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硫环磷 | 947-02-4

中文名称
硫环磷
中文别名
硫环磷乳油;O,O-二乙基-N-(1,3-二硫杂茂-2-叉基)硫酰胺;氧环胺磷;棉安磷乳油;乙基硫环磷乳油;棉安磷
英文名称
phosfolan
英文别名
2-(diethoxyphosphinylimino)-1,3-dithiolane;Caswell No. 268B;N-diethoxyphosphoryl-1,3-dithiolan-2-imine
硫环磷化学式
CAS
947-02-4
化学式
C7H14NO3PS2
mdl
——
分子量
255.299
InChiKey
ILBONRFSLATCRE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.6
  • 重原子数:
    14
  • 可旋转键数:
    5
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.86
  • 拓扑面积:
    98.5
  • 氢给体数:
    0
  • 氢受体数:
    6

ADMET

代谢
在植物和动物中,/磷酯素/ 在 N-P 键处被代谢成毒性较低、水溶性的化合物。
... IN PLANTS & ANIMALS, /PHOSFOLAN/ IS METABOLIZED AT THE N-P BOND TO LESS TOXIC, WATER-SOLUBLE COMPOUNDS.
来源:Hazardous Substances Data Bank (HSDB)
代谢
单次口服剂量(2毫克/千克)给予大鼠的[(14)C-(C=N)]磷酰亚胺迅速代谢,主要代谢产物为硫氰化物和二氧化碳(20%)。...确定了十四种次要的尿液代谢物...磷酰亚胺生物转化的可能初始步骤是P-N裂解和/或S-氧化。
A SINGLE ORAL DOSE (2 MG/KG) TO RAT OF [(14)C-(C=N)]PHOSFOLAN WAS RAPIDLY METABOLIZED TO GIVE AS MAJOR METABOLITES THIOCYANATE AND CARBON DIOXIDE (20%). ... FOURTEEN MINOR URINARY METABOLITES WERE IDENTIFIED ... THE LIKELY INITIAL STEPS IN BIOTRANSFORMATION OF PHOSFOLAN ARE P-N CLEAVAGE &/OR S-OXIDATION.
来源:Hazardous Substances Data Bank (HSDB)
代谢
两种14C-二硫代烷类杀虫剂(phosfolan和mephosfolan)在亚胺碳位点上标记的研究结果如下。在这些研究中使用了大鼠、棉花植物和模拟稻田环境。在大鼠中,两种杀虫剂的主要降解途径是水解为亚胺二硫代烷,然后转化为硫氰酸盐,最后为CO2。在用mephosfolan处理的棉花植物中,亚胺二硫代烷环上甲基基团羟基化并与葡萄糖苷结合是一个重要的途径。当稻田环境被mephosfolan处理时,在水稻植物中发现了mephosfolan,但没有在稻谷中积累。水稻植物迅速吸收mephosfolan,降解它,并将14C-碳整合到天然植物产品中。在稻田环境中,鱼类很容易将mephosfolan代谢为硫氰酸盐和许多极性代谢物。
Results are presented of studies on the metabolism of two (14)C-dithiolane insecticides (phosfolan and mephosfolan) labeled in the imido carbon position. Rats, cotton plants, and a simulated rice paddy environment were used in the studies. In rats, both insecticides showed their major degradation route to be hydrolysis to iminodithiolane, then to thiocyanate, then CO2. In cotton plants treated with mephosfolan, hydroxylation of the methyl moiety of the iminodithiolane ring and conjugation as glucoside was a significant pathway. When a rice paddy environment was treated with mephosfolan, mephosfolan was found in the rice plants, but did not accumulate in the rice grain. The rice plants assimilated mephosfolan rapidly, degraded it, and incorporated the (14)C-carbon into the natural plant products. Mephosfolan was readily metabolized by fish in the paddy environment into the thiocyanate and many polar metabolites.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 副作用
其他毒物 - 有机磷酸酯
Other Poison - Organophosphate
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 人类毒性摘录
接触敌百虫的工人显示出红细胞胆碱酯酶活性显著降低。在首次接触后的一小时内,胆碱酯酶活性的降低在低暴露组为13.6-43.8%,在高暴露组为31.1-43.8%。大约在48小时后,被抑制的酶活性恢复了大约一半。之后的恢复速度较慢,大约需要3到4周才能恢复到接触前的水平。
WORKERS EXPOSED TO PHOSFOLAN SHOWED A HIGH REDUCTION IN CHOLINESTERASE ACTIVITY OF THE ERYTHROCYTES. THIS DECR IN THE ACTIVITY AT THE END OF THE FIRST HR RANGED 13.6-43.8% AND 31.1-43.8% IN THE LESS EXPOSED AND HIGHLY EXPOSED WORKERS, RESPECTIVELY. ABOUT HALF OF THE INHIBITED ENZYME ACTIVITY WAS RECOVERED AFTER 48 HR. THE RATE OF RECOVERY WAS SLOW AFTER THAT & IT TOOK APPROX 3-4 WK TO RETURN TO PREEXPOSURE LEVEL.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
症状学:1. 恶心...呕吐,腹痛,腹泻,过度流涎... 2. 头痛,眩晕,晕厥和虚弱。3. 鼻漏和胸部紧缩感在吸入暴露中常见。4. 视力模糊或暗淡,瞳孔缩小...流泪,睫状肌痉挛,调节功能丧失和眼痛...瞳孔散大...有时可见...可能是由于交感肾上腺释放。5. 心动过缓或心动过速。不同程度的心房室传导阻滞有描述,以及房性心律失常。6. 肌肉协调性丧失,言语不清,肌肉颤动和抽搐(尤其是舌头和眼睑,以及全身严重无力。7. 精神混乱,定向障碍和嗜睡。8. 呼吸困难,唾液和呼吸道粘液过度分泌,口鼻泡沫,发绀,肺啰音和哮鸣音以及高血压(可能是由于窒息)。9. 随机抽动动作,失禁,惊厥和昏迷。10. 死亡主要是由于呼吸中枢衰竭、呼吸肌麻痹、剧烈支气管收缩或三者共同引起的呼吸停止。/对硫磷/
Symptomatology: 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis ... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain ... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/
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,每天接受1毫克/千克剂量的狗没有显示出任何临床症状。
IN 90-DAY FEEDING TRIALS DOGS RECEIVING 1 MG/KG DAILY SHOWED NO CLINICAL SYMPTOMS.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
使用赛欧兰处理的苜蓿干草在处理后一年被喂给牛。胆碱酯酶活性受到抑制,并且在停止喂食受赛欧兰污染的干草后的三个月内,胆碱酯酶活性才恢复正常水平。
CYOLANE-TREATED ALFALFA HAY WAS FED TO COW 1 YR AFTER TREATMENT OF ALFALFA. CHOLINESTERASE WAS DEPRESSED & DID NOT RETURN TO NORMAL LEVELS UNTIL 3 MO AFTER FEEDING OF CYOLANE-CONTAMINATED HAY HAD BEEN DISCONTINUED.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
单次口服给大鼠2毫克/千克的(14)C-(C=N)磷酰亚胺(草胺磷)后,该物质被迅速代谢...硫氰酸盐出现在肝脏、肾脏和脂肪中,并且也通过尿液排出(24%)。
A SINGLE ORAL DOSE (2 MG/KG) TO THE RAT OF (14)C-(C=N)PHOSFOLAN (CYOLANE) WAS RAPIDLY METABOLIZED ... THIOCYANATE WAS PRESENT IN LIVER, KIDNEY, & FAT, & WAS ALSO EXCRETED IN THE URINE (24%).
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
CYOLANE IS ... ACTIVE ... IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION. 赛欧兰是...活性的...通过植物的根系和叶面吸收。
CYOLANE IS ... ACTIVE ... IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION.
来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

可防治棉、麦、水稻、大豆、甜菜、果树、茶等作物的害虫,对蚜虫、红蜘蛛有良好防效,也可拌种防治地下害虫。

合成制备方法

2-亚氨基-1,3-二硫戊环盐酸盐与O,O-二乙基硫代磷酰氯在苯水混合溶剂中搅拌。约半小时内加入乙酸钠水溶液后,搅拌并静置分层。分离苯层,水层用乙醚萃取一次,合并苯层和萃取液,得到所需产物。该方法每吨所需的原材料为2,380公斤:1080kg/吨的2-亚氨基-1,3-二硫戊环盐酸盐、1300kg/吨的O,O-二乙基硫代磷酰氯。

用途简介 用途

内吸性杀虫剂,主要用于防治刺吸式口器害虫、螨类和鳞翅目幼虫。该药剂在土壤、植物和动物体内无持效性,在N-P键处代谢,转化为无毒的可溶于水的化合物。可用于防治棉、麦、水稻、大豆、甜菜、果树及茶等作物上的害虫,特别对蚜虫和红蜘蛛有良好的防治效果,也可以拌种用于防治地下害虫。

反应信息

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文献信息

  • [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。
  • [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
    申请人:SYNGENTA PARTICIPATIONS AG
    公开号:WO2011101402A1
    公开(公告)日:2011-08-25
    The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.
    本发明涉及化合物式(I),其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基;以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义;或其盐或N-氧化物。此外,本发明涉及制备化合物式(I)的过程和中间体,包括化合物式(I)的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物,以及使用化合物式(I)控制昆虫、螨虫、线虫和软体动物害虫的方法。
  • ISOXAZOLINE DERIVATIVES AS INSECTICIDES
    申请人:Pitterna Thomas
    公开号:US20120316124A1
    公开(公告)日:2012-12-13
    The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 17 , R 18 , R 19 and R 20 are as defined in claim 1 ; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.
    本发明涉及化合物式(I),其中P为P1、P2、杂环烷基或被1至5个Z取代的杂环烷基;以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1所定义;或其盐或N-氧化物。此外,本发明涉及制备化合物式(I)的过程和中间体,包括化合物式(I)的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物,以及使用化合物式(I)控制昆虫、螨虫、线虫和软体动物害虫的方法。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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