噻唑磷 | 98886-44-3

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机磷杀虫剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 噻唑磷
• 中文别名: 线螨磷；噻唑膦；O-乙基-S-仲丁基-2-氧代-1,3-噻唑烷-3-基硫代膦酸酯
• 英文名称: fosthiazate
• 英文别名: (RS)-S-sec-butyl-O-ethyl 2-oxo-1,3-thiazolidin-3-ylphosphonothioate；3-[butan-2-ylsulfanyl(ethoxy)phosphoryl]-1,3-thiazolidin-2-one
• CAS: 98886-44-3
• 化学式: C₉H₁₈NO₃PS₂
• 分子量: 283.353
• InChiKey: DUFVKSUJRWYZQP-UHFFFAOYSA-N

物化性质

• 熔点：
  <25 °C
• 沸点：
  bp0.5 198°
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、水（少许）
• 颜色/状态：
  Pale yellow oil
• 蒸汽压力：
  4.20X10-6 mm Hg at 25 °C
• 亨利常数：
  1.74e-10 atm-m3/mole
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。
• 折光率：
  Index of refraction: 1.5334 at 19.6 °C/D
• 保留指数：
  1982.2;1978.3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  97.2
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

代谢

7组Crl:CD BR VAF/Plus大鼠/性别，通过灌胃（2.5 mL/kg玉米油载体）一次性给予18 mg/kg的福司替嗪。不含放射性标记的福司替嗪，其中丁基组的每个甲基碳上都有50%的13C，纯度为99.3%。S-sec-丁基-2-14C标记的福司替嗪纯度为97.7%（通过MS测定）。研究者们评估了48小时内福司替嗪在组织和排泄物中的命运，并表征了尿液中发现的主要代谢物。本研究中的S-sec-丁基-2-14C标记组在排泄物中产生的标签分布与另一项使用环标记14C的研究观察到的分布大致相同。这表明环和丁基取代基都发生降解，释放出可观的CO2（约占总给药剂量的10%）。鉴定出的大分子量代谢物（不包括谷胱甘肽产物）发生了开环反应，通常随后是环硫的甲基化。这种环硫氧化产物，如磺酸、亚磺酸和磺酮，占总给药剂量的约20%。观察到了S-sec-丁基组的几处水解残基，同样显示了硫的氧化，有时伴有硫的甲基化。一些S-secbutyl组残基发生了谷胱甘肽结合，表现为N-乙酰半胱氨酸产物（未进一步表征）...

Groups of 7 Crl:CD BR VAF/Plus rats/sex were dosed once by gavage (in 2.5 mL/kg corn oil vehicle) with fosthiazate at 18 mg/kg. Non-radiolabeled fosthiazate, which contained 13C on 50% of each of the methyl carbons of the butyl group, was 99.3% pure. S-sec-butyl-2-14C-labeled fosthiazate was 97.7% pure (by MS). Investigators evaluated fate of fosthiazate in tissues and excreta over 48 hrs, and characterized major metabolites found in urine. S-sec-butyl-2-14C-labeled group in the present study produced about the same distribution of label in excreta as had been observed in /another study/ which utilized ring-labeled 14C. This suggests that both the ring and the butyl substituents undergo degradation to release appreciable CO2 (about 10% of administered dose). Identified large MW metabolites (excluding glutathione products) underwent ring opening, often with subsequent methylation of the ring sulfur. Products of oxidation of this ring sulfur, such as sulfonic acids, sulfoxides, and sulfones, constituted about 20% of administered dose. There were several observed residues of hydrolysis of the S-sec-butyl group, similarly displaying oxidation of the sulfur, with or without methylation of the sulfur. Some of the S-secbutyl group residues underwent glutathione conjugation and were manifest as N-acetyl cysteine products (not further characterized). ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

七只Crl:CD BR VAF/Plus大鼠/性别通过一次灌胃（在2.2 mL/kg玉米油中）给予22 mg/kg环形-14C-fosthiazate，之前...确定主要代谢物。...观察到九个峰/在溶剂前沿附近迁移/形成了放射性标记组分的最大簇，其中没有一个被鉴定。根据它们在反相HPLC柱上的移动性和碱性离子对试剂对它们移动性的最小影响，它们被认为是小型的、极性的，显然不带电。这些在雄性中构成了42%的给药剂量，在雌性中构成了27%的给药剂量。考虑到标记的CO2输出量、组织中大量的标记保留以及尿液中许多小分子量标记组分的存在，环碳似乎被大量吸收到了碳池中。三种代谢物保留了S-丁基取代基，并发生了噻唑啉环的开环。这些在雄性中构成了约7%的给药标记，在雌性中构成了18%。其中最丰富的是(RS)-S-sec-丁基O-乙基N-(2-甲磺酰乙基)磷酰胺硫代酸酯（指定为BESxP）。一些类似的代谢物已经失去了S-sec-丁基团；特别是O-乙基S-氢N-2(甲磺酰基)乙基磷酰胺硫代酸酯（DBSoS），在雄性中占给药剂量的4.6%，在雌性中占3.0%。乙酰胺（在大约比本研究中观察到的水平高1000倍的量时是大鼠肝致癌物）在雄性和雌性中分别构成了3%和2%的给药剂量。...

Seven Crl:CD BR VAF/Plus rats/sex were dosed once by gavage (in 2.2 mL/kg corn oil) with 22 mg/kg ring-14C-fosthiazate prior to ... identifying major metabolites. ... Nine peaks /were observed/ migrating near to the solvent front formed the largest cluster of radio-labeled components, none of which were characterized. They were considered to be small, polar, and apparently uncharged based on their mobility on a reverse-phase HPLC column and the minimal influence of a basic ion-pairing agent on their mobilities. These constituted 42% of administered dose in males, and 27% of administered dose in females. It appears that ring carbons were substantially assimilated into the carbon pool, considering together the appreciable labeled CO2 output, substantial label retention in tissues, and the presence of many small MW labeled components in urine. Three metabolites retained the S-butyl substituent and underwent opening of the thiazolidinyl ring. Together these constituted about 7% of administered label in males and 18% in females. The most abundant of these was (RS)-S-sec-butyl O-ethyl N-(2-methylsulfinylethyl) phosphoramidothioate (designated BESxP). A couple of analogous metabolites had undergone loss of the S-sec-butyl group; O-ethyl S-hydrogen N-2(methylsulfonyl)ethyl phosphoramidothioate (DBSoS) in particular (4.6% of administered dose in males, and 3.0% in females). Acetamide (a rat liver carcinogen at levels about 1000 x larger than levels observed in this study) constituted 3% and 2% of administered dose in males and females, respectively. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

对氧磷酶（PON1）是有机磷代谢的关键酶。PON1可以通过水解使一些有机磷失活。PON1水解多种有机磷杀虫剂及其活性代谢物，以及神经毒剂如梭曼、沙林和VX。PON1的多态性导致该酯酶的酶水平和催化效率不同，这反过来表明不同个体可能更容易受到有机磷暴露的毒性影响。

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 OP exposure.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

福司哌酯是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强效的神经毒素，在低剂量时会导致过度流涎和流泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，后者在神经和肌肉接头处释放，以便让肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动不断传输，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计成与酶的活性位点结合。结构要求是一个带有两个亲脂性基团的磷原子、一个离去基团（如卤素或硫氰酸盐）以及一个末端的氧。

Fosthiazate 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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

急性接触胆碱酯酶抑制剂可能会导致胆碱能危象，表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力可能性增加，如果呼吸肌受到影响，可能会导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处尼古丁受体的过度刺激。当这种情况发生时，可以看到肌肉无力、疲劳、肌肉痉挛、肌束震颤和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中尼古丁受体的过度刺激。与此相关的症状包括高血压和低血糖。由于乙酰胆碱积累，中枢神经系统中尼古丁乙酰胆碱受体的过度刺激会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力，甚至可能昏迷。当由于乙酰胆碱过量在毒蕈碱乙酰胆碱受体上出现毒蕈碱过度刺激时，可能会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。对于男性和女性的生育、生长和发育，某些生殖效应与有机磷农药暴露有特异性关联。关于生殖效应的大多数研究都是在农村地区使用农药和杀虫剂的农民中进行的。在女性中，月经周期紊乱、怀孕时间延长、自然流产、死产以及后代的一些发育效应与有机磷农药暴露有关。产前暴露与胎儿生长和发育受损有关。神经毒性效应也与有机磷农药中毒有关，在人类中引起四种神经毒性效应：胆碱能综合症、中间综合症、有机磷诱导的迟发性多发性神经病（OPIDP）和慢性有机磷诱导的神经精神障碍（COPIND）。这些综合症在急性 and 慢性暴露于有机磷农药后出现。

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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

低剂量暴露的症状包括过度流涎和眼泪。急性剂量症状包括严重恶心/呕吐、流涎、出汗、心动过缓、低血压、虚脱和抽搐。肌肉无力可能会逐渐加剧，如果呼吸肌肉受影响，可能会导致死亡。还可能出现高血压、低血糖、焦虑、头痛、震颤和共济失调。

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露处理

如果已经摄入该化合物，应使用5%碳酸氢钠进行快速洗胃。对于皮肤接触，应用肥皂和水清洗皮肤。如果化合物进入眼睛，应用大量等渗盐水或水清洗。在严重情况下，应给予阿托品和/或普瑞洛辛。抗胆碱能药物作用是抵消过量的乙酰胆碱的作用并重新激活乙酰胆碱酯酶。阿托品可以与普瑞洛辛或其他吡啶季铵盐（如三甲氧胺或欧比多辛）联合使用作为解毒剂，尽管至少有两项荟萃分析发现使用“-氧胺”没有益处，甚至可能有害。阿托品是一种毒蕈碱拮抗剂，因此可以阻断乙酰胆碱在外周的作用。

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.

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

每组5只Crl:CD BR VAF/Plus大鼠，按性别分组，每天通过灌胃（用2 mL/kg玉米油溶剂）给予 fosthiazate 2 mg/kg，连续14天。然后给大鼠服用2 mg/kg标记的 fosthiazate，并在24小时或168小时后处死，此时收集组织（包括血液）进行放射性分析。在给药后间隔收集尿液、粪便和呼出空气。未标记的 fosthiazate 纯度为99%，环标记的 fosthiazate 纯度大于99%。预处理对代谢没有明显影响...随着时间的推移，排泄模式和组织残留物与单次给药处理相似。Fosthiazate 被迅速吸收、代谢和排泄。尿液是主要的排泄途径，而粪便和呼出空气是次要途径。在排泄途径或速率方面没有观察到性别差异。给药后24小时内排泄基本完成。在24小时时，75至82%的给药剂量被消除。在终止后168小时，分别有70%和13.2%的给药剂量通过尿液和粪便排出。大约5.3%以CO2的形式被消除。

Groups of 5 Crl:CD BR VAF/Plus rats/sex per group were dosed daily for 14 days by gavage (in 2 mL/kg corn oil vehicle) with fosthiazate at 2 mg/kg. Rats were then administered 2 mg/kg labeled fosthiazate, and were killed after 24 hrs or 168 hrs, at which time tissues (including blood) were collected for radiolabel analyses. Urine, feces, and expired air were collected at intervals after dosing. Unlabeled fosthiazate was 99% pure, and ring-labeled fosthiazate was >99% pure. There was no apparent effect of pre-treatment on metabolism... Patterns of excretion and tissue residues over time were comparable to single dose treatment. Fosthiazate is rapidly absorbed, metabolized, and excreted. Urine was the major route of excretion, whereas feces and expired air were minor routes. Neither sex-related differences in route or rate of excretion were observed. Excretion was essentially complete by 24 hrs after dosing. At 24 hrs, 75 to 82% of administered dose was eliminated. By 168 hrs after termination, 70% and 13.2% of administered dose was excreted in urine and feces, respectively. About 5.3% was eliminated as CO2.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

每组的5只Crl:CD BR VAF/Plus大鼠/性别通过灌胃(在2 mL/kg玉米油载体中)一次给药福司他唑，剂量为2或20 mg/kg。未标记的福司他唑纯度为99%，环标记的福司他唑纯度>99%。在整个7天的暴露后期间采集排泄物和呼出的空气。在终止时检查主要组织的标签。呼出的空气中含有5-6%的给药剂量(在1 N NaOH陷阱中，假定为CO2)，与性别或剂量水平无关。其中大部分在最初的12小时内收集。从CO2陷阱下游收集的挥发性有机物的量微不足道。尿液代谢物占男性给药剂量的66-67%，女性为71-73%。剂量水平之间没有明显差异。在所有情况下，超过一半的尿液标签在给药后6小时内收集。粪便代谢物占给药剂量的11-12%，与性别或剂量无关。大部分标签在48小时内收集。在2 mg/kg/天和20 mg/kg/天的雄性中，所有身体组织组合中发现的给药剂量总百分比分别为11.0和9.4%;分别为8.2和6.8%，表明有明显的保留。治疗1周后，组织标签广泛分布。在2 mg/kg时，标签的最高浓度在肝脏、肺和心脏。放射性物质显然没有集中在进入点(胃肠)或循环(血液)中，也没有集中在脂肪中。这种明显的组织保留，加上环成分代谢产生的标记碳的显著CO2产生，表明噻唑啉基环中的碳在很大程度上被同化到身体的碳池中。...

Groups of 5 Crl:CD BR VAF/Plus rats/sex per group were dosed once by gavage (in 2 mL/kg corn oil vehicle) with fosthiazate, either 2 or 20 mg/kg. Unlabeled fosthiazate was 99% pure, and ring-labeled fosthiazate was >99% pure. Excreta and exhaled air were sampled throughout the 7-day post-exposure period. Major tissues were examined at termination for label. Expired air contained 5-6% of administered dose (in 1 N NaOH traps, presumed to be CO2), regardless of sex or dose level. Most of this was collected in the first 12 hrs. Amounts of volatile organics collected downstream from the CO2 traps were minuscule. Urinary metabolites accounted for 66-67% of administered dose in males, and 71- 73% in females. There was no apparent difference between the dose levels. Over one-half of the urinary label was collected within 6 hrs of dosing in all cases. Fecal metabolites constituted 11-12% of administered dose, regardless of sex or dose. Most of this label was collected within 48 hrs. Total percentage of administered dose found in all body tissues combined were 11.0 and 9.4% in 2 mg/kg/day and 20 mg/kg/day males, respectively; and 8.2 and 6.8% in respective females, suggesting appreciable retention. Tissue label was widely distributed at 1 week post-treatment. Highest concentrations of label at 2 mg/kg were in liver, lung, and heart. Radioactivity was clearly not concentrated in points of entry (g.i. tract) or circulation (blood), nor in the fat. This appreciable tissue retention, coupled with the significant CO2 production of labeled carbon from metabolism of the ring component, suggests that carbon from the thiazolidinyl ring is substantially assimilated into the body's carbon pool. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

十只Crl:CD BR VAF/Plus大白鼠，按性别和组别，每天一次通过灌胃（用2 mL/kg玉米油溶剂）给予未标记的福司他唑ate，剂量为2 mg/kg/天。在第15天，大鼠给予2 mg/kg S-sec-butyl标记的福司他唑ate。在给药后24小时，每组各处死5只/性别带有标记的大鼠；另外5只/性别在7天后处死。...预处理的分布和排泄模式没有明显影响。在这项研究中，7天大鼠的标记物的命运占给药剂量的百分比是：尿液（雄性和雌性分别为73%和74%）、粪便（雄性和雌性分别为8%和9%）、呼出的二氧化碳（雄性和雌性分别为9%和8%）、呼出的挥发性有机物（雄性和雌性分别为0.5%和0.6%）、所有组织的总和（雄性和雌性分别为1.8%和1.2%）。...在处死当天，没有采样器官的特定放射性活度高于全血的2倍。在24小时处死时的组织采样（不包括胃肠道，因为标记的管腔内容物正常通过的时间不足）发现肝脏相对于全血的特定放射性活度最高（雄性肝脏/血液比值为4.4，雌性为2.3），其次是肺（雄性肺/血液比值为2.0，雌性为1.6），肾脏和肾上腺的特定浓度略低于肺，大多数器官或组织的标记浓度与全血相似或更低。...

Ten Crl:CD BR VAF/Plus rats/sex/group were dosed once daily by gavage (in 2 mL/kg corn oil vehicle) with unlabeled fosthiazate at 2 mg/kg/day. On Day 15, rats were administered 2 mg/kg S-sec-butyl-labeled fosthiazate. Five/sex were sacrificed at 24 hr after dosing with label: the other 5/sex were sacrificed after 7 days. ... There was no apparent effect of the pre-treatment on distribution and excretion patterns. Fate of label in the 7-day rats in this study in percent of administered dose was: urine (73 and 74% in M and F, respectively), feces (8 and 9% in M and F), expired air as CO2 (9 and 8% in M and F), expired air as volatile organics (0.5 and 0.6% in M and F), and all tissues combined (1.8 and 1.2% in M and F). ... no sampled organ had specific radioactivity higher than 2x that of whole blood at day 7 sacrifice. Tissue sampling at 24-hr sacrifice (excluding g.i. tract, due to insufficient time for normal passage of labeled lumenal contents) found liver to have the highest specific radioactivity relative to whole blood (liver/blood ratio 4.4 in M and 2.3 in F), followed by lung (lung/blood ratio 2.0 in M and 1.6 in F), with kidney and adrenal specific concentrations slightly lower than lung, and most organs or tissues similar to or lower label concentration than whole blood. ...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  T,N
• 安全说明：
  S25,S26,S39,S45,S53,S60,S61
• 危险类别码：
  R39,R21,R43,R50/53,R23/25,R41
• WGK Germany：
  3
• 海关编码：
  29341000
• 危险品运输编号：
  UN 2810
• RTECS号：
  TB1707000
• 包装等级：
  III
• 危险类别：
  6.1(b)

制备方法与用途

有机磷类杀线虫剂——噻唑磷

噻唑磷简介

噻唑磷是由日本石原产业公司开发的一种有机磷类杀线虫剂。其主要作用方式是抑制根结线虫乙酰胆碱酯酶的合成，具有强烈的触杀活性，并对传统杀虫剂已产生抗性的害虫也有很高的活性。

防治对象与应用

噻唑磷主要用于防治线虫、蚜虫等多种害虫，尤其适用于无公害蔬菜生产。它对根结线虫、根腐线虫、茎线虫和胞囊线虫等各种线虫都有很好的防效，并且具有良好的植物体传导作用，能防止侵入并对已侵入的线虫等有杀灭效果。

噻唑磷在一年生作物上的持效期为2～3个月，在多年生作物上则可达4～6个月。推荐用量为1.5～2公斤/亩，山东蔬菜区一般每季使用两次，每次施用4～6公斤，平均每季作物的生产成本约为200元。

噻唑磷在中国已取得了在黄瓜、番茄和西瓜上的登记，并可广泛应用于蔬菜、香蕉、果树、药材等作物。适用作物包括胡萝卜、茄子、萝卜、山药、马铃薯、大蒜、甘薯、西瓜、香蕉和烟草等。

毒性

噻唑磷对大鼠的急性经口LD₅₀值为57～73mg/kg，小鼠为91～104mg/kg；雄性大鼠的急性经皮LD₅₀值为2396mg/kg，雌性大鼠为861mg/kg。此外，噻唑磷对母鸡具有迟发神经毒性阴性，对兔眼睛有刺激性但无皮肤刺激性。对鲤鱼和水蚤的半数致死浓度分别为208mg/L（48小时）和2.17mg/L。

化学性质

噻唑磷为浅黄色液体，沸点为198℃/66.66Pa，蒸气压在25℃时为5.6×10⁻⁴Pa，在水中溶解度为9.85g/L（0.87%），分配系数为1.75。

用途

噻唑磷是一种杀虫剂和杀线虫剂，主要作用方式是抑制靶标害虫的乙酰胆碱酯酶，影响其神经系统功能。此外，它还可以用于防治多种作物上的线虫、蚜虫等害虫。

噻唑磷合成方法 正丁基锂法

将1.5g 2-氧代噻唑烷溶解于30mL四氢呋喃中，冷却后滴加正丁基锂的正己烷溶液（1.65mol），混合物搅拌15min。再向其中加入含有5g S-仲丁基-O-乙基硫代磷酰氯的10mL四氢呋喃溶液，并继续搅拌30min，于室温下反应3d后倒入水中，用乙酸乙酯提取、水洗、干燥、脱溶得2～3g所需产品。收率在70%～90%。

金属钠法

将甲苯和金属钠加入反应器中，在氮气保护下升温至回流温度。待金属钠熔融后，搅拌分散，滴加2-氧代噻唑烷的四氢呋喃溶液，继续反应2h。冷至15℃后，滴加S-仲丁基-O-乙基硫代磷酰氯，再反应1h。经后处理得噻唑硫磷纯度为96.4%，以磷酰氯计收率为91.2%。

反应信息

• 作为产物：
  描述：

  1,3-噻唑烷-2-酮 、 S-sec.-butyl-O-ethyl-thiophosphoric acid chloride 生成 噻唑磷
  参考文献：
  名称：

  XAGA, TAKAXIRO;DOKI, TADAAKI;KOYANAGI, TORU;OKADA, XIROSI;JOSIDA, KIEMITS+

  摘要：

  DOI：

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
  申请人：BASF SE

  公开号：WO2014206910A1

  公开（公告）日：2014-12-31

  The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及公式（I）中变量如索权和说明中所定义的自行车基取代异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包含所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] AZOLINE COMPOUNDS<br/>[FR] COMPOSÉS AZOLINE
  申请人：BASF SE

  公开号：WO2015128358A1

  公开（公告）日：2015-09-03

  The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式（I）的噁唑啉化合物，其中A、B1、B2、B3、G1、G2、X1、R1、R3a、R3b、Rg1和Rg2如权利要求和描述中所定义。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料、农业和兽医组合物。
• [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。
• [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。

表征谱图