五氟磺草胺 | 219714-96-2

• 物质功能分类: 化学农药原药 - 除草剂 - 酰胺类除草剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 五氟磺草胺
• 英文名称: 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide
• 英文别名: Penoxsulam
• CAS: 219714-96-2
• 化学式: C₁₆H₁₄F₅N₅O₅S
• 分子量: 483.4
• InChiKey: SYJGKVOENHZYMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224°
• 密度：
  1.65±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）
• 颜色/状态：
  Off-white
• 气味：
  Musty
• 蒸汽压力：
  9.55X10-11 mPa /SRC: 7.2X10-16 mm Hg/ at 25 °C
• 稳定性/保质期：
  Thermally stable at typical use temperatures. /Grasp SC Herbicide/
• 分解：
  This material will not burn until the water has evaporated. Residue can burn. If exposed to fire from another source and water is evaporated, exposure to high temperatures may cause toxic fumes. /Grasp SC Herbicide/
• 解离常数：
  pKa = 5.1

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  14

ADMET

代谢

所有的给药都是通过灌胃标记的苯氧磺酰胺（XDE-638）（未标记苯氧磺酰胺的纯度为97.5%，三唑标记纯度> 99%，苯环标记纯度为98.4%）在0.5%的Methocel悬浮液中进行的。通常，每组使用4只/性别的大鼠在8个使用三唑标记的14C-XDE-638的测试中进行。另外一组4只雄性大鼠使用苯基标记的14C-XDE-638进行测试，以评估三唑和苯基部分之间的裂解程度。主要使用带有颈静脉插管的大鼠来确定单次给药后血浆、尿液和粪便中残留浓度的时间过程，给药剂量为5或250 mg/kg苯氧磺酰胺。...在各个时间间隔对汇集血浆中的主要代谢物数量进行评估，并在处死时对肝脏和肾脏组织中的代谢物进行评估。每组有3只/性别的大鼠安装了胆管插管，并在24小时内每隔一段时间收集胆汁，以评估胆汁排泄速率和代谢物分析。另外每组4只/性别的大鼠在用三唑标记的14C-XDE-638处理的第16天之前，连续15天每天给药5 mg/kg。对这些大鼠的排泄物中的残留物和组织中的代谢物水平进行了评估，发现与非预处理大鼠相当。代谢物分离是通过使用C-18固定相和足够分离大多数主要峰的梯度程序的HPLC来实现的，检测是通过UV（254 nm）和14C检测器进行的。代谢物鉴定是通过保留时间和负离子LC/MS进行的。...比较了苯基或三唑标记后尿和粪便代谢物的分布模式，表明大多数（至少90%）的苯氧磺酰胺残留物在两个标记环之间保持完整。母化合物是尿液中含量最丰富的残留物，占雄性大鼠用三唑或苯基标记的14C给药剂量的约31%和19%。...在7天收集的任何性别的大鼠中，最丰富的粪便代谢物是一种未鉴定的“代谢物Y”，在雄性大鼠中占给药剂量的14%至19%，在雌性大鼠中占6%。母本苯氧磺酰胺在雄性大鼠粪便中占给药标签的12%至15%，在雌性大鼠中占3%。...胆汁中最大的单一暂时鉴定组分是5-羟基-或8-羟基-苯氧磺酰胺的谷胱甘肽产物（占给药苯氧磺酰胺的18%）。两种羟基化苯氧磺酰胺的葡萄糖醛酸产物（两种情况下羟基化产物的位置未知）共同占据了胆汁中约15%的给药标签。

All dosing was by gavage with labeled penoxsulam (XDE-638) (97.5% purity of unlabeled penoxsulam, triazole label purity > 99%, phenyl ring label purity 98.4%) in 0.5% Methocel suspension. Generally, groups of 4 rats/sex were used in each of 8 tests using triazole-labeled 14C-XDE-638. One additional set of 4 males was tested using phenyl-labeled 14C-XDE-638 to assess the extent of cleavage between triazole and phenyl moieties. Rats fitted with jugular vein cannulae were used primarily to determine the time course of residue concentrations in plasma, urine, and feces after single dosing with either 5 or 250 mg/kg penoxsulam. ... Quantities of major metabolites were assessed in pooled plasma at various intervals, and in liver and kidney tissue at sacrifice times. Three rats/sex were fitted with bile duct cannulae, and bile was collected at intervals over 24 hr to assess biliary excretion rate and metabolite analysis. Four additional rats/sex were dosed daily for 15 days with 5 mg/kg/day prior to treatment with triazole labeled 14C-XDE-638 on day 16. These rats were evaluated for residues in excreta and for tissue levels of metabolites, which were found to be comparable to non-pre-treated rats. Metabolite separation was by HPLC using C-18 stationary phase and a gradient program sufficient to separate most major peaks for detection by UV (254 nm) and by 14C-detector. Metabolite identification was by retention time and negative ion LC/MS. ... A comparison of distribution patterns of urinary and fecal metabolites following phenyl- or triazole-label indicated that most (at least 90%) of penoxsulam residues remained intact between the two labeled rings. Parent compound was the most abundant urinary residue, constituting about 31% and 19% of administered dose in urine samples of males dosed with triazole- or phenyl-labeled 14C, respectively. ... The most abundant fecal metabolite in either sex in the 7-day collection was an uncharacterized 'Metabolite Y,' comprising 14% to 19% of administered dose in males and 6% in females. Parent penoxsulam constituted 12% to 15% of administered label in feces of males and 3% in females. ... The largest single provisionally identified component of bile was the glutathione product of 5-hydroxy- or 8-hydroxy-penoxsulam (18% of administered penoxsulam). Two glucuronide products of hydroxylated penoxsulam (position of hydroxylation product unknown in either case) appeared to account together for about 15% of administered label in bile. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，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。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。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 the 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：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的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D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。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……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：亚慢性或前慢性暴露 XDE-638（/penoxsulam/ 批号 # ND05167938，纯度 = 97.5%）混合到饲料中，以每剂量10只CD大鼠的性别进行喂养，剂量水平为0（未处理的饮食）、100、250、500或1000 mg/kg/天，连续喂养13周。没有发生死亡。在500和1000 mg/kg/天的雌性中观察到与治疗相关的红色鼻周污迹和会阴尿污迹。在1000 mg/kg/天的雌性中观察到与治疗相关的平均体重和平均饲料消耗量下降。在500和1000 mg/kg/天的两性以及雌性中观察到与治疗相关的平均相对肝重量增加，以及在500和1000 mg/kg/天的雌性中平均相对肾重量增加。宏观检查揭示了在500和1000 mg/kg/天的雌性中与治疗相关的脂肪量减少、表面粗糙的肾脏和苍白的肾脏。微观检查揭示了在500和1000 mg/kg/天的两性中与治疗相关的中心小叶肝细胞肥大，在500和1000 mg/kg/天的雌性中肾集合管和/或肾盂内出现晶体，以及在500和1000 mg/kg/天的雌性中肾小管的慢性活动性炎症，在250、500和1000 mg/kg/天的两性中肾乳头移行上皮增生。... NOEL (M/F)= 100 mg/kg/天，基于微观肾效果。

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ XDE-638 (/penoxsulam/ Lot # ND05167938, purity = 97.5%) was admixed to the feed and fed to 10 CD rats per sex per dose at dose levels of 0 (untreated diet), 100, 250, 500, or 1000 mg/kg/day continuously for 13 weeks. No mortalities occurred. Treatment-related red perinasal soiling and perineal urine soiling were observed in females at 500 and 1000 mg/kg/day. Treatment-related decreases in mean body weight and mean feed consumption were observed in females at 1000 mg/kg/day. Treatment-related increases in mean relative liver weight in both sexes at 500 and 1000 mg/kg/day and in mean relative kidney weight in females at 500 and 1000 mg/kg/day were observed. Macroscopic examination revealed treatment-related decreased amount of fat, kidneys with roughened surface, and pale kidneys in females at 500 and 1000 mg/kg/day. Microscopic examination revealed treatment-related centrilobular hepatocellular hypertrophy in both sexes at 500 and 1000 mg/kg/day, crystals within the collecting ducts and/or pelvis of the kidney in females at 500 and 1000 mg/kg/day, chronic, active inflammation of the renal tubules in females at 500 and 1000 mg/kg/day, and hyperplasia of the transitional epithelium of the renal papilla in both sexes at 250, 500, and 1000 mg/kg/day. ... NOEL (M/F)= 100 mg/kg/day based on microscopic renal effects.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

所有的给药都是通过灌胃标记的苯草酰胺（XDE-638）（未标记苯草酰胺的纯度为97.5%，三唑标记纯度> 99%，苯环标记纯度为98.4%）在0.5%的Methocel悬浮液中进行的。通常，每组使用4只/性别的老鼠在8个使用三唑标记的14C-XDE-638的测试中进行。另外一组4只雄性老鼠使用苯环标记的14C-XDE-638进行测试，以评估三唑和苯环部分之间的裂解程度。主要使用带有颈静脉插管的老鼠来确定单次给药后血浆、尿液和粪便中残留物浓度的时间过程，剂量为5或250 mg/kg苯草酰胺。这些老鼠在第7天（苯环标记的雄性也是在这一天）被牺牲，并在那时确定了组织残留物。最大血浆浓度（Cmax）的时间大约为0.5小时和2小时，分别对应于5和250 mg/kg的两种性别。在5和250 mg/kg时，达到最大浓度一半的时间（1/2 Cmax）分别确定为雄性2.6小时和3.0小时，雌性分别为2.9小时和5.6小时。因此，在两种剂量水平下，为了在早期暴露阶段获得组织和排泄物样本，大约达到Cmax和1/2 Cmax血浆水平，共有四组雄性和雌性老鼠在单次口服给药后被牺牲。在每个牺牲时间点，对24种组织中的每一个进行了放射性标记的测量。在各个时间间隔对汇集血浆中的主要代谢物进行了评估，并在牺牲时间对肝脏和肾脏组织中的代谢物进行了评估。每组有3只/性别的老鼠安装了胆管插管，并在24小时内间隔收集胆汁，以评估胆汁排泄率和代谢物分析。另外四组/性别的老鼠在实验的第16天之前，每天以5 mg/kg/天的剂量连续给药15天，然后用三唑标记的14C-XDE-638处理。这些老鼠被评估了排泄物中的残留物和组织中代谢物的水平，发现与非预处理老鼠相似。代谢物分离是通过使用C-18固定相和足够分离大多数主要峰的梯度程序的HPLC来实现的，检测是通过UV（254 nm）和14C检测器进行的。代谢物鉴定是通过保留时间和负离子LC/MS进行的。估计5 mg/kg的总吸收率大约为85%，无论性别。250 mg/kg后的吸收率要低得多（雄性17%，雌性32%）。除非另有说明，以下结果来源于单次给药5 mg/kg三唑标记苯草酰胺的管理。比较了在苯环或三唑标记后尿和粪便中代谢物的分布模式，表明大多数（至少90%）的苯草酰胺残留物在两个标记环之间保持完整。母化合物是尿液中含量最丰富的残留物，分别占雄性老鼠用三唑-或苯环标记14C的给药剂量的约31%和19%。女性在尿液中排出的标签百分比始终比男性高。在女性的7天尿液中，66%的给药剂量是母苯草酰胺。在7天收集的任何性别的粪便中，含量最丰富的代谢物是一种未表征的“代谢物Y”，在男性中占给药剂量的14%至19%，在女性中占6%。母苯草酰胺在男性粪便中占给药标签的12%至15%，在女性中占3%。根据胆汁中排出的标签百分比，24小时粪便标签中的大约88%代表吸收的苯草酰胺。考虑到女性通过尿液排出标签的比例较高，女性在24小时胆汁收集中排出的量比男性少得多（女性占给药剂量的14%，而男性占56%）。胆汁中最大的一个暂时识别的成分是5-羟基-或8-羟基-苯草酰胺的谷胱甘肽产物（占给药苯草酰胺的18%）。两种羟基苯草酰胺的葡萄糖苷酸产物（两种情况下的羟基化产物位置未知）似乎共同占胆汁中给药标签的约15%。在1/2 Cmax血浆浓度期间的组织的浓度评估显示，肝脏的初始残留浓度相对较高，而其他组织（除了“GI/摄入物”）的水平要低得多。到第7天，肝脏和所有其他组织中的放射性标记非常低。母苯草酰胺在血浆、肝脏和肾脏中的含量比任何其他残留物都要丰富。在血浆1/2 Cmax时，这些组织中苯草酰胺的浓度（以ug当量/g组织计）分别为：男性血浆10，肝脏44，肾脏3；女性血浆9，肝脏50，肾脏4。最初，这项研究是不可接受的，但可以通过识别“代谢物Y”来升级，后者构成了高达19%的粪便残留物。

All dosing was by gavage with labeled penoxsulam (XDE-638) (97.5% purity of unlabeled penoxsulam, triazole label purity > 99%, phenyl ring label purity 98.4%) in 0.5% Methocel suspension. Generally, groups of 4 rats/sex were used in each of 8 tests using triazole-labeled 14C-XDE-638. One additional set of 4 males was tested using phenyl-labeled 14C-XDE-638 to assess the extent of cleavage between triazole and phenyl moieties. Rats fitted with jugular vein cannulae were used primarily to determine the time course of residue concentrations in plasma, urine, and feces after single dosing with either 5 or 250 mg/kg penoxsulam. These rats were sacrificed on day 7 (as were the phenyl-labeled males), and tissue residues were determined at that time. Time to maximal plasma concentration (Cmax) was about 0.5 hr and 2 hr for both sexes at 5 and 250 mg/kg, respectively. Time to half of maximal concentration of radiolabel (1/2 Cmax) at 5 and 250 mg/kg were determined to be 2.6 hr and 3.0 hr for males, respectively, and 2.9 hr and 5.6 hr for females, respectively. Thus four sets of males and females were sacrificed following single oral dosing to achieve approximately Cmax and 1/2 Cmax plasma levels at the two dose levels, and to obtain tissue and excreta samples at early stages of exposure. Radiolabel was measured in each of 24 tissues at each sacrifice time. Quantities of major metabolites were assessed in pooled plasma at various intervals, and in liver and kidney tissue at sacrifice times. Three rats/sex were fitted with bile duct cannulae, and bile was collected at intervals over 24 hr to assess biliary excretion rate and metabolite analysis. Four additional rats/sex were dosed daily for 15 days with 5 mg/kg/day prior to treatment with triazole labeled 14C-XDE-638 on day 16. These rats were evaluated for residues in excreta and for tissue levels of metabolites, which were found to be comparable to non-pre-treated rats. Metabolite separation was by HPLC using C-18 stationary phase and a gradient program sufficient to separate most major peaks for detection by UV (254 nm) and by 14C-detector. Metabolite identification was by retention time and negative ion LC/MS. Estimated total absorption after 5 mg/kg was about 85% for either sex). Absorption was much lower after 250 mg/kg (17% in males, 32% in females). Unless otherwise stated, results below derive from single-dose administration of 5 mg/kg triazole-labeled penoxsulam. A comparison of distribution patterns of urinary and fecal metabolites following phenyl- or triazole-label indicated that most (at least 90%) of penoxsulam residues remained intact between the two labeled rings. Parent compound was the most abundant urinary residue, constituting about 31% and 19% of administered dose in urine samples of males dosed with triazole- or phenyl-labeled 14C, respectively. Females consistently excreted much larger percentages of label in urine than did males. In the 7-day urine collection in females, 66% of administered dose was parent penoxsulam. The most abundant fecal metabolite in either sex in the 7-day collection was an uncharacterized 'Metabolite Y,' comprising 14% to 19% of administered dose in males and 6% in females. Parent penoxsulam constituted 12% to 15% of administered label in feces of males and 3% in females. About 88% of 24-hr fecal label in males represented absorbed penoxsulam, based on percentage of label excreted in the bile. As expected, considering the proportionally higher excretion of label in females via the urine, females excreted much less in 24-hr bile collections than did males (14% of administered dose in females vs. 56% of administered dose in males). The largest single provisionally identified component of bile was the glutathione product of 5-hydroxy- or 8-hydroxy-penoxsulam (18% of administered penoxsulam). Two glucuronide products of hydroxylated penoxsulam (position of hydroxylation product unknown in either case) appeared to account together for about 15% of administered label in bile. Tissue concentration evaluations during times of 1/2 Cmax plasma concentrations revealed relatively high initial liver residue concentrations, whereas other tissues (except for 'GI/Ingesta') had much lower levels. Radiolabel in liver and in all other tissues were very low by day 7. Parent penoxsulam was much more abundant than any other residues in plasma, liver, and kidneys. Comparative concentrations of penoxsulam in ug-equivalents/g tissue at the time of plasma 1/2 Cmax for these tissues in males and females, respectively, were 10 and 9 for plasma, 44 and 50 for liver, and 3 and 4 for kidney. Originally, this study was unacceptable but upgradeable with identification of 'Metabolite Y,' which constituted up to 19% of fecal residues

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠的新陈代谢研究中，5.0 mg/kg低剂量的(14)C-penoxsulam被迅速且几乎完全吸收，但在250 mg/kg高剂量下，有证据表明吸收大部分不完整（即吸收达到饱和）。性别和剂量都影响了排泄模式。在低剂量下，放射性物质的主要排泄途径在雄性是通过粪便，在雌性是通过尿液。在高剂量下，放射性物质在两性中主要通过粪便排泄。特别是在雄性中观察到了显著的肠肝循环。大多数（>90%）的给药剂量在36-48小时内被排泄。在7天时组织中几乎没有放射性，没有在任何组织/器官中积聚的证据。尽管尿液、粪便和胆汁中揭示了众多的代谢物，但几乎所有的代谢物都小于给药剂量的1%。尿液和粪便中的主要化合物是母化合物和一种2-羟基苯基衍生物。

In a metabolism study in rats, (14)C-penoxsulam was rapidly and nearly completely absorbed at the low dose of 5.0 mg/kg, but at the high dose of 250 mg/kg, there was evidence that absorption was largely incomplete (i.e. absorption was saturated). Both gender and dose affected the excretion pattern. At the low dose, the major route of excretion of radioactivity was via the feces in males and via the urine in females. At the high dose, radioactivity was predominantly excreted via the feces in both sexes. A significant enterohepatic circulation was observed, particularly in males. Most (>90%) of the administered dose was excreted within 36-48 hours. There was negligible radioactivity in tissues at 7 days and no evidence of accumulation in any tissue/organ. Although numerous metabolites were revealed in the urine, feces and bile, nearly all were <1% of the administered dose. Parent compound and a 2-hydroxyphenyl derivative were the major compounds in urine and feces.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  N
• 安全说明：
  S61
• 危险类别码：
  R50/53
• WGK Germany：
  3
• 储存条件：
  | 0-6°C |

制备方法与用途

五氟磺草胺是一种强乙酞乳酸合成酶抑制剂,具有传导性,通过茎叶、幼芽及根系吸收,在木质部和韧皮部传导至分生组织，抑制植株生长。它适用于水稻的旱直播田、水直播田、秧田以及抛秧、插秧栽培田。

1. 生产方法：以2-甲氧基乙酸甲酯为起始原料，经过一系列化学反应得到五氟磺草胺。

   • 首先与甲酸甲酯、甲醇钠反应生成3-羟基-2-甲氧基丙烯酸甲酯的钠盐
   • 然后与甲基异硫脲反应得2,5-二甲氧基-4-羟基嘧啶
   • 接着用三氯氧磷氯化得到4-氯-2,5-二甲氧基嘧啶
   • 通过水合肼反应生成2,5-二甲氧基-4-肼基嘧啶
   • 使用溴化氰环合成3-氨基-5,8-二甲氧基【1,2,4】三唑并【4,3-c】嘧啶
   • 最后与甲醇钠反应生成中间体2-氨基-5，8-二甲氧基[1，2，4]-三唑并[1,5-c]-嘧啶 该中间体再与2-氟-6-三氟甲基苯磺酰氯反应得到五氟磺草胺

2. 毒性及环境影响：五氟磺草胺可被土壤迅速吸附，在大多数稻田的土壤中淋溶性较弱。其在粘质土及含高有机质的土壤中的吸附量高于轻质土及低有机质含量的土壤。在pH>8.0的土壤中具有加重药害的风险。该药剂在土壤中易移行，且非长期滞留。

3. 降解与消失：五氟磺草胺光解和微生物降解为其主要的消失途径，在水中抗水解但浅水层经光照可迅速消失。厌氧微生物降解是稻田土壤中五氟磺草胺消失的重要过程，其消减速度与其他方式相当。

4. 安全性：五氟磺草胺对水稻十分安全，2005年与2006年在美国对10个水稻品种于2-3叶期以70g(有效成分)/hm²剂量喷施后，稻株高度、抽穗期及产量均无明显差异，表明所有品种均有较强的抗耐性。

反应信息

• 作为产物：
  描述：

  5,8-二甲氧基-[1,2,4]三唑[1,5-c]嘧啶-2-胺 、 2-(2,2-二氟乙氧基)-6-(三氟甲基)苯磺酰氯 、 3,5-二甲基吡啶 在 二甲基亚砜 硫酸 、 乙腈 、 水 作用下， 反应 8.92h， 以18 g of product was obtained as a white solid assaying at 97.4 wt % (91% yield)的产率得到五氟磺草胺
  参考文献：
  名称：

  Process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides

  摘要：

  使用N-芳基磺酰氯与N-([1,2,4]三唑并[2,3-d] 嘧啶-2-基)胺的偶联反应，催化剂为N-芳基亚磺酰亚胺，可以通过选择3-哌啶或3,5-戊二醛作为碱来改善反应，形成N-([1,2,4]三唑并[2,3-d]嘧啶-2-基)芳基磺酰胺。

  公开号：

  US07339058B2

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。