乙基(Z)-N-苄基-N-[(甲基(1-甲硫基亚乙基氨基-氧羰基)氨基)硫]-Β丙氨酸酯 | 83130-01-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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: 乙基(Z)-N-苄基-N-[(甲基(1-甲硫基亚乙基氨基-氧羰基)氨基)硫]-Β丙氨酸酯
• 中文别名: 农虫威；棉铃威
• 英文名称: alanycarb
• 英文别名: ethyl (Z)-N-benzyl-N-[{methyl(1-methylthioethylideneamino-oxycarbonyl)amino}thio]-β-alaninate；ethyl 3-[benzyl-[methyl-[(Z)-1-methylsulfanylethylideneamino]oxycarbonylamino]sulfanylamino]propanoate
• CAS: 83130-01-2
• 化学式: C₁₇H₂₅N₃O₄S₂
• 分子量: 399.535
• InChiKey: GMAUQNJOSOMMHI-JXAWBTAJSA-N

物化性质

• 熔点：
  47～52℃
• 沸点：
  506.2±60.0 °C(Predicted)
• 密度：
  1.18
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 蒸汽压力：
  3.50e-08 mmHg

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

ADMET

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

Alanycarb 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、腹痛和腹泻常常是显著的症状。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，以使肌肉或器官得以放松。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，使得任何神经冲动持续传递，肌肉收缩不会停止。

Alanycarb 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)

安全信息

• 危险品标志：
  T+,N
• 安全说明：
  S28,S36/37,S45,S61
• 危险类别码：
  R22,R26,R50
• WGK Germany：
  3

制备方法与用途

化学性质

棉铃威纯品为晶体，熔点46.6~47.0℃。其蒸气压小于0.0047mPa（20℃），相对密度1.29（20℃）。油水分配系数Kow-lgP值为3.57±0.06。在20℃下，水中溶解度为29.6mg/L；而在甲苯、二氯甲烷、甲醇、丙酮和乙酸乙酯中的溶解度均超过1000g/L。棉铃威在100℃以下稳定，在54℃时30天分解0.2%~1.0%。中性和弱碱条件下较为稳定，但在酸性或强碱性环境中不稳定，在日光下玻璃板上的半数致死时间（DT50）为6小时。

毒性

雄性大鼠急性经口LD₅₀值为440mg/kg；雄性大鼠急性经皮LD₅₀大于2000mg/kg。对兔眼睛有轻微刺激，但对兔皮肤无刺激作用。大鼠吸入LC₅₀（4小时）大于205mg/m³空气。在2年的大鼠实验中，NOEL值为30mg/kg饲料；建议每日摄入量（ADI）为0.011mg/kg。棉铃威在大鼠和兔Ames试验中未显示致突变性。

作用机理

棉铃威具有触杀和胃毒作用。

应用

棉铃威适用于蔬菜、葡萄、棉花、烟草、蔓生植物及柑橘等作物，主要用于防治鞘翅目、缨翅目、半翅目、鳞翅目及其他害虫。

合成方法

CH₃C(SCH₃)NOC(O)NHCH₃与cis-N(CH₂CH₂COOC₂H₅)CH₂C₆H₅及三乙胺在二氯甲烷中反应2小时，即可制得棉铃威。反应式如下：

[ \text{CH}_3\text{C}(S\text{CH}_3)\text{NOC(O)NH}\text{CH}_3 + \text{cis-N(CH}_2\text{CH}_2\text{COO}\text{C}_2\text{H}_5\text{)}\text{CH}_2\text{C}_6\text{H}_5 + 3\text{Et}_3\text{N} \xrightarrow{\text{二氯甲烷}} \text{棉铃威} ]

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] 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] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [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。

表征谱图