咪唑磺隆 | 122548-33-8

• 物质功能分类: 化学农药原药 - 除草剂 - 取代脲类除草剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 咪唑磺隆
• 中文别名: 2-氯-N-(((4,6-二甲氧基-2-嘧啶基)氨基)甲酰)咪唑并[1,2-a]吡啶-3-磺酰胺；1-(2-氯咪唑[1,2-A]吡啶-3-甲基磺酰基)-3-(4,6-二甲嘧啶-2)尿素；1-(2-氯咪唑并[1,2-Α]吡啶-3-基磺酰基)-3-(4,6-二甲氧基嘧啶2-基)脲；唑吡嘧磺隆
• 英文名称: imazosulfuron
• 英文别名: 1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea；2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]carbonyl]imidazo[1,2-a]pyridine-3-sulfonamide；N-(2-Chloroimidazo[1,2-a]pyridine-3-ylsulfonyl)-N'-(4,6-dimethoxy-2-pyrimidinyl)urea；1-(2-chloroimidazo[1,2-a]pyridin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea
• CAS: 122548-33-8
• 化学式: C₁₄H₁₃ClN₆O₅S
• 分子量: 412.813
• InChiKey: NAGRVUXEKKZNHT-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184° (dec)
• 密度：
  d25 1.574
• 颜色/状态：
  White, crystalline powder
• 溶解度：
  In water (mg/L at 25 °C), 5 (pH 5.1), 67 (pH 6.1), 308 (pH 7)
• 蒸汽压力：
  3.38X10-10 mm Hg at 25 °C
• 稳定性/保质期：
  Stable under recommended storage conditions.
• 解离常数：
  pKa = 3.94 in methanol/0.01 M citrate buffer at 252 nm

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  8

ADMET

代谢

在这项研究中使用了两种测试物质：1. [im-(14)C]imazosulfuon，比活性为2.15 Gbq/mmol，放射化学纯度> 99.0%，与未标记的imazosulfuron（纯度为98.6%）混合；2. [pm-(14)C]imazosulfuon，比活性为2.04 Gbq/mmol，放射化学纯度> 98.6%，与未标记的imazosulfuron（纯度为98.6%）混合。每种测试物质都悬浮在超纯水中的0.5%羧甲基纤维素中，并以单次灌胃的方式给予每性别1只Crl:CD (SD)大鼠。给予测试物质后，(14)C呼出气体的排泄可以忽略不计。在给药后1、2和3天收集粪便和尿液样本。对于 [im-(14)C]imazosulfuon，72小时后，雄性有65.3%，雌性有69.0%的放射性剂量通过尿液排出，雄性有36.8%，雌性有31.8%的放射性剂量通过粪便排出。对于 [pm-(14)C]imazosulfuon，72小时后，雄性有64.4%，雌性有57.9%的放射性剂量通过尿液排出，雄性有37.2%，雌性有40.1%的放射性剂量通过粪便排出。[im-(14)C]imazosulfuon 和 [pm-(14)C]imazosulfuon 都被广泛代谢。对于 [im-(14)C]imazosulfuon，24小时后，代谢物HMS（雄性剂量的54.6%，雌性剂量的58.2%）和IHDU（雄性剂量的2.7%，雌性剂量的4.3%）通过尿液排出，48小时后，代谢物HMS（雄性剂量的6.9%，雌性剂量的5.6%）、IHDU（雄性剂量的0.8%，雌性剂量的0.3%）和ACIS（雄性剂量的6.0%，雌性剂量的4.3%）通过粪便排出。对于 [pm-(14)C]imazosulfuon，24小时后，代谢物HMS（雄性剂量的50.3%，雌性剂量的47.8%）和IHDU（雄性剂量的5.1%，雌性剂量的3.1%）通过尿液排出，48小时后，代谢物HMS（雄性剂量的5.3%，雌性剂量的13.4%）、IHDU（雄性剂量的0.7%，雌性剂量的0.5%）和UK-1（雄性剂量的3.8%，雌性剂量的4.0%）通过粪便排出。从已识别的代谢物中，代谢反应被确定为脱甲基、嘧啶环的羟基化、嘧啶环的开环以及磺酰脲桥的水解。

Two test articles were used in this study: 1. [im-(14)C]imazosulfuon, specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0% together with unlabeled imazosulfuron, purity = 98.6% and 2. [pm-(14)C]imazosulfuon, specific activity 2.04 Gbq/mmol, radiochemical purity> 98.6% together with unlabeled imazosulfuron, purity = 98.6%, each of which was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 1 Crl:CD (SD) rat per sex. (14)C excretion into the expired air was negligible. Fecal and urine samples were collected at 1, 2, and 3 days after the administration of the dosing compounds. For [im-(14)C]imazosulfuon, 65.3% (male) and 69.0% (female) of radio-labeled dose was eliminated in the urine and 36.8% (male) and 31.8% (female) of the radio-labeled dose was eliminated in the feces 72 hours after dosing. For [pm- (14)C]imazosulfuon, 64.4% (male) and 57.9% (female) of radio-labeled dose was eliminated in the urine and 37.2% (male) and 40.1% (female) of the radio-labeled dose was eliminated in the feces 72 hours after dosing. Both [im-(14)C]imazosulfuon and [pm-(14)C]imazosulfuon were extensively metabolized. For [im-(14)C]imazosulfuon, metabolites HMS (54.6% of the dose in the male and 58.2% of the dose in the female) and IHDU (2.7% of the dose in the male and 4.3% of the dose in the female) were excreted in the urine 24 hours after dosing and metabolites HMS (6.9% of the dose in the male and 5.6% of the dose in the female), IHDU (0.8% of the dose in male and 0.3% of the dose in female), and ACIS (6.0% of the dose in the male and 4.3% of the dose in the female) were excreted in the feces 48 hours after dosing. For [pm-(14)C]imazosulfuon, metabolites HMS (50.3% of the dose in the male and 47.8% of the dose in the female) and IHDU (5.1% of the dose in the male and 3.1% of the dose in the female) were excreted in the urine 24 hours after dosing and metabolites HMS (5.3% of the dose in the male and 13.4% of the dose in the female), IHDU (0.7% of the dose in the male and 0.5% of the dose in the female), and UK-1 (3.8% of the dose in the male and 4.0% of the dose in the female) were excreted in the feces 48 hours after dosing. From the identified metabolites, metabolic reactions were determined to be demethylation, hydroxylation of the pyrimidine ring, opening of the pyrimidine ring, and hydrolysis of the sulfonylurea bridge.

来源:Hazardous Substances Data Bank (HSDB)

代谢

[14C]咪唑磺隆（比活度2.15 Gbq/mmol，放射性纯度> 99.0%）与未标记的咪唑磺隆（纯度= 98.6%）悬浮在超纯水中的0.5%羧甲基纤维素中，并通过单次灌胃给予4只雄性Crl:CD (SD)大鼠。在给药后6和12小时（仅尿液），以及24、48和72天收集粪便和尿液样本。72小时后，64.1%的放射性标记剂量通过尿液排出，32.4%的放射性标记剂量通过粪便排出。放射性标记剂量在尸体（0.15%）、血液（0.04%）和肝脏（0.04%）中的平均组织浓度最高。[imidazopyridinyl-3-(14)C]咪唑磺隆被广泛代谢。代谢物HMS（55.7%的剂量）、IHDU（4.1%的剂量）和HDS（1.9%的剂量）在给药后48小时通过尿液排出。代谢物HMS（6.5%的剂量）、IHDU（0.4%的剂量）、HDS（2.3%的剂量）、IPSN（2.9%的剂量，来自提取物1和3）和ACIS（3.2%的剂量，来自提取物1和3）在给药后48小时通过粪便排出。从已识别的代谢物中，代谢反应被确定为去甲基化、羟基化、羟基甲基化、嘧啶环的开环和磺酰脲桥的水解。

[im- (14)C]imazosulfuron (specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0%) together with unlabeled imazosulfuron (purity = 98.6%) was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 4 male Crl:CD (SD) rats. Fecal and urine samples were collected at 6 and 12 hours (urine only), and 24, 48, and 72 days after the administration. 64.1% of radio-labeled dose was eliminated in the urine and 32.4% of the radio-labeled dose was eliminated in the feces 72 hours after dosing. The highest mean tissue concentrations of the radio-labeled dose were found in the carcass (0.15%), blood (0.04%), and liver (0.04%). [Imidazopyridinyl-3-(14)C] Imazosulfuron was extensively metabolized. Metabolites HMS (55.7% of the dose), IHDU (4.1% of the dose), and HDS (1.9% of the dose) were excreted in the urine 48 hours after dosing. Metabolites HMS (6.5% of the dose), IHDU (0.4% of the dose), HDS (2.3% of the dose), IPSN (2.9% of the dose, from extracts 1 and 3), and ACIS (3.2% of the dose from extracts 1 and 3) were excreted in the feces 48 hours after dosing. From the identified metabolites, metabolic reactions were determined to be demethylation, hydroxylation, methylation of the hydroxyl group, opening of the pyrimidine ring, and hydrolysis of the sulfonylurea bridge.

来源:Hazardous Substances Data Bank (HSDB)

代谢

[14C]Imazosulfuron（具体活性为2.15 Gbq/mmol，放射性纯度> 99.0%）与未标记的imazosulfuron（纯度为98.6%）悬浮在超纯水中的0.5%羧甲基纤维素中，并通过灌胃单次给药给3只胆管插管的雄性Crl:CD（SD）大鼠。在给药后6小时和12小时（仅尿液和胆汁），以及24、48和72小时收集粪便、胆汁和尿液样本。给药后12小时，53.4%和30.5%的放射性标记剂量分别通过尿液和胆汁排出，给药后24小时，66.0%、33.8%和1.9%的放射性标记剂量分别通过尿液、胆汁和粪便排出。72小时后，66.4%、34.0%、2.4%和0.3%的放射性标记剂量分别在尿液、胆汁、粪便和残留尸体中找到。[imidazopyridinyl-3-(14)C] Imazosulfuron被广泛代谢。代谢物HMS（剂量的56.9%）、IHDU（剂量的4.9%）和HDS（剂量的0.5%）在给药后24小时通过尿液排出。代谢物HMS（剂量的3.8%）、IHDU-glu（剂量的5.2%）、HDS（剂量的1.6%）和ACIS（剂量的1.1%）在给药后24小时通过胆汁排出。代谢物HMS（剂量的0.8%）在给药后24小时通过粪便排出。从已识别的代谢物中，确定的代谢反应包括脱甲基、嘧啶环的羟基化、羟基甲基化或葡萄糖苷酸化以及嘧啶环的开环和胍基的形成。

[im-(14)C]Imazosulfuron (specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0%) together with unlabeled imazosulfuron (purity = 98.6%) was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 3 bile duct-cannulated male Crl:CD (SD) rats. Feces, bile, and urine samples were collected at 6 and 12 hours (urine and bile only), and 24, 48, and 72 hours after the administration of the dosing material. 53.4% and 30.5% of the radio-labeled dose was eliminated in the urine and bile, respectively, 12 hours after dosing and 66.0%, 33.8%, and 1.9% of the radio-labeled dose was eliminated in the urine, bile, and feces, respectively, 24 hours after dosing. After 72 hours, 66.4%, 34.0%, 2.4%, and 0.3% of the of the radio-labeled dose had been found in the urine, bile, feces, and residual carcass, respectively. [Imidazopyridinyl-3-(14)C] Imazosulfuron was extensively metabolized. Metabolites HMS (56.9% of the dose), IHDU (4.9% of the dose), and HDS (0.5% of the dose) were excreted in the urine 24 hours after dosing. Metabolites HMS (3.8% of the dose), IHDU-glu (5.2% of the dose), HDS (1.6% of the dose), and ACIS (1.1% of the dose) were excreted in the bile 24 hours after dosing. Metabolite HMS (0.8% of the dose) was excreted in the feces 24 hours after dosing. From the identified metabolites, metabolic reactions determined to have occurred were demethylation, hydroxylation of the pyrimidine ring, methylation or glucuronidation of hydroxyl group, and opening of the pyrimidine ring and formation of guanidine.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：敌草隆是一种除草剂，用于控制稻田和草坪上的大多数一年生和多年生阔叶杂草和莎草。人体研究：在一例报告中，摄入敌草隆和美芬净几乎立即改变了尿液的颜色变为绿色。动物研究：在小鼠中，观察到在雄性10,000和45,000 ppm以及雌性45,000 ppm时，与处理相关的平均相对肝重增加。在处理24个月的大鼠中，眼睛检查显示在雄性在终止时（24个月）和雌性在6个月（仅白内障）、12个月和18个月时，20,000 ppm的处理相关视网膜退行性和后囊下或完全白内障。显微镜检查显示在20,000 ppm时，两性均出现双侧视网膜萎缩，雌性在20,000 ppm时出现双侧晶状体白内障。组织病理学检查未发现与处理相关的肿瘤。在大鼠的F0和F1代中，观察到10,000 ppm处理相关的平均活产仔数减少。未观察到与处理相关的胎儿畸形或发育变异。在没有代谢激活的情况下培养的中国仓鼠肺成纤维细胞中，在500 ug/mL时观察到染色单体断裂和染色单体交换的增加。

IDENTIFICATION AND USE: Imazosulfuron is a herbicide, which is used to control most annual and perennial broad-leaved weeds and sedges in paddy rice and turf. HUMAN STUDIES: In a case report, ingestion of imazosulfuron and mefenacet changed urine color to green almost immediately. ANIMAL STUDIES: In mice, treatment-related increase in the mean relative liver weight was observed in males at 10,000 and 45,000 ppm and in females at 45,000 ppm. In rats treated for 24 months, examination of the eyes revealed treatment-related retinal degeneration and posterior subcapsular or complete cataracts at 20,000 ppm in males at termination (24 months) and in females at 6 months (cataracts only), 12 months, and 18 months. Microscopic examination revealed bilateral retinal atrophy in both sexes at 20,000 ppm and bilateral lens cataracts in females at 20,000 ppm. Histopathological examination revealed no treatment-related neoplasms. A treatment-related decrease in mean live litter size in both F0 and F1 generations was observed at 10,000 ppm in rats. No treatment-related fetal malformations or developmental variations were observed. An increase in chromatid breaks and chromatid exchanges were observed at 500 ug/mL in cells cultured without metabolic activation in cultures of Chinese hamster lung fibroblasts.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入性肺炎。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽插管以控制气道。使用带气囊的面罩进行正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水（D5W），保持通道开放，最小流量/ SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%盐水（NS）或乳酸林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮（安定）或劳拉西泮（安泰伦）治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒物A和B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

病例报告/ 尿液颜色改变可能有多种可能的原因。在这里，我们介绍了一位76岁女性因摄入无机除草剂咪草烟和甲氧磺隆后的病例。她的尿液颜色几乎立即变为绿色。由于患者没有特定的药物或医疗史，我们认为尿液颜色改变的最可能原因是除草剂的摄入。对尿液进行了光谱光度分析，在波长光谱的绿色区域观察到一个峰值。这些发现表明，在绿色尿液颜色改变的鉴别诊断中应考虑咪草烟和甲氧磺隆。

/CASE REPORTS/ The development of discolored urine may have many possible causes. Here we present the case of a 76-year-old woman who was admitted after ingesting the inorganic herbicides, mefenacet and imazosulfuron. Her urine color changed to green almost immediately. Since the patient had no specific medication or medical history we considered that the most likely cause of the change in urine color was the ingestion of the herbicides. Spectrophotometric analysis of the urine was conducted and a peak was observed in the green area of the wavelength spectrum. These findings show that mefenacet and imazosulfuron should be considered in the differential diagnosis of green discolored urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在这项研究中使用了两种测试物质：1. [im-(14)C]imazosulfuon，比活度为2.15 Gbq/mmol，放射化学纯度> 99.0%，与未标记的imazosulfuron（纯度为98.6%）混合；2. [pm-(14)C]imazosulfuon，比活度为2.04 Gbq/mmol，放射化学纯度> 98.6%，与未标记的imazosulfuron（纯度为98.6%）混合。每种物质都悬浮在超纯水中的0.5%羧甲基纤维素中，并通过灌胃的方式一次性给予每性别1只Crl:CD (SD)大鼠。给予放射性标记物质后，呼出气体中的(14)C排泄可以忽略不计。在给药后1、2和3天收集粪便和尿液样本。对于[im-(14)C]imazosulfuon，给药72小时后，65.3%（雄性）和69.0%（雌性）的放射性标记剂量通过尿液排出，36.8%（雄性）和31.8%（雌性）的放射性标记剂量通过粪便排出。对于[pm-(14)C]imazosulfuon，给药72小时后，64.4%（雄性）和57.9%（雌性）的放射性标记剂量通过尿液排出，37.2%（雄性）和40.1%（雌性）的放射性标记剂量通过粪便排出。[im-(14)C]imazosulfuon和[pm-(14)C]imazosulfuon都广泛代谢。对于[im-(14)C]imazosulfuon，代谢物HMS（雄性剂量的54.6%，雌性剂量的58.2%）和IHDU（雄性剂量的2.7%，雌性剂量的4.3%）在给药后24小时内通过尿液排出，代谢物HMS（雄性剂量的6.9%，雌性剂量的5.6%）、IHDU（雄性剂量的0.8%，雌性剂量的0.3%）和ACIS（雄性剂量的6.0%，雌性剂量的4.3%）在给药后48小时内通过粪便排出。对于[pm-(14)C]imazosulfuon，代谢物HMS（雄性剂量的50.3%，雌性剂量的47.8%）和IHDU（雄性剂量的5.1%，雌性剂量的3.1%）在给药后24小时内通过尿液排出，代谢物HMS（雄性剂量的5.3%，雌性剂量的13.4%）、IHDU（雄性剂量的0.7%，雌性剂量的0.5%）和UK-1（雄性剂量的3.8%，雌性剂量的4.0%）在给药后48小时内通过粪便排出。从已鉴定的代谢物中，确定代谢反应为去甲基化、嘧啶环的羟基化、嘧啶环的开环和磺酰脲桥的水解。

Two test articles were used in this study: 1. [im-(14)C]imazosulfuon, specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0% together with unlabeled imazosulfuron, purity = 98.6% and 2. [pm-(14)C]imazosulfuon, specific activity 2.04 Gbq/mmol, radiochemical purity> 98.6% together with unlabeled imazosulfuron, purity = 98.6%, each of which was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 1 Crl:CD (SD) rat per sex. (14)C excretion into the expired air was negligible. Fecal and urine samples were collected at 1, 2, and 3 days after the administration of the dosing compounds. For [im-(14)C]imazosulfuon, 65.3% (male) and 69.0% (female) of radio-labeled dose was eliminated in the urine and 36.8% (male) and 31.8% (female) of the radio-labeled dose was eliminated in the feces 72 hours after dosing. For [pm- (14)C]imazosulfuon, 64.4% (male) and 57.9% (female) of radio-labeled dose was eliminated in the urine and 37.2% (male) and 40.1% (female) of the radio-labeled dose was eliminated in the feces 72 hours after dosing. Both [im-(14)C]imazosulfuon and [pm-(14)C]imazosulfuon were extensively metabolized. For [im-(14)C]imazosulfuon, metabolites HMS (54.6% of the dose in the male and 58.2% of the dose in the female) and IHDU (2.7% of the dose in the male and 4.3% of the dose in the female) were excreted in the urine 24 hours after dosing and metabolites HMS (6.9% of the dose in the male and 5.6% of the dose in the female), IHDU (0.8% of the dose in male and 0.3% of the dose in female), and ACIS (6.0% of the dose in the male and 4.3% of the dose in the female) were excreted in the feces 48 hours after dosing. For [pm-(14)C]imazosulfuon, metabolites HMS (50.3% of the dose in the male and 47.8% of the dose in the female) and IHDU (5.1% of the dose in the male and 3.1% of the dose in the female) were excreted in the urine 24 hours after dosing and metabolites HMS (5.3% of the dose in the male and 13.4% of the dose in the female), IHDU (0.7% of the dose in the male and 0.5% of the dose in the female), and UK-1 (3.8% of the dose in the male and 4.0% of the dose in the female) were excreted in the feces 48 hours after dosing. From the identified metabolites, metabolic reactions were determined to be demethylation, hydroxylation of the pyrimidine ring, opening of the pyrimidine ring, and hydrolysis of the sulfonylurea bridge.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

[14C]Imazosulfuron（比活度2.15 Gbq/mmol，放射性纯度> 99.0%）与未标记的Imazosulfuron（纯度= 98.6%）悬浮在超纯水中的0.5%羧甲基纤维素中，并通过单次灌胃给予4只雄性Crl:CD（SD）大鼠。在给药后6小时和12小时（仅尿液），以及24、48和72小时收集粪便和尿液样本。64.1%的放射性标记剂量通过尿液排出，72小时后32.4%的放射性标记剂量通过粪便排出。放射性标记剂量在尸体（0.15%）、血液（0.04%）和肝脏（0.04%）中的平均组织浓度最高。[imidazopyridinyl-3-(14)C] Imazosulfuron被广泛代谢。代谢物HMS（55.7%的剂量）、IHDU（4.1%的剂量）和HDS（1.9%的剂量）在给药后48小时通过尿液排出。代谢物HMS（6.5%的剂量）、IHDU（0.4%的剂量）、HDS（2.3%的剂量）、IPSN（2.9%的剂量，来自提取物1和3）和ACIS（3.2%的剂量，来自提取物1和3）在给药后48小时通过粪便排出。从已识别的代谢物中，代谢反应被确定为脱甲基、羟基化、羟基甲基化、嘧啶环开环和磺酰脲桥的水解。

[im-(14)C]Imazosulfuron (specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0%) together with unlabeled imazosulfuron (purity = 98.6%) was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 4 male Crl:CD (SD) rats. Fecal and urine samples were collected at 6 and 12 hours (urine only), and 24, 48, and 72 hours after the administration. 64.1% of radio-labeled dose was eliminated in the urine and 32.4% of the radio-labeled dose was eliminated in the feces 72 hours after dosing. The highest mean tissue concentrations of the radio-labeled dose were found in the carcass (0.15%), blood (0.04%), and liver (0.04%). [Imidazopyridinyl-3-(14)C] Imazosulfuron was extensively metabolized. Metabolites HMS (55.7% of the dose), IHDU (4.1% of the dose), and HDS (1.9% of the dose) were excreted in the urine 48 hours after dosing. Metabolites HMS (6.5% of the dose), IHDU (0.4% of the dose), HDS (2.3% of the dose), IPSN (2.9% of the dose, from extracts 1 and 3), and ACIS (3.2% of the dose from extracts 1 and 3) were excreted in the feces 48 hours after dosing. From the identified metabolites, metabolic reactions were determined to be demethylation, hydroxylation, methylation of the hydroxyl group, opening of the pyrimidine ring, and hydrolysis of the sulfonylurea bridge.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

[14C]咪唑磺隆（比活度2.15 Gbq/mmol，放射化学纯度> 99.0%）与未标记的咪唑磺隆（纯度= 98.6%）一起悬浮在超纯水中的0.5%羧甲基纤维素中，并以单次剂量通过灌胃给药给3只胆管插管的Crl:CD（SD）雄性大鼠。在给药后6小时和12小时（仅尿液和胆汁），以及24、48和72天收集粪便、胆汁和尿液样本。给药后12小时，53.4%和30.5%的放射性标记剂量分别通过尿液和胆汁排出，给药后24小时，66.0%、33.8%和1.9%的放射性标记剂量分别通过尿液、胆汁和粪便排出。72小时后，66.4%、34.0%、2.4%和0.3%的放射性标记剂量分别在尿液、胆汁、粪便和残留尸体中发现。[咪唑并吡啶基-3-(14)C]咪唑磺隆被广泛代谢。代谢物HMS（剂量的56.9%）、IHDU（剂量的4.9%）和HDS（剂量的0.5%）在给药后24小时通过尿液排出。代谢物HMS（剂量的3.8%）、IHDU-glu（剂量的5.2%）、HDS（剂量的1.6%）和ACIS（剂量的1.1%）在给药后24小时通过胆汁排出。代谢物HMS（剂量的0.8%）在给药后24小时通过粪便排出。从已识别的代谢物中，确定的代谢反应包括脱甲基化、嘧啶环的羟基化、羟基组的甲基化或葡萄糖醛酸化，以及嘧啶环的开环和胍基的形成。

[im-(14)C]Imazosulfuron (specific activity 2.15 Gbq/mmol, radiochemical purity> 99.0%) together with unlabeled imazosulfuron (purity = 98.6%) was suspended in 0.5% carboxymethyl cellulose in ultrapure water and administered in a single dose by gavage to 3 bile duct-cannulated male Crl:CD (SD) rats. Feces, bile, and urine samples were collected at 6 and 12 hours (urine and bile only), and 24, 48, and 72 days after the administration of the dosing material. 53.4% and 30.5% of the radio-labeled dose was eliminated in the urine and bile, respectively, 12 hours after dosing and 66.0%, 33.8%, and 1.9% of the radio-labeled dose was eliminated in the urine, bile, and feces, respectively, 24 hours after dosing. After 72 hours, 66.4%, 34.0%, 2.4%, and 0.3% of the of the radio-labeled dose had been found in the urine, bile, feces, and residual carcass, respectively. [Imidazopyridinyl-3-(14)C] Imazosulfuron was extensively metabolized. Metabolites HMS (56.9% of the dose), IHDU (4.9% of the dose), and HDS (0.5% of the dose) were excreted in the urine 24 hours after dosing. Metabolites HMS (3.8% of the dose), IHDU-glu (5.2% of the dose), HDS (1.6% of the dose), and ACIS (1.1% of the dose) were excreted in the bile 24 hours after dosing. Metabolite HMS (0.8% of the dose) was excreted in the feces 24 hours after dosing. From the identified metabolites, metabolic reactions determined to have occurred were demethylation, hydroxylation of the pyrimidine ring, methylation or glucuronidation of hydroxyl group, and opening of the pyrimidine ring and formation of guanidine.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• WGK Germany：
  1
• 海关编码：
  29350090

SDS

1.1 产品标识符
: 咪唑磺隆
产品名称
1.2 鉴别的其他方法
1-(2-Chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea
1.3 有关的确定了的物质或混合物的用途和建议不适合的用途
仅供科研用途，不作为药物、家庭备用药或其它用途。

---

模块 2. 危险性概述
2.1 GHS分类
根据化学品全球统一分类与标签制度(GHS)的规定，不是危险物质或混合物。
当心 - 物质尚未完全测试。
2.3 其它危害物 - 无

---

模块 3. 成分/组成信息
3.1 物 质
: 1-(2-Chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-
别名
2-yl)urea
: C14H13ClN6O5S
分子式
: 412.81 g/mol
分子量
无

---

模块 4. 急救措施
4.1 必要的急救措施描述
吸入
如果吸入,请将患者移到新鲜空气处。 如果停止了呼吸,给于人工呼吸。
皮肤接触
用肥皂和大量的水冲洗。
眼睛接触
用水冲洗眼睛作为预防措施。
食入
切勿给失去知觉者从嘴里喂食任何东西。 用水漱口。
4.2 主要症状和影响，急性和迟发效应
据我们所知，此化学，物理和毒性性质尚未经完整的研究。
4.3 及时的医疗处理和所需的特殊处理的说明和指示
无数据资料

---

模块 5. 消防措施
5.1 灭火介质
灭火方法及灭火剂
用水雾,耐醇泡沫,干粉或二氧化碳灭火。
5.2 源于此物质或混合物的特别的危害
碳氧化物, 氯化氢气体, 氮氧化物, 硫氧化物
碳氧化物, 氮氧化物, 硫氧化物, 氯化氢气体
5.3 给消防员的建议
如必要的话,戴自给式呼吸器去救火。
5.4 进一步信息
无数据资料

---

模块 6. 泄露应急处理
6.1 人员的预防,防护设备和紧急处理程序
防止粉尘的生成。 防止吸入蒸汽、气雾或气体。
6.2 环境保护措施
不要让产物进入下水道。
6.3 抑制和清除溢出物的方法和材料
扫掉和铲掉。 存放进适当的闭口容器中待处理。
6.4 参考其他部分
丢弃处理请参阅第13节。

---

模块 7. 操作处置与储存
7.1 安全操作的注意事项
在有粉尘生成的地方,提供合适的排风设备。一般性的防火保护措施。
7.2 安全储存的条件,包括任何不兼容性
贮存在阴凉处。 容器保持紧闭，储存在干燥通风处。
7.3 特定用途
无数据资料

---

模块 8. 接触控制和个体防护
8.1 容许浓度
最高容许浓度
没有已知的国家规定的暴露极限。
8.2 暴露控制
适当的技术控制
常规的工业卫生操作。
个体防护设备
眼/面保护
请使用经官方标准如NIOSH (美国) 或 EN 166(欧盟) 检测与批准的设备防护眼部。
皮肤保护
戴手套取 手套在使用前必须受检查。
请使用合适的方法脱除手套(不要接触手套外部表面),避免任何皮肤部位接触此产品.
使用后请将被污染过的手套根据相关法律法规和有效的实验室规章程序谨慎处理. 请清洗并吹干双手
所选择的保护手套必须符合EU的89/686/EEC规定和从它衍生出来的EN 376标准。
身体保护
根据危险物质的类型，浓度和量，以及特定的工作场所来选择人体保护措施。,
防护设备的类型必须根据特定工作场所中的危险物的浓度和含量来选择。
呼吸系统防护
不需要保护呼吸。如需防护粉尘损害，请使用N95型（US）或P1型（EN 143)防尘面具。
呼吸器使用经过测试并通过政府标准如NIOSH（US）或CEN（EU）的呼吸器和零件。

---

模块 9. 理化特性
9.1 基本的理化特性的信息
a) 外观与性状
形状: 结晶, 粉末
颜色: 白色
b) 气味
无数据资料
c) 气味阈值
无数据资料
d) pH值
无数据资料
e) 熔点/凝固点
183 - 184 °C
f) 起始沸点和沸程
无数据资料
g) 闪点
无数据资料
h) 蒸发速率
无数据资料
i) 易燃性(固体,气体)
无数据资料
j) 高的/低的燃烧性或爆炸性限度 无数据资料
k) 蒸汽压
无数据资料
l) 蒸汽密度
无数据资料
m) 相对密度
1.574 g/cm3 在 25.5 °C
n) 水溶性
0.007 g/l 在 25 °C
o) n-辛醇/水分配系数
辛醇--水的分配系数的对数值: 0.049 在 25 °C
p) 自燃温度
无数据资料
q) 分解温度
无数据资料
r) 粘度
无数据资料

---

模块 10. 稳定性和反应活性
10.1 反应性
无数据资料
10.2 稳定性
无数据资料
10.3 危险反应的可能性
无数据资料
10.4 应避免的条件
无数据资料
10.5 不兼容的材料
强氧化剂
10.6 危险的分解产物
其它分解产物 - 无数据资料

---

模块 11. 毒理学资料
11.1 毒理学影响的信息
急性毒性
半数致死剂量 (LD50) 经口 - 大鼠 - > 5,000 mg/kg
半数致死剂量 (LD50) 经口 - 老鼠 - > 5,000 mg/kg
半数致死浓度（LC50） 吸入 - 大鼠 - 4 h - > 2.4 mg/l
皮肤刺激或腐蚀
眼睛刺激或腐蚀
无眼睛刺激
无数据资料
呼吸道或皮肤过敏
豚鼠 - 未引起试验动物过敏。
生殖细胞突变性
动物试验中未见致癌,诱变或畸变影响。 在 Ames的诱发活性试剂中无诱变现象。
致癌性
IARC:
此产品中没有大于或等于 0。1%含量的组分被 IARC鉴别为可能的或肯定的人类致癌物。
生殖毒性
无数据资料
特异性靶器官系统毒性（一次接触）
无数据资料
特异性靶器官系统毒性（反复接触）
无数据资料
吸入危险
无数据资料
潜在的健康影响
吸入 吸入可能有害。 可能引起呼吸道刺激。
摄入 如服入是有害的。
皮肤 如果通过皮肤吸收可能是有害的。 可能引起皮肤刺激。
眼睛 可能引起眼睛刺激。
接触后的征兆和症状
据我们所知，此化学，物理和毒性性质尚未经完整的研究。
附加说明
反复染毒毒性 - 大鼠 - 雄性 - 未观察到有害效果的水平 - 106.1 mg/kg
反复染毒毒性 - 大鼠 - 雌性 - 未观察到有害效果的水平 - 132.46 mg/kg
化学物质毒性作用登记: 无数据资料

---

模块 12. 生态学资料
12.1 生态毒性
对鱼类的毒性 半数致死浓度（LC50） - Carassius carassius (鲤鱼) - 250 mg/l - 96 h
对水蚤和其他水生无脊 半致死有效浓度（EC50） - 红虫 - > 100 mg/l - 48 h
椎动物的毒性
12.2 持久存留性和降解性
根据生物降解试验的结果,此产品属于不易降解的。
12.3 潜在的生物蓄积性
无数据资料
12.4 土壤中的迁移性
无数据资料
12.5 PBT 和 vPvB的结果评价
无数据资料
12.6 其它不利的影响
无数据资料

---

模块 13. 废弃处置
13.1 废物处理方法
产品
将剩余的和未回收的溶液交给处理公司。
受污染的容器和包装
作为未用过的产品弃置。

---

模块 14. 运输信息
14.1 联合国危险货物编号
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.2 联合国（UN）规定的名称
欧洲陆运危规: 非危险货物
国际海运危规: 非危险货物
国际空运危规: 非危险货物
14.3 运输危险类别
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.4 包裹组
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.5 环境危险
欧洲陆运危规: 否 国际海运危规 海运污染物: 否 国际空运危规: 否
14.6 对使用者的特别提醒
无数据资料

---

模块 16. 其他信息
进一步信息
版权所有：2012 Co. LLC. 公司。许可无限制纸张拷贝，仅限于内部使用。
上述信息视为正确，但不包含所有的信息，仅作为指引使用。本文件中的信息是基于我们目前所知，就正
确的安全提示来说适用于本品。该信息不代表对此产品性质的保证。
参见发票或包装条的反面。

---

模块 15 - 法规信息
N/A

制备方法与用途

作用机理

唑吡嘧磺隆是一种乙酰乳酸合成酶（ALS）抑制剂。它通过根部吸收后输送到整株植物中。唑吡嘧磺隆能抑制杂草顶芽生长，阻止根部和幼苗的生长发育，从而导致全株死亡。

毒性

唑吡嘧磺隆对鱼类和哺乳动物低毒。

化学性质

纯品为白色结晶，熔点183～184℃（分解），相对密度1.574（25℃），蒸气压4.52×10^-2Pa（25℃），解离常数pKa 4。25℃时在有机溶剂中的溶解度为：二氯甲烷12.8g/L，丙酮7.6g/L，乙腈2.5g/L，乙酸乙酯2.2g/L，二甲苯400mg/L；在水中溶解度分别为308mg/L（pH=7）、67mg/L（pH=6.1）、5mg/L（pH=5.1）。分配系数为0.05。

用途

唑吡嘧磺隆可通过根部吸收，然后输送到整株植物中。它能强烈抑制乙酰乳酸合成酶（ALS）这一支链氨基酸生物合成的关键酶。唑吡嘧磺隆通过抑制杂草尖芽生长，阻止根部或幼苗的生长发育，从而使杂草慢慢死亡。建议在稗草萌发前或水稻移植后10～15天使用，可以防除包括稗草在内的大多数一年生杂草及牛毛毡、萤蔺、水莎草、水芹和矮慈姑等多年生杂草。推荐使用量为30g/hm²。与其他除草剂混用可增强对稗草的防效。

生产方法

1. 2-亚氨基-1，2-二氢吡啶-1-乙酸的制备：将50.2g氯乙酸溶于80mL水和20mL乙醇中，在10～15℃下加入75mL三乙胺，并逐步加入2-氨基吡啶50g，加热至75～80℃反应5h。加100mL乙醇，冰水冷却后过滤洗涤，得产物64.6g（收率80%）。

2. 2-氯咪唑并[1，2-α]吡啶的制备：将第一步所得产品45.7g悬浮于120mL甲苯中，在105～110℃下滴加93.1g三氯氧磷，1小时滴毕，回流5h。冷却后倒入冰水中，分出有机层水层用氢氧化钠溶液中和（30～45℃），即析出固体。水洗、干燥得产物42g（收率91.7%）。

3. 2-氯咪唑并[1，2-α]吡啶-3-磺酰制备：将第二步所得产物15.3g溶于75mL二氯乙烷中，在搅拌下滴加98.5%氯磺酸14.3g，回流反应5h。冷却至20℃后，加入12.1g三乙胺，并加热回流反应3小时。冷却后注入200mL冰水中，分出有机层并负压蒸除二氯乙烷得产物24.7g（收率97.6%）。

4. 2-氯咪唑并[1，2-α]吡啶-3-磺酰的制备：将第三步所得产物溶于200mL二氯甲烷中，在20～25℃下滴加6.78g（0.0433mol）氯甲酸苯酯。继续反应30min，依次加入4.2g（0.0433mol）甲磺酸和6.72g（0.0433mol）氯甲酸苯酯以及4.2g（0.0433mol）甲磺酸和6.72g（0.0433mol）2-氨基-4，6-二甲氧基嘧啶。继续回流反应5h后减压脱溶，向残余物中加入50mL乙腈过滤洗涤得最终产物15.62g（收率87.9%）。

反应信息

• 作为产物：
  描述：

  2-氨基-4,6-二甲氧基嘧啶 、 氯磺酰异氰酸酯 生成 咪唑磺隆
  参考文献：
  名称：

  ISIDA, YASUO;OTA, KADZUNARI;NAKAXAMA, MATSUO;JOSIKAVA, XARUTOSI

  摘要：

  DOI：

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] 3-[(HYDRAZONO)METHYL]-N-(TETRAZOL-5-YL)-BENZAMIDE AND 3-[(HYDRAZONO)METHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE DERIVATIVES AS HERBICIDES<br/>[FR] DÉRIVÉS DE 3-[(HYDRAZONO))MÉTHYL]-N-(TÉTRAZOL-5-YL)-BENZAMIDE ET DE 3-[(HYDRAZONO)MÉTHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE UTILISÉS EN TANT QU'HERBICIDES
  申请人：SYNGENTA CROP PROTECTION AG

  公开号：WO2021013969A1

  公开（公告）日：2021-01-28

  The present invention related to compounds of Formula (I): or an agronomically acceptable salt thereof, wherein Q, R2, R3, R4, R5 and R6 are as described herein. The invention further relates to compositions comprising said compounds, to methods of controlling weeds using said compositions, and to the use of compounds of Formula (I) as a herbicide.

  本发明涉及以下式（I）的化合物或其农业上可接受的盐，其中Q、R2、R3、R4、R5和R6如本文所述。该发明还涉及包含所述化合物的组合物，使用这些组合物控制杂草的方法，以及将式（I）的化合物用作除草剂的用途。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] HERBICIDALLY ACTIVE HETEROARYL-S?BSTIT?TED CYCLIC DIONES OR DERIVATIVES THEREOF<br/>[FR] DIONES CYCLIQUES SUBSTITUÉES PAR HÉTÉROARYLE À ACTIVITÉ HERBICIDE OU DÉRIVÉS DE CELLES-CI
  申请人：SYNGENTA LTD

  公开号：WO2011012862A1

  公开（公告）日：2011-02-03

  The invention relates to a compound of formula (I), which is suitable for use as a herbicide wherein G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; Q is a unsubstituted or substituted C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, or Q is heteroaryl or substituted heteroaryl; m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; and wherein the compound is optionally an agronomically acceptable salt thereof.

  该发明涉及一种化合物，其化学式为(I)，适用作为除草剂，其中G为氢或农业可接受的金属、磺酸盐、铵盐或潜伏基团；Q为未取代或取代的含有至少一个来自O、N和S的杂原子的饱和或单不饱和的C3-C8杂环烷基，或Q为杂芳基或取代的杂芳基；m为1、2或3；Het为可选择地取代的单环或双环杂芳环；且该化合物可选择地为其农学上可接受的盐。
• TRIAZOLE ACC INHIBITORS AND USES THEREOF
  申请人：Gilead Apollo, LLC

  公开号：US20170166584A1

  公开（公告）日：2017-06-15

  The present invention provides triazole compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了三唑化合物，可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及其组合物和使用方法。

表征谱图