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Chen N.,Beijing University of Chemical Technology | Du H.,Beijing University of Chemical Technology | Liu W.,Hunan Research Institute of Chemical Industry | Wang S.,Beijing University of Chemical Technology | And 2 more authors.
Phosphorus, Sulfur and Silicon and the Related Elements | Year: 2015

A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 g/mL and 6.5 g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 g/mL, 12.1 g/mL, and 11.0 g/mL, respectively. GRAPHICAL ABSTRACT. Copyright © 2015 Taylor & Francis Group, LLC.

Cheng J.-L.,Zhejiang University | He X.-R.,Zhejiang University of Technology | Wang Z.-C.,Hunan Research Institute of Chemical Industry | Zhang J.-G.,Zhejiang University | And 3 more authors.
Pest Management Science | Year: 2013

BACKGROUND: In previous studies, scientists found that, when spirotetramat was introduced into plants or animals, it was mainly metabolised at positions C-4 and C-8. That is to say, these two functional positions potentially played an important role in spirotetramat's bioactivities. In order to develop novel insecticides or miticides, the present authors designed and synthesised 35 spirotetramat analogues based on metabolite structures. RESULTS: All of the analogues have been identified on the basis of 1H NMR, ESI-MS and elemental analysis data. The activities of these analogues were evaluated against three organisms, and biological assays indicated that compounds 5f, 5h and 5u possessed better insecticidal activities against bean aphids (Aphis fabae) than the lead compound spirotetramat. The LC50 of 5f, 5h and 5u against bean aphids reached 0.42, 0.28 and 2.53 mg L-1 respectively. Moreover, some compounds possessed comparable activities against carmine spider mite (Tetranychus cinnabarinus) and oriental armyworm (Mythimna sepatara) with spirotetramat. The structure-activity relationships (SARs) indicated that the flexible bridge at position C-4 of spirotetramat was important for its bioactivities, and the size of the group at position C-8 would have great influence on the activities. Furthermore, the log P values lower than 6.0 may be favourable for insecticidal activities. CONCLUSION: The present work demonstrates that some spirotetramat analogues can be used as potential lead compounds for developing novel insecticides, and preliminary SAR analysis would provide information for the utilisation of spirotetramat analogues as potential lipid biosynthesis inhibitors. © 2012 Society of Chemical Industry.

Yang L.-T.,Hunan University | Luo X.-F.,Hunan University | Hu A.-X.,Hunan University | Wang Y.,Hunan Research Institute of Chemical Industry
Acta Crystallographica Section E: Structure Reports Online | Year: 2011

The title compound, C21H22O5, crystallizes with three molecules in the asymmetric unit. In one molecule, two methyl groups are disordered over two positions with a site occupation factor of 0.72 (2) for the major occupancy site. The benzene rings make dihedral angles of 35.3 (6), 29.7 (6) and 40.6 (7)° in the three molecules.

Xu X.,Zhejiang University | Cheng J.,Zhejiang University | Zhou Y.,Zhejiang University | Zhang C.,Zhejiang University | And 5 more authors.
Chemistry and Biodiversity | Year: 2013

Twenty new trichodermin derivatives, 2a-5, containing alkoxy, acyloxy, and Br groups in 4-, 8-, 9-, 10- and 16-positions were synthesized and characterized. The antifungal activities of the new compounds against rice false smut (Ustilaginoidea virens), rice sheath blight (Rhizoctonia solani), and rice blast (Magnaporthe grisea) were evaluated. The results of bioassays indicated that the antifungal activities were particularly susceptible to changes at 4-, 8-, and 16-positions, but low to changes at 9- and 10-positions. Most of these target compounds exhibited good antifungal activities at the concentration of 50mg l-1. Compound 4 (9-formyltrichodermin; EC50 0.80mg l-1) with an CHO group at 9-position displayed nearly the same level of antifungal activity against Ustilaginoidea virens as the commercial fungicide prochloraz (EC50 0.82mg l-1), while compound 3f ((8R)-8-{[(E)-3-phenylprop-2-enoyl]oxy}trichodermin; EC50 3.58 and 0.74mg l-1) with a cinnamyloxy group at C(8) exhibited much higher antifungal activities against Rhizoctonia solani and Magnaporthe grisea than the commercial fungicides prochloraz (EC50 0.96mg l-1) and propiconazole (EC50 5.92mg l-1), respectively. These data reveal that compounds 3f and 4 possess high antifungal activities and may serve as lead compounds for the development of fungicides in the future. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

Li W.,Hunan University | Tang J.,Hunan University | Hu A.,Hunan University | Ye J.,Hunan University | And 2 more authors.
Chinese Journal of Organic Chemistry | Year: 2014

Benzofuran and 1,2,4-triazole have been rewarded with much priority for their broad spectrum of biological activities, especially in the agricultural field. In this specific domain, they have always been used as fungicides, pesticide and plant growth regulators etc. Consequently, a series of new compounds containing 1,2,4-triazole, 1,3-dioxolane and benzofuran moieties were designed and synthesized. 1-(2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone (4a) were prepared from 1-(4-hydroxyphenyl)ethanone in three steps. Subsequently, 2-(2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(1,2,4-triazol-1-methyl)-1,3-dioxolane (1a~1l) were synthesized from compounds 4a~4c. All compounds were verified by NMR and elemental analysis. Additionally, their fungicidal activities were evaluated against 7 kinds of crop fungus. The compounds 1a, 1b, 1e, 1f, 1g and 1l had relatively good inhibitory activity against Sclerotonia sclerotiorum, and the inhibitory rate were above 70% at 25 mg/L. Meanwhile, compounds 1a and 1b possessed potent inhibitory activity (80%) against Blumeria graminis at 500 mg/L. © 2014 Chinese Chemical Society & SIOC, CAS.

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