兹克威 | 315-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 兹克威
• 中文别名: 自克威
• 英文名称: mexacarbate
• 英文别名: zectran；[4-(dimethylamino)-3,5-dimethylphenyl] N-methylcarbamate
• CAS: 315-18-4
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: YNEVBPNZHBAYOA-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  受热分解会产生有毒的氧化氮气体。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

标记有(14)C的CMPD在狗体内通过水解代谢为4-二甲氨基-3,5-二甲酚...4-二甲氨基组的脱甲基作用发生，...4-氨基组的位移，给出...2,6-二甲基对苯二酚。

THE CMPD LABELED WITH (14)C IS METABOLIZED IN DOGS BY HYDROLYSIS TO 4-DIMETHYLAMINO-3,5-XYLENOL ... DEMETHYLATION OF 4-DIMETHYLAMINO GROUP ... OCCURS, WITH DISPLACEMENT OF 4-AMINO GROUP TO GIVE ... 2,6-DIMETHYLHYDROQUINONE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

...暴露后...云杉食心虫和烟草食心虫的幼虫将Zectran转化为九种代谢物；家蝇幼虫产生了10种代谢物。在这三种昆虫中发现的四种代谢物被鉴定出来：4-甲基氨基、4-氨基、4-甲基甲酰胺和4-甲酰胺-3,5-二甲氧基苄基甲酸甲酯。

AFTER EXPOSURE ... LARVAE OF SPRUCE BUDWORM & TOBACCO BUDWORM CONVERTED ZECTRAN TO NINE METABOLITES; HOUSEFLY LARVAE PRODUCED 10 METABOLITES. FOUR OF THESE FOUND IN ALL THREE INSECTS WERE IDENTIFIED: 4-METHYLAMINO-, 4-AMINO-, 4-METHYLFORMAMIDO-, & 4-FORMAMIDO-3,5-XYLYL-METHYLCARBAMATES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... CMPD ... 被认为是N-羟甲基ZECTRAN /是由云杉和烟草芽虫以及家蝇幼虫在接触ZECTRAN后产生的。

... CMPD ... BELIEVED TO BE N-HYDROXYMETHYL ZECTRAN /WAS PRODUCED BY LARVAE OF SPRUCE & TOBACCO BUDWORMS & HOUSEFLY LARVAE AFTER EXPOSURE TO ZECTRAN/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... /在人肝脏培养后回收的四种代谢物是/ 4-甲基甲酰胺-3,5-二甲氧基苄基甲基碳酰胺, 4-氨基-3,5-二甲氧基苄基甲基碳酰胺, 4-甲基氨基-3,5-二甲氧基苄基甲基碳酰胺, 以及 4-二甲基氨基-3,5-二甲氧基-N-羟基甲基碳酰胺。还有一些 4-二甲基氨基-3,5-二甲氧基苯酚也存在。

... /FOUR METABOLITES RECOVERED AFTER INCUBATION WITH HUMAN LIVER ARE/ 4-METHYLFORMAMIDO-3,5-XYLYL METHYLCARBAMATE, 4-AMINO-3,5-XYLYL-METHYLCARBAMATE, 4-METHYLAMINO-3,5-XYLYL-METHYLCARBAMATE, & 4-DIMETHYLAMINO-3,5-XYLYL-N- HYDROXYMETHYLCARBAMATE. SOME 4-DIMETHYLAMINO-3,5-XYLENOL WAS ALSO PRESENT.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲酰胺通过肝脏酶促水解；降解产物由肾脏和肝脏排出。

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

美沙卡巴酯是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。碳酸酯通过与胆碱酯酶的活性位点进行碳酸化作用形成不稳定的复合物。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症状。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。

Mexacarbate 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

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

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：泽克特兰

IARC Carcinogenic Agent:Zectran

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第12卷：（1976年）一些氨基甲酸酯、硫代氨基甲酸酯和脒基脒

IARC Monographs:Volume 12: (1976) Some Carbamates, Thiocarbamates and Carbazides

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

ZECTRAN在一项实验中被喂给了狗，为期1周，使用的是标记有(14)C的环状物质。实验发现，排出的放射性物质中有3/4出现在尿液中，1/4在粪便中。在尿液中，大约86%的放射性物质以相应的酚的葡萄糖苷酸或硫酸盐形式存在，大约5%是氢醌，大约2%是未结合的酚。

ZECTRAN WAS FED TO DOGS FOR 1 WK USING (14)C RING-LABELED MATERIAL. 3/4 OF EXCRETED RADIOACTIVITY WAS FOUND IN URINE & 1/4 IN FECES, & IN URINE 86% OF IT WAS AS GLUCURONIDE OR SULFATE OF CORRESPONDING PHENOL WITH ABOUT 5% OF HYDROQUINONE & ABOUT 2% OF UNCONJUGATED PHENOL BEING FORMED.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当应用于西兰花时...对甲醇不溶物的检查表明Zectran已经结合到木质素中，它可能被永久储存。

WHEN APPLIED TO BROCCOLI ... EXAMINATION OF METHANOL INSOL MATERIAL INDICATED INCORPORATION OF ZECTRAN INTO THE LIGNIN WHERE IT PROBABLY IS PERMANENTLY STORED.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在狗身上，口服的ZECTRAN剂量主要以4-二甲氨基-3,5-二甲酚的形式在尿液中定量排出，主要是作为共轭物，以及2,6-二甲基对苯醌的共轭形式，还有小量的2,6-二甲基对苯醌。

IN DOGS, AN ORAL DOSE OF ZECTRAN WAS ELIMINATED QUANTITATIVELY IN THE URINE AS 4-DIMETHYLAMINO-3,5-XYLENOL, PREDOMINANTLY AS CONJUGATE, AS CONJUGATED FORMS OF 2,6-DIMETHYL HYDROQUINONE, & AS SMALL AMOUNTS OF 2,6-DIMETHYL-PARA-BENZOQUINONE.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

输注ZECTRAN...在大鼠中已经观察到胎盘转移；代谢物...也存在于胎儿中。

TRANSPLACENTAL TRANSFER OF ZECTRAN ... IN RATS HAS BEEN OBSERVED; METABOLITES ... WERE ALSO PRESENT IN THE FETUS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当用(14)C标记在羰基位置的Mexacarbate在孕期的第18或19天通过腹腔注射给大鼠时，大部分药物会非常迅速地分布和排泄。注射后15分钟，仅在合并的胎儿中发现了1.7%的放射性，8小时后这一比例降低到了0.8%。根据8小时内从尿液、粪便和呼出气体中回收的总放射性量来计算，孕鼠从Mexacarbate中保留的(14)C比非孕鼠多10.4至23%。

WHEN MEXACARBATE LABELED WITH (14)C IN THE CARBONYL POSITION WAS INJECTED IP INTO RATS ON THE 18TH OR 19TH DAY OF PREGNANCY, MOST OF IT WAS DISTRIBUTED & EXCRETED VERY RAPIDLY. AT 15 MINUTES AFTER INJECTION, ONLY 1.7% OF THE RADIOACTIVITY WAS FOUND IN THE POOLED FETUSES, & AFTER 8 HR THE PROPORTION HAD DECREASED TO 0.8%. BASED ON TOTAL RADIOACTIVITY RECOVERED FROM THE URINE, FECES, & EXHALED AIR DURING 8 HR, PREGNANT RATS RETAINED 10.4 TO 23% MORE (14)C FROM MEXACARBATE THAN DID NONPREGNANT ONES.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  库房应保持通风、低温和干燥，并与食品原料分开储运。

制备方法与用途

Mexacarbate is a carbamate pesticide developed by Alexander Shulgin.

反应信息

• 作为反应物：
  描述：

  兹克威 在 三乙胺 作用下， 以 N-甲基乙酰胺 、 乙醚 、 Petroleum ether 为溶剂， 生成 4-(dimethylamino)-3,5-xylyl [[(diethoxyphosphinothioyl)-n-propylamino]thio]methylcarbamate
  参考文献：
  名称：

  N-[(phosphinyl) amino]thio- and

  摘要：

  已合成并测试了一些新的磷酸酯类氨基硫代甲基氨基甲酸酯衍生物作为杀虫剂。这些新化合物对昆虫、螨和线虫具有活性。N-[(磷酰胺基)硫代]和N-[(磷硫酰基)胺基]硫代甲基氨基甲酸酯可通过一般程序制备，即将磷酸酯酰胺与二氯化硫反应，从而获得相应的N-(氯硫)磷酸酯酰胺，该反应物将与甲基氨基甲酸酯反应，从而产生本发明的相应化合物，即N-[(磷酰胺基)硫代]和N-[(磷硫酰基)胺基]硫代甲基氨基甲酸酯。还描述了用于杀虫剂使用的各种配方以及适当的施用速率。

  公开号：

  US04081536A1

文献信息

• [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。
• [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。
• Novel insecticides
  申请人：Syngenta Participations AG

  公开号：EP2540718A1

  公开（公告）日：2013-01-02

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

  式I的化合物 其中取代基如权利要求1所定义，并且式I化合物的农药可接受盐以及所有立体异构体和互变异构形式可用作杀虫剂，并且可以按照已知的方法制备。
• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。

表征谱图