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氯草敏 | 1698-60-8

中文名称
氯草敏
中文别名
5-氨基-4-氯-2-苯基-3(2H)-哒嗪酮;1-苯基-4-氨基-5-氯-6-哒唑;5-氨基-4-氯-2-苯基哒嗪-3-酮;杀草敏;膦基聚羧酸
英文名称
chloridazon
英文别名
4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone;5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone;5-amino-4-chloro-2-phenylpyridazin-3(2H)-one;5-amino-4-chloro-2-phenyl-3(2H)-pyridazone;1-phenyl-4-amino-5-chloropyridazin-6-one;5-amino-4-chloro-2-phenylpyridazin-3-one
氯草敏化学式
CAS
1698-60-8
化学式
C10H8ClN3O
mdl
MFCD00055402
分子量
221.646
InChiKey
WYKYKTKDBLFHCY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    198-200°C
  • 沸点:
    312.2±52.0 °C(Predicted)
  • 密度:
    1.4884 (rough estimate)
  • 溶解度:
    氯仿(少量溶解)、DMSO(少量溶解)、甲醇(少量溶解)
  • LogP:
    1.140
  • 颜色/状态:
    Colorless solid
  • 气味:
    Odorless
  • 蒸汽压力:
    4.50X10-7 mm Hg at 20 °C
  • 稳定性/保质期:
    Stable up to 50 °C for >=2 yr. Stable in aqueous media at pH 3-9. Disappearance half-life in simulated sunlight 150 hr (pH 7, water).
  • 腐蚀性:
    NONCORROSIVE
  • 解离常数:
    pKa = 3.38 at 25 °C (UV method); pKa = 3.30 at 25 °C (polarography)
  • 碰撞截面:
    141.59 Ų [M+H]+ [CCS Type: TW]
  • 保留指数:
    2317.6

计算性质

  • 辛醇/水分配系数(LogP):
    0.8
  • 重原子数:
    15
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    58.7
  • 氢给体数:
    1
  • 氢受体数:
    3

ADMET

代谢
大约一半的吡唑隆/给/ ... 兔子被排泄 ... /作为/未改变的化学物质和 ... 2-(对-羟基苯基)类似物。 ... 在猫和狗上也得到了类似的结果,尽管 ... 排泄出更多的对-羟基代谢物而不是未改变的吡唑隆。对吡唑隆的研究表明,在应用到甜菜后形成了5-氨基-4-氯-3-氧-(2H)-吡啶。还检测到了第二种代谢物 ... 但未确定其身份。
Approximately half amount of pyrazon /fed/ ... to rabbits was excreted ... /as/ unchanged chemical and ... 2-(p-hydroxyphenyl) analog. ... Similar results were obtained with cats and dogs although ... more p-hydroxy metabolite was excreted than unchanged pyrazon. Studies with pyrazon indicated that 5-amino-4-chloro-3-oxo-(2H)-pyridazine was formed after application to beets. A second metabolite was also detected ... but was not identified.
来源:Hazardous Substances Data Bank (HSDB)
代谢
/Pyrazon/ ... /在大鼠中/ 尿液中总共检测到10个馏分(九个代谢物和一个同分异构体),粪便中检测到5个馏分。主要的尿液代谢物是硫酸盐和葡萄糖醛酸苷结合物,而主要的粪便代谢物是Pyrazon的p-羟基衍生物。硫酸盐和葡萄糖醛酸苷结合物以及Pyrazon的p-羟基衍生物被识别为胆汁代谢物...
/Pyrazon/ ... /In rats/ A total of 10 fractions (nine metabolites and one isomer) in the urine and 5 fractions in the feces were noted. The major urinary metabolites were sulfate and glucuronide conjugates and the major fecal metabolite was a p-hydroxy derivative of Pyrazon. The sulfate and glucuronide conjugates and p-hydroxy derivative of pyrazon were recognized as the biliary metabolites ...
来源:Hazardous Substances Data Bank (HSDB)
代谢
一张图片,展示了美国纽约市曼哈顿的天际线,其中包括著名的帝国大厦和自由女神像,背景是晴朗的蓝天,前景是哈德逊河,河面上有几艘游船。图片中充满了现代都市的气息,展现了纽约的繁华与活力。
A photochemically controlled process was involved in the degradation of pyrazon in the leaves of beets. No degradation occurs in the dark. In sugar beets and red beets, pyrazon formed N-glucosylpyrazone. In addition 5-amino-4-chloro-3(2H)-pyridazinone and a strongly hydrophilic compound were formed.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
吡唑隆[5-氨基-4-氯-2-苯基-3(2H)-哒嗪酮],也称为氯乙哒嗪,是一种属于哒嗪酮类杀虫剂的除草剂。它通过阻断绿色植物的光系统II中的电子传递来发挥除草作用,从而抑制光合作用。吡唑隆被注册用于甜菜和红餐桌甜菜的种植前、出苗前和早期出苗后使用,以控制某些杂草。大约有10%的美国甜菜作物和50%的美国餐桌甜菜作物每年使用吡唑隆。吡唑隆还注册用于商业观赏植物,包括球根作物和玫瑰。关于吡唑隆的毒性数据足以评估化学品的危险潜力。吡唑隆被认为是一种低毒性的除草剂,在哺乳动物中没有高度特异性的反应。技术吡唑隆通过口服、皮肤和吸入途径的急性毒性较低(类别III/IV)。它不是眼睛或皮肤的刺激物(类别IV),也不会引起皮肤致敏。在长期研究中,实验室动物接触吡唑隆的最显著效果似乎是体重减轻,这与食物摄入量减少有关。在较高剂量下,大鼠会出现一些与营养不良有关的总体外观不佳和一些运动效应。在狗身上,较高剂量会导致肾远端小管空泡化。吡唑隆的皮肤接触没有产生系统性影响。在大鼠和兔子的产前发育研究中,吡唑隆没有显示出对胎儿的任何影响,也没有表明增加敏感性。对大鼠的生殖性能没有影响。鉴于在接触吡唑隆后缺乏产前和/或产后敏感性,并且考虑到产前和/或产后毒性的残留不确定性,不需要特别的FQPA安全因子。因此,特别FQPA安全因子降为1X。在大鼠和兔子的产前发育毒性研究或大鼠多代繁殖研究中,没有观察到神经行为改变或神经病理学效应的证据。此外,根据其他指南研究或公开文献报告,吡唑隆不认为是神经毒性的。在大鼠中,在非常高的剂量下注意到一些提示神经毒性的临床迹象,但这些归因于大鼠的体重减轻和总体状况不佳。根据证据权重,吡唑隆不需要进行发育神经毒性(DNT)研究。根据大鼠和小鼠致癌性研究中缺乏致癌性的证据,吡唑隆可能被归类为“不太可能在人类中是致癌物”。
Pyrazon [5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone], also known as chloridazon, is an herbicide belonging to the pyridazinone class of pesticides. It works as an herbicide by blocking electron transport in photosystem II in green plants, thereby inhibiting photosynthesis. Pyrazon is registered for pre-plant, pre-emergence, and early post-emergence use on sugar beets and red table beets to control certain weeds. Approximately 10% of the U.S. sugar beet crop and 50% of the U.S. table beet crop are treated with pyrazon annually. Pyrazon is also registered for commercial use on ornamentals, including bulb crops and roses. The available toxicity data on pyrazon are adequate to assess the chemical's hazard potential. Pyrazon is an herbicide considered to be of low toxicity without highly specific responses in mammals. Technical pyrazon has low (category III/IV) acute toxicity via the oral, dermal, and inhalation routes of exposure. It is not an eye or skin irritant (category IV) and does not cause dermal sensitization. In longer-term studies, reduced body weight associated with reduced food consumption appears to be the most significant effect of pyrazon exposure in laboratory animals. At higher doses, conditions such as poor general appearance and some motor effects considered to be associated with poor nutrition are noted in rats. In dogs, renal distal tubule vacuolation results at higher doses. No systemic effects resulted from dermal exposure to pyrazon. In both the rat and rabbit prenatal developmental studies, pyrazon did not demonstrate any effects on the fetuses to indicate increased susceptibility. There were no effects on the reproductive performance of rats. Based on the lack of pre- and/or postnatal susceptibility resulting following exposure to pyrazon, and considering the lack of residual uncertainties for pre- and/or postnatal toxicity, no special FQPA safety factor is needed. Therefore, the special FQPA safety factor was reduced to 1X. No neurobehavioral alterations or evidence of neuropathological effects were observed in the available rat and rabbit prenatal developmental toxicity studies or the rat multi-generation reproduction study. In addition, pyrazon is not considered to be neurotoxic from other guideline studies or in open literature reports. Some clinical signs suggesting neurotoxicity were noted at very high doses in the rat, but these were attributed to the weight loss and general poor condition of the rats. Based on the weight of evidence, a developmental neurotoxicity (DNT) study is not required for pyrazon. Pyrazon may be classified as "not likely to be a carcinogen in humans" based on the lack of evidence of carcinogenicity in the rat and mouse carcinogenicity studies.
来源:Hazardous Substances Data Bank (HSDB)
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
  • 副作用
职业性肝毒素 - 第二性肝毒素:在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒病例。
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 毒性数据
LC50 (大鼠) > 30,800 毫克/立方米/4小时
LC50 (rat) > 30,800 mg/m3/4h
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 相互作用
在存在10毫摩尔硫氰酸钠和0.1摩尔亚硝酸钠的pH为1的条件下(类似于胃部环境),10毫摩尔的吡唑隆会反应生成N-甲基-N-亚硝基苯胺。在使用大肠杆菌K-12(343/113)进行体外系统的诱变性测试时,吡唑隆并未显示出诱变性。在存在代谢活性的肝微粒体时,其衍生物诱发了突变。
In the presence of 10 mmol sodium thiocyanate and 0.1 mole sodium nitrite at pH 1 (similar to stomach conditions), 10 mmol pyrazon reacts to n-methyl-nitroso-aniline. When mutagenicity was tested using Escherichia coli K-12 (343/113) in an in vitro system, pyrazon was not mutagenic. The derivatives induced mutations in the presence of metabolically active liver microsomes.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
毒物动力学数据表明,大鼠胃肠道能够很好地吸收草达松。主要的排泄途径是通过尿液,低剂量的大部分在24小时内排出,高剂量的则在48小时内排出。胆汁排泄虽然有意义,但只是次要途径。根据14天重复剂量研究,雌性可能比雄性以较低的速率排泄草达松。组织中负荷较低,最多只有3.28%残留...在尿液和粪便中仅检测到少量的母化合物。与性别相关的较小定量差异被确定。
The toxicokinetic data indicate that pyrazon is readily absorbed by the rat gastrointestinal tract. The major excretory route is via the urine with most being excreted in 24 hours for low doses and 48 hours for higher doses. Biliary excretion is significant but a minor route. Females may excrete Pyrazon at lower rates than males based on the 14 day repeat dose study. Tissue burden is low with up to only 3.28% remaining ... Parent compound was detected only in small amounts in the urine and feces. Minor quantitative differences related to gender were identified.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
大约一半的吡唑隆/给/兔子的剂量在24小时内通过尿液排出...口服技术级吡唑隆/给兔子/后排出的尿液中包括...未改变的吡唑隆和其对羟基代谢物...还有异吡唑隆,作为技术配方中的杂质存在,以及它的对羟基代谢物。在猫和狗上也得到了类似的结果...
Approximately half amount of pyrazon /fed/ ... to rabbits was excreted in urine within 24 hr ... Urinary excretion products resulting from oral administration of technical pyrazon /to rabbits/ included...unchanged pyrazon and p-hydroxy metabolite ... also isopyrazon, present in technical formulation as impurity, and its p-hydroxy metabolites. Similar results were obtained with cats and dogs ...
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
叶面吸收发生,但对除草作用的重要性不大。从处理过的叶子到其他部位的转移是有限的。根系吸收迅速,随后转运到植物的所有部位表明是通过木质部运输的。
Foliar absorption occurs but is not of major importance to herbicidal action. Translocation from treated leaves is limited. ... Root absorption is rapid and subsequent translocation to all plant parts suggests xylem transport.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在藜(Chenopodium album L)中,吡唑隆在叶片中积累,但被根部代谢。
In lambsquarters, (Chenopodium album L), pyrazon was accumulate in the leaves but metabolized by roots.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    IRRITANT
  • 危险品标志:
    Xi,N
  • 安全说明:
    S24,S37,S60,S61
  • 危险类别码:
    R50/53,R43
  • WGK Germany:
    2
  • 危险品运输编号:
    3077
  • RTECS号:
    UR6125000
  • 海关编码:
    2933990017
  • 危险类别:
    IRRITANT
  • 储存条件:
    建议储存于0-6°C的环境中,并保持密封。

SDS

SDS:09f0ae2cd7aa2c55b1aae6447af15a00
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制备方法与用途

用途:用作钻井泥浆添加剂
类别:农药
毒性分级:中毒
急性毒性:

  • 大鼠经口 LD50:647 毫克/公斤
  • 小鼠经口 LD50:1000 毫克/公斤

刺激数据:

  • 兔子眼睛接触 500 毫克/24 小时 轻度

可燃性危险特性: 燃烧会产生有毒氯化物和氮氧化物气体

储运特性: 应存放在通风、低温、干燥的库房内,并与食品原料分开存放和运输

灭火剂:干粉、泡沫、砂土

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    氯草敏 氢气 作用下, 以 ammonium hydroxide氯仿 为溶剂, 110.0 ℃ 、5.0 MPa 条件下, 反应 0.5h, 生成 甲磺美嗪
    参考文献:
    名称:
    Reicheneder; Burger; Koenig, Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 9 A, p. 1529 - 1533
    摘要:
    DOI:
  • 作为产物:
    描述:
    参考文献:
    名称:
    Method for producing 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone from
    摘要:
    4-氯-5-氨基-2-苯基-3(2H)-吡啶并咪唑酮是通过在高产率下从4,5-二氯-2-苯基-3(2H)-吡啶并咪唑酮和氨的反应中制备的,且基本上不含4-氨基-5-氯-2-苯基-3(2H)-吡啶并咪唑酮。该方法包括在存在能够选择性交换4,5-二氯-2-苯基-3(2H)-吡啶并咪唑酮中的5-氯原子的催化剂的情况下,将4,5-二氯-2-苯基-3(2H)-吡啶并咪唑酮与水溶氨反应,生成的中间化合物能够高产率地烷基化氨为4-氯-5-氨基-2-苯基-3(2H)-吡啶并咪唑酮,从而再生催化剂。在反应后通过过滤分离出最终产物并用水洗涤,母液和洗涤水用作下一批的反应介质。
    公开号:
    US04454318A1
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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] 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。
  • TRIAZOLE ACC INHIBITORS AND USES THEREOF
    申请人:Gilead Apollo, LLC
    公开号:US20170166584A1
    公开(公告)日:2017-06-15
    The present invention provides triazole compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
    本发明提供了三唑化合物,可用作乙酰辅酶A羧化酶(ACC)的抑制剂,以及其组合物和使用方法。
  • 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。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
cnmr
ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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