畜虫威 | 2655-19-8

• 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: 畜虫威
• 中文别名: 畜虫威；3，5-二特丁基苯基-N-甲基氨基甲酸酯
• 英文名称: butacarb
• 英文别名: 3,5-Di-tert.-Butylphenyl-N-methylcarbamat；3,5-di-t-butylphenyl-N-methyl carbamate；(3,5-ditert-butylphenyl) N-methylcarbamate
• CAS: 2655-19-8
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: SLZWBCGZQRRUNG-UHFFFAOYSA-N

物化性质

• 熔点：
  102.9°C
• 沸点：
  406.62°C (rough estimate)
• 密度：
  0.9903 (rough estimate)
• 颜色/状态：
  WHITE CRYSTALLINE SOLID
• 溶解度：
  In water, 15 mg/L at 25 °C
• 蒸汽压力：
  1.98X10-6 mm Hg at 20 °C
• 稳定性/保质期：

  Stable to light, heat and hydrolysis under normal conditions

• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

当丁草胺与小鼠肝脏10,000xg上清液一起孵化时，检测到了十一种代谢物。水解只产生了6种酚。其中之一，主要的代谢物，被鉴定为3,5-二叔丁基酚。其他代谢物被表征，但并非全部都完全鉴定：两种含有羧基和氨基甲酰基的酸代谢物；两种含有氨基甲酰基和两个羟基的（但不是二羟基苯）；一种羟基丁基酚；一种含有氨基甲酰基和羟基的；两种二羟基丁基酚；N-羟甲基丁草胺；和N-羟甲基羟基丁基类似物。对家蝇（Musca domestica）、绿头苍蝇（Lucilia sericata）和草甲虫（Costelytra zealandica）的研究得到了与小鼠肝脏酶类似的结果。

When butacarb was incubated with mouse liver 10,000xg supernatant, eleven metabolites were detected. Hydrolysis produced only 6 phenols. One of these, the major metabolite, was identified as 3,5-di-tert-butylphenol. Other metabolites were characterized but not all were completely identified: two acid metabolites containing a carboxyl & carbamoyl group; two containing a carbamoyl & two hydroxy groups (but not dihydroxybenzenoid); a hydroxybutylphenol; one containing a carbamoyl & hydroxy group; two dihydroxybutylphenols; n-hydroxymethyl butacarb; & n-hydroxymethyl hydroxybutyl analog. Studies with housefly (musca domestica), blowfly (lucilia sericata) & grass grubs (costelytra zealandica) gave results quant similar to those with mouse liver enzymes.

来源:Hazardous Substances Data Bank (HSDB)

代谢

...巴卡arb...通过肝脏微粒体中的酶系统裂解成酚类产物，这需要NADPH并会被一氧化碳抑制...这可能是...微粒体单加氧酶在'水解'氨基甲酸盐方面非常重要。

...Butacarb.../is/ cleaved to phenolic products by enzyme system in liver microsomes, which requires nadph & is inhibited by carbon monoxide...it is likely that this...microsomal mono-oxygenation is very important in 'hydrolysis' of carbamates.

来源:Hazardous Substances Data Bank (HSDB)

代谢

杀虫剂碳酰胺酯的主要代谢途径是氧化，通常与存在于多种组织中的混合功能氧化酶（MFO）酶相关。/碳酰胺类杀虫剂/

The principal route of metabolism of insecticidal carbamate esters is oxidative and is generally associated with the mixed-function oxidase (MFO) enzymes, which are present in several tissues. /Carbamate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

代谢

3,5-二叔丁基苯基-N-甲基氨基甲酸酯（布他卡伯）在昆虫和鼠肝酶中的代谢被研究。用三氚（H-3）标记的布他卡伯与鼠肝或家蝇和绿头蝇酶制剂的上清液（重力加速度的10,000倍）进行孵化，这些酶制剂来自它们的腹部。反应混合物被分析以寻找代谢物。在每个物种中检测到了11种氧化产物。在活体实验中，成年家蝇和绿头蝇通过局部给药方式用H-3标记的布他卡伯处理。然后将昆虫与沙子和乙醚一起研磨提取。乙醚提取物被检查以寻找代谢物。水溶性馏分也被检查。两个馏分都是由复杂的混合物组成。乙醚馏分用氢氧化钠水解，水溶性部分进行分析。检测到了六种酚类代谢物。主要的酚类产物是3,5-二叔丁基酚，它占据了超过半数的剂量。

The metabolism of 3,5-di-tert-butylphenyl-N-methylcarbamate (butacarb) was studied in insects and mouse liver enzymes. Tritium (H-3) labeled butacarb was incubated with 10,000 times the force of gravity supernatants from mouse liver or housefly and blowfly enzyme preparations, obtained from their abdomens. The reaction mixtures were analyzed for metabolites. Eleven oxidation products were detected in each species. In-vivo, adult houseflies and blowflies were dosed topically with H-3 labeled butacarb. The insects were then extracted by grinding them with sand and ether. Ether extracts were examined for metabolites. The water soluble fraction was also examined. Both fractions consisted of complex mixtures. The ether fraction was hydrolyzed with sodium-hydroxide, and the water soluble portion was analyzed. Six phenolic metabolites were detected. The major phenolic product was 3,5-di-tert-butylphenol, which accounted for more than half of the dose.

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

丁卡膦酸是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。碳酰胺通过与酶的活性位点进行碳酰胺化，形成不稳定的复合物与胆碱酯酶。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增多。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。

Butacarb 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、衰竭和抽搐。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。长期高剂量（>10年）暴露会导致神经心理学后果，包括感知和视觉运动处理方面的障碍（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，而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很明显。瞳孔收缩伴有视力模糊、不协调、肌肉抽搐和言语不清的情况也有报道。(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

活体研究表明，氨基甲酸酯在通过胃肠道的正常转运过程中几乎被完全吸收。...在 mice 中，所有氨基甲酸酯都迅速分布到组织和器官中。氨基甲酸酯的渗透半衰期值从 8-17 分钟不等。 ...在动物中，氨基甲酸酯的氧化通常，但不总是，导致解毒。氧化代谢通常导致极性更大、水溶性更高的产物，这些产物比母体化合物更容易通过尿液和粪便排出。/氨基甲酸酯类杀虫剂/

In vivo studies have shown that carbamates are almost completely absorbed during normal transit through the gastrointestinal tract. ...In mice, all carbamates were rapidly distributed to the tissues and organs. The half-life values of penetration ranged from 8-17 min for carbamates. ...In animals, oxidation of carbamates often, but not always, results in detoxification. Oxidative metabolism generally leads to products of greater polarity and water solubility, and these can be more readily eliminated through the urine and feces than the parent compound. /Carbamate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

关于通过吸入或口服途径暴露后，氨基甲酸盐在哺乳动物的各种器官和组织中的分布，目前可用的信息很少。据报道含有残留物的器官包括肝脏、肾脏、大脑、脂肪和肌肉。在大鼠中，半衰期约为3-8小时。看来人类通过尿液排出氨基甲酸盐的速度也很快，而且人类的代谢途径与大鼠相同。/氨基甲酸酯类杀虫剂/

Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2924199090

制备方法与用途

类别：农药

毒性分级：中毒

急性毒性：

• 大鼠口服 LD50：1800 毫克/公斤
• 小鼠口服 LD50：3200 毫克/公斤

可燃性危险特性：燃烧时产生有毒氮氧化物气体

储运特性：应存放在通风、低温和干燥的库房中，并与食品原料分开储存及运输

灭火剂：干粉、泡沫或砂土

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。