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      Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives

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          Abstract

          A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B ( N-methyl- N- cis-styryl-cinnamamide, 2) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, 1H NMR, and 13C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of N-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.

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          Most cited references21

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          Quantification and modeling of crop losses: a review of purposes.

          This review considers the cascade of events that link injuries caused by plant pathogens on crop stands to possible (quantitative and qualitative) crop losses (damage), and to the resulting economic losses. To date, much research has focused on injury control to prevent this cascade of events from occurring. However, this cascade involves a complex succession of components and processes whereby knowledge on crop loss generates entry points for management. Proposed here is a framework linking different types of knowledge on crop loss to a range of decision categories, from tactical to strategic short- or long-term. Important advances in this field are now under way, including a probabilistic treatment of the injury-damage relationship, or analyses of the sources of uncertainty attached to some components of the decision process. Management of injury profiles, rather than individual injuries, and shifts in dimensionality of crop losses are anticipated to contribute to the design of sustainable agricultural systems, and address global issues concerning food security and food safety.
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            Antibacterial activity of Lansiumamide B to tobacco bacterial wilt (Ralstonia solanacearum).

            Tobacco bacterial wilt caused by Ralstonia solanacearum is one of the most serious diseases of tobacco in the area of tobacco cultivation. As there is no effective control method for tobacco bacterial wilt diseases, developing new antibacterial agents in tobacco will make great practical sense. The antibacterial activity against R. solanacearum of Lansiumamide B which is isolated from the seeds of Clausena lansium is reported in this paper for the first time. The bioassay results indicate that Lansiumamide B could completely inhibit the growth of R. solanacearum at the concentration of 125 mg/L in vitro, the EC50 and EC90 are 48.82 mg/L and 86.26 mg/L, respectively. The result of pot experiments indicates that the control efficiency of the Lansiumamide B on tobacco bacterial wilt are 95.84%, 91.67% and 86.38% at 7 days, 14 days and 21 days after treatment at the concentration of 100mg/kg, respectively, nearly 40 times higher than Streptomycin, a special fungicide to the disease, at 21 days after treatment with root irrigation method. These results suggest that Lansiumamide B has the potential of developing as a new type of plant-type fungicide on controlling the diseases of tobacco bacterial wilt.
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              Preparation, Characterization and Nematicidal Activity of Lansiumamide B Nano-Capsules

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                21 June 2018
                July 2018
                : 23
                : 7
                : 1499
                Affiliations
                Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China; huiyouxu@ 123456126.com (H.X.); fafuchenting@ 123456163.com (T.C.); h17746075243@ 123456163.com (L.H.); m18759775477@ 123456163.com (Q.S); fafuzengweilian@ 123456126.com (Z.L.); shiyanshelly@ 123456163.com (Y.S.); minganouyang@ 123456163.com (M.-A.O.)
                Author notes
                [* ]Correspondence: songliyan@ 123456fafu.edu.cn ; Tel.: +86-156-597-743-10
                Article
                molecules-23-01499
                10.3390/molecules23071499
                6099640
                29933580
                ca3c2f97-32f1-4795-833f-aabf2461be92
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 29 May 2018
                : 21 June 2018
                Categories
                Article

                antifungal activity,lansiumamide b,derivatives,sar,chemical synthesis

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