23621-08-1Relevant articles and documents
Efficient solid phase synthesis of benzo[1,2,3]thiadiazoles and related structures
Kreis, Michael,Nising, Carl F.,Schroen, Maarten,Knepper, Kerstin,Braese, Stefan
, p. 1835 - 1837 (2005)
The first solid-phase synthesis of benzo[1,2,3]thiadiazoles was achieved by starting from resin bound ortho bromo or iodo triazenes and using a functionalization on cleavage. Two different synergistic methods including an anionic approach and a cross-coupling approach were used for the synthesis. The resulting diazonium compounds readily underwent electrophilic cyclization yielding benzothiadiazoles, when cleaving the arenethiol resins. Cleavage from the resin with diluted trifluoroacetic acid resulted spontaneously in the desired cyclization reaction.
Novel benzo-1,2,3-thiadiazole-7-carboxylate derivatives as plant activators and the development of their agricultural applications
Du, Qingshan,Zhu, Weiping,Zhao, Zhenjiang,Qian, Xuhong,Xu, Yufang
, p. 346 - 353 (2012/04/10)
Plant activators are a novel kind of agrochemicals that could induce resistance in many plants against a broad spectrum of diseases. To date, only few plant activators have been commercialized. In order to develop novel plant activators, a series of benzo-1,2,3-thiadiazole-7-carboxylate derivatives were synthesized, and the structures were characterized by 1H NMR, IR, elemental analyses, and HRMS or MS. Their potential systemic acquired resistance as plant activators was evaluated as well. Most of them showed good activity, especially, fluoro-containing compounds 3d and 3e, which displayed excellent SAR-inducing activity against cucumber Erysiphe cichoracearum and Colletotrichum lagenarium in assay screening. Field test results illustrated that compounds 3d and 3e were more potent than the commercial plant activator, S-methyl benzo[1,2,3]thiadiazole-7-carbothioate (BTH) toward these pathogens. Further, the preparation of compound 3d is more facile than BTH with lower cost, which will be helpful for further applications in agricultural plant protection.
Derivatives of benzothiadiazole-7-carboxylates: Synthesis and biological activity
Zhu, Weiping,Zhao, Zhenjiang,Xu, Yufang
scheme or table, p. 1067 - 1071 (2009/12/02)
Salicylic acid (SA) and methyl jasmonate (MJ) are important plant signal molecules to cause systemic acquired resistance (SAR), while it's reported that they also have wide spectrum antitumor activities. Benzothiadiazole-7- carboxylates are plant activators which can cause SAR just like SA and MJ. To investigate whether the benzothiadiazole-7-carboxylate family is endowed with anticancer activities, several benzothiadiazole-7-carboxylate derivatives are synthesized and their inhibition to P388 murine leukemia cell and A549 human lung cancer cell compared with MJ are evaluated. The data indicated that benzo-1,2,3-thiadiazole-7-carboxylic acid 2-benzoyloxyethyl ester has a higher inhibition ability to the cancer cell P388 and A549, compared with MJ.
