Guthion
描述
Guthion, also called azinphos-methyl, is a synthetic organophosphorous pesticide. It has been used on many different crops, especially apples, pears, cherries, peaches, almonds, and cotton. Due to its toxicity, its use has been banned or tightly regulated in most areas today. (L580)
类别
"Pesticide", "Food Toxin", "Synthetic Toxin"
同义词
"3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioate", "Azimil", "Azinfos-methyl", "Azinophos-methyl", "Azinphos", "Azinphos methyl", "Azinphos methyl mixture", "Azinphos-me", "Azinphos-metile", "Azinphosmethyl", "Beetle buster", "Benzotriazinedithiophosphoric acid dimethoxy ester", "Carfene", "Cotneon", "Cotnion", "Cotnion methyl", "Crysthyon", "Dimethyl dithiophosphoric acid N-methylbenzazimidyl ester", "Dimethyldithiophosphoric acid N-methylbenzazimide ester", "Go thnion", "Gothnion", "Gusathion", "Gusathion methyl", "Gusthion m", "Guthion (azinphos-methyl)", "Guthion mixture", "Guthion(r)", "Guthion, gusation", "Gution", "Metazintox", "Methyl azinphos", "Methyl gusathion", "Methyl guthion", "Methylazinphos", "Methylgusathion", "Methyltriazotin", "Metiltriazotion", "N-Methylbenzazimide, dimethyl dithiophosphoric acid ester", "N-methylbenzazimide, dimethyldithiophosphoric acid ester", "Nitrinal", "O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate", "O,O-dimethyl S-(be nzaziminomethyl) dithiophosphate", "O,O-dimethyl S-(benzaziminomethyl) dithiophosphate", "O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate", "O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat", "O,O-dimethyl-s-(benzaziminomethyl) dithiophosphate", "Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester", "Zinphos methyl"
IUPAC 名称
O,O-dimethyl {[(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)methyl]sulfanyl}phosphonothioate
传统名称
O,O-dimethyl [(4-oxo-1,2,3-benzotriazin-3-yl)methyl]sulfanylphosphonothioate
简化分子线性输入规范
COP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O
InChI 标识符
InChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3
键
InChIKey=CJJOSEISRRTUQB-UHFFFAOYSA-N
大分类
Organoheterocyclic compounds
子类
Benzotriazine organothiophosphates
直接大类
Benzotriazine organothiophosphates
另外分类
"1,2,3-triazines", "Azacyclic compounds", "Benzenoids", "Dithiophosphate O-esters", "Dithiophosphate S-esters", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Lactams", "Organic oxides", "Organonitrogen compounds", "Organooxygen compounds", "Organopnictogen compounds", "Organothiophosphorus compounds", "Sulfenyl compounds", "Triazinones"
取代基
"1,2,3-triazine", "Aromatic heteropolycyclic compound", "Azacycle", "Benzenoid", "Benzotriazine organothiophosphate", "Dithiophosphate o-ester", "Dithiophosphate s-ester", "Heteroaromatic compound", "Hydrocarbon derivative", "Lactam", "Organic dithiophosphate", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Organosulfur compound", "Organothiophosphorus compound", "Sulfenyl compound", "Triazine", "Triazinone"
分子框架
Aromatic heteropolycyclic compounds
外部描述符
"Organophosphorus insecticides", "benzotriazines", "organic thiophosphate", "organothiophosphate insecticide"
地位
Detected and Not Quantified
外貌
Colorless to white crystals.
熔点/沸点/溶解度
73°C//0.0209 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983)]
暴露途径
Oral (L580) ; dermal (L580) ; inhalation (L580)
毒性机制
Guthion 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: 11 mg/kg (Oral, Rat) (T87)
LD50: 4900 ug/kg (Intraperitoneal, Rat) (T14)
LD50: 7500 ug/kg (Intravenous, Rat) (T14)
LD50: 65 mg/kg (Dermal, Mouse) (T14)
LC50: 0.15 mg/L over 4 hours (Inhalation, Rat) (T87)
致死剂量
5 to 50 mg/kg for an adult human. (L591)
致癌性
Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (L135)
用途/来源
Guthion is used as a pesticide, thus exposure usually occurs from eating contaminated food. (L580)
最低风险等级
Acute Inhalation: 0.02 mg/m3 (L134)
Intermediate Inhalation: 0.01 mg/m3 (L134)
Chronic Inhalation: 0.01 mg/m3 (L134)
Acute Oral: 0.01 mg/kg/day (L134)
Intermediate Oral: 0.003 mg/kg/day (L134)
Chronic Oral: 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
Guthion interferes with the nerves and brain normal way. Exposure to very high levels of guthion for a short period in air, water, or food may cause difficulty breathing, chest tightness, vomiting, cramps, diarrhea, blurred vision, sweating, headaches, dizziness, loss of consciousness, and death. (L580)
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/Azinphos-methyl
创建于
2009-03-06 18:58:08 UTC
更新于
2014-12-24 20:21:11 UTC