毒虫畏 | 470-90-6

• 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: 毒虫畏
• 中文别名: 毒虫威；2-氯-1-(2,4-二氯苯基)乙烯基二乙基磷酸酯；杀螟威；代草克；杀螟畏
• 英文名称: chlorfenvinphos
• 英文别名: chlorfenvinfos；Birlan；[2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate
• CAS: 470-90-6
• 化学式: C₁₂H₁₄Cl₃O₄P
• 分子量: 359.574
• InChiKey: FSAVDKDHPDSCTO-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  明火可燃，受热会释放出有毒的氧化磷和氯化物气体。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

... CHLORFENVINPHOS ... 在哺乳动物中被广泛地通过O-脱烷基化解毒。

... CHLORFENVINPHOS ... /IS/ DETOXIFIED IN MAMMALS EXTENSIVELY BY O-DEALKYLATION.

来源:Hazardous Substances Data Bank (HSDB)

代谢

来自兔肝的微体与氯芬vinfos一起孵化。通过羟基化使酯键的氧化裂解发生，生成1-羟基乙基磷酸三酯。这个中间体断裂，生成2-氯-1-(2,4-二氯苯基)乙烯基乙基氢磷酸。C-O键的氧化裂解而不是P-O键的水解，产生了乙醛。

MICROSOMES FROM RABBIT LIVERS WERE INCUBATED WITH CHLORFENVINPHOS. OXIDATIVE CLEAVAGE OF ESTER BOND ... /OCCURRED/ VIA HYDROXYLATION ... TO GIVE 1-HYDROXYETHYL PHOSPHATE TRIESTER. THIS ... INTERMEDIATE BROKE DOWN ... TO 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL ETHYL HYDROGEN PHOSPHATE. OXIDATIVE CLEAVAGE OF THE C-O BOND, RATHER THAN HYDROLYSIS OF THE P-O BOND, YIELDED ACETALDEHYDE ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠和狗口服给药后...在大鼠中，32.3%的剂量由2-氯-1-(2,4-二氯苯基)乙烯基单乙基磷酸酯承担；41%由1-(2',4'-二氯苯基)乙基β-D-葡萄糖苷尿酸承担；7%由2,4-二氯扁桃酸承担；2.6%由2,4-二氯苯乙醇葡萄糖苷酸承担；以及4.3%由2,4-二氯马尿酸承担。在狗中，这分别是69.6%的2-氯-1-(2,4-二氯苯基)乙烯基单乙基磷酸酯；3.6%的1-(2',4'-二氯苯基)乙基β-D-葡萄糖苷尿酸；13.4%的/未识别化合物/；2.7%的2,4-二氯苯乙醇葡萄糖苷酸。静脉给药后，氯芬磷迅速代谢为其O-去乙基类似物（2-氯-1-(2,4-二氯苯基)乙烯基单乙基磷酸酯）（83%），2,4-二氯扁桃酸（9%）和1-(2',4'-二氯苯基)乙基β-D-葡萄糖苷尿酸（8%）在狗中。

AFTER ORAL ADMIN TO RATS AND DOGS...IN RATS, 32.3% OF DOSE WAS ACCOUNTED FOR BY 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE; 41% BY 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID; 7% BY 2,4-DICHLOROMANDELIC ACID; 2.6% BY 2,4-DICHLOROPHENYLETHANEDIOL GLUCURONIDE; AND 4.3% BY 2,4-DICHLOROHIPPURIC ACID. IN DOGS THIS WAS 69.6% 2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE; 3.6% 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID; 13.4% /UNIDENTIFIED COMPD/; 2.7% 2,4-DICHLOROPHENYLETHANEDIOL GLUCURONIDE. AFTER IV ADMINISTRATION, CHLORFENVINPHOS WAS RAPIDLY METABOLIZED TO O-DESETHYL ANALOG (2-CHLORO-1-(2,4-DICHLOROPHENYL) VINYL MONOETHYL PHOSPHATE) (83%), 2,4-DICHLOROMANDELIC ACID (9%), AND 1-(2',4'-DICHLOROPHENYL) ETHYL BETA-D-GLUCOPYRANOSIDURONIC ACID (8%) IN DOGS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氯芬vinfos在人体内的一个代谢物是脱乙基氯vinfos。

One metabolite of chlorfenvinphos in humans is desethyl chlorvinphos.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 吸入症状

瞳孔收缩、肌肉痉挛、过度流涎。出汗。恶心。头晕。呼吸困难。头痛。抽搐。昏迷。症状可能延迟出现。

Pupillary constriction, muscle cramp, excessive salivation. Sweating. Nausea. Dizziness. Laboured breathing. Headache. Convulsions. Unconsciousness. Symptoms may be delayed.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

可能会被吸收！请参见吸入部分。

MAY BE ABSORBED! See Inhalation.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

模糊的视力。

Blurred vision.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 摄入症状

腹部绞痛。腹泻。呕吐。虚弱。抽搐。请参阅吸入部分。

Abdominal cramps. Diarrhoea. Vomiting. Weakness. Convulsions. See Inhalation.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

牛只在施用(32)P-标记的氯芬磷后，尿液中的放射性物质浓度在处理后3小时达到峰值。...在暴露的羊器官中，氯芬磷的残留物低于检测限。残留水平从未达到0.1 ppm。在大鼠和狗口服给药后，(14)C-氯芬磷被迅速代谢并排出体外。大约90%通过尿液排出；其余通过粪便排出，还有一小部分通过呼出的气体排出。...研究已经表明，这种化合物会与哺乳动物血液血浆中的蛋白质以及家蝇头部的匀浆发生反应并与之结合。

PEAK CONCN OF RADIOACTIVE MATERIAL IN URINE OF STEERS, AFTER SPRAY APPLICATION OF (32)P-LABELED CHLORFENVINPHOS, OCCURRED IN SAMPLES AT 3 HR POST-TREATMENT. ... RESIDUES OF CHLORFENVINPHOS ... WERE BELOW LIMITS OF DETECTION IN ORGANS OF EXPOSED SHEEP. RESIDUE LEVELS NEVER REACHED 0.1 PPM. AFTER ORAL ADMIN TO RATS & DOGS, (14)C CHLORFENVINPHOS WAS RAPIDLY METABOLIZED AND EXCRETED. ABOUT 90% WAS ELIMINATED IN URINE; REMAINDER, VIA FECES AND, TO A LESSER EXTENT, VIA EXPIRED GASES. ... STUDIES HAVE SHOWN THAT THIS COMPD REACTED WITH AND WAS BOUND BY PROTEINS IN BLOOD PLASMA OF MAMMALS AND IN HOMOGENATES OF HOUSE FLY HEADS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

以112毫克/小时/人的剂量水平应用于左前臂......在接触后24小时测得的血药浓度达到或超过0.012 ppm。......70.8毫克/小时/人导致......接触后24小时血药浓度为0.006 ppm。

Dosage levels of 112 mg/hr/man /applied to left forearm/ ... produced blood levels of 0.012 ppm or more measured 24 hr after exposure. ... 70.8 mg/hr/man caused ... a blood level of 0.006 ppm 24 hr after exposure.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

口服剂量高达1毫克/千克对大鼠的胆碱酯酶或觉醒-睡眠周期没有影响。在2毫克/千克以上的剂量下，大脑和红细胞的胆碱酯酶活性显著降低，自发脑电图显示出明显的觉醒模式，并抑制了睡眠的特征性曲线。大脑胆碱酯酶的最大抑制发生在给药后3小时，持续超过72小时。

Oral dosages as high as 1 mg/kg did not affect cholinesterase or the awake-sleep cycle of rats. At dosages over 2 mg/kg, the cholinesterase activities of both brain & red cells were significantly decr, & the spontaneous EEG showed a prominent arousal pattern with suppression of curves characteristic of sleep. Maximal inhibition of brain cholinesterase occurred 3 hr after dosing & lasted for more than 72 hr.

来源:Hazardous Substances Data Bank (HSDB)