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噻菌灵

噻菌灵用途

Thiabendazole能抑制蠕虫特异的富马酸还原酶，具有驱虫特性。

噻菌灵名称

[ CAS 号 ]:
148-79-8

[ 中文名 ]:
噻菌灵

[ 英文名 ]:
Thiabendazole

[中文别名 ]:

[英文别名 ]:

Arbotect
Tresaderm
2-(thiazol-4-yl)benzimidazole
Mintezol
2-(4-Thiazolyl)benzimidazole,Thiabendazole
2-(4-thiazolyl)-1H-benzimidazole
TBZ
Benzimidazole, 2-(4-thiazolyl)-
2-(4-Thiazolyl)benzimidazole
4-(1H-Benzo[d]imidazol-2-yl)thiazole

噻菌灵生物活性

[ 描述 ]:

Thiabendazole能抑制蠕虫特异的富马酸还原酶,具有驱虫特性。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 线粒体代谢

研究领域 >> 感染

[参考文献]

[1]. Cha, H.J., et al., Evolutionarily repurposed networks reveal the well-known antifungal drug thiabendazole to be a novel vascular disrupting agent. PLoS Biol, 2012. 10(8): p. e1001379.

[2]. Zhang, J., et al., Thiabendazole, a well-known antifungal drug, exhibits anti-metastatic melanoma B16F10 activity via inhibiting VEGF expression and inducing apoptosis. Pharmazie, 2013. 68(12): p. 962-8.

[相关活性小分子]

噻菌灵物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
446.0±37.0 °C at 760 mmHg

[ 熔点 ]:
298-301ºC

[ 分子式 ]:
C₁₀H₇N₃S

[ 分子量 ]:
201.248

[ 闪点 ]:
226.2±16.9 °C

[ 精确质量 ]:
201.036072

[ PSA ]:
69.81000

[ LogP ]:
2.47

[ 外观性状 ]:
淡黄色粉末

[ 蒸汽压 ]:
0.0±1.1 mmHg at 25°C

[ 折射率 ]:
1.740

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开储运

[ 水溶解性 ]:
0.005 g/100 mL

噻菌灵MSDS

噻菌灵毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE0700000

CHEMICAL NAME :: Benzimidazole, 2-(4-thiazolyl)-

CAS REGISTRY NUMBER :: 148-79-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 46

MOLECULAR FORMULA :: C10-H7-N3-S

MOLECULAR WEIGHT :: 201.26

WISWESSER LINE NOTATION :: T56 BM DNJ C- ET5N CSJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 47619 ug/kg/1D-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2080 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3850 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 4 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 400 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22200 mg/kg/60D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13650 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - other changes Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36 gm/kg/26W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 24 gm/kg/30D

TOXIC EFFECTS :: Behavioral - general anesthetic Behavioral - food intake (animal) Behavioral - ataxia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg/7D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 gm/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 175 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1250 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10080 mg/kg

SEX/DURATION :: male 6 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2368 mg/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5336 mg/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - skin and skin appendages

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 250 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11700 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 60 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2400 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 7800 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 50 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 287,29,1993 *** REVIEWS *** TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 32,151,1975 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 72430 No. of Facilities: 183 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 1746 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 72430 No. of Facilities: 193 (estimated) No. of Industries: 3 No. of Occupations: 12 No. of Employees: 5960 (estimated) No. of Female Employees: 1184 (estimated)

噻菌灵安全信息

[ 符号 ]:

GHS09

[ 信号词 ]:
Warning

[ 危害声明 ]:
H410

[ 警示性声明 ]:
P273-P501

[ 个人防护装备 ]:
Eyeshields;Gloves

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

[ 风险声明 (欧洲) ]:
R50/53

[ 安全声明 (欧洲) ]:
S60-S61

[ 危险品运输编码 ]:
UN 3077

[ WGK德国 ]:
2

[ RTECS号 ]:
DE0700000

[ 包装等级 ]:
III

[ 危险类别 ]:
9

[ 海关编码 ]:
2934100015

噻菌灵合成路线

噻菌灵上下游产品

噻菌灵上游产品

噻菌灵下游产品

噻菌灵制备

1. 噻唑-4-羧酰溴和邻苯二胺混合，加入多磷酸，搅拌下加热至240℃，保温3h。将热反应液注入冰中，过滤，滤液用30%氢氧化钠溶液洗涤，约pH6时析出2-（4'-噻唑基）-苯并咪唑沉淀，过滤，水洗，干燥，得熔点296-298℃的结晶体。用沸乙醇重结晶，熔点301-302℃。另一种工艺是将4-乙氧甲酰噻唑、邻苯二胺、多磷酸的混合物搅拌加热至125℃，然后在175℃加热2h，将混合物注入冰水中，用氢氧化钠溶液中和至pH6，析出结晶，过滤，用热丙酮萃取，萃取物用活性炭脱色后，浓缩，真空干燥，得噻菌灵。

2. 由4-噻唑羧基酰胺与邻苯二胺在缩合磷酸中反应而得。

3. 制备方法一
4-乙氧甲酰噻唑的制备以酒石酸为原料，经裂解得丙酮酸，再通过酯化、溴化后，与硫代甲酰胺环合制得。
噻菌灵的合成将4-乙氧甲酰噻唑、邻苯二胺、多磷酸的混合物搅拌加热至125℃，然后在175℃加热2h，将混合物注入冰水中，用氢氧化钠溶液中和至pH值6，析出结晶，过滤，用热丙酮萃取，萃取物用活性炭脱色后，浓缩，真空干燥，制得噻菌灵。
制备方法二
噻唑-4-羟酰溴和邻苯二胺混合，加入多磷酸，搅拌下加热至240℃，保温3h。将热反应液注入冰水中，过滤，滤液用30%氢氧化钠溶液洗涤，约pH值为6析出2-（4'-噻唑基）-苯并咪唑沉淀，过滤，水洗，干燥，得噻菌灵。用沸乙醇重结晶，m.p.301～302℃。

4. 方法一
在175℃下由4-乙氧基甲酰噻唑与邻苯二胺在缩合磷酸中反应2h。反应物倾入冰水中，用氢氧化钠中和至Ph值6，析出结晶，过滤后用丙酮重结晶、活性炭脱色。脱色液经浓缩、真空干燥得成品。
方法二
在240℃下由4-噻唑羧基酰氨(或酰溴)与邻苯二胺在缩合磷酸中反应3h，反应物倾人冰水中，过滤后滤液用30%的氢氧化钠溶液洗涤至Ph=6，苯并咪唑结晶析出，经过滤、水洗、干燥得粗品，再经乙醇重结晶得成品。

噻菌灵海关

[ 海关编码 ]: 2934100015

[ 中文概述 ]:
2934100015 噻菌灵,噻菌胺,噻丙腈。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:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ 监管条件 ]: S.进出口农药登记证明

[ Summary ]:
2934100015 2,4-dimethyl-n-phenylthiazole-5-carboxamide。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

噻菌灵文献

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Pen-on-paper approach toward the design of universal surface enhanced Raman scattering substrates.

Small 10(15) , 3065-71, (2014)

The translation of a technology from the laboratory into the real world should meet the demand of economic viability and operational simplicity. Inspired by recent advances in conductive ink pens for ...

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噻菌灵