甲基1H-苯并咪唑-2-基氨基甲酸酯 | 162976-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 甲基1H-苯并咪唑-2-基氨基甲酸酯
• 英文名称: 1H-benzimidazol-2-ylcarbamic acid methyl ester
• 英文别名: carbendazim；bavistin；methyl 2-benzimidazolecarbamate；CBZ；methyl N-(1,3-dihydrobenzimidazol-2-ylidene)carbamate
• CAS: 162976-69-4
• 化学式: C₉H₉N₃O₂
• mdl: MFCD00055390
• 分子量: 191.189
• InChiKey: TWFZGCMQGLPBSX-UHFFFAOYSA-N

物化性质

• 沸点：
  318.0±25.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)
• 物理描述：
  Carbendazim appears as light gray or beige powder. (NTP, 1992)
• 颜色/状态：
  White powder
• 气味：
  Odorless /Technical/
• 熔点：
  Decomposes at 300 °C
• 溶解度：
  Solubility in water at 24 °C: 29 mg/L at pH 4; 8 mg/L at pH 7; 1.49 mg/L at pH 8
• 蒸汽压力：
  7.5X10-10 mm Hg at 20 °C
• 稳定性/保质期：

  ... Stable for at least 2 yr below 50 °C. Stable after 7 days at 20,000 lux. ... Stable in acids, forming water-soluble salts.

• 分解：
  Slowly decomposed in alkaline soln (22 °C): DT50 >350 days (pH 5 and pH 7), 124 days (pH 9).
• 解离常数：
  pKa = 4.29
• 碰撞截面：
  134.94 Ų [M+H]+ [CCS Type: TW]

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

容易被植物吸收。一个降解产物是2-氨基苯并咪唑。

Readily absorbed by plants. One degradation product is 2-aminobenzimidazole.

来源:Hazardous Substances Data Bank (HSDB)

代谢

两个代谢物：甲基-5-羟基-2-苯并咪唑甲酸酯（5-HBC）和2-氨基苯并咪唑（2-AB）在大鼠静脉注射12 mg/kg后非常迅速形成。它们的峰值浓度在肝脏和肾脏出现在静脉注射后的15分钟。未改变的咪鲜胺在血液中的浓度最高。5-HBC在器官中占主导地位。2-AB仅以少量存在。口服给药14C-咪鲜胺（12 mg/kg）的生物利用度大约为85%。放射性物质在亚细胞组分中的分布不均匀，其在细胞溶胶中的浓度最高，在微粒体中的浓度最低。

... Two metabolites: methyl 5-hydroxy-2-benzimidazolecarbamate (5-HBC) and 2-aminobenzimidazole (2-AB) were formed very rapidly /in rats admin 12 mg/kg iv/. Their peak concentrations in liver and kidney were 15 min after i.v. injection. Unchanged carbendazim was found in highest concentrations in blood. 5-HBC prevails in organs. 2-AB was present only in minor amounts. The extent of bioavailability in orally administered 14C-carbendazim (12 mg/kg) was about 85%. The disposition of radioactivity in subcellular fractions was not uniform, its highest concentration was in cytosol, the lowest in microsomes. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

氨基甲酸酯通过肝脏酶促水解；降解产物通过肾脏和肝脏排出。

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

识别和使用：多菌灵是一种白色粉末。它是一种系统性叶面和土壤杀菌剂，通过根系和绿色组织吸收。人类暴露和毒性：研究了六对人类染色体（1和8、11和18以及X和17）。异常被归类为染色体丢失（包括着丝粒阳性微核）、染色体增加、非分离或多倍体。动物研究：先前的研究表明，多菌灵可能会干扰有丝分裂，从而可能破坏或抑制微管功能，导致凋亡。即使在低剂量下，多菌灵也表现出毒性，影响肝脏，并在大鼠的血常规和生化参数上引起特定变化。每组6只雄性大鼠分别以200、3400和5000毫克/千克的剂量每天5天/周，连续2周灌胃。在3400毫克/千克每天的剂量水平上，有2只大鼠死亡。在所有剂量水平上，都观察到对睾丸的明显和显微镜下不利影响，以及附睾中精子减少或缺失。睾丸小而变色，管状退化，并有精子发生减少的证据。在3400毫克/千克每天的剂量水平上，十二指肠（水肿和局部坏死）、骨髓（造血元素减少）和肝脏（大球形空泡减少）也出现了形态学变化。将1岁大的比格犬（4雄4雌）分组，在饮食中添加多菌灵3个月，剂量水平为0、100、500和2500毫克/千克。中剂量水平的雌性在1、2和3个月时与测试前和控制值相比，胆固醇水平呈上升趋势。高剂量雌性的胆固醇水平也有所升高。在低剂量和中剂量雄性的胸腺以及中剂量雄性的前列腺中观察到了器官与体重变化。在怀孕大鼠的妊娠第6-15天，以最高80毫克/千克的剂量水平通过灌胃给予多菌灵。怀孕兔在妊娠第6-18天以相似的方式给予最高160毫克/千克的剂量。在大鼠中，对照组的胎儿死亡和重吸收占29%，20毫克/千克时为48%，40毫克/千克时为64%，80毫克/千克时为73%。在兔中，对照组没有发现死亡或重吸收的胎儿，而在多菌灵处理的兔中发现了15-33%。大鼠或兔的活胎儿平均体重没有差异，也没有畸形。多菌灵诱导精子细胞中的染色体畸变，具有较高的非整倍体发生率。多菌灵在小鼠骨髓细胞中诱导微核。在诱变多菌灵样品中检测到了2,3-二氨基吩嗪（DAP）和2-氨基-3-羟基吩嗪（AHP）。在5000微克/板测试时，含有DAP或AHP水平低至5或10 ppm的多菌灵样品在沙门氏菌/埃姆斯试验中呈阳性反应。纯化的多菌灵没有诱变性。生态毒性研究：亚马逊鱼类对多菌灵的敏感性似乎略低于温带鱼类，其LC50值在1648至4238微克/升之间，而亚马逊无脊椎动物被发现比它们温带的同类显著抵抗，其LC50值高于16000微克/升。在植物中，多菌灵会导致某些基因的甲基化或去甲基化，并改变这些基因的表达。

IDENTIFICATION AND USE: Carbendazim is a white powder. it is a systemic leaf and soil fungicide, absorbed through the roots and green tissues. HUMAN EXPOSURE AND TOXICITY: Six human chromosomes were investigated in pairs (1 and 8, 11 and 18, and X and 17). Abnormalities were classified as chromosome loss (including centromeric positive micronuclei), chromosome gain, non-disjunction, or polyploidy. ANIMAL STUDIES: Previous studies indicate that carbendazim may interfere with mitosis and thus may disrupt or inhibit microtubule function resulting in apoptosis. Carbendazim even at low dose exhibited toxicity, affected the liver and also caused specific changes in hematological and biochemical parameters in the rat. Male rats (6 per dose level) were gavaged with 200, 3400 and 5000 mg/kg 5 days/wk for 2 wk. Two out of the 6 rats died at the dose level of 3400 mg/kg per day. At all dose levels, gross and microscopic evidence of adverse effects on the testes and reduction or absence of sperm in the epididymides was seen. The testes were small and discolored, with tubular degeneration and evidence of aspermatogenesis. At the dose level of 3400 mg/kg per day, there were also morphological changes in the duodenum (edema and focal necrosis), bone marrow (reduction in the blood forming elements) and liver (decrease in the large globular shaped vacuoles). Groups of 1 yr old beagles (4 males, 4 females) were admin carbendazim in the diet for 3 months at dietary levels of 0, 100, 500 and 2500 mg/kg. Females at the mid dose level showed a trend toward incr cholesterol levels at 1, 2 and 3 months compared with the pre-test and control values. High dose females also had elevated cholesterol levels. Organ to body weight changes were observed in the case of the thymus of low and mid dose males and the prostate of mid dose males. Groups of pregnant rats were administered carbendazim by gavage on days 6-15 of gestation at dose levels up to 80 mg/kg/day. Groups of pregnant rabbits were similarly administered up to 160 mg/kg/day on days 6-18 of gestation. In the rats, dead and resorbed fetuses accounted for 29% of conceptions in controls, 48% at 20 mg/kg, 64% at 40 mg/kg, and 73% at 80 mg/kg. In rabbits, no dead or resorbed fetuses were seen in controls whereas 15-33% were found in carbendazim-treated rabbits. There were no differences among rats or rabbits in mean weight of live fetuses, and there were no malformations. Carbendazim induced chromosome aberrations in spermatids with a high incidence of aneuploidy. Carbendazim induced micronuclei in mouse bone marrow cells. 2,3-diaminophenazine (DAP) and 2-amino-3-hydroxyphenazine (AHP) were detected in mutagenic carbendazim samples. Carbendazim samples containing DAP or AHP at levels as low as 5 or 10 ppm, respectively, were positive in the Salmonella/Ames test with activation when tested at 5000 ug/plate. Purified carbendazim was not mutagenic. ECOTOXICITY STUDIES: Amazonian fish appeared to be slightly less sensitive for carbendazim than temperate fish with LC50 values ranging between 1648 and 4238 ug/L, and Amazonian invertebrates were found to be significantly more resistant than their temperate counterparts, with LC50 values higher than 16000 ug/L. In plants, carbendazim causes methylation or demethylation of certain genes and changes the expression of these genes.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

多菌灵作用于活跃分裂细胞中的β-微管蛋白。它与微管结合，干扰细胞功能，如减数分裂和细胞内运输（A15332）。

Carbendazim targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (A15332).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

癌症分类：C组可能的人类致癌物

Cancer Classification: Group C Possible Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

多菌灵是一种疑似内分泌干扰物。它也是一种发育毒素。在子宫内接触多菌灵的动物会出现严重畸形，如失明和脑积水（大脑中有积水）。多菌灵可以干扰精子的发育并损害成年大鼠的睾丸发育。

Carbendazim is a suspected endocrine disruptor. It is also a developmental toxin. Animals exposed to carbendazim in the womb to have serious deformities such as lack of eyes and hydrocephalus (water on the brain). Carbendazim can disrupt the development of sperm and damage testicular development in adult rats.

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

在雄性大鼠中，单次口服3毫克/公斤后，6小时内尿液中有66%被排出。

In male rats, following a single oral admin of 3 mg/kg, 66% was eliminated in the urine within 6 hr.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  甲基1H-苯并咪唑-2-基氨基甲酸酯 在 potassium fluoride 、 硫酸 、 硝酸 、 copper diacetate 、 potassium carbonate 、 sulfur 作用下， 反应 24.0h， 生成 阿苯达唑
  参考文献：
  名称：

  一种[5-(丙硫基)-1H-苯并咪唑-2-基]氨基甲酸甲酯的合成方法

  摘要：

  本发明公开了一种[5‑(丙硫基)‑1H‑苯并咪唑‑2‑基]氨基甲酸甲酯的合成方法，其步骤是：1)甲基‑苯并咪唑‑2‑氨基甲酸甲酯、浓硫酸和硝化试剂在‑10‑2℃下反应2‑10h，得到5‑硝基苯并咪唑‑2‑氨基甲酸甲酯；2)在溶剂A中，加入5‑硝基苯并咪唑‑2‑氨基甲酸甲酯、1‑溴丙烷或1‑氯丙烷、硫代硫酸盐、碱和铜盐，反应5‑20h，得到阿苯达唑；或在溶剂B中，加入5‑硝基苯并咪唑‑2‑氨基甲酸甲酯、三正丙基氯化锡、硫磺、氟化钾、碱和铜盐，搅拌反应5‑20h，得到阿苯达唑；或在溶剂C中，加入5‑硝基苯并咪唑‑2‑氨基甲酸甲酯、正丙基硼酸、硫磺、碱和铜盐，反应5‑20h，得到阿苯达唑。该方法合成路线短，合成和分离简单，危险性小，环保安全。

  公开号：

  CN108530367A
• 作为产物：
  描述：

  苯菌灵 以 乙腈 为溶剂， 反应 3.0h， 生成 甲基1H-苯并咪唑-2-基氨基甲酸酯
  参考文献：
  名称：

  反相液相色谱法测定苯菌灵。

  摘要：

  DOI：

  10.1021/ac00259a066

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
  申请人：BASF SE

  公开号：WO2014206910A1

  公开（公告）日：2014-12-31

  The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及公式（I）中变量如索权和说明中所定义的自行车基取代异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包含所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] AZOLINE COMPOUNDS<br/>[FR] COMPOSÉS AZOLINE
  申请人：BASF SE

  公开号：WO2015128358A1

  公开（公告）日：2015-09-03

  The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式（I）的噁唑啉化合物，其中A、B1、B2、B3、G1、G2、X1、R1、R3a、R3b、Rg1和Rg2如权利要求和描述中所定义。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。

表征谱图