52570-16-8

• 常用中文名：萘丙胺
• 常用英文名：naproanilide (JMAF only)
• CAS号：52570-16-8
• 分子式：C₁₉H₁₇NO₂
• 分子量：291.344
• 相关类别： 化学农药原药 除草剂 酰胺类除草剂
• 发布时间：2018-09-14 16:36:03
• 更新时间：2024-01-12 19:06:02
• 芳氧链烷酰胺类除草剂。对植物细胞具有很强的生理活性，植物激素类除草剂。药剂一经施于水田，便为土壤表层所吸收。此后，萘氧基丙酰替苯胺即以其本来形式或由土壤中微生物的水解酶或光照所引起的降解产物α-（2-萘氧基）丙酸（NOP）的形式为杂草的根部或球茎所吸收，萘氧基丙酰替苯胺通过杂草中的水解酶降解成NOP，能在最具活性的细胞分裂和生长区破坏正常激素的作用，引起杂草枯萎而死亡。对一年生和多年生杂草如瓜皮草、萤蔺、牛毛毡、水莎草、欧菱、泽泻、水火葱、节节菜、牛繁缕等具有良好的触杀活性。如10%颗粒剂以每公顷30kg在瓜皮草生长2叶期处理，防效90%以上。与杀草丹与去草胺混用，可防除稗草。施药时，田间水层3～5cm为宜。
  该品对多年生和一年生杂草具有触杀作用，如瓜皮草、牛毛毡、水莎草等防效良好。对瓜皮草有特效。  

名称

• 中文名: 萘丙胺
• 英文名: naproanilide
• 中文别名: 拿草胺; 2-(2-萘氧基)丙酰替苯胺
• 英文别名: 2-(2-Naphthyloxy)-N-phenylpropionamide; 2746253; 2-(Naphthalen-2-yloxy)-N-phenylpropanamide; NAPROANILIDE; Propanamide, 2-(2-naphthalenyloxy)-N-phenyl-; uribest; 2-(2-Naphthyloxy)-N-phenylpropanamide; α-(2-Naphthoxy)propionanilide; Urigbest; (RS)-α-2-naphthoxypropionanilide; 2-(2-naphthalenyloxy)-N-phenylpropanamide; rac-(2R)-2-(naphthalen-2-yloxy)-N-phenylpropanamide; naproanilide (JMAF only); mt101; L66J COY1&VMR; NAPROANILIDE STANDARD

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 531.8±33.0 °C at 760 mmHg
• 分子式: C₁₉H₁₇NO₂
• 分子量: 291.344
• 闪点: 275.5±25.4 °C
• 精确质量: 291.125916
• PSA: 38.33000
• LogP: 4.31
• 蒸汽压: 0.0±1.4 mmHg at 25°C
• 折射率: 1.659
• 储存条件:

  密封、在 0-6 ºC下保存

• 稳定性:

  如果遵照规格使用和储存则不会分解，未有已知危险反应

• 计算化学:

  1.疏水参数计算参考值（XlogP）:4.4

  2.氢键供体数量:1

  3.氢键受体数量:2

  4.可旋转化学键数量:4

  5.互变异构体数量:3

  6.拓扑分子极性表面积38.3

  7.重原子数量:22

  8.表面电荷:0

  9.复杂度:364

  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:1

  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：白色结晶，无气味。

  2. 密度（g/mL,25ºC）：1.256

  3. 相对蒸汽密度（g/mL,空气=1）： 未确定

  4. 熔点（ºC）：128

  5. 沸点（ºC）：未确定

  6. 沸点（ºC，13mm hg）：未确定

  7. 折射率：未确定

  8. 闪点（°F）：未确定

  9. 比旋光度（ºC）：未确定

  10. 自燃点或引燃温度（ºC）： 未确定

  11. 蒸气压（kPa,20ºC）：66.6Pa/110℃

  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：不能溶解于水的

毒性和生态

毒理学数据: 雌、雄大鼠急性经口LD50 > 1500mg/kg,雌、雄小鼠> 2000mg/kg;雌、雄大鼠急性经皮LD50 > 3000mg /kg >雌、雄小鼠> 5000mg /kg;雄大鼠腹腔注射LD50 > 2170mg /kg ,雌大鼠> 2800mg /kg，雄小鼠> 1710mg/kg,雌小鼠> 1451 mg /kg。对鱼类无毒性〔也有资料报道鲤鱼LC50 3.4mg/L(48h)，水蚤40mg/L (6h) ] ,糙米中残留量低于0.004mg /kg. 生态学数据: 对水是稍微有危害的不要让未稀释或大量的产品接触地下水、水道或者污水系统，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : TX1486700 CHEMICAL NAME : Propanamide, 2-(2-naphthalenyloxy)-N-phenyl- CAS REGISTRY NUMBER : 52570-16-8 LAST UPDATED : 199612 DATA ITEMS CITED : 18 MOLECULAR FORMULA : C19-H17-N-O2 MOLECULAR WEIGHT : 291.37 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 : 15 gm/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: -,C318,1991 TYPE OF TEST : LC50 - Lethal concentration, 50 percent kill ROUTE OF EXPOSURE : Inhalation SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1670 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: 12,563,1987 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 : 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 - rat DOSE/DURATION : >2710 mg/kg 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: 12,563,1987 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 : 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: 12,563,1987 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2710 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: (39),19,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 20 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 : Administration onto the skin SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3 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 : 1451 mg/kg 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: 12,563,1987 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >15 gm/kg 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: 12,563,1987 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >1451 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: (39),19,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : >12 gm/kg 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: 12,563,1987 ** 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 - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in spleen 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: 12,563,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 21840 mg/kg/13W-C TOXIC EFFECTS : Liver - changes in liver weight Endocrine - changes in spleen weight Blood - changes in spleen 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: 12,563,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 43800 mg/kg/2Y-C TOXIC EFFECTS : Liver - changes in liver weight Blood - changes in spleen 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: 12,563,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 18250 mg/kg/2Y-C TOXIC EFFECTS : Endocrine - changes in thymus weight Endocrine - changes in thyroid weight Blood - other changes 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: 12,563,1987 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 16 gm/kg SEX/DURATION : female 6-15 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - other effects 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: 12,563,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 10400 mg/kg SEX/DURATION : female 6-18 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) 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: 12,563,1987

安全

• 海关编码: 2924299015

合成路线

42308-20-3 135-19-3 ~% 52570-16-8

文献：Yu, Jianzhong; Wang, Yongtao; Zhang, Peizhi; Wu, Jun Synlett, 2013 , vol. 24, # 11 art. no. ST-2013-W0237-L, p. 1448 - 1454

上下游产品

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制备

制备方法一
α-溴代丙酰替苯胺的制备 将12.3g三氯氧磷在搅拌下逐渐滴加到36.7g (0.24mol)的α-溴丙酸中，控制温度40℃以下，滴毕再逐渐滴加苯胺18.6g (0.2mol)，升温，于110～120℃搅拌反应1.5h。冷却至80℃，加入少量水。抽滤、水洗，于50～60℃干燥，得粗品54.4～58g。经重结晶、脱色，得纯品40.1～41.3g。m.p.96～97.5℃，收率88%～90%。
萘丙胺的制备 将8.9g β-萘酸（0.06mol)和24g 10%NaOH （0.06mol)加热溶解。再加适应症相转移催化剂氯化三乙基苄基铵0.4g。另将11.4g (0.05mol)α-溴丙酰替苯胺溶于100mL苯中，滴加到β-萘酚氢氧化钠溶液中。同时用水浴加热，于浴温60～70℃、1.5～2h内加完，再保温反应4h。冷却，分层，水层用苯提取，合并油层。常压脱苯，冷却后得粗品16～17.5g，重结晶后得纯品10.5～10.9g，熔点127～128℃，收率72.1%～74.9%。
也可采用光气而不用POCl3制备。先将光气与α-氯丙酸作用生成酰氯化物；用苯胺处理酰氯化物，生成α-氯丙酰苯胺；除去气态副产物，加入β-萘酚，反应毕冷却，其中产物以晶体形式析出。本法优点：所有副产物均为气体，简化了操作；以甲苯为溶剂，使第二步、第三步反应合为一步，不必对中间产物进行过滤；以甲苯为溶剂可有效防止α-氯丙酸的分解，提高了原料利用率。
制备方法二
α-氯代丙酸与β-萘酚作用，生成2-（2-萘氧基）丙酸，然后用光气或PCl3氯化生成α-（2-萘氧基）丙酰氯，最后与苯胺反应制得萘丙胺。

海关

海关编码	2924299015
中文概述	2924299015 萘丙胺、牧草胺、溴丁酰草胺。监管条件:S(进出口农药登记证明)。增值税率:17.0%。退税率:9.0%。最低关税:6.5%。普通关税:30.0%
Summary	2924299015 2-bromo-3,3-dimethyl-n-(2-phenylpropan-2-yl)butanamide。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:30.0%