稻丰散 | 2597-03-7

• 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: 稻丰散
• 中文别名: 稻芬妥胺酚拉明；O,O-二甲基-S-(乙氧基羰基苄基)二硫代磷酸酯；益尔散；2-[(二甲氧基硫代膦酰)硫基]苯乙酸乙酯；爱乐散；O,O-二甲基-S-(苯基乙酸乙酯)二硫代磷酸酯；O,O-二甲基-S-(α-乙氧基羰基苄基)二硫代磷酸酯
• 英文名称: Phenthoate
• 英文别名: ethyl 2-dimethoxyphosphinothioylsulfanyl-2-phenylacetate
• CAS: 2597-03-7
• 化学式: C₁₂H₁₇O₄PS₂
• 分子量: 320.37
• InChiKey: XAMUDJHXFNRLCY-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  如果按照规格进行使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

ADMET

代谢

ELSAN迅速降解成/CABBAGE SEEDLING, STRAWBERRY & APPLE FRUIT/ ... 并被水解成无毒衍生物。主要代谢物...是ELSAN羧基衍生物，扁桃酸和双(羧乙基苄基)二硫化物。

ELSAN DEGRADED RAPIDLY IN /CABBAGE SEEDLING, STRAWBERRY & APPLE FRUIT/ ... & WAS HYDROLYZED TO NON-TOXIC DERIVATIVES. MAIN METABOLITES ... WERE ELSAN CARBOXY DERIVATIVES, MANDELIC ACID & BIS(CARBETHOXYBENZYL)DISULFIDE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

辛硫磷在小鼠体内的主要尿液代谢物，在30毫克/千克的剂量下，为O-脱甲基酸（25.8%）、O-脱甲基氧酸（18.4%）和二甲基硫代磷酰氧（16.9%）。P-S裂解的初始产物...进一步代谢成相应的硫代物、扁桃酸和S-甲基化衍生物。

MAJOR URINARY METABOLITES /OF PHENTHOATE IN MICE/ @ DOSAGE OF 30 MG/KG WERE THE O-DEMETHYLATED ACID (25.8%), THE O-DEMETHYLATED OXON ACID (18.4%) & DIMETHYL PHOSPHORODITHIONATE (16.9%). INITIAL PRODUCT OF P-S CLEAVAGE ... WAS FURTHER METABOLIZED INTO CORRESPONDING SULFIDE, MANDELIC ACID, & S-METHYLATED DERIV.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在植物中，硫代磷酸会发生氧化，然后是水解。已识别的代谢物包括磷酸、二甲磷酸和单甲磷酸。

In plants, there is oxidation to the thiophosphate, followed by hydrolysis. Identified metabolites are phosphoric acid, dimethyl and monomethyl phosphate.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在患者摄入有机磷杀虫剂苯硫磷后，从血浆和尿液中检测到了五种代谢物。完整的苯硫磷仅在胃灌洗液中检测到。通过酸化血浆和尿液的甲基化提取，使用气相色谱和气相色谱-质谱联用技术，鉴定出了苯硫磷酸、去甲基苯硫磷、去甲基苯硫磷氧酸、去甲基苯硫磷S-异构体和去甲基苯硫磷酸S-异构体，与合成的苯硫磷类似物进行了比对。主要代谢物是苯硫磷酸和去甲基苯硫磷氧酸。尽管去甲基苯硫磷氧酸是一个重要的代谢物，但没有检测到苯硫磷氧、苯硫磷氧酸或去甲基苯硫磷氧。如果患者体内形成了氧，它可能被羧酸酯酶或谷胱甘肽转移酶迅速降解为去甲基苯硫磷氧酸。

Five metabolites were detected in the plasma and urine of a patient following ingestion of the organophosphate insecticide, phenthoate. Intact phenthoate was detected only in gastric lavage fluid. After methylation of acidic extracts of plasma and urine, phenthoate acid, demethyl phenthoate, demethyl phenthoate oxon acid, demethyl phenthoate S-isomer, and demethyl phenthoate acid S-isomer were identified with synthesized phenthoate analogues by gas chromatography and gas chromatograph-mass spectrometry. The main metabolites were phenthoate acid and demethyl phenthoate oxon acid. Although demethyl phenthoate oxon acid was a significant metabolite, no phenthoate oxon, phenthoate oxon acid or demethyl phenthoate oxon were detected. If the oxon was formed in the patient, it may have been rapidly degraded by carboxylesterase or glutathione transferase to demethyl phenthoate oxon acid.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒药 - 有机磷

Other Poison - Organophosphate

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

毒理性

• 毒性数据

LC50 (大鼠) = 59毫克/立方米/4小时

LC50 (rat) = 59 mg/m3/4h

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

毒理性

• 相互作用

...迅速被大鼠肝脏和血浆羧酸酯酶水解成相应的无毒代谢物，苯甲酸。从大鼠肝脏微粒体中分离出的部分纯化酶在水解苯甲酸方面比微粒体部分有效7倍。在苯甲酸技术配方中存在的两种杂质O,O',S-三甲基磷硫代硫酸盐(TMPT)和O,O,S-三甲基磷硫代硫酸盐(TMPDT)，对其抑制羧酸酯酶降解(苯基-14)C-苯甲酸的体外试验进行了检测。在大鼠肝脏和血浆羧酸酯酶的存在下，将(14)C-苯甲酸与这些杂质一起培养，可以大大减少苯甲酸的形成。与TMPT相比，TMPDT在大鼠肝脏羧酸酯酶的抑制活性方面更为优越。与大鼠肝脏羧酸酯酶相比，TMPDT在抑制粗大鼠肝脏和血浆羧酸酯酶方面具有相同的效力。

Phenthoate ... was rapidly hydrolyzed by rat liver and plasma carboxylesterases to the corresponding non-toxic metabolite, phenthoate acid. A partially purified enzyme isolated from rat liver microsomes was 7-fold more effective in hydrolyzed phenthoate than the microsomal fraction. O,S,S-Trimethyl phosphorodithioate (TMPDT) and O,O,S-trimethyl phosphorothioate (TMPT), 2 impurities present in technical formulations of phenthoate, were examined for their inhibiting effects on the esterase degradation of (phenyl-14)C-phenthoate in vitro. Incubation of (14)C-phenthoate with rat liver and plasma carboxylesterases in the presence of these impurities greatly diminished the amount of phenthoate acid formed. TMPDT was superior in its inhibitory action against rat liver carboxylesterase to that of TMPT. TMPDT was equipotent in inhibiting crude rat liver and plasma carboxylesterases than rat liver carboxylesterases.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

在体外，研究了在大鼠口服给予100 mg/kg的非毒性剂量辛硫磷（O,O-二甲基 S-（α-（羧乙氧基）苄基）亚磷酸酯）后的代谢情况。同样，在联合给予0.5%的O,S,S-三甲基亚磷酸酯（OSS-Me）后进行了相同的代谢研究。当单独给予辛硫磷时，它主要通过羧乙氧基酯的水解和P-O以及C-S键的断裂进行代谢，产生了至少6种代谢物。主要的尿代谢物是辛硫磷酸。联合给予0.5% OSS-Me并未改变排泄的代谢物类型。然而，观察到羧酸酯酶催化的产物（辛硫磷酸）的减少，表明负责辛硫磷主要解毒途径的酶被抑制了。

The in vitro metabolism of phenthoate (O,O-dimethyl S-(alpha-(carboethoxy)benzyl)phosphorodithioate) was followed in rats after oral administration of a nontoxic dose of 100 mg/kg. The same metabolic study was conducted following coadministration of 0.5% O,S,S-trimethyl phosphorodithioate (OSS-Me). When administered alone, phenthoate was metabolized principally by carboethoxy ester hydrolysis and cleavage of the P-O and C-S bonds, resulting in at least 6 metabolites. The primary urinary metabolite excreted was phenthoate acid. Coadministration of 0.5% OSS-Me did not alter the types of metabolites excreted. However, a reduction of the carboxylesterase-catalyzed product (phenthoate acid) was observed, indicating that the enzyme responsible for the major pathway of phenthoate detoxication was inhibited.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

总脂质、游离脂肪酸、胆固醇和脂肪酶活性在个体和联合接触卡巴立尔和辛硫磷的条件下，对斑点刺鲀（Channa punctatus Bloch）的选定组织进行了研究。在所有接触期间，总脂质水平随着游离脂肪酸和脂肪酶活性的升高而降低，这表明为了应对杀虫剂的毒性压力，增加了脂质水解以获取能量。胆固醇水平显示出上升趋势。卡巴立尔+辛硫磷处理产生的影响比单独使用任何一种杀虫剂都要大，这表明存在加性效应。

The levels of total lipids, free fatty acids, cholesterol, and lipase activity were studied in selected tissues of Channa punctatus Bloch during individual and combined exposures of carbaryl and phenthoate. The total lipid levels decreased with elevated levels of free fatty acids and lipase activity during all exposures, suggesting increased lipid hydrolysis to derive energy as an attempt to face the pesticide toxic stress. The cholesterol levels showed an elevated trend. ... The effect produced by carbaryl + phenthoate treatment remained higher than either of the pesticides alone, suggesting the manifestation of an additive effect.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大多数有机磷化合物可以通过皮肤、结膜、胃肠系统和肺部被吸收。/有机磷化合物/

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷农药的皮肤吸收率可能会受到所使用溶剂的影响。

The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

许多有机磷杀虫剂会通过牛奶排出体外... /有机磷杀虫剂/

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷化合物被吸收后，大部分以水解产物的形式几乎完全通过尿液排出。/抗胆碱酯酶剂/

Following their absorption, most organophosphorus cmpd are excreted almost entirely as hydrolysis products in the urine. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

合成制备方法

在30℃下，将95%以上的二氯化磷70摩尔缓慢滴入含有192摩尔苯乙酸和40升二氯乙烷的混合液中。滴加完毕后，回流反应30分钟，继续搅拌1小时。随后，在回流状态下于1到1.5小时内滴加250摩尔无水乙醇，滴加完成后继续搅拌反应1小时完成酯化过程。反应液经过碱洗、萃取、中和、水洗及脱溶剂处理后得到棕红色液体。产物即为a-溴代苯乙酸乙酯，总产量为45千克，含量超过91%，收率为87.7%。

反应信息

• 作为反应物：
  描述：

  稻丰散 生成 O,O-dimethyl S-(α-(carboethoxy)benzyl)phosphorodithioate 、 (-)-phenthoate
  参考文献：
  名称：

  Enantioselective Degradation and Chiral Stability of Phenthoate in Soil

  摘要：

  DOI：

  10.1007/s00128-007-9099-5
• 作为产物：
  描述：

  对羟基二苯胺 在 三氯化铁 苯胺 作用下， 生成 稻丰散
  参考文献：
  名称：

  Para-aminophenol derivatives

  摘要：

  一种从粗对氨基苯酚溶液中制备二芳基对苯二胺的工艺，例如通过在水酸性反应介质中催化加氢硝基苯获得的溶液。该工艺包括将含有对氨基苯酚的酸性溶液与苯胺、混合甲基苯胺、邻甲苯胺、混合二甲苯胺和它们的混合物等芳香胺中选择的一种接触，在芳香胺从粗料溶液中提取对氨基苯酚并与其分离的条件下。然后，含有芳香胺萃取剂、对氨基苯酚和少量杂质的分离溶液与烷基化催化剂接触，以产生二芳基对苯二胺。

  公开号：

  US04256669A1

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。

表征谱图