氟吡呋喃酮 | 951659-40-8

• 物质功能分类: 化学农药原药 - 杀虫剂 - 其他杀虫剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 氟吡呋喃酮
• 英文名称: flupyradifurone
• 英文别名: 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5H)-one；4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one；FPF；3-[(6-chloropyridin-3-yl)methyl-(2,2-difluoroethyl)amino]-2H-furan-5-one
• CAS: 951659-40-8
• 化学式: C₁₂H₁₁ClF₂N₂O₂
• 分子量: 288.681
• InChiKey: QOIYTRGFOFZNKF-UHFFFAOYSA-N

物化性质

• 熔点：
  69 - 71°C
• 沸点：
  457.7±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微，超声处理），甲醇（轻微）
• LogP：
  1.110 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  2

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Flupyradifurone
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. : 951659-40-8
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances
Uses advised against : Use only in area provided with appropriate exhaust ventilation.

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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
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
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.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C12H11ClF2N2O2
Molecular Weight : 288,68 g/mol
CAS-No. : 951659-40-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Flupyradifurone
CAS-No. 951659-40-8 Acute Tox. 4; H302 <= 100 %
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 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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. 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. 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
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.
Specific end use(s)
Apart 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
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: crystalline
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 69 °C
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 < 0,0000003 hPa at 50 °C
l) Vapour density no data available
m) Relative density ca.547 kg/m3
n) Water solubility 3,2 g/l at 20 °C
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition > 208 °C, 3 K/min -
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
Solubility in other Acetone > 250 g/l at 20 °C
solvents Methanol > 250 g/l at 20 °C
Toluene 3,7 g/l at 20 °C

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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, Strong acids and strong bases
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 - > 300 - < 2.000 mg/kg
LC50 Inhalation - rat - 4 h - > 4.671 mg/l
LD50 Dermal - rat - > 2.000 mg/kg
Skin corrosion/irritation
Skin - rabbit
Result: No skin irritation
Serious eye damage/eye irritation
Eyes - rabbit
Result: No eye irritation
Respiratory or skin sensitisation
- mouse
Result: Did not cause sensitisation on laboratory animals.
Germ cell mutagenicity
In vivo tests did not show mutagenic effects
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
Toxicity to fish LC50 - Oncorhynchus mykiss (rainbow trout) - > 74,2 mg/l - 96 h
Toxicity to daphnia and EC50 - Daphnia magna (Water flea) - > 77,6 mg/l - 48 h
other aquatic
invertebrates
Toxicity to algae IC50 - Pseudokirchneriella subcapitata - > 80 mg/l - 72 h
Toxicity to bacteria - Sludge Treatment - > 1.000 mg/l - 3 h
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
Harmful to aquatic life.
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with
an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

随着高毒农药在全球市场的退出，新烟碱类杀虫剂逐渐成为防治刺吸式害虫、小型鳞翅目和鞘翅目害虫最有效的一类杀虫剂。拜耳作物科学公司针对部分新烟碱类杀虫剂的高蜂毒问题，开发了一种新型新烟碱类杀虫剂——氟吡呋喃酮（flupyradifurone），该药剂可高选择性地作用于多种刺吸式口器害虫，速效性好、持效期长，并且与常规新烟碱类杀虫剂无交互抗性。其最突出的特点是对蜜蜂等传粉昆虫低毒。

理化性质

氟吡呋喃酮（试验代号 BY102960），商品名称 Sivanto，是拜耳公司开发的新烟碱、乙酰胆碱受体类杀虫剂。密度为 (1.41 ± 0.1) g/cm³ (20℃)，lgP=0.312 ± 0.496(25℃)。对蜜蜂安全，对温血动物毒性较低，适用于保护植物、提高采收率、改善作物品质和防治动物害虫。

适用范围

氟吡呋喃酮可用于防治番茄、辣椒、马铃薯、黄瓜、葡萄、西瓜、咖啡、坚果、柑橘及一些大田作物中的蚜虫、粉虱、介壳虫、叶蝉、西花蓟马、潜叶蝇、粉蚧、软蚧、柑橘木虱和马铃薯甲虫等多种害虫，具有良好的内吸性和传导性，对幼虫、成虫等所有生长时期害虫皆有效，并且药效快、持效期长。

作用机制

氟吡呋喃酮含有特殊的药效基团丁烯酸内酯，因此具有较好的内吸传导性。叶面喷施或进行种子处理后，能迅速传导至植株各部位，可有效防治叶面背部或隐蔽取食的害虫，并通过抑制昆虫的摄食，减少依赖昆虫介导的病原体传播。

使用安全性

氟吡呋喃酮最突出的优点是对蜜蜂等传粉昆虫低毒。虽然在较高剂量下仍会对蜜蜂觅食（对糖）和认知能力产生一定影响，但按照标签推荐剂量用药，则对其觅食行为、觅食蜜蜂、幼蜂和蜂群发育蜜蜂健康、蜂巢以及越冬蜂群均无不良影响。因此被美国环保署定为7类园艺作物与棉花种植的安全候选药物。

此外，氟吡呋喃酮对环境中非靶标生物的毒性较低，具体见表1。氟吡呋喃酮对虹鳟鱼、蚯蚓、水蚤、海藻、大黄蜂和蜜蜂均为低毒，对鹌鹑为中等毒性。在田间长期研究表明，在油菜田用量为205 g a.i./hm²时，该药剂对蜜蜂无副作用。

反应信息

• 作为反应物：
  描述：

  氟吡呋喃酮 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以63%的产率得到3-bromo-4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one
  参考文献：
  名称：

  SUBSTITUTED ENAMINOCARBONYL COMPOUNDS

  摘要：

  本发明涉及新型取代烯胺羰基化合物，以及其制备方法和在控制动物害虫，特别是节肢动物，尤其是昆虫方面的用途。

  公开号：

  US20090253749A1
• 作为产物：
  描述：

  N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxamide 在 potassium hydrogensulfate 作用下， 以 丁腈 为溶剂， 反应 5.0h， 以77%的产率得到氟吡呋喃酮
  参考文献：
  名称：

  NOVEL METHOD FOR PRODUCING ENAMINOCARBONYL COMPOUNDS

  摘要：

  本发明涉及一种制备式(I)的烯胺酰基化合物的方法，其中在Brønsted 酸的存在下，式(II)的化合物与之反应，得到式(I)的化合物，其中A、R1和Z在说明书中定义，还涉及用于该发明方法的相应起始化合物。

  公开号：

  US20120016132A1

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。
• [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。
• [EN] INSECTICIDAL METHODS USING NITROGEN-CONTAINING HETEROAROMATIC COMPOUNDS<br/>[FR] PROCÉDÉS INSECTICIDES UTILISANT DES COMPOSÉS HÉTÉROAROMATIQUES CONTENANT DE L'AZOTE
  申请人：BASF SE

  公开号：WO2011064188A1

  公开（公告）日：2011-06-03

  Insectical methods using nitrogen containing heteroaromatic compounds The present invention relates to new insecticidal methods of using nitrogen-containing heteroaromatic compounds of the formula (I), wherein A, E, G, M, W, Y, X, R1 and R2 are defined as in the description, and to their enantiomers, diastereomers and agriculturally and veterinary acceptable salts. The present invention relates to methods of administering and applying such Pyridine compounds of formula I for insecticidal use and purposes in agriculture and in the veterinary field. The invention relates also to new derivatives of Pyridine compounds of formula I.

  使用含氮杂芳化合物的杀虫方法。本发明涉及使用式(I)的含氮杂芳化合物的新杀虫方法，其中A、E、G、M、W、Y、X、R1和R2如描述中所定义，并且其对映异构体、顺反异构体和农业和兽医可接受的盐。本发明涉及用于农业和兽医领域的杀虫用途和目的的给药和应用式I的吡啶化合物的方法。该发明还涉及式I的吡啶化合物的新衍生物。
• [EN] INSECTICIDAL METHODS USING PYRIDINE COMPOUNDS<br/>[FR] PROCÉDÉS INSECTICIDES UTILISANT DES COMPOSÉS À BASE DE PYRIDINE
  申请人：BASF SE

  公开号：WO2011057942A1

  公开（公告）日：2011-05-19

  The present invention relates to new insecticidal methods of using compounds of formula (I) wherein A, E, G, M, Y, X, R1 and R2 are defined as in the description, and to their enantiomers, diastereomers and agriculturally and veterinary acceptable salts. The present invention relates to methods of administering and applying such Pyridine compounds of formula I for insecticidal use and purposes in agriculture and in the veterinary field. The invention relates also to new derivatives of Pyridine compounds of formula (I).

  本发明涉及使用式(I)化合物的新杀虫方法，其中A、E、G、M、Y、X、R1和R2的定义如描述中所述，以及它们的对映体、二对映体和农业和兽医可接受的盐。本发明涉及用于杀虫用途和农业以及兽医领域的目的的给药和应用此类吡啶化合物的方法。该发明还涉及式(I)吡啶化合物的新衍生物。