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Diflufenzopyr | 1957168-02-3

中文名称
——
中文别名
——
英文名称
Diflufenzopyr
英文别名
2-[(E)-N-[(3,5-difluorophenyl)carbamoylamino]-C-methylcarbonimidoyl]pyridine-3-carboxylic acid
Diflufenzopyr化学式
CAS
1957168-02-3;109293-97-2
化学式
C15H12F2N4O3
mdl
——
分子量
334.28
InChiKey
IRJQWZWMQCVOLA-DNTJNYDQSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    155° (Bowe); also reported as 186° (Anderson).
  • 密度:
    0.24 g/cm3(Temp: 25 °C)
  • 闪点:
    150 °C
  • 颜色/状态:
    Off-white powder, solid
  • 气味:
    Odorless
  • 溶解度:
    1.88e-04 M
  • 蒸汽压力:
    less than 1.3X10-5 Pa /7.50X10-8 mm Hg/ at 20 °C
  • 分解:
    When heated to decomposition it emits toxic vapors of /nitrogen oxides and hydrogen fluoride/.
  • 解离常数:
    pKa = 3.18

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    24
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.07
  • 拓扑面积:
    104
  • 氢给体数:
    3
  • 氢受体数:
    7

ADMET

代谢
尿液、胆汁和粪便的代谢物分析是通过薄层色谱(TLC)、高效液相色谱(HPLC)、质谱和核磁共振光谱进行的。未改变的试验物质是所有排泄物中的主要标记化合物。主要的代谢反应包括环化、水解和羟基化,产生了7种主要代谢物(M1、M2、M5、M6、M9、M10和M19)。M19、M10和M9也在山羊和母鸡的排泄物以及玉米青贮饲料中被识别出来。
Metabolite analysis of the urine, bile and feces was conducted by TLC, HPLC, mass spectrometry and NMR spectroscopy. Unaltered test article was the major labeled compound in all excreta. Major metabolic reactions included cyclization, hydrolysis and hydroxylation, yielding 7 major metabolites (M1, M2, M5, M6, M9, M10 and M19). M19, M10 and M9 were also identified in excreta from goats and hens, and in corn silage.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性数据
LC50 (大鼠) >2,930 mg/m³
LC50 (rat) >2,930 mg/m3
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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。寻求医疗帮助。 /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%生理盐水(NS)或乳酸钠林格氏液。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:兔子的急性暴露/初级眼刺激;轻度到中度刺激(7天内解决)。
/LABORATORY ANIMALS: Acute Exposure/ Primary Eye Irritation in Rabbits; mild to moderate irritation (resolved within 7 days).
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
经口给药的大鼠中,氟夫洛芬佐吡被部分吸收并迅速消除;20-40%的剂量通过尿液排出,49-79%通过粪便排出。相比之下,静脉给药的大鼠有61-89%的剂量通过尿液排出。尿液和粪便中的消除半衰期为6小时。
Following oral administration /in rats/, Diflufenzopyr was partially absorbed and rapidly eliminated; 20-40% of the dose was eliminated in urine and 49-79% in feces. By contrast, intravenously dosed rats excreted 61-89% of the dose in urine. Elimination /half-time/ in urine and feces was 6 hr.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
diflufenzopyr 在蛋鸡和哺乳山羊体内的代谢研究。数据显示, diflufenzopyr 能迅速从动物体内排出。在饲料中添加量为10 ppm时,可食用组织、牛奶和鸡蛋中的残留水平低于0.12 ppm。
A metabolism study of diflufenzopyr was conducted in laying hens and lactating goats. The data showed diflufenzopyr was rapidly eliminated from the animals. With a feeding level of 10 ppm in the diet, residue levels in edible tissues, milk, and eggs were less than 0.12 ppm. ...
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
维斯特大鼠根据四种方案接受了(14)C标记的Diflufenzopyr(SAN 835 H苯基标记:放射性纯度>98%;吡啶基标记:放射性纯度>98%;未标记试验物品纯度=99.4%)的处理:1)单次静脉给药1 mg / kg,2)单次口服给药10 mg / kg,3)单次口服给药1000 mg / kg,4)连续十四天口服未标记试验物品,每天10 mg / kg,然后口服标记化合物的单次剂量为10 mg / kg。对于方案1、2和3,根据以下3个时间表对5只雄性和5只雌性大鼠进行监测:a)在给药后72小时处死,b)在给药后24小时处死,c)在给药后48小时处死的大鼠。对于重复给药方案,在用标记试验物品给药后24小时和72小时,各处死5只雄性和5只雌性大鼠。静脉给药导致两种标记形式的快速消除,在7小时内通过尿液排除了大约58-68%,在72小时内排除了70-90%。在大约7-20%通过粪便排出的物质中,几乎全部是由于胆汁排泄。口服给药10和1000 mg / kg主要通过粪便消除两种标记(在72小时内大约55-80%)。尿液排泄约占20-39%,胆汁排泄约占3-10%。在静脉或口服给药72小时后,组织保留率较低,对于苯基标记化合物(血液中最高)为0.37%或更低,对于吡啶基化合物(肾脏和肝脏中最高)为0.04%或更低。两种标记化合物的吸收百分比,通过将口服给药后排泄在尿液中的标记化合物量除以静脉给药后排泄在尿液中的量来计算,在30-50%之间,10和1000 mg / kg剂量水平之间没有差异。 ... 在试验物品的吸收、消除、组织分布或代谢方面,雄性与雌性之间没有显著差异。同样,高剂量和低剂量水平给出了相似的结果,这表明吸收或消除没有饱和。吡啶基标记化合物的组织保留较少,而苯基标记化合物在血液中的保留较多。最后,单次与多次给药的比较表明,试验物品不会生物累积或诱导代谢酶。
Wistar rats were administered (14)C-labeled Diflufenzopyr (SAN 835 H phenyl-labeled: radiochemical purity > 98%; pyridinyllabeled: radiochemical purity > 98%; unlabeled test article purity = 99.4%) according to each of four protocols: 1) a single i.v. dose at 1 mg/kg, 2) a single oral dose at 10 mg/kg, 3) a single oral dose at 1000 mg/kg, 4) fourteen daily oral doses of unlabeled test article at10 mg/kg followed by a single oral dose of labeled compound at 10 mg/kg. For protocols 1, 2 and 3, five males and five females were monitored according to each of 3 schedules: a) until sacrifice at 72 hrs post-dosing, b) until sacrifice at 24 hrs post-dosing, c) bile-duct cannulated animals followed until sacrifice at 48 hrs post-dosing. For the repeated dosing protocol, five males and five females were sacrificed at 24 hrs and 72 hrs after dosing with the labeled test article. Intravenous administration led to rapid elimination in the urine of between approximately 58 and 68% of both labeled forms by 7 hrs, and between 70 and 90% by 72 hrs. Of the approximate 7-20% excreted in the feces, almost all was a result of bilary excretion. Oral dosing at both 10 and 1000 mg/kg resulted in elimination of both labels mainly through the feces (approximately 55-80% by 72 hrs). Excretion in the urine accounted for approximately 20-39%, with approximately 3-10% excreted in the bile. Tissue retention at 72 hrs was low after either intravenous or oral dosing, being 0.37% or less for the phenyl-labeled compound (highest in blood) and 0.04% or less for the pyridinyl compound (highest in kidney and liver). The percent absorption for both labeled compounds, calculated by dividing the amount of labeled compound excreted in the urine after oral dosing by the amount excreted in the urine after i.v. dosing, was between 30 and 50%, with no difference between the 10 and 1000 mg/kg dose levels. ... There were no significant differences in test article absorption, elimination, tissue distribution or metabolism by males versus females. Likewise, high and low dose levels gave similar results, suggesting no saturation for absorption or elimination. There was less tissue retention of the pyridinyl-labeled compound and greater retention of the phenyl-labeled compound in the blood. Lastly, single versus multiple dosing showed that the test article did not bioaccumulate or induce metabolizing enzymes.
来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

氟吡草腙概述

氟吡草腙是一种缩氨基脲类、硫代缩氨基脲类和异硫代缩氨基脲类化合物,用于控制杂草。如果吸入氟吡草腙,请将患者移到新鲜空气处;若皮肤接触,应脱去污染的衣物,用肥皂水和清水彻底冲洗皮肤,如有不适感,请就医。

化学性质

氟吡草腙纯品为灰白色无味固体,熔点为135.5℃。其蒸气压在20/25℃时为(1 \times 10^{-7}) mPa。分配系数Kow lgP为0.037(pH 7)。Henry常数小于7×10^-5 Pa ·m^3/mol (20℃)。相对密度在25℃下为0.24。水中溶解度(25℃,mg/L):pH 5时为63,pH 7时为5850,pH 9时为100,546。水解半衰期DT₅₀:pH 5时为13天,pH 7时为24天,pH 9时为26天。水溶液光解半衰期DT₅₀:pH 5时为7天,pH 7时为17天,pH 9时为13天。pKa值为3.18。

制备

氟吡草腙的制备如下:将含有4-苯基氨基脲(0.37克,2.4毫摩尔)的5毫升甲醇溶液加入到2-乙酰基烟酸(0.40克,2.4毫摩尔)在7毫升甲醇中的水溶液中。混合物在室温下搅拌过夜后,用过滤收集固体沉淀,然后用乙醇洗涤并干燥,得到2-乙酰基烟酸4-苯基缩氨基脲,熔点为174℃(分解)。

作用机理与特点

氟吡草腙通过在蛋白质膜处与载体蛋白结合,抑制生长素的极性运输。与麦草畏混用时,可引导麦草畏向生长点运输,从而增加对阔叶杂草的效果。玉米的耐药性是由于其代谢迅速。这是一种内吸苗后除草剂,敏感的阔叶植物在几个小时内会表现出偏上性生长,而敏感的杂草则表现为生长迟缓。

应用

氟吡草腙可用于玉米、草场/牧场和非作物地区,用于苗后控制一年生阔叶杂草和多年生杂草。最初商品化时与麦草畏混配,两种原料均为钠盐。

毒性

雄性和雌性大鼠经口LD₅₀大于5.0 g/kg;经皮LD₅₀亦大于5.0 g/kg。对兔眼睛具有中度刺激,但对兔皮肤无刺激作用,且对豚鼠皮肤无致敏性。大鼠急性吸入LC₅₀为2.93 mg/L。狗的NOAEL(1年)为750 mg/L[雄性26 mg/(kg·d),雌性28 mg/(kg·d)]。EPA建议ADI (aRfD) 为1.0 mg/kg,cRfD 为0.26 mg/kg [1999年]。氟吡草腙无致畸、致癌作用。

反应信息

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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。
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(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫 龙胆紫 齐达帕胺 齐诺康唑 齐洛呋胺 齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯 齐培丙醇 齐咪苯 齐仑太尔 黑染料 黄酮,5-氨基-6-羟基-(5CI) 黄酮,6-氨基-3-羟基-(6CI) 黄蜡,合成物 黄草灵钾盐