帕苯达唑 | 14255-87-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 帕苯达唑
• 中文别名: 丁苯咪胺酯；帕苯咪唑；丁苯咪酯；丁苯咪唑；虫帕唑；5-丁基-2-苯并咪唑氨基甲酸甲酯
• 英文名称: parbendazole
• 英文别名: methyl N-(6-butyl-1H-benzimidazol-2-yl)carbamate
• CAS: 14255-87-9
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: YRWLZFXJFBZBEY-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257°C
• 沸点：
  390.33°C (rough estimate)
• 密度：
  1.1214 (rough estimate)
• 溶解度：
  可溶于DMSO（略微加热）、甲醇（略微加热）
• 物理描述：
  Crystals or fine white powder. (NTP, 1992)
• 碰撞截面：
  164.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37,S36/37/39
• 危险类别码：
  R22,R20/21/22,R36/37/38,R63
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险品运输编号：
  2811
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Parbendazole
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 14255-87-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Reproductive toxicity (Category 2), H361
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R63
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H361 Suspected of damaging fertility or the unborn child.
Precautionary statement(s)
P281 Use personal protective equipment as required.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Methyl (5-butyl-1H-benzoimidazol-2-yl)carbamate
Methyl 5(6)-butyl-2-benzimidazolecarbamate
Formula : C13H17N3O2
Molecular Weight : 247,29 g/mol
CAS-No. : 14255-87-9
EC-No. : 238-133-3
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Parbendazole
Acute Tox. 4; Repr. 2; H302, -
H361
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Parbendazole
Xn, R22 - R63 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour odourless
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 255 - 257 °C - lit. - Decomposes on heating.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility 0,01 g/l at 18 °C
o) Partition coefficient: n- log Pow: 3,43
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - > 40 mg/kg
LD50 Oral - mouse - 1.700 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Laboratory experiments have shown teratogenic effects.
Reproductive toxicity - rat - Oral
Effects on Embryo or Fetus: Fetal death. Specific Developmental Abnormalities: Central nervous system.
Specific Developmental Abnormalities: Craniofacial (including nose and tongue).
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: DD6495000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
H361 Suspected of damaging fertility or the unborn child.
Repr. Reproductive toxicity
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R63 Possible risk of harm to the unborn child.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

帕苯咪唑 用途

帕苯咪唑（5-正丁基-2-苯并咪唑氨基甲酸甲酯）是一种广谱高效的驱虫药，特别针对隐藏管状线虫、旋形线虫、猪蛔虫、血矛线虫、圆线虫、消化道线虫、胃毛圆线虫、细颈线虫、喉结线虫和羊肠线虫等具有高度的驱杀效果。

制备

帕苯咪唑的制备过程包括五个反应步骤：乙酰化、硝化、水解、还原和成环。首先以对正丁基苯胺为原料，使用醋酐进行乙酰化处理；随后用硝酸进行硝化；将产物倒入冰水中析出固体并抽滤，用水洗涤至中性后干燥，得到4-正丁基-2-硝基乙酰苯胺。接着，该干燥产物被氢氧化钾溶液水解，并使用4mol/L～5mol/L的盐酸调节pH值为6～7，然后进行减压浓缩。残余物用乙醚萃取，收集有机相并浓缩，最终得到4-正丁基-2-硝基苯胺。将制得的4-正丁基-2-硝基苯胺溶于甲醇，并加入钯碳作催化剂抽滤后，再用甲醇、乙酸和氰氨基甲酸甲酯制备5-正丁基-2-苯并咪唑氨基甲酸甲酯（帕苯咪唑）。

生物活性

Parbendazole (SKF 29044) 是一种非常有效的微管组装抑制剂，对于脑微管组装的IC50值为3 µM。在无细胞实验中，其靶点是微管。

靶点

Target	Value
Microtubule	3 μM

体外研究

帕苯咪唑是一种微管解聚剂，EC50值为530 nM，并能诱导DNA损伤。在2-10 µM的浓度下，帕苯咪唑以剂量依赖性方式抑制微管组装，IC50值为3 µM；处理后的Vero细胞完全缺乏微管。2-20 µM浓度的帕苯咪唑可抑制CLd-AXE霉蹄虫的生长，并在2-5 µM时高效抑制野生型霉蹄虫纯化的微管。

类别

有毒物质

毒性分级

中毒

急性毒性

• 大鼠口服 LD50: ＞40 毫克/公斤
• 小鼠口服 LD50: 1700 毫克/公斤

可燃性危险特性

热分解排出有毒氮氧化物烟雾

储运特性

库房应保持通风、低温和干燥

灭火剂

• 水
• 干粉
• 干砂
• 二氧化碳
• 泡沫
• 1211灭火剂

反应信息

• 作为反应物：
  描述：

  帕苯达唑 以65%的产率得到
  参考文献：
  名称：

  LACEY, E., J. LABELLED COMPOUNDS AND RADIOPHARM., 1985, 22, N 9, 893-902

  摘要：

  DOI：

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。
• [EN] ANTHELMINTIC AGENTS AND THEIR USE<br/>[FR] AGENTS ANTHELMINTIQUES ET LEUR UTILISATION
  申请人：INTERVET INT BV

  公开号：WO2010115688A1

  公开（公告）日：2010-10-14

  This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.

  这项发明涉及一般用作驱虫剂或作为制备驱虫剂的中间体的化合物和盐。这项发明还涉及制备这些化合物和盐的方法，包括这些化合物和盐的药物组合物和试剂盒，使用这些化合物和盐制备药物，以及将这些化合物和盐用于需要治疗的动物的治疗方法。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。
• ISOXAZOLINE DERIVATIVES AS INSECTICIDES
  申请人：Pitterna Thomas

  公开号：US20120316124A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 17 , R 18 , R 19 and R 20 are as defined in claim 1 ; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被1至5个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。
• ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND METHOD OF USING THEREOF
  申请人：Meng Charles Q.

  公开号：US20140142114A1

  公开（公告）日：2014-05-22

  The present invention relates to novel anthelmintic compounds of formula (I) below: wherein Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.

  本发明涉及以下式（I）的新型驱虫化合物： 其中 Y和Z分别是双环碳环或双环杂环基团，或者Y或Z中的一个是双环碳环或双环杂环基团，另一个是烷基，烯基，炔基，环烷基，苯基，杂环基或杂芳基，以及变量X 1 ，X 2 ，X 3 ，X 4 ，X 5 ，X 6 ，X 7 和X 8 如本文所定义。本发明还提供了包含本发明的驱虫化合物的兽药组合物，以及它们用于治疗和预防动物寄生虫感染的用途。