仲草丹 | 36756-79-3

• 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: 仲草丹
• 英文名称: S-benzyl bis(1-methylpropyl)thiocarbamate
• 英文别名: tiocarbazil；S-benzyl di-sec-butylthiocarbamate；benzyl-N,N-di-sec. butyl-thiolcarbamate；benzyl N,N-di-sec.-butylthiolcarbamate；S-benzyl-N,N-disec-butylthiocarbamate；S-benzyl-di-sec-butyl-thiolcarbamate；S-benzyl N,N-di(butan-2-yl)carbamothioate
• CAS: 36756-79-3
• 化学式: C₁₆H₂₅NOS
• 分子量: 279.447
• InChiKey: PHSUVQBHRAWOQD-UHFFFAOYSA-N

物化性质

• 熔点：
  25°C
• 沸点：
  131 °C
• 密度：
  1.0443 (rough estimate)
• 溶解度：
  8.95e-06 M
• 保留指数：
  1984

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

一般来说，硫代氨基甲酸盐可以通过皮肤、粘膜以及呼吸和消化系统吸收。它们主要通过呼出气体和尿液迅速排出体外。哺乳动物中硫代氨基甲酸盐的代谢有两个主要途径。一个是通过亚磺酰化并与谷胱甘肽结合。结合产物随后裂解为半胱氨酸衍生物，该衍生物被代谢为巯基尿酸化合物。第二个途径是硫氧化为亚磺酰化物，然后进一步氧化为磺酰化物，或者经羟基化转变为进入碳代谢池的化合物。

As a general rule, thiocarbamates can be absorbed via the skin, mucous membranes, and the respiratory and gastrointestinal tracts. They are eliminated quite rapidly, mainly via expired air and urine. Two major pathways exist for the metabolism of thiocarbamates in mammals. One is via sulfoxidation and conjugation with glutathione. The conjugation product is then cleaved to a cysteine derivative, which is metabolized to a mercapturic acid compound. The second route is oxidation of the sulfur to a sulfoxide, which is then oxidized to a sulfone, or hydroxylation to compounds that enter the carbon metabolic pool.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

一些硫代氨基甲酸盐（EPTC、 Molinate、 Pebulate和Cycloate）具有共同的毒性机制，即抑制乙酰胆碱酯酶。乙酰胆碱酯酶抑制剂抑制乙酰胆碱酯酶的作用。由于乙酰胆碱酯酶具有基本功能，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。头痛、流涎、恶心、呕吐、腹痛和腹泻在高剂量暴露时常常很明显。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。

Some thiocarbamates (EPTC, Molinate, Pebulate, and Cycloate) share a common mechanism of toxicity, i.e. the inhibition of acetylcholinesterase. An acetylcholinesterase 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

关于硫代氨基甲酸酯对人的影响的数据很有限。然而，在农业工作者中观察到了刺激和致敏的案例。一些硫代氨基甲酸酯，例如 molinate，对精子形态有影响，从而影响繁殖。但是，没有观察到致畸效应。突变性研究的结果表明，含有二氯丙烯基团的硫代氨基甲酸酯具有高度突变性。一些硫代氨基甲酸酯是乙酰胆碱酯酶抑制剂。急性暴露于胆碱酯酶抑制剂可能导致胆碱能危象，其特征是严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力逐渐增加是一个可能性，如果涉及到呼吸肌，可能会导致死亡。

Data concerning the effects of thiocarbamates on man are scarce. However, cases of irritation and sensitization have been observed among agricultural workers. Some thiocarbamates, e.g., molinate, have an effect on sperm morphology and, consequently, on reproduction. However, no teratogenic effects have been observed. The results of mutagenicity studies have shown that thiocarbamates containing dichloroallyl groups are highly mutagenic. Some thiocarbamates are acetylcholine esterase inhibitors. 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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L793）；口服（L793）；皮肤给药（L793）

Inhalation (L793) ; oral (L793); dermal (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

与有机磷化合物一样，症状和体征基于过度的胆碱能刺激。与有机磷中毒不同，氨基甲酸酯中毒的持续时间往往较短，因为神经组织乙酰胆碱酯酶的抑制作用是可逆的，且氨基甲酸酯的代谢速度更快。肌肉无力、眩晕、出汗和轻微的身体不适是常见的早期症状。头痛、流涎、恶心、呕吐、腹痛和腹泻在较高暴露水平时常常更为明显。瞳孔收缩伴视力模糊、不协调、肌肉抽搐和言语不清也有报道。(L795)

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2930200014

反应信息

• 作为产物：
  描述：

  二仲丁胺 、 benzyl chlorothioformate 在 sodium hydroxide 作用下， 以 1,1-二氯乙烷 、 水 、 1,2-二氯乙烷 为溶剂， 生成 仲草丹
  参考文献：
  名称：

  S-benzyl-N,N-disec-butylthiocarbamate and its use as a rice field

  摘要：

  S-苄基-N，N-二正丁硫代氨基甲酸酯，一种新化合物，具有既是高效稻田除草剂又是促进稻米生长的独特性能组合。

  公开号：

  US03930838A1

文献信息

• [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。
• [EN] HERBICIDALLY ACTIVE HETEROARYL-S?BSTIT?TED CYCLIC DIONES OR DERIVATIVES THEREOF<br/>[FR] DIONES CYCLIQUES SUBSTITUÉES PAR HÉTÉROARYLE À ACTIVITÉ HERBICIDE OU DÉRIVÉS DE CELLES-CI
  申请人：SYNGENTA LTD

  公开号：WO2011012862A1

  公开（公告）日：2011-02-03

  The invention relates to a compound of formula (I), which is suitable for use as a herbicide wherein G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; Q is a unsubstituted or substituted C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, or Q is heteroaryl or substituted heteroaryl; m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; and wherein the compound is optionally an agronomically acceptable salt thereof.

  该发明涉及一种化合物，其化学式为(I)，适用作为除草剂，其中G为氢或农业可接受的金属、磺酸盐、铵盐或潜伏基团；Q为未取代或取代的含有至少一个来自O、N和S的杂原子的饱和或单不饱和的C3-C8杂环烷基，或Q为杂芳基或取代的杂芳基；m为1、2或3；Het为可选择地取代的单环或双环杂芳环；且该化合物可选择地为其农学上可接受的盐。
• 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。
• [EN] NOVEL HERBICIDES<br/>[FR] NOUVEAUX HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2009015877A1

  公开（公告）日：2009-02-05

  Bicyclic dione compounds, and derivatives thereof, which are suitable for use as herbicides. formula (I)

  双环二酮化合物及其衍生物，适用于用作除草剂。公式（I）
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  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 aga inst 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有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂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化学式（“化学式一”）的分子。