(±)-Naled
描述
(±)-Naled is an Agricultural insecticide, acaricide, bactericide and fungicide
(±)-Naled belongs to the family of Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.
类别
"Pesticide", "Food Toxin", "Synthetic Toxin"
同义词
"(±)-naled", "1,2-Dibromo-2,2-Dichloroethyl dimethyl phosphate", "1,2-Dibromo-2,2-dichloroethyl dimethyl phosphatic acid", "Alvora", "Arthodibrom", "Bromchlophos", "Bromex", "Bromex 50", "BRP", "Dibrom", "Dibromfos", "Dimethyl 1,2-dibromo-2,2-dichloroethyl phosphate", "dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate", "Flibol ex", "Fosbrom", "Hibrom", "Naled", "Nikabrom", "O,O-dimethyl O-2,2-dichloro-1,2-dibromoethyl phosphate", "O,O-Dimethyl-O-(1,2-dibromo-2,2-dichloroethyl)phosphate", "O-(1,2-Dibromo-2,2-dichloroethyl)-O,O-dimethyl phosphate", "o-Dibrom 8E", "Ortho Dibrom 8E", "Ortho-dibrom", "Orthodibromo", "Phosphoric acid, 1,2-dibromo-2,2-dichloroethyl dimethyl ester"
IUPAC 名称
1,2-dibromo-2,2-dichloroethyl dimethyl phosphate
简化分子线性输入规范
COP(=O)(OC)OC(Br)C(Cl)(Cl)Br
InChI 标识符
InChI=1/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3
键
InChIKey=BUYMVQAILCEWRR-UHFFFAOYNA-N
大分类
Organic acids and derivatives
类型
Organic phosphoric acids and derivatives
另外分类
"Alkyl bromides", "Alkyl chlorides", "Hydrocarbon derivatives", "Organic oxides", "Organobromides", "Organochlorides", "Organooxygen compounds"
取代基
"Aliphatic acyclic compound", "Alkyl bromide", "Alkyl chloride", "Alkyl halide", "Hydrocarbon derivative", "Organic oxide", "Organic oxygen compound", "Organobromide", "Organochloride", "Organohalogen compound", "Organooxygen compound", "Trialkyl phosphate"
分子框架
Aliphatic acyclic compounds
外部描述符
"Organophosphorus insecticides", "dialkyl phosphate", "organobromine compound", "organochlorine compound", "organophosphate insecticide"
地位
Detected and Not Quantified
蜂窝位置
"Cytoplasm", "Extracellular", "Membrane"
外貌
Colorless solid or straw-colored liquid with a slightly pungent odor. (L1193)
熔点/沸点/溶解度
26°C/110 °C at 5 mm Hg (technical) /0.0015 mg/mL [USDA PESTICIDE PROP DATABASE]
暴露途径
Oral (L1193) ; inhalation (L1193) ; dermal (L1193)
毒性机制
(±)-Naled 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.
致癌性
No indication of carcinogenicity to humans (not listed by IARC).
用途/来源
Major routes of exposure are by application from fog and mist sprayers. The use of application by aircraft increases the potential for exposure of humans and nontarget organisms to naled. Human exposure to naled during mixing, handling, application, and reentry operations can be minimized by use of approved respirators and other protective clothing. (L1193)
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
If inhaled, effects on the respiratory system and the eyes are the first to appear. (L1193)
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.
创建于
2009-03-06 18:58:20 UTC
更新于
2014-12-24 20:21:23 UTC