1268356-15-5Relevant articles and documents
Synthesis, bioactivities and structure activity relationship of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N'-phenyl Ureas
Guo, Dandan,Wang, Zhiwen,Fan, Zhijin,Zhao, Hui,Zhang, Wei,Cheng, Jiagao,Yang, Jiaqiang,Wu, Qingjun,Zhang, Youjun,Fan, Qian
, p. 2522 - 2532 (2013/01/15)
Twenty nine novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-phenyl ureas were designed and synthesized, and their structures were confirmed by proton nuclear magnetic resonance (1H NMR), infra red spectroscopy (IR) and high-resolution mass spectroscopy (HRMS). Compounds V-9, V-11, V-12, V-15, V-19, V-21, V-22 and V-24 exhibit excellent activity against Culex pipiens pallens. Compounds V-12 and V-22 present good insecticidal activity against Plutella xylostella L. Their median lethal concentrations (LC50) are 164.15 and 89.69 mg·L-1, respectively. Compound V-11 also has potential wide spectrum of fungicide activity. Its median effective concentrations (EC50) detected from 3.82 iμg·mL -1 against Physalospora piricola to 31.60 iμg· mL-1 against Cercospora arachidicola. Compounds V-15 and V-24 show outstanding induction activities as same as positive controls TDL and ningnanmycin, furthermore V-24 has the highest induction activity of 41.85%i±4.43%. To elucidate the structure activity relationship in these compounds, a 3D-QSAR model has been built. The established model showed a reliable predicting ability with q2 values of 0.643 and r 2 values of 0.982. 29 novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl- N'-phenyl ureas were designed and synthesized. Target compounds exhibit insecticidal activities. Bioassays indicated that compounds V-24 and V-22 exhibit outstanding insecticidal activity against Culex pipiens pallens and Plutella xylostella, respectively. Compound V-11 also has a broad-spectrum of fungicide activity against all the fungi tested. Five compounds show good SAR-inducing activity as well. These results establish basis for both disease and insect control in agricultural practice and novel pesticide development. Structure-activity relationship studies reveal that, with the contour maps based on steric and electrostatic CoMFA coefficients, we can conclude the relationship between the structures and bioactivity and continue the further design of highly active compounds. Copyright
