Design, synthesis, bioactivity, and structure-activity relationship (SAR) studies of novel benzoylphenylureas containing oxime ether group

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 23, 2008, Pages 11376-11391

  Sun, Ranfeng ^a   Lü, Maoyun ^a   Chen, Li ^a   Li, Qingshan ^a   Song, Haibin ^a   Bi, Fuchun ^a   Huang, Runqiu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Benzoylphenylureas (BPUs); Flucycloxuron; Insect growth regulator; Larvividal activity; Oxime ether; Plant growth regulatory activity

Indexed keywords

CARBANILAMIDE DERIVATIVE; ETHER DERIVATIVE; INSECTICIDE; OXIME;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; LARVA; MOSQUITO; MOTH; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; CULICIDAE; DRUG DESIGN; ETHERS; INSECTICIDES; LARVA; MOLECULAR STRUCTURE; MOTHS; OXIMES; PHENYLUREA COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

HEXAPODA; MYTHIMNA SEPARATA;

EID: 58949089568     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf801901h     Document Type: Article

References (39)

1. Oberlander, H.; Silhacek, D. L. New perspectives on the mode of action of benzoylphenyl urea insecticides. In Insecticides with Novel Modes of Action: Mechanism and Application, 1st ed.; Ishaaya, I., Degheele, D., Eds.; Springer-Verlag: Berlin, Germany, 1998; pp 92-105.
2. Oberlander, H.; Silhacek, D. L. Mode of action of insect growth regulators in Lepidopteran tissue culture. Pestic. Sci. 1998, 54, 300-302.
3. http://www.epa.gov/greenchemistry/pubs/pgcc/winners/dgca00.html.
4. Xu, X. Y.; Qian, X. H.; Li, Z.; Huang, Q. C.; Chen, G. Synthesis and insecticidal activity of new substituted N-aryl-N′- benzoylthiourea compounds. J. Fluorine Chem. 2003, 121, 51-54.
5. Qian, X. H. Quantitative studies on structure-activity relationship of sulfonylurea and benzoylphenylurea type pesticides and their substituents' bioisosterism using synthons' activity contribution. J. Agric. Food Chem. 1999, 47, 4415-4418.
6. Yang, X. L.; Wang, D. Q.; Chen, F. H.; Zhang, Z. N. The synthesis and larvicidal activity of N-aroyl-N′-(5-aryl-2-furoyl)ureas. Pestic. Sci. 1999, 52, 282-286.
7. Li, X. H.; Ling, Y.; Yang, X. L. Synthesis of novel benzoyl ureas containing thiadiazole and their insecticidal activity. Huaxue Tongbao 2003, 66 (5), 333-336.
8. Kubato, S.; Shono, Y.; Matsunaga, T.; Tsunoda, K. Laboratory evaluation of bistrifluron, a benzoylphenylurea compound, as a bait toxicant against Coptotermes formosanus (Isoptera: Rhinotermitidae). J. Econ. Entomol. 2006, 99, 1363-1368.
9. Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Synthesis and bioassay evaluation of 1-(4- substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl) ureas. Bioorg. Med. Chem. 2007, 3678-3683.
10. Yoon, C.; Yang, J. O.; Kang, S. H.; Kim, G. H. Insecticidal properties of bistrifluron against sycamore lace bug, Corythucha ciliata (Hemiptera: Tingidae). J. Pestic. Sci. 2008, 33, 44-50.
11. Brouwer, M. S.; Grosscurt, A. C. Benzoylurea compounds, and pesticidal and pharmaceutical compositionscomprising same. U.S. Patent 4609676, 1986.
12. Lima, L. M. A.; Barreiro, E. J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 2005, 12 (1), 23-49.
13. Sirrenberg, W.; Hamman, I.; Stendel, W.; Klauke, E. Combating arthropods with N-benzoyl-N′-tert-alkoxycarbonylphenyl-(thio) ureas. U.S. Patent 4234600, 1980.
14. Lange, A.; Kiehs, K.; Adophi, H. N-Benzoyl-N′- phenylureas and their use for insect control. U.S. Patent 4599356, 1986.
15. Neubauer, H. J.; Hofmeister, P.; Kuenast, C. (N-Benzoyl- N′-halogenoalkoxycarbonylphenyl)-ureas. DE 3722155, 1989.
16. Brouwer, M. S.; Grosscurt, A. C.; Van Hes, R. Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same. EP 167197, 1986.
17. Nakagawa, Y.; Sotomastu, K.; Irie, K.; Kitahara, K.; Iwamura, H.; Fujita, T. Quantitative structure-activity studies of benzoylphenylurea lavicides III. Effects of substitutes at the benzoyl moiety. Pestic. Biochem. Physiol. 1987, 27, 143-155.
18. Meazza, G.; Rama, F.; Bettarini, F. Synthesis and bioactivity of some fluorine-containing benzoyl arylureas. Part I: Insecticidalacaricidal products in which the aryl group bears a trifluoromethyl-substituted alkyl or alkenyl side chain. Pestic. Sci. 1992, 35, 137.
19. Abbott, W. S. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 1925, 18, 265-267.
20. Mao, C. H.; Wang, Q. H.; 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.
21. Hsu, A. C.; Murphy, R. A.; Aller, H. E.; Hamp, D. W.; Weinstein, B. Insecticidal N′-substituted-N,N′-disubstitutedhydrazines. U.S. Patent 5117057, 1992.
22. 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.
23. Chen, L.; Huang, Z. Q.; Wang, Q. M.; Shang, J.; Huang, R. Q.; Bi, F. C. Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates. J. Agric. Food Chem. 2007, 55, 2659-2663.
24. Liu, Y. X.; Cai, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. Synthesis, crystal structure, and biological activities of 2-cyanoacrylates containing furan or tetrahydrofuran moieties. J. Agric. Food Chem. 2007, 55, 3011-3017.
25. Einhellig, F. A.; Schan, M. K.; Rasmunsen, J. A. Synergistic effects of four cinnamic acid compounds on grain sorghum. Plant Growth Regul. 1983, 1, 251-258.
26. Demuner, A. J.; Barbosa, L. C. A.; Veloso, D. P. New 8-oxabicyclo[3.2.1] oct-6-en-3-one derivatives with plant growth regulatory activity. J. Agric. Food Chem. 1998, 46, 1173-1176.
27. Yang, S. H.; Chang, S. Highly efficient and catalytic conversion of aldoximes to nitriles. Org. Lett. 2001, 3 (26), 4209-4212.
28. West, R. W. Reduction of aromatic nitro-compounds. J. Chem. Soc., Trans. 1925, 127, 494.
29. Edgell, W. F.; Parts, L. Synthesis of alkyl and substituted alkyl fluorides from p-toluenesulfonic acid esters. The preparation of p-toluenesulfonic acid esters of lower alcohols. J. Am. Chem. Soc. 1955, 77, 4899.
30. Yashuhara, A.; Kasano, A.; Sakamoto, T. An efficient method for the deallylation of allyl aryl ethers using electrochemically generated nickel. J. Org. Chem. 1999, 64, 4211-4213.
31. Knudsen, R. D.; Morrice, A. G.; Snyder, H. R. p-Cyanophenol from p-nitrobenzaldoxime by an apparent dehydration-displacement, and a suggested modification of the Miller-Loudon conversion of aldehydes to nitriles. J. Org. Chem. 1975, 40, 2878-2880.
32. Dauvergne, J.; Happe, A. M.; Jadhav, V.; Judtice, D.; Matos, M. C.; McCormack, P. J.; Pitts, M. R.; Roberts, S. M.; Singh, S. K.; Snape, T. J.; Whittall, J. Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4- azacyclopent-2-enones. Tetrahedron 2004, 60, 2559-2567.
33. Krause, J. G. O-Mesitylenesulfonylhydroxylamine. Synthesis 1972, 3, 140.
34. Hiroshi, I.; Keiichi, I. Oxime compounds, their use, and intermediates for their production. WO 9845254, 1998.
35. Deanesly, R. M.; Engs, W. Process for the preparation of substantially pure tertiary olefins. U.S. Patent 2012785, 1992.
36. Bellamy, F. D.; Ou, K. Selective reduction of aromatic nitro compounds with stannous chloride in non acids an non aqueous medium. Tetrahedron Lett. 1984, 25 (8), 839-842.
37. McCaroll, A. J.; Walton, J. C. Photolytic and radical induced decompositions of O-alkyl aldoxime ethers. J. Chem. Soc., Perkin Trans. 2 2000, 1868-1875.
38. Tadić, I. P.; Jakovljević, M. H.; Nešić, S.; Pascual, C.; Simon, W. Protonenresonanzspektren von oximen aromatischer aldehyde. Helv. Chim. Acta 1965, 1157. 48.
39. Bi, F. C.; Chen, L.; Wang, Q. M.; Huang, R. Q. Insecticidal activities of 12 insect growth regulators on oriental armyworms. Pestic. Sci. Admin. 2005, 36 (7), 10-11.