Novel Anthranilic Diamide Insecticides: Design, Synthesis, and Insecticidal Evaluation
Xuewen Hua A B , Wutao Mao B C , Zhijin Fan A B E , Xiaotian Ji A B , Fengyun Li A B , Guangning Zong A B , Haibin Song A , Juanjuan Li A B , Like Zhou A B , Lifeng Zhou D , Xiaowen Liang D , Genhao Wang D and Xiaoyan Chen DA State Key Laboratory of Elemento-Organic Chemistry, Nankai University, No. 94, Weijin Road, Nankai District, Tianjin 300071, P. R. China.
B Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. China.
C College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Henan 473061, P. R. China.
D Jiangxi Tianren Ecological Co. Ltd, No. 181 Junshan Dadao, Jian, Jiangxi 343100, P. R. China.
E Corresponding author. Email: fanzj@nankai.edu.cn
Australian Journal of Chemistry 67(10) 1491-1503 https://doi.org/10.1071/CH13701
Submitted: 23 October 2013 Accepted: 22 February 2014 Published: 10 April 2014
Abstract
Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1H and 13C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of compound N-(2-(2-methyl-2-(methylthio)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 16e. Bioassay results indicated that most of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the positive control cyantraniliprole. In particular, N-(2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100 % at a concentration of 1 µg mL–1. These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.
References
[1] M. Fill, J. A. Copello, Physiol. Rev. 2002, 82, 893.| 1:CAS:528:DC%2BD38Xot1Ggurk%3D&md5=23fee6dbf6dc42b1207724e862725c2bCAS | 12270947PubMed |
[2] L. Zhu, X. W. Zhong, S. R. Wayne Chen, N. Banavali, Z. Liu, J. Biol. Chem. 2013, 288, 903.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXos1ahtQ%3D%3D&md5=6785e2f970b31cb80a965b9530d7198fCAS | 23204524PubMed |
[3] S. L. Hamilton, Cell Calcium 2005, 38, 253.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpvV2lsrY%3D&md5=0afa4d8f6d636ec9615cdbde628516bbCAS | 16115682PubMed |
[4] L. Kimlicka, F. Petegem, Sci. China C Life Sci. 2011, 54, 712.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptlyjtb8%3D&md5=ff96c192d17c35a7006916d92619c8ddCAS |
[5] A. F. Dulhunty, Clin. Exp. Pharmacol. Physiol. 2006, 33, 763.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xps1Sntbw%3D&md5=e23cadc1f378d64bd2c7f7d3952022c6CAS | 16922804PubMed |
[6] G. P. Lahm, D. Cordova, J. D. Barry, Bioorg. Med. Chem. 2009, 17, 4127.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXntVGjtLc%3D&md5=7e21b2e84c142881a6643b0115859316CAS | 19186058PubMed |
[7] K. A. Hughes, G. P. Lahm, T. P. Selby, T. M. Stevenson, W. O. Patent 2004067528 A1 2004.
[8] G. P. Lahm, T. P. Selby, T. M. Stevenson, W. O. Patent 2003015519 A1 2003.
[9] M. S. Tohnishi, H. K. Nakao, E. H. Kohno, T. T. Nishida, T. I. Furuya, T. K. Shimizu, A. H. Seo, K. K. Sakata, S. K. Fujioka, H. I. Kanno, E. P. Patent 1006107 2010.
[10] B. S. Chai, X. M. He, J. F. Wang, Z. N. Li, C. L. Liu, Agrochemicals 2010, 49, 167.[In Chinese]
| 1:CAS:528:DC%2BC3cXptFCmtr8%3D&md5=1a24d077a48dedc7cf932dc050fa2537CAS |
[11] S. Tiwari, L. L. Stelinski, Pest Manag. Sci. 2013, 69, 1066.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVGhu74%3D&md5=83207242f6af2ec2ff70323b60588a24CAS | 23371893PubMed |
[12] L. A. Teixeira, J. T. Andaloro, Pestic. Biochem. Physiol. 2013, 106, 76.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjvFCguro%3D&md5=491b4c53956a980f9638cbec8735f0c7CAS |
[13] D. B. Sattelle, D. Cordova, T. R. Cheek, Invert. Neurosci. 2008, 8, 107.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVSgt7nF&md5=75493dc2266e829ab62da9f970bce030CAS | 18696132PubMed |
[14] Y. M. Zhu, X. P. Huang, R. Rogers, M. R. Loso, G. Whiteker, J. Daeuble, B. Nugent, In Proceedings of the 242nd ACS National Meeting & Exposition, Denver, CO, USA, 28 August–1 September 2011. 2011; ORGN-326 (American Chemical Society, Washington, D. C.).
[15] C. Longhurst, J. M. Babcock, I. Denholm, K. Gorman, J. D. Thomas, T. C. Sparks, Pest Manag. Sci. 2013, 69, 809.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslCktLfP&md5=7081dc2aac5a1a56daa177e361b7b288CAS | 23203347PubMed |
[16] T. C. Sparks, M. R. Loso, G. B. Watson, J. M. Babcock, V. J. Kramer, Y. M. Zhu, B. M. Nugent, J. D. Thomas, in Modern Crop Protection Compounds, 2nd edn (Eds W. Kraemer, U. Schirmer, P. Jeschke) 2012, Vol. 3, pp. 1226–1237 (VCH Verlagsgesellschaft: Weinheim).
[17] J. M. Babcock, C. B. Gerwick, J. X. Huang, M. R. Loso, G. Nakamura, S. P. Nolting, R. B. Rogers, T. C. Sparks, J. Thomas, G. B. Watson, Pest Manag. Sci. 2011, 67, 328.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1yltbg%3D&md5=075e5814ccad7688faf1a05d1267c2beCAS | 21308958PubMed |
[18] R. J. Rasoulpour, J. Reza, R. G. Ellis-Hutchings, C. Terry, N. S. Millar, C. L. Zablotny, A. Gibb, V. Marshall, T. Collins, E. W. Carney, R. Billington, Toxicol. Sci. 2012, 127, 522.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xnt12ksr4%3D&md5=b49a5ab56d946e91fe17c95aadc1c67aCAS | 22461452PubMed |
[19] Y. M. Zhu, M. R. Loso, G. B. Watson, T. C. Sparks, R. B. Rogers, J. X. Huang, B. C. Gerwick, J. M. Babcock, D. Kelley, V. B. Hegde, B. M. Nugent, J. M. Renga, J. Agric. Food Chem. 2011, 59, 2950.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVOktrzJ&md5=dcfdffbf994eff9ac85711bd140d146cCAS |
[20] T. C. Sparks, G. B. Watson, M. R. Michael, C. X. Geng, J. M. Babcock, J. D. Thomas, Pestic. Biochem. Physiol. 2013, 107, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVCgt7vE&md5=c21b0133d6f23493dcdefada78129278CAS |
[21] P. Cutler, R. Slater, A. J. F. Edmunds, P. Maienfisch, R. G. Hall, F. G. P. Earley, T. Pitterna, S. Pal, V. L. Paul, J. Goodchild, Pest Manag. Sci. 2013, 69, 607.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFynurbI&md5=1e4021cf79d38b9677ab3a928162cf67CAS | 23112103PubMed |
[22] C. Gnamm, A. Jeanguenat, A. C. Dutton, C. Grimm, D. P. Kloer, A. J. Crossthwaite, Bioorg. Med. Chem. Lett. 2012, 22, 3800.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XmtlWhurw%3D&md5=3091c5d2422ae125a4afdcf7927de11cCAS | 22552196PubMed |
[23] H. Blaschke, S. Pazenok, W. O. Patent 2007022901 A1 2007.
[24] J. H. Choi, M. H. Kim, S. H. Kim, C. H. Park, B. Y. Joe, K. Chun, B. K. Oh, D. Ryu, R. Won, J. S. Park, K. H. Kim, H. C. Lee, W. O. Patent 2009061131 A2 2009.
[25] Z. J. Ye, L. N. Shi, X. S. Shao, X. Y. Xu, Z. P. Xu, Z. Li, J. Agric. Food Chem. 2013, 61, 312.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVKmsb%2FF&md5=c9c2830fbfa0c67aea743fff49808a3bCAS |
[26] F. F. Jian, H. L. Xiao, P. S. Zhao, Chinese J. Struct. Chem. 2004, 23, 486.
| 1:CAS:528:DC%2BD2cXks1GhsLY%3D&md5=9ed8df4d5bfbadc2abc92f14df34e9faCAS |
[27] J. F. Zhang, J. Y. Xu, B. L. Wang, Y. X. Li, L. X. Xiong, Y. Q. Li, Y. Ma, Z. M. Li, J. Agric. Food Chem. 2012, 60, 7565.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVGhsrfK&md5=4256cd670c09f6677df6ae9817185ac8CAS | 22812664PubMed |
[28] K. A. Hughes, G. P. Lahm, T. P. Selby, W. O. Patent 2004046129 A2 2004.
[29] G. P. Lahm, T. P. Selby, W. O. Patent 2005118552 A2 2005.
[30] P. J. Montoya-Pelaez, Y.-S. Uh, C. Lata, M. P. Thompson, R. P. Lemieux, C. M. Crudden, J. Org. Chem. 2006, 71, 5921.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XmvFaqt7Y%3D&md5=2baae3649f98188e78423ff2e9dc7e7fCAS | 16872173PubMed |
[31] M. R. Loso, B. M. Nugent, R. B. Rogers, Y. M. Zhu, J. M. Renga, V. B. Hegde, J. J. Demark, W. O. Patent 2007095229 A2 2007.
[32] SHELXTL ver. 5.0 (Ed G. M. Sheldrick) 2001 (University of Göttingen: Göttingen, Germany).
[33] H. Xu, J. L. Zhang, Bioorg. Med. Chem. Lett. 2011, 21, 5177.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVKisr3P&md5=2bd62b36d644aa236f05629846450eedCAS | 21835617PubMed |
[34] J. Cui, M. L. Li, M. S. Yuan, J. Pestic. Sci. 2012, 37, 95.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xmt12ksL8%3D&md5=3a037014c3084f5217987d3668134d88CAS |
[35] G. Goudar, A. R. Alagawadi, J. Biopestic. 2012, 5, 208.
| 1:CAS:528:DC%2BC3sXlsVOlsA%3D%3D&md5=d1f8542198e6b3927e4438510ae33021CAS |
[36] Q. Feng, Z. L. Liu, L. X. Xiong, M. Z. Wang, Y. Q. Li, Z. M. Li, J. Agric. Food Chem. 2010, 58, 12327..
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlOiu7jO&md5=cd7ac87e2a92793519c7d9c9b5c78e26CAS | 21047132PubMed |
[37] J. Wu, B. A. Song, D. Y. Hu, M. Yue, S. Yang, Pest Manag. Sci. 2012, 68, 801.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1GhurbO&md5=dc6c8e57fe16a9fa5424b369a450ee18CAS | 22190278PubMed |
[38] C. P. Moraes, L. A. Foerster, Cienc. Rural 2012, 42, 1335.
| Crossref | GoogleScholarGoogle Scholar |
