Design, Synthesis, and Fungicidal Activities of Novel Piperidyl Thiazole Derivatives Containing Oxime Ether or Oxime Ester Moieties was written by Bian, Qiang;Zhao, Rui-Qi;Peng, Xing-Jie;Gao, Li-Jie;Zhou, Guo-Na;Yu, Shu-Jing;Zhao, Wei-Guang. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Synthetic Route of C11H20N2O2S This article mentions the following:
To explore the influence of the positions of the two nitrogen atoms on the thiazole ring and the isoxazoline ring on the activity, a series of novel piperidyl thiazole derivatives containing oxime ether and oxime ester moieties with two nitrogen atoms on the same or opposite sides have been designed, synthesized, and first evaluated for their fungicidal activities against Phytophthora capsiciin vitro. The bioassay results showed that the target compounds possessed moderate to good fungicidal activities against P. capsici, among which oxime ether compound I shows the highest fungicidal activity in vitro (EC50 = 0.0104μg/mL) which is higher than dimethomorph (EC50 = 0.1148μg/mL) and diacetylenyl amide (EC50 = 0.040μg/mL). Compared with oxime ether compounds (the two nitrogen atoms are on the opposite sides), the activities of oxime ester compounds were significantly reduced. It is different from the com. fungicide fluoxapiprolin, and the activities of the compounds with the two nitrogen atoms on the same side were significantly reduced compared to the compounds with the two nitrogen atoms on the opposite sides. Moreover, some compounds showed moderate to good antifungal activities in vivo against Phytophthora capsici, Pseudoperonospora cubensis, and Phytophthora infestans. SEM of compound I on the hyphae morphol. showed that compound I might cause mycelial abnormalities of P. capsici. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1Synthetic Route of C11H20N2O2S).
tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (cas: 214834-18-1) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Synthetic Route of C11H20N2O2S