benzo-1,2,3-thiadiazole-7-carboxylic acid 2,2,2-trifluoroethyl ester | 864237-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: benzo-1,2,3-thiadiazole-7-carboxylic acid 2,2,2-trifluoroethyl ester
• 英文别名: benzo[d][1,2,3]thiadiazol-7-carboxylic acid trifluoroethyl ester；benzo-1,2,3-thiadiazole-7-carboxylic acid trifluoroethyl ester；2,2,2-trifluoroethtyl benzo[1,2,3]thiadiazole-7-carboxylate；2,2,2-trifluoroethyl benzo-1,2,3-thiadiazole-7-carboxylate；2,2,2-trifluoroethylbenzo[1,2,3]thiadiazole-7-carboxylate；2,2,2-Trifluoroethyl 1,2,3-benzothiadiazole-7-carboxylate
• CAS: 864237-81-0
• 化学式: C₉H₅F₃N₂O₂S
• 分子量: 262.212
• InChiKey: QIMRGIBYPSZWFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  8

制备方法与用途

化学性质

氟唑活化酯是一种无气味、浅棕色的粉末状物质，熔点为94.5~95.5℃。该化合物易溶于丙酮、乙酸乙酯、二氯甲烷和甲苯等有机溶剂中，在正已烷中的溶解度为8.5g/L，在水中的溶解度仅为0.03g/L。其pH值为4.6，正辛醇-水分配系数在20℃时约为2.90，饱和蒸气压在25℃下为3.31×10^-4Pa。氟唑活化酯在室温下稳定，不具有燃烧性，在50~500℃内的放热效应小于500J/g，并且没有爆炸危险或对包装材料的腐蚀性。与水、磷酸二氢铵、铁粉和煤油混合未发现明显反应，不存在氧化-还原/化学不相容性；但在0.1mol/L KMnO4溶液中会变色，表明存在氧化-还原/化学不相容性。5%氟唑活化酯乳油具有芳香族化合物的气味，呈现黄褐色透明液体状，密度为0.93g/mL，闪点为55.0℃，无爆炸性和腐蚀性。

毒性

原药：对大鼠（雌雄）急性经口毒性LD50值为1080mg/kg，急性经皮毒性LD50大于5000mg/kg，急性吸入LC50大于2000mg/m³。对于兔眼和兔皮肤无刺激性，豚鼠致敏性试验结果为弱致敏。Ames、微核及染色体试验结果均为阴性。

应用

氟唑活化酯FBT兼具抗病与抗虫特性，通过简单的叶面喷洒，可以有效防治各类土传病害，尤其对土豆土传病害防治效果显著。施药浓度在10~20mg/L之间，在定植期开始施药，并每7天施药一次，连续施用4次可较好地防治黄瓜霜霉病和白粉病且不会产生药害。

合成方法

氟唑活化酯可通过以下反应制得：

反应信息

• 作为产物：
  描述：

  阿拉酸式苯 在 氯化亚砜 、 三乙胺 作用下， 生成 benzo-1,2,3-thiadiazole-7-carboxylic acid 2,2,2-trifluoroethyl ester
  参考文献：
  名称：

  Novel Benzo-1,2,3-thiadiazole-7-carboxylate Derivatives As Plant Activators and the Development of Their Agricultural Applications

  摘要：

  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 H-1 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.

  DOI：

  10.1021/jf203974p

文献信息

• 一种苯并[d][1,2,3]噻二唑-7-甲酸三氟乙酯 的制备方法
  申请人：南通泰禾化工股份有限公司

  公开号：CN107344928B

  公开（公告）日：2020-02-14

  本发明提供一种苯并[d][1,2,3]噻二唑‑7‑甲酸三氟乙酯的制备方法，所述方法以4‑二甲氨基吡啶为催化剂，使苯并[d][1,2,3]噻二唑‑7‑甲酸与三光气反应，得到苯并[d][1,2,3]噻二唑‑7‑甲酰氯；将得到的苯并[d][1,2,3]噻二唑‑7‑甲酰氯与三氟乙醇和碳酸盐反应，得到苯并[d][1,2,3]噻二唑‑7‑甲酸三氟乙酯。所述制备方法三废少、成本低、反应条件温和、方法简单，且苯并[d][1,2,3]噻二唑‑7‑甲酸三氟乙酯的纯度高、收率高。
• 一种氟唑活化酯的制备方法
  申请人：南通泰禾化工股份有限公司

  公开号：CN107235929B

  公开（公告）日：2019-06-21

  本发明提供了一种氟唑活化酯的制备方法，所述方法为：在酸催化下，使苯并[d][1,2,3]噻二唑‑7‑甲酸与三氟乙醇反应得到氟唑活化酯。本发明通过采用酸作为催化剂，直接一步实现苯并[d][1,2,3]噻二唑‑7‑甲酸与三氟乙醇的酯化反应，工艺简洁，可减少设备投资，并且产物产率高，纯度高，无需采用二氯亚砜或草酰氯等酰氯化原料，也不需要使用吸收酯化反应产生的氯化氢的三乙胺等碱，直接降低氟唑活化酯制备的原料成本；没有副产气体需要处理，可减少设备投资和副产或废气处理成本，原料可以回收利用，减少三废产生量和处理费用，减少氟唑活化酯的整体生产成本。
• Derivatives of benzothiadiazole-7-carboxylates: synthesis and biological activity
  作者：Weiping Zhu、Zhenjiang Zhao、Yufang Xu

  DOI：10.1007/s00706-008-0887-3

  日期：2008.9

  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.
• Novel, Unnatural Benzo-1,2,3-thiadiazole-7-carboxylate Elicitors of Taxoid Biosynthesis
  作者：Yufang Xu、Zhengjiang Zhao、Xuhong Qian、Zhigang Qian、Wenhong Tian、Jianjiang Zhong

  DOI：10.1021/jf0618574

  日期：2006.11.1

  In order to establish the chemical biological technology for production of valuable secondary metabolites, a novel family of unnatural elicitors derived from the plant activator benzo-1,2,3-thiadiazole-7-carboxylic acid were designed and synthesized. New synthetic elicitors that showed powerful eliciting activities upon taxoid biosynthesis by Taxus chinensis suspension cells were obtained. For example, benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoxyl) ethyl ester was more effective and resulted in nearly 40% increase in taxuyunnanine C content and production in comparison with methyl jasmonate, which was previously reported as the most powerful chemical elicitor for taxoid biosynthesis. The novel class of elicitors was found to induce plant defense responses, including promotion of H2O2 levels originating from oxidative burst and activation of phenylalanine ammonia lyase. Interestingly the plant defense responses induced corresponded well to the superior stimulating activity in T. chinensis cell cultures. The work indicates that the newly synthesized benzothiadiazoles can act as a new family of elicitors for taxoid biosynthesis in plant cells.
• [EN] APPLICATION OF AN ELICITOR IN CONTROL OF SOIL-BORN DISEASES OF GARDEN CROPS<br/>[FR] APPLICATION D'UN ÉLICITEUR POUR LA LUTTE CONTRE LES MALADIES DU SOL DANS LES CULTURES HORTICOLES
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2011107030A1

  公开（公告）日：2011-09-09

  Application of an elicitor S-methyl benzo-1,2,3-thiadiazole-7-carbothioate and/or trifluoroethyl benzo-1,2,3-thiadiazole-7-carboxylate in control of soil-born diseases of garden crops is provided, including diseases caused by Fusarium oxysporum, Pythium aphanidermatum, Rhizoctonia solani, Sclerotinia sclerotiorum etc.. The elicitor is applied by singly spraying or immersing seed combined with spraying. The elicitor has significant disease resistance-inducing effect and long action.