[(Z)-(2-methyl-2-methylsulfanylpropylidene)amino] N-methylcarbamate | 116-06-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(Z)-(2-methyl-2-methylsulfanylpropylidene)amino] N-methylcarbamate
• CAS: 116-06-3
• 化学式: CH₃SC(CH₃)₂CH=NOCONHCH₃
• 分子量: 190.27
• InChiKey: QGLZXHRNAYXIBU-UITAMQMPSA-N

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组合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被代谢。氧化产生具有活性的胆碱酯酶抑制剂的化合物，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)

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，容易被氧化和水解反应。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 的高急性毒性，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，工人发生了几起意外暴露事件。Aldicarb 可从胃肠道高效吸收，皮肤吸收程度较低。如果存在粉尘，它可以通过呼吸道轻易吸收。它通过代谢转化为亚砜和砜（两者均有毒），并通过水解转化为羟胺和腈来解毒。Aldicarb 及其代谢物的排泄迅速，主要途径为尿液。还有一小部分通过胆汁排出，因此会进行肠肝循环。长期暴露后，Aldicarb 不会在体内积聚。Aldicarb 在体外对胆碱酯酶活性的抑制是自发可逆的，半衰期为 30-40 分钟。在神经突触和神经肌肉接头抑制乙酰胆碱酯酶是 Aldicarb 在人类中唯一公认的效应，与有机磷的作用相似。碳酰胺化酶不稳定，与磷酸化酶相比，自发再活化相对较快。人类非致命性中毒迅速可逆。恢复可通过阿托品治疗得到帮助。动物研究：Aldicarb 是一种强效的胆碱酯酶抑制剂，具有高急性毒性。除非死亡，否则在 6 小时内其胆碱能效应的恢复是自发和完全的。没有充分的证据表明 Aldicarb 是致畸、致突变、致癌或免疫毒性的。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

• 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)

毒理性

• 致癌物分类

国际癌症研究机构致癌物： Aldicarb（涕灭威）

IARC Carcinogenic Agent:Aldicarb

来源:International Agency for Research on Cancer (IARC)

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，几乎找不到阿德卡普的残留物。

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)

文献信息

• New oxazolinone compounds useful as intermediates for the preparation of insecticidal and acaracidal cinnamide compounds
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0274546A1

  公开（公告）日：1988-07-20

  The present invention relates to novel cinna­mamide compounds and oxazolinone compounds and processes for the preparation thereof. The compounds of the invention are useful for controlling insects and acarina and the oxazolinone also are useful intermediates in the prepa­ration of the cinnamamide insecticides and acaricides.

  本发明涉及新型肉桂酰胺化合物和噁唑烷酮化合物以及其制备方法。该发明的化合物对控制昆虫和螨虫具有用途，而噁唑烷酮也是肉桂酰胺类杀虫剂和螨虫剂的制备中间体。
• Novel insecticidal diacylhydrazine compounds
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0228564A2

  公开（公告）日：1987-07-15

  The present invention relates to unsubstituted di­acylhydrazine compounds and novel substituted diacylhy­drazine compounds useful as insecticidal agents. These diacylhydrazines control insect populations and protect agronomic crops, trees, shrubs and ornamentals, both while growing and after harvesting, from insect attack. Novel substituted benzoic acid 1 and 2-alkyl and 2-cycloalkylhydrazides effective as insecticides or inter­mediates for the preparation of insecticidal diacylhydra­zides also are presented.

  本发明涉及可用作杀虫剂的未取代二酰肼化合物和新型取代二酰肼化合物。 这些二酰肼可控制昆虫数量，保护农作物、树木、灌木和观赏植物在生长过程中和收获后免受昆虫侵害。 本发明还涉及可用作杀虫剂或制备杀虫二酰肼中间体的新型取代苯甲酸 1 和 2-烷基和 2-环烷基肼。
• Process for preparing ureas
  申请人：DOWELANCO

  公开号：EP0296864A2

  公开（公告）日：1988-12-28

  The present invention provides a novel process for preparing herbicidal and insecticidal ureas, carbamates and carbamate derivatives of the formula     E is -O- or -C(R⁴)₂- ;     R is C₁-C₇ alkyl;     R¹ is H, C₁-C₇ alkyl, C₃-C₇ cycloalkyl, phenyl, or C₁-C₄ alkylphenyl;     R² is H, C₁-C₇ alkyl, C₃-C₇ cycloalkyl, C₂-C₇ alkenyl, C₂-C₇ alkynyl, or phenyl optionally substituted with Cl, Br, -NO₂, -CF₃, C₁-C₄ alkyl, C₁-C₄ alkoxy, or -N(C₁-C₄ alkyl)₂;     R³ is H, F, Cl, Br, -CF₃, C₁-C₇ alkyl option­ally substituted with F, Cl, or Br, -S(O)n C₁-C₇ alkyl, C₁-C₇ alkoxy, C₃-C₇ cycloalkyl optionally substituted with F, Cl, or Br, or phenyl optionally substituted with F, Cl, Br, -NO₂, -CF₃, or C₁-C₄ alkyl;     R⁴ is H or C₁-C₄ alkyl;     R⁵ is C₁-C₇ alkoxy or -S(O)n C₁-C₇ alkyl;     R⁶ is C₁-C₅ alkyl optionally substituted with F, Cl, or Br, C₃-C₅ cycloalkyl, phenyl, or --N(C₁-C₄ alkyl)₂;     X is R³, -N=CH-N(C₁-C₄ alkyl)₂, -N(C₁-C₄ alkyl)₂ or -N(C₂-C₄ alkenyl)₂,     Y is H or S(O)n C₁-C₇ alkyl;     Z is H, C₁-C₄ alkyl, Cl, F, Br, haloalkyl, -NO₂, -N(C₁-C₄ alkyl)₂, -C≡N, phenyl, -S(C₁-C₄ alkyl), or C₁-C₄ alkoxy;     n is 0, 1, or 2; and     m is 1, 2 or 3, comprising reacting a nucleophile of the formula A-H, wherein A is as defined above, with a urea of the formula wherein each R is independently chosen from R as set forth above and each R¹ is independently chosen from R¹ as set forth above.

  本发明提供了一种制备除草和杀虫脲、氨基甲酸酯和氨基甲酸酯衍生物的新工艺，其式为 E是-O-或-C(R⁴)₂- ； R 是 C₁-C₇ 烷基； R¹ 是 H、C₁-C₇ 烷基、C₃-C₇ 环烷基、苯基或 C₁-C₄ 烷基苯基； R² 是 H、C₁-C₇ 烷基、C₃-C₇ 环烷基、C₂-C₇ 烯基、C₂-C₇ 炔基或任选被 Cl、Br、-NO₂、-CF₃、C₁-C₄ 烷基、C₁-C₄ 烷氧基或 -N(C₁-C₄ 烷基)₂ 取代的苯基； R³ 是 H、F、Cl、Br、-CF₃、任选被 F、Cl 或 Br 取代的 C₁-C₇ 烷基、-S(O)n C₁-C₇ 烷基、C₁-C₇ 烷氧基、任选被 F、Cl 或 Br 取代的 C₃-C₇ 环烷基，或任选被 F、Cl、Br、-NO₂、-CF₃ 或 C₁-C₄ 烷基取代的苯基； R⁴ 是 H 或 C₁-C₄ 烷基； R⁵ 是 C₁-C₇ 烷氧基或 -S(O)n C₁-C₇ 烷基； R⁶ 是任选被 F、Cl 或 Br 取代的 C₁-C₅ 烷基、C₃-C₅ 环烷基、苯基，或 --N(C₁-C₄烷基)₂； X 是 R³、-N=CH-N(C₁-C₄ 烷基)₂、 -N(C₁-C₄烷基)₂或-N(C₂-C₄烯基)₂、 Y 是 H 或 S(O)n C₁-C₇ 烷基； Z 是 H、C₁-C₄ 烷基、Cl、F、Br、卤代烷基、-NO₂、-N(C₁-C₄ 烷基)₂、-C≡N、苯基、-S(C₁-C₄ 烷基)或 C₁-C₄ 烷氧基； n 是 0、1 或 2；以及 m 是 1、2 或 3、 包括使式 A-H（其中 A 如上文所定义）的亲核剂与式中的脲反应 其中每个 R 独立地选自上述 R，每个 R¹ 独立地选自上述 R¹。
• Agricultural foam compositions
  申请人：PFIZER INC.

  公开号：EP0400914A1

  公开（公告）日：1990-12-05

  The present invention is directed to agricultural chemicals dispersed in an aqueous foam composition wherein the foam composition comprises a polysaccharide or synthetic polymer, a surfactant and an aqueous medium. Also disclosed are processes for seed treatment.

  本发明涉及分散在水性泡沫组合物中的农用化学品，其中泡沫组合物包括多糖或合成聚合物、表面活性剂和水性介质。本发明还公开了种子处理工艺。
• Amidothiophosphate derivative and insecticide, nematocide and acaricide containing the same as active ingredient
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0638576A1

  公开（公告）日：1995-02-15

  The present invention relates to amidothiophosphate derivatives represented by the formula II: in which R₁ is a methyl group or an ethyl group; R₂ is a n-propyl group or a sec-butyl group; R₃ is a C₁-C₄ alkoxy group, a C₁-C₄ alkylthio group, phenyl group or a phenoxy group; and n represents 1 or 2, and an insecticide, a nematocide and an acaricide containing the same as an active ingredient.

  本发明涉及式 II 所代表的脒基硫代磷酸酯衍生物： 其中 R₁ 是甲基或乙基； R₂ 是一个正丙基或一个仲丁基； R₃ 是 C₁-C₄ 烷氧基、C₁-C₄ 烷硫基、苯基或苯氧基；以及 n 代表 1 或 2，以及含有相同活性成分的杀虫剂、杀线虫剂和杀螨剂。