溴代吡咯腈 | 122454-29-9

• 物质功能分类: 分析化学 - 标准品 - 农残、兽药及化肥类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 溴代吡咯腈
• 中文别名: 曲洛比利；4-溴代-2-(4-氯苯基)-5-(三氟甲基)-1HH30-吡咯-3-甲腈；4-溴-2-(4-氯苯基)-5-三氟甲基-1H-吡咯-3-甲腈
• 英文名称: tralopyril
• 英文别名: 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile；4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile；Econea；4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-nitrile；4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile
• CAS: 122454-29-9
• 化学式: C₁₂H₅BrClF₃N₂
• 分子量: 349.537
• InChiKey: XNFIRYXKTXAHAC-UHFFFAOYSA-N

物化性质

• 沸点：
  450.6±45.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  N
• 安全说明：
  S60,S61
• 危险类别码：
  R50/53
• 危险品运输编号：
  UN 3077 9 / PGIII

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Tralopyril
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. : 122454-29-9
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 aquatic toxicity (Category 1), H400
Chronic aquatic toxicity (Category 1), H410
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
N Dangerous for the R50/53
environment
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)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Molecular Weight : 349,53 g/mol
CAS-No. : 122454-29-9
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-
Aquatic Acute 1; Aquatic -
Chronic 1; H410
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-
N, R50/53 -
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), Hydrogen chloride gas, Hydrogen bromide gas, Hydrogen fluoride
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
Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
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.
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
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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. Discharge into
the environment must be avoided.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH 5,16 at 1 g/l at 22 °C
e) Melting point/freezing Melting point/range: 252 - 254 °C - lit.
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 hydrolyses
o) Partition coefficient: n- log Pow: 3,5
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
Solubility in other Methanol 109,1 g/l at 20 °C
solvents

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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
no data available
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
no data available
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: Not available
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
Very toxic to aquatic life with long lasting effects.

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. 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: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (1H-Pyrrole-3-
carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (1H-Pyrrole-3-
carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-)
IATA: Environmentally hazardous substance, solid, n.o.s. (1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-
chlorophenyl)-5-)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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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.
Aquatic Acute Acute aquatic toxicity
Aquatic Chronic Chronic aquatic toxicity
H400 Very toxic to aquatic life.
H410 Very toxic to aquatic life with long lasting effects.
Full text of R-phrases referred to under sections 2 and 3
N Dangerous for the environment
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
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

理化性质

溴代吡咯腈外观呈浅棕色粉末，具有良好的热稳定性，并且可以与氧化亚铜、硫氰酸亚铜及所有有机或有机金属的抗菌剂以及氧化锌和氧化铁稳定共存。该物质可以在水中水解，在常温下可稳定保存5年。

毒性

溴代吡咯腈经口毒性较大，吸入毒性中等，经皮毒性为低毒。对大鼠皮肤和眼睛有轻微刺激作用，但对豚鼠皮肤无致敏性。具体毒理数据如下：

• 大鼠无作用剂量[mg/(kg·d)]（90天）：雄性16.2 mg/(kg·d)，雌性6.3 mg/(kg·d)；
• 通过经皮途径的无作用剂量（90天）为300 mg/(kg·d)；
• 在最高剂量1000 mg/(kg·d)下，未见全身中毒症状。

嗅觉器官毒性测试显示，最低剂量为20 mg/m³。神经系统毒性测试结果显示，降低活动反应能力的最低剂量为40 mg/m³，导致雌大鼠身体某部位神经突出的最低剂量为80 mg/m³；对雄性及雌性大鼠的无作用剂量（NOEL）分别为20 mg/m³和40 mg/m³。

此外，使大鼠胎儿体重减小的最低剂量为10 mg/(kg·d)，而NOEL为5 mg/(kg·d)。对于雌大鼠的症状表现，经常分泌唾液的最低剂量为10 mg/(kg·d)，NOEL同样为5 mg/(kg·d)。

反应信息

• 作为反应物：
  描述：

  溴代吡咯腈 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到4-bromo-2-(4-chlorophenyl)-5-(trimethoxymethyl)-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  新型2-吡咯碳酰胺和2-吡咯碳酸酯的三氟甲基转化合成，晶体结构和杀虫活性

  摘要：

  2-苯基吡咯的两个系列：3-溴-5-（4-氯苯基）-4-氰基吡咯-2-羧酰胺（5a – 5d）和3-溴-5-（4-氯苯基）-4-氰基吡咯-2-通过新颖的三氟甲基转化合成了羧酸盐（6a - 6c）。杀虫生物测定的结果表明，6a - 6c对东方粘虫具有中等杀幼虫活性，而6b也具有良好的杀螨活性，因此预计3-溴-5-（4-氯苯基）-4-氰基吡咯-2-羧酸酯衍生物将成为新农药的先导化合物。

  DOI：

  10.1016/j.bmcl.2012.09.036
• 作为产物：
  描述：

  DL-对氯苯甘氨酸 在 溴 、 sodium acetate 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 反应 7.17h， 生成 溴代吡咯腈
  参考文献：
  名称：

  2-芳基取代吡咯类化合物在杀双脐螺药物中 的应用

  摘要：

  本发明涉及一种2‑芳基取代吡咯类化合物在杀双脐螺药物中的应用，属于血吸虫病防治技术领域。本发明具体提供2‑芳基取代吡咯类化合物的化学结构及其制备方法，并以2‑芳基取代吡咯类化合物活性成分制备成杀螺剂，杀螺剂形态为悬浮剂、乳剂、微乳剂，应用于双脐螺杀灭。所述2‑芳基取代吡咯类化合物作为杀螺剂活性成分时，浸杀的使用量为0.5mg/L‑10.00mg/L，浸杀时间为24h‑72h。通过实验证实，2‑芳基取代吡咯类化合物对双脐螺有杀灭活性，且对水生生物的毒性低于现有杀螺药物氯硝柳胺，可以制备成杀螺制剂应用于血吸虫病防治领域。

  公开号：

  CN109006824B

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。
• 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] 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。
• MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
  申请人：Dow AgroSciences LLC

  公开号：US20170210723A1

  公开（公告）日：2017-07-27

  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, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and 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，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的组合物，以及使用这种分子和组合物对抗这些害虫的过程。这些分子和组合物可以用作杀螨剂、杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂。本文件披露了具有以下式（“式一”）的分子。
• HYDRAZONYL GROUP-CONTAINING CONDENSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US20190177319A1

  公开（公告）日：2019-06-13

  An object of the present invention is to develop and provide a novel agricultural and horticultural insecticide in view of the still immense damage caused by insect pests etc. and the emergence of insect pests resistant to existing insecticides in crop production in the fields of agriculture, horticulture and the like. Provided is a hydrazonyl group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by the general formula (1): wherein R 1 represents, for example, an alkyl group, R 2 represents, for example, a hydrogen atom, R 3 and R 4 each represent, for example, an alkyl group, a haloalkyl group or an acyl group, A 1 represents, for example, a nitrogen atom, A 2 represents, for example, N-Me or an oxygen atom, A 3 represents, for example, a carbon atom or a nitrogen atom, A 4 represents, for example, C—H, m represents, for example, 2, and n represents, for example, 1}, or a salt thereof; an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

  本发明的一个目的是开发并提供一种新型农艺和园艺杀虫剂，鉴于昆虫害虫等造成的损害仍然巨大，以及在农业、园艺等领域作物生产中出现的对现有杀虫剂具有抗性的昆虫害虫。 提供了一种含有肼酰基的稠合杂环化合物或其盐，优选为通式(1)表示的稠合杂环化合物： 其中R1代表例如烷基，R2代表例如氢原子，R3和R4各自代表例如烷基、卤代烷基或酰基，A1代表例如氮原子，A2代表例如N-Me或氧原子，A3代表例如碳原子或氮原子，A4代表例如C—H，m代表例如2，n代表例如1}，或其盐；一种包含该化合物或其盐作为活性成分的农艺和园艺杀虫剂；以及使用该杀虫剂的方法。