Journal of Agricultural and Food Chemistry p. 10942 - 10951 (2012)
Update date:2022-08-04
Topics:
Ou, Junjun
Zhu, Xiaokun
Wang, Lei
Xu, Chuan
Liu, Feng
Ren, Long
Xu, Xibao
Wang, Yi
Rui, Changhui
Liu, Shangzhong
The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using 1H nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (EI-MS), and their biological activities at a concentration of 600 mg L -1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A. gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of <90 mg L-1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at R1 play crucial roles in the biological activities of the compounds.
View MoreContact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Contact:0086-27-83607103/83642615
Address:No.498, Jianshe Ave, Wuhan, China
Nanjing Chemlin Chemical Co., Ltd.
website:http://www.echemlin.cn
Contact:+86-25-83697070
Address:Rm.902 Longyin Plaza, No. 217 Zhongshan Rd.(N) Nanjing 210009,China
Jiaxing Trustworthy Import And Export Co.,Ltd
Contact:+86-573-82030555
Address:Room 1202, Unit B, Charming plaza,No.1558 East Zhongshan Road , Jiaxing City, Zhejiang Province, China.
Contact:021-36356756
Address:Room601,Building No.14,280 Yangcheng Road,Shanghai
Doi:10.1021/acs.organomet.1c00354
(2021)Doi:10.1039/DT9910002777
(1991)Doi:10.1007/s00044-012-0458-3
(2013)Doi:10.1002/chem.201103876
(2012)Doi:10.1021/jo301001j
(2012)Doi:10.2174/157340612801216193
(2012)