27355-22-2

• 常用中文名：四氯苯酞
• 常用英文名：fthalide
• CAS号：27355-22-2
• 分子式：C₈H₂Cl₄O₂
• 分子量：271.912
• 相关类别： 化学农药原药 杀菌剂 其他杀菌剂
• 发布时间：2018-07-17 12:10:48
• 更新时间：2024-01-08 12:02:25
• 为一种防治稻瘟病的保护性杀菌剂。病菌侵入稻株之前施药，能有效地抑制附着于稻株表面的孢子形成，阻止菌丝侵入，因此有良好的防治效果，但若稻瘟病菌侵入稻株后施药，不能阻止孢子发芽或菌丝生长。如防治穗颈瘟，在水稻破口期进行首次喷药，用50%可湿性粉剂15g/100m²对水喷雾，在水稻齐穗期或第1次喷药后7d，进行第2次喷药，残效期达13d。如防治叶瘟，于田间见病斑时喷药，用50%可湿性粉剂15g/100m²对水喷雾，若病情仍在发展，5～7d后再喷1次，防治效果70%～90%。 
  

名称

• 中文名: 四氯苯酞
• 英文名: 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one
• 中文别名: 氯百杀; 热必斯; 稻瘟酞
• 英文别名: 4,5,6,7-TETRACHLORO-PHTHALIDE; Rabcide; 1(3H)-4,5,6,7-tetrachloroisobenzofuranone; EINECS 229-405-2; fthalide; Phthalide,4,5,6,7-tetrachloro; 4,5,6,7-Tetrachloro-1(3H)-isobenzofuranone (9CI); phthalide; 1(3H)-Isobenzofuranone, 4,5,6,7-tetrachloro-; 4,5,6,7-Tetrachloro-2-benzofuran-1(3H)-one; KF-32; PHH; 4,5,6,7-tetrachloroisobenzofuran-1(3H)-one; 4,5,6,7-tetrachloro-1(3H)-isobenzofuranone; 4,5,6,7-tetrachloro-3H-2-benzofuran-1-one; 4,5,6,7-Tetrachlor-phthalid

物化性质

• 密度: 1.8±0.1 g/cm3
• 沸点: 464.4±45.0 °C at 760 mmHg
• 熔点: 209-210ºC
• 分子式: C₈H₂Cl₄O₂
• 分子量: 271.912
• 闪点: 215.8±27.7 °C
• 精确质量: 269.880890
• PSA: 26.30000
• LogP: 2.73
• 蒸汽压: 0.0±1.1 mmHg at 25°C
• 折射率: 1.636
• 储存条件:

  0-6℃

• 稳定性:

  避免接触强氧化剂，强碱

  在试验剂量内，未发现致癌、致畸、致突变作用。对兔皮肤和眼睛无刺激作用。

• 分子结构:

  1、 摩尔折射率：355.13

  2、 摩尔体积（cm³/mol）：153.8

  3、 等张比容（90.2K）：426.4

  4、 表面张力（dyne/cm）：59.0

  5、 极化率（10^-24cm³）：21.85

• 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:2

  4.可旋转化学键数量:0

  5.互变异构体数量:无

  6.拓扑分子极性表面积26.3

  7.重原子数量:14

  8.表面电荷:0

  9.复杂度:260

  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/mL,25/4℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：209～210

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：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（kPa,25ºC）：未确定

  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（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：未确定

毒性和生态

毒理学数据: 对大、小鼠急性经口LD50> 10000mg/kg，急性经皮LD50 > 10000mg /kg 。急性无作用剂量每天2000mg /kg ,最大安全浓度为2000mg /kg ,最小中毒浓度为10000mg /kg。鲤鱼LC50 > 135mg/L (320mg/L) (48h)。对鸟低毒，对蜜蜂、家蚕低毒。 CHEMICAL IDENTIFICATION RTECS NUMBER : TI3870000 CHEMICAL NAME : Phthalide, 4,5,6,7-tetrachloro- CAS REGISTRY NUMBER : 27355-22-2 BEILSTEIN REFERENCE NO. : 0182477 LAST UPDATED : 199612 DATA ITEMS CITED : 13 MOLECULAR FORMULA : C8-H2-Cl4-O2 MOLECULAR WEIGHT : 271.90 WISWESSER LINE NOTATION : T56 BVO DHJ FG GG HG IG 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 : 20 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ARAE "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revision Volume(issue)/page/year: 4,73,1976/1977 TYPE OF TEST : LC - Lethal concentration ROUTE OF EXPOSURE : Inhalation SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >4100 mg/m3 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: 15,311,1990 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 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: (36),32,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 9780 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: (36),32,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 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: (36),32,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 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: (36),32,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 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: (40),32,1982 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 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: (36),32,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 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: (36),32,1979 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 273 gm/kg/13W-C TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain 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: 15,311,1990 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2190 gm/kg/2Y-C TOXIC EFFECTS : Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases 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: 15,311,1990 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 546 gm/kg/13W-C TOXIC EFFECTS : Liver - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) 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: 15,311,1990 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4380 gm/kg/2Y-C TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases 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: 15,311,1990

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): R36/37/38:Irritating to eyes, respiratory system and skin .
• 安全声明 (欧洲): S26-S36-S24/25
• WGK德国: 3
• 海关编码: 2932209013

合成路线

117-08-8 ~87% 27355-22-2

文献：Narasimhan, Srinivasan Heterocycles, 1982 , vol. 18, p. 131 - 135

85-44-9 ~% 27355-22-2

文献：Graebe Justus Liebigs Annalen der Chemie, 1887 , vol. 238, p. 326,327 Chemische Berichte, 1883 , vol. 16, p. 861

109-99-9 117-08-8 ~% 27355-22-2

文献：Parrini Gazzetta Chimica Italiana, 1957 , vol. 87, p. 1147,1156

60-29-7 117-08-8 ~% 27355-22-2

文献：Parrini Gazzetta Chimica Italiana, 1957 , vol. 87, p. 1147,1156

117-08-8 64-19-7 ~% 27355-22-2

文献：Graebe Justus Liebigs Annalen der Chemie, 1887 , vol. 238, p. 326,327 Chemische Berichte, 1883 , vol. 16, p. 861

上下游产品

上游产品  5
117-08-8 85-44-9 109-99-9 60-29-7
64-19-7
下游产品  0

制备

苯环氯化 以四氯化碳为溶剂（3320g)，在催化剂存在下，加入邻二甲苯223g(2mol)，混合后通氯反应，控制在60℃以下，反应3h，析出白色结晶；升温至70℃，继续通氯至大部分结晶溶解。
侧链氯化 苯环氯化结束后，稍冷，取出铁催化剂加入三氯化磷20g，在高压汞灯光照下通氯，（也可在偶氮二异丁腈和三氯化磷存在下侧链氯化）于70℃反应7h，蒸出四氯公碳，得产品780g左右。
四氯苯酞的合成 将100g3,4,5,6-α,α,α',α'-八氯邻二甲苯和900g95%的硫酸搅拌混合后，升混至130～140℃，保温5h，至无氯化氢气体逸出，冷至室温，再缓缓倒入冰水中，析出淡黄色结晶，抽滤，水洗、干燥后得四氯苯酞70g左右

制备方法二

海关

海关编码	2932209013
中文概述	2932209013 蝇毒磷,茴蒿素,溴敌隆,呋酰胺等〔包括四氯苯酞,畜虫磷〕。监管条件:S(进出口农药登记证明)。增值税率:17.0%。退税率:0.0%。最低关税:6.5%。普通关税:20.0%
Summary	2932209013 4,5,6,7-tetrachloroisobenzofuran-1(3h)-one。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:0.0%。MFN tarrif:6.5%。general tariff:20.0%