氯唑磷 | 42509-80-8

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机磷杀虫剂
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 中文名称: 氯唑磷
• 中文别名: 异丙三唑磷；O,O-二乙基-O-(5-氯-1-四基乙基-1上,2,4-三唑-3-基)硫代磷酸酯；米乐尔；O-5-氯-1-异丙基-1H-1,2,4-三唑-3-基-O,O-二乙基硫代磷酸酯；O,O-二乙基-O-(5-氯代-1-异丙基-1,2,4三唑-3-基)硫代磷酸酯
• 英文名称: isazophos
• 英文别名: isazofos；Brace；(5-chloro-1-propan-2-yl-1,2,4-triazol-3-yl)oxy-diethoxy-sulfanylidene-λ5-phosphane
• CAS: 42509-80-8
• 化学式: C₉H₁₇ClN₃O₃PS
• mdl: MFCD00078699
• 分子量: 313.745
• InChiKey: XRHGWAGWAHHFLF-UHFFFAOYSA-N

物化性质

• 熔点：
  <25℃
• 沸点：
  bp0.001 100°; bp760 170°
• 密度：
  1.22 g/cm3 (20℃)
• 颜色/状态：
  Amber liquid
• 溶解度：
  In water, 69 mg/l at 20 °C
• 蒸汽压力：
  8.70X10-5 mm Hg at 25 °C
• 分解：
  Decomposes above 200 degrees C.
• 解离常数：
  pKa=4.0
• 保留指数：
  1795.8
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。 该物质对皮肤有刺激作用。动物实验结果显示，它无致畸、致癌或致突变作用，繁殖试验也未见异常。此外，它对鸟类、鱼类和蜜蜂具有高毒性。

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  6

ADMET

代谢

有机磷杀虫剂的代谢主要通过氧化、酯酶的水解以及分子片段转移到谷胱甘肽上。有机磷杀虫剂的氧化可能产生或多或少有毒的产品。谷胱甘肽转移酶反应产生的产品在大多数情况下毒性较低。水解和转移酶反应影响硫代酯和它们的氧硫化合物。/有机磷杀虫剂/

Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both thioates and their oxons. /Organophosphorus Pesticides/

来源:Hazardous Substances Data Bank (HSDB)

代谢

有机磷化合物的代谢主要通过氧化、通过酯酶的水解以及与谷胱甘肽反应进行。去甲基化和葡萄糖醛酸化也可能发生。有机磷农药的氧化可能导致产生中等毒性的产物。一般来说，磷酰硫酯本身并不直接有毒，但需要通过氧化代谢转化为近端毒素。谷胱甘肽转移酶反应产生的产物在大多数情况下毒性较低。对氧磷酶（PON1）是有机磷化合物代谢中的关键酶。PON1可以通过水解使一些有机磷化合物失活。PON1水解多种有机磷杀虫剂以及神经毒剂（如梭曼、沙林和VX）的活性代谢物。PON1的多态性导致该酯酶的酶水平和催化效率不同，这反过来表明不同个体可能更容易受到有机磷暴露的毒性影响。

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

Isazofos 是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）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大的神经毒素，低剂量时会导致过度流涎和流泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，后者在神经和肌肉接头处释放，以使肌肉或器官放松。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。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计用来结合到酶的活性位点上。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐）以及一个末端的氧。

Isazofos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. 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. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

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

急性接触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，如果呼吸肌受到影响，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尼古丁受体的过度刺激。当这种情况发生时，可以看到肌肉无力、疲劳、肌肉痉挛、肌束震颤和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中尼古丁受体的过度刺激。与此相关的症状包括高血压和低血糖。由于乙酰胆碱积累，中枢神经系统中尼古丁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。当由于乙酰胆碱过量在毒蕈碱乙酰胆碱受体上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。对于男性和女性的生育、生长和发育，某些生殖效应与有机磷农药暴露有特定联系。关于生殖效应的大多数研究都是在农村地区使用农药和杀虫剂的农民中进行的。在女性中，月经周期紊乱、怀孕时间延长、自然流产、死产以及后代的一些发育效应与有机磷农药暴露有关。产前暴露与胎儿生长和发育受损有关。神经毒性效应也与有机磷农药中毒有关，在人类中引起四种神经毒性效应：胆碱能综合症、中间综合症、有机磷诱导的迟发性多发性神经病（OPIDP）和慢性有机磷诱导的神经精神障碍（COPIND）。这些综合症在急性接触和慢性接触有机磷农药后出现。

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. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

低剂量暴露的症状包括过度流涎和眼泪。急性剂量症状包括严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、虚脱和抽搐。肌肉无力可能会逐渐加重，如果呼吸肌肉受累，可能会导致死亡。高血压、低血糖、焦虑、头痛、震颤和共济失调也可能发生。

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 副作用

其他毒物 - 有机磷

Other Poison - Organophosphate

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  T+,N
• 安全说明：
  S28,S36/37,S38,S45,S59,S61
• 危险类别码：
  R43,R24/25,R48/20,R26,R50/53
• WGK Germany：
  3
• 海关编码：
  2933990012
• 危险品运输编号：
  UN 3018
• 包装等级：
  II
• 危险类别：
  6.1(a)

制备方法与用途

毒性方面，大鼠急性经口LD₅₀值为40～60 mg/kg，急性经皮LD₅₀值为250～700 mg/kg，急性吸入LD₅₀值为250 mg/L（4小时）。该物质对皮肤有刺激作用。动物实验未显示致畸、致癌或致突变的效应，繁殖试验亦无异常结果。然而，它对鸟类、鱼类及蜜蜂具有高毒性。

化学性质上，纯品呈黄色液体状。沸点为100℃/0.1333帕斯卡，相对密度在20℃时约为1.22，折射率n₂₀D值为1.4867，蒸气压在20℃时为1.76×10⁻³帕斯卡。该物质可溶于甲醇、三氯乙烯等有机溶剂中，在水中的溶解度仅为每升150毫克。其在中性和酸性介质中较为稳定，但在碱性条件下易分解。

用途方面，此化合物用作杀虫和杀线虫剂，具有触杀、胃毒及内吸作用。适用于玉米、棉花、水稻、甜菜、草坪以及蔬菜等作物的害虫防治，尤其是针对长蝽象、线虫及水稻螟虫等。该物质既可用于叶面喷洒，也可作为土壤或种子处理使用，每公顷推荐施用量为0.5～2公斤。但因其对马铃薯可能产生药害，故不宜在马铃薯上使用。

生产方法包括异氰酸酯法、氯羰基胺二氯的制备、异丙基肼的合成以及异唑醇和氯唑磷的合成等步骤。具体过程较为复杂，涉及多个化学反应及精炼步骤。

另一种合成方法为尿素法或光气法，在此略去详细描述。

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。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。