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甲羧除草醚 | 42576-02-3

中文名称
甲羧除草醚
中文别名
5-(2,4-二氯苯氧基)-2-硝基苯甲酸甲酯;治草醚;茅毒;甲酯除草醚
英文名称
bifenox
英文别名
methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
甲羧除草醚化学式
CAS
42576-02-3
化学式
C14H9Cl2NO5
mdl
——
分子量
342.135
InChiKey
SUSRORUBZHMPCO-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:
    84-86°
  • 沸点:
    421.0±45.0 °C(Predicted)
  • 密度:
    1.5715 (rough estimate)
  • 溶解度:
    氯仿(微溶)、乙酸乙酯(微溶)
  • LogP:
    4.480
  • 颜色/状态:
    Solid
  • 气味:
    Slightly aromatic odor
  • 蒸汽压力:
    2.4X10-6 mm Hg @ 25 °C
  • 稳定性/保质期:

    常规情况下不会分解,也没有危险反应。该物质无严重吸入毒性,对眼睛无刺激。高剂量下喂给大鼠和火鸡也未产生病理学及组织学变化。此外,它无致畸、致癌或致突变作用。

  • 腐蚀性:
    ...Virtually noncorrosive to most spray equipment materials, but is mildly corrosive to aluminum.
  • 保留指数:
    2498;2505;2515;2493.4;2498

计算性质

  • 辛醇/水分配系数(LogP):
    4.5
  • 重原子数:
    22
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.07
  • 拓扑面积:
    81.4
  • 氢给体数:
    0
  • 氢受体数:
    5

ADMET

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) > 910 mg/m³
LC50 (rat) > 910 mg/m3
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 解毒与急救
基本治疗:建立专利气道。如有必要,进行吸痰。观察呼吸不足的迹象,并在需要时辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺肿,并在必要时进行治疗……。监测休克,并在必要时进行治疗……。预期癫痫发作,并在必要时进行治疗……。对于眼睛污染,立即用冲洗眼睛。在转运过程中,用生理盐连续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的干呕反射且不流口,则用冲洗口腔,并给予5毫升/千克,最多200毫升的进行稀释……。在去污后,用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
高级治疗:对于昏迷、严重肺肿或呼吸停止的患者,考虑进行口咽或鼻咽插管以控制气道。使用带有气囊面罩的装置进行正压通气技术可能有益。监测心率和必要时治疗心律失常。开始静脉输液,使用5%葡萄糖/生理盐维持静脉通路开放,最小流量。如果出现低血容量的迹象,使用乳酸钠林格氏液。注意观察液体过载的迹象。考虑使用药物治疗肺肿。对于伴有低血容量迹象的低血压,谨慎给予液体。注意观察液体过载的迹象。使用地西泮安定)治疗癫痫。使用丙美卡因化物协助眼部冲洗。/毒药A和B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
实验室动物:急性暴露/ ...研究了四种二苯醚(DPEs)的细胞毒性和促卟啉生成效应/...在大鼠肝细胞在Matrigel上培养的情况下。细胞毒性通过乳酸脱氢酶释放量的减少来确定存活率。在...双苯醚处理的肝细胞中,直到1.0 mM的浓度下,没有观察到浓度依赖性的存活率下降。在...双苯醚的情况下,最大卟啉积累在...0.25 mM观察到(增加21倍)。
/LABORATORY ANIMALS: Acute Exposure/ ...The cytotoxic and porphyrinogenic effects of four diphenyl ethers (DPEs) /were studied/... in rat hepatocytes cultured on Matrigel. Cytotoxicity was determined as a decr in viability measured by the release of lactate dehydrogenase. ...No concn-dependent decr in viability was observed in the ...bifenox-treated hepatocytes at the concns up to 1.0 mM. ...The max porphyrin accumulation was observed at ...0.25 mM for ...bifenox (...21-fold).
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
Bifenox 在体内相对快速地被吸收和排出;5-(2,4-二氯苯基)-2-硝基苯甲酸是主要的尿液代谢物,没有检测到 Bifenox。Bifenox 和 5-(2,4-二氯苯基)酸在粪便中被检测到。
Bifenox is relatively rapidly absorbed and eliminated from the body; 5-(2,4-dichlorophenyl)-2-nitrobenzoic acid was the major urinary metabolite, with no bifenox detected. Bifenox together with 5-(2,4-dichlorophenyl)anthranilate were detected in feces.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
技术等级的双芬nox(98%纯度)在悬浮于1%羧甲基纤维素后口服给药,剂量为2克/千克,给予6只青年山羊,雌雄各半,用于口服动力学研究。在不同时间间隔从每只山羊采集血液样本,并通过气相色谱法估算血液中双芬nox的浓度。血液中在2小时(1.32 + 或 - 0.07微克/毫升)检测到双芬nox,在12小时达到最大值(6.76 + 或 - 0.17微克/毫升),随后浓度逐渐下降,在24小时达到最低血液浓度。双芬nox的动力学行为遵循“两室开放模型”。分布容积/区域和/血液清除率/值分别为...2.73 + 或 - 0.28升/千克和0.88 + 或 - 0.07升/千克/小时,表明在体内分布广泛且持久性较短。
...Bifenox technical grade (98% purity) was administered orally after suspending in 1% carboxymethyl cellulose at 2 g/kg to 6 young adult goats of both sexes for oral kinetics. Blood samples were collected at different time intervals from each goat and concn of bifenox in blood were estimated by GLC. Bifenox in blood was detected at 2 hr (1.32 + or - 0.07 ug/ml) which attained max at 12 hr (6.76 + or - 0.17 ug/ml) followed by gradual decr in concn and reaching at min blood concn at 24 hr. The kinetic behavior of bifenox followed "two compartment open model". The .../volume of distribution/ area and /blood clearance/ values were ...2.73 + or - 0.28 l/kg and 0.88 + or - 0.07 l/kg/hr respectively, indicating wide distribution and shorter persistence in the body.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    N
  • 安全说明:
    S60,S61
  • 危险类别码:
    R50/53
  • WGK Germany:
    2
  • 海关编码:
    2918990090
  • 危险品运输编号:
    UN 3077 9/PG 3
  • RTECS号:
    DG7890000
  • 储存条件:
    密封、阴凉、干燥保存

SDS

SDS:064dd91cbe58f84712fc40e86b1dedb4
查看

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Bifenox
CAS-No. : 42576-02-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances



Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute aquatic toxicity (Category 1)
Chronic aquatic toxicity (Category 1)
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
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

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
Formula : C14H9Cl2NO5
Molecular Weight : 342,13 g/mol

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
Indication of any immediate medical attention and special treatment needed
no data available

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
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate
personnel to safe areas.
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.

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.
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)
no data available

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).

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
Colour: yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 84 - 89 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation 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 insoluble
o) Partition coefficient: n- log Pow: 4,48
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

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
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

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 6.400 mg/kg
LC50 Inhalation - rat - > 200.000 mg/m3
LD50 Dermal - rabbit - > 20.000 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
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
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: DG7890000

Section 12. ECOLOGICAL INFORMATION
Toxicity
Toxicity to fish LC50 - Oncorhynchus mykiss (rainbow trout) - > 0,18 mg/l - 96,0 h
Toxicity to daphnia and EC50 - Daphnia magna (Water flea) - > 0,35 mg/l - 48 h
other aquatic
invertebrates
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
Very toxic to aquatic life.
Avoid release to the environment.
no data available

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.

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. (Methyl 5-(2,4-
dichlorophenoxy)-2-nitrobenzoate)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Methyl 5-(2,4-
dichlorophenoxy)-2-nitrobenzoate)
IATA: Environmentally hazardous substance, solid, n.o.s. (Methyl 5-(2,4-dichlorophenoxy)-2-
nitrobenzoate)
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.

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
no data available

Section 16. OTHER INFORMATION
Further information
Copyright 2012 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

毒性分级:低毒

急性毒性:

  • 口服 - 大鼠 LD50: 6400 毫克/公斤
  • 口服 - 小鼠 LD50: 4556 毫克/公斤

可燃性危险特性: 燃烧产生有毒氮氧化物和化物气体

储运特性: 库房通风低温干燥;与食品原料分开储存运输

灭火剂: 干粉、泡沫、砂土

生产方法

制备方法一

  1. 解反应

  2. 化反应

  3. 酯化反应

    • 甲醇滴加到间苯甲酰氯中,配比为1:1 (mol),于25~68℃范围内反应。
    • 反应过程有轻微放热现象,可以调节加料速度,控制反应温度,回流2~3小时。
    • 反应过程中大量氯化氢逸出,过量的甲醇与残余氯化氢气体用真空排除,得无色间氯苯甲酸甲酯液体,收率98%~99%。
  4. 硝化反应

  5. 缩合反应

制备方法二

[具体步骤和数据缺失,请参考相关文献]

分类
  • 类别:农药

通过上述生产方法,可以合成具有低毒性的甲酯除草醚。在储存和运输过程中应注意通风低温干燥,并与食品原料分开存放以确保安全。灭火时可使用干粉、泡沫或砂土。

上下游信息

  • 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:
    参考文献:
    名称:
    Substituted diphenyl ethers
    摘要:
    一种化学式为:##STR1## 及其盐和酯,可用作化合物的中间体的制备,该化合物的化学式为##STR2## 其中R.sup.1是一种烷基基团,可选择地被一个或多个氟原子或一个可选择地被取代的苯基团取代,R.sup.2是No.sub.2或Cl,R.sup.6是一个氢原子或1至4个碳原子的烷基基团。