizawa, M.; Casida, J. E. Neonicotinoid insecticide toxicology: mechanisms of selective action Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247-268 (Pubitemid 40261805)
5. Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification J. Agric. Food Chem. 2007, 55, 2288-2292 (Pubitemid 46556218)
6. Kagabu, S. Discovery of imidacloprid and further developments from strategic molecular designs J. Agric. Food Chem. 2010, 59, 2887-2896
7. Uneme, H. Chemistry of clothianidin and related compounds J. Agric. Food Chem. 2010, 59, 2932-2937
8. Kiriyama, K.; Itazu, Y.; Kagabu, S.; Nishimura, K. Insecticidal and neuroblocking activities of acetamiprid and related compounds J. Pestic. Sci. 2003, 28, 8-17 (Pubitemid 36614982)
9. Shao, X. S.; Lee, P. W.; Liu, Z. W.; Xu, X. Y.; Li, Z.; Qian, X. H. Cis configuration: a new tactic/rationale for neonicotinoid molecular design J. Agric. Food Chem. 2011, 59, 2943-2949
10. Manjunatha, S. G.; Venodhar Reddy, K.; Rajappa, S. Nitroketene-s,n- acetals as precursors for nitroacetamides and the elusive nitrothioacetahides Tetrahedron Lett. 1990, 31, 1327-1330 (Pubitemid 20075765)
11. Reddy, A. V. N.; Maiti, S. N.; Singh, I. P.; Micetich, R. G. One pot synthesis of 1-substituted 1,2,3,7-tetrahydro-8-nitroimidazol[1,2,6]thiadiazin- 7(1 H)-one 5,5-dioxides Synth. Commun. 1989, 19, 3021-3025
12. Tokumitsu, T. Reaction of β-nitroketeneaminal with olefins bearing electron-withdrawing group and aldehydes Bull. Chem. Soc. Jpn. 1990, 63, 1921-1924
13. Stermitz, F. R.; Larson, K. A.; Kim, D. K. Structural relations among cytotoxic and antitumor benzophenanthridine alkaloid derivatives J. Med. Chem. 1973, 16, 939-940
14. MacKane, J. K.; Anderson, R. Bis(2-chlorothiazol-5-methyl) amine and its salts, and process for working up reaction mixtures comprising 5-aminomethyl-2-chlorothiazole and bis(2-chlorothiazol-5-methyl)amine. U.S. Patent 6403803, 2002.
15. Troschütz, R.; Lückel, A. Nitroketenaminale, 9. mitt.: zur umsetzung von α,β-ungesättigten aldehyden mit nitroketenaminalen Arch. Pharm. 1993, 326, 199-202 (Pubitemid 23141884)
16. Tian, Z. Z.; Jiang, Z. X.; Li, Z.; Song, G. H.; Huang, Q. C. Syntheses and biological activities of octahydro-1 H -cyclopenta[ d ]pyrimidine derivatives J. Agric. Food Chem. 2007, 55, 143-147 (Pubitemid 46059132)
17. Zhang, A.; Kayser, H.; Maienfisch, P.; Casida, J. E. Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3) H ]imidacloprid binding site J. Neurochem. 2000, 75, 1294-1303 (Pubitemid 30660520)
18. Shi, W.; Qian, X. H.; Zhang, R.; Song, G. H. Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles J. Agric. Food Chem. 2001, 49, 124-130 (Pubitemid 32104499)
19. Shao, X. S.; Zhang, W. W.; Peng, Y. Q.; Li, Z.; Tian, Z. Z.; Qian, X. H. cis -Nitromethylene neonicotinoids as new nicotinic family: synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2- α]pyridine Bioorg. Med. Chem. Lett. 2008, 18, 6513-6516
20. Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer Verlag: Dordrecht, The Netherlands, 1999.
21. Shao, X.; Li, Z.; Qian, X.; Xu, X. Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system J. Agric. Food Chem. 2009, 57, 951-957
22. Shao, X.; Fu, H.; Xu, X.; Xu, X.; Liu, Z.; Li, Z.; Qian, X. Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities J. Agric. Food Chem. 2010, 58, 2696-2702