monosodium methanearsonate | 2163-80-6

• 物质功能分类: 化学农药原药 - 除草剂 - 其他除草剂
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: monosodium methanearsonate
• 英文别名: methylarsonic acid monosodium salt；Mesamate；Sodium methylarsonate；sodium;hydroxy(methyl)arsinate
• CAS: 2163-80-6
• 化学式: CH₄AsO₃*Na
• 分子量: 161.952
• InChiKey: JITOKQVGRJSHHA-UHFFFAOYSA-M

物化性质

• 熔点：
  113-116°C
• 密度：
  1.50
• 物理描述：
  Methanearsonic acid, [sodium salt] appears as odorless colorless solid. Solution may be red or green. Solid may float or sink in water; solid and solution mix with water. (USCG, 1999)
• 颜色/状态：
  White solid
• 气味：
  None
• 沸点：
  Decomposes (NTP, 1992)
• 溶解度：
  16 g/100 ml in methanol @ 25 °C; 0.005 g/100 ml in hexane @ 25 °C
• 蒸汽压力：
  1X10-5 Pa @ 25 °C (7.8X10-8 mm Hg)
• 稳定性/保质期：

  STABLE TO HYDROLYSIS

• 自燃温度：
  Not flammable (USCG, 1999)
• 分解：
  When heated to decomposition it emits toxic fumes of /arsenic and sodium oxide/.
• 腐蚀性：
  NON-CORROSIVE TO IRON, RUBBER, & MOST PLASTICS
• 解离常数：
  pKa1= 4.1; pKa2 = 9.02

计算性质

• 辛醇/水分配系数(LogP)：
  -4.66
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

单钠甲酸砷在豆类中的降解...提取中回收的砷有3-5%仍然结合在不可溶残留物中。...剩余残留物...大约60%与一种ninhydrin-POS物质（RF=0.69）相关联，而40%是不络合的MSMA（RF=0.35）。...单钠甲酸砷对棉花的处理。在72小时的植物暴露期间几乎没有或没有代谢...棉花显然在处理后的至少72小时内不形成络合物。/组氨酸络合物在其他植物中已被提出，但尚未被证实/

... DEGRADATION OF MONOSODIUM METHANEARSONATE IN BEANS ... 3-5% OF ARSENIC RECOVERED IN EXTRACT REMAINED BOUND TO INSOL RESIDUE. ... OF REMAINING RESIDUE ... ABOUT 60% WAS ASSOCIATED WITH A NINHYDRIN-POS SUBSTANCE (RF= 0.69) WHILE 40% WAS UNCOMPLEXED MSMA (RF= 0.35). ... MONOSODIUM METHANEARSONATE ON COTTON. LITTLE OR NO METAB...DURING 72 HR PLANT EXPOSURE. ... COTTON APPARENTLY FORMS NO COMPLEX, @ LEAST WITHIN 72 HR AFTER TREATMENT. /HISTIDINE COMPLEX PROPOSED, BUT NOT PROVEN, IN OTHER PLANTS/

来源:Hazardous Substances Data Bank (HSDB)

代谢

松树抗药性的持续时间对于亚砷酸甲钠来说比cacodylic acid( cacodylic acid)要长得多，这可能是由于添加了将亚砷酸甲钠转化为cacodylic acid的代谢步骤。。没有甲基化证据。

RESISTANCE TO ENTRY OF PINUS PONDEROSA WAS SUBSTANTIALLY MORE PROLONGED FOR MONOSODIUM METHANEARSONATE THAN FOR CACODYLIC ACID WHICH MAY BE RESULT OF ADDED METABOLIC STEP NECESSARY TO CONVERT MONOSODIUM METHANEARSONATE TO CACODYLIC ACID. ... NO PROOF OF METHYLATION ... OFFERED.

来源:Hazardous Substances Data Bank (HSDB)

代谢

志愿者摄入了一剂500毫克的砒霜，以亚砷酸钠的形式。四天后，摄入的砒霜中有78%通过尿液排出。亚砷酸被甲基化为13%的二甲胂酸盐。/亚砷酸，二钠盐/

VOLUNTEERS INGESTED A SINGLE ORAL DOSE OF 500 MG ARSENIC AS DISODIUM METHANEARSONATE. AFTER 4 DAYS, 78% OF INGESTED ARSENIC WAS EXCRETED IN URINE. METHANEARSONATE IS 13% METHYLATED INTO DIMETHYLARSINATE. /METHANEARSONIC ACID, DISODIUM SALT/

来源:Hazardous Substances Data Bank (HSDB)

代谢

...DSMA...在...植物中的反应...单个放射性化合物...在紫花莎草（莎草科圆莎草属）的热80%乙醇提取物中发现。化学分析显示C-As键保持完整。/甲基肿酸，二钠盐/

REACTION OF ... DSMA ... EXAMINED IN ... PLANTS ... SINGLE RADIOACTIVE CMPD ... FOUND /IN PURPLE NUTSEDGE (CYPERUS ROTUNDUS LEGUMINOSAE)/ IN HOT 80% ETHANOL EXTRACT. CHEM ANALYSIS REVEALED THAT C-AS BOND REMAINED INTACT. /METHANEARSONIC ACID, DISODIUM SALT/

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 检查了DSMA的反应产物 ... 在紫色香附子（莎草科植物圆果苔草）。... 从（14）C DSMA处理的植物中检测到呼吸二氧化碳中的放射性，表明C-AS键降解。/甲基亚砷酸，二钠盐/

... EXAMINED REACTION PRODUCTS OF DSMA ... IN PURPLE NUTSEDGE (CYPERUS ROTUNDUS L). ... RADIOACTIVITY WAS ... DETECTED IN RESPIRATORY CARBON DIOXIDE FROM (14)C DSMA-TREATED PLANTS, INDICATING C-AS BOND DEGRADATION. /METHANEARSONIC ACID, DISODIUM SALT/

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

• 人类毒性摘录

包含的化合物为甲酸和其钠盐；34例中有9例出现全身症状，其余有眼睛和皮肤刺激。

COMPOUNDS INCLUDED METHANEARSONIC ACID & ITS SODIUM SALTS; 9/34 CASES SHOWED SYSTEMIC SYMPTOMS & REMAINDER HAD EYE & SKIN IRRITATION.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

有机砷化合物包括甲基胂酸钠...和氨基甲基砷酸钠。这些化合物对人类的有毒性远低于...无机砷化合物；然而，如果吸入、吞咽或接触到眼睛或皮肤，它们仍然是有害的。/甲基胂酸钠/

ORGANIC ARSENICALS INCLUDE DISODIUM METHYLARSONATE ... AND AMINE METHYLARSONATE.TOXICITY OF THESE CMPD TO HUMANS IS CONSIDERABLY LESS THAN ... INORGANIC ARSENICALS; HOWEVER THEY ARE HARMFUL IF INHALED, SWALLOWED, OR IF THEY COME IN CONTACT WITH EYES OR SKIN. /DISODIUM METHYLARSONATE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

... 通过肾小管给牛每天每千克体重10毫克的甲基砷酸钠。在5只治疗中的牛中有4只，在治疗8-10天后死亡。死亡原因是明显的肾衰竭。在肾脏和肝脏中发现了高水平的砷。... 100和1000 PPM按重量比的... 甲基砷酸钠/在60%蔗糖浆中/对新生工蜂极其有毒 ... 纯净和商业配方的除草剂之间的毒性没有观察到差异。

... GAVE MONOSODIUM METHANEARSONATE TO CATTLE THROUGH RENAL TUBULES @ DOSE OF 10 MG/KG DAILY. FOUR OF 5 ... TREATED DIED AFTER 8-10 DAYS OF TREATMENT. CAUSE OF DEATH WAS APPARENT KIDNEY FAILURE. HIGH LEVELS OF ARSENIC WERE FOUND IN KIDNEY & LIVER. ... 100 & 1000 PPM BY WT OF ... MONOSODIUM METHANEARSONATE /IN 60% SUCROSE SYRUP/ WERE EXTREMELY TOXIC TO NEWLY EMERGED WORKER BEES ... NO DIFFERENCES IN TOXICITY WERE OBSERVED BETWEEN PURIFIED & COMMERCIALLY FORMULATED HERBICIDES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

单钠砷酸甲酯和 cacodylic 酸对处理过的松树昆虫死亡率的影响进行了研究。观察到化合物之间的昆虫存活率差异。

... EXAMINED EFFECTS OF MONOSODIUM METHANEARSONATE & CACODYLIC ACID ON INSECT MORTALITY IN TREATED PONDEROSA PINES ... DIFFERENCES OF INSECT SURVIVAL BETWEEN CMPD WERE NOTED.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

MSMA比cacodylic acid（ cacodylic acid）更迅速地转移到根系，并且可能转移到芽尖，但它并没有更大的植物毒性。当黑情人节豆类用(14)C MSMA处理时，放射性MSMA存在于营养液上方、下方和营养液中。…Nutgrass块茎积累砷，较小的块茎含有最高的砷浓度。

MSMA ... TRANSLOCATED MORE RAPIDLY THAN CACODYLIC ACID TO ROOT SYSTEM & PROBABLY ... SHOOT TIP, YET IT WAS NOT MORE PHYTOTOXIC. RADIOACTIVE MSMA WAS FOUND ABOVE, BELOW & IN NUTRIENT SOLN WHEN BLACK VALENTINE BEANS WERE TREATED WITH (14)C MSMA. ... NUTSEDGE TUBERS ACCUM ARSENIC & SMALLER TUBERS CONTAINED HIGHEST CONCN.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在棉花中...（14）C MSMA从子叶中转移的速度在20°C处理时比29°C处理时更快。最大吸收...发生在29°C。

/IN COTTON/ ... (14)C MSMA TRANSLOCATED OUT OF COTYLEDONS FASTER WHEN TREATED @ 20 °C THAN @ 29 °C. MAX ABSORPTION ... OCCURRED @ 29 °C.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 10毫克/千克/天 ... 在10天内对牛类证实致命；肾脏和肝脏中的砷含量在27-64 ppm范围内。

... 10 MG/KG/DAY ... PROVED FATAL TO CATTLE IN 10 DAYS; ARSENIC CONTENT OF KIDNEY & LIVER BEING IN RANGE 27-64 PPM.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当棉株高度达到7.6厘米并在初花期前施用甲烷亚砷酸及其钠盐和二钠盐时，棉籽中未发现显著砷残留。

No significant arsenic residues are found in cottonseed when the sodium & disodium salts of methanearsonic acid are applied after the cotton has reached a height of 7.6 cm and before early bloom.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S20/21,S28,S45,S60,S61
• 危险类别码：
  R22
• 危险品运输编号：
  UN 1557
• 包装等级：
  III
• 危险类别：
  6.1(b)

制备方法与用途

化学性质

甲基砷酸钠是一种褐色且具有粘稠性的液体，散发出类似于水果的香气。该产品易溶于水，在常温条件下稳定。它与强氧化剂和强还原剂反应容易被分解，并不可燃。

用途

甲基砷酸钠可用作农药除草剂。

类别

农药

毒性分级

中毒

急性毒性

• 口服 - 大鼠 LD50：700毫克/公斤

刺激数据

• 皮肤 - 兔子 54毫克 轻度
• 眼睛 - 兔子 34毫克 轻度

可燃性危险特性

受热分解产生有毒砷化物气体。

储运特性

需存放在通风、低温和干燥的仓库中，并与食品原料分开储运。

灭火剂

砂土、干粉、泡沫。

职业标准

TWA 0.5毫克（砷）/立方米

反应信息

• 作为反应物：
  描述：

  monosodium methanearsonate 在 盐酸 、 二氧化硫 、 potassium iodide 作用下， 以 水 为溶剂， 反应 0.5h， 以97%的产率得到甲基-亚胂二碘化物
  参考文献：
  名称：

  有机砷抗生素胂草素的化学合成

  摘要：

  我们报告了新型有机砷抗生素胂菌素 (AST) 的两种化学合成途径。一种是通过 2-氯乙基(甲基)胂酸与乙酰氨基丙二酸缩合，第二种涉及还原N-乙酰基保护的羟基胂丝菌素 (AST-OH) 衍生物，然后用甲基碘将三价砷中间体甲基化。使用酶 AST N-乙酰转移酶 (ArsN1)从外消旋 AST中纯化L -AST。这种化学合成为未来的药物开发提供了这种新型抗生素的来源。

  DOI：

  10.1039/d1ra06770b

文献信息

• 6-arylpyrimidines and herbicidal use
  申请人：Rohm and Haas Company

  公开号：US05397767A1

  公开（公告）日：1995-03-14

  A class of 6-arylpyrimidines which is useful in the control of weeds is of the general formulae: ##STR1## wherein R.sup.2 is selected from hydrogen, halo, substituted or unsubstituted alkyl, haloalkyl, polyhaloalkyl, haloalkenyl, polyhaloalkenyl, haloalkynyl, polyhaloalkynyl, alkenyl, alkynyl, alkoxy, alkylthio, alkoxycarbonylalkyl, cyano, alkoxyalkyl, alkoxycarbonyl, cycloalkyl, aralkyl, alkylamino, dialkylamino, or dialkylaminocarbonyl group; R.sup.3 is an alkyl, alkenyl, alkynyl, or haloalkyl group; R.sup.5 is an alkyl, alkenyl, alkynyl, alkenynyl, or alkoxyalkyl, group; R.sup.6 is an aryl group (e.g. aromatic ring); and X is oxygen or sulfur. R.sup.2 and R.sup.3 may form a fused ring.

  一类6-芳基嘧啶类化合物可用于除草，其一般式为：##STR1##其中R.sup.2选自氢、卤素、取代或未取代的烷基、卤代烷基、多卤代烷基、卤代烯基、多卤代烯基、卤代炔基、多卤代炔基、烯基、炔基、烷氧基、烷硫基、烷氧羰基烷基、氰基、烷氧基烷基、烷氧羰基、环烷基、芳基烷基、烷基氨基、二烷基氨基或二烷基氨基羰基；R.sup.3为烷基、烯基、炔基或卤代烷基；R.sup.5为烷基、烯基、炔基、烯炔基或烷氧基烷基；R.sup.6为芳基（例如芳香环）；X为氧或硫。R.sup.2和R.sup.3可以形成融合环。
• Halopyridyl triazolinone herbicides and herbicidal use thereof
  申请人：Rohm and Haas Company

  公开号：US05733849A1

  公开（公告）日：1998-03-31

  Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

  本发明涉及除草的卤代吡啶基三唑啉酮，包含该卤代吡啶基三唑啉酮的除草组合物，以及该化合物和组合物的除草用途。这种化合物和组合物在各种农作物中作为早期和后期除草剂都很有用。
• Chemical synthesis of the organoarsenical antibiotic arsinothricin
  申请人：Rosen Barry P.

  公开号：US11518775B1

  公开（公告）日：2022-12-06

  The subject invention provides methods for the chemical synthesis of racemic arsinothricin (D,L-AST), the novel organoarsenical antibiotic. One is by condensation of the 2-chloroethyl(methyl)arsinic acid with acetamidomalonate, and the second involves reduction of the N-acetyl-protected derivative of hydroxyarsinothricin (AST-OH) and subsequent methylation of the resulting sodium salt of trivalent arsenic intermediate with methyl iodide. The enzyme AST N-acetyltransferase (ArsNl) was utilized to purify L-AST from racemic AST. This expedient chemical synthesis of AST provides a source of this novel antibiotic for future drug development.