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敌菌丹 | 2425-06-1

中文名称
敌菌丹
中文别名
N-(1,1,2,2,-四氯乙硫基)-4-环已烯-1,2-二甲酰亚胺;N-四氯乙硫基四氢酞酰亚胺;福尔西一登;四氯丹
英文名称
captafol
英文别名
N-(1,1,2,2-tetrachloroethylthio)-1,2,3,6-tetrahydrophthalimide;Arborseal;2-(1,1,2,2-tetrachloroethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
敌菌丹化学式
CAS
2425-06-1
化学式
C10H9Cl4NO2S
mdl
——
分子量
349.065
InChiKey
JHRWWRDRBPCWTF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    160-161°
  • 沸点:
    365.7±52.0 °C(Predicted)
  • 密度:
    1.4682 (rough estimate)
  • 闪点:
    >100 °C
  • 溶解度:
    氯仿(少量溶解)、二氯甲烷(极少量)、甲醇(少量溶解)
  • 物理描述:
    Captafol is a white crystalline solid with a slight, but pungent odor. Mp: 162°C. Practically insoluble in water. Only slightly soluble in organic solvents. Technical captafol is a wettable light tan powder that is used as a fungicide. Inhaled dust irritates the respiratory tract. Irritates skin and damages eyes. Acute oral toxicity in humans is low. Not persistent in the environment (decomposes with a half-life of 11 days in the soil). Highly toxic to fish and other aquatic organisms.
  • 颜色/状态:
    White, solid
  • 气味:
    Slight, characteristic pungent odor.
  • 蒸汽密度:
    Relative vapor density (air = 1): 12
  • 蒸汽压力:
    8.27X10-9 mm Hg @ 20 °C
  • 稳定性/保质期:
    在常温常压下稳定,但在酸性和碱性条件下不稳定。它会在熔点温度时缓慢分解。
  • 分解:
    Rapidly hydrolyzed in acidic and alkaline media. At 50 °C, 50% decomposition occurs in about 3 hr at pH 6.
  • 保留指数:
    2337.9;2341.3;2323;2337.4

计算性质

  • 辛醇/水分配系数(LogP):
    3.8
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.6
  • 拓扑面积:
    62.7
  • 氢给体数:
    0
  • 氢受体数:
    3

ADMET

代谢
血液、组织或尿液中未检测到未改变的酰胺磷,在大鼠、狗和猴子中。主要单一代谢物,四氢酞酰亚胺,在血液、粪便和尿液中被检测到,但血液和尿液中的大部分活性是以更可溶的代谢物形式存在。未检测到酰胺磷环氧物...。
No unchanged captafol was detected in the blood, tissues, or urine /in rats, dogs, & monkeys/. The major single metabolite, tetrahydrophthalimide, was detected in blood, feces, & urine, but most of the activity in the blood and urine was in the form of more soluble metabolites. No captafol epoxide was detected ... .
来源:Hazardous Substances Data Bank (HSDB)
代谢
在哺乳动物中,口服给药后,以及在植物中,甲萘酚会被水解成四氢酞亚胺和二氯醋酸。四氢酞亚胺会降解为四氢酞亚胺酸,进而进一步降解为酞酸和氨。
In mammals, following oral administration, /and in plants/ captafol is hydrolyzed to tetrahydrophthalimide and dichloroacetic acid. Tetrahydrophthalimide is degraded to tetrahydrophthalimidic acid and further to phthalic acid and ammonia.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
识别:Captafol是一种氯代烷基硫化物杀菌剂。市面上有多种商业配方可供选择,包括与其他杀虫剂混合的Captafol。它实际上不溶于水,在大多数有机溶剂中略溶。这种杀菌剂是一种白色结晶固体。技术等级为浅棕色粉末,具有特有的气味。在强烈碱性条件下,它是不稳定的。Captafol有粉剂、可湿性粉剂和流动剂型。如果配方产品释放到水环境中,可能会对环境造成风险。Captafol是一种保护性非系统性杀菌剂,广泛应用于控制番茄、咖啡浆果病、马铃薯疫病和橡胶树割胶板病的叶子和果实病害。它还用于木材和木材工业,以减少原木和木材产品因木材腐朽真菌而造成的损失。人类接触:急性口服毒性低。皮肤、眼睛和呼吸道是局部刺激和过敏反应的目标。大量摄入Captafol后,有报道称出现呕吐和腹泻。已知发生过呼吸道过敏和结膜炎。系统性紊乱,包括高血压、肝和肾功能障碍,通常与皮炎程度平行,在接触Captafol后有所报道。由于支气管痉挛引起的喘息、接触性皮炎以及分别通过吸入、皮肤接触和摄入引起的呕吐和腹泻是接触Captafol的特征。慢性暴露可能导致高血压、肝功能减退、皮炎、结膜炎和贫血。接触者包括农场和木材工人;从事配方和分配杀虫剂的工人;农业喷洒工和作物收割工在疾病媒介控制期间。在职业环境中,有报道称吸入Captafol喷雾雾或粉末。动物研究:动物喂养研究发现,大部分Captafol以原形排出,主要代谢物为四氢邻苯二甲酰亚胺。当大鼠、狗和猴子喂食(14)C-Captafol时,几乎80%在36小时内排出,主要在尿液中,没有通过呼出的二氧化碳排出。粪便中的少量大部分未代谢,可能是未被吸收。在血液、组织或尿液中没有检测到未改变的Captafol。在血液、粪便和尿液中检测到主要代谢物四氢邻苯二甲酰亚胺,但血液和尿液中的大部分活性是以可溶性代谢物的形式存在。没有检测到Captafol环氧化合物。在一项大鼠的饮食研究中,任何剂量的肿瘤发生率都没有增加。最初给予单剂量二乙基亚硝胺ip的大鼠,两周后用含有Captafol的饮食喂养6周,然后处死。通过比较诱导谷胱甘肽S-转移酶胎盘形式阳性焦点的数量和每平方厘米面积与仅给予二乙基亚硝胺的相应对照组相比,来评分致癌潜力。Captafol显著增加了焦点的值。已经对许多哺乳动物物种,包括非人灵长类动物进行了多项畸胎学的研究。在大多数研究中,整个器官发生过程中给予Captafol,展示了低至无致畸潜力。兔子的研究结果是矛盾的。有两项研究没有畸形的胎儿,而另一项研究中,75个胎儿中有9个畸形。对371个胎儿进一步调查没有产生异常数量增加。在一项对金仓鼠的研究中,比较了单次给予Captafol的效果与在整个器官发生过程中重复给药的效果。在最高单次剂量时,母体死亡率增加,一些异常胎儿减少。在最低单次剂量和所有多次剂量时,没有致畸活性的迹象。使用含有A-T和G-C碱基对的Salmonella/哺乳动物微体菌株的Captafol诱变活性。S9混合物降低了Captafol的诱变活性。诱变活性根据所测试的菌株而有所不同。在测试Captafol诱导染色体突变的能力的研究中,除了在一次显性致死试验中重复多次阴性发现外,它不是致突变剂。在其他测试中,姐妹染色单体交换和睾丸DNA合成,Captafol为阴性。Captafol与达克宁、克螨特和波尔多液联合使用时,有强烈的致敏反应。有报道称职业暴露后出现结膜炎和眼周水肿。尿液中出现蛋白质和尿胆原,在接触这种杀虫剂后也有所报道。还有口腔炎和贫血的记录。
IDENTIFICATION: Captafol is a chloroalkyl thio fungicide. A number of formulations are commercially available which include captafol with other pesticides. It is practically insoluble in water and slightly soluble in most organic solvents. The fungicide is a white crystalline solid. The technical grade is a light tan powder with a characteristic odor. It is stable except under strongly alkaline conditions. Captafol is available as dusts, wettable powders and flowable formulations. The formulated product may pose an environmental risk if released into the aquatic environment. Captafol is a protective non-systemic fungicide widely used to control foliage and fruit diseases of tomatoes, coffee berry disease, potato blight, and tapping panel disease of rubber trees. It is also used in the lumber and timber industries to reduce losses from wood rot fungi in logs and wood products. HUMAN EXPOSURE: The acute oral toxicity is low. Skin, eyes and respiratory tract are targets for local irritation and sensitization. Following ingestion of large quantities of captafol, vomiting and diarrhea have been reported. Respiratory sensitization and conjunctivitis are known to have occurred. Systemic disorders including hypertension, hepatic and renal disturbances, usually paralleling the degree of dermatitis, have been reported following captafol exposure. Wheezing due to bronchospasm, contact dermatitis and vomiting and diarrhea are the features of exposure to captafol by inhalation, skin contact and ingestion respectively. Chronic exposure can cause hypertension, depression of liver function, dermatitis, conjunctivitis and anemia.Exposed individuals include farm and timber workers; workers involved in formulation and dispensing pesticides; agricultural spray workers and crop harvesters during disease vector control periods. Inhalation of captafol as spray mists or powders have been reported in an occupational context. ANIMAL STUDIES: Animal feeding studies have shown that most of the captafol is excreted unchanged and the major metabolite being tetrahydrophthalimide. When rats, dogs and monkeys were fed (14)C-captafol almost 80% was excreted with in 36 hr, mainly in the urine and none via expired carbon dioxide. Most of the small amount in the feces was unmetabolized and probably unabsorbed. No unchanged captafol was detected in the blood, tissues or urine. The major metabolite, tetrahydrophthalimide was detected in the blood, feces and urine, but most of the activity in the blood and urine was in the form of soluble metabolites. No captafol epoxide was detectable. In a dietary study of captafol fed to rats, the incidence of tumors was not increased at any dosage. Rats initially given a single dose of diethylnitrosamine ip were fed two weeks later with a diet containing captafol for 6 weeks and then sacrificed. Carcinogenic potential was scored by comparing the number and area per sq cm of induced glutathione S-transferase placental form positive foci in the liver with those of a corresponding control group given diethylnitrosamine alone. Captafol showed a significant increase in the value of foci. Several teratology studies have been conducted in many mammalian species, including non-human primates. In most studies, where captafol was administered throughout organogenesis, low to no teratogenic potential was demonstrated. Studies with rabbits were contradictory. There have been two studies with no malformed fetuses and one in which 9 of 75 fetuses were malformed. Further investigation of 371 fetuses did not produce a single increase in the number of abnormalities. In a study with golden hamsters, effects of single administration of captafol was compared with effects of repeated administration throughout organogenesis. At the highest single doses maternal mortality increased and some abnormal fetuses were reduced. At the lowest single doses and all multiple doses there were no indications of teratogenic activity. The mutagenicity of captafol using the Salmonella/mammalian microsome with strains containing A-T and G-C base pairs. The S9 mix decreased the mutagenic activity of captafol. Mutagenic activity varied depending upon the strain tested. In studies to test the ability of captafol to induce chromosomal mutations, it was not mutagenic except in a single dominant lethal test repeated by others several times with negative findings. In other tests, sister chromatic exchange and testicular DNA synthesis, captafol was negative. Captafol has strong sensitization reactions in combination with daconil, kelthane and bordeaux. Conjunctivitis and periorbital edema has been reported following occupational exposure. Protein and urobilinogen in the urine have been reported following captafol exposure. Stomatitis and anemia have also been noted after exposure to this pesticide.[
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
评估:没有来自人类研究的可用数据。有充分的证据表明,实验动物中的克菌丹具有致癌性。在做出总体评估时,工作组考虑了以下支持性证据:克菌丹在广泛的遗传和相关效应测试中显示出活性,包括通常不敏感的体内显性致死突变试验。总体评估:克菌丹可能对人类具有致癌性(2A类)。
Evaluation: No data were available from studies in humans. There is sufficient evidence in experimental animals for the carcinogenicity of captafol. In making the overall evaluation, the working group took into consideration the following supporting evidence: Captafol is active in a wide range of tests for genetic and related effects, including the generally insensitive in vivo assay for dominant lethal mutation. Overall evaluation: Captafol is probably carcinogenic to humans (2A).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
癌症分类:2B组 可能的人类致癌物
Cancer Classification: Group 2B Probable Human carcinogen
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
A4;不可归类为人类致癌物。
A4; Not classifiable as a human carcinogen.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌物分类
国际癌症研究机构致癌物:卡普他福尔
IARC Carcinogenic Agent:Captafol
来源:International Agency for Research on Cancer (IARC)
吸收、分配和排泄
当老鼠、狗和猴子被喂食含有14C标记的卡普塔夫尔时,几乎80%在36小时内被排出,主要是在尿液中,没有以呼出的二氧化碳形式排出。在血液、组织或尿液中没有检测到未改变的卡普塔夫尔。
When rats, dogs, & monkeys were fed (14)C captafol, almost 80% was excreted within 36 hr, mainly in the urine and none /as/ expired carbon dioxide. ... No unchanged captafol was detected in the blood, tissues, or urine.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
被皮肤吸收。
Absorbed by skin.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 职业暴露等级:
    D
  • 职业暴露限值:
    TWA: 0.1 mg/m3 [skin]
  • 危险品标志:
    N,T
  • 安全说明:
    S45,S53,S60,S61
  • 危险类别码:
    R50/53,R43,R45
  • 海关编码:
    29305000
  • 危险品运输编号:
    UN3077 9/PG 3
  • RTECS号:
    GW4900000

制备方法与用途

农业杀菌剂:敌菌丹

外观及物理化学性质

敌菌丹为白色结晶固体,熔点为160~161℃。在室温下几乎不挥发,难溶于水但微溶于大多数有机溶剂。其分解缓慢且在强碱条件下不稳定,在熔点温度时会缓慢分解。工业品呈现亮黄褐色粉末状。

用途与毒性

敌菌丹是一种用于叶面喷施的非内吸性、保护性农业杀菌剂,1961年由美国Chevron化学品公司生产(Chevron Chemical Company)。它可防治多种作物上的霜霉病、疫病、炭疽病等。敌菌丹对大鼠口服的LD50为5,000~6,200 mg/kg,毒性属于低毒级别,但使用时仍需注意安全,防止吸入或接触皮肤,配药和施药人员应穿戴防护装备。

注意事项

  1. 请勿与碱性药剂及油类物质混用。
  2. 使用过程中,操作人员应注意个人防护,避免吸入药液或接触皮肤。
  3. 如有对敌菌丹过敏反应,需及时处理皮疹等症状。
  4. 施药后清洗各种工具,并妥善处置污水和剩余药液,防止污染环境。
  5. 运输和储存时应有专门的车皮和仓库,不得与食物及日用品混放。

制备方法

敌菌丹由丁二烯和顺丁烯二酸酐反应生成四氢邻苯二酸酐,然后通过氨与四氢邻苯二酸酐作用形成亚胺,再与1,1,2,2-四氯乙基氯化硫反应而成。图1展示了其合成路线。

作用方式

敌菌丹是一种多作用点的广谱保护性杀菌剂,结构中的二甲酰亚胺基(-CON(H)co-)具有较高的杀菌活性,可用于防治果树、蔬菜和经济作物上的根腐病、立枯病、霜霉病、疫病和炭疽病。不过对白粉病效果较差,除喷雾使用外,也可作为土壤消毒和种子处理用。

毒性

敌菌丹大鼠急性口服LD50为2,500 mg/kg(80%可湿性粉剂水悬液),大白兔经皮毒性LD50大于15,400 mg/kg。长期饲养实验中,每日使用500 mg/kg对大鼠或10 mg/kg剂量对狗均未产生中毒现象。然而,有人对其过敏,并证实具有致癌作用。敌菌丹对野鸭和家鸭的急性口服LD50分别为大于23,070 mg/kg和101,700 mg/kg。此外,对虹鳟鱼、金鱼和青鳃鱼的接触4天半致死浓度(LC50)分别为0.5 mg/L、3.0 mg/L和0.15 mg/L,大翻车鱼为2.8 mg/L。

防治对象

敌菌丹曾广泛用于防治番茄叶和果实的病害、马铃薯枯萎病及咖啡仁果病等。此外,它也可作为木材防腐剂使用。关于敌菌丹的农业杀菌剂、制备方法、作用方式及其毒性等方面的信息由Chemicalbook的玉莲编辑整理(2016-03-04)。

剂型

常见的敌菌丹制剂为80%可湿性粉剂(Difolatan)。

化学性质

黄褐色至类白色粉末状。

类别

农药。

毒性分级

低毒。

急性毒性
  • 大鼠口服LD50:2,500毫克/公斤
  • 腹腔注射小鼠LDLo:3毫克/公斤
可燃性危险特性

燃烧时产生有毒氯化物、氮氧化物和磷氧化物气体。

储运特性

库房需通风干燥,低温保存。与食品原料分开储存运输。

灭火剂

干粉、泡沫、砂土。

职业标准

时间加权平均容许浓度(TWA):0.1毫克/立方米。

反应信息

  • 作为反应物:
    描述:
    、 mancozeb 、 敌菌丹敌菌丹 作用下, 生成 代森锰锌
    参考文献:
    名称:
    Fungicidal compositions based on alkyl phosphites
    摘要:
    提供了一种杀真菌组合物和用于保护葡萄藤免受疾病侵害的方法。该组合物应用于葡萄藤上,其活性物质含有以下配方的磷酸单酯盐混合物的1份重量:##STR1## 其中R是具有2到4个碳原子的烷基基团,Me是碱金属、碱土金属或铝原子,n是整数,从1到3等于Me的价数,并且从0.05到8份的至少一种接触性杀真菌剂,所述接触性杀真菌剂选自具有铜基础的化合物、金属乙撑二硫代氨基甲酸盐和邻苯二甲酰亚胺衍生物。
    公开号:
    US04698334A1
  • 作为试剂:
    描述:
    、 mancozeb 、 敌菌丹敌菌丹 作用下, 生成 代森锰锌
    参考文献:
    名称:
    Fungicidal compositions based on alkyl phosphites
    摘要:
    提供了一种用于保护葡萄藤免受疾病侵害的杀菌剂组合物和方法。该组合物应用于葡萄藤上,其活性物质包含以下成分的混合物:1份重量的磷酸单酯盐,其化学式为##STR1## 其中R是具有2到4个碳原子的烷基基团,Me是碱金属、碱土金属或铝原子,n是1到3的整数,等于Me的价,以及0.05到8份的至少一种接触型杀菌剂,所述接触型杀菌剂选自以铜为基础的化合物、金属乙撑二硫代氨基甲酸盐和邻苯二甲酰亚胺的衍生物。
    公开号:
    US05169646A1
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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。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
hnmr
mass
cnmr
ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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