benzo[1,2,3]thiadiazole-7-carboxylic acid methtyl ester | 23621-08-1

• 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 methtyl ester
• 英文别名: Methyl benzo[1,2,3]thiadiazole-7-carboxylate；methyl 1,2,3-benzothiadiazole-7-carboxylate；7-Methoxycarbonyl-1,2,3-benzothiadiazol；Methyl-1,2,3-Benzothiadiazol-7-carboxylat；benzo[1,2,3]thiadiazole-7-carboxylic acid methyl ester；7-Carbomethoxy-1,2,3-benzothiadiazol；1,2,3-Benzothiadiazole-7-carboxylic acid, methyl ester
• CAS: 23621-08-1
• 化学式: C₈H₆N₂O₂S
• 分子量: 194.214
• InChiKey: CUIIHNPMMCYAMK-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  304.4±34.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzo[1,2,3]thiadiazole-7-carboxylic acid methtyl ester 在 一水合肼 作用下， 以 水 为溶剂， 生成 benzo-1,2,3-thiadiazole-7-carboxylic acid hydrazide
  参考文献：
  名称：

  Process and a composition for immunizing plants against diseases

  摘要：

  一种用于对健康有益的植物进行免疫接种以防止植物病害的方法和组合物，其中活性成分是公式##STR1##的化合物，其中：X是氢、卤素、羟基、甲基、甲氧基、羧基或甲氧羧基；Y是氢、卤素、磺酸基、甲磺酸基、硝基、羟基或氨基，M是一个碱金属或碱土金属离子的摩尔当量，该金属离子由相应的碱或碱性化合物形成；Z是氰基或--CO--A；A代表--OH或--SH，其中的氢原子也可以被无机或有机阳离子残基的摩尔当量所取代，或者其中A代表任意的其它有机残基，其分子量小于900，并且也可以包含一个或多个杂原子，包括与初级、次级或三级胺或无机碱形成的植物生理上可容忍的7-羧酸或7-硫羧酸的盐。

  公开号：

  US04931581A1
• 作为产物：
  描述：

  2-氯-3,5-二硝基苯甲酸 在 镍 氢气 、 氢气 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzo[1,2,3]thiadiazole-7-carboxylic acid methtyl ester
  参考文献：
  名称：

  The Chemistry of Benzothiadiazole Plant Activators

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199708)50:4<275::aid-ps593>3.0.co;2-7

文献信息

• One- and Two-Proton Transfer Mechanisms Coexist in One Active Site
  作者：Yueqi Zhao、Huaikun Dong、Jing Ren、Jiali Song、Jianzhuang Yao、Juan Gao、Cheng-Shi Jiang、Xia Wang

  DOI：10.1021/acs.jpcb.0c04445

  日期：2020.8.6

  different catalytic mechanisms toward different substrates. To catalyze the ASM hydrolysis, the SABP2 uses a two-proton transfer mechanism, and the key intermediate is stabilized by the charge transfer effect; to catalyze the ethyl 1,2,3-benzothiadiazole-7-carboxylate (BTM, an ASM analogue) hydrolysis, the SABP2 applies the one-proton transfer mechanism, and the classic tetrahedral intermediate is stabilized

  Acibenzolar-小号-甲基（ASM）是最成功的商业化系统获得性抗性（SAR）的植物激活剂之一。但是，由水杨酸结合蛋白2（SABP2）催化的激活（水解）机制仍然难以捉摸。通过大量的计算和实验研究，包括QM / MM模拟，电荷转移分析，小分子合成和生化分析，研究了SABP2催化ASM水解的基本催化机理。在这里我们报告说，混杂的SABP2对不同的底物显示出不同的催化机制。为了催化ASM水解，SABP2使用了两个质子转移机制，关键中间体通过电荷转移作用得以稳定。催化1,2,3-苯并噻二唑-7-羧酸乙酯（BTM，ASM类似物）水解，SABP2采用单质子转移机制，经典的四面体中间体通过静电作用得以稳定。HPLC分析SABP2酯酶对ASM和BTM的活性，可与我们的计算结果相媲美，这表明所获得的计算机理是合理的。所获得的机理不仅是酶催化混杂理论的重要补充，而且为下一代植物SAR活化剂的设计提供了可
• Compositions for protecting plants against disease
  申请人：Ciba-Geigy Corporation

  公开号：US05051436A1

  公开（公告）日：1991-09-24

  Novel N-acyl- and N-sulfonylbenzo-1,2,3-thiadiazole-7-carboxylic acid amides of formula ##STR1## in which X.sub.1 and X.sub.2 independently of one another are each hydrogen or together 1 to 3 halogen atoms; A is sulfonyl or carbonyl; Y is phenyl or phenyl substituted by C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, halogen, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxycarbonyl, C.sub.1 -C.sub.3 alkanoyloxymethyl, cyano and/or by nitro; R is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 alkenyl or C.sub.3 -C.sub.5 alkynyl; and in which, furthermore, the group ##STR2## wherein A.sub.1 is methylene, carbonyl or sulfonyl; X.sub.3 is hydrogen, methyl or halogen; m is 2, 3 or 4; and n is zero, 1 or 2. The novel active ingredients have plant-protecting properties and are suitable especially for the preventive protection of plants against attack by phytopathogenic microorganisms such as fungi, bacteria and viruses.

  式为##STR1##的新型N-酰基和N-磺酰基苯并-1,2,3-噻二唑-7-羧酸酰胺，其中X.sub.1和X.sub.2独立地是氢或1至3个卤素原子；A是磺酰基或羰基；Y是苯基或被C.sub.1-C.sub.2烷基，C.sub.1-C.sub.2烷氧基，卤素，C.sub.1-C.sub.2卤代烷基，C.sub.1-C.sub.2烷氧羰基，C.sub.1-C.sub.3烷酰氧甲基，氰和/或硝基取代的苯基；R是氢，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4卤代烷基，C.sub.3-C.sub.5烯基或C.sub.3-C.sub.5炔基；并且其中，基团##STR2##其中A.sub.1是亚甲基，羰基或磺酰基；X.sub.3是氢，甲基或卤素；m是2、3或4；n是零，1或2。这些新型活性成分具有保护植物的性质，特别适用于预防性保护植物免受植物病原微生物（如真菌、细菌和病毒）的侵害。
• Lipoxygenase genes, promoters, transit peptides and proteins thereof
  申请人：——

  公开号：US20040103453A1

  公开（公告）日：2004-05-27

  This invention describes novel lipoxygenase genes and promoters, transit peptides and proteins derived therefrom. More specifically, this invention describes novel promoters that confer chemically inducible but not wound- or pathogen-inducible expression to an associated nucleotide sequence. The invention further describes peptides capable of targeting and associated protein to plastids and proteins having lipoxygenase activity which can be used to inhibit fungal mycotoxins. The invention also describes recombinant sequences containing such promoter sequences, and/or sequences encoding transit peptides and proteins according to the invention. The said recombinant DNA sequences may be used to create transgenic plants, but especially transgenic plants expressing a nucleotide sequence of interest in response to chemicals but not in response to wounding or pathogens.

  本发明描述了新型的脂氧合酶基因和启动子、转运肽和由此衍生的蛋白质。更具体地，本发明描述了赋予化学诱导但不是伤口或病原体诱导表达与相关核苷酸序列相关的新型启动子。该发明还描述了能够将相关蛋白质定向到质体的肽和具有脂氧合酶活性的蛋白质，可用于抑制真菌毒素。该发明还描述了包含此类启动子序列和/或根据本发明编码转运肽和蛋白质的序列的重组序列。这些重组DNA序列可用于创建转基因植物，尤其是在对化学物质做出反应但不对伤口或病原体做出反应的转基因植物表达感兴趣的核苷酸序列。
• 3-amino-2-mercaptobenzoic acid derivatives and processes for their preparation
  申请人：——

  公开号：US20020040157A1

  公开（公告）日：2002-04-04

  Compounds of the formula I 1 and disulfides thereof and salts thereof are important intermediate products for the preparation of compounds having a microbicidal and plant-immunizing action, of the formula III 2 In the compounds of the formulae I and III: X is halogen, n is 0,1,2 or 3; Z is CN, CO—A or CS—A, A is hydrogen, halogen, OR 1 , SR 2 and N(R 3 )R 4 ; R 1 to R 4 are hydrogen, a substituted or unsubstituted, open-chain, saturated or unsaturated hydrocarbon radical containing not more than 8 carbon atoms, a substituted or unsubstituted cyclic, saturated or unsaturated hydrocarbon radical containing not more than 10 carbon atoms, substituted or unsubstituted benzyl or phenethyl, a substituted or unsubstituted alkanoyl group containing not more than 8 carbon atoms, a substituted or unsubstituted benzoyl group or a substituted or unsubstituted heterocyclyl radical; or R 3 and R 4 , together with the nitrogen atom to which they are bonded, are a 5- or 6-membered, substituted or unsubstituted heterocyclic radical having 1-3 heteroatoms O, S and/or N. Processes for the preparation of compounds of the formula I are described.

  公式I1及其二硫化物和盐是制备具有杀菌和植物免疫作用的公式III2化合物的重要中间体。在公式I和III的化合物中：X为卤素，n为0、1、2或3；Z为CN、CO—A或CS—A，A为氢、卤素、OR1、SR2和N（R3）R4；R1至R4为氢、含有不超过8个碳原子的取代或未取代的开链、饱和或不饱和碳氢基团，含有不超过10个碳原子的取代或未取代的环状、饱和或不饱和碳氢基团，取代或未取代的苄基或苯乙基、含有不超过8个碳原子的取代或未取代的烷酰基团、取代或未取代的苯甲酰基团或取代或未取代的杂环基团；或R3和R4与它们所连接的氮原子一起形成一个含有1-3个杂原子O、S和/或N的取代或未取代的5-或6元杂环基团。描述了制备公式I化合物的方法。
• Process and a composition for immunizing plants against disease
  申请人：Ciba-Geigy Corporation

  公开号：US05523311A1

  公开（公告）日：1996-06-04

  A method and composition for the immunization of healthy useful plants against plant diseases containing as active ingredients compounds of formula ##STR1## in which: X is hydrogen, halogen, hydroxy, methyl, methoxy, HOOC or MOOC; Y is hydrogen, halogen, SO.sub.3 H, SO.sub.3 M, nitro, hydroxy or amino, M being the molar equivalent of an alkali metal or alkaline earth metal ion that is formed from a corresponding base or basic compound; and Z is cyano or --CO--A; A represents either --OH or --SH, the hydrogen atom of which may also be replaced by the molar equivalent of an inorganic or organic cationic residue, or wherein A represents any other organic residue which has a molecular weight of less than 900 and which may also contain one, or more than one, hetero atom, including the salts of the phytophysiologically tolerable 7-carboxylic acid or 7-thiocarboxylic acid with primary, secondary or tertiary amines or with inorganic bases.

  一种用于对健康有益植物进行免疫以防治植物疾病的方法和组合物，其包含以下化合物作为活性成分：##STR1## 其中：X为氢、卤素、羟基、甲基、甲氧基、HOOC或MOOC；Y为氢、卤素、SO.sub.3 H、SO.sub.3 M、硝基、羟基或氨基，M为相应碱基或碱性化合物形成的相应碱金属或碱土金属离子的摩尔当量；Z为氰基或--CO--A；A表示--OH或--SH，其中氢原子也可以被无机或有机阳离子残基的摩尔当量所取代，或者A表示任何其他分子量小于900且可能含有一个或多个杂原子的有机残基，包括七羧酸或七硫羧酸与一级、二级或三级胺或无机碱的植物生理学可耐受盐。