氟氯氰菊酯

氟氯氰菊酯用途

Cyfluthrin 是一种 II 型拟除虫菊酯 (pyrethroid),对多种昆虫都有作用。Cyfluthrin 是通过重复刺激来调节 Nav1.8 钠通道。Cyfluthrin 可应用于农业、兽医、杀虫剂、拟除虫菊酯和贮存产品等领域。

氟氯氰菊酯名称

[ CAS 号 ]:
68359-37-5

[ 中文名 ]:
氟氯氰菊酯

[ 英文名 ]:
cis-Cyfluthrin

[中文别名 ]:

[英文别名 ]:

CYFLUTHRIN, (1R,3R,αR)-
Cyfluthrin
Tempo 2
Cyfluthrine
BAY-VI 1704
(1R,3R,αR)-Cyfluthrin
BAY FCR 1272
EINECS 269-855-7
Baythroid H
(RS)-α-cyano-4-fluoro-3-phenoxybenzyl (1RS,3RS

氟氯氰菊酯生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 跨膜转运 >> 钠通道

研究领域 >> 感染

[体外研究]

氟氯氰菊酯(0-50μM；24小时)对SH-SY5Y细胞的IC50和IC30分别为19.39μM和4.81μM[1]。

[参考文献]

[1]. Jin-Sung Choi,et al.Structure-activity Relationships for the Action of 11 Pyrethroid Insecticides on Rat Na v 1.8 Sodium Channels Expressed in Xenopus Oocytes.Toxicol Appl Pharmacol. 2006 Mar 15;211(3):233-44

[2]. María-Aránzazu Martínez, et al. Oxidative Stress and Related Gene Expression Effects of Cyfluthrin in Human Neuroblastoma SH-SY5Y Cells: Protective Effect of Melatonin. Environ Res. 2019 Oct;177:108579.

氟氯氰菊酯物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
496.3±45.0 °C at 760 mmHg

[ 熔点 ]:
60ºC

[ 分子式 ]:
C₂₂H₁₈Cl₂FNO₃

[ 分子量 ]:
434.288

[ 闪点 ]:
253.9±28.7 °C

[ 精确质量 ]:
433.064789

[ PSA ]:
59.32000

[ LogP ]:
6.29

[ 外观性状 ]:
一种粘性琥珀色部分结晶油状

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.611

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开储运

氟氯氰菊酯MSDS

详细MSDS(安全技术说明书)

氟氯氰菊酯毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GZ1253000

CHEMICAL NAME :: Cyclopropanecarboxylic acid, 2-(2,2-dichlorovinyl)-3,3-dimethyl-, ester with (4-fluoro-3- phenoxyphenyl)hydroxyacetonitrile

CAS REGISTRY NUMBER :: 68359-37-5

LAST UPDATED :: 199710

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C22-H18-Cl2-F-N-O3

MOLECULAR WEIGHT :: 434.31

WISWESSER LINE NOTATION :: L3TJ A1 A1 B1UYGG CVOYCN&R DF COR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C39,1991

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 469 gm/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,432,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - food intake (animal) Behavioral - muscle contraction or spasticity

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0555484

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 69993 ug/kg/21D-I

TOXIC EFFECTS :: Endocrine - hypoglycemia Blood - pigmented or nucleated red blood cells Nutritional and Gross Metabolic - changes in chlorine

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 7,367,1987

氟氯氰菊酯安全信息

[ 符号 ]:

GHS06, GHS09

[ 信号词 ]:
Danger

[ 危害声明 ]:
H300-H331-H410

[ 警示性声明 ]:
P261-P264-P273-P301 + P310-P311-P501

[ 个人防护装备 ]:
Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
T:Toxic;N:Dangerousfortheenvironment;

[ 风险声明 (欧洲) ]:
R26/28;R50/53

[ 安全声明 (欧洲) ]:
S1/2-S36/37/39-S45-S60-S61

[ 危险品运输编码 ]:
UN 2588

[ RTECS号 ]:
GZ1253000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

[ 海关编码 ]:
29269090

氟氯氰菊酯上下游产品

氟氯氰菊酯上游产品

氟氯氰菊酯下游产品

氟氯氰菊酯制备

以对氯甲苯为原料

以苯胺为原料

3-（2,2-二氯乙烯基）-2，2-二甲基环丙烷羧酰氯的制备二氯菊酸的合成可以采用相模法、Farkas法、相模、库拉莱法、环丁酮法、NRDC法等。可以根据不同需要选用。
相模法（Sagami法）用3-甲基-2-丁烯醇与原乙酸酯在催化剂磷酸存在下，于140～160℃进行缩合，脱去一分子醇，并进行Claisen重排，生成3，3-二甲基-戊烯酸甲酯（贲亭酸甲酯），再与四氯化碳在过氧化物存在下反应生成3，3-二甲基-4，6，6，6-四氯己烯酸甲酯，然后在甲醇钠存在下脱氯化氢，环合成生二氯菊酸甲酯。

Farkas法用1，1-二氯-4-甲基-1，3-戊二烯与重氮乙酸酯在铜粉或其他催化剂存在下反应，生成二氯菊酸。
1,1-二氯-4-甲基-1，3-戊二烯可采用三氯乙醛与异丁烯作用，反应生成物为1，1，1-三氯-4-甲基-3-戊烯-2-醇和1，1，1-三氯-4-甲基-4-戊烯-2-醇。如果以AlCl3为催化剂，产物以前者为主。再与醋酐作用经乙酰化、锌粉还原、对甲基苯磺酸催化异构化得含共轭双键的1，1-二氯-4-甲基-1，3-戊二烯。
相模-库拉莱法（Sagami-Kuraray法）这是相模法与Farkas法的结合。

环丁酮法利用α-卤代环丁酮在碱性物质存在下发生Favorskii重排，从而环缩小成生顺式二氯菊酸。α-氯代环丁酮以异丁烯、四氯化碳、丙烯酸为原料制得。

用环丁酮法生产二卤菊酸，顺式的比例达80% ～90%。
NRDC法利用Wittig试剂与相应的菊酸甲醛衍生物反应，得到所需要的菊酸类衍生物。用这种方法可以保持原菊酸类化合物的构型不变。

二氯菊酸与氯化亚砜作用，得二氯菊酸氯。

氟氯氰菊酯的合成将6.8g 3-(2,2-二氯乙烯）-2，2-二甲基环丙羧酰氯和6.5g4-氟-3-苯氧基苯甲醛，在20～25℃滴加到2.25g氰化钠、3.5mL水和150mL正己烷及0.75g四丁基溴化铵的混合物中。然后，反应混合物在20～25℃搅拌4h，用800mL甲苯稀释，并用800mL水分2次洗涤有机相用硫酸镁干燥，减压脱溶，残余的溶剂在60℃/133.3Pa下蒸馏除去，得10.8g氟氯氰菊酯的黏稠油状物，收率76%。
也可将3-苯氧基-4-氟苯甲醛用亚硫酸氢钠变成相应的磺酸盐，然后再与氰化钠及3-（2,2-二氯乙烯基）-2，2-二甲基环丙烷羧酰氯反应，制得氟氯氰菊酯，收率95%。

氟氯氰菊酯文献

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