Butoxycarboxim | 34681-23-7

• 物质功能分类: 分析化学 - 标准品 - 农残、兽药及化肥类
• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: Butoxycarboxim
• 英文别名: [(E)-3-methylsulfonylbutan-2-ylideneamino] N-methylcarbamate
• CAS: 34681-23-7
• 化学式: C₇H₁₄N₂O₄S
• 分子量: 222.26
• InChiKey: CTJBHIROCMPUKL-WEVVVXLNSA-N

物化性质

• 熔点：
  83°C
• 密度：
  1.3816 (rough estimate)
• 颜色/状态：
  Colorless crystal
• 溶解度：
  Readily soluble in polar organic solvents; slightly soluble in non-polar solvents; solubility (g/l @ 20 °C): in chloroform 186, acetone 172, isopropanol 101, toluene 29, carbon tetrachloride 5.3, cyclohexane 0.9, heptane 0.1
• 蒸汽压力：
  2.0X10-6 mm Hg @ 20 °C /Technical/
• 稳定性/保质期：

  Stable to u.v. light. Thermally stable up to 100 °C.

• 分解：
  When heated to decomposition it emits very toxic fumes of /nitrogen and sulfur oxides/

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

甲酸酯类化合物的新陈代谢的第一步是水解成甲酸，然后甲酸分解成二氧化碳（CO2）和相应的胺。N-甲基和N, N-二甲基衍生物的水解机制不同。N-甲基甲酸酯通过异氰酸中间体，而在N, N-二甲基甲酸酯的水解中，会形成一个加成产物，即羟基离子，产生醇和N-二甲基取代的酸。酯酶催化的水解速率在哺乳动物中比植物和昆虫快。除了水解，还会发生氧化，包括：芳香环的羟基化，O-脱烷基化，N-甲基羟基化，N-脱烷基化，脂肪侧链的氧化以及亚砜化成相应的砜。氧化与混合功能氧化酶（MFO）酶有关。在哺乳动物中，结合作用会导致O-和N-葡萄糖苷酸、硫酸盐和巯基尿酸衍生物的形成。糖苷和磷酸盐是在植物中更常见的结合产物。/甲酸酯类杀虫剂/

The first step in the metabolism of carbamates is hydrolysis to carbamic acid, which decomposes to carbon dioxide (CO2) and the corresponding amine. The mechanism of hydrolysis is different for N -methyl and N -dimethyl derivatives. The N -methyl carbamates pass through an isocyanate intermediate, whereas in the hydrolysis of N - dimethylcarbamates, an addition product with a hydroxyl ion is formed yielding the alcohol and N -dimethyl substituted acid. The rate of hydrolysis by esterases is faster in mammals than in plants and insects. Apart from hydrolysis, oxidation also takes place including: hydroxylation of the aromatic ring, O -dealkylation, N -methyl hydroxylation, N -dealkylation, oxidation of aliphatic side chains, and sulfoxidation to the corresponding sulfone. Oxidation is associated with the mixed-function oxidase (MFO) enzymes. Conjugation leads to the formation of O - and N -glucuronides, sulfates, and mercapturic acid derivatives in mammals. Glycosides and phosphates are conjugation products more common in plants. /Carbamate Pesticides/

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲酰胺通过肝脏酶促水解；降解产物由肾脏和肝脏排出。

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

丁氧羧酸是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。碳酸酯通过与酶的活性位点上的羧基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流泪。在更高剂量的暴露下，头痛、流涎、恶心、呕吐、腹痛和腹泻通常是显著的。乙酰胆碱酯酶分解在神经和肌肉接头释放的神经递质乙酰胆碱，以允许肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动不断传递，肌肉收缩不会停止。

Butoxycarboxim 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

在哺乳动物中，口服给药后，药物以其原形和代谢物形式在尿液中排出。

In mammals, following oral administration, eliminated in the urine both in the unchanged form and as metabolites.

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

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3

制备方法与用途

化学性质

丁酮飙威含有(E)-和(Z)-异构体（比例为85~90%:15~10%），呈现无色晶体状。其熔点在85~89℃之间，纯的(E)-异构体的熔点为83℃。在20℃时，蒸气压为0.266毫帕，密度为1.21克/立方厘米（20℃）。亨利常数为2.83×10⁻⁷ Pa·m³/mol。水中溶解度在20℃时为209克/升；其他溶剂中的溶解度如下：丙酮172，四氯化碳5.3，氯仿186，环己烷0.9，庚烷0.1，异丙醇101，甲苯29。丁酮砜威易溶于极性有机溶剂，微溶于非极性溶剂，并在≤100℃时保持热稳定性。其水溶液的半数致死时间（DT₅₀）分别为pH 5时501天、pH 7时18天和pH 9时16天。此外，丁酮砜威对紫外线稳定。

毒性

丁酮飙威通过口服对大鼠的半数致死剂量（LD₅₀）为458毫克/千克，兔子的这一数值为275毫克/千克。经皮接触方面，大鼠的LD₅₀大于2000毫克/千克。长期喂食实验中，在300毫克/千克饲料的条件下对大鼠无明显毒性，但1000毫克/千克饲料会导致红细胞和血浆胆碱酯酶轻微抑制作用。胶纸板黏着制剂通过口服对大鼠的LD₅₀大于5000毫克/千克，而雌鼠的急性经皮半数致死剂量为288毫克/千克。丁酮砜威是丁酮飙威在动植物组织中的代谢产物，因此其对后者的毒性实验包括部分丁酮飙威。

作用机理

丁酮砜威是一种胆碱酯酶抑制剂，具有触杀和胃毒作用的内吸性杀虫剂。它通过根部吸收后向植株顶部迁移。

应用

丁酮砜威可用于：

• 适用作物：观赏性植物。
• 防治对象：蚜虫、叶螨等。

合成方法

丁酮砜威可通过丁酮飙威氧化合成。具体步骤如下（图中展示）：

文献信息

• [EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
  申请人：BASF SE

  公开号：WO2014206910A1

  公开（公告）日：2014-12-31

  The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及公式（I）中变量如索权和说明中所定义的自行车基取代异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包含所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] AZOLINE COMPOUNDS<br/>[FR] COMPOSÉS AZOLINE
  申请人：BASF SE

  公开号：WO2015128358A1

  公开（公告）日：2015-09-03

  The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式（I）的噁唑啉化合物，其中A、B1、B2、B3、G1、G2、X1、R1、R3a、R3b、Rg1和Rg2如权利要求和描述中所定义。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料、农业和兽医组合物。
• [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。