Fungicidal Properties of Some Novel Trifluoromethylphenyl Amides
Fungicidal Properties of Some Novel Trifluoromethylphenyl Amides
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DOI：
10.1002/cbdv.201800618
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发表时间：
2019-05
影响因子：
2.9
通讯作者：
M. Tsikolia;U. Bernier;D. Wedge;N. Tabanca;K. Abboud;K. Linthicum
中科院分区：
文献类型：
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作者：
M. Tsikolia;U. Bernier;D. Wedge;N. Tabanca;K. Abboud;K. Linthicum
三氟甲基苯基酰胺（TFMPA）被设计和合成为潜在的农药。使用直接生物自显影测定评估了 33 个结构对三种炭疽菌属物种的杀菌活性。随后对活性化合物进行了针对草莓隐孢子虫、胶孢隐孢子虫、尖孢隐孢子虫、暗纹拟茎点霉、葡萄霉、灰葡萄孢和尖孢镰刀菌的测试。该研究确定 2-氯-N-[2,6-二氯-4-(三氟甲基)苯基]乙酰胺 (7a) 在这组药物中对尖头炭疽菌（48 和 72 小时）和葡萄茎点霉（144 小时）表现出最强的抗真菌活性和最广泛的活性谱。三乙胺在其与 N-[2,6-二氯-4-(三氟甲基)苯基]-2,2,3,3,3-五氟丙酰胺 (7b') 的复合物中的存在在生物活性中发挥了重要作用，并且根据浓度或真菌种类，它表现出比母体酰胺更高或更低的活性。 X射线晶体学表明，配合物（7b′）是一个离子对，（C10H2Cl2F8NO）−（C6H16N）+，其中质子从酰胺氮转移到三乙胺氮，然后通过氢键连接到酰基氧（N−H 0.893 Å; H⋅⋅⋅O 1.850 Å; N⋅⋅⋅O 2.711 Å; N−H⋅⋅⋅O 161.2(13)°)。尽管这些化合物均不优于标准化合物，但这项工作揭示了一些潜在的先导结构，可用于进一步开发活性新型化合物。
Trifluoromethylphenyl amides (TFMPAs) were designed and synthesized as potential pesticides. Thirty‐three structures were evaluated for fungicidal activity against three Colletotrichum species using direct bioautography assays. Active compounds were subsequently tested against C. fragariae, C. gloeosporioides, C. acutatum, Phomopsis obscurans, P. viticola, Botrytis cinerea and Fusarium oxysporum. The study identified 2‐chloro‐N‐[2,6‐dichloro‐4‐(trifluoromethyl)phenyl]acetamide (7a) as showing the strongest antifungal activity, and the broadest activity spectrum in this set against Colletotrichum acutatum (at 48 and 72 h) and Phomopsis viticola (at 144 h). The presence of triethylamine in its complex with N‐[2,6‐dichloro‐4‐(trifluoromethyl)phenyl]‐2,2,3,3,3‐pentafluoropropanamide (7b′) played an important role in the bioactivity, and depending on the concentration or fungal species it showed higher or lower activity than the parent amide. X‐Ray crystallography has shown that the complex (7b′) is an ion pair, (C10H2Cl2F8NO)− (C6H16N)+, where a proton is transferred from the amide nitrogen to the triethylamine nitrogen and then connected by hydrogen bonding to the acyl oxygen (N−H 0.893 Å; H⋅⋅⋅O 1.850 Å; N⋅⋅⋅O 2.711 Å; N−H⋅⋅⋅O 161.2(13)°). Although none of these compounds were better than standards, this work revealed some potential lead structures for further development of active novel compounds.