烟碱 | 54-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 烟碱
• 中文别名: 尼古丁；(S)-3-(1-甲基-2-吡咯烷基)吡啶；(S)-(-)-烟碱/尼古丁；1-甲基-2-(3-吡啶基)吡咯烷；(S)-(-)-尼古丁
• 英文名称: nicotin
• 英文别名: (S)-3-(1-methylpyrrolidin-2-yl)-pyridine；nicotine；1-methyl-2-(3-pyridyl)pyrrolidine；(S)-3-(1-methyl-2-pyrrolidinyl)pyridine；(S)-nicotine；L-nicotine；3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• CAS: 54-11-5
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: SNICXCGAKADSCV-JTQLQIEISA-N

物化性质

• 稳定性/保质期：

  烟碱是含氮的碱性物质，容易与盐酸反应生成烟碱盐酸盐而溶于水。在提取液中加入强碱NaOH后可使烟碱游离出来。游离烟碱在100℃左右具有一定的蒸气压（约1333帕），因此可通过水蒸气蒸馏法分离提取。烟碱具有碱性，可以使红色石蕊试纸变蓝，也可以使酚酞试剂变红。它还能被KMnO4溶液氧化生成烟酸，并与生物碱试剂作用产生沉淀。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

主要在肝脏中，可替宁是主要的代谢物。

Primarily hepatic, cotinine is the primary metabolite.

来源:DrugBank

代谢

尼古丁的代谢过程在本质上相似，无论是通过尼古丁多聚物口香糖或尼古丁口腔吸入，还是通过吸烟吸入，以及据报道，通过尼古丁经皮系统的应用。尽管尼古丁的确切代谢命运尚未明确建立，但该药物在大约20多种代谢物中被广泛代谢，主要通过肝脏的α-碳氧化和吡咯烷环的N-氧化，分别形成可替宁和尼古丁-1'-N-氧化物。这些代谢物在人类血液中达到吸烟时的浓度时，在药理学上并不活跃；然而，据报道可替宁在动物中具有药理活性，但其同等摩尔浓度下的效力远低于尼古丁。……尼古丁还可能在较小程度上在肾脏和肺部发生代谢。

Metabolism of nicotine is qualitatively similar following buccal absorption from nicotine polacrilex gum or nicotine oral inhalation and from oral inhalation of cigarette smoke, and reportedly following application of nicotine transdermal systems. Although the exact metabolic fate of nicotine is not clearly established, the drug is metabolized extensively to more than 20 metabolites, but principally in the liver via oxidation of the alpha-carbon and N-oxidation of the pyrrolidine ring to cotinine and nicotine-1'-N-oxide, respectively. These metabolites are not pharmacologically active in humans at blood concentrations attained during cigarette smoking; however, cotinine has been reported to be pharmacologically active in animals, but its potency at equivalent molar concentrations is substantially less than that of nicotine. ... Nicotine may also be metabolized to a lesser extent in the kidneys and lungs.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尼古丁-1'-N-氧化物通过大肠中的细菌群落通过N-氧化物还原酶系统还原为尼古丁，随后在肝脏中经历肠肝循环和重复代谢。

Nicotine-1'-N-oxide is reduced to nicotine by bacterial flora in the large intestine via an N-oxide reductase system and subsequently undergoes enterohepatic circulation and repeat metabolism in the liver.

来源:Hazardous Substances Data Bank (HSDB)

代谢

从毒理学的角度来看，有趣的是，微粒体黄素含单加氧酶负责将尼古丁氧化为尼古丁-1'-N-氧化物，而尼古丁氧化为可替宁的过程则由两种酶依次催化：P450和可溶性醛脱氢酶。因此，尼古丁通过两条不同的途径进行代谢，其相对贡献可能会随着外部和内部因素的变化而变化。

Toxicologically, it is of interest that /the microsomal flavin-containing monooxygenase/ is responsible for the oxidation of nicotine to nicotine-1'-N-oxide, whereas the oxidation of nicotine to cotinine is catalyzed by two enzymes acting in sequence: P450 and a soluble aldehyde dehydrogenase. Thus, nicotine is metabolized by two different routes, the relative contributions of which may vary with both the extrinsic and intrinsic factors.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在体外研究中，使用兔肝微粒体、NADPH和O2，发现尼古丁的代谢过程包括羟基化生成5-(3'-吡啶基)-N-甲基吡咯烷-2-醇；氧化生成可替宁；以及可替宁的去氨化生成4-(3'-吡啶基)-4-甲基氨基丁酸。没有观察到二氧化碳的产生。

In vitro studies with rabbit liver microsomes, /NADPH/, and O2, indicated that metabolism of nicotine proceeded through hydroxylation to 5-(3'-pyridyl)-n-methylpyrrolidine-2-ol; oxidation to cotinine; and deamidation of cotinine to 4-(3'-pyridyl)-4-methylamino-butyric acid. No carbon dioxide was observed.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 肝毒性

尼古丁用于戒烟计划以及含有尼古丁的电子烟在治疗期间并未与血清酶水平升高有关，其发生率并未超过安慰剂。尼古丁的医疗和娱乐用途并未与临床上明显的肝损伤病例有关联。

Nicotine used in cigarette cessation programs as well as nicotine containing e-cigarettes have not been associated with serum enzyme elevations during therapy at rates greater than occurred with placebo. Medical and recreational uses of nicotine have not been associated with cases of clinically apparent liver injury.

来源:LiverTox

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用概述：此记录中的信息仅指尼古丁作为戒烟替代产品的使用。使用21毫克的透皮贴片时，尼古丁进入母乳的量相当于每天吸烟17支香烟。7毫克和14毫克较低剂量的贴片为哺乳婴儿提供的尼古丁量按比例降低。尚未有关于哺乳期母亲使用尼古丁喷雾或尼古丁口香糖的研究报告。使用尼古丁喷雾后，母体血浆尼古丁浓度约为吸烟者的三分之一，因此乳汁中的浓度可能按比例降低。使用尼古丁口香糖后，母体尼古丁血浆浓度因咀嚼的力度和每天咀嚼的数量而有所不同，但可能与吸烟香烟后达到的浓度相似。一个来源建议使用作用时间较短的制剂而不是贴片。 有些人主张在吸烟的母亲中使用尼古丁替代产品，以减少母乳喂养婴儿吸入烟雾和母体香烟烟雾中毒素的风险。然而，其他人指出，基于动物数据，尼古丁可能增加婴儿猝死综合症的风险，并可能干扰婴儿正常肺部的发育。这些作者建议哺乳期母亲不要使用任何形式的尼古丁。尚未有研究来解决这些问题。在哺乳期间，可能更愿意使用另一种戒烟产品。 ◉ 对母乳喂养婴儿的影响：母体吸烟是婴儿猝死综合症（SIDS）的主要危险因素。认为尼古丁是致病因素，因为它减少了颈动脉体的多巴胺含量，并减少了婴儿在缺氧发作期间自我复苏的能力。 吸烟者母乳中的尼古丁似乎也降低了男性母乳喂养婴儿的心率变异性。 在一项研究中，5位使用21毫克尼古丁贴片戒烟的母亲所生的婴儿，其平均丹佛发展年龄与其实际年龄相当。 ◉ 对泌乳和母乳的影响：吸烟会减少乳汁产量。这种效应可能是由尼古丁引起的，因为尼古丁降低了血清催乳素，尽管吸烟的其他因素也可能发挥作用。 在一项研究中，15位使用尼古丁贴片的哺乳期母亲在几周内将剂量从21毫克逐渐减少到14毫克再到7毫克，她们的平均乳汁产量比文献平均数值低17%。然而，该研究并未直接比较吸烟者与非吸烟者的乳汁产量。在这项研究中，母亲使用尼古丁贴片期间婴儿的乳汁摄入量与吸烟期间相似。

◉ Summary of Use during Lactation:Information in this record refers only to the use of nicotine as a replacement product for smoking cessation. With a 21 mg transdermal patch, nicotine passes into breastmilk in amounts equivalent to smoking 17 cigarettes daily. Lower patch strengths of 7 and 14 mg provide proportionately lower amounts of nicotine to the breastfed infant. No studies on nicotine spray or nicotine gum use in nursing mothers have been reported. Maternal plasma nicotine concentrations after using the nicotine spray are about one-third those of smokers, so milk concentrations are probably proportionately less. Maternal nicotine plasma concentrations after using nicotine gum are variable depending on the vigor of chewing and number of pieces chewed daily, but can be similar to those attained after smoking cigarettes. One source recommends the shorter acting agents over the patches. Some have advocated use of nicotine replacement products in smoking mothers to reduce the risk to breastfed infants of inhaled smoke and toxins in maternal cigarette smoke. However, others point out that based on animal data, nicotine may increase the risk of sudden infant death syndrome and might interfere with normal infant lung development. These authors recommend against using any form of nicotine in nursing mothers. No studies have been performed to resolve these issues. An alternate smoking cessation product may be preferred during nursing. ◉ Effects in Breastfed Infants:Maternal smoking is a major risk factor for sudden infant death syndrome (SIDS). Nicotine is thought to be the causative factor by reducing the dopamine content of the carotid bodies and reducing the infant's ability to autoresuscitate during hypoxic episodes. Nicotine in the breastmilk of smokers also appears to reduce the heart rate variability in male breastfed infants. In a study of the infants of 5 mothers who were using 21 mg nicotine patches for smoking cessation, the infants' average Denver Developmental age was equivalent to their chronological age. ◉ Effects on Lactation and Breastmilk:Cigarette smoking reduces milk yield. This effect may be caused by nicotine which lowers serum prolactin, although other factors associated with smoking may also play a role. In a study of 15 nursing mothers who were using nicotine patches in decreasing doses from 21 mg to 14 mg to 7 mg over several weeks, their average milk production was 17% lower than average literature values as judged by infant milk intake. The study did not directly compare the milk production of smokers to nonsmokers, however. In this study, infant milk intake during maternal use of the nicotine patch was similar to that during smoking.

来源:Drugs and Lactation Database (LactMed)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

恶心、唾液分泌过多、腹痛、呕吐、腹泻；头痛、眩晕、听力、视觉障碍；混乱、乏力（虚弱、疲劳）、不协调；心律不齐；抽搐、呼吸困难（呼吸困难）；在动物中：致畸作用。

nausea, salivation, abdominal pain, vomiting, diarrhea; headache, dizziness, hearing, visual disturbance; confusion, lassitude (weakness, exhaustion), incoordination; cardiac arrhythmias; convulsions, dyspnea (breathing difficulty); In Animals: teratogenic effects

来源:The National Institute for Occupational Safety and Health (NIOSH)

吸收、分配和排泄

• 吸收

通过口腔黏膜吸收的尼古丁速度相对较慢，吸入剂使用时不会出现像吸烟时那样尼古丁在动脉血浆中的高浓度快速上升随后下降的情况。大约10%被吸收的尼古丁以原形从尿液中排出。

Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.

来源:DrugBank

吸收、分配和排泄

• 消除途径

大约10%的吸收尼古丁以原形从尿液中排出。

About 10% of the nicotine absorbed is excreted unchanged in the urine.

来源:DrugBank

吸收、分配和排泄

• 分布容积

每千克2到3升

2 to 3 L/kg

来源:DrugBank

吸收、分配和排泄

• 清除

1.2 升/分钟 [健康成年吸烟者]

1.2 L/min [healthy adult smoker]

来源:DrugBank

吸收、分配和排泄

尼古丁容易通过呼吸道、口腔粘膜和皮肤吸收。……尼古丁及其代谢物通过肾脏迅速排出。尼古丁的尿液排泄速率取决于尿液的pH值；当尿液呈碱性时，排泄量减少。吸烟的哺乳期妇女也会通过乳汁排出尼古丁。重度吸烟者的乳汁中可能含有0.5毫克/升。……显然，由于胃排空减慢，通过口腔摄入的烟草中的尼古丁吸收会延迟，因此呕吐可能会排出胃肠道中残留的大部分烟草。

Nicotine is readily absorbed from respiratory tract, buccal mucous membranes, and skin. ... Both nicotine and its metabolites are rapidly eliminated by the kidneys. The rate of urinary excretion of nicotine is dependent upon pH of urine; excretion diminishes when urine is alkaline. Nicotine is also excreted in milk of lactating women who smoke. Milk of heavy smokers may contain 0.5 mg/L. ...Apparently the gastric absorption of nicotine from tobacco taken by mouth is delayed because of slowed gastric emptying, so that vomiting may remove much of the tobacco remaining in GI tract.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

烟碱在烟草中含量平均达4%，主要以柠檬酸盐或苹果酸盐形式存在。工业上可通过制废料，利用水蒸气蒸馏简单提取。

合成制备方法

1. 烟碱的工业化制取方法有三种：蒸馏法、离子交换树脂法和萃取法。其基本生产流程如下：

   • 蒸馏法：将碱液加入烟叶中，通入过热水蒸气进行蒸馏，馏出水分含有游离烟碱。
   • 离子交换法：直接用清水浸泡烟叶，过滤后得到烟碱的水溶液。然后将此水溶液流经强酸性离子交换树脂柱，烟碱被富集在树脂上，再用碱液进行交换，即可获得游离烟碱的水溶液。
   • 萃取法：使用石灰乳直接中和清水浸泡后的烟叶，过滤后的清液即为含有烟碱的有机酸水溶液。通过有机溶剂萃取出烟碱，再用30%硫酸水溶液反萃该有机相，得到硫酸烟碱水溶液后浓缩至40%，然后用碱处理、常压蒸发多余水分，并进行减压蒸馏，最终可获得纯度大于95%的烟碱。

2. 烟碱是烟草中的一种主要生物碱，已发现存在于茄科烟草属植物中，主要有两种品种：烟草（Nicotiana tabacum）和黄花烟草（Nicotiana rustica）。其制备方法如下：

   • 第一种方法：烟草-稀酸浸渍-碱中和-水蒸气蒸馏-草酸处理-碱化而得。
   • 第二种方法：烟叶-磨研或用卷烟厂副产烟末-石灰乳碱化-煤油过滤。

反应信息

• 作为反应物：
  描述：

  烟碱 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 以97%的产率得到5'-氰基烟碱
  参考文献：
  名称：

  [EN] NICOTINE COMPOUNDS AND ANALOGS THEREOF, SYNTHETIC METHODS OF MAKING COMPOUNDS, AND METHODS OF USE
  [FR] COMPOSÉS DE NICOTINE ET LEURS ANALOGUES, PROCÉDÉS DE SYNTHÈSE POUR FABRIQUER LES COMPOSÉS ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2012031220A3
• 作为产物：
  描述：

  在 (p-cymene)ruthenium(II) chloride 、 (R)-(-)-2,2′-bis-[di(3,5-diisopropyl-4-dimethylaminophenyl)phosphine]-6,6′-dimethoxy-1,1′-biphenyl 、 potassium formate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以95%的产率得到
  参考文献：
  名称：

  一种具有光学活性的尼古丁的制备方法

  摘要：

  本发明公开了一种具有光学活性的尼古丁的制备方法，其步骤为：将含氮或含磷的手性配体和金属催化剂加入有机溶剂中，进行催化剂制备；依次加入亚胺盐和还原剂进行还原反应；加入萃取剂，提取尼古丁化合物。本发明的制备方法，采用亚胺盐衍生物作为前驱体，起始原料成本低廉、反应条件温和(如，常温附近温度范围内进行催化、还原反应)，且催化剂和还原剂均为常见的化学物质，终产物尼古丁的合成收率及化学纯度都高，便于实现大规模工业生产。

  公开号：

  CN111233829A
• 作为试剂：
  描述：

  dimercury(2+) 在 烟碱 作用下， 以 not given 为溶剂， 生成 汞
  参考文献：
  名称：

  Burkat, S. E.; Skrynnik, E. N.; Jaroslovskaja, S. S., Zhurnal Analiticheskoi Khimii, 1951, vol. 6, p. 325 - 327

  摘要：

  DOI：

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• [EN] AZA PYRIDONE ANALOGS USEFUL AS MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS<br/>[FR] ANALOGUES D'AZAPYRIDONE UTILES COMME ANTAGONISTES DU RÉCEPTEUR 1 DE L'HORMONE CONCENTRANT LA MÉLANINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010104818A1

  公开（公告）日：2010-09-16

  MCHR1 antagonists are provided having the following Formula (I): A1 and A2 are independently C or N; E is C or N; Q1, Q2, and Q3 are independently C or N provided that at least one of Q1, Q2, and Q3 is N but not more than one of Q1, Q2, and Q3 is N; D1 is a bond, -CR8R9 X-, -XCR8R9-, -CHR8CHR9-, -CR10=CR10'-, -C≡C-, or 1,2-cyclopropyl; X is O, S or NR11; R1, R2, and R3 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower cycloalkyl, -CF3, -OCF3, -OR12 and -SR12; G is O, S or -NR15; D2 is lower alkyl, lower cycloalkyl, lower alkylcycloalkyl, lower cycloalkylalkyl, lower cycloalkoxyalkyl or lower alkylcycloalkoxy or when G is NR15, G and D2 together may optionally form an azetidine, pyrrolidine or piperidine ring; Z1 and Z2 are independently hydrogen, lower alkyl, lower cycloalkyl, lower alkoxy, lower cycloalkoxy, halo, -CF3, -OCONR14R14', -CN, -CONR14R14', -SOR12, -SO2R12, -NR14COR14', -NR14CO2R14', -CO2R12, NR14SO2R12 or COR12; R5, R6, and R7 are independently selected from the group consisting of hydrogen lower alkyl, lower cycloalkyl, -CF3, -SR12, lower alkoxy, lower cycloalkoxy, -CN, -CONR14R14', SOR12, SO2R12, NR14COR14', NR14CO2R12, CO2R12, NR14SO2R12 and -COR12; R8, R9, R10, R10', R11 are independently hydrogen or lower alkyl; R12 is lower alkyl or lower cycloalkyl; R14 and R14' are independently H, lower alkyl, lower cycloalkyl or R14 and R14' together with the N to which they are attached form a ring having 4 to 7 atoms; and R15 is independently selected from the group consisting of hydrogen and lower alkyl. Such compounds are useful for the treatment of MCHR1 mediated diseases, such as obesity, diabetes, IBD, depression, and anxiety.

  MCHR1拮抗剂具有以下化学式（I）：A1和A2独立地为C或N；E为C或N；Q1、Q2和Q3独立地为C或N，但至少其中一个为N，但不超过一个为N；D1为键，-CR8R9 X-，-XCR8R9-，-CHR8CHR9-，-CR10=CR10'-，-C≡C-，或1,2-环丙基；X为O、S或NR11；R1、R2和R3独立地从氢、卤素、低烷基、低环烷基、-CF3、-O 、-OR12和-SR12组成的群体中选择；G为O、S或-NR15；D2为低烷基、低环烷基、低烷基环烷基、低环烷基烷基、低环烷氧基烷基或低烷基环烷氧基，或当G为NR15时，G和D2一起可以选择形成氮杂环丙烷、吡咯烷或哌啶环；Z1和Z2独立地为氢、低烷基、低环烷基、低烷氧基、低环烷氧基、卤素、- 、-OCONR14R14'、-CN、-CONR14R14'、-SOR12、-SO2R12、-NR14COR14'、-NR14CO2R14'、-CO2R12、NR14SO2R12或COR12；R5、R6和R7独立地从氢、低烷基、低环烷基、- 、-SR12、低烷氧基、低环烷氧基、-CN、-CONR14R14'、SOR12、SO2R12、NR14COR14'、NR14CO2R12、CO2R12、NR14SO2R12和-COR12组成的群体中选择；R8、R9、R10、R10'、R11独立地为氢或低烷基；R12为低烷基或低环烷基；R14和R14'独立地为H、低烷基、低环烷基或R14和R14'与其连接的N一起形成具有4至7个原子的环；R15独立地从氢和低烷基组成的群体中选择。这些化合物对于治疗MCHR1介导的疾病，如肥胖症、糖尿病、炎症性肠病、抑郁症和焦虑症非常有用。
• [EN] QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS<br/>[FR] COMPOSÉS QUINUCLIDINE EN TANT QUE LIGANDS DU RÉCEPTEUR NICOTINIQUE ALPHA-7 DE L'ACÉTYLCHOLINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016073407A1

  公开（公告）日：2016-05-12

  There are disclosed a series of quinuclidines having the Formula (I). which bind to the nicotinic α7 receptor and may be useful for the treatment of disorders of the central nervous system.

  揭示了一系列具有化学式（I）的喹诺啉类化合物，它们与尼古丁型α7受体结合，可能对中枢神经系统疾病的治疗有用。
• [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。

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