aldicarb | 61602-66-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: aldicarb
• 英文别名: 2-Methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime；Temik；2-methyl-2-(methylthio)propanal O-[(methylamino)carbonyl]oxime；2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime；[(E)-(2-methyl-2-methylsulfanylpropylidene)amino] N-methylcarbamate
• CAS: 61602-66-2
• 化学式: C₇H₁₄N₂O₂S
• 分子量: 190.266
• InChiKey: QGLZXHRNAYXIBU-WEVVVXLNSA-N

物化性质

• 密度：
  1.08±0.1 g/cm3(Predicted)
• 物理描述：
  Aldicarb appears as white crystals with a slightly sulfurous odor. Commercial formulations are granular Used as an insecticide, acaricide, and nematocide. (EPA, 1998)
• 颜色/状态：
  Crystals from isopropyl ether
• 气味：
  Slightly sulfurous odor
• 沸点：
  Decomposes (NTP, 1992)
• 熔点：
  99.0 °C
• 溶解度：
  350 g/kg, acetone; 300 g/kg, dichloromethane; 150 g/kg, benzene; 150 g/kg, xylene; all at 25 °C
• 蒸汽压力：
  2.9X10-5 mm Hg at 20 °C
• 稳定性/保质期：
  Aldicarb is stable under normal storage conditions and in acidic media but decomposes rapidly in alkaline media and at temperatures above 100 °C.
• 分解：
  ... Decomposes rapidly in alkaline media & at temperatures above 100 °C.
• 腐蚀性：
  Non-corrosive to common metals and plastics

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

在给予羰基-(14)C标记的丁硫克百威后48小时内，大鼠通过呼出超过60%的(14)C作为二氧化碳，尿液中发现的不到30%。在其他(14)C研究中，大鼠通过尿液排出了超过80%的降解产物，通过粪便排出的不到10%（这种排泄模式有利于葡萄糖苷酸的内脏-肝脏循环，这也可以帮助延长有毒代谢物的系统活性）。主要的尿液代谢物是丁硫克百威亚砜（剂量的40%），其肟和腈形式（超过30%）；亚砜和相关的肟和腈；以及，醛和酸类似物。丁硫克百威在排泄物中不常见。摄入植物组织的结合残留物未被吸收，因此可以在粪便中找到。在单次剂量和短期饮食研究中，哺乳期奶牛以与大鼠相同的速度并以相同的代谢物阵列排出了丁硫克百威代谢物。大约1%的剂量通过牛奶排出，亚砜和亚砜分别是总牛奶残留含量的15%和4%的主要代谢物。

Within 48 hours of administration of carbonyl-(14)C labelled aldicarb rats eliminated over 60% of the (14)C as carbon dioxide, less than 30% was found in the urine. In other (14)C-studies rats excreted more than 80% of the degradation products in urine and less than 10% in faeces (an excretion pattern favoured by enterohepatic cycling of glucuronides which may also serve to extend the systemic activity of the toxic metabolites). The major urinary metabolites were aldicarb sulfoxide (40% of the dose), its oxime and nitrile forms (over 30%); the sulfone and related oxime and nitrile; and, the aldehyde and acid analogues. Aldicarb is not commonly found in the excreta. Bound residues of ingested plant tissues are not absorbed and therefore are found in the faeces. In single dose and short-term diet studies, lactating cows eliminated aldicarb metabolites as rapidly as rats and in the same array of metabolites. Approximately 1% of the dose was excreted in the milk, sulfone and sulfoxide were the major metabolites at 15 and 4% of the total milk residue content respectively.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... Aldicarb 通过氧化途径和水解过程进行代谢。氧化产生具有活性的胆碱酯酶抑制剂，而水解产生的化合物对昆虫的活性或对其他生物的毒性很小或没有。

... Aldicarb is metabolized by both oxidative pathways and hydrolytic processes. Oxidation results in cmpd which are also active cholinesterase inhibitors, while hydrolysis produces cmpd of little or no insecticidal activity or toxicity to other organisms.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Temik-(35)S/aldicarb/的主要消除途径是通过尿液。在牛奶中提取并初步鉴定出11种化合物，包括Temik亚砜和砜、氧肟酸亚砜和砜、腈亚砜和砜、Temik氧肟酸以及4种未识别的化合物。尿液中鉴定的代谢物在质量上相同，但在数量上有所不同。粪便中仅鉴定出5种代谢物：Temik氧肟酸、氧肟酸亚砜、Temik亚砜、Temik砜和腈砜。

The major route of elimination of Temik-(35)S /aldicarb/ ... admin to lactating cow was by way of urine. Extracted and tentatively identified in milk were 11 compounds, incl temik sulfoxide and sulfone, oxime sulfoxide and sulfone, nitrile sulfoxide & sulfone, temik oxime, and 4 unidentified compounds. Metabolites identified in urine were qualitatively identical but differed quantitatively. Only 5 metabolites were identified in feces: temik oxime, oxime sulfoxide, temik sulfoxide, temik sulfone and nitrile sulfone.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中，亚砜占剂量的40%，磺酰酮占1%；这两种代谢物都比涕灭威具有更强的抗胆碱酯酶活性。牛乳和尿液中的代谢物是磺酰酮的羟甲基类似物；另外两种牛代谢物是2-甲基-2-(甲基亚磺酰基)丙醇和2-甲基-2-(甲基磺酰基)丙醇。

In rats, sulfoxide accounted for 40% of dose /of aldicarb/ and sulfone for 1%; both ... are more potent anticholinesterases than aldicarb. Metabolite in cow's milk and urine was hydroxymethyl analogue of sulfone; two other bovine metabolites were 2-methyl-2-(methylsulfinyl)propanol and 2-methyl-2-(methylsulfonyl)propanol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氨基甲酸酯通过肝脏酶促水解；降解产物通过肾脏和肝脏排出。

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

识别： Aldicarb 是一种氨基甲酸酯类杀虫剂。它是一种白色结晶固体，水中溶解度适中，容易发生氧化和水解反应。人类暴露：普通人群暴露于 Aldicarb 及其有毒代谢物（亚砜和砜）主要是通过食物。摄入受污染的食物导致了 Aldicarb 及其有毒代谢物（亚砜和砜）的中毒事件。由于 Aldicarb 具有高度的急性毒性，如果在职业暴露条件下预防措施不足，吸入和皮肤接触可能对工人造成危险。由于使用不当或缺乏保护措施，工人意外暴露的事件时有发生。Aldicarb 能有效地从胃肠道吸收，较少程度上通过皮肤吸收。如果有尘埃存在，它可能会被呼吸道轻易吸收。它通过代谢转化为亚砜和砜（两者均有毒），并通过水解转化为腈和硝基化合物以解毒。Aldicarb 及其代谢物的排泄迅速，主要通过尿液进行。一小部分也会通过胆汁排出，从而进行肠肝循环。长期暴露不会导致 Aldicarb 在体内积累。Aldicarb 对乙酰胆碱酯酶活性的抑制作用在体外是可逆的，半衰期为 30-40 分钟。在人类中，Aldicarb 唯一公认的效果是在神经突触和神经肌肉接头处抑制乙酰胆碱酯酶，这与有机磷化合物的作用相似。碳酰胺化的酶不稳定，与磷酸化的酶相比，自发性再活化相对较快。人类非致命性中毒是迅速可逆的。恢复可通过阿托品治疗得到帮助。动物研究：Aldicarb 是一种强效的乙酰胆碱酯酶抑制剂，具有高度的急性毒性。除非导致死亡，否则在 6 小时内其胆碱能效应会自发并完全恢复。没有实质性证据表明 Aldicarb 具有致畸性、致突变性、致癌性或免疫毒性。由于摄入未完全按推荐方式掺入土壤的 Aldicarb 颗粒，鸟类和小型哺乳动物已被杀死。在实验室测试中，Aldicarb 对水生生物具有急性毒性。

IDENTIFICATION: Aldicarb is a carbamate ester pesticide. It is a white crystalline solid, moderately soluble in water, and susceptible to oxidation and hydrolytic reactions. HUMAN EXPOSURE: Exposure of the general population to aldicarb and its toxic metabolites (the sulfoxide and sulfone) occurs mainly through food. The ingestion of contaminated food has led to poisoning incidents from aldicarb and its toxic metabolites (the sulfoxide and sulfone). Due to the high acute toxicity of aldicarb, both inhalation and skin contact under occupational exposure conditions may be dangerous for workers if preventive measures are inadequate. There have been a few incidents of accidental exposure of workers due to improper use or lack of protective measures. Aldicarb is efficiently absorbed from the gastrointestinal tract and, to a lesser extent, through the skin. It could be readily absorbed by the respiratory tract if dust were present. It is metabolically transformed to the sulfoxide and the sulfone (both of which are toxic), and is detoxified by hydrolysis to oximes and nitriles. The excretion of aldicarb and its metabolites is rapid and primarily via the urine. A minor part is also subject to biliary elimination and, consequently, to enterohepatic recycling. Aldicarb does not accumulate in the body as a result of long-term exposure. The inhibition of cholinesterase activity in vitro by aldicarb is spontaneously reversible, the half-life being 30-40 min. The inhibition of acetylcholinesterase at the nervous synapse and myoneural junction is the only recognized effect of aldicarb in humans and is similar to the action of organophosphates. The carbamyolated enzyme is unstable, and spontaneous reactivation is relatively rapid compared with that of a phosphorylated enzyme. Non-fatal poisoning in man is rapidly reversible. Recovery is aided by the administration of atropine. ANIMAL STUDIES: Aldicarb is a potent inhibitor of cholinesterases and has a high acute toxicity. Recovery from its cholinergic effects is spontaneous and complete within 6 hr, unless death results. There is no substantial evidence to indicate that aldicarb is teratogenic, mutagenic, carcinogenic, or immunotoxic. Birds and small mammals have been killed as a result of ingesting aldicarb granules not fully incorporated into the soil as recommended. In laboratory tests, aldicarb is acutely toxic to aquatic organisms.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

Aldicarb 是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。碳酰胺通过与酶的活性位点进行碳酰胺化，形成不稳定的复合物与胆碱酯酶。这种抑制作用是可逆的。胆碱酯酶抑制剂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，即使在低剂量下也会导致过度流涎和流泪。在更高剂量的暴露下，头痛、流涎、恶心、呕吐、腹痛和腹泻通常是显著的表现。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，使得任何神经冲动持续传递，肌肉收缩不会停止。

Aldicarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. 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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

评估：没有来自人类研究的可用数据。实验动物中关于涕灭威致癌性的证据不足。总体评估：涕灭威的致癌性无法归类为对人类有致癌性（第3组）。

Evaluation: No data were available from studies in humans. There is inadequate evidence for the carcinogenicity of aldicarb in experimental animals. Overall evaluation: Aldicarb is not classifiable as to its carcinogenicity to humans (Group 3).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：E组 人类非致癌性证据

Cancer Classification: Group E Evidence of Non-carcinogenicity for Humans

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：在喂养研究中，没有发现aldoarb在大小鼠中诱导统计学上显著增加肿瘤发生率，在小鼠的皮肤涂抹研究中也未发现。然而，在喂养研究中，雌性大鼠的垂体肿瘤和雄性小鼠的纤维肉瘤有显著的趋势。这一证据，加上使用的剂量低于最大耐受剂量的事实，表明现有的检测方法不足以评估aldoarb的致癌潜力。人类致癌性数据：无。动物致癌性数据：不充分。/基于先前的分类系统/

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Aldicarb was not found to induce statistically significant increases in tumor incidence in mice or rats in feeding studies or mice in a skin painting study. In the feeding studies there were, however, significant trends in pituitary tumors in female rats and fibrosarcomas in the male mouse. This evidence, together with the fact that less than maximum tolerated doses were used, indictes that the available assays are inadequate to assess the carcinogenic potential of aldicarb. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Inadequate. /Based on former classification system/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

雄性大鼠（Carworth Farms-Elias Stock）通过口服或腹腔注射的方式接受了标记的Temik溶于乙醇或Temik亚砜溶于水的处理。S-甲基-(14)C和叔丁基-(14)C temik的排泄在4天内基本完成。N-甲基-(14)C在尿液和粪便中排泄长达11天。

Male rats (Carworth Farms-Elias Stock) were treated orally or ip with labeled Temik in ethanol or Temik sulfoxide in water. Excretion of s-methyl-(14)C & tert-butyl-(14)C temik was completed, essentially, in 4 days. N-methyl-(14)C was excreted in urine & feces up to 11 days.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

阿德卡普从处理过的动物的消化道中被迅速吸收。给大鼠施用放射性标记化合物的排泄主要在尿液中，大约80%在24小时内出现，另外1%在粪便中。在排泄物中只发现了微量的未改变母体化合物。当阿德卡普在N-甲基碳或羰基碳上标记时，很大一部分放射性物质以(14)CO2的形式在呼出的空气中找到。在处理过的动物的组织或尸体中，发现的阿德卡普残留物非常少。

Aldicarb is readily absorbed from GI tract of treated animals. Excretion of radiolabeled cmpd admin to rats is primarily in urine, as approx 80% appears within 24 hr, with additional 1% in feces. Only traces of unchanged parent cmpd were found in excreta. When aldicarb is labeled on n-methyl carbon or carbonyl carbon large portion of radioactivity is found in expired air as (14)CO2. Very little aldicarb residues are found in tissues or carcasses of treated animals.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

为了测量aldicarb的排泄量，实验犬在给药前20天和给药后10天分别维持摄入0.75毫克/犬/日的饮食，并给予单次(14)C标记的aldicarb剂量。在尿液中回收的放射性物质中，有90%在给药放射性标记aldicarb后24小时内发现。

To measure the excretion of aldicarb admin repeatedly, dogs were maintained on diets determining an intake of 0.75 mg/dog/day for 20 days before & 10 days after being given a single (14)C-labeled dose. Of the radioactivity recovered in the urine, 90% was found within 24 hr after admin of the radiolabeled aldicarb.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Aldicarb在大鼠和牛中通过肠道容易被吸收，在大鼠和家兔中通过皮肤吸收。它被迅速代谢并在接触后24小时内排出体外，几乎所有有毒和无毒的代谢物都通过尿液排出。

Aldicarb is readily absorbed through the gut in rats and cows and through the skin in rats and rabbits. It is rapidly metabolized and excreted within 24 hours of exposure, almost all of the toxic and nontoxic metabolites being excreted in urine.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  aldicarb 在 甲酸 、 硫酸 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-methyl-2-(methylsulfonyl)propionaldehyde O-(methylcarbamoyl)oxime
  参考文献：
  名称：

  Preparation of organic sulfone compounds

  摘要：

  一种原位制备有机砜化合物的过程，通过在存在少量矿酸或有机砜酸的催化作用下，将相应的硫醚化合物与过氧化氢、羧酸的混合物氧化。

  公开号：

  US04097526A1
• 作为产物：
  描述：

  2-氯-2-甲基丙醛 生成 aldicarb
  参考文献：
  名称：

  GHEORGHE, S. M.;BARBULESCU, N.;BRAD, E.;POPA, C.;SINTAMARIAN, A.;PETCU, M+

  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。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。

表征谱图