巴拉松 | 56-38-2

• 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: 巴拉松
• 中文别名: O,O-二乙基-O-(对硝基苯基)-硫代磷酸酯；乙基对硫磷；O,O-二乙基-O-(4-硝基苯基)硫代磷酸酯；硝苯硫磷酯；对硫磷；对硫磷-乙基
• 英文名称: parathion
• 英文别名: ethyl parathion；parathion-ethyl；O,O-diethyl O-p-nitrophenyl phosphorothioate；diethoxy-(4-nitrophenoxy)-sulfanylidene-λ5-phosphane
• CAS: 56-38-2
• 化学式: C₁₀H₁₄NO₅PS
• mdl: MFCD00036219
• 分子量: 291.265
• InChiKey: LCCNCVORNKJIRZ-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  1. 在碱性介质中迅速水解；在中性或微酸溶液中较为稳定；对紫外光与空气都不稳定。

  稳定性：非常稳定 [16]

  禁配物：强氧化剂、碱类 [17]

  应避免接触的条件：受热 [18]

  聚合危害：不会发生聚合 [19]

  分解产物：氧化磷、氧化硫 [20]

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

ADMET

代谢

... 对硫磷的新陈代谢在多种生物体中得到了广泛的研究，包括微生物、植物、昆虫和哺乳动物。其生物转化/依赖于氧化激活，通过将硫代硫原子替换为氧原子以产生毒性。与这种中毒反应竞争的是水解反应，导致解毒。环上的硝基团也可以被还原，特别是在牛瘤胃液中，还原为氨基团；这导致氨基对硫磷的产生... 氧化激活主要发生在肝脏。许多研究已经表明，在肝脏微粒体混合功能氧化酶系统中，还原型烟酰胺腺嘌呤二核苷酸磷酸和氧气的存在是负责这一反应的。已经证明，对硫磷转化为对氧磷可以在体内和体外发生。导致对硫磷解毒的降解反应涉及脱芳基化。产生的二甲磷酰基酸基本上是无毒的。

THE METABOLISM OF ... PARATHION ... HAS BEEN EXTENSIVELY STUDIED IN A WIDE VARIETY OF ORGANISMS, INCL MICROORGANISMS, PLANTS, INSECTS & MAMMALS. ... /ITS BIOTRANSFORMATION/ DEPENDS ON OXIDATIVE ACTIVATION BY REPLACEMENT OF THIONO SULFUR WITH OXYGEN FOR ... TOXICITY. COMPETING WITH THIS INTOXICATION REACTION ARE HYDROLYSIS REACTIONS THAT RESULT IN DETOXIFICATION. THE RING NITRO GROUP CAN ALSO BE REDUCED, PARTICULARLY IN BOVINE RUMEN FLUID, TO AMINO GROUP; THIS RESULTS IN AMINO PARATHION ... OXIDATIVE ACTIVATION TAKES PLACE PRIMARILY IN LIVER. A NUMBER OF ... /STUDIES/ HAVE SHOWN THAT, IN LIVER MICROSOMAL MIXED FUNCTION OXIDASE SYSTEMS, PRESENCE OF REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE & OXYGEN ARE RESPONSIBE FOR THIS REACTION. THE CONVERSION OF PARATHION TO PARAOXON HAS BEEN DEMONSTRATED ... IN VIVO & IN VITRO. DEGRADATIVE REACTIONS THAT RESULT IN DETOXIFICATION OF PARATHION ... INVOLVE ... DEARYLATION. THE RESULTING ... DIMETHYL PHOSPHORIC ACIDS ARE ESSENTIALLY NONTOXIC.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尽管对硫磷的主要降解反应是通过氧化成氧和通过水解成对硝基酚，但在来自雌性白化S-D大鼠肝细胞的微粒体中观察到了对硫磷还原成氨对硫磷和氧化成氨对氧磷。对硫磷还可以通过亚硝基对硫磷，在植物（如菠菜）中相继还原成羟基氨对硫磷。

Although the main degradation reaction of parathion is preceded by oxidation to oxon and by hydrolysis to p-nitrophenol, reduction to aminoparathion and oxidation to aminoparaoxon have been observed in microsomes /from female albino S-D rat liver cells; rat liver mitochondrial subfraction/. Parathion is also reduced to aminoparathion through nitrosoparathion, and hydroxyamino parathion successively in plants /such as spinach/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

动物中/对硫磷代谢的主要代谢产物/包括4-硝基苯磷酸、二乙基硫代磷酰氢酸、二乙基氢磷酸和p-硝基酚。...导致二乙基硫代磷酰氢酸和p-硝基酚形成的反应需要相同的辅因子.../例如/，氧气和还原型烟酰胺腺嘌呤二核苷酸，就像对硫磷生物转化为4-硝基苯磷酸一样。

MAJOR METABOLIC PRODUCTS /OF PARATHION METABOLISM IN ANIMALS/ INCL 4-NITROPHENYL PHOSPHATE, DIETHYL HYDROGEN PHOSPHOROTHIONATE, DIETHYL HYDROGEN PHOSPHATE & P-NITROPHENOL. ... THE REACTION RESULTING IN THE FORMATION OF DIETHYL HYDROGEN PHOSPHOROTHIONATE & P-NITROPHENOL REQUIRES THE SAME COFACTORS ... /SUCH AS/, OXYGEN & REDUCED NICOTINAMIDE ADENINE DICUCLEOTIDE , AS THE BIOTRANSFORMATION OF PARATHION INTO 4-NITROPHENYL PHOSPHATE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

幼鼠HOLTZMAN大鼠，雄性和雌性，被注射了对硫磷。采用反相层析法鉴定了组织残留物/包括/...二乙基磷酸盐，二乙基磷硫代硫酸盐，对氧磷和对硫磷。尽管肝脏、肾脏、骨骼肌和血浆含有所有四种化合物的残留物，但只有对硫磷和对氧磷在脑组织和脂肪组织中被发现。尿液中以DEPA和DEPTA为主要代谢物，对硫磷和对氧磷仅以微量存在。...离体实验使用肝脏匀浆表明，成年雄性大鼠对对硫磷的氧化和水解途径的活性高于幼鼠或成年雌性。

WEANLING HOLTZMAN RATS, MALE & FEMALE, WERE INJECTED WITH PARATHION. COCHROMATOGRAPHY WAS USED TO IDENTIFY TISSUE RESIDUES /WHICH CONSISTED/ ... OF DIETHYLPHOSPHORATE, DIETHYL PHOSPHOROTHIOATE, PARAOXON & PARATHION. WHEREAS LIVER, KIDNEY, SKELETAL MUSCLE & PLASMA CONTAINED RESIDUES OF ALL FOUR COMPOUNDS, ONLY PARATHION & PARAOXON WERE FOUND IN BRAIN & FAT TISSUES. DEPA & DEPTA OCCURRED AS THE MAJOR METABOLITES IN URINE WITH PARATHION & PAROXON PRESENT AS TRACES ONLY. ... IN VITO STUDIES WITH LIVER HOMOGENATES SHOWED THAT ADULT MALE RATS POSSESS HIGHER ACTIVITY THAN WEANLINGS OR ADULT FEMALES FOR BOTH THE OXIDATIVE & HYDROLYTIC PATHWAYS OF PARATHION.

来源:Hazardous Substances Data Bank (HSDB)

代谢

对硫磷已知的人类代谢物包括对氧磷。

Parathion has known human metabolites that include Paraoxon.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

对硫磷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累并继续作用，使得任何神经冲动不断传输，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。

Parathion 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

• 致癌性证据

致癌性分类：1）人类证据：无足够数据；2）动物证据：有限。对人类致癌风险的总体评估为第3组：该物质对人类致癌性不可分类。/来自表格/

Classification of carcinogenicity: 1) evidence in humans: no adequate data; 2) evidence in animals: limited. Overall summary evaluation of carcinogenic risk to humans is Group 3: The agent is not classifiable as to its carcinogenicity to humans. /From table/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：C组可能的人类致癌物

Cancer Classification: Group C Possible Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：C；可能的人类致癌物。分类依据：在一项研究中，奥斯本-门德尔雌性和雄性大鼠肾上腺皮质肿瘤增加，雄性大鼠甲状腺滤泡腺瘤和胰岛细胞癌呈阳性趋势。人类致癌性数据：无。动物致癌性数据：有限。

CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Increased adrenal cortical tumors in female and male Osborne-Mendel rats and positive trends for thyroid follicular adenomas and pancreatic islet-cell carcinomas in male rats in one study. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4；不可归类为人类致癌物。

A4; Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 吸收后迅速在系统内/动物/分布。 ... 观察到的仅有的组织积累是对酯酶酶的不可逆结合。

... RAPIDLY TRANSPORTED THROUGHOUT SYSTEM /OF ANIMALS/ AFTER ABSORPTION. ... ONLY TISSUE ACCUMULATION OF PARATHION ... THAT HAS BEEN OBSERVED IS IRREVERSIBLE BINDING TO ESTERASE ENZYMES.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

对硫磷可以通过皮肤、肠道和吸入被吸收。在小鼠中，对硫磷通过肠道的吸收速度是通过皮肤的的两倍。在小鼠皮下注射(32)P标记的对硫磷后，放射自显影显示其吸收非常缓慢，血液中的放射性活性水平较低。最高的活性出现在唾液腺和颈脂肪中，其次是肝脏、肾脏、胃壁、甲状腺、脾脏和肺。在中枢神经系统、肌肉组织和骨髓中记录到的活性较低。比较了兔子的静脉输注和经皮吸收对硫磷及其代谢物对氧磷的吸收率：对氧磷的吸收速度约比对硫磷快5倍...

PARATHION IS ABSORBED THROUGH SKIN, THE GUT, & BY INHALATION. IN MICE, PARATHION IS ABSORBED TWICE AS RAPIDLY THROUGH THE GUT AS THROUGH THE SKIN. AFTER SC INJECTIONS OF (32)P PARATHION TO MICE, AUTORADIOGRAPHY SHOWED IT TO BE VERY SLOWLY ABSORBED, WITH LOW LEVEL OF RADIOACTIVITY IN THE BLOOD. HIGHEST ACTIVITY APPEARED IN SALIVARY GLANDS & CERVICAL FAT, FOLLOWED BY LIVER, KIDNEY, GASTRIC WALL, THYROID, SPLEEN, & LUNG. LESS ACTIVITY WAS NOTED IN CNS, MUSCULATURE & BONE MARROW. PERCUTANEOUS ABSORPTION RATES OF PARATHION & ITS METABOLITE PARAOXON WERE USED TO COMPARE IV INFUSION & DERMAL ABSORPTION IN RABBITS: PARAOXON WAS ABSORBED ABOUT 5 TIMES MORE RAPIDLY ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... parathion在因过量中毒的母亲死胎中被鉴定出来这一事实，是胎盘转移的强烈证据...

... THE FACT THAT PARATHION HAS BEEN IDENTIFIED IN DEAD FETUSES OF MOTHERS POISONED WITH OVERDOSE IS STRONG EVIDENCE FOR ... PLACENTAL TRANSFER ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

敌百虫及其代谢物在长期处理的奶牛牛奶中未被发现... @ ... 水平高达32毫克/千克体重/天。

PARATHION & PARATHION METABOLITES COULD NOT BE DETECTED IN MILK OF COWS CHRONICALLY TREATED ... @ ... LEVELS UP TO 32 MG/KG BODY WT/DAY.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

1. 由二乙基硫代磷酰氯在三甲胺催化下与对硝基酚钠合成得到。原料消耗定额：五硫化二磷370kg/t、无水乙醇330kg/t、对硝基酚钠330kg/t。
2. 同样由二乙基硫代磷酰氯在三甲胺催化下与对硝基酚钠合成制得。

合成制备方法

1. 由二乙基硫代磷酰氯在三甲胺催化下与对硝基酚钠合成得到。原料消耗定额：五硫化二磷370kg/t、无水乙醇330kg/t、对硝基酚钠330kg/t。
2. 同样由二乙基硫代磷酰氯在三甲胺催化下与对硝基酚钠合成制得。

用途简介

1. 对硫磷是一种广谱性杀虫剂，具有触杀、胃毒和熏蒸作用，无内吸传导作用，但能渗透入植物体内。它对昆虫的作用很快，在高温时杀虫效果更显著。可用于防治棉花、苹果、柑桔、梨、桃等果树害虫及麦红蜘蛛等。
2. 对硫磷是一种广谱性高毒杀虫剂，并兼有杀螨作用，具有强烈的触杀和胃毒作用，有一定熏蒸作用，无内吸作用但有较强的渗透作用。它可防治水稻、棉花和果树等作物上的多种害虫，特别是对水稻螟虫、棉铃虫、玉米螟、高粱条螟等有害昆虫的防治效果显著。此外，还用于防治三化螟、二化螟、大螟。但在蔬菜、茶叶、果树及中草药上禁用；瓜类对对硫磷敏感，尤其幼苗易受药害，不建议使用。食用作物收获前30天内禁止使用。
3. 对硫磷可用作农药杀虫剂和杀螨剂。

用途

1. 对硫磷是一种广谱性杀虫剂，具有触杀、胃毒和熏蒸作用，无内吸传导作用但能渗透入植物体内。它对昆虫的作用很快，在高温时杀虫效果显著增加，可用于防治棉花、苹果、柑桔、梨、桃等果树害虫及麦红蜘蛛。
2. 对硫磷是一种广谱性高毒杀虫剂，并兼有杀螨作用，具有强烈的触杀和胃毒作用，有一定熏蒸作用无内吸作用但有较强的渗透作用。可用于防治水稻、棉花和果树等作物上的多种害虫，特别是对水稻螟虫、棉铃虫、玉米螟、高粱条螟等的防治效果显著。但它在蔬菜、茶叶、果树及中草药上禁用；瓜类对对硫磷敏感，尤其是幼苗易受药害不可使用。食用作物收获前30天内禁止使用。
3. 对硫磷可用作农药杀虫剂和杀螨剂。[22]

反应信息

• 作为反应物：
  描述：

  巴拉松 在 catalyst from bacopa monnieri/CuCl₂ 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 O,O-二乙基O-氢硫代磷酸酯
  参考文献：
  名称：

  USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS

  摘要：

  金属积累植物用于实现化学反应，特别是催化反应的使用。

  公开号：

  US20150376224A1
• 作为产物：
  描述：

  双乙烯酮 、 1-乙酰哌嗪 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到巴拉松
  参考文献：
  名称：

  Fe(III) Complex Compounds For The Treatment And Prophylaxis Of Iron Deficiency Symptoms And Iron Deficiency Anemias

  摘要：

  这项发明涉及铁（III）配合物和包括它们的药物组合物，用作药物，特别是用于治疗和/或预防缺铁症状和缺铁性贫血。

  公开号：

  US20130109662A1
• 作为试剂：
  描述：

  苯甲酸,二羟基- 在 氢氧化钾 、 sodium tetrahydroborate 、 二甲基硫 、 巴拉松 、 水 、 1-羟基苯并三唑 、 臭氧 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Conformationally Rigid Tricyclic Tripods: Synthesis and Application to Preparation of Enterobactin Analogs

  摘要：

  The syntheses of the conformationally rigid triol 2 and triamine 3 are described. One of the key features of these syntheses was that each of the intermediates involved contained a symmetry element, which made their structure elucidation facile and conclusive. The structural similarity between the platform of enterobactin in its metal binding state and triamine 3 was recognized, and the enterobactin analog 14 was synthesized. The K-f value observed for 14 was as high as the K-f value for enterobactin itself, and higher than the K-f value for any enterobactin analog ever reported. In comparison with a number of synthetic enterobactin analogs, it became evident that the conformational rigidity of the enterobactin platform, resulting in good preorganization of the three catechol moieties toward Fe(III)-chelation, was an important factor contributing to its extraordinarily high K-f.

  DOI：

  10.1021/jo00104a043

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] 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。

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