3,3-dimethyl-1-methylthio-2-butanone O-methylcarbamoyloxime | 75013-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 3,3-dimethyl-1-methylthio-2-butanone O-methylcarbamoyloxime
• 英文别名: thiofanox；3,3-Dimethyl-1-(methylthio)-2-butanone O-(methylcarbamoyl)oxime；[(Z)-(3,3-dimethyl-1-methylsulfanylbutan-2-ylidene)amino] N-methylcarbamate
• CAS: 75013-97-7
• 化学式: C₉H₁₈N₂O₂S
• 分子量: 218.32
• InChiKey: FZSVSABTBYGOQH-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

棉花植物的完全展开叶片在田间单独处理了(35)S标记的DIAMOND SHAMROCK (3,3-二甲基)-1-(甲硫基)-2-丁酮O-(甲基碳氧基)肟)。形成了磺酰基和亚磺酰基。... 从处理过的种子生长的幼苗得到了与成熟植物和在土壤中得到的相同结果。

FULLY EXPANDED LEAVES OF COTTON PLANTS GROWN IN THE FIELD WERE TREATED INDIVIDUALLY WITH (35)S-LABELED DIAMOND SHAMROCK (3,3-DIMETHYL)-1-(METHYLTHIO)-2- BUTANONE O-(METHYLCARBOMYL) OXIME). THE SULFONE & SULFOXIDE WERE FORMED. ... SEEDLINGS GROWN FROM TREATED SEED GAVE SAME RESULTS AS THOSE OBTAINED IN MATURE PLANTS & IN SOIL.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在土壤中，DS-15647的化学变化与在植物中发现的相似，但它们进行得较慢。经过表面处理棉花种子，使用的是DIAMOND SHAMROCK (3,3-二甲基)-1-(甲硫基)-2-丁酮O-(甲基碳氧基)氧化物)，并在温室中种植，一天后吸收了20%的剂量。从用处理过的种子种植的植物中回收的主要是亚砜和砜衍生物。

IN SOIL THE CHEM CHANGES OF DS-15647 WERE SIMILAR TO THOSE FOUND IN PLANTS, BUT THEY PROCEEDED AT SLOWER RATES. COTTON SEEDS THAT HAD BEEN SURFACE TREATED WITH DIAMOND SHAMROCK (3,3-DIMETHYL)-1-(METHYLTHIO)-2-BUTANONE O-(METHYLCARBOMYL) OXIDE) & PLANTED IN THE GREENHOUSE ABSORBED 20% OF THE DOSE AFTER 1 DAY. THE SULFOXIDE AND SULFONE DERIVATIVES WERE THE PRIMARY PRODUCTS RECOVERED FROM PLANTS GROWN FROM THE TREATED SEEDS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在三种代谢物中：3,3-二甲基-1-(甲硫亚基)-2-丁酮，O-((甲基氨基)碳酰基)肟基亚砜；3,3-二甲基-1-(甲硫基)-2-丁酮 O-((二甲氨基)碳酰基)肟基亚磺酸；以及3,3-二甲基-1-(甲硫基)-2-丁酮 O-((羟甲基氨基)碳酰基)肟基羟甲基亚磺酸，在大鼠体内进行研究，发现噻吩氧的羟甲基亚磺酸代谢物是最有效的代谢物，可以抑制血浆和红细胞乙酰胆碱酯酶。

OF THE THREE METABOLITES: 3,3-DIMETHYL-1-(METHYLSULFINYL)-2-BUTANONE, O-((METHYLAMINO) CARBONYL)OXIME SULFOXIDE; 3,3-DIMETHYL-1-(METHYLSULFONYL)-2-BUTANONE O-((DIMETHYLAMINO)CARBONYL)OXIME SULFONE; AND 3,3-DIMETHYL-1-(METHYLSULFONYL) -2-BUTANONE O-((HYDROXYMETHYLAMINO)CARBONYL)OXIME HYDROXYMETHYL SULFONE, INVESTIGATED IN RATS, THE HYDROXYMETHYL SULFONE METABOLITE OF THIOFANOX WAS THE MOST POTENT METABOLITE TO INHIBIT PLASMA & RED BLOOD CELL ACETYLCHOLINESTERASE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

代谢的主要途径似乎是硫代氧化酶转化为其亚砜，随后进一步氧化为其砜。初始反应的速率明显快于第二个反应，特别是在植物中。还观察到氨基甲酰部分水解为相应的羟肟酸。基于LD50值，在大鼠中亚砜基氨基甲酸酯的毒性比硫代氧化酶及其相关化合物要大。

The major route of metabolism appears to be the oxidation of thiofanox to its sulfoxide & the subsequent oxidation to its sulfone. The rate of the initial reaction is decisively more rapid than that of the second, particularly in plants. Hydrolysis of carbamoyl moieties to their resulting oximes is also observed. ... Sulfonyl oxime carbamate is ... /more/ toxic /than thiofanox & related compounds in rats based on LD50 values/.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒药 - 氨基甲酸盐

Other Poison - Carbamate

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

毒理性

• 毒性数据

LC50 (rat) = 70 mg/m3 大、小白鼠急性经呼吸道LC50为7000mg/m3，大鼠为3700mg/m3。小鼠吸入最低中毒剂量（TCL0）为950mg/kg。

LC50 (rat) = 70 mg/m3

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

毒理性

• 相互作用

当2,2-二甲基-1,3-苯并二氧杂环戊烷-4-基-N-甲基氨基甲酸酯与颗粒状3,3-二甲基-1-甲硫基-2-丁酮-O-甲基氨基甲酸酯同时施用于甜菜上时，它控制了豆蚜，并且比单独施用任一化合物具有更好的协同作用。

WHEN 2,2-DIMETHYL-1,3-BENZODIOXOL-4-YL-N-METHYLCARBAMATE WAS APPLIED SIMULTANEOUSLY WITH GRANULAR 3,3-DIMETHYL-1-METHYLTHIO-2-BUTANONE O-METHYLCARBAMOYLOXIME ON SUGAR BEETS IT CONTROLLED APHIS FABAE AND HAD A SYNERGISTIC ACTION BETTER THAN DID EITHER CMPD APPLIED INDIVIDUALLY.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在90天喂养试验中：比格犬的无效应水平（NEL）为每日1.0毫克/千克；接受100毫克/千克饮食的大鼠体重增长未受影响。

IN 90-DAY FEEDING TRIALS: THE NEL /NO-EFFECT-LEVEL/ IN BEAGLE DOGS WAS 1.0 MG/KG DAILY; THE WEIGHT GAIN OF RATS RECEIVING 100 MG/KG DIET WAS NOT AFFECTED.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在90天的喂养试验中，大鼠的无效应水平为1毫克/千克/天。在4.0毫克/千克/天时，出现了可逆性胆碱酯酶抑制的临床症状，持续时间为3-4小时。

In 90 day feeding trials, no-effect level for rats was 1 mg/kg/day. Clinical symptoms of reversible cholinesterase inhibition at 4.0 mg/kg/day, lasting for 3-4 hours.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-1-methylthio-2-butanone O-methylcarbamoyloxime 生成 异丁烷
  参考文献：
  名称：

  CORKINS, H. G.;STORAGE, L.;OSGOOD, E. R.;DEPOMPEI, M. F.;MANNION, J. J.;K+, J. AGR. AND FOOD CHEM., 1982, 30, N 2, 267-273

  摘要：

  DOI：

文献信息

• COMPOSITION AND METHOD FOR PROTECTING PLANTS FROM PHYTOPATHOGENIC FUNGI
  申请人：UNIROYAL CHEMICAL COMPANY, Inc.

  公开号：EP0625008B1

  公开（公告）日：1997-05-02
• BIOLOGICAL CONTROL OF PLANT FUNGAL INFECTIONS
  申请人：Agritope, Inc.

  公开号：EP0938260A1

  公开（公告）日：1999-09-01
• US4146646A
  申请人：——

  公开号：US4146646A

  公开（公告）日：1979-03-27
• US4097526A
  申请人：——

  公开号：US4097526A

  公开（公告）日：1978-06-27
• US4248795A
  申请人：——

  公开号：US4248795A

  公开（公告）日：1981-02-03