双氟磺草胺 | 145701-23-1

• 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: 双氟磺草胺
• 中文别名: 麦施达；N-(2,6-二氟苯基)-8-氟代-5-甲氧基-[1,2,4]三唑[1,5-c]嘧啶-2-磺酰胺；麦施达,麦喜为,2',6'-二氟-5-乙氧基-8-氟[1,2,4]三唑[1,5-c]嘧啶-2-磺酰苯胺；吡氟草胺；2',6'-二氟-5-乙氧基-8-氟[1,2,4]三唑[1,5-c]嘧啶-2-磺酰苯胺；2',6'-二氟-5-乙氧基-8-氟[1,2,4]三唑[1,5-C]嘧啶-2-磺酰苯胺
• 英文名称: florasulam
• 英文别名: N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide；2',6',8-trifluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonanilide；flurasulam；2',6'-difluoro-5-methoxy-8-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonanilide；N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
• CAS: 145701-23-1
• 化学式: C₁₂H₈F₃N₅O₃S
• mdl: MFCD08273843
• 分子量: 359.288
• InChiKey: QZXATCCPQKOEIH-UHFFFAOYSA-N

物化性质

• 熔点：
  220-221° (dec) (Van Heertum); also reported as 193.5-230.5° (Thompson)
• 密度：
  1.75±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、乙酸乙酯（微溶）、甲醇（微溶）
• LogP：
  1.290 (est)
• 颜色/状态：
  Solid
• 蒸汽压力：
  1X10-2 mPa /7.501X10-8 mm Hg/ at 25 °C
• 稳定性/保质期：
  Hydrolytically stable for 30 days (pH 5 and 7); DT50 100 days (pH 9) (all 25 °C)
• 解离常数：
  pKa = 4.54

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  10

ADMET

代谢

(14)C-XDE-570（Florasulam；99.3-99.5%放射性纯度）以0.5%的Methocel纤维素醚悬浮液形式给予5只/性别的Fischer 344大鼠，单次灌胃剂量为10或500 mg/kg体重。此外，5只/性别的老鼠接受了14天的剂量，每天10 mg/kg体重，非标记的florasulam，然后在第15天给予单次口服剂量的(14)C-florasulam。对于每个测试组，(14)C-Florasulam在芳环上均匀标记。另外，5只雄性老鼠接受了10 mg/kg体重的单次灌胃剂量，(14)C-florasulam（在三唑-嘧啶环的第9位标记）。所有动物在给予放射性标记剂量后168小时被处死。...已识别的化合物占每个组给药量的87.6-91.6%。在每组中，分离出以下化合物：母体占77.7-85.0%剂量，OH-苯基-XR-570（羟基的确切位置未确定）占3.1-9.0%剂量，OH-苯基-XR-570硫酸结合物占2.8-3.7%剂量，2个未识别的代谢物占小于或等于0.32%剂量。在高剂量中，与低剂量相比，更多的母体在粪便中被分离出来，尿液中较少。

(14)C-XDE-570 (Florasulam; 99.3-99.5% radiochemical purity) in a suspension of 0.5% Methocel cellulose ethers was administered to 5 Fischer 344 rats/sex as a single gavage dose at 10 or 500 mg/kg bw. Additionally, 5 rats/sex were treated with 14 daily doses at 10 mg/kg bw/day of non-labeled florasulam followed by a single oral dose of (14)C-florasulam on Day 15. (14)C-Florasulam was uniformly labeled in the aniline ring for each of these test groups. In addition, 5 males were treated with a single gavage dose at 10 mg/kg bw with (14)C-florasulam (labeled at the 9 position in the triazolo-pyrimidine ring). All animals were killed 168 hours after the administration of the radiolabeled dose. ... Identified compounds accounted for 87.6-91.6% of the administered dose in each group. In each group, the following compounds were isolated: parent accounted for 77.7-85.0% dose, OH-phenyl- XR-570 (exact position of hydroxyl group not determined) accounted for 3.1-9.0% dose, OH-phenyl-XR-570 sulfate conjugate accounted for 2.8-3.7% dose, and 2 unidentified metabolites accounted for < or = 0.32% dose. In the high dose, more of the parent was isolated in the feces and less in the urine compared to the low dose.

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，协助通气。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……。预期癫痫发作，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，如果患者能够吞咽、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"，最低流量/。如果出现低血容量的迹象，使用0.9%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

实验动物：亚慢性或前慢性暴露/在重复剂量皮肤毒性研究中，将含有XDE-570（草.sulam；99.3%活性成分）的水性0.5% Methocel应用于剃毛后的大鼠Fischer 344的皮肤，剂量水平为0、100、500或1000毫克/千克/天，每天6小时，每周7天，持续28天。在任一性别中，都没有观察到与化合物相关的死亡、临床体征、体重、体重增加、食物消耗、血液学、临床化学、尿液分析、器官重量以及大体或显微病理参数的影响。在1000毫克/千克/天的剂量下，从第23天开始在5/4雄性动物的治疗部位观察到非常轻微（1级）的水肿和红斑。皮肤刺激在第28天得到解决。系统性的最低观察到不良效应水平（LOAEL）未确定，系统性的无观察到不良效应水平（NOAEL）为1000毫克/千克/天。基于在雄性动物（4/5）的治疗部位观察到水肿和红斑，皮肤LOAEL为1000毫克/千克/天，皮肤NOAEL为500毫克/千克/天。

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a repeated-dose dermal toxicity study, XDE-570 (Florasulam; 99.3% ai) in aqueous 0.5% Methocel was applied to the shaved skin of 5 Fischer 344 rats/sex/dose at dose levels of 0, 100, 500, or 1000 mg/kg/day, 6 hours/day for 7 days/week during a 28-day period. No compound related effects in mortality, clinical signs, body weight, body weight gain, food consumption, hematology, clinical chemistry, urinalysis, organ weights, and gross or microscopic pathology parameters were observed in either sex. At 1000 mg/kg/day, very slight (grade 1) edema and erythema at the treatment site were noted in 4/5 males beginning on Day 23. Dermal irritation was resolved by Day 28 . The systemic LOAEL is not determined and the systemic NOAEL is 1000 mg/kg/day. The dermal LOAEL is 1000 mg/kg/day, based on edema and erythema observed at the treatment site in males (4/5). The dermal NOAEL is 500 mg/kg/day.

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/ 在一项90天口服毒性研究中，XDE-570（Florasulam；99.3% ai）以0、5、50或100 mg/kg/天的剂量水平通过饮食自由给予4只/性别/剂量的比格犬（雄性和雌性的平均测试物质摄入量分别为0/0、6/6、56/55和104/94 mg/kg/天）持续13周。在任何剂量下，都没有观察到与化合物相关的对死亡率、临床体征、体重、体重增加、食物消耗、眼检、血液学、尿检或大体病理的影响。靶器官似乎是肝脏。在50 mg/kg剂量下，碱性磷酸酶活性在雄性中增加了59-112%，在雌性中增加了91-127%，在第45天和第91天，肝细胞空泡化的发生率略有增加（3/4处理组（非常轻微到轻微程度）与1/4对照组（中等程度）的雌性）。在100 mg/kg剂量下，观察到以下肝脏效果：(i) 碱性磷酸酶活性在两性中均显著增加（p<0.05），在第45天和第91天增加了213-451%；(ii) 肝细胞空泡化（非常轻微到轻微程度）的发生率增加（4/4处理组与3/4对照组的雄性和3/4处理组与1/4对照组的雌性）；(iii) 绝对（增加22-29%）和相对（相对于体重；增加26-27%）肝重量在两性中均增加（p<0.05）。基于两性中碱性磷酸酶活性（增加59-127%）的增加以及肝细胞空泡化的发生率/严重程度的增加，最低观察到有害作用剂量（LOAEL）为50 mg/kg/天。无观察到有害作用剂量（NOAEL）为5 mg/kg/天。

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day oral toxicity study, XDE-570 (Florasulam; 99.3% ai) was administered to 4 Beagle dogs/sex/dose ad libitum in the diet at dose levels of 0, 5, 50, or 100 mg/kg/day (time-weighted average test substance intake was 0/0, 6/6, 56/55, and 104/94 mg/kg/day (M/F)) for 13 weeks. There were no compound-related effects on mortality, clinical signs, body weight, body weight gain, food consumption, ophthalmoscopy, hematology, urinalysis, or gross pathology observed at any dose. The target organ appeared to be the liver. At 50 mg/kg, alkaline phosphatase activity was increased (p<0.05) by 59-112% in the males and 91-127% in the females on Days 45 and 91, and there was a slight increase in the incidence of hepatic vacuolation (3/4 treated (very slight to slight severity) vs. 1/4 control (moderate severity) females). At 100 mg/kg, the following liver effects were noted: (i) alkaline phosphatase activity was increased (p<0.05) by 213-451% in both sexes on Days 45 and 91; (ii) increased incidence of very slight to slight hepatic vacuolation (4/4 treated vs. 3/4 control males and 3/4 treated vs. 1/4 control females); and (iii) increased (p<0.05) absolute (incr. 22-29%) and relative (to body; incr. 26-27%) liver weight in both sexes. The LOAEL is 50 mg/kg/day, based on increased alkaline phosphatase (59-127%) activity and increased incidence/severity of hepatic vacuolation in both sexes. The NOAEL is 5 mg/kg/day.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

迅速吸收（口服给药后），约91%在24小时内排出，主要在尿液中，主要以未改变的 florasulam 形式排出。

Rapidly absorbed (following oral administration), with about 91% excretion within 24 hr, mainly in the urine, and mainly as unchanged florasulam.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在一项皮肤渗透研究中，将含有14C的XDE-570（Florasulam；应用时的放射性纯度为98-99%）涂敷在Fischer 344大鼠（每个时间点每种剂量水平4只雄性）的皮肤上（12平方厘米）。名义剂量为每平方厘米皮肤0.001毫克或0.5毫克。高剂量（EF-1343商业配方）用于评估混合/装载人员的暴露。低剂量（喷雾稀释，使用EF-1343空白作为载体）代表了一种比预期用于田间作物喷雾的最高浓度高出2.39倍的剂量，这是为了提供足够分析灵敏性所必需的。暴露持续时间为24小时，之后每个剂量水平的4只雄性大鼠中的一组被牺牲。剩余的两组/剂量在涂抹后48小时或72小时被牺牲。应用剂量的回收（质量平衡）为100-103%。大部分剂量在皮肤擦拭物中回收（占应用剂量的71-90%）。皮肤吸收（基于尿液、粪便、笼子清洗液、组织、残留尸体和未处理皮肤中残留物的总和）仅为应用剂量的0.13-0.45%，并且只有10-22%的应用剂量残留在涂抹部位皮肤中（被认为可能被吸收）。将剂量增加200倍，吸收量仅增加了大约2倍。在低剂量组中，吸收量在48小时增加了44%，在72小时增加了61%，与24小时相比；然而，在高剂量组中没有明显的时间依赖性吸收增加。在低剂量下，吸收的剂量几乎完全通过尿液排出，但在高剂量下，主要在尿液、笼子清洗液和未处理皮肤中发现。在低剂量下，处理部位的放射性在48小时增加，但在72小时内任剂量下都没有减少，这表明皮肤中的化合物不易被吸收。在72小时（包括24小时暴露期）后，从处理过的皮肤中分离出的化合物会被忽略不计地吸收。观察到的最高皮肤吸收为应用剂量的0.45%。这个值在应用适当的不确定性因素后，被认为是用于风险评估的合适值。

In a dermal penetration study, (14)C-XDE-570 (Florasulam; 98-99% radiochemical purity as applied) was applied to the skin (12 sq cm) of Fischer 344 rats (4 males for each time point at each dose level). Nominal doses were 0.001 or 0.5 mg/sq cm skin. The high dose (EF-1343 commercial formulation) was included to assess exposure to mixer/loaders. The low dose (spray dilution, using an EF-1343 blank as a vehicle) represented a dose that was 2.39-fold more concentrated than the highest anticipated spray concentration for use on field crops, which was necessary in order to provide sufficient analytical sensitivity. The exposure duration was 24 hours, after which one group of 4 males for each dose level was sacrificed. The remaining 2 groups/dose were sacrificed at 48 or 72 hours post-application. Recovery of the applied dose (mass balance) was 100-103%. The majority of the dose was recovered in the skin swab (71-90% of the applied dose). Dermal absorption (based on the sum of residues in urine, feces, cage wash, tissues, residual carcass, and untreated skin) was only 0.13-0.45% of the applied dose and only 10-22% of the applied dose remained in the skin at the application site (considered potentially absorbable). Increasing the dose 200-fold resulted in only approximately 2-fold increase in absorption. Absorption increased 44% at 48 hr and 61% at 72 hr compared to 24 hr in the low dose groups; however, a time-dependent increase in absorption was not evident in the high dose groups. The absorbed dose was almost completely excreted in the urine at the low dose, but was found primarily in the urine, cage wash, and untreated skin at the high dose. The amount of radioactivity at the treatment site increased at 48 hours in the low dose, but did not decrease within 72 hours at either dose, suggesting that the compound in the skin was not readily absorbable. The compound isolated in the treated skin after 72 hours (including the 24 hour exposure period) would be absorbed in negligible amounts. The highest dermal absorption noted was 0.45% of the applied dose. This value is considered appropriate for use in risk assessment, with the appropriate uncertainty factors applied.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C-XDE-570（草.sulam；99.3-99.5%放射性纯度）在0.5%甲基纤维素醚悬浮液中给药给5只Fischer 344大鼠/性别，单次灌胃剂量为10或500毫克/千克体重。此外，5只大鼠/性别接受14天剂量，每天10毫克/千克体重的非标记草.sulam，然后在第15天给予单次口服(14)C-草.sulam剂量。(14)C-Florasulam在每个测试组中都均匀标记在苯环上。此外，5只雄性大鼠接受单次灌胃剂量10毫克/千克体重与(14)C-草.sulam（在噻唑-pyrimidine环的9位点上标记）。所有动物在给药放射性剂量后168小时被处死。吸收是迅速和广泛的。在10毫克/千克的大鼠中，大约90-93%的剂量被吸收，在500毫克/千克的大鼠中，82-86%的剂量被吸收（根据尿液中检测到的放射性活度、组织/尸体和笼子冲洗的总和计算）。在10或500毫克/千克剂量给药后0.5-1小时内达到血浆峰浓度（Cmax）。血浆中的Cmax并未随着剂量的增加而成比例增加，这可能表明在高剂量时吸收和/或排泄机制达到饱和。在高位时，表观分布容积增加，可能表明组织结合增加。在给药后168小时的总回收率为95.9-100.2%。消除是迅速的。在12小时内，大部分给药剂量通过尿液消除（10毫克/千克的大鼠>80%的剂量，500毫克/千克的大鼠>60%的剂量）。在单次或重复低剂量治疗后，尿液中发现的放射性总量约为剂量的90-92%，在500毫克/千克治疗后的剂量的81-85%。在10毫克/千克时，粪便中的放射性占剂量的另外5-7%，在500毫克/千克时占14-17%。因此，与低剂量相比，高剂量的排泄速度稍慢，并且更多的化合物通过粪便排出。在24小时，<0.5%的剂量在呼出的空气中。在24小时后，血浆水平在10毫克/千克的两个性别中降至<0.1ug eq/g血浆，在500毫克/千克的两个性别中降至<5.0ug eq/g血浆。在皮肤（单次剂量）和尸体（重复剂量）中观察到最高的残留水平，但在处死时组织/尸体中放射性活度的平均回收率<0.6%。

(14)C-XDE-570 (Florasulam; 99.3-99.5% radiochemical purity) in a suspension of 0.5% Methocel cellulose ethers was administered to 5 Fischer 344 rats/sex as a single gavage dose at 10 or 500 mg/kg bw. Additionally, 5 rats/sex were treated with 14 daily doses at 10 mg/kg bw/day of non-labeled florasulam followed by a single oral dose of (14)C-florasulam on Day 15. (14)C-Florasulam was uniformly labeled in the aniline ring for each of these test groups. In addition, 5 males were treated with a single gavage dose at 10 mg/kg bw with (14)C-florasulam (labeled at the 9 position in the triazolo-pyrimidine ring). All animals were killed 168 hours after the administration of the radiolabeled dose. Absorption was rapid and extensive. Approximately 90-93% of the dose was absorbed in the 10 mg/kg rats, and 82-86% was absorbed in the 500 mg/kg rats (based on the sum of radioactivity detected in the urine, tissues/carcass, and cage rinse). Peak plasma concentrations (Cmax) were achieved within 0.5-1 hour following dose administration at 10 or 500 mg/kg. Cmax in the plasma did not increase proportionally with dose, possibly indicating a saturation of the absorption and/or excretion mechanisms at the high dose. The apparent volume of distribution was increased at the high dose, possibly indicative of increased tissue binding. Total recoveries at 168 hours post-dose were 95.9-100.2% of the administered dose. Elimination was rapid. The administered dose was mostly eliminated within 12 hours in the urine (>80% of the dose at 10 mg/kg and >60% of the dose at 500 mg/kg). Total radioactivity found in the urine was approximately 90-92% of the dose following single or repeated low-dose treatment, and 81-85% of the dose following treatment at 500 mg/kg. Radioactivity in the feces accounted for another 5-7% at 10 mg/kg and 14-17% at 500 mg/kg. Thus, compared to the low dose, excretion of the high dose was slightly slower, and more of the compound was excreted in the feces. At 24 hours, <0.5% of the dose was found in expired air. By 24 hours post-dose, plasma levels had declined to <0.1ug eq/g plasma in both sexes at 10 mg/kg and <5.0 ug eq/g plasma in both sexes at 500 mg/kg. The highest residue levels were observed in the skin (single dose) and carcass (repeated dose), but the mean recovery of radioactivity in the tissues/carcass at sacrifice was <0.6% of the dose.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  N
• 安全说明：
  S60
• 危险类别码：
  R50/53
• WGK Germany：
  2
• 危险品运输编号：
  UN 3077 9 / PGIII
• 储存条件：
  0-6°C

制备方法与用途

双氟磺草胺是一种高效的选择性茎叶处理除草剂。请根据以下信息了解其详细内容：

主要特点

• 作用机理：通过抑制乙酰乳酸合成酶（ALS），从而阻止杂草生长。
• 选择性：对麦类作物和草坪具有高度选择性，而对大部分阔叶杂草有效。

使用效果

• 在欧洲和加拿大，双氟磺草胺每公顷的最大使用剂量分别为7.5g和5g。
• 每公顷用量为5-15g时，对于草坪及放牧场中的黑麦草、多花黑麦草等具有良好的选择性效果。

使用方法

• 双氟磺草胺可以用于播前混土及苗前土壤处理或苗后喷雾。
• 它的可混性较强，可以在小麦田中与其他成分如液态氮混合使用以降低用药量至2.5g/公顷。

简要合成路径

1. 从2,4-二氯-5-氟嘧啶开始；
2. 经过醚化反应、肼化反应、环合反应等七步反应最终得到双氟磺草胺。

专利情况

• 欧洲：EP 0343752（已终止）
• 英国补充保护证书SPC/GB00/009（最长有效期至2013年12月3日）
• 美国：US 5010195（已届满）
• 中国专利均已届满

应用

双氟磺草胺主要用于冬小麦田除草，它广泛应用于冬小麦、春小麦、草坪及草地。

总的来说，双氟磺草胺是一种高效的选择性除草剂，在合适的使用条件下可以显著提高作物产量和质量。

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
  ——	2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine	147150-78-5	C6H4ClFN4O3S	266.64

反应信息

• 作为反应物：
  描述：

  双氟磺草胺 在 2-叔丁基-1,1,3,3-四甲基胍 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 2-(benzylsulfonyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  仲磺酰胺的还原裂解：将末端官能团转化为多功能合成手柄

  摘要：

  磺胺类药物普遍存在于药物和农用化学品中，但它们通常被认为是末端官能团而不是合成手柄。为了实现仲磺酰胺的一般后期功能化，我们开发了一种温和且通用的方法来还原性裂解磺酰胺的 NS 键以生成亚磺酸盐和胺，这些成分可以进一步原位反应以获得各种其他与医学相关的功能组。该平台的实用性通过对几种复杂生物活性分子的选择性操作而突出。

  DOI：

  10.1021/jacs.9b10985
• 作为产物：
  描述：

  2-甲氧基-4-氯-5-氟嘧啶 在 盐酸 、 1,2-丙二醇 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 双氟磺草胺
  参考文献：
  名称：

  一种三唑并嘧啶类除草剂的制备方法

  摘要：

  本发明属于有机合成技术领域，尤其涉及一种三唑并嘧啶类除草剂的制备方法。该制备方法具体包括以下步骤：a)将式(I)结构化合物与氨基硫脲进行反应，之后在碱性条件下异构化，得到式(II)结构化合物；b)将所述式(II)结构化合物与亚硝酸钠进行重氮化反应，然后再与亚硫酸氢钠和氯化物混合反应，得到式(III)结构化合物；所述氯化物包括氯化铜和/或氯化亚铜；c)将所述式(III)结构化合物与式(IV)结构化合物进行反应，得到具有式(V)结构的三唑并嘧啶类除草剂。本发明提供的制备方法反应条件温和，安全风险低，环保性好。

  公开号：

  CN111217817B

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。