1-甲基-4-(2-甲基-2H-四氮唑-5-基)-1H-吡唑-5-磺酰胺 | 139481-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 1-甲基-4-(2-甲基-2H-四氮唑-5-基)-1H-吡唑-5-磺酰胺
• 中文别名: 1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰胺
• 英文名称: 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
• 英文别名: 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide；2-methyl-4-(2-methyltetrazol-5-yl)pyrazole-3-sulfonamide
• CAS: 139481-22-4
• 化学式: C₆H₉N₇O₂S
• 分子量: 243.249
• InChiKey: UEPZNFSFXYSLKP-UHFFFAOYSA-N

物化性质

• 沸点：
  568.9±60.0 °C(Predicted)
• 密度：
  1.90

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2935009090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride	1185262-93-4	C6H7ClN6O2S	262.68
  四唑嘧磺隆	azimsulfuron	120162-55-2	C13H16N10O5S	424.4
  ——	5-(5-(benzylsulfanyl)-1-methyl-1H-pyrazol-4-yl)-2-methyl-2H-tetrazole	——	C13H14N6S	286.36

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  四唑嘧磺隆	azimsulfuron	120162-55-2	C13H16N10O5S	424.4

反应信息

• 作为反应物：
  描述：

  4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶 、 1-甲基-4-(2-甲基-2H-四氮唑-5-基)-1H-吡唑-5-磺酰胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到四唑嘧磺隆
  参考文献：
  名称：

  PROCESS OF PREPARATION OF AZIMSULFURON

  摘要：

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有式I的化合物， 在氯代溶剂（如二氯甲烷、1,2-二氯乙烷）中，通过在水杨酸或甲酸和氯气或次氯酸钠的存在下，用盐酸处理；或者在水环醚（如四氢呋喃、1,4-二噁烷）中，通过在水杨酸和N-氯琥珀酰亚胺或过氧化氢的存在下，用盐酸处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。

  公开号：

  US20150112063A1
• 作为产物：
  描述：

  5-氨基-1-甲基-吡唑-4-甲腈 在 盐酸 、 sodium azide 、 氨 、 氯 、 sodium hydride 、 potassium carbonate 、 氯化铵 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 4.0h， 生成 1-甲基-4-(2-甲基-2H-四氮唑-5-基)-1H-吡唑-5-磺酰胺
  参考文献：
  名称：

  [EN] PROCESS OF PREPARATION OF AZIMSULFURON
  [FR] PROCÉDÉ DE PRÉPARATION D'AZIMSULFURON

  摘要：

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有化学式I的化合物（应在此处插入化学式I）与水杨酸或甲酸和氯气或次氯酸钠在氯化溶剂（如二氯甲烷、1,2-二氯乙烷）中，在氯化溶剂中的氯化氢的存在下处理，或者与水杨酸和N-氯琥珀酰亚胺或过氧化氢在环氧乙醚（如四氢呋喃、1,4-二噁烷）中的氯化氢的存在下处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。

  公开号：

  WO2014002111A1

文献信息

• [EN] PROCESS OF PREPARATION OF AZIMSULFURON<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AZIMSULFURON
  申请人：RALLIS INDIA LTD

  公开号：WO2014002111A1

  公开（公告）日：2014-01-03

  The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, (Formula I should be inserted here.) with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有化学式I的化合物（应在此处插入化学式I）与水杨酸或甲酸和氯气或次氯酸钠在氯化溶剂（如二氯甲烷、1,2-二氯乙烷）中，在氯化溶剂中的氯化氢的存在下处理，或者与水杨酸和N-氯琥珀酰亚胺或过氧化氢在环氧乙醚（如四氢呋喃、1,4-二噁烷）中的氯化氢的存在下处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。
• PROCESS OF PREPARATION OF AZIMSULFURON
  申请人：Rallis India Limited

  公开号：US20150112063A1

  公开（公告）日：2015-04-23

  The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有式I的化合物， 在氯代溶剂（如二氯甲烷、1,2-二氯乙烷）中，通过在水杨酸或甲酸和氯气或次氯酸钠的存在下，用盐酸处理；或者在水环醚（如四氢呋喃、1,4-二噁烷）中，通过在水杨酸和N-氯琥珀酰亚胺或过氧化氢的存在下，用盐酸处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。
• Kinetic study on acid-base catalyzed hydrolysis of azimsulfuron, a sulfonylurea herbicide
  作者：M. Niyaz Khan、Baki B. Bakar、Fenny W. N. Yin

  DOI：10.1002/(sici)1097-4601(1999)31:4<253::aid-kin2>3.0.co;2-x

  日期：——

  Pseudo-first-order rate constants (k(obs)) for hydrolysis of a sulfonylurea herbicide, azimsulfuron, AZIM(R), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbony]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazoie-5-sulfonamide} (AZS) follow an empirical relationship: k(obs) = alpha(1) + alpha(2)[-OH] + alpha(3)[-OH](2) within the [NaOH] range of 0.1-20 M at different temperatures ranging from 40 to 55 degrees C. The contribution of alpha(3)[-OH](2) term is small compared with alpha(2)[-OH] term and this turns out to be zero at 60 degrees C. Pseudo-first-order rate constants (k(obs)) for hydrolysis of AZS within the [H+] range from 2.5 X 10(-6) to 1.4 M follow the relationship: k(obs) = (alpha(1)K(a) + beta(1)[H+] + beta(2)[H+](2))/([H+] + K-a) where pK(a) = 4.37 at 50 degrees C, The value of beta(1) is nearly 25 times larger than that of alpha(1). The rate of alkaline hydrolysis of AZIM is weakly sensitive to ionic strength. (C) 1999 John Wiley & Sons, Inc.
• Structural Elucidation of Phototransformation Products of Azimsulfuron in Water
  作者：M. Vittoria Pinna、Michele Zema、Carlo Gessa、Alba Pusino

  DOI：10.1021/jf070897k

  日期：2007.8.1

  The photodegradation of the sulfonylurea herbicide azimsulfuron, N-[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (AZS), was studied in water at different wavelengths and in the presence of photocatalysts. AZS was rapidly degraded by UV light, affording three photoproducts. The main product, accounting for about 70% of photodegraded herbicide, was identified as 6-amino-5-[(4,6-dimethoxypyrimidin-2-yl)methylamino]-1,5,6,8-tetrahydro-7-oxa-8 lambda(6)-tia-1,2,5,6-tetraza-azulen-4-one (ADTA) by single-crystal X-ray diffraction. With simulated sunlight irradiation, the reaction was slower and 2-amino-4,6-dimethoxypyrimidine (DPA) and 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (MPS), arising from a photohydrolytic cleavage of the sulfonylurea bridge, were the only byproducts observed. The reactions followed first-order kinetics. The addition of dissolved organic matter (DOM) did not modify significantly the AZS photodegradation rate. The presence of Fe2O3 accelerated more than twice the reaction rate affording two major products, DPA and MPS, together with minor amounts of N-[[(5-hydroxy-4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide (AZS-OH). The greatest degradation rate was detected in the presence of TiO2. Only the photohydroxylation product AZS-OH was observed, which was transformed rapidly into oxalic acid.
• Sorption and Degradation of Azimsulfuron on Iron(III)-Rich Soil Colloids
  作者：M. Vittoria Pinna、Alba Pusino、Carlo Gessa

  DOI：10.1021/jf048722n

  日期：2004.12.1

  The sorption of N-[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazole5-yl)1H-pyrazole-5-sulfonamide (AZS) on an iron oxide, iron(Ill)-humate, and an Fe3+-saturated clay was studied using a batch equilibrium method. Generally, 20 mg of each colloid was equilibrated with 20 mL of AZS solution (1.5-12.7 muM). The sorption on iron-montmorillonite and iron oxide was rapid, and the equilibrium was attained within 1.5 and 5 h, respectively. In the case of Fe-saturated humic acid the equilibrium time was 20 h. After equilibration, the phases were centrifuged (19000g, 15 min) and the supernatant was sampled and analyzed by HPLC. The values of Freundlich constants indicate that iron oxide (K-ads = 199.5) shows the highest sorptive capacity toward AZS, followed by iron(III)-clay (K-ads = 146.6) and iron(III)-humate (K-ads = 108.2). With elapsing time, AZS degradation was observed in all colloidal suspensions. Iron-humate (t(1/2) = 136 h) is most effective in promoting AZS degradation, followed by iron oxide (t(1/2) = 204 h) and iron-clay (t(1/2) = 385 h). The metabolites 2-amino-4,6-dimethoxypyrimidine and 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)-1H-pyrazole-5-sulfonamide, arising from a hydrolytic cleavage of the sulfonylurea bridge, were the only byproducts observed. A Fourier transform infrared study suggests that the sorption of AZS on iron-clay involves the protonation of one of the two basic pyrimidine nitrogens induced by the acidic water surrounding the saturating Fe3+ ions. Instead, the formation of a six-membered chelated complex favors the sorption of AZS on iron oxide.