A series of novel fused heterocyclic compounds bearing benzo[4,5]imidazo[1,2-d][1,2,4]triazine 4a-4w were designed and conveniently synthesized via the intermediates 2-(halogenated alkyl)-1H-benzo[d]imidazoles 2a, 2b, and 2-((1-(substituted phenyl)hydrazinyl)alkyl)-1H-benzo[d]imidazoles 3a-3g. The structures of all target compounds were characterized by FT-IR, ¹H NMR, 13C NMR, and EI-MS, of which, the structure of compound 4n was further determined by the single crystal X-ray diffraction. The crystal structure of 4n was crystallized in the triclinic crystal system, space group P 1 ¯ with a = 9.033 (6) Å, b = 10.136 (7) Å, c = 10.396 (7) Å, α = 118.323 (7)°, β = 91.750 (8)°, γ = 104.198 (7)°, Z = 2, V = 800.2 (9) ų; total R indices: R₁ = 0.0475, wR₂ = 0.1284. The antifungal activity of title compounds 4a-4w in vitro against the phytopathogenic fungi Botrytis cinerea (B. cinerea), Rhizoctonia solani (R. solani) and Colletotrichum capsici (C. capsici) were evaluated, the bioassay results demonstrated that most of the title compounds exhibited obvious fungicidal activities at 50 μg/mL. This work indicated that benzo[4,5]imidazo[1,2-d][1,2,4]triazine derivatives could be considered as a new leading structure in searching for novel agricultural fungicides.

中文翻译：

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新型苯并[4,5]咪唑并[1,2-d] [1,2,4]三嗪衍生物的合成，表征和抗真菌活性。

设计了一系列新颖的带有苯并[4,5]咪唑并[1,2-d] [1,2,4]三嗪4a-4w的稠合杂环化合物，并通过中间体2-（卤代烷基）-1H-合成苯并[d]咪唑2a，2b和2-（（1-（取代的苯基）肼基）烷基）-1H-苯并[d]咪唑3a-3g。通过FT-IR，1 H NMR，13 C NMR和EI-MS表征所有目标化合物的结构，其中，化合物4n的结构通过单晶X射线衍射进一步确定。4n的晶体结构在三斜晶系中结晶，空间群P 1为a = 9.033（6）Å，b = 10.136（7）Å，c = 10.396（7）Å，α= 118.323（7）° ，β= 91.750（8）°，γ= 104.198（7）°，Z = 2，V = 800.2（9）ų；总R指数：R 1 ＝ 0.0475，W R 2 ＝ 0.1284。评价了标题化合物4a-4w在体外对植物病原性真菌灰葡萄孢（B. cinerea），茄子根瘤菌（R. solani）和辣椒炭疽菌（C. capsici）的抗真菌活性，生物测定结果表明，大多数标题化合物在50μg/ mL处显示出明显的杀菌活性。这项工作表明，苯并[4,5]咪唑并[1,2-d] [1,2,4]三嗪衍生物可以被认为是寻找新型农业杀菌剂的新的主导结构。