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Molecules 2018, 23(6), 1473; https://doi.org/10.3390/molecules23061473

Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs

1
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, 221st Beisi Road, Shihezi 832002, China
2
Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Production and Construction Group, School of Chemistry and Chemical Engineering, 221st Beisi Road, Shihezi 832003, China
3
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co., Ltd., No. 8-1 Shenliao Dong Road, Tiexi District, Shenyang 110021, China
*
Authors to whom correspondence should be addressed.
Received: 15 May 2018 / Revised: 12 June 2018 / Accepted: 16 June 2018 / Published: 18 June 2018
(This article belongs to the Section Medicinal Chemistry)
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Abstract

For the first time, a novel series of tschimganin analogs were designed, synthesized, and evaluated for their insecticidal and fungicidal activities. Their structures were characterized by 1H-NMR, 13C-NMR and HRMS. Some of these compounds displayed excellent insecticidal and fungicidal activities, suggesting that they have potential to be used as bifunctional agrochemicals. Compound 3d and 3g with electron donating groups showed better inhibitory activity and growth inhibition activity towards Helicoverpa armigera (Hübner). The properties and positions of the substituents on the benzene ring have an important influence on the acaricidal activity of tschimganin analogs. Topomer comparative molecular field analysis (CoMFA) was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds against Tetranychus turkestani Ugarov et Nikolski. It was indicated that higher electronegativity was beneficial for acaricidal activity. Moreover, compound 3r having a 2-hydroxy-3,5- dinitrophenyl moiety displayed a fungicidal spectrum as broad as azoxystrobin against these phytopathogens. View Full-Text
Keywords: tschimganin analogs; insecticidal activities; fungicidal activity; structure-activity relationship (SAR) tschimganin analogs; insecticidal activities; fungicidal activity; structure-activity relationship (SAR)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Zhou, Y.; Wang, C.; Xin, F.; Han, X.; Zhang, J.; Sun, K. Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs. Molecules 2018, 23, 1473.

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