苯硫膦 | 2104-64-5

• 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: 苯硫膦
• 中文别名: O-乙基-O-(对硝基苯基)苯基硫代膦酸酯；苯硫磷；伊皮恩；O-乙基-O-(4-硝基苯基)苯基硫代膦酸酯；苯硫磷酯；O-乙基-O-(4-硝基苯)苯基硫代膦酰酯；O-乙基-O-对-硝基苯基苯基硫逐膦酸酯；EPN-300；ENTl7798；EPH；伊皮恩
• 英文名称: EPN
• 英文别名: O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate；ethoxy-(4-nitrophenoxy)-phenyl-sulfanylidene-λ5-phosphane
• CAS: 2104-64-5
• 化学式: C₁₄H₁₄NO₄PS
• mdl: MFCD00055309
• 分子量: 323.309
• InChiKey: AIGRXSNSLVJMEA-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  在中性和酸性介质中稳定，但遇碱会分解。溶于多种有机溶剂，几乎不溶于水。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

代谢

在大鼠、豚鼠、小鼠、麻雀、鸡、吸盘鱼、鲈鱼、鲱鱼、比目鱼、太阳鱼、鲶鱼、杜父鱼和蓝鳃鱼中产生对氨基苯基乙基苯硫代磷酸酯。/来自表格/

Yields p-aminophenyl ethyl benzenethiophosphonate in rat, guinea pig, mouse, sparrow, chicken, sucker, bass, alewife, flounder, sunfish, bullhead, sculpin and bluegill. /from table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

Rabbit sera将导致硫的去除和p-硝基酚的水解。在EPN与nadph2、氧气以及大鼠、家蝇或兔肝的微体一起孵化后，每种情况下都发现了相应的酚。还产生了Oxon类似物。也观察到了一些oxon转化为相应酚的情况。

Rabbit sera brought about removal of sulfur and hydrolysis to p-nitrophenol. ...After incubation of EPN with nadph2, oxygen and microsomes of rat, housefly, or rabbit liver, corresponding phenol was found in each case. Oxon analog was also produced. Some conversion of oxon to corresponding phenol was also observed.

来源:Hazardous Substances Data Bank (HSDB)

代谢

.../对硝基酚/是由/EPN/氧化偶氮通过酯化裂解形成，或者直接通过初始在p=s位的氧化攻击引发的mono-oxygenase催化的脱芳香基作用从.../EPN/形成。

.../Para-nitrophenol/ is formed either by way of esteratic cleavage of the /EPN/ oxon or directly from .../EPN/ by mono-oxygenase-catalyzed dearylation prompted by initial oxidative attack at p=s.

来源:Hazardous Substances Data Bank (HSDB)

代谢

单次口服给予1周大的小鸡1毫克（2.7微居里/千克）的（14）C EPN后，其代谢产物包括O-乙基苯基膦酸、苯基膦酸和O-乙基苯基硫代膦酸。

Metabolism of single 1 mg (2.7 uci/kg) oral dose of (14)C EPN in 1 wk old chicks produced o-ethyl phenylphosphonic acid, phenylphosphonic acid, and o-ethyl phenylphosphonothioic acid.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4；不能归类为人类致癌物。

A4; Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该物质可以通过吸入其气溶胶、通过皮肤接触以及摄入进入人体。

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛刺激，皮肤刺激；瞳孔缩小，流泪；流鼻涕（流出稀薄的鼻腔粘液）；头痛；胸部紧缩，喘息，喉部痉挛；流涎；发绀；厌食，恶心，腹部绞痛，腹泻；瘫痪，抽搐；低血压，心律不齐。

irritation eyes, skin; miosis, lacrimation (discharge of tears); rhinorrhea (discharge of thin nasal mucus); headache; chest tightness, wheezing, laryngeal spasm; salivation; cyanosis; anorexia, nausea, abdominal cramps, diarrhea; paralysis, convulsions; low blood pressure, cardiac irreg

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 吸入症状

晕眩。瞳孔缩小。肌肉痉挛。过度流涎。出汗。肌肉抽搐。恶心。

Dizziness. Pupillary constriction. Muscle cramps. Excessive salivation. Sweating. Muscle twitching. Nausea.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

EPN经口或经皮暴露后容易被吸收。在大鼠中，单次口服1.5 mg/kg EPN后，约61-68%的剂量通过尿液排出，7-21%的剂量通过粪便排出。代谢过程基本完成，因为尿液中的代谢物排出量占总剂量的60-68%，相应的粪便值为6.7-17.2%。在大鼠每隔24小时三次给予0.72或0.072 mg/kg EPN的情况下，14和26%的剂量以对硝基酚的形式通过尿液排出。在最后给药后任何时间点，血液中均未检测到EPN，但在给药第3天仅在脂肪组织中检测到（0.06 ppm）。

EPN is readily absorbed following either oral or dermal exposure. In rats, following a single oral dose of 1.5 mg/kg EPN, about 61-68% of the dose was excreted in urine and 7-21% of the dose was excreted in the feces. Metabolism was essentially complete because urinary excretion of metabolites totaled 60-68% of the total dose, the corresponding fecal values were 6.7-17.2%. ...In rats given 0.72 or 0.072 mg/kg EPN three times at 24 hr intervals, 14 and 26% of the dose was excreted as p-nitrophenol in urine. EPN was not detectable in blood at any time after the final dose but was detectable in adipose tissue (0.06 ppm) only on day 3.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

单次皮肤给药剂量为20.0 mg/kg的（14）C-EPN给予成年雄性猫后，放射性剂量以0.46/天的速率常数呈指数下降，对应的半衰期为1.5天。大部分放射性物质通过尿液排出（29.9%），仅有3.2%通过粪便排出。在呼出的CO2中没有检测到放射性。尿液中仅检测到少量的EPN，粪便中也仅检测到微量。给药后0.5天，在大脑、脊髓、坐骨神经、脂肪组织、血浆、肌肉、肝脏和肾脏中主要检测到的物质为EPN。给药4天后，肝脏和肾脏中的大部分放射性物质被鉴定为代谢物。EPN从血浆中消除的半衰期为9.1天。相对于血浆，EPN在坐骨神经中的相对滞留时间最长，在肾脏中最短。

Radioactivity of single dermal dose, 20.0 mg/kg of (14)C-EPN admin to adult male cats disappeared exponentially at rate constant of 0.46/day, corresponding to half-life of 1.5 days. Most of radioactivity was excreted in urine (29.9%); only 3.2% in feces. None was detected in expired CO2. Only traces of EPN were detected in urine and feces. EPN was major substance identified 0.5 day after admin in brain, spinal cord, sciatic nerve, adipose tissue, plasma, muscle, liver and kidney. Most radioactivity in liver and kidney after 4 days was identified as metabolites. Half-life of EPN elimination from plasma was 9.1 days. Relative residence of EPN relative to plasma was longest in sciatic nerve and shortest in kidney.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当一只老鼠在含有450 ppm EPN的饮食中预处理21天后，72小时内只有极少量的剂量残留在体内组织中。因此，EPN在老鼠体内实际上被完全代谢和排出。两只经过EPN处理的母鸡，在21天内每天接受2.5 mg/kg EPN，以及两只未经处理的母鸡，在72小时内排出了94-100%的单次口服、非神经毒性的4 mg/kg剂量。从处理过或未处理的鸡中排出的剂量没有显著差异。体内组织中残留少量EPN；在大脑和脊髓中仅发现微量。相比之下，单次口服神经毒性剂量50 mg/kg EPN被鸡缓慢代谢和排出。在72小时测试期间，只有65%的剂量被排出。排泄物提取物中含有在大鼠中发现的相同的五种代谢物。因此，50 mg/kg的剂量可能超出了肝脏解毒EPN的代谢能力。

When a rat was preconditioned for 21 days on a diet that contained 450 ppm EPN, only traces of the dose remained in body tissues after 72 hr. Thus, EPN was practically completely metabolized and eliminated in rats. Two EPN conditioned hens that received 2.5 mg/kg EPN for 21 days and two unconditioned hens excreted 94-100% of a single oral, nonneurotoxic 4 mg/kg dose with in 72 hr of admin. No significant difference was apparent in the dose excreted from conditioned or unconditioned chickens. Small amounts of EPN remained in body tissues; only trace amounts were found in the brain and spinal cord. By contrast, a single oral neurotoxic dose of 50 mg/kg EPN was slowly metabolized and excreted by chickens. Only 65% of the dose was eliminated during the 72 hr test. Excreta extract contained the same five metabolites found in the rat. Thus, the 50 mg/kg dose may have exceeded the metabolic capacity of the liver to detoxify EPN.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在猫身上，当单次剂量为20毫克/千克通过皮肤给药时，EPN被迅速吸收，这从应用部位EPN的消失得到反映。大部分被吸收的剂量通过尿液排出（29.9%）；3.2%在粪便中回收。在连续10天每天通过皮肤给药0.5毫克/千克EPN的猫中，总剂量的62%通过尿液排出。因此，猫身上EPN的代谢和毒物动力学介于大鼠和鸡之间。与大鼠类似，EPN作为极性代谢物排出，大部分在尿液中。然而，与鸡类似，EPN在猫组织中尤其是神经组织中持久存在。发现猫对EPN亚慢性皮肤暴露的敏感性比鸡低十倍，这可能归因于猫体内EPN相对较快的代谢和排出。

In cats, EPN was readily absorbed when a single dose of 20 mg/kg was dermally applied as reflected by disappearance of EPN from the application site. Most of the absorbed dose was excreted in urine (29.9%); 3.2% was recovered in the feces. In cats given daily dermal doses of 0.5 mg/kg EPN for 10 days, 62% fo the total dose was given daily dermal doses of 0.5 mg/kg EPN for 10 days, 62% of the total dose was eliminated in the urine. Thus, the metabolism and toxicokinetics of EPN in the cat are intermediate between those in the rat and in the chicken. Similarly to the rat, EPN is excreted as polar metabolite, mostly in the urine. As int he chicken, however, EPN is persistent in cat tissues, especially in nervous tissues. The finding that the cat is ten times less sensitive than the chicken to subchronic dermal exposure to EPN may be explained by the relatively rapid metabolism and elimination of EPN in the cat.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

含磷残留物可能通过尿液或粪便排出。一些结合的残留物会留在接触的动物体内。结合似乎主要发生在蛋白质上，而这些蛋白质的周转似乎与它们的半衰期有关。有限的数据表明，残留物并入DNA的量非常微小，并且不是通过直接烷基化，例如人们可能认为与遗传损害有关的方式。/有机磷农药/

...Elimination of the phosphorus-containing residue may be via the urine or feces. Some bound residues remain in exposed animals. Binding seems to be to proteins, principally, and the turnover appears to be related to the half-life of these proteins. There are limited data showing that incorporation of residues into DNA occurs only in trace amounts and not by direct alkylation, such as might be believed to be associated with genetic damage. /Organophosphorus Pesticides/

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

由对硝基酚钠与O-乙基苯基硫代磷酰氯反应而得。

合成制备方法

由对硝基酚钠与O-乙基苯基硫代磷酰氯反应而得。

用途简介

有机磷杀虫、杀螨剂。农药分析标准。苯硫磷系触杀杀虫杀螨剂，对多种害虫有效。用于防治水稻二化螟、三化螟、稻螟铃、叶蝉、飞虱、稻苞虫等均有很高的杀虫效力。

用途

有机磷杀虫、杀螨剂。农药分析标准。苯硫磷系触杀杀虫杀螨剂，对多种害虫有效。用于防治水稻二化螟、三化螟、稻螟铃、叶蝉、飞虱、稻苞虫等均有很高的杀虫效力。

反应信息

• 作为反应物：
  描述：

  苯硫膦 在 溴 作用下， 以 乙腈 为溶剂， 生成 牛津郡苯硫膦
  参考文献：
  名称：

  Oxidation of organophosphorus pesticides for the sensitive detection by a cholinesterase-based biosensor

  摘要：

  A potentiometric flow injection-type biosensor developed in our laboratory was used for the determination of organophosphorus pesticides (OPs). The principle of the biosensor is that the degree of inhibition of a sensor enzyme by an OP is dependent on the concentration of the pesticide. The sensor system consisted of a reactor with acetylcholinesterase (AChE) immobilized on a controlled pore glass and a detector with a tubular H+-selective membrane electrode. In order to examine the possibility of enhancing the sensitivity of the sensor by converting OPs to oxidized forms (stronger inhibitors), a comparison of the degree of enzyme inhibition by OPs at 10(-6) M before and after their oxidation was made. All of the ten pesticides tested exhibited greater inhibitory power toward the sensor enzyme following oxidation. All of the oxidized pesticides at 10(-6) M inhibited the sensor enzyme to a considerable degree, demonstrating the utility of the developed method for the class-specific determination of OPs. A calibration curve for diazinon, over the concentration range of 10(-11)-10(-4) M, was obtained. The lower detection limit was 2 x 10(-10) M. Treatment of the inhibited enzyme with pyridine-2-aldoxime restored the enzyme to near full activity, allowing repeated use of the sensor. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0045-6535(01)00005-4
• 作为产物：
  描述：

  对硝基苯酚 在 苄基三乙基氯化铵 sodium hydroxide 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 3.75h， 生成 苯硫膦
  参考文献：
  名称：

  Purnanand; Danikhel, R. K., Synthesis, 1983, # 9, p. 731 - 733

  摘要：

  DOI：

文献信息

• HYDRAZONYL GROUP-CONTAINING CONDENSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US20190177319A1

  公开（公告）日：2019-06-13

  An object of the present invention is to develop and provide a novel agricultural and horticultural insecticide in view of the still immense damage caused by insect pests etc. and the emergence of insect pests resistant to existing insecticides in crop production in the fields of agriculture, horticulture and the like. Provided is a hydrazonyl group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by the general formula (1): wherein R 1 represents, for example, an alkyl group, R 2 represents, for example, a hydrogen atom, R 3 and R 4 each represent, for example, an alkyl group, a haloalkyl group or an acyl group, A 1 represents, for example, a nitrogen atom, A 2 represents, for example, N-Me or an oxygen atom, A 3 represents, for example, a carbon atom or a nitrogen atom, A 4 represents, for example, C—H, m represents, for example, 2, and n represents, for example, 1}, or a salt thereof; an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

  本发明的一个目的是开发并提供一种新型农艺和园艺杀虫剂，鉴于昆虫害虫等造成的损害仍然巨大，以及在农业、园艺等领域作物生产中出现的对现有杀虫剂具有抗性的昆虫害虫。 提供了一种含有肼酰基的稠合杂环化合物或其盐，优选为通式(1)表示的稠合杂环化合物： 其中R1代表例如烷基，R2代表例如氢原子，R3和R4各自代表例如烷基、卤代烷基或酰基，A1代表例如氮原子，A2代表例如N-Me或氧原子，A3代表例如碳原子或氮原子，A4代表例如C—H，m代表例如2，n代表例如1}，或其盐；一种包含该化合物或其盐作为活性成分的农艺和园艺杀虫剂；以及使用该杀虫剂的方法。
• PYRIDONE COMPOUNDS AND AGRICULTURAL AND HORTICULTURAL FUNGICIDES CONTAINING THE SAME AS ACTIVE INGREDIENTS
  申请人：MITSUI CHEMICALS AGRO, INC.

  公开号：US20200172486A1

  公开（公告）日：2020-06-04

  Provided are a pyridone compound represented by Formula (1): wherein R1 represents a C1-C6 alkyl group which may be substituted, etc., R2 represents a halogen atom, a cyano group, etc., R3 and R4 are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group which may be substituted, etc., or in combination with the nitrogen atom to which they are bonded form a pyrrolidinyl group, a piperidinyl group, etc., which may be substituted, Y represents a phenyl group which may be substituted, etc., X represents an oxygen atom or a sulfur atom, and an agricultural and horticultural fungicide containing the same as an active ingredient.

  提供的是由化学式（1）表示的吡啶酮化合物： 其中 R1代表一个可能被取代的C1-C6烷基，等等， R2代表一个卤素原子，一个氰基，等等， R3和R4彼此独立，每个代表一个氢原子，一个可能被取代的C1-C6烷基，等等，或者与它们结合的氮原子形成一个可能被取代的吡咯啉基团，一个哌啶基团，等等， Y代表一个可能被取代的苯基，等等， X代表一个氧原子或硫原子， 以及含有该化合物作为活性成分的农业和园艺用杀菌剂。
• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE AS PEST CONTROL AGENTS<br/>[FR] COMPOSÉS TÉTRAZOLINONE ET LEUR UTILISATION EN TANT QU'AGENTS DE LUTTE CONTRE LES NUISIBLES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2018097318A1

  公开（公告）日：2018-05-31

  The present invention provides a tetrazolinone represented by formula (I) and a pest control agent comprising the same, and their use thereof. Formula (I) [wherein, W1 represents an oxygen atom or a sulfur atom; W2 represents a hydrogen atom, or a C1-C6 chain hydrocarbon group; R15 and R16 represent a halogen atom and the like; u is 0, 1, 2 or 3; the combination of E, G, X1, Y1 and Z1 represents any one of the combinations of the following a and the like: a: a combination wherein E represents #-C(X1)(Y1)-O-N=C(Z1)-, #-C(X1)(Y1)-S-N=C(Z1)-, #-C(X1)(Y1)-O-N=C(Z1)-O-CH2-, #-C(X1)(Y1)-O-N=C(Z1)-S-CH2-, #-C(X1)(Y1)-S-N=C(Z1)-O-CH2-, #-C(X1)(Y1)-S-N=C(Z1)-S-CH2-, #-C(Z1)=N-N=C(Z2)-, #-C(X1)=C(Y1)-C(Z1)=N-O-CH2- or #-C(X1)=C(Y1)-C(Z1)=N-S-CH2-; G represents a C1-C6 chain hydrocarbon group, a (C1-C6 alkoxy)C1-C6 alkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group the C1-C6 chain hydrocarbon group, the (C1-C6 alkoxy)C1-C6 alkyl group, and the (C1-C6 alkylthio)C1-C6 alkyl group may have one or more substituents selected from Group S} or R1-T1-, X1 and Y1, which are identical to or different from each other, independently represents substituents selected from Group T, and Z1 represents a substituent selected from Group V.]

  本发明提供了一种由式(I)表示的四唑酮化合物，以及包含该化合物的杀虫剂，以及它们的使用。式(I)中，W1代表氧原子或硫原子；W2代表氢原子或C1-C6链烃基；R15和R16代表卤素原子等；u为0、1、2或3；E、G、X1、Y1和Z1的组合代表以下a等组合中的任意一种：a：E代表#-C(X1)(Y1)-O-N=C(Z1)-、#-C(X1)(Y1)-S-N=C(Z1)-、#-C(X1)(Y1)-O-N=C(Z1)-O-CH2-、#-C(X1)(Y1)-O-N=C(Z1)-S-CH2-、#-C(X1)(Y1)-S-N=C(Z1)-O-CH2-、#-C(X1)(Y1)-S-N=C(Z1)-S-CH2-、#-C(Z1)=N-N=C(Z2)-、#-C(X1)=C(Y1)-C(Z1)=N-O-CH2-或#-C(X1)=C(Y1)-C(Z1)=N-S-CH2-；G代表C1-C6链烃基、(C1-C6烷氧基)C1-C6烷基、(C1-C6烷硫基)C1-C6烷基C1-C6链烃基、(C1-C6烷氧基)C1-C6烷基和(C1-C6烷硫基)C1-C6烷基中的每一种可能具有来自S族的一个或多个取代基}或R1-T1-，X1和Y1互相相同或不同，独立地代表来自T族的取代基，Z1代表来自V族的取代基。
• OXIME GROUP-CONTAINING CONDENSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
  申请人：NIHON NOHYAKU CO., LTD.

  公开号：US20210371424A1

  公开（公告）日：2021-12-02

  Provided are an oxime group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by general formula (1): (wherein the symbols are defined in the specification); an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

  提供的是含有肟基的缩合杂环化合物或其盐，优选是由通式（1）表示的缩合杂环化合物： （其中符号在规范中定义）；包括该化合物或其盐作为活性成分的农业和园艺杀虫剂；以及使用该杀虫剂的方法。
• Fungicidal oxime carbamates
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0397345A1

  公开（公告）日：1990-11-14

  A method of controlling plant diseases, especially fungi, using oxime carbamates and analogs thereof and novel compounds within the class. Reason: Rule 8.1.i PCT.

  一种使用肟基氨基甲酸酯及其类似物以及该类中的新颖化合物来控制植物病害，尤其是真菌的方法。 原因：PCT规则8.1.i。

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