80844-07-1

• 常用中文名：依芬普司
• 常用英文名：Etofenprox
• CAS号：80844-07-1
• 分子式：C₂₅H₂₈O₃
• 分子量：376.488
• 相关类别： 化学农药原药 杀虫剂 拟除虫菊脂杀虫剂
• 发布时间：2018-09-06 11:09:21
• 更新时间：2024-01-02 18:16:13
• 依托芬普利是一种非酯类拟除虫菊酯杀虫剂。依托芬普利对家蝇有毒性(半数致死量=23ng/只)。含有依托芬普利的制剂已用于防治农业害虫。

名称

• 中文名: 醚菊酯
• 英文名: etofenprox
• 中文别名: 多来宝; 依芬普司
• 英文别名: TREBON; mti500; ETOPHENPROX; Lenatop; MFCD00210287; 1-{[2-(4-Ethoxyphenyl)-2-methylpropoxy]methyl}-3-phenoxybenzene; 1-[[2-(4-ethoxyphenyl)-2-methylpropoxy]methyl]-3-phenoxybenzene; a-((p-ethoxy-b,b-dimethylphenethyl)oxy)-m-phenoxytoluene; Ethophenprox; PEPE; Etofenprox; NUKIL; Ethofenprox; PUNKASO; 1-((2-(4-Ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxybenzene; EINECS 407-980-2; VECTRON; Benzene, 1-[[2-(4-ethoxyphenyl)-2-methylpropoxy]methyl]-3-phenoxy-; 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 481.6±40.0 °C at 760 mmHg
• 熔点: 36ºC
• 分子式: C₂₅H₂₈O₃
• 分子量: 376.488
• 闪点: 165.1±24.6 °C
• 精确质量: 376.203857
• PSA: 27.69000
• LogP: 7.34
• 外观性状: 固体
• 蒸汽压: 0.0±1.2 mmHg at 25°C
• 折射率: 1.559
• 储存条件:

  库房通风低温干燥0-6°C

• 稳定性:

  化学性质稳定，于80℃贮存90d未见明显分解，在pH值2.8～11.9土壤中半衰期约6d。工业品溶点34～35℃。

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:0

  3.氢键受体数量:3

  4.可旋转化学键数量:9

  5.互变异构体数量:无

  6.拓扑分子极性表面积27.7

  7.重原子数量:28

  8.表面电荷:0

  9.复杂度:422

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：白色晶体

  2. 密度（g/mL25 ºC）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：.157(23℃)。

  4. 熔点（ºC）：36.4～38

  5. 沸点（ºC）：208（719.8Pa）、100（3.2×10-2Pa）

  6. 沸点（ºC1mmHg）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（Pa）：32×10^-3 (100℃)、8.0×10^-3 (25℃)，

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（正辛醇/水）分配系数的对数值：11200000

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下（%,V/V）：未确定

  19. 溶解性：氯仿858g/L、丙酮908g/L、醋酸乙酯875g/L、乙醇150g/L、甲醇76.6g/L、二甲苯84.8g/L、水1mg/L

生物活性

• 描述: 依托芬普利是一种非酯类拟除虫菊酯杀虫剂。依托芬普利对家蝇有毒性(半数致死量=23ng/只)。含有依托芬普利的制剂已用于防治农业害虫。
• 相关类别:
  信号通路 >> 其他 >> 其他

毒性和生态

毒理学数据: 口服- 大鼠 LD50: 42800 毫克 / 公斤; 口服- 小鼠 LD50: 107000 毫克/ 公斤 狗>5000mg/kg,LD50 > 1072mg /kg ,雌性>2140mg/kg;雄性小鼠急性经皮LD50 > 1072mg/kg, CHEMICAL IDENTIFICATION RTECS NUMBER : DA0670000 CHEMICAL NAME : Benzene, 1-((2-(4-ethoxyphenyl)-2-methylpropoxy)methyl)-3-phen oxy- CAS REGISTRY NUMBER : 80844-07-1 LAST UPDATED : 199701 DATA ITEMS CITED : 18 MOLECULAR FORMULA : C25-H28-O3 MOLECULAR WEIGHT : 376.53 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 : >42800 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LC50 - Lethal concentration, 50 percent kill ROUTE OF EXPOSURE : Inhalation SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >5900 mg/m3/4H TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,505,1989 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2140 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >42880 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >32160 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >107 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >2140 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >13400 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >53600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >5 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Bird - duck DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (48),23,1986 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 10920 mg/kg/13W-C TOXIC EFFECTS : Liver - fatty liver degeneration Liver - changes in liver weight Endocrine - changes in adrenal weight REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 226 gm/kg/2Y-C TOXIC EFFECTS : Liver - fatty liver degeneration Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 180 gm/kg/13W-I TOXIC EFFECTS : Liver - changes in liver weight Kidney, Ureter, Bladder - other changes Related to Chronic Data - death REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 445 gm/kg/2Y-C TOXIC EFFECTS : Liver - changes in liver weight Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Related to Chronic Data - death REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 124 gm/kg/1Y-C TOXIC EFFECTS : Liver - fatty liver degeneration Liver - changes in liver weight Blood - normocytic anemia REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 3250 mg/kg SEX/DURATION : female 6-18 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - other effects Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 14,505,1989

安全

• 符号: GHS09
• 信号词: Warning
• 危害声明: H362-H410
• 警示性声明: P201-P260-P263-P273-P308 + P313-P391
• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): Xn
• 危险品运输编码: UN 3077 9 / PGIII
• RTECS号: DA0670000

合成路线

51632-16-7 83493-63-4 ~93% 80844-07-1

文献：Galin, F. Z.; Rakhimov, R. G.; Tolstikov, G. A. Russian Journal of Organic Chemistry, 1993 , vol. 29, # 1.2 p. 170 Zhurnal Organicheskoi Khimii, 1993 , vol. 29, # 168 p. 202 - 203

13826-35-2 83493-80-5 ~43% 80844-07-1 80854-21-3

文献：Russian Journal of Organic Chemistry, , vol. 38, # 11 p. 1629 - 1634

515-40-2 ~% 80844-07-1

文献：Russian Journal of Organic Chemistry, , vol. 38, # 11 p. 1629 - 1634

99359-77-0 ~% 80844-07-1

文献：Russian Journal of Organic Chemistry, , vol. 38, # 11 p. 1629 - 1634

103-73-1 ~% 80844-07-1

文献：Russian Journal of Organic Chemistry, , vol. 38, # 11 p. 1629 - 1634

71-43-2 ~% 80844-07-1

文献：Russian Journal of Organic Chemistry, , vol. 38, # 11 p. 1629 - 1634

上下游产品

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制备

制备方法一

异丁酰氯的制备 359.5g异丁酸在室温下（15℃）滴加595g亚硫酰氯，滴毕后升温至75℃，至无氯化氢放出止，收集88～92℃馏分，得293.0g产品。残留物中加入前馏分和新亚硫酰氯100g，常压蒸馏得83～86℃馏分232.3g，88～92℃产品106.1g，共得产品399.1g，含量98.75%，收率91.7%。

1-（4-乙氧基苯基）-2-甲基-1-丙酮的制备将37g苯乙醚与50mL二硫化碳混合，冷却下分批加入无水三氯化铝48g，继续冷却至2～3℃，滴加异丁酰氯32.1g，滴毕再搅拌反应1h。反应液倒入200mL冰水，搅拌下加100mL浓盐酸，分出油层。水层用苯50mL提取3次，苯提取液与油层合并，干燥、脱苯、真空蒸馏得产品2.5g，收率74.4%。

1-(4-乙氧基苯基）-2-溴-2-甲基-1-丙酮的制备将上步产物42g与95mL无水乙醚于20℃、1.5h内滴加8g溴，滴毕继续反应30min，慢慢加入100mL水，搅拌静置分层。醚层经水洗、30%亚硫酸氢钠溶液洗涤，再水洗，干燥，脱醚得白色结晶43g，m.p.36～38℃。

2-（4-乙氧基苯基）-2-甲基丙酸的制备 将上步产物239g、甲醇120mL、原甲酸三乙酯478mL、甲磺酸16mL于60℃保温反应12h，搅拌下加15%氢氧化钠800mL至pH值12，加热回流3h。倾入大烧杯中，加2500mL水、250mLCCl4，静置分层，水层中加浓盐酸250mL，过滤，真空干燥得124g产品，m.p.81～83℃，收率67.7%。

2-(4-乙氧基苯基）-2-甲基丙醇的制备 将上步产物83.5g和500mL乙醚在无水条件下慢慢滴入到450mL乙醚和17g氢化铝锂混合液中，滴毕，于室温下搅拌2h，再滴入乙酸乙酯。滴毕继续反应15min，滴加4mol/L硫酸250mL，分层，醚层用10%氢氧化钠洗涤后再水洗、干燥、放置、脱醚，得产品75g。

醚菊酯的合成将上步产物172g、间苯氧基苄氯207.5g，在氢氧化钠存在下，以四正丁基溴化铵（28.7g)为相转移催化剂，于80℃反应4h，降温后加入390mL水，搅拌20min，甲苯萃取，水洗萃取液，干燥、脱溶、减压蒸馏，收集226～255℃/399.9～633Pa馏分211.5g，含量95.4%，收率63.4%。

制备方法二

对乙氧基苯乙腈在氢氧化钾、水、溴化三甲基苄铵存在下与碘甲烷反应，生成物经水解，然后用氢化铝锂还原，最后在氢化钠和乙腈存在下，与间苯氧基氯苄反应，合成醚菊酯。

制备方法三

叔丁基乙酰苯酯的制备对叔丁基酚（0.67mol)与醋酐（0.8mol)作用，于140℃回流反应4h，脱去副产乙酸和未反应的醋酐，得棕黄色液体，收率95%，含量91.2%。

[4-(2-氯-1，1-二甲基乙基）苯基]乙酸酯的制备将上步产物100g(含量91.2%)与四氯化碳200mL混合物，加热至60℃。加2g偶氮二异丁腈，同时通氯，加流，于1h内通入氯气15g。分析，脱溶得棕红色液体107g，再减压蒸馏，得产品45g，收率89%，含量93.2%。

1-氯-2-（4-乙氧基苯基）-2-甲基丙烷的制备将上步产物100g（含量94%、0.415mol)、硫酸二乙酯160g (1.04mol)、片状氢氧化钾85g（含量82%、1.245mol)混合，搅拌，加热至30℃滴加20%苄基三乙基氯化铵24g（0.0208mol)，约10min加完，滴毕升温至40℃，剧烈搅拌反应6h。冷却，加水100mL，搅拌使固体溶解，分层，有机层用水洗涤，减压脱尽低沸物，得黄色液体产物88.5g，含量89.6%，收率89.9%。

醚菊酯的合成将上步产物50g (含量90%、0.21mol)、间苯氧基苯甲醇51.4g(含量98%、0.252mol)、片状氢氧化钾21.5g(含量82%、0.315mol)、二甲基亚砜250mL混合后，在氮气保护下加热至120℃保温10h，减压脱溶，于残液中加入100mL水、100mL苯，搅拌分层，苯层水洗，减压脱苯，得棕黑色黏稠液体94g，高真空蒸馏得醚菊酯49.4g，含量85.6%，收率53.5%。