三氯苯哒唑 | 68786-66-3

• 物质功能分类: 生物化工 - 抑制剂 - 细胞骨架(Cytoskeletal Signaling)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 三氯苯哒唑
• 中文别名: 5-氯-6-(2,3-二氯苯氧基)-2-甲硫基-1H-苯并咪唑；三氯苯咪唑；三氯苯达唑；5-氯-6-(2,3-二氯苯氧基)-2-(甲硫基)-1H-苯并咪唑；5-氯-6-(2,3-二氯苯氧基)-2-甲基-1H-苯并咪唑；二氧苯咪唑；三氯苯唑
• 英文名称: triclabendazole
• 英文别名: 5-chloro-6-(2',3'-dichlorophenoxy)-2-methylthiobenzimidazole；5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole；5-chloro-6-(2,3-dichlorophenoxy)-2-methylmercaptobenzimidazole；5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole；TCBZ；6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1H-benzimidazole
• CAS: 68786-66-3
• 化学式: C₁₄H₉Cl₃N₂OS
• mdl: MFCD03147039
• 分子量: 359.663
• InChiKey: NQPDXQQQCQDHHW-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176°C
• 沸点：
  240.6°C (rough estimate)
• 密度：
  1.3875 (rough estimate)
• 溶解度：
  可溶于乙腈（轻微，超声处理），甲醇（轻微）
• 碰撞截面：
  179.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：
  远离火。

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

基于体外研究，三氯苯咪唑主要通过CYP1A2酶（约64%）代谢为其活性代谢物亚砜，其次通过CYP2C9、CYP2C19、CYP2D6、CYP3A和黄素单加氧酶（FMO）进行代谢。这种亚砜代谢物主要通过CYP2C9进一步代谢为活性代谢物砜，其次通过CYP1A1、CYP1A2、CYP1B1、CYP2C19、CYP2D6和CYP3A4进行代谢。

Based on in vitro studies, triclabendazole is mainly metabolized by CYP1A2 enzyme (approximately 64%) into its active _sulfoxide_ metabolite and to a lesser extent by CYP2C9, CYP2C19, CYP2D6, CYP3A, and FMO (flavin containing monooxygenase). This sulfoxide metabolite is further metabolized mainly by CYP2C9 to the active sulfone metabolite, and to a smaller extent by CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2D6, and CYP3A4, _in vitro_.

来源:DrugBank

毒理性

• 肝毒性

三氯苯咪唑在慢性肝片吸虫病中的已发表和历史对照试验很少描述不良事件发生率或血液检测结果，除了嗜酸性粒细胞增多。有描述肝酶升高和黄疸的情况，但慢性肝片吸虫病患者通常会有肝功能测试的轻微升高。此外，治疗的常见副作用最可能是由于肝吸虫从胆道树中突然排出，这可能导致短暂的血清ALT和碱性磷酸酶升高，甚至黄疸。没有报告称在三氯苯咪唑治疗后出现严重肝损伤、急性肝衰竭、消失胆管综合征或慢性肝炎。有报道称与噻苯咪唑和阿苯达唑等其他苯并咪唑驱虫剂相关的胆汁淤积性肝损伤和消失胆管综合征。还有报道称肝片吸虫感染可能导致胆管阻塞和后遗症。

The published and historic controlled trials of triclabendazole in chronic fascioliasis rarely described adverse event rates or blood test results except for eosinophilia. Instances of enzyme elevations and jaundice have been described, but patients with chronic fascioliasis often have minor elevations in liver tests. Furthermore, the common side effects of treatment are most likely due to the effects of sudden expulsion of the liver flukes from the biliary tree, which can result in transient serum ALT and alkaline phosphatase elevations and even jaundice. There are no reports of serious liver injury, acute liver failure, vanishing bile duct syndrome or chronic hepatitis after triclabendazole therapy. There are reports of cholestatic hepatic injury and vanishing bile duct syndrome linked to other benzimidazole anthelmintic agents such as thiabendazole and albendazole. There is also reported association between Fasciola infection with the potential for bile duct obstruction and sequelae.

来源:LiverTox

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用总结：目前没有关于在母乳喂养期间使用三氯苯咪唑的信息。由于药物及其代谢物与蛋白质的结合率为96%至99%，哺乳婴儿的暴露可能性较低。 ◉ 对哺乳婴儿的影响：截至修订日期，没有找到相关的已发布信息。 ◉ 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:No information is available on the use of triclabendazole during breastfeeding. Because of protein binding of 96% to 99% for the drug and metabolites, exposure of the breastfed infant is likely to be low. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

毒理性

• 蛋白质结合

三氯苯咪唑、亚砜代谢物和砜代谢物在人血浆中的蛋白结合率分别为96.7%、98.4%和98.8%。

Protein-binding of triclabendazole, sulfoxide metabolite and sulfone metabolite in human plasma was 96.7%, 98.4% and 98.8% respectively.

来源:DrugBank

吸收、分配和排泄

• 吸收

在给予确诊为肝片吸虫病的患者单次口服剂量为10毫克/千克的三氯苯咪唑，并随560卡路里餐一同服用后，三氯苯咪唑、亚砜代谢物和砜代谢物的平均峰值血浆浓度（Cmax）分别为1.16、38.6和2.29微摩尔/升。三氯苯咪唑、亚砜和砜代谢物的药时曲线下面积（AUC）分别为5.72、386和30.5微摩尔·小时/升。在给肝片吸虫病患者单次口服10毫克/千克剂量的三氯苯咪唑并随560卡路里餐一同服用后，母体化合物以及活性亚砜代谢物的中位Tmax为3到4小时。**食物的影响**当三氯苯咪唑随大约560卡路里的餐食单次给药时，三氯苯咪唑及其亚砜代谢物的Cmax和AUC增加了大约2-3倍。此外，亚砜代谢物的Tmax在禁食受试者中从2小时增加到了进食受试者的4小时。

After a single oral dose of 10 mg/kg triclabendazole with a 560-kcal meal to patients diagnosed with fascioliasis, mean peak plasma concentrations (Cmax) for triclabendazole, the sulfoxide, and sulfone metabolites were 1.16, 38.6, and 2.29 μmol/L, respectively. The area under the curve (AUC) for triclabendazole, the sulfoxide and sulfone metabolites were 5.72, 386, and 30.5 μmol∙h/L, respectively. After the oral administration of a single dose of triclabendazole at 10 mg/kg with a 560 calorie meal to patients with fascioliasis, the median Tmax for the parent compound as well as the active sulfoxide metabolite was 3 to 4 hours. **Effect of Food** Cmax and AUC of triclabendazole and sulfoxide metabolite increased about 2-3 times when triclabendazole was administered as a single dose at 10 mg/kg with a meal containing approximately 560 calories. Additionally, the sulfoxide metabolite Tmax increased from 2 hours in fasting subjects to 4 hours in fed subjects.

来源:DrugBank

吸收、分配和排泄

• 消除途径

在人体中，关于排泄的数据尚不可用。在动物中，三氯苯咪唑主要通过胆道在粪便中排泄（90%），同时伴随着亚砜和砜代谢物。口服剂量的不到10%在尿液中找到排泄。

No data regarding excretion is available in humans. In animals, triclabendazole is primarily excreted by the biliary tract in the feces (90%), together with the sulfoxide and sulfone metabolite. Less than 10% of an oral dose is found excreted in the urine.

来源:DrugBank

吸收、分配和排泄

• 分布容积

喂食后患者中磺酰氧化物代谢物的表观分布容积（Vd）约为1升/千克。

The apparent volume of distribution (Vd) of the sulfoxide metabolite in fed patients is about 1 L/kg.

来源:DrugBank

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险品运输编号：
  HAZARD
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将物品存放在密封容器中，并置于阴凉、干燥的地方。务必确保存储位置远离氧化剂。

SDS

Triclabendazole Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Triclabendazole

Revision number: 5

---

Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Triclabendazole
Percent: >98.0%(LC)(T)
CAS Number: 68786-66-3
Synonyms: 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)benzimidazole , 6-Chloro-5-(2,3-
dichlorophenoxy)-2-(methylthio)benzimidazole
C14H9Cl3N2OS
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

---

Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Triclabendazole

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

---

Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

---

Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Slightly pale yellow red
Odour: No data available
pH: No data available
Melting point/freezing point:176°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available
5.35
Log Pow:
Triclabendazole

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides, Hydrogen
products: chloride

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Section 11. TOXICOLOGICAL INFORMATION
orl-rat LD50:>8 g/kg
Acute Toxicity:
ihl-rat LC50:>500 mg/m3/4H
skn-rat LD50:>4 g/kg
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: cyt-ctl-lym 25 mg/L/48H
sce-ctl-lym 25 mg/L/48H
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available
DD6747000
RTECS Number:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: 5.35
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Triclabendazole

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Triclabendazole (CGA-89317) 是一种苯并咪唑类化合物，能够与微管蛋白结合，损害细胞内运输机制，并干扰蛋白质的合成。

靶点

Target	Value
Tubulin

体外研究

Triclabendazole 治疗羊、奶牛和小母牛后，使它们体内的吸虫虫卵数产量分别下降了15.3%、4.3% 和 36.6%，这些结果表明该农场的绵羊和黄牛体内存在抗 Triclabendazole 肝片吸虫。Triclabendazole 硫氧化物 (50 mg/mL) 对吸虫的作用导致了对 Triclabendazole 敏感的肝片吸虫体壁的大面积破坏，而抗 Triclabendazole 的吸虫仅显示局部和相对少量的覆盖于体刺的体壁被破坏。

体内研究

Triclabendazole 根据给药途径的不同，可以代谢成多种化合物。血药浓度峰值在第18-24小时（Triclabendazole 硫氧化物）和第36-48小时（Triclabendazole 硫酸酯）。在血浆中，未检测到 Triclabendazole 及其代谢物。Triclabendazole 硫氧化物抑制分泌组织从细胞体到表面的运输，并且在高尔基复合体的形成部位发生抑制作用，分别在细胞质连接到合胞体的移动和从基底到合胞体顶端的移动中发挥作用。Triclabendazole 结合到秋水仙碱上的 β-微管蛋白分子的结合位点，这已被用于评估 Triclabendazole 相关活性。

Triclabendazole 以 10 mg/kg 的剂量经瘤胃给药作用于山羊，在血浆中检测到的 Triclabendazole (TCBZ) 代谢物只有 TCBZ 硫氧化物 (TCBZ-SO) 和 TCBZ 硫酸酯，它们分别在第18小时和36小时达到最大浓度（大于13 mg/mL）。Triclabendazole 代谢物特异性结合血浆白蛋白，这会对 TCBZ 代谢物的血药浓度和肝吸虫接触反应产生很大影响。Triclabendazole (40 mg/kg) 经口服给大鼠后可杀死99% 的成年吸虫。

用途

三氯苯达唑是一种驱虫药（片形吸虫），是高效兽用驱虫药。

类别

有毒物质

毒性分级

低毒

急性毒性

• 口服 - 大鼠 LD50: >8000 毫克/公斤
• 口服 - 小鼠 LC50: >8000 毫克/公斤

可燃性危险特性

可燃；火场分解有毒氯化氢、硫氧化物和氮氧化物气体

储运特性

库房低温、通风、干燥

灭火剂

水、二氧化碳、干粉、砂土

反应信息

• 作为反应物：
  描述：

  三氯苯哒唑 在 Iron(III) nitrate nonahydrate 、 氧气 、 三氟乙酸 作用下， 以95 %的产率得到三氯苯达唑亚砜
  参考文献：
  名称：

  一种催化氧化硫醚制备亚砜化合物的方法

  摘要：

  本发明公开了一种新型催化氧化硫醚制备亚砜化合物的方法，所述方法通过催化剂和溶剂的筛选，在非常温和的条件下，有溶剂或无溶剂的条件下实现硫醚公斤级的氧化合成亚砜类化合物。本发明方法兼容烷基‑烷基、烷基‑芳基、芳基‑芳基硫醚及含硫杂环化合物。本发明制备方法具有广泛应用前景。

  公开号：

  CN115772103A
• 作为产物：
  描述：

  二氯-苯酚 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 potassium methanolate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 三氯苯哒唑
  参考文献：
  名称：

  一种动物肝吸虫病药物三氯苯哒唑的制备方法

  摘要：

  本发明涉及一种新型兽药动物肝吸虫病药物三氯苯哒唑的制备方法，以2,3‑二氯苯酚和3,4‑二氯‑5‑硝基苯胺为原料，经过醚化、还原反应、环化和甲基化反应步骤获得三氯苯哒唑。醚化反应步骤，采用碱性更强的乙醇钾或甲醇钾替代了现有技术中的氢氧化钾，并且同时采用微波辐射加热，实现了无需分步制备酚钾盐的步骤，也无需相转移催化剂，通过“一步法”实现醚化反应步骤，并且醚化反应收率可达96%以上，并且产品纯度可达98%以上，满足了工业化应用的需求。

  公开号：

  CN106632067A

文献信息

• [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。
• [EN] ANTHELMINTIC AGENTS AND THEIR USE<br/>[FR] AGENTS ANTHELMINTIQUES ET LEUR UTILISATION
  申请人：INTERVET INT BV

  公开号：WO2010115688A1

  公开（公告）日：2010-10-14

  This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.

  这项发明涉及一般用作驱虫剂或作为制备驱虫剂的中间体的化合物和盐。这项发明还涉及制备这些化合物和盐的方法，包括这些化合物和盐的药物组合物和试剂盒，使用这些化合物和盐制备药物，以及将这些化合物和盐用于需要治疗的动物的治疗方法。
• N-PHENYL-1,1,1-TRIFLUOROMETHANESULFONAMIDE HYDRAZONE DERIVATIVE COMPOUNDS AND THEIR USAGE IN CONTROLLING PARASITES
  申请人：Winzenberg Norman Kevin

  公开号：US20070238700A1

  公开（公告）日：2007-10-11

  Novel N-phenyl-1,1,1-trifluoromethanesulfonamide compounds useful for controlling endo and/or ectoparasites in the environment are provided, together with methods of making the same, and methods of using the inventive compounds to treat parasite infestations in vivo and ex vivo.

  提供了一种用于控制环境中内外寄生虫的新型N-苯基-1,1,1-三氟甲磺酰胺化合物，以及制备这些化合物的方法，以及利用这些创新化合物治疗体内和体外寄生虫感染的方法。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。
• ISOXAZOLINE DERIVATIVES AS INSECTICIDES
  申请人：Pitterna Thomas

  公开号：US20120316124A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 17 , R 18 , R 19 and R 20 are as defined in claim 1 ; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被1至5个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。