4,5-二氯-2-三氟甲基苯并咪唑 | 3615-21-2

• 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: 4,5-二氯-2-三氟甲基苯并咪唑
• 英文名称: 4,5-Dichlor-2-trifluormethyl-benzimidazol
• 英文别名: Chlorflurazole；4,5-dichloro-2-(trifluoromethyl)-1H-benzimidazole
• CAS: 3615-21-2
• 化学式: C₈H₃Cl₂F₃N₂
• 分子量: 255.026
• InChiKey: KSROTSBULDYPKA-UHFFFAOYSA-N

物化性质

• 熔点：
  213.5°C
• 沸点：
  337.8±42.0 °C(Predicted)
• 密度：
  1.5776 (estimate)
• 物理描述：
  Benzimidazole, 4,5-dichloro-2-(trifluoromethyl)- appears as a crystalline solid. Fine white needles when pure; the commercial material is brownish. Used as an herbicide. (EPA, 1998)
• 颜色/状态：
  CRYSTALLINE SOLID, FORMING FINE WHITE NEEDLES WHEN PURE.
• 闪点：
  (Non-Specific -- Pesticide, solid, n.o.s.) May burn, but does not ignite readily. (EPA, 1998)
• 溶解度：
  69 PPM IN WATER @ 25 °C; SPARINGLY SOL IN METHYL NAPHTHALENE & BENZENE; SOL UP TO 25% IN ETHANOL, ETHER, CHLOROFORM, PROPYLENE GLYCOL, GLYCEROL FORMAL, METHYL NAPHTHALENE; VERY SOL IN ACETONE.
• 蒸汽压力：
  4X10-5 MM HG @ 22.5 °C
• 稳定性/保质期：
  ... VOLATILITY LOW ... AQUEOUS SALT FORMULATIONS ARE BELIEVED CHEMICALLY STABLE IN AIR.

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

产量4,5-二氯-6-羟基-2-三氟甲基苯并咪唑和4,5-二氯-7-羟基-2-三氟甲基苯并咪唑在大鼠和小鼠体内的含量。/来自表格/

YIELDS 4,5-DICHLORO-6-HYDROXY-2-TRIFLUOROMETHYLBENZIMIDAZOLE & 4,5-DICHLORO-7-HYDROXY-2-TRIFLUOROMETHYLBENZIMIDAZOLE IN RABBIT & RAT. /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

代谢

小鼠肝脏微粒体混合功能氧化酶将氯氟唑的苯环部分进行了羟基化。给予大鼠口服1.5毫克后，尿液中含有主要的6-羟基-4,5-二氯-2-三氟甲基苯并咪唑结合物，少量的7-羟基-4,5-二氯-2-三氟甲基苯并咪唑结合物和5-羟基-4,6-二氯-2-三氟甲基苯并咪唑结合物。

MICROSOMAL MIXED FUNCTION OXIDASES OF MOUSE LIVER HYDROXYLATED THE BENZENE MOIETY OF CHLOROFLUORAZOLE. URINE OF RATS ADMIN 1.5 MG ORALLY CONTAINED 6-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MAJOR, 7-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MINOR, & 5-HYDROXY-4,6-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MINOR.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在给予兔子和大鼠口服给药后，其24小时内的尿液中经过酸水解后含有7-羟基-4,5-二氯-2-三氟甲基苯并咪唑、6-羟基-4,5-二氯-2-三氟甲基苯并咪唑以及6,7-二氧代-4,5-二氯-2-三氟甲基苯并咪唑的葡萄糖苷酸和硫酸盐。

1ST 24-HR URINARY METAB AFTER ORAL ADMIN TO RABBITS & RATS CONTAINED AFTER ACID HYDROLYSIS 7-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, 6-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, & 6,7-DIOXO-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE GLUCURONIDES & SULFATES

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

1. 应立即用肥皂和水清洗去除皮肤污染。眼睛污染应立即通过大量清水长时间冲洗眼睛来处理。如果皮肤或眼睛刺激持续存在，应立即寻求医疗注意。/其他除草剂/

1. SKIN CONTAMINATION SHOULD BE REMOVED PROMPTLY BY WASHING WITH SOAP AND WATER. CONTAMINATION OF THE EYES SHOULD BE TREATED IMMEDIATELY BY PROLONGED FLUSHING OF THE EYES WITH COPIOUS AMOUNTS OF CLEAN WATER. IF DERMAL OR OCULAR IRRITATION PERSISTS, MEDICAL ATTENTION SHOULD BE OBTAINED WITHOUT DELAY. /OTHER HERBICIDES/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

这些除草剂的摄入很可能会引起呕吐和腹泻，因为大多数有毒物质都具有刺激性质。如果摄入了大量除草剂，并且患者意识清醒，请使用吐根糖浆诱导呕吐，随后喝几杯水。成人及12岁以上儿童的剂量为30毫升；12岁以下儿童的剂量为15毫升。呕吐停止后，给予活性炭。除非已经出现腹泻，否则在活性炭悬浮液中加入山梨醇。如果由于某种原因患者意识不清醒，请放置带套囊的气管内导管以保护气道，然后用活性炭悬浮液抽吸和灌洗胃部。在拔除胃管之前，在胃中留下一定量的含山梨醇的活性炭。每隔2-4小时重复给予半量或更多初始剂量的活性炭可能会有益。/其他除草剂/

2. INGESTIONS OF THESE HERBICIDES ARE LIKELY TO BE FOLLOWED BY VOMITING AND DIARRHEA DUE TO THE IRRITANT PROPERTIES OF MOST OF THE TOXICANTS. ... A. IF LARGE AMOUNTS OF HERBICIDE HAVE BEEN INGESTED, AND IF THE PATIENT IS FULLY ALERT INDUCE EMESIS WITH SYRUP OF IPECAC, FOLLOWED BY SEVERAL GLASSES OF WATER. DOSAGE FOR ADULTS AND CHILDREN OVER 12 YEARS: 30 ML; DOSAGE FOR CHILDREN UNDER 12 YEARS 15 ML. WHEN VOMITING HAS STOPPED, GIVE ACTIVATED CHARCOAL. ADD SORBITOL TO THE CHARCOAL SLURRY UNLESS DIARRHEA HAS ALREADY COMMENCED. IF, FOR SOME REASON, THE PATIENT IS NOT FULLY ALERT, PUT IN PLACE A CUFFED ENDOTRACHEAL TUBE TO PROTECT THE AIRWAY, THEN ASPIRATE AND LAVAGE THE STOMACH WITH A SLURRY OF ACTIVATED CHARCOAL. LEAVE A QUANTITY OF CHARCOAL, WITH SORBITOL, IN THE STOMACH BEFORE WITHDRAWING THE STOMACH TUBE. REPEATED ADMINISTRATION OF CHARCOAL AT HALF OR MORE THE INITIAL DOSAGE EVERY 2-4 HOURS MAY BE BENEFICIAL. /OTHER HERBICIDES/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

如果摄入的除草剂量较小，如果已经发生了有效的呕吐，或者如果治疗延迟，通过口腔给予活性炭和山梨醇。如果由于呕吐和腹泻已经发生了严重脱水和电解质耗尽，监测血液电解质和液体平衡，并通过静脉输注葡萄糖、正常盐水林格溶液或乳酸林格液来恢复细胞外液容量和电解质。一旦能够保留液体，随即给予口服营养。液体有助于支持有毒物质的排泄。对于这些除草剂的过度暴露，通常支持性措施就足以成功管理。/其他除草剂/

2. B. IF THE AMOUNT OF INGESTED HERBICIDES WAS SMALL, IF EFFECTIVE EMESIS HAS ALREADY OCCURRED, OR IF TREATMENT IS DELAYED, ADMINISTER THE ACTIVATED CHARCOAL AND SORBITOL BY MOUTH. C. IF SERIOUS DEHYDRATION AND ELECTROLYTE DEPLETION HAVE OCCURRED AS A RESULT OF VOMITING AND DIARRHEA, MONITOR BLOOD ELECTROLYTES AND AND FLUID BALANCE AND ADMINISTER INTRAVENOUS INFUSIONS OF GLUCOSE, NORMAL SALINE RINGER'S SOLUTION, OR RINGER'S LACTATE TO RESTORE EXTRACELLULAR FLUID VOLUME AND ELECTROLYTES. FOLLOW THIS WITH ORAL NUTRIENTS AS SOON AS FLUIDS CAN BE RETAINED. FLUIDS SERVE TO SUPPORT EXCRETION OF THE TOXICANTS. D. SUPPORTIVE MEASURES ARE ORDINARILY SUFFICIENT FOR SUCCESSFUL MANAGEMENT OF EXCESSIVE EXPOSURES TO THESE HERBICIDES. /OTHER HERBICIDES/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

非对谷物有毒。接触喷雾的蜜蜂在1000 ppm纯氯氟唑水悬浮液或钠盐溶液中没有受到影响，但在4000 ppm下会被杀死。一种氧化磷酸化解偶联剂，在6x10-7摩尔浓度下能引起大鼠肝脏线粒体氧化磷酸化50%的解偶联，同时也能刺激ATP酶活性和细胞呼吸。

NON-PHYTOTOXIC TO CEREALS. BEES EXPOSED TO SPRAY WERE UNAFFECTED BY 1000 PPM PURE CHLORFLURAZOLE AS AQUEOUS SUSPENSION OR SODIUM SALT SOLN, BUT WERE KILLED BY 4000 PPM. ... AN UNCOUPLER OF OXIDATIVE PHOSPHORYLATION CAUSING 50% UNCOUPLING OF RAT LIVER MITOCHONDRIAL OXIDATIVE PHOSPHORYLATION AT 6X10-7 MOLAR ALSO STIMULATING ATPASE ACTIVITY & CELL RESPIRATION.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在给予大鼠和家兔口服(14)C标记的4,5-二氯-2-三氟甲基硼苯并咪唑后，(14)C在3天内通过尿液排出。

FOLLOWING ORAL ADMIN TO RATS & RABBITS OF (14)C-LABELED 4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, (14)C WAS EXCRETED IN THE URINE IN 3 DAYS.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 海关编码：
  2933990090
• 包装等级：
  II
• 危险类别：
  6.1(a)

制备方法与用途

类别：农药
毒性分级：中毒
急性毒性：

• 大鼠 LD50: 4000 毫克/公斤；小鼠 LD50: 3000 毫克/公斤
  可燃性危险特性：燃烧会产生有毒的氮氧化物、氟化物和氯化物气体
  储运特性：库房应通风、低温干燥，并与食品原料分开存放运输
  灭火剂：干粉、泡沫、砂土

文献信息

• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions aga inst such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula ("Formula One").

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下化学式（“化学式一”）的分子。
• MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
  申请人：Dow AgroSciences LLC

  公开号：US20170210723A1

  公开（公告）日：2017-07-27

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的组合物，以及使用这种分子和组合物对抗这些害虫的过程。这些分子和组合物可以用作杀螨剂、杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂。本文件披露了具有以下式（“式一”）的分子。
• HYDRAZONYL GROUP-CONTAINING CONDENSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US20190177319A1

  公开（公告）日：2019-06-13

  An object of the present invention is to develop and provide a novel agricultural and horticultural insecticide in view of the still immense damage caused by insect pests etc. and the emergence of insect pests resistant to existing insecticides in crop production in the fields of agriculture, horticulture and the like. Provided is a hydrazonyl group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by the general formula (1): wherein R 1 represents, for example, an alkyl group, R 2 represents, for example, a hydrogen atom, R 3 and R 4 each represent, for example, an alkyl group, a haloalkyl group or an acyl group, A 1 represents, for example, a nitrogen atom, A 2 represents, for example, N-Me or an oxygen atom, A 3 represents, for example, a carbon atom or a nitrogen atom, A 4 represents, for example, C—H, m represents, for example, 2, and n represents, for example, 1}, or a salt thereof; an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

  本发明的一个目的是开发并提供一种新型农艺和园艺杀虫剂，鉴于昆虫害虫等造成的损害仍然巨大，以及在农业、园艺等领域作物生产中出现的对现有杀虫剂具有抗性的昆虫害虫。 提供了一种含有肼酰基的稠合杂环化合物或其盐，优选为通式(1)表示的稠合杂环化合物： 其中R1代表例如烷基，R2代表例如氢原子，R3和R4各自代表例如烷基、卤代烷基或酰基，A1代表例如氮原子，A2代表例如N-Me或氧原子，A3代表例如碳原子或氮原子，A4代表例如C—H，m代表例如2，n代表例如1}，或其盐；一种包含该化合物或其盐作为活性成分的农艺和园艺杀虫剂；以及使用该杀虫剂的方法。
• [EN] MACROCYCLIC PICOLINAMIDES AS FUNGICIDES<br/>[FR] PICOLINAMIDES MACROCYCLIQUES À UTILISER EN TANT QUE FONGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017116954A1

  公开（公告）日：2017-07-06

  The invention relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.

  本发明涉及式(I)所示的大环吡啶酰胺及其作为杀菌剂的应用。

表征谱图