Chlorpyrifos
描述
Chlorpyrifos (IUPAC name: O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate) is a crystalline organophosphate insecticide. It was introduced in 1965 by Dow Chemical Company and is known by many trade names (see table), including Dursban and Lorsban. It acts on the nervous system of insects by inhibiting acetylcholinesterase. Chlorpyrifos is moderately toxic to humans, and exposure has been linked to neurological effects, persistent developmental disorders, and autoimmune disorders. Exposure during pregnancy retards the mental development of children, and most use in homes has been banned since 2001 in the U.S. In agriculture, it remains one of the most widely used organophosphate insecticides, according to the United States Environmental Protection Agency (EPA).
类别
"Pesticide", "Household Toxin", "Synthetic Toxin"
同义词
"Bonidel", "Brodan", "Chloropyrifos", "Chloropyriphos", "Chlorpyrifos-ethyl", "Chlorpyriphos", "Chlorpyriphos-ethyl", "Chlorpyrofos", "Chlorpyrophos", "Coroban", "Danusban", "Detmol U.A.", "Dowco 179", "Durmet", "Dursban", "Dursban 10CR", "Dursban 2E", "Dursban 4E", "Dursban F", "Dursban R", "Ethyl chlorpyriphos", "Geodinfos", "Killmaster", "Lentrek", "Lorsban", "m-Chlorpyrifos", "O,O-Diaethyl-O-3,5,6-trichlor-2-pyridylmonothiophosphat", "O,O-Diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate", "O,O-Diethyl O-(3,5,6-Trichloro-2-pyridyl) phosphorothioate", "O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioate", "O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphate", "O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate", "Pageant", "Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester", "Piridane", "Pyrinex", "Silrifos", "Spannit", "Stipend", "SuSCon", "Suscon blue", "Suscon green", "Tafaban", "Terial", "Trichlorpyrphos", "Zidil"
IUPAC 名称
O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate
简化分子线性输入规范
CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1
InChI 标识符
InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
键
InChIKey=SBPBAQFWLVIOKP-UHFFFAOYSA-N
大分类
Organic acids and derivatives
类型
Organic thiophosphoric acids and derivatives
子类
Thiophosphoric acid esters
另外分类
"2-halopyridines", "Aryl chlorides", "Azacyclic compounds", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organochlorides", "Organonitrogen compounds", "Organooxygen compounds", "Organopnictogen compounds", "Polyhalopyridines", "Thiophosphate triesters"
取代基
"2-halopyridine", "Aromatic heteromonocyclic compound", "Aryl chloride", "Aryl halide", "Aryl thiophosphate", "Azacycle", "Heteroaromatic compound", "Hydrocarbon derivative", "Organic nitrogen compound", "Organic oxygen compound", "Organochloride", "Organohalogen compound", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Polyhalopyridine", "Pyridine", "Thiophosphate triester"
分子框架
Aromatic heteromonocyclic compounds
外部描述符
"Organophosphorus insecticides", "a small molecule", "chloropyridine", "organic thiophosphate"
地位
Detected and Not Quantified
熔点/沸点/溶解度
42°C//0.00112 mg/mL at 24°C
暴露途径
Oral (L268) ; inhalation (L268) ; dermal (L268)
毒性机制
Chlorpyrifos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
代谢
Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
毒性值
LD50: 102 mg/kg (Oral, Rat) (T42)
LD50: 1233 mg/kg (Dermal, Rabbit) (T42)
LD50: 192 mg/kg (Intraperitoneal, Mouse) (T14)
LC50: 560 mg/m3 over 4 hours (Inhalation, Rat) (T42)
致死剂量
300 mg/kg for an adult human. (T26)
致癌性
Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (L135)
用途/来源
Chlorpyrifos is used as a pesticide. In the home, it is used to control cockroaches, fleas, and termites; it is also used in some pet flea and tick collars. On the farm, it is used to control ticks on cattle and as a spray to control crop pests. (L268)
最低风险等级
Acute Oral: 0.003 mg/kg/day (L134)
Intermediate Oral: 0.003 mg/kg/day (L134)
Chronic Oral: 0.001 mg/kg/day (L134)
健康影响
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
症状
Chlorpyrifos exposure may produce a variety of effects on the nervous system including headaches, blurred vision, lacrimation, excessive salivation, runny nose, dizziness, confusion, muscle weakness or tremors, nausea, diarrhea, and sudden changes in heart rate. High levels may result in severe sweating, loss of bowel control, severe muscle tremors, seizures, loss of consciousness, coma, or death. (L268)
治疗
If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
维基百科链接
http://en.wikipedia.org/wiki/Chlorpyrifos
创建于
2009-03-06 18:58:07 UTC
更新于
2014-12-24 20:21:10 UTC