Synthesis, structural characterization and solubility of 2-（1-substituted- 1,11-undecylidene）-5-arylimino- △^3-1,3, 4-thiadiazolines

• Published in: Chinese chemical letters Vol. 20; no. 11; pp. 1267 - 1270
• Main Author: Shu Hui Jin Xiao Mei Liang Xu Yang Fu Heng Chen Dao Quan Wang
• Format: Journal Article
• Language: English
• Published: 2009
• Subjects: 噻二唑啉; 核磁共振; 水稻纹枯病菌; 溶解度; 碳同位素; 结构表征; 非极性溶剂
• ISSN: 1001-8417; 1878-5964

A series of novel 2-（1-substituted-1,11-undecylidene）-5-arylimino-△^3-1,3,4-thiadiazolines （4） were synthesized and their structure was characterized by ^1H NMR, ^13C NMR and elemental analysis. Their solubility in both polar and non-polar solvents is significantly improved owing to the introduction of ethyl or methylthio group at cyclododecyl ring as compared with parent compounds [1, 2-（1,11-undecylidene）-5-arylimino-△^3-1,3,4-thiadiazolines]. However, their fungicidal activity against Rhizoctonia solani is less than that of parent compounds. X-ray diffraction analysis of a representative compound （4d） showed that the conformation of 12-membered ring is still [3333], in which the ethyl group present at the side-exo position and the thiadiazoline ring at the comer carbon. The thiadiazoline plane is perpendicular to the cyclododecyl one.