敌蝇威 | 644-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 敌蝇威
• 中文别名: 双甲胺替兰；2-二甲基氨基甲酰基-3-甲基-5-吡唑基-N，N-二甲基氨基甲酸酯
• 英文名称: dimetilan
• 英文别名: 1-dimethylcarbamoyl-5-methyl-3-pyrazolyl dimethylcarbamate；[1-(dimethylcarbamoyl)-5-methylpyrazol-3-yl] N,N-dimethylcarbamate
• CAS: 644-64-4
• 化学式: C₁₀H₁₆N₄O₃
• 分子量: 240.262
• InChiKey: RDBIYWSVMRVKSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

标记的二甲基甲酸酯通过口服给大鼠。...回收了2种代谢物但未鉴定出来。...其他研究表明，存在一种微粒体系统，需要TPNH（还原型烟酰胺腺嘌呤二核苷酸）和氧气，作用于n,n-二烷基甲酸酯。去烷基化发生时，从n,n-二甲基甲酸酯形成甲醛，但不从n-甲基甲酸酯形成。二甲基甲酸酯被这个系统降解；观察到2-甲基甲酸酯基-3-甲基-5-吡唑基二甲基甲酸酯+ 2种未鉴定的化合物。/在家蝇、美洲和德国蟑螂中/...甲酸酯酯基的水解部分解释了一些代谢，因为注入剂量的13%以(14)CO2的形式释放出来...首先形成的代谢物和主要产物可能是2-二甲基甲酸酯基-3-甲基-5-吡唑基n-羟甲基n-甲基甲酸酯。...在所有3种昆虫中发现的第三种代谢物与2-n-甲基甲酸酯基-3-甲基-5-吡唑基二甲基甲酸酯共同色谱，并表现出相同的生物活性。

Labeled dimetilan was administered orally to rats. ... 2 metabolites were recovered but not identified. ...other studies have shown a microsomal system, requiring TPNH and oxygen, that acts on n,n-dialkyl carbamates. Dealkylation occurs with formation of formaldehyde from n,n-dimethylcarbamates but not from n-methylcarbamates. Dimetilan was degraded by this system; and 2-methylcarbamoyl-3-methyl-5-pyrazolyl dimethyl carbamate + 2 unidentified compounds were observed. /in houseflies, American and German cockroaches/...hydrolysis of the carbamate ester group accounted for some metabolism, since 13% of the injected dose was liberated as (14)CO2...the metabolite formed first and the major product was probably 2-dimethylcarbamoyl-3-methyl-5-pyrazolyl n-hydroxymethyl n-methylcarbamate. ... A third metabolite found in all 3 insects co-chromatographed with 2-n-methylcarbamoyl-3-methyl-5-pyrazolyl dimethylcarbamate and exhibited the same biological activity.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 黑曲霉 van Tieghem 的敌草隆代谢被研究。与水解一起，烷基侧链的氧化似乎是最重要的改性（解毒）过程。

... The metabolism of dimetilan in Aspergillus niger van Tieghem /was studied/. Together with hydrolysis, oxidation of the alkyl side chain appeared the most important modification (detoxification) process.

来源:Hazardous Substances Data Bank (HSDB)

代谢

N-甲基羟基化似乎是昆虫解毒的主要因素。

N-methyl hydroxylation appears to be major factor in detoxication in insects.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氨基甲酸酯通过肝脏酶促水解；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

敌百虫是一种胆碱酯酶或乙酰胆碱酯酶（AChE）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不稳定的复合物来抑制胆碱酯酶。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。在更高水平的暴露下，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。

Dimetilan 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

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

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，可能会导致死亡。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、肌肉颤动和麻痹的症状。当自主神经节积累乙酰胆碱时，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。当由于副交感神经节积累乙酰胆碱而引起毒蕈碱过度刺激时，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，且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更为明显。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

标记的地美甲兰通过口服给予大鼠。治疗后4小时内，尿液中含有所给予放射性活性的10%，在接下来的18小时内又增加了3%。...观察到一定量的二氧化碳产生。...在家蝇、美洲蟑螂和德国蟑螂中/...1小时内，注射剂量的13%以(14)CO2的形式释放出来...

Labeled dimetilan was administered orally to rats. Within 4 hr after treatment the urine contained 10% of the administered radioactivity and an additional 3% within the next 18 hr. ... Some production of carbon dioxide was observed. ... /in houseflies, American cockroaches, and German cockroaches/...13% of the injected dose was liberated as (14)CO2 within 1 hr...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

氨基甲酸酯类杀虫剂在大鼠体内迅速消除。在腹腔注射氨基甲酸酯的羰基(14)C标记物后49小时内，89%的放射性物质被消除。部分以CO2（25-77%）的形式出现，尿液中的代谢产物（12-65%）和粪便中的代谢产物（1-6%），剩余的2-12%留在体内。/氨基甲酸酯/

...Carbamate insecticides...are rapidly...eliminated in rats. Within 49 hr after ip injection of carbonyl (14)C-labeled carbamate 89% of radioactivity was eliminated. Part appeared as CO2 (25-77%), products in urine (12-65%), and products in feces (1-6%), with 2-12%...remaining in body. /Carbamates/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

氨基甲酸酯类杀虫剂迅速渗透进入昆虫体内，40-80%的剂量（每只家蝇1微克）在4-8小时内渗透。在哺乳动物中，氨基甲酸酯不会在体内积累或通过乳汁排出。

Carbamates penetrate rapidly into insects, from 40-80% of topical dosage of 1 ug per housefly, penetrating within 4-8 hr. ... In mammals...carbamates are not accumulated in body or excreted in milk. /Carbamates/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

氨基甲酸酯类杀虫剂会迅速通过尿液排出体外。

.../Carbamate insecticides/ are rapidly... excreted in urine. /Carbamates/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  库房应保持通风、低温和干燥，并与食品原料分开储运。

反应信息

• 作为反应物：
  描述：

  敌蝇威 在 铜 柠檬酸 作用下， 以 acetate buffer 为溶剂， 生成 二甲胺 、 3-甲基-3-吡唑啉-5-酮 、 二氧化碳
  参考文献：
  名称：

  金属离子和有机配体协同催化二甲胺水解

  摘要：

  具有N,N-二甲基氨基甲酸酯部分和N,N-二取代脲部分的杀虫剂二甲胺的水解已被用于探索金属离子-有机配体对农用化学品降解的协同作用。Dimetilan 水解受到 +II 过渡金属离子的强烈催化，该离子对氮和氧供体配体（NiII、CuII 和 ZnII）表现出强亲和力，但对仅表现出弱亲和力的 PbII 则没有。这四种金属离子之间的比较强烈表明，二美泰兰的金属离子配位是催化发生所必需的。金属离子配位二甲胺和生成 MeOH+ 亲核试剂的联合机理对于金属催化的水解是最合理的。在没有金属离子的情况下，柠檬酸（CIT）、乙二胺（EN）、单独的 N-(2-羟乙基)乙二胺 (HEEN) 配体不影响二甲胺水解。然而，这些配体的加入显着改变了金属离子的催化作用。CIT和EN降低了...

  DOI：

  10.1021/es0009673

文献信息

• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [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。
• THIENYLPYRIDYLCARBOXAMIDES
  申请人：Dunkel Ralf

  公开号：US20110105564A1

  公开（公告）日：2011-05-05

  Novel thienylpyridylcarboxamides of the formula (I) The present application is also directed to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

  新型噻吩基吡啶基羧酰胺的化学式（I） 本申请还涉及多种制备这些化合物的方法，以及它们用于控制不受欢迎的微生物的用途，还有新颖的中间体及其制备。
• Novel insecticides
  申请人：Syngenta Participations AG

  公开号：EP2540718A1

  公开（公告）日：2013-01-02

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

  式I的化合物 其中取代基如权利要求1所定义，并且式I化合物的农药可接受盐以及所有立体异构体和互变异构形式可用作杀虫剂，并且可以按照已知的方法制备。