甲基氨基甲酸-4-苯并噻嗯基酯百亩威猛捕因 | 1079-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 甲基氨基甲酸-4-苯并噻嗯基酯百亩威猛捕因
• 中文别名: 猛捕因
• 英文名称: mobam
• 英文别名: 1-benzothiophen-4-yl N-methylcarbamate
• CAS: 1079-33-0
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: BOTUVXISJHKZKJ-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  燃烧会产生有毒的氮氧化物和硫氧化物气体。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

MOBAM, (14)C-labeled in the ring, carbonyl or methyl position, was incuBAted with rumen BActerial cultures. Strains of genera Anaerovibrio, BActeroides, Butyrivibrio, EuBActerium, Lachnospira & Ruminococcus were deMOnstrated to degrade MOBAM. MOBAM was metabolized to 4-hydro-benzothiophene /and CO2/. 环上、羰基或甲基位标记的(14)C-MOBAM与瘤胃细菌培养物一起孵育。证实了Anaerovibrio、BActeroides、Butyrivibrio、EuBActerium、Lachnospira和Ruminococcus属的菌株能够降解MOBAM。MOBAM被代谢为4-羟基苯并噻吩和 。

MOBAM, (14)C-labeled in the ring, carbonyl or methyl position, was incubated with rumen bacterial cultures. Strains of genera Anaerovibrio, Bacteroides, Butyrivibrio, Eubacterium, Lachnospira & Ruminococcus were demonstrated to degrade MOBAM. MOBAM was metabolized to 4-hydro-benzothiophene /and CO2/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

(14)C-MOBAM被施用于奶牛和一头泌乳牛。在24小时内，有38%的甲基-(14)C和碳酰-(14)C以(14)CO的形式被呼出。

(14)C-MOBAM was administered to dairy goats and a lactating cow/. Of carbonyl-(14)C & 38% of methyl-(14)C were exhaled as (14)CO within 24 hr.

来源:Hazardous Substances Data Bank (HSDB)

代谢

给雄性大鼠群体通过胃管喂食了标记的MOBAM。每天收集尿液和粪便。羟基苯并噻吩以葡萄糖苷酸和硫酸盐的形式被回收。还发现了其他代谢物，但未进行鉴定。在给乳牛和一头泌乳奶牛喂食了(14)C-MOBAM后，尿液中发现了2种代谢物：4-苯并噻吩硫酸盐和4-苯并噻吩硫酸盐-1-氧化物。这些物质约占尿液中排出的(14)C的90%。

Groups of male rats were administered labeled MOBAM by stomach tube. Urine & feces were collected daily. Hydroxybenzothiophene was recovered as the glucuronide & as the sulfate. Other metabolites were found but not identified. After administration of (14)C-MOBAM to dairy goats and a lactating cow, 2 metabolites were found in urine: 4-benzothienyl sulfate & 4-benzothienyl sulfate-1-oxide. These accounted for about 90% of the (14)C excreted in the urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中给予标记有(14)C环的MOBAM后，24小时内76-87%的标记物通过尿液排出。苯基硫酚硫酸盐和葡萄糖苷酸占排出的(14)C的83-87%。在给乳牛和山羊施用甲基和羰基标记的MOBAM后的24小时内，识别出了亚砜、亚砜-4-硫酸盐、4-硫酸盐和4-葡萄糖苷酸。

In rats dosed with (14)C-ring labeled MOBAM, 76-87% of the label was excreted in 24 hr in urine. Benzenethienyl sulfate & glucuronide accounted for 83-87% of excreted (14)C. Within 24 hr after administration of methyl & carbonyl labeled MOBAM /to a dairy cow and a goat/, the sulfoxide, sulfoxide-4-sulfate, 4-sulfate & 4-glucuronide were identified.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲酰胺通过肝脏酶促水解；降解产物通过肾脏和肝脏排出。

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

莫巴是胆碱酯酶或乙酰胆碱酯酶（AChE）的抑制剂。氨基甲酸酯通过与酶的活性位点上的氨基甲酸化形成与胆碱酯酶的不稳定复合物。这种抑制作用是可逆的。胆碱酯酶抑制剂抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强效的神经毒素，即使在低剂量下也会导致过度流涎和眼泪。在更高剂量的暴露下，头痛、流涎、恶心、呕吐、腹痛和腹泻常常很明显。乙酰胆碱酯酶分解神经递质乙酰胆碱，该递质在神经和肌肉接头处释放，以便让肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积累并继续发挥作用，使得任何神经冲动持续传递，肌肉收缩不会停止。

Mobam is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

来源:Toxin and Toxin Target Database (T3DB)

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

• 健康影响

急性暴露于胆碱酯酶抑制剂可能会导致胆碱能危象，表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力可能性增加，如果呼吸肌肉受累，可能导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱表达的过度刺激。当这种情况发生时，可以看到肌肉无力、疲劳、肌肉痉挛、肌肉跳动和麻痹的症状。当自主神经节有乙酰胆碱积累时，这会导致交感系统中烟碱表达的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累，中枢神经系统中烟碱乙酰胆碱受体的过度刺激会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力，甚至可能昏迷。当由于副交感神经乙酰胆碱受体处乙酰胆碱过多而出现毒蕈碱过度刺激时，可能会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。长期高（>10年）暴露会导致神经心理学后果，包括感知和视动处理方面的障碍（A15321）。

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入 (L793)；口服 (L793)；皮肤给药 (L793)

Inhalation (L793) ; oral (L793); dermal (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

与有机磷化合物一样，症状和体征基于过度的胆碱能刺激。与有机磷中毒不同，氨基甲酸酯中毒的持续时间往往较短，因为神经组织乙酰胆碱酯酶的抑制作用是可逆的，氨基甲酸酯的代谢速度更快。肌肉无力、眩晕、出汗和轻微的身体不适是常见的早期症状。头痛、流涎、恶心、呕吐、腹痛和腹泻在较高暴露水平时常常较为明显。瞳孔收缩伴视力模糊、不协调、肌肉抽搐和言语不清也有报道。(L795)

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

在给予带有放射性碳-14标记的MOBAM给一头奶牛后的24小时内...86%...已经通过尿液排出...大约12%...通过粪便排出。在收集给予甲基和羰基标记的MOBAM后的尿液中，鉴定出了亚砜、亚砜-4-硫酸盐、4-硫酸盐和4-葡萄糖醛酸苷。

Within 24 hr after administration of (14)C-labeled MOBAM to a dairy cow ... 86% ... had been excreted in urine .... Approx 12% ... in the feces. In collected urines after administration of methyl and carbonyl labeled MOBAM, the sulfoxide, sulfoxide-4-sulfate, 4-sulfate and 4-glucuronide were identified.

来源:Hazardous Substances Data Bank (HSDB)

文献信息

• Insektizide Mittel, enthaltend Carbamate als Wirkstoffe und Triazolderivate als Synergisten
  申请人：BASF Aktiengesellschaft

  公开号：EP0007589A1

  公开（公告）日：1980-02-06

  Die vorliegende Erfindung betrifft insektizide Mittel, die insektizide Wirkstoffe aus der Gruppe der Carbamate, Phosphor(phosphonl-(di) (thio)-säureester, Pyrethrine, Pyrethroide, α-alkyl -phenyl-essigsäureester, α-Cyctopropyl-phenyl-essigsäureester und der chlorierten Kohlenwasserstoffe und zur Steigerung der insektiziden Wirksamkeit dieser Wirkstoffe Triazolderivate oder deren Salze enthalten. Die Triazolderivate haben die Formel in der R gegebenenfalls durch Halogen substituiertes Phenyl oder den Rest bedeutet, wobei Y für Wasserstoff, Halogen, Alkylmercapto mit 1 bis 6 Kohlenstoffatomen oder alkenylmercapto mit 2 bis 6 Kohlenstoffatomen, oder einen gegebenenfalls durch Halogen substituieren Phenylmercaptorest, X für Halogen und n fur 0, 1 oder 2 stehen, mit der Maßgabe, daß n nicht o bedeutet, wenn Y für Halogen steht.

  本发明涉及含有氨基甲酸酯类、磷（膦-（二）（硫）-酸酯类、除虫菊酯类、拟除虫菊酯类、α-烷基-苯基乙酸酯类、α-辛丙基-苯基乙酸酯类和氯化碳氢化合物类杀虫活性成分的杀虫组合物，以及用于提高这些活性成分杀虫效力的三唑衍生物或其盐类。 三唑衍生物的化学式为 R 是任选被卤素或自由基取代的苯基 其中 Y 是氢、卤素、具有 1 至 6 个碳原子的烷基巯基或具有 2 至 6 个碳原子的烯基巯基，或任选被卤素取代的苯基巯基、 X 是卤素，且 n 为 0、1 或 2，但当 Y 为卤素时，n 不为 o。
• Liquid foliar fertilizer compositions containing water-soluble urea-formaldehyde products
  申请人：ALLIED CORPORATION

  公开号：EP0013307A1

  公开（公告）日：1980-07-23

  Fertilizer liquid compositions comprising an aqueous solution of nitrogen, phosphorus and potassium macronutrient components are disclosed. The nitrogen is provided by a water-soluble urea-formaldehyde reaction product which is absorbed at about the same rate as other macronutrient components present in the fertilizer composition. The compositions of the present invention avoid phytotoxicity and metabolic imbalance in plants and provide for healthy plants with increased yields and a highly efficient utilization of nutrients when used either alone or in combination with other micronutrients, in foliar feeding of field crops such as legume and cereal grain crops and in turf care, horticulture and silviculture.

  本发明公开了由氮、磷和钾等主要营养成分的水溶液组成的液态肥料组合物。氮由水溶性脲醛反应产物提供，其吸收率与肥料组合物中的其他主要营养成分大致相同。本发明的组合物可以避免植物的植物毒性和代谢失衡，在单独使用或与其它微量营养元素结合使用时，可使植物健康，产量提高，养分利用率高，可用于大田作物（如豆类和谷类作物）的叶面施肥，也可用于草坪护理、园艺和造林。
• Verfahren zur Verbesserung der Löslichkeit biologisch aktiver Wirkstoffe in Wasser und niederen aliphatischen Alkoholen sowie neue Verbindungen mit verbesserter Löslichkeit
  申请人：BAYER AG

  公开号：EP0017772A1

  公开（公告）日：1980-10-29

  Die vorliegende Erfindung betrifft ein neues Verfahren zur Verbesserung der Löslichkeit biologisch aktiver Wirkstoffe mit mindestens einem Zerewitinoff-aktiven Wasserstoffatom in Wasser und niederen aliphatischen Alkoholen, neue nach diesem Verfahren hergestellte Verbindungen und ihre Verwendung, dadurch gekennzeichnet, dass man Wirkstoffe, OH, NH, NH2-monofunktionelle Polyether mit einem Wasseraufnahmevermögen von 10% und Verbindungen mit 2 gegenüber Zerewitinoff-aktiven Wasserstoffatomen reaktiven Gruppen miteinander umsetzt.

  本发明涉及一种新工艺，用于提高具有至少一个泽勒维蒂诺夫活性氢原子的生物活性剂在水和低级脂肪醇中的溶解度；通过该工艺制备的新化合物及其用途，其特征在于活性剂、OH、NH、吸水能力为10%的NH2-单官能团聚醚和具有2个对泽勒维蒂诺夫活性氢原子起反应的基团的化合物相互反应。
• Crosslinked, porous polymers for controlled delivery of agricultural ingredients
  申请人：CIBA-GEIGY AG

  公开号：EP0190996A2

  公开（公告）日：1986-08-13

  A controlled-release, delivery composition which comprises (A) a crosslinked copolymer, capable of swelling in ethanol to give a swollen copolymer containing at least 40% by weight of ethanol, and capable of swelling in water to give a swollen copolymer containing no more than 20% by weight of water, where the swelling ratio (% ethanol: % water) is 2:1 to 22:1, which comprises the copolymerization product of (a) 50 to 99 % by weight of said copolymer of a water-insoluble monoolefinic monomer or (a) with 0 to 45 % weight of total monomers of a water-soluble monoolefinic monomer, with (b) 50 to 1 % by weight, but not more than 20 mol % of a divinyl or polyvinyl crosslinking agent; and (B) an effective amount of an active agricultural ingredient is useful for the controlled and prolonged release of said ingredient.

  一种控释给药组合物，它包括(A)一种交联共聚物，该共聚物能在乙醇中溶胀，得到含乙醇至少 40%（重量）的溶胀共聚物，并能在水中溶胀，得到含水不超过 20%（重量）的溶胀共聚物，其中溶胀比（乙醇百分比：水百分比）为 2:1 至 22:1：(A)50-99%（重量百分比）的水不溶性单烯烃单体或(a)0-45%（重量百分比）的水溶性单烯烃单体与(b)50-1%（重量百分比）但不超过 20 摩尔%的二乙烯基或聚乙烯交联剂的共聚产物；以及(B)有效量的农业活性成分，有助于控制和延长所述成分的释放。
• Triazolderivate, Verfahren zu ihrer Herstellung sowie insektizide Mittel, welche diese enthalten
  申请人：BASF Aktiengesellschaft

  公开号：EP0008651B1

  公开（公告）日：1981-10-14

表征谱图