环草隆 | 1982-49-6

• 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: 环草隆
• 中文别名: 1-(2-甲基环己基)-3-苯基脲；1-(2-甲基环己基)-3-苯基脲；H1318
• 英文名称: Siduron
• 英文别名: N-(2-Methylcyclohexyl)-N'-phenyl-urea；1-(2-methylcyclohexyl)-3-phenylurea
• CAS: 1982-49-6
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: JXVIIQLNUPXOII-UHFFFAOYSA-N

物化性质

• 熔点：
  135.5℃
• 沸点：
  374.49°C (rough estimate)
• 密度：
  1.0151 (rough estimate)
• 颜色/状态：
  White crystals
• 气味：
  Odorless
• 溶解度：
  In dimethylacetamide 36.7, dimethylformamide 26, ethanol 16, isophorone 11.8, cellosolve 17.5, and methylene chloride 11.8 (all in g/100 mL) at 25 °C.
• 蒸汽压力：
  4.0X10-9 mm Hg at 25 °C
• 稳定性/保质期：
  It is stable up to its MP and in water at neutral pH, but is slowly decomp in acid and alkaline media
• 腐蚀性：
  Noncorrosive
• 保留指数：
  2123.4

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

ADMET

代谢

从接受2500 ppm 赛杜隆饮食的狗身上收集的尿液中，使用比色法、质谱、红外光谱和核磁共振光谱分析了母体化合物和代谢物，并提出了代谢途径；没有找到母体化合物，但分离并鉴定了三种羟基取代赛杜隆的葡萄糖苷酸结合物，一种在苯环上取代，一种在环己基环上取代，另一种在这两个位置上都取代；似乎赛杜隆首先在任一位置羟基化，然后这两个单羟基化合物再次羟基化形成1-(4-羟基-2-甲基环己基)-3-对羟基苯基脲；将狗的尿液与接受相似2500 ppm饮食的大鼠的尿液进行比较，发现大鼠形成的环己基取代化合物比狗略少；这两种动物尿液中结合的总赛杜隆代谢物为800-1000 ppm。

Urine from a dog receiving 2500 ppm siduron in the diet was collected and analyzed for the parent compound and metabolites using a colorimetric method, and mass, IR, and NMR spectrometry, and a metabolic pathway was proposed; none of the parent compound was found, but three glucuronide conjugates of hydroxysubstituted siduron were isolated and identified, one substituted on the phenyl ring, one substituted on the cyclohexyl ring, and another substituted in both locations; it appears that siduron is first hydroxylated at either location, then both of these mono-hydroxylated compounds are hydroxylated again to form 1-(4-hydroxy-2-methylcyclo-hexyl)-3-p-hydroxyphenylurea; comparison of urine from the dog with that from a rat on a similar 2500 ppm diet, showed that the rat formed slightly less of the cyclohexyl-substituted compound than the dog; 800-1000 ppm of total siduron metabolites was bound in the urine of these two animals.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在使用(14)C标记的西杜隆的研究中，大麦植株在8天的吸收期后没有检测到代谢物。

In studies with (14)C-labeled siduron, no metabolites ... were detectable in barley plants after an 8 day absorption period.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 在狗身上，苯基和环己基环都会发生羟基化。... 提出的途径... 表明赛杜隆要么在苯基核的对位上羟基化，要么在2-甲基环己基部分的4位上羟基化。两种代谢物都会进一步羟基化，形成1-(4-羟基-2-甲基环己基)-3-(对-羟基苯基)脲。

... Both phenyl and cyclohexyl rings are subjected to hydroxylation in the dog. ... The pathways proposed ... show that siduron is either hydroxylated at para position of phenyl nucleus or at 4 position of 2-methylcyclohexyl moiety. Both metabolites are further hydroxylated to form 1-(4-hydroxy-2-methylcyclohexyl)-3-(p-hydroxyphenyl)urea.

来源:Hazardous Substances Data Bank (HSDB)

代谢

当对狗和老鼠的尿液样本进行水解并分析氨基酚和对位的氨基时，观察到在大鼠中苯基的羟基化比狗更为显著。显然，大鼠在羟基化苯脲的芳香核方面表现出特有的效率。在另一项研究中，应用了(14)C-羰基标记化合物……微生物降解是土壤中赛杜松消失的主要途径。在薄层板上分离出的代谢物与尿液中确定的代谢物具有相同的特征，并且……得出结论，环羟基化在土壤环境中也是有效的。

When urine samples of both dogs and rats were subjected to hydrolysis and analyzed for aminophenol /as well as/ aniline, it was observed that hydroxylation of the phenyl moiety was more prominent in the rat than in dog. Apparently rats exhibit particular efficiency in hydroxylating the aromatic nucleus of phenylureas. In another study in which (14)C- carbonyl-labeled compound was applied ... microbial degradation was major route of siduron disappearance in soil. Metabolites separated on thin-layer plates had same characteristics as those identified in urine, and /it was/ ... concluded that ring hydroxylation was also operative in soil environment.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为次要的毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

皮肤污染应立即用肥皂和水清洗处理。眼睛污染应立即用大量清水长时间冲洗眼睛。如果皮肤或眼睛刺激持续存在，应立即获取医疗注意。/其他除草剂/

Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other Herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

活性炭可能有效地限制刺激作用并减少对这些除草剂中大多数或全部的吸收。/其他除草剂/

Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. /Other herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

如果出现严重的脱水和电解质流失，由于呕吐和腹泻，监测血液电解质和液体平衡，并给予葡萄糖、生理盐水林格液或林格乳酸盐的静脉输液，以恢复细胞外液量和电解质。一旦能够保留液体，随即给予口服营养。液体有助于支持毒素的排泄。对于这些除草剂过量接触的支持性措施通常足以成功处理。/其他除草剂/

If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and and fluid balance and administer intravenous infusions of glucose, normal saline ringer's solution, or ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. Fluids serve to support excretion of the toxicants. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other Herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大多数通过根系被吸收；通过叶子和茎的吸收较少。实验证据表明，西杜隆（Siduron）会在木质部中转移。

Most readily absorbed through root system; less so through foliage and stems. ... Experimental evidence indicates that Siduron is translocated in the xylem.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN3077 (solid); UN3082(liquid)
• WGK Germany：
  2
• RTECS号：
  YT7350000
• 海关编码：
  2924299034
• 安全说明：
  S26,S61

制备方法与用途

用途
用于草皮上防除一年生禾本科杂草的专用除草剂

类别
农药

毒性分级
中毒

急性毒性
口服 - 大鼠 LD50：5000 毫克/公斤

可燃性危险特性
燃烧时会产生有毒氮氧化物气体

储运特性
应存放在通风、低温和干燥的库房中，并与食品原料分开储存和运输

灭火剂
干粉、泡沫或砂土

反应信息

• 作为产物：
  描述：

  2-甲基环己胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 生成 环草隆
  参考文献：
  名称：

  通过β-消除卤代甲烷的新方法合成异氰酸酯和脲

  摘要：

  描述了通过卤代N-单取代的三卤代乙酰胺的碱诱导的β-消除新合成的异氰酸酯。反应速率显示出对三卤代甲基基团的强烈依赖性。因此，尽管三溴乙酰胺的反应在室温下进行并且三氯乙酰胺的反应需要在极性溶剂中加热，但是对于任何相应的三氟衍生物都没有观察到反应。从稳定且容易获得的三卤代乙酰胺中去除卤素的这种新颖的β-消除方法可用于尿素的“一锅法”合成，避免了使用光气和分离异氰酸酯。

  DOI：

  10.1016/s0040-4039(99)00372-x

文献信息

• [EN] 3-[(HYDRAZONO)METHYL]-N-(TETRAZOL-5-YL)-BENZAMIDE AND 3-[(HYDRAZONO)METHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE DERIVATIVES AS HERBICIDES<br/>[FR] DÉRIVÉS DE 3-[(HYDRAZONO))MÉTHYL]-N-(TÉTRAZOL-5-YL)-BENZAMIDE ET DE 3-[(HYDRAZONO)MÉTHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE UTILISÉS EN TANT QU'HERBICIDES
  申请人：SYNGENTA CROP PROTECTION AG

  公开号：WO2021013969A1

  公开（公告）日：2021-01-28

  The present invention related to compounds of Formula (I): or an agronomically acceptable salt thereof, wherein Q, R2, R3, R4, R5 and R6 are as described herein. The invention further relates to compositions comprising said compounds, to methods of controlling weeds using said compositions, and to the use of compounds of Formula (I) as a herbicide.

  本发明涉及以下式（I）的化合物或其农业上可接受的盐，其中Q、R2、R3、R4、R5和R6如本文所述。该发明还涉及包含所述化合物的组合物，使用这些组合物控制杂草的方法，以及将式（I）的化合物用作除草剂的用途。
• [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）

表征谱图