Synthesis and insecticidal activities and SAR studies of novel benzoheterocyclic diacylhydrazine derivatives

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 6, 2009, Pages 2447-2456

  Huang, Zhiqiang ^a   Cui, Quanmin ^b   Xiong, Lixia ^a   Wang, Ziwen ^a   Wang, Kaiyun ^b   Zhao, Qiqi ^a   Bi, Fuchun ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

^b SHANDONG AGRICULTURAL UNIVERSITY   (China)

Author keywords

ANS 118; Benzofuran; Contact toxicity; Diacylhydrazine; Insect growth regulator; Insecticidal activity; JS 118; Stomach toxicity

Indexed keywords

BENZOPYRAN DERIVATIVE; HYDRAZINE DERIVATIVE; INSECTICIDE; N' TERT BUTYL N' (3,5 DIMETHYLBENZOYL) N 5 CHLORO 6 CHROMANECARBOHYDRAZIDE; N'-TERT-BUTYL-N'-(3,5-DIMETHYLBENZOYL)-N-5-CHLORO-6-CHROMANECARBOHYDRAZIDE;

ANIMAL; ARTICLE; CHEMISTRY; LARVA; LEPIDOPTERA; MOSQUITO; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BENZOPYRANS; CULICIDAE; HYDRAZINES; INSECTICIDES; LARVA; LEPIDOPTERA; STRUCTURE-ACTIVITY RELATIONSHIP;

BETA VULGARIS SUBSP. VULGARIS; GOSSYPIUM HIRSUTUM; HELICOVERPA ARMIGERA; HEXAPODA; LEPIDOPTERA; MYTHIMNA SEPARATA; SPODOPTERA EXIGUA;

EID: 64549143773     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8036193     Document Type: Article

References (35)

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)-iV-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, Y.; Li, Y. Q.; Ou, X. M.; Zhang, P. X.; Huang, Z. Q.; Bi, F. C.; Huang, R. Q.; Wang, Q.-M. Synthesis, insecticidal and acaricidal activities of novel 2-aryl-pyrrole derivatives containing ester groups. J. Agric. Food Chem. 2008, 56, 10176-10182.
9. Dhadialla, T. S.; Jansson, R. K. Non-steroidal ecdysone agonists: new tools for IPM and insect resistance management. Peptic. Sci. 1999, 55, 357-359.
10. 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 1. Design of benzoheterocyclic analogues. Pest Manage. Sci. 2003, 59, 25-35.
11. 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.
12. Tetsuya, T.; Yasuhito, K.; Yumiko, Y.; Tetsuo, W.; Mikio, Y.; Yoshihisa, T. Preparation of benzoylhydrazine derivatives as agrochemical insecticides. JP 08231529, 1996.
13. 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. Preparation of diacylhydrazines insecticides and their intermediates. CN 1313276, 2001.
14. 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′-subustitutedbenzoyl-N-5-chloro-6- chroman-ecarbohydrazide derivatives. Bioorg. Med. Chem. 2008, 16, 488-494.
15. Nitin, B. N.; Sagar, R. S.; Tushar, S. P.; Narayan, A. K. Use of urea and its N-substituted tert-butyl derivatives in tert- butylation of aromatic compounds. Chem. Ind. 1983, 7, 206-207.
16. Abbott, W. S. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 1925, 18, 265-267.
17. Mao, C. H.; Wang, Q. M.; Huang, R. Q.; Bi, F. C.; Chen, L.; Liu, Y. X.; Shang, J. Synthesis and insecticidal evaluation of novel N-oxalyl derivatives of tebufenozide. J. Agric. Food Chem. 2004, 52, 6737-6741.
18. Hsu, A. C.; Murphy, R. A.; Aller, H. E.; Hamp, D. W.; Weinstein, B. Insecticidal N′-substituted-N, N′- disubstitutedhydrazines. US 5117057, 1992.
19. Luo, Y. P.; Yang, G. F. Discovery of a new insecticide lead by optimizing a target-diverse scaffold: tetrazolinone derivatives. Bioorg. Med. Chem. 2007, 15, 1716-1724.
20. Zhao, Q. Q.; Shang, J.; Liu, Y. X.; 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. 1. N. alkoxysulfenate derivatives. J. Agric. Food Chem. 2007, 55, 9614-9619.
21. Cui, F.; Tan, Y.; Su, A. F.; Fu, J. C.; Zhu, Q.; Qiao, C. L. Insecticide Resistance and Overproduced Esterases in Populations Culex pipiens Complex of China. Zhongguomeijieshengwuxue ji Kongzhi Zazhi 2005, 16 (6), 413-116.
22. Raymond, M.; Marquine, M. Evolution of insecticide resistance in Culex pipiens polulations: the Corsican paradox. J. Evol. Biol. 1994, 7, 315-337.
23. Chen, L.; Huang, Z. Q.; Wang, Q. M.; Shang, J.; Huang, R. Q.; Bi, F. C. Insecticidal benzoyl phenylurea-s-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates. J, Agric. Food Chem. 2007, 55, 2659-2663.
24. 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.
25. 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.
26. Bandani, A. R.; Butt, T. M. Insecticidal, antifeedant and growth inhibitory activities of efrapeptins, metabolites of the fungus Tolypocladium. Biocontrol. Sci. Technol. 1999, 9, 499-506.
27. Zuo, Y. M.; Wang, K. Y.; Jiang, X. Y. Toxicity of four antibiotic insecticides to different larval stages and to eggs of Plutella xylostella. Nongyao 2004, 43 (1). 25-27.
28. Jiang, X. Y.; Wang, K. Y.; Yi, M. Q. Study on Resistance of Plutella xylostella (L.) in different areas to linsecticides. Nongyaoxue Xuebao 2000, 2 (4), 44-48.
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. Mu, L. Y.; Wang, K. Y.; Liu, F.; Yi, M. Q.; Mu, W.; Zhang, X. A survey on the resistance of cotton bollworm (Heliothis armigera Hübner) to insecticides and a study on the rule of insecticide resistance. Nongyao 1995, 34 (6), 6-9.
31. Wu, Y. D.; Shen, J. L.; You, Z. P. Laboratory selection for fenvalerate resistant and susceptible strains in cotton bollworm, Heliothis armigera (Hübner). Kunchong Xuebao 1994, 37 (2), 129-136.
32. Nevrekar, N. B.; Sawardekar, S. R.; Pandit, T. S.; Kudav, N. A. Use of urea and its N-substituted tert-butyl derivatives in tert- butylation of aromatic compounds. Chem. Ind. 1983, 7, 206-207.
33. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Cesium fluoride-mediated Claisen rearrangement of aryl propargyl ether, exclusive formation of 2-methylarylfuran and its availability as a masked salicylaldehyde. Chem. Pharm. Bull. 1992, 40 (5), 1148-1153.
34. Kunio, T.; Yoshiaki, K.; Akira, I.; Yasuharu, K.; Motomu, H.; Mitsutaka, Y.; Yoshiaki, T.; Tsukasa, S.; Yoshiki, K.; Osamu, C.; Tatsuhiko, K.; Etsuo, N.; Makoto, S. Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5- benzofuranols as a novel series of antiatherogenic antioxidants. J. Med. Chem. 2003, 46, 3083-3093.
35. Patel, G. N.; Trivedi, K. N. Abnormal Claisen rearrangement of 3-prenyloxyxanthone and 3-prenyloxy-4-methylxanthone. J. Indian Chem. Soc. 1988, LXV, 192-193.