Synthesis, crystal structures, insecticidal activities, and structure-activity relationships of novel N ′- Tert -Butyl- N ′-substituted-benzoyl- N -[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1, 3]([1,4])dioxine}carbohydrazide derivatives

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 2, 2011, Pages 635-644

  Huang, Zhiqiang ^a   Liu, Yuxiu ^a   Li, Yongqiang ^a   Xiong, Lixia ^a   Cui, Zhipeng ^a   Song, Hongjian ^a   Liu, Hongli ^a   Zhao, Qiqi ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Benzofuran; benzoheterocycle; crystal structure; diacylhydrazine; insect growth regulator; insecticidal activity; SAR

Indexed keywords

BENZOFURANS; BENZOHETEROCYCLE; DIACYLHYDRAZINE; INSECT GROWTH REGULATOR; INSECTICIDAL ACTIVITY; SAR;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OCEAN HABITATS; RHODIUM COMPOUNDS;

CRYSTAL STRUCTURE;

CARBOHYDRAZIDE; HYDRAZINE DERIVATIVE; INSECTICIDE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; INSECT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; HYDRAZINES; INSECTICIDES; INSECTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

HEXAPODA; LEPIDOPTERA; MYTHIMNA SEPARATA; SPODOPTERA EXIGUA; ZEA MAYS;

EID: 78751534388     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104196t     Document Type: Article

References (34)

1. Wing, K. D. RH-5849, a nonsteroidal ecdysone agonist: effects on a Drosophila cell line Science (Washington, DC) 1988, 241, 467-469
2. Wing, K. D.; Slawecki, R. A.; Carlson, G. R. RH-5849, a nonsteroidal ecdysone agonist effects on Lepidoptera Science (Washington, DC) 1988, 241, 470-472
3. Qian, X. H. Molecular modeling study on the structure-activity relationship of substituted dibenzoyl-1- tert -butylhydrazines and their structural similarity to 20-hydroxyecdysone J. Agric. Food Chem. 1996, 44, 1538-1542
4. Cao, S.; Qian, X. H.; Song, G. H. N ′- tert -Butyl- N ′-aroyl- N -(alkoxycarbonylmethyl)- N -aroylhydrazines, a novel nonsteroidal ecdysone agonist: syntheses, insecticidal activity, conformational, and crystal structure analysis Can. J. Chem. 2001, 79, 272-278
5. Zhao, P. L.; Li, J.; Yang, G. F. Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines Bioorg. Med. Chem. 2007, 15, 1888-1895
6. Cui, Z. N.; Huang, J.; Li, Y.; Ling, Y.; Yang, X. L.; Chen, F. H. Synthesis and bioactivity of novel N, N ′-diacylhydrazine derivatives containing furan (I) Chin. J. Chem. 2008, 26 (5) 916-922
7. Cui, Z. N.; Wang, Z.; Li, Y.; Zhou, X. Y.; Ling, Y.; Yang, X. L. Synthesis and insecticidal activity of diacylhydrazine containing furan Chin. J. Org. Chem. 2007, 27 (10) 1300-1304
8. Zhao, Q. Q.; Shang, J.; Huang, Z. Q.; Wang, K. Y.; Bi, F. C.; Huang, R. Q.; Wang, Q. M. Synthesis and insecticidal activities of novel N -Sulfenyl- N ′- tert -butyl- N, N ′-diacylhydrazines. 2. N -Subsituted phenoxysulfenate derivatives J. Agric. Food Chem. 2008, 56, 5254-5259
9. Dhadialla, T. S.; Jansson, R. K. Non-steroidal ecdysone agonists: new tools for IPM and insect resistance management Pestic. Sci. 1999, 55, 357-359
10. Smagghe, G.; Carton, B.; Wesemael, W.; Ishaaya, I.; Tirry, L. Ecdysone agonist mechanism and application on Spodoptera species Pestic. Sci. 1999, 55, 343-389
11. Sundaram, M.; Palli, S. R; Ishaaya, I.; Krell, P. J.; Retnakaran, A. Toxicity of ecdysone agonists correlates with the induction of CHR3 mRNA in the spruce budworm Pestic. Biochem. Physiol. 1998, 62, 201-208
12. Trisyono, A.; Chippendale, C. M. Effect of the nonsteroidal ecdysone agonists, methoxyfenozide and tebufenozide, on the European corn borer (Lepidoptera: Pyralidae) J. Econ. Entomol. 1997, 90, 1486-1492
13. Haga, T.; Toki, T.; Koyanagi, T.; Omastsu, M.; Yamamoto, K.; Morita, M. Hydrazine-based compound, production thereof and controlling agent against noxious animal containing the same. JP03141245, 1991.
14. Totani, T.; Kato, Y.; Yajima, Y.; Watabe, T.; Yanagi, M. New hydrazine derivative and insecticidal compositon containing the same derivative as active ingredient. JP04235177, 1992.
15. Kobayashi, T.; Totani, T.; Sato, H.; Asahina, K.; Yanagi, M. Preparation of benzodioxolane derivatives as insecticides. JP04178380, 1992.
16. Yanai, T.; Tsukamoto, Y.; Sawada, Y.; Yokoi, S.; Yanagi, M.; Totani, T.; Masui, A.; Watabe, T. Preparation of N, N ′-dibenzoyl- N -formylhydrazine derivatives as insecticides. JP06247920, 1994.
17. Totani, T.; Kato, Y.; Yamamoto, Y.; Watabe, T.; Yanagi, M.; Tsukamoto, Y. Preparation of benzoylhydrazine derivatives as agrochemical insecticides. JP08231528, 1996.
18. Totani, T.; Kato, Y.; Yamamoto, Y.; Watabe, T.; Yanagi, M.; Tsukamoto, Y. Preparation of N -benzofurancarbonyl- N ′-benzoylhydrazine derivatives as insecticides. JP08231529, 1996.
19. Yoshihiro, S.; Toshiaki, Y.; Harumi, N.; Yoshihisa, T.; Shinji, Y.; Mikio, Y.; Tetsuya, T.; Hiroyasu, S.; Yasuhito, K.; Hidetoshi, S.; Tetsuo, W.; Yoshimi, Y.; Seiichirou, K.; Akio, M. Synthesis and insecticidal activity of benzoheterocyclic analogues of N ′-benzoyl- N -(tert -butyl) benzohydrazide: Part 1. Design of benzoheterocyclic analogues Pest Manag. Sci. 2002, 59, 25-35
20. Zhang, X. N.; Li, Y. F.; Zhu, L. M.; Liu, L. Y.; Sha, X. Y.; Xu, H.; Ma, H. J.; Wang, F. Y.; Ni, Y. P.; Guo, L. P. Prepatation of diacylhydrazines insecticides and their intermediates. CN 1313276, 2001.
21. Xu, N. F.; Zhang, Y.; Zhang, X. N.; Ni, J. P.; Xiong, J. M.; Shen, M. Manufacture of JS118 insecticide suspension agent. CN 1918986, 2007.
22. Sawada, Y.; Yanai, T.; Nakagawa, H.; Tsukamoto, Y.; Yokoi, S.; Yanagi, M.; Toya, T.; Sugizaki, H.; Kato, Y.; Shirakura, H.; Watanabe, T.; YaJima, Y.; Kodama, S.; Masui, A. Synthesis and insecticidal activity of benzoheterocyclic analogues of N ′-benzoyl- N -(tert -butyl)benzohydrazide: Part 2. Introduction of substituents on the benzene rings of the benzoheterocycle moiety Pest Manage. Sci. 2003, 59, 36-48
23. Huang, Z. Q.; Song, H. J.; Cui, Z. P.; Zhou, Z. Q.; Wang, Q. M. Design, synthesis and crystal structure of novel N ′- tert -butyl- N ′-(substitutedbenzoyl)- N -(chromane-5-carbonyl)hydrazine derivatives Chin. J. Org. Chem. 2009, 29 (6) 891-897
24. Tsutomu, I.; Keiko, N.; Naoko, O.; Hisashi, I. Cesium fluoride-mediated Claisen rearrangements of phenyl propargyl ethers: effect of a substituent on the phenyl ring on the rearrangement Heterocycles 1994, 39 (1) 371-380
25. Aristegui, S. R.; El-Murr, M. D.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R. Judicious application of allyl protecting groups for the synthesis of 2-morpholin-4-yl-4-oxo-4 H -chromen-8-yl triflate, a key precursor of DNA-dependent protein kinase inhibitors Org. Lett. 2006, 8 (26) 5927-5929
26. Govindachari, T. R.; Nagarajan, K.; Rajadurai, S.; Ramadas, R. U. Synthesis of 3,4-dimethoxy-6,7-methylenedioxyaporphine Chem. Ber. 1958, 91, 36-39
27. Mitscher, L. A.; Flynn, D. L.; Gracey, H. E.; Drake, S. D. Quinolone antimicrobial agents. 2. Methylenedioxy positional isomers of oxolinic acid J. Med. Chem. 1979, 22 (11) 1354-1357
28. Fuson, R. C.; Gaertner, R.; Chadwick, D. H. Replacement of nuclear alkoxy groups by the action of Grignard reagents J. Org. Chem. 1948, 13, 489-495
29. Wu, Y. D.; Shen, J. L.; Chen, J.; Lin, X. W.; Li, A. M. Evaluation of two resistance monitoring methods in Helicoverpa armigera: topical application method and leaf dipping method Zhiwu Baohu 1996, 22 (5) 3-6
30. Ma, H.; Wang, K. Y.; Xia, X. M.; Zhang, Y.; Guo, Q. L. The toxicity testing of five insecticides to different instar larvae of Spodoptera exigua Xiandai Nongyao 2006, 5, 44-46
31. Busivine, J. R. Recommended Methods for Measurement of Pest Resistance to Pesticides; FAO Plant Production and Protection Paper 21; FAO: Rome, Italy, 1980; pp 3 - 13 and 119 - 122.
32. Mao, C. H.; Wang, K. L.; Wang, Z. W.; Ou, X. M.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Synthesis and insecticidal evaluation of novel N′ -tert-butyl- N ′-subustituted benzoyl- N -5-chloro-6-chromane carbohydrazide derivatives Bioorg. Med. Chem. 2008, 16, 488-494
33. Robert, E. H.; Philadelphia, P. Insecticidal N, N′ -disubstitutued- N, N′ -diacylhydrazines. U.S. Patent 5482962, 1996.
34. Wheelock, C. E.; Nakagawa, Y.; Harada, T.; Oikawa, N.; Akamatsu, M.; Smagghe, G.; Stefanou, D.; Iatrou, K.; Swevers, L. High-throughput screening of ecdysone agonists using a reporter gene assay followed by 3-D QSAR analysis of the molting hormonal activity Bioorg. Med. Chem. 2006, 14 (4) 1143-1159