triticonazole | 131983-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triticonazole
• 英文别名: (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol；2-(4-chlorobenzylidene)-5,5-diemethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol；(5E)-5-[(4-chlorophenyl)methylidene]-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol
• CAS: 131983-72-7；138182-18-0
• 化学式: C₁₇H₂₀ClN₃O
• 分子量: 317.818
• InChiKey: PPDBOQMNKNNODG-NTEUORMPSA-N

物化性质

• 熔点：
  143～149℃
• 沸点：
  498.7±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30 mg/ml； DMSO：30 mg/ml；乙醇：30 mg/ml；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml
• 颜色/状态：
  White powder
• 气味：
  Odorless at 22 °C
• 蒸汽压力：
  3.4X10-9 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Slight decomposition at 180 °C.
• 分解：
  When heated to decomposition it emits toxic vapors of /nitrogen oxides and Cl-/.
• 碰撞截面：
  179.18 Ų [M+H]+ [CCS Type: TW]

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

遗传毒性：人类淋巴细胞（全血）在激活和非激活条件下，分别在37°C下与Triticonazole（RPA 400727，纯度：90.9%）以7.751至800 ug/mL（第一次试验，男性）和33.79至800 ug/mL（第二次试验，女性）的浓度范围内进行处理。在激活条件下，细胞暴露于试验物质3小时，洗涤后额外孵化17小时（第一次试验）和17或41小时（第二次试验）。在非激活实验中，细胞暴露于试验物质20小时（第一次试验）和20或44小时（第二次试验）。使用了预先用Aroclor 1254处理过的雄性大鼠的肝脏匀浆S9组分来代谢试验物质。在第一次试验中，在非激活条件下，两种较高处理水平评估中，异常细胞的数量呈剂量相关增加（p<0.01和p<0.001）。大多数异常是染色体或染色单体缺失。在第二次试验中，对于孵化20小时的细胞，这种异常细胞数量的增加并不明显。在未激活条件下，暴露于试验物质44小时的一个处理水平评估中，异常细胞的数量增加了（p<0.05）。试验物质的代谢似乎并未导致染色体异常细胞数量的增加。试验结果提示在没有激活的情况下有阳性反应。结果表明，试验物质可能具有遗传毒性。指示的副作用：在非激活条件下，染色体异常细胞的数量增加。阳性对照在激活和非激活条件下都是有效的。

/GENOTOXICITY/ Human lymphocytes (whole blood) were treated with Triticonazole (RPA 400727, purity: 90.9%) at concentrations ranging from 7.751 to 800 ug/mL in the 1st trial (male) and 33.79 to 800 ug/mL in the 2nd trial (female) under conditions of activation and non-activation at 37deg C. Under conditions of activation, the cells were exposed to the test material for 3 hrs, washed and then incubated for an additional 17 hrs (1st trial) and 17 or 41 hrs (2nd trial). In the non-activated assays, the cells were exposed to the test material for 20 hrs (1st trial) and 20 or 44 hrs (2nd trial). A liver homogenate S9 fraction from male rats pretreated with Aroclor 1254 was used to metabolize the test material. In the first trial, an increase in cells with aberrations was noted in a dose-related manner at the two higher treatment levels evaluated (p<0.01 and p<0.001) under conditions of non-activation. The majority of the aberrations were chromosomal or chromatid deletions. This increase in the number of cells with aberrations was not as evident in the 2nd trial for the cells incubated for 20 hrs. For the one treatment level evaluated after exposure to the test material for 44 hrs without activation, the number of cells with aberrations was increased (p<0.05). Metabolism of the test material did not apparently result in an increased number of cells with chromosomal aberrations. The results of the assay were suggestive of a positive response without activation. The results indicate that the test material is possibly genotoxic. Indicated adverse effect: increased numbers of cells with chromosomal aberrations without activation. The positive controls were functional for both activation and non-activation.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/迟发型接触超敏反应是通过使用30只年轻的成年雄性和雌性Dunkin Hartley白化豚鼠，通过Magnusson-Kligman最大化测试来评估的。十只雄性和十只雌性豚鼠在第一天接受了以下三种治疗的皮内注射：Freunds完全佐剂；5% w/v曲康唑（纯度：92.5%）活性成分产品在丙二醇中；以及5% w/v曲康唑（纯度：92.5%）在佐剂中。七天后，同一部位的皮肤通过局部应用50% w/v曲康唑在丙二醇中处理，并在48小时内用封闭敷料覆盖测试部位。同一诱导程序同时对一组十只雄性和十只雌性动物进行了对照，除了所有剂量的测试材料被替换为载体（丙二醇）。在第22天，所有动物都通过在左腹部封闭应用丙二醇以及在右侧两个部位应用50% w/v曲康唑在丙二醇和10% w/v曲康唑在丙二醇进行了挑战。封闭敷料在第二天被移除，测试部位在大约24小时和48小时后进行评分。重复给予曲康唑没有在豚鼠中引起迟发型接触超敏反应。根据这项研究的结果，建议对曲康唑进行非致敏分类。皮内注射5% w/v曲康唑在丙二醇或佐剂中引起了轻微或中度的红斑、苍白和变色。局部应用50% w/v曲康唑在丙二醇中在大多数动物中引起了几乎无法察觉或轻微的红斑和脱屑。没有观察到对10% w/v曲康唑在丙二醇中的挑战的显著反应。在用50% w/v曲康唑在丙二醇中挑战后，三只对照动物和没有测试动物出现了显著反应（轻微红斑）。实验室认为对照动物的反应是偶然的。

/LABORATORY ANIMALS: Acute Exposure/ Delayed contact hypersensitivity was assessed using 30 young adult male and female Dunkin Hartley albino guinea pigs by the Magnusson-Kligman Maximization Test. Ten males and ten females received intradermal injections of each of the following three treatments: Freunds Complete Adjuvant; 5% w/v Triticonazole (purity: 92.5%) active ingredient product in propylene glycol; and 5% w/v Triticonazole (purity: 92.5%) in the adjuvant on Day 1. Seven days later the same area of skin was treated by topical application of 50% w/v Triticonazole in propylene glycol and the test site was covered by an occlusive dressing for 48 hours. The same induction procedures were carried out on a concurrent control group of ten male and ten female animals, except the test material was replaced by vehicle (propylene glycol) in all doses. On Day 22, all animals were challenged by occluded application of propylene glycol to the left flank and 50% w/v Triticonazole in propylene glycol and 10% w/v Triticonazole in propylene glycol to two sites on the fright flank. The occlusive dressings were removed on the following day and the test sites were scored approximately 24 and 48 hours later. Repeated administrations of Triticonazole did not cause delayed contact hypersensitivity in guinea-pigs. A non-sensitizer classification is proposed for Triticonazole based on the results of this study. Intradermal injection of 5% w/v Triticonazole in propylene glycol or the adjuvant caused slight or moderate erythema, pallor and discoloration. Topical application of 50% w/v Triticonazole in propylene glycol caused barely perceptible or slight erythema and exfoliation in most animals. No significant response was observed to challenge with 10% w/v Triticonazole in propylene glycol. A significant response (slight erythema) was observed in three control and no test animals following challenge with 50% w/v Triticonazole in propylene glycol. The laboratory considered that the reaction with the control animal was incidental.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  N
• 危险类别码：
  R51/53
• 危险品运输编号：
  UN 3077
• WGK Germany：
  2
• RTECS号：
  GY4705000
• 海关编码：
  2933990016
• 安全说明：
  S61

制备方法与用途

农用杀菌剂灭菌唑

灭菌唑是由Rhone-Poulenc农用化学品公司研制的新型广谱内吸性三唑类农用杀菌剂，为甾醇生物合成中C-14α-脱甲基化酶抑制剂。它主要用于防治禾谷类、豆科作物和果树病害，对白粉病、菌核病、枯萎病、纹枯病、网枯病、锈病、叶斑病和云纹病等作物病害均具有良好的防治效果。灭菌唑作为种衣剂能防治作物种子的靶标真菌病害，并对植株保持长期的防治效果。除可作为拌种剂之外，灭菌唑还可进行茎叶喷雾，持效期长达4-6周，能够防治草地早熟褐斑病。

理化性质

灭菌唑为白色粉状固体，无味（20℃），熔点为139°C~140.5°C，沸点前分解，蒸汽压小于1×10^-5 mPa （50℃），正辛醇水分配系数KowlogP = 3.29（20℃，pH=7.0），密度为1.326~1.369（20℃）。其溶解度在水中为9.3mg/L（20℃）；稳定性方面，在180°C时轻微分解。

毒性

灭菌唑原药属于低毒农药，大鼠急性经口LD50(雄/雌) > 2000 mg/kg，大鼠急性经皮LD50(雌/雄)> 2000 mg/kg，大鼠急性吸入毒性LC50(雌/雄) > 5.6mg/L。对鸟类、蜜蜂及水生动植物鱼类、藻类和溞类的急性毒性为低毒或中毒。

专利情况

灭菌唑是由德国拜耳公司于1988年研制的三唑类杀菌剂，于1993年首次在法国取得登记，后授权德国巴斯夫公司在欧洲等地销售。目前该产品已覆盖欧洲绝大多数国家，并进入阿根廷、澳大利亚、巴西、加拿大、哈萨克斯坦、巴基斯坦、南非、突尼斯、土耳其、美国和中国等市场。罗纳·普朗克农业化学公司于1989年12月29日申请灭菌唑专利（专利号：CN1031971C），目前该专利保护期已届满。

生物活性

Triticonazole 是一种三唑类农药，具有干扰内分泌作用。其靶点主要为真菌。

合成方法

以二甲基环戊酮为起始原料，与对氯苯甲醛缩合；再与碘代三甲基亚砜（由碘甲烷与二甲基亚砜制得)反应生成取代的环氧丙烷；最后与三唑反应处理即得灭菌唑。反应式如下：

[ \text{反应方程式} ]

参考资料

1. 李美霞, 陈香华, 周长勇等. 灭菌唑与氰烯菌酯复配对水稻恶苗病菌的抑制活性[J]. 农药学学报, 2022, 24: 1547-1551.
2. 陈柏. 28%灭菌唑悬浮种衣剂在玉米和土壤中的残留研究[J]. 世界农药, 2021, 43: 38-42.
3. 郑媛. 杀菌剂抑霉唑、灭菌唑诱导的烟曲霉抗药性及抗性机理[D]. 浙江大学, 2017.
4. 廖朝选, 张清海, 杨鸿波等. 灭菌唑对日本鹌鹑的急性毒性评价[J]. 贵州科学, 2014, 32: 65-68.
5. MONICA KAM DRASKAU . In vitro and in vivo endocrine disrupting effects of the azole fungicides triticonazole and flusilazole[J]. Environmental Pollution, 2019, 255: Article 113309. DOI:10.1016/j.envpol.2019.113309

反应信息

• 作为反应物：
  描述：

  triticonazole 生成 1-[[(5E)-5-[(4-chlorophenyl)methylidene]-1-methoxy-2,2-dimethylcyclopentyl]methyl]-1,2,4-triazole
  参考文献：
  名称：

  HUTT, JEAN;MUGNIER, JACQUES;PEPIN, REGIS

  摘要：

  DOI：
• 作为产物：
  描述：

  7-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-4, 4-dimethyl-1-oxa-spiro[2.4]heptane 、 1H-1,2,4-三唑 生成 triticonazole
  参考文献：
  名称：

  HUTT, JEAN;MUGNIER, JACQUES;PEPIN, REGIS

  摘要：

  DOI：

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。