Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against<i>Gaeumannomyces graminis</i>var.<i>tritici.</i>

Xie, Guiying; Jin, Wenbo; Zhao, Yong Qing; Cheng, Yuyu; Sun, Bing‐Jian; Sun, Shujun; Wang, Meizi; Wei, Dandan; Li, Honglian

doi:10.6023/cjoc201401036

Cited by 6 publications

(5 citation statements)

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“…小麦全蚀病是危害小麦的一种顽固土传病害 [17] , 大多数杀菌剂对其防治效果不够理想, 在目前的杀菌剂品种中, 硅噻菌胺是少数能够有效防治小麦全蚀病的芳甲酰胺类杀菌剂, 但品种单一. 为了解决小麦全蚀病防治品种单一的问题, 并结合芳甲酰胺衍生物在不同生物学领域良好的生物活性表现, 课题组近来也开展了芳甲酰胺类化合物的合成与活性研究 [18][19] , 发现具有不同结构的噻吩甲酰胺衍生物对小麦全蚀病具有优异的抑制活性, 然而有关取代的苯甲酰胺衍生物对防治小麦全蚀病的活性研究还涉及得较少; 作为该工作的进一步延伸, 本文拟设计合成一系列取代的苯甲酰胺衍生物, 研究它们的结构与活性关系, 以期获得对小麦全蚀病具有抑制活性的新先导化合物.…”

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Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Jiang¹,

Cheng²,

Shen³

et al. 2020

Chin. J. Org. Chem.

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The synthetic route of substituted 1,2,4-triazole benzamide derivatives was explored, which included several steps such as catalytic cross-coupling of 2,6-dichlorobenzonitrile with a triazole, amidation of nitrile, diazotization of amide and hydrolysis, and amidation of acid. Unreported 14 new 1,2,4-triazole benzamide derivatives were synthesized. Their chemical structures were characterized by 1 H NMR, 13 C NMR and HRMS. Their antifungal activities against Gaeumannomyces graminis var. tritici and Fusarium pseudocerealum were evaluated in vitro by the plate method. The results indicated that antifungal activities of compound 2-chloro-N-phenyl-6-(1H-1,2,4-triazol-1-yl)benzamide (7i) against Gaeumannomyces graminis var. tritici reached up to 80% at the concentrations of 100 mg/L, and were comparable to the control level of silthiopham at the concentrations of 50 and 25 mg/L. However, these compounds didn't show obvious antifungal activities against Fusarium pseudocerealum. Keywords 1,2,4-triazobenzamide derivatives; synthesis; Gaeumannomyces graminis var. tritici; antifungal activity 芳甲酰胺类衍生物是具有广泛生物活性的一类化合物, 多年来备受关注. 苯甲酰衍生物在医药领域发挥着重要的作用, 取代的苯甲酰胺在精神分裂症抑制 [1] 、癌细胞的控制 [2][3] 、对感染 HIV-1 潜伏期细胞的清除 [4] 等方面发挥良好活性. 一些结构的苯甲酰胺作为鱼尼丁受体(RyR)抑制剂具有优良的杀虫活性 [5][6][7][8] , 已经商品化的有氯虫苯甲酰胺(Chlorantraniliprole) [9] 、溴氰虫酰胺 (Cyantraniliprole) [10] 等(图 1). 在除草剂领域, 苯甲酰胺衍生物可以抑制乙酰乳酸合成酶(AHAS), 从而发挥除草活性 [11] . 近年来, 芳甲酰胺类衍生物在杀菌剂领域的研究也比较活跃, 一系列的芳甲酰胺化合物被开发为杀菌剂 [12] , 如商品化的品种有啶酰菌胺(Boscalid)

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Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Jiang¹,

Cheng²,

Shen³

et al. 2020

Chin. J. Org. Chem.

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“…以噻吩为结构骨架的化合物在生物活性化合物家族中也占有重要比重 [11] , 如 3-苯基-5-(噻吩-2)-1,2,4-噁二唑已开发为杀虫剂 (tioxazafen) [6] , 而噻菌腈 (thicyofen) [7] 、噻唑菌胺 (ethaboxam) [8] 、硅噻菌胺 (silthiopham) [9] 、吡噻菌胺(penthiopyrad) [10] 等已分别开发为农用杀菌剂. 近来我们也致力于噻吩活性化合物的合成与开发 [11,12] [20] 、三乙烯二胺 (DAB-CO) [21] 、三乙胺 [22] …”

Section: 苯甲酰硫脲的核苷衍生物对水稻纹枯病(Rhizoctonia Solani)和芦笋茎枯病(phomopsisasparagunclassified

Synthesis of Thiophene Formyl Thiourea Derivatives and Fungicidal Activity

Cheng¹,

Jin²,

Xie³

et al. 2016

Chin. J. Org. Chem.

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13 New thiophene formyl thiourea derivatives were synthesized via cycloaddition reaction of 3-mercaptobutan-2-one and methyl 3-(substitutedsilyl)propiolate, selective hydrolysis of ester, isothiocyanatation and amination. Their chemical structures were confirmed by 1 H NMR, 13 C NMR and elemental analysis. The inhibitory activity against Gaeumannomyces graminis var. tritici and Rhizoctonia solani was evaluated in vitro by the plate method. The results indicated that most of thiophene formyl thiourea derivatives showed some inhibitory activity against gaeumannomyces graminis var. tritici. Compound 1-cyclopropyl-3-(4,5-dimethylthiophene-3-carbonyl)thiourea (8c) gave the best performance and its inhibitory activity was close to the control level of silthiopham in the concentration of 10 mg/L. The structure analysis showed that the steric hindrance of functional group at the second position of the thiophene formyl thioureas had no obvious effect on the inhibitory activity against gaeumannomyces graminis var. tritici.

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“…synthesized a series of thiophene carboxamide derivatives that have significant inhibition effects against gaeumannomyces graminis var. tritici . Meanwhile, Cudworth et al .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

Wang

Ren

Mei

et al. 2018

Journal of Heterocyclic Chem

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A series of 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group were designed and synthesized by integrating a thiophene nucleus and a pyrroline‐2‐one scaffold in a single molecular architecture. Their structures were confirmed by IR, 1H‐NMR, EI‐MS, and elemental analyses, and their antifungal activities against Fusarium graminearum (Fg), Rhizoctorzia solani (Rs), and Botrytis cinerea (Bc) were evaluated. The antifungal bioassays indicated that some title compounds exhibited desirable antifungal effects against the tested fungi. Strikingly, the title compounds 4i, 4k, 4n, and 4o showed obvious antifungal activities against Rs, with corresponding EC50 values of 35.26, 33.56, 23.90, and 30.48 μg/mL, respectively, which are better than that of hymexazol (37.86 μg/mL). These results indicated that 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group can serve as potential structural templates in the search for novel high‐efficient fungicides.

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Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity againstGaeumannomyces graminisvar.tritici.

Cited by 6 publications

References 5 publications

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Synthesis of Thiophene Formyl Thiourea Derivatives and Fungicidal Activity

Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

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