[(2-dimethylamino-1-methylsulfanyl-2-oxoethylidene)amino] N-methylcarbamate | 97502-85-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2-dimethylamino-1-methylsulfanyl-2-oxoethylidene)amino] N-methylcarbamate
• 英文别名: methyl (1E)-2-(dimethylamino)-N-(methylcarbamoyloxy)-2-oxoethanimidothioate
• CAS: 97502-85-7；23135-22-0；32817-80-4
• 化学式: C₇H₁₃N₃O₃S
• 分子量: 219.26
• InChiKey: KZAUOCCYDRDERY-WEVVVXLNSA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Predicted)
• 物理描述：
  Oxamyl is a white, crystalline solid, with slight sulfurous odor. Used as an insecticide, nematicide and acaricide on many field crops, vegetables, fruits, and ornamentals. (EPA, 1998)
• 颜色/状态：
  White crystalline solid
• 气味：
  Slight sulfurous odor
• 沸点：
  Decomposes on distillation
• 熔点：
  100-102 °C, changes to a different crystalline form, mp 108-110 °C
• 溶解度：
  Solubility (g/100 ml @ 25 °C): acetone, 67; ethanol, 33; 2-propanol, 11; methanol, 144; toluene, 1
• 蒸汽压力：
  0.00023 mm Hg @ 20-25 °C
• 稳定性/保质期：

  Solid and formulations are stable... .

• 分解：
  Decomposes to innocuous materials in natural waters and soil.
• 腐蚀性：
  Non-corrosive

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

草铵膦的代谢在人类中尚未得到充分研究。预计会再次产生肟，随后像甲硫磷那样形成酮。二甲乙酰基团可能水解形成N,N-二甲基甲酰胺，以N-甲基甲酰胺和甲酰胺的形式通过尿液排出...或者是N,N-二甲基碳酰胺酸。

The metabolism of oxamyl ... has not been much studied in humans. Oxime production would be expected to occur again ... with subsequent ketone formation as for methomyl. The dimethylacetyl group may hydrolyze to form N,N-dimethylformamide, excreted as N-methylformamide and formamide in urine ... or N,N-dimethyl carbamic acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

三种肟基碳酰胺，即aldoxime、甲硫菌灵和氧苯甲腈，都将通过R1裂解产生N-甲基甲酰胺和N-甲基氨基甲酸。前者是N,N-二甲基甲酰胺的尿液生物监测标志物。

All three of the oxime carbamates, aldicarb, methomyl, and oxamyl, will produce the N-methylformamide ... and N-methylamino formic acid ... as a result of R1 cleavage. The former is a urinary biological monitoring marker for N,N-dimethylformamide ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

(14)C-草酰胺在大鼠体内通过两个主要途径降解，这些大鼠每次接受1毫克的(14)C-草酰胺（相当于每公斤体重2.5至4.6毫克），在连续18天或更长时间接受50至150 ppm（大约每公斤体重2.5至7.4毫克/天）的非放射性草酰胺饮食后。草酰胺被水解为一种氧亚氨基代谢物（甲基N-羟基-N',N'-二甲基-1-硫代草酰胺）或通过N,N-二甲基-1-氰甲酰胺（DMCF）酶促转化为N,N-二甲基草酸。氧亚氨基化合物的共轭物、酸及其单甲基衍生物构成了尿液和粪便中排出的代谢物的70%以上。少于0.3%的草酰胺以二氧化碳形式呼出，但(14)C-CO2的摄入占据了组织中剩余放射性活性的50%以上……。

(14)C-oxamyl was degraded by two major pathways in rats that received 1 mg each (2.5 to 4.6 mg/kg) after having received nonradioactive oxamyl for 18 days or more at a dietary level of 50 to 150 ppm (about 2.5 to 7.4 mg/kg/day). Oxamyl was hydrolyzed to an oximino metabolite (methyl N-hydroxy-N',N'-dimethyl-1-thioxamimidate) or converted enzymatically via N,N-dimethyl-1-cyanoformide (DMCF) to N,N-dimethyloxamic acid. Conjugates of the oximino cmpd, the acid, and their monomethyl derivatives constituted over 70% of the metabolites excreted in the urine and feces. Less than 0.3% of the oxamyl was exhaled as carbon dioxide, but incorporation of (14)C-CO2 accounted for more than 50% of the radioactivity remaining in the tissues ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

尿液中的主要成分是内酯糖苷酸（占剂量的31-37%）、代谢物内酯（占剂量的13-18%）和母体内酯（占剂量的7-11%）。

The major component present in the urine was glucuronide of oxime (31 - 37% of the dose), metabolite oxime (13 - 18% of the dose) and the parent oxamyl (7 - 11% of the dose).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：E组 人类非致癌性证据

Cancer Classification: Group E Evidence of Non-carcinogenicity for Humans

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒药 - 氨基甲酸酯

Other Poison - Carbamate

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

毒理性

• 毒性数据

LC50 (大鼠) = 170 毫克/立方米/小时

LC50 (rat) = 170 mg/m3/1h

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

毒理性

• 解毒与急救

氨基甲酸酯中毒的临床处理方法与有机磷中毒相似；主要区别在于通常不推荐使用普瑞洛霉素。/氨基甲酸酯/

The clinical approach to carbamate toxicity is similar to that for organophosphate poisoning; the major exception is that pralidoxime usually is not recommended. /Carbamates/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

稳定：评估气道的充足性和通风情况，并根据需要使用氧气、吸痰、插管、人工通气、静脉输液线和心脏监护器。/氨基甲酸酯/

Stabilization: Assess the adequacy of the airway and ventilation and use oxygen, suction, intubation, artificial ventilation, intravenous lines, and cardiac monitors as needed. /Carbamates/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当给予哺乳期山羊(14)C-草胺磷时，大部分剂量会迅速通过尿液和粪便排出。也会形成一些(14)CO2。在乳汁、血液、尿液或组织中没有检测到完整的草胺磷或相关代谢物；然而，(14)C被整合到乳糖、酪蛋白、甘油三酯脂肪和血液及组织中的蛋白质氨基酸中。

When (14)C-oxamyl was administered to lactating goats, most of the dose was rapidly eliminated via urine and feces. Some (14)CO2 also formed. No intact oxamyl or related metabolites were detected in milk, blood, urine or tissues; however, (14)C was incorporated into lactose, casein, triglyceride fats, and amino acids of protein in blood and tissues.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在注射14C草胺磷后，小鼠在6小时内排出了75.5%的活性。到96小时时，已有88.7%通过尿液排出，7.7%通过粪便排出。在注射后6小时和72小时，尿液中的有机溶性放射性物质分别占总放射性的24.7%和6.5%。识别出的有机溶性化合物包括草胺磷和甲基N'-甲基-N-(甲基羧基氧基)-1-硫代草酰胺咪唑烷......

Following ip injection of (14)C oxamyl, mice excreted 75.5% of the activity within 6 hours. By 96 hours, 88.7% had been excreted in the urine and 7.7% in the feces. At 6 and 72 hours after injection, organosoluble radioactive material constituted 24.7 and 6.5%, respectively, of the total radioactivity in the urine. The organosoluble cmpds identified included oxamyl and methyl N'-methyl-N-(methyl(carbomyl)oxy)-1-thiooxamimidate ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

关于通过吸入或口服途径暴露后，氨基甲酸盐在哺乳动物的各种器官和组织中的分布，目前可用的信息很少。据报道含有残留物的器官包括肝脏、肾脏、大脑、脂肪和肌肉。在大鼠中，半衰期约为3-8小时。看来人类通过尿液排出氨基甲酸盐的速度也很快，而且人类的代谢途径与大鼠相同。/氨基甲酸酯类杀虫剂/

Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠代谢研究中，SD大鼠（每性别每组5只动物）通过灌胃接受了单次口服剂量的14C-草酰胺（1毫克/千克）。在大约24小时给药后，约80%的放射性物质通过尿液排出，在大约168小时后，约91%的剂量通过尿液排出。在粪便中发现的剂量不到3%，在大鼠尸体中发现的剂量大约为1%。除了肌肉和皮肤外，在任何检查的组织中发现的剂量都不到1%。数据表明，草酰胺口服给药后被迅速吸收，并且快速代谢并通过尿液排出。在消除模式上没有性别差异，并且草酰胺或其代谢物在检查的任何组织中基本上没有蓄积。

In a rat metabolism study, SD rats (5 animals/sex/group) received a single oral dose of 14C-oxamyl (1 mg/kg) by gavage. Approximately 80% of the administered radioactivity was eliminated in the urine after 24 hours of dosing, and approximately 91% of the dose was eliminated in the urine by 168 hours. Less than 3% of the dose was found in the feces, and approximately 1% of the dose was found in the carcass. Except for muscle and skin, less than 1% of the dose was found in any tissue examined. The data indicated that oxamyl was readily absorbed with oral administration and rapidly metabolized and eliminated in the urine. There was no sex difference m the pattern of elimination, and there was essentially no sequestration of oxamyl or its metabolites in any tissue examined.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(1-14C)草酰亚胺在哺乳山羊体内的代谢命运进行了研究。实验动物连续五天口服给予31 ppm草酰亚胺的饮食负荷。大部分放射性物质通过尿液（45.3%）和粪便（7.2%）排出。可食用组织（肝脏、肾脏、肌肉和脂肪）和牛奶中的(14C)草酰亚胺当量分别占剂量的6.7%和10.2%。一小部分剂量（1.9%）以挥发性代谢物（主要是14CO2）的形式呼出。在组织、牛奶或尿液中未检测到草酰亚胺或任何密切相关的代谢物。观察到(1-14C)草酰亚胺的大量降解/代谢。放射性硫氰酸盐是牛奶以及所有组织样本的甲醇/水提取物中鉴定出的主要代谢物。

The metabolic fate of (1-14C)oxamyl in a lactating goat was investigated. The test animal was administered five consecutive daily doses orally at 31 ppm oxamyl dietary burden. Most of the radioactivity was eliminated via urine (45.3%) and feces (7.2%). (14C)Oxamyl equivalents in edible tissues (liver, kidney, muscle, and fat) and in milk accounted for 6.7 and 10.2% of the dose, respectively. A small percentage (1.9%) of the dose was exhaled as volatile metabolites (primarily 14CO2). No oxamyl nor any closely related metabolites were detected in tissues, milk, or urine. Extensive degradation/metabolism of (1-14C)oxamyl was observed. Radioactive thiocyanate was the major metabolite identified in the milk as well as in the methanol/water extracts for all tissue samples.

来源:Hazardous Substances Data Bank (HSDB)

表征谱图