亚砜磷 | 301-12-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 中文名称: 亚砜磷
• 中文别名: 亚砜吸磷；砜吸磷；内吸磷-S-甲基-亚砜；异砜吸硫磷
• 英文名称: Aimco systox
• 英文别名: oxydemeton-methyl；1-dimethoxyphosphorylsulfanyl-2-ethylsulfinylethane
• CAS: 301-12-2
• 化学式: C₆H₁₅O₄PS₂
• 分子量: 246.288
• InChiKey: PMCVMORKVPSKHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  6

ADMET

代谢

在大鼠代谢研究中，给大鼠单次静脉注射或口服1毫克/公斤的14C-1-乙烯基标记的ODM（14C-ODM），单次口服20毫克/公斤，或者连续14天口服未标记的ODM，每天1毫克/公斤，然后单次口服1毫克/公斤的14C-ODM。...确定了每个处理组的主要尿液和粪便代谢物。尿液放射性分析显示，大部分给予的14C-ODM没有被代谢。未代谢的ODM在1毫克/公斤，静脉注射组的雄性和雌性大鼠中分别为43%和47%；1毫克/公斤，口服组的雄性和雌性大鼠中分别为38%和47%；重复口服1毫克/公斤/天的雄性和雌性大鼠中分别为34%和55%；20毫克/公斤，口服组的雄性和雌性大鼠中分别为59%和74%。还鉴定出两种主要代谢物和三种次要代谢物。一种主要代谢物被鉴定为2-（乙硫基亚基）-1-（甲硫基亚基）乙烷，在1毫克/公斤，静脉注射时占给药剂量的18-21%；口服时占24-25%；口服15×1毫克/公斤/天时占15%；口服20毫克/公斤时占5-6%。第二种主要代谢物被鉴定为2-（乙硫酰基）-1-（甲硫基亚基）乙烷；这种代谢物在1毫克/公斤，静脉注射时占给药剂量的11-19%；口服时占16-20%；口服15×1毫克/公斤/天时占12-23%；口服20毫克/公斤时占6-19%。一种次要代谢物（以给药剂量的百分比表示，适用于雄性和雌性大鼠）被鉴定为ODM磺酰，在1毫克/公斤，静脉注射时占总给药剂量的1.7-3.4%；口服时占1.6%；口服15×1毫克/公斤/天时占2.4-2.6%；口服20毫克/公斤时占2.6-3.9%。另外两种次要代谢物被鉴定为去甲基ODM和去甲基ODM磺酰，仅在20毫克/公斤，口服组中检测到，分别占2.6-3.1%和1.0-3.1%。主要的粪便代谢物包括未代谢的ODM（0.2%）、ODM硫化物（0.8%）和ODM磺酰（0.2%）。代谢轮廓的差异表明，在高剂量下生物转化可能达到饱和。结果表明，在20毫克/公斤时，未代谢的母体化合物在尿液中的排泄量显著增加（59-74%），同时与1毫克/公斤的雄性和雌性大鼠相比，代谢物在尿液中的排泄量显著下降（未代谢的母体排泄：34-55%）。

In a metabolism study..., rats were dosed with 14C-1-ethylene-labeled ODM ( 14C-ODM) at a single at dose 1 mg/kg, either iv or orally (po), a single oral dose at 20 mg/kg, or with 14 daily oral doses of unlabeled ODM at 1 mg/kg/day followed by a single oral dose of 14C-ODM at 1 mg/kg. ...The identification of major urinary and fecal metabolites were determined for each treatment group. Analysis of the urinary radioactivity revealed that most of administered 14C-ODM was not metabolized. The respective % for males and females of unmetabolized ODM were 43% and 47% for the 1 mg/kg, iv group; 38% and 47% for the 1 mg/kg, po group; 34% and 55% for the repeat, 1 mg/kg/day, po group; and 59% and 74% for the 20 mg/kg, po group. Two major metabolites and three minor ones were also identified. One major metabolite was identified as 2- (ethylsulfinyl)-1-(methylsulfinyl) ethane, and accounted for 18-21% of the administered dose at 1 mg/kg, iv; 24-25%, at 1 mg/kg, po; 15%, at 15 x 1 mg/kg/day, po; and 5-6%, at 20 mg/kg, po. The second major metabolite was identified as 2-(ethylsulfonyl)-1-(methylsulfinyl) ethane; this metabolite accounted for 11-19% of the administered dose at 1 mg/kg, iv; 16-20%, at 1 mg/kg, po; 12-23%, at 15 x 1 mg/kg/day, po; and 6-19%, at 20 mg/kg, po. One minor metabolite (as a % of the administered dose for both males and females) was identified as ODM sulfone and was present at 1.7-3.4% of the total administered dose at 1 mg/kg, iv; 1.6%, at 1 mg/kg, po; 2.4-2.6%, at 15 x 1 mg/kg/day, po; and 2.6-3.9%, at 20 mg/kg, po. Two other minor metabolites were identified as desmethyl ODM and desmethyl ODM sulfone and were detected only in the 20 mg/kg, po, group at 2.6-3.1% and 1.0-3.1%, respectively. Primary fecal metabolites included unmetabolized ODM (0.2%), ODM sulfide (0.8%) and ODM sulfone (0.2%). The differences in the metabolic profiles suggests that the biotransformation may be saturated at high doses. The results indicate that at 20 mg/kg a marked increase in urinary excretion of unmetabolized parent compound (59-74%) in conjunction with a marked decline in the urinary excretion of metabolites compared to the corresponding values for males and female rats receiving 1 mg/kg (excretion of unmetabolized parent: 34-55%).

来源:Hazardous Substances Data Bank (HSDB)

代谢

代森锌 S-甲基亚砜通过假单胞菌属1453菌株断裂硫酯键，形成2-(乙基亚磺酰基)乙硫醇、2-(乙基亚磺酰基)乙硫醇和双(2-(乙基亚磺酰基)乙基)二硫醚。诺卡氏菌属DSM 43252将其转化为双(2-(乙基亚磺酰基)乙基)二硫醚、双(2-(乙基亚磺酰基)乙基)硫醚和双(2-(乙基亚磺酰基)乙基)硫醚。检出了o,o-二甲基硫代磷酰酸。

Demeton S-methyl sulfoxide is degraded by Pseudomonas putida 1453 by cleavage of thioester bond to form 2-(ethylsulfinyl)ethanethiol, 2-(ethylsulfonyl)ethanethiol and bis(2-(ethylsulfinyl)ethyl)disulfide. Nocardia sp dsm 43252 converts it into bis(2-(ethylsulfonyl)ethyl)disulfide, bis(2-(ethylsulfinyl)ethyl)sulfide, and bis(2-(ethylsulfonyl)ethyl)sulfide. o,o-Dimethylthiophosphoric acid was detected.

来源:Hazardous Substances Data Bank (HSDB)

代谢

代谢主要通过氧化、酯酶的水解以及分子部分转移到谷胱甘肽来进行。有机磷杀虫剂的氧化可能导致毒性更高或更低的产品。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及其氧酸。/有机磷农药/

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)

毒理性

• 致癌性证据

癌症分类：不太可能对人类致癌

Cancer Classification: Not Likely to be Carcinogenic to Humans

来源:Hazardous Substances Data Bank (HSDB)

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

毒理性

• 毒性数据

大鼠LC50 = 427毫克/立方米/小时

LC50 (rat) = 427 mg/m3/1h

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

毒理性

• 相互作用

维生素E（α-生育酚）对大脑和脊髓不同区域脂质过氧化速率和脂肪酶活性的影响进行了研究。通过连续10天以1.0和2.0毫克/千克体重的两种不同剂量腹腔注射甲氧基毒物，结果显示，大鼠大脑半球、小脑、脑干和脊髓中的总脂质、胆固醇和酯化脂肪酸含量呈剂量依赖性减少。脂质过氧化速率和脂肪酶活性在不同中枢神经系统区域呈剂量依赖性增加。单独给予α-生育酚可显著降低脂质过氧化和脂肪酶活性。当与甲氧基毒物同时给药时，α-生育酚可预防甲氧基毒物引起的脂质过氧化和脂肪酶活性的增加。

The effects of vitamin E (alpha-tocopherol) on the rate of lipid peroxidation and lipase activity ln the discrete areas of the brain and spinal cord were studied. Administration of metasystox in two different doses 1.0 and 2.0 mg/kg body weight ip daily for 10 days have shown a dose-related depletion of total lipids cholesterol and esterified fatty acids in the rat cerebral hemisphere, cerebellum brain stem and spinal cord. The rate of lipid peroxidation and lipase activity showed dose-dependent increase in different regions of the CNS. Administration of alpha-tocopherol alone caused significant reduction of lipid peroxidation and lipase activity. When it was admistered simultaneously with metasystox, alpha-tocopherol prevented the metasystox induced increase of lipid peroxidation and lipase activity.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

气道保护。确保呼吸道畅通。必要时对患者进行气管插管，并使用大口径吸痰设备吸出分泌物。如果呼吸抑制，通过机械辅助肺通气给予氧气。在给予阿托品之前尽可能改善组织氧合，以最小化心室颤动的风险。在严重中毒的情况下，可能需要机械支持肺通气数天。/有机磷农药/

Airway protection. Ensure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在给予5.0毫克/公斤的14C-ODM口服剂量后，从给药后2小时到10天对组织放射性进行了评估。...给药后2小时的组织放射性测量显示，放射性最高的浓度在肾脏（4.8 ppm）；这是可以理解的，因为尿液是主要的消除途径。在分析的其它组织中，浓度从肾脂肪的2.2 ppm到肺的3.9 ppm不等。剩余的组织（肌肉、皮肤、肝脏、肾上腺和睾丸）浓度在3.0到3.6 ppm之间。一天后，组织放射性水平比2小时值低了45-106倍。到10天时，残留的组织放射性存在，从睾丸的最低值0.00035 ppm到红细胞的0.085 ppm不等。

Following an oral dose of 5.0 mg/kg /14C-ODM/, tissue radioactivity was evaluated from 2 hr to 10 days post-dosing. ...Measurement of tissue radioactivity at 2 hours post-dosing shows that the highest concentration of radioactivity was found in the kidney (4.8 ppm); this is understandable since the urine is the predominant route of elimination. The lowest tissue level was found in the brain (1.7 ppm). Of the other tissues analyzed, concentrations ranged from 2.2 ppm in renal fat to 3.9 ppm in the lung. The remaining tissues (muscle, skin, liver, adrenal gland and testes) concentrations were between 3.0 and 3.6 ppm. After one day the levels of tissue radioactivity were 45-106 times lower that the 2 hr values. By 10 days, residual tissue radioactivity was present and ranged from a low value of 0.00035 ppm in testes to 0.085 ppm in erythrocytes.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在代谢研究中，大鼠单次静脉注射或口服给予1 mg/kg的14C-1-乙烯基标记的ODM（14C-ODM），或者单次口服20 mg/kg，或者连续14天口服未标记的ODM，剂量为1 mg/kg/天，随后单次口服1 mg/kg的14C-ODM。研究结果显示，14C-ODM被迅速吸收，广泛代谢，并且快速排泄。在3天时间内，大部分（90-108%）的给药剂量被排泄。放射性物质几乎全部在尿液中回收（占给药剂量的89-105%），而粪便和呼出的CO2分别占给药剂量的0.2-2.9%和0.1%。没有任何组织或器官中生物积累的迹象。...结果表明，在20 mg/kg的剂量下，未代谢的母体化合物的尿排泄量显著增加（59-74%），与此同时，与接受1 mg/kg的雄性和雌性大鼠相比，代谢物的尿排泄量显著下降（未代谢的母体排泄量：34-55%）。

In a metabolism study..., rats were dosed with 14C-1-ethylene-labeled ODM ( 14C-ODM) at a single dose 1 mg/kg, either iv or orally (po), a single oral dose at 20 mg/kg, or with 14 daily oral doses of unlabeled ODM at 1 mg/kg/day followed by a single oral dose of 14C-ODM at 1 mg/kg. The results of this study show that 14C-ODM was rapidly absorbed, extensively metabolized, and rapidly excreted. Over a 3-day period, most (90-108%) of the administered dose was excreted. The radioactivity was recovered almost entirely in the urine (89-105% of the administered dose), while feces and expired CO2 accounted for 0.2-2.9% and 0.1% of the administered dose, respectively. There was no indication of bioaccumulation in any tissue or organ. ...The results indicate that at 20 mg/kg a marked increase in urinary excretion of unmetabolized parent compound (59-74%) in conjunction with a marked decline in the urinary excretion of metabolites compared to the corresponding values for males and female rats receiving 1 mg/kg (excretion of unmetabolized parent: 34-55%).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

全身放射自显影在大鼠上进行，这些大鼠通过静脉注射14C-ODM，剂量为1.0 mg/kg，或者口服剂量为10 mg/kg。静脉注射后，放射性物质在给药后5分钟迅速分布到全身。放射性物质在肾脏、膀胱和附睾中的浓度最高。在大脑、脊髓和睾丸中发现了较低的浓度。脂肪组织和骨骼结构中的浓度处于检测极限。口服给药后8小时拍摄的放射自显影片与静脉给药的基本相同。

Whole body autoradiography was performed on rats dosed /with 14C-ODM/ iv at 1.0 mg/kg or orally at 10 mg/kg. Following the iv dosing the radioactivity was rapidly distributed throughout the body at 5 min post-dosing. The highest concentrations of radioactivity were found in the kidney, bladder, and accessory genital gland. Lower concentrations were found in the brain, spinal cord, and testes. The concentration in fatty tissues and boney structures were at the limit of detection. Autoradiographs taken 8 hours after the oral dose were found to be essentially the same as with iv administration.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在一项经皮吸收研究中，将单一剂量的放射性标记的ODM（14C-ODM，2 mg/kg）通过皮肤给药或静脉注射给每组每性别3只Sprague-Dawley大鼠。在2、4、8、12、24、48和72小时后或直到尿液中放射性降至背景值2倍时，处死动物。对于经皮处理的动物，移除并清洗12平方厘米的给药部位，并进行计数。在每个时间点，对尿液、血浆、皮肤和皮肤溶剂洗涤样品中的放射性进行计数。...静脉给药的总回收率为雄性67%，雌性81%。对于经皮暴露途径，总回收率为雄性33%，雌性41%。ODM的回收率较低，可能是由于代谢和未包括残留全身计数。计算得出的经皮吸收率为雄性50.4%，雌性51.8%。根据随时间变化的14C-ODM毫克当量进行的回归分析计算得出的经皮吸收速率为雄性0.15 g/平方厘米/小时，雌性0.17 g/平方厘米/小时。

In a dermal absorption study..., radiolabeled ODM (14C-ODM), at a single dose level of 2 mg/kg, was administered dermally or by iv injection to 3 Sprague-Dawley rats/sex/group/time period. Animals were sacrificed 2, 4, 8, 12, 24, 48 and 72 hours or until the radioactivity in urine dropped to 2 times background. For the dermally treated animals, a 12 sq cm area of the application site was removed, washed and counted. For each time period, radioactivity was counted in urine, plasma, the skin, skin solvent wash samples. ...Total recoveries for iv route of administration were 67% for males and 81% for females. For the dermal route of exposure total recoveries were 33% for males and 41% for females. Recoveries of ODM were low, probably due to metabolism and failing to include residual total body counts. Dermal absorption was calculated to be 50.4% for males and 51.8% for females. The dermal absorption rates, as calculated by regression analysis based on mg equivalents of 14C-ODM over time, were 0.15 g/sq cm/hr for males and 0.17 g/sq cm/hr for females.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  储存温度范围为0至6°C。

反应信息

• 作为反应物：
  描述：

  亚砜磷 在 perfluoro cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 以87%的产率得到砜吸磷
  参考文献：
  名称：

  全氟顺式-2,3-二烷基恶唑烷酮在氨基磷酸酯，硫代磷酸酯和硫代磷酸酯农用化学品中的选择性硫氧化

  摘要：

  几个有机磷农药2A -g与硫醚，磷酰胺，硫代磷酰，和phosphorothionic功能用全氟反应顺式-2- Ñ丁基-3- Ñ -propyloxaziridine 1。硫化物的选择性氧化产生了亚砜衍生物3a- g，产率很高，而不会过度氧化成砜产物。亚砜3a-e在温和条件下进一步氧化为相应的砜4a-e。所有产品本身都是分析环境标准所感兴趣的，并且详细描述了其制备方法。

  DOI：

  10.1016/0040-4020(95)00413-3
• 作为产物：
  描述：

  甲基内吸磷 在 perfluoro cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 various solvent(s) 为溶剂， 反应 0.17h， 生成 亚砜磷
  参考文献：
  名称：

  全氟顺式-2,3-二烷基恶唑烷酮在氨基磷酸酯，硫代磷酸酯和硫代磷酸酯农用化学品中的选择性硫氧化

  摘要：

  几个有机磷农药2A -g与硫醚，磷酰胺，硫代磷酰，和phosphorothionic功能用全氟反应顺式-2- Ñ丁基-3- Ñ -propyloxaziridine 1。硫化物的选择性氧化产生了亚砜衍生物3a- g，产率很高，而不会过度氧化成砜产物。亚砜3a-e在温和条件下进一步氧化为相应的砜4a-e。所有产品本身都是分析环境标准所感兴趣的，并且详细描述了其制备方法。

  DOI：

  10.1016/0040-4020(95)00413-3

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。