N-苯甲酰基-N’-1,3,4-噻二唑-2-基硫脲的合成及生物活性研究

本文以苯甲酸为原料,经酰氯化、酰化反应得到中间体苯甲酰基异硫氰酸酯,再与2-氨基-1,3,4-噻二唑经加成反应合成并表征了10种N-苯甲酰基-N’-1,3,4-噻二唑-2-基硫脲3a-3j。初步生物活性测试结果表明:当浓度为10 mg/L时,3a～3d对小麦生根和发芽有一定的调节活性。当浓度为100 mg/L时,大部分化合物对黄瓜灰霉病菌、黄瓜炭疽病菌、水稻纹枯病菌、水稻稻瘟病菌有明显的抑制活性,而对棉花枯萎病菌的抑制活性较差。目标化合物的取代基会影响其生长调节活性和抑菌活性。结合量化计算结果讨论了化合物结构对抑菌活性的影响。

Synthesis and biological activities of N-Benzoyl-N'- ( 1,3,4-thiadiazol-2-yl) thioureas

Ten N-benzoyl-N′-(1,3,4-thiadiazol-2-yl)thioureas(3a-3j) were synthesized by addition reactions of 2-amino-1,3,4-thiadiazoles and benzoyl isothiocyanates which prepared by acyl chlorination and acylation of benzoic acids.Tests on biological activities showed that 3a-3d had good regulatory activities on the roots and buds of wheat at the concentration of 10 mg/l.Most of the compounds had obvious antifungal activities on Botrytis cinerea,Colletotrichum orbiculare,Rhizoctonia solani and Pyricularia oryzae at the concentration of 100 mg/l.But all of them had poor fungicidal activity to Fusarium oxysporium.Substituents of the target compounds affected their plant growth regulative activity and fungicidal activity.The effect of structures of the target compounds on fungicidal activity was discussed based on the results of quantum calculations.