The new chemical class N-hetaryl-[2(1H)-pyridinylidene]cyanamides were inspired by the long known five-ring structure 2-chloro-5-[2-(nitro-methylene)-1-imidazolidinyl]-pyridine (Shell) and the current development candidate flupyrimin (Meiji Seika Pharma) via scaffold hopping and the concept for designing “shortened structures” by omitting the “methylene link” as a structural feature. The most active N-hetaryl-[2(1H)-pyridinylidene]cyanamides can be synthesized on a technical scale by a simple manufacturing procedure. As full nicotinic acetylcholine receptor (nAChR) agonists, the compounds bind with low affinity at the orthosteric binding site of nAChR. In molecular modeling studies, structural differences are visible in the superposition of active N-[6′-(trifluoromethyl)[1(2H),3′-bipyridin]-2-ylidene]cyanamide onto imidacloprid (IMD) and sulfoxaflor (SXF) in bound conformation. On the basis of their physicochemical properties, the most active xylem systemic candidates offer excellent aphicidal activity in vegetables and cotton, when applied as a foliar spray, by soil drench application, or, in particular, as seed dressing for seed treatment uses. Selected candidates show good plant compatibility and reveal a better risk profile with respect to bee pollinators than the majority of currently registered nAChR competitive modulators for seed treatment uses. Applied as a seed dressing in greenhouse profiling, good to excellent control of different aphid species has been observed. In field trials, an interesting level of activity potential against cereal grain aphids (inclusive virus vector control), corn rootworm, and wireworm could be demonstrated. According to molecular modeling investigations (Fukui functions, dipole moments, and electrostatic potentials), there is a broad scope for structure optimization of the chemical class leading to proposals for novel bicyclic insecticides.

中文翻译：

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N-杂芳基-[2(1H)-pyridinyliden]cyanamides：一类新的内吸性杀虫剂

新化学类N-杂芳基-[2( 1H )-亚吡啶]氰胺的灵感来自于长期已知的五环结构 2-氯-5-[2-(硝基-亚甲基)-1-咪唑烷基]-吡啶 ( Shell）和目前的开发候选药物氟嘧啶（Meiji Seika Pharma）通过脚手架跳跃和通过省略“亚甲基连接”作为结构特征来设计“缩短结构”的概念。最活跃的N-杂芳基-[2(1 H )-亚吡啶]氰胺可以通过简单的制造程序在技术规模上合成。作为全烟碱型乙酰胆碱受体 ( n AChR) 激动剂，这些化合物在n的正构结合位点以低亲和力结合乙酰胆碱酯酶。在分子模型研究中，活性N -[6'-(三氟甲基)[1(2 H ),3'-联吡啶]-2-亚叉基]氰胺与吡虫啉 (IMD) 和磺胺嘧啶 (SXF)的叠加可见结构差异) 在结合构象中。基于它们的物理化学特性，当作为叶面喷剂、通过土壤浸湿应用或特别是作为种子处理用途的拌种剂施用时，最具活性的内吸性木质部候选物在蔬菜和棉花中提供出色的杀蚜活性。与大多数目前登记的n用于种子处理用途的 AChR 竞争性调节剂。在温室分析中用作拌种剂，已观察到对不同蚜虫种类的良好控制。在田间试验中，可以证明对谷物蚜虫（包括病毒载体控制）、玉米根虫和线虫具有有趣的活性水平。根据分子模型研究（Fukui 函数、偶极矩和静电势），该化学类别的结构优化范围很广，因此可以提出新型双环杀虫剂的建议。