埃玛菌素 | 119791-41-2

• 物质功能分类: 化学农药原药 - 杀虫剂 - 其他杀虫剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 埃玛菌素
• 中文别名: 甲氨基阿维菌素；依马菌素；埃玛菌素(因灭汀)
• 英文名称: emamectin B1a
• 英文别名: (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-4-methoxy-5-[(2S,4S,5S,6S)-4-methoxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
• CAS: 119791-41-2
• 化学式: C₄₉H₇₅NO₁₃
• 分子量: 886.1
• InChiKey: CXEGAUYXQAKHKJ-NSBHKLITSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷（少许）、氯仿（少许）、甲醇（少许）
• 颜色/状态：
  White to off-white powder
• 熔点：
  141-146 °C /Emamectin benzoate/
• 密度：
  1.20 at 23 °C /Emamectin benzoate/
• 蒸汽压力：
  3.8X10-8 mm Hg at 21 °C /Emamectin benzoate/
• 旋光度：
  Specific optical rotation: -6.9 deg (c = 0.5% in methanol)
• 分解：
  When heated to decomposition it emits toxic vapors of /Nitrogen oxide/.
• 解离常数：
  pKa: 4.18 (acidic, attributed to benzoate counter ion), 8.71 (basic, attributed to emamectin moiety)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  63
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  14

ADMET

代谢

大西洋鲑鱼（约1.3公斤）在5±1摄氏度的海水罐中饲养，通过饲料以50微克/公斤/天的名义剂量给予[(3)H]依马美汀B1苄酯，连续7天。在最终剂量后的3小时和12小时以及1、3、7、15、30、45、60和90天，从每组10条鱼中收集组织、血液和胆汁。从最终剂量前的罐中开始，每天收集粪便，直到最终剂量后的90天。在给药期间，每日粪便样本的总放射性残留物（TRR）最大为0.25 ppm，且在覆盖给药期的合并粪便中，大于97%的TRR是依马美汀B1a。粪便TRR随后迅速下降，到最终剂量后1天大约降至0.05 ppm。90天给药期间组织的平均TRR范围如下：肾脏，1.4-3 ppm；肝脏，1.0-2.3 ppm；皮肤，0.04-0.09 ppm；肌肉，0.02-0.06 ppm；骨骼，小于0.01 ppm。按给药间隔合并的肝脏、肾脏、肌肉和皮肤样本的残留物组成为依马美汀B1a（81-100% TRR）和去甲基依马美汀B1a（0-17% TRR），在一些肌肉样本中可见到N-甲酰依马美汀B1a的微量（小于2%）。选作依马美汀残留监管监测的标志残留物是依马美汀B1a。使用高效液相色谱-荧光法在个体皮肤和肌肉样本中定量依马美汀B1a水平，在所有分析的样本中（给药后3小时至30天），均低于85 ppb。

Atlantic salmon (approximately 1.3 kg) maintained in tanks of seawater at 5 +/- 1 degrees C were dosed with [(3)H]emamectin B1 benzoate in feed at a nominal rate of 50 ug of emamectin benzoate/kg/day for 7 consecutive days. Tissues, blood, and bile were collected from 10 fish each at 3 and 12 hr and at 1, 3, 7, 15, 30, 45, 60, and 90 days post final dose. Feces were collected daily from the tanks beginning just prior to dosing to 90 days post final dose. The total radioactive residues (TRR) of the daily feces samples during dosing were 0.25 ppm maximal, and >97% of the TRR in pooled feces covering the dosing period was emamectin B1a. Feces TRR then rapidly declined to approximately 0.05 ppm by 1 day post final dose. The ranges of mean TRR for tissues over the 90 days post dose period were as follows: kidney, 1.4-3 ppm; liver, 1.0-2.3 ppm; skin, 0.04-0.09 ppm; muscle, 0.02-0.06 ppm; and bone, <0.01 ppm. The residue components of liver, kidney, muscle, and skin samples pooled by post dose interval were emamectin B1a (81-100% TRR) and desmethylemamectin B1a (0-17% TRR) with N-formylemamectin B1a seen in trace amounts (<2%) in some muscle samples. The marker residue selected for regulatory surveillance of emamectin residues was emamectin B1a. The emamectin B1a level was quantified in individual samples of skin and muscle using HPLC-fluorometry and was below 85 ppb in all samples analyzed (3 hr to 30 days post dose).

来源:Hazardous Substances Data Bank (HSDB)

代谢

...已鉴定出一个哺乳动物代谢物。这种代谢物被特征化为乙螨唑的N-去甲基化副产物。

...a single mammalian metabolite has been identified. This metabolite is characterized as an N-demethylation byproduct of emamectin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

(3)H/(14)C-标记的4"-脱氧-4"-表甲基氨基阿维菌素B1a（MAB1a）苄酸盐的代谢，这是阿维菌素类杀虫剂埃玛菌素苄酸盐的主要同系物（≥90%），在产蛋鸡中进行了研究。十只 Leghorn 母鸡（Gallus domesticus）每天一次口服给药，连续7天（1毫克/千克体重/天）。每天收集鸡蛋和排泄物，然后将鸡蛋分离成蛋白和蛋黄。在最后一次给药后20小时内，鸡被安乐死，收集肝脏、肾脏、心脏、肌肉、脂肪、卵巢、肌胃、胃肠道及其内容物和胴体。大约70%和6%的总给药剂量分别在排泄物加胃肠道及其内容物和 组织加鸡蛋中回收。确定了两种新的代谢物，即原化合物的24-羟甲基衍生物（24-羟甲基-4"-脱氧-4"-表甲基氨基阿维菌素B1a）和24-羟甲基-4"-脱氧-4"-表甲基氨基阿维菌素B1a的N-去甲基衍生物（24-羟甲基-4"-脱氧-4"-表氨基阿维菌素B1a）。此外，还分离并鉴定了这两种代谢物的八个脂肪酸共轭物，它们在组织和鸡蛋中的总放射性残留物中占8-75%。尽管这代表了对异生物的体内脂肪酸共轭作用的最广泛研究之一，但人们通过食用鸡肉对MAB1a残留的潜在暴露极低，因为本研究的剂量水平大约是作物中MAB1a残留水平的1000倍，而且大部分应用的剂量在排泄物中回收。根据这些发现，MAB1a的鸟类生物转化与哺乳动物的生物转化有显著差异。

The metabolism of (3)H/(14)C-labeled 4"-deoxy-4"-epimethylaminoavermectin B1a (MAB1a) benzoate, the major homologue (>/=90%) of the avermectin insecticide emamectin benzoate, was studied in laying chickens. Ten Leghorn hens (Gallus domesticus) were orally dosed once daily for 7 days (1 mg/kg of body weight/day). Eggs and excreta were collected daily, and eggs were subsequently separated into whites and yolks. Chickens were euthanized within 20 hr after the last dose, and liver, kidney, heart, muscle, fat, ovaries, gizzard, gastrointestinal tract and contents, and carcass were collected. Approximately 70 and 6% of the total administered dose were recovered in the excreta plus gastrointestinal tract and contents and in the tissues plus eggs, respectively. Two novel metabolites, i.e. the 24-hydroxymethyl derivative of the parent compound (24-hydroxymethyl-4"-deoxy-4"-epimethylaminoavermectin B1a) and the N-demethylated derivative of 24-hydroxymethyl-4"-deoxy-4"-epimethylaminoavermectin B1a (24-hydroxymethyl-4"-deoxy-4"-epiaminoavermectin B1a), were identified. In addition, eight fatty acid conjugates of each of these two metabolites, comprising 8-75% of total radioactive residues in tissues and eggs, were isolated and identified. Although this represents some of the most extensive in vivo fatty acid conjugation to a xenobiotic reported to date, potential human exposure to MAB1a residues from consumption of chicken would be extremely low, because the dosage level in this study was approximately 1000-fold greater than the MAB1a residue levels seen in crops and because the majority of the applied dose was recovered in the excreta. Based on these findings, the avian biotransformation of MAB1a differs substantially from the mammalian biotransformation.

来源:Hazardous Substances Data Bank (HSDB)

代谢

苄氨基阿维菌素是一种杀虫剂，用于防治水果和蔬菜等农作物上的害虫。它通过干扰害虫神经系统的正常功能，导致害虫死亡。虽然苄氨基阿维菌素在哺乳动物体内不会广泛代谢，但有限的代谢信息表明，代谢过程并不会导致苄氨基阿维菌素的解毒。事实上，苄氨基阿维菌素在植物中的一种代谢产物比其本身更具毒性。

While emamectin benzoate is not extensively metabolized in mammals, the limited information on the metabolites of emamectin benzoate suggests that metabolism does not result in the detoxification of emamectin benzoate. One plant metabolite of emamectin benzoate is somewhat more toxic than emamectin benzoate itself.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

它具有在水中低溶解度，并且有广泛的非特异性结合。它打开了对GABA不敏感的氯离子通道，降低膜电阻并增加内向电导。

It has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. (T10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列在IARC目录中。

Not listed by IARC.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

阿维菌素具有神经毒性，并且对生殖和发育有影响。

Avermectins are neurotoxic and have reproductive and developmental effects. (L1826)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

阿维菌素会导致皮肤和眼睛刺激，中枢神经系统抑制（不协调、震颤、乏力、兴奋、瞳孔扩大、昏迷），呕吐，抽搐和/或震颤，以及在高剂量下的呼吸衰竭。

Avermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses. (L1826)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 相互作用

家蝇（Musca domestica L.）是全球乳品作业的重要害虫，能够适应广泛的环境条件。目前有多种杀虫剂用于它们的防治，但抗药性的发展是一个严重的问题。杀虫剂混合使用可以提高杀虫剂对具有抗性的害虫的毒性，因此可能成为一种潜在的害虫抗药性管理工具。本研究评估了单独使用以及混合使用时， bifenthrin（联苯菊酯）、cypermethrin（氯氰菊酯）、deltamethrin（溴氰菊酯）、chlorpyrifos（毒死蜱）、profenofos（丙氟磷）、emamectin benzoate（甲氨基阿维菌素苯甲酸盐）和fipronil（氟虫腈）对家蝇的毒性。与实验室敏感品系相比，现场收集的家蝇群体对所有调查的杀虫剂均表现出显著抗性。大多数杀虫剂混合物，如将一种拟除虫菊酯与其他化合物混合，在两种条件下（1:1-"A"和LC50:LC50-"B"）显著提高了拟除虫菊酯对现场群体的毒性。在两种条件下，拟除虫菊酯与其他化合物的组合指数在大多数情况下显著低于1，表明有协同作用。当酶抑制剂PBO和DEF与杀虫剂联合用于抗性群体时，bifenthrin、cypermethrin、deltamethrin和emamectin的毒性显著提高，这表明存在酯酶和单加氧酶基础的抗性机制。通过将bifenthrin、cypermethrin和deltamethrin与chlorpyrifos、profenofos、emamectin和fipronil联合使用，可以增强这些杀虫剂对家蝇抗性群体的毒性。目前的研究结果可能对家蝇抗性管理具有实际意义。

House flies, Musca domestica L., are important pests of dairy operations worldwide, with the ability to adapt wide range of environmental conditions. There are a number of insecticides used for their management, but development of resistance is a serious problem. Insecticide mixtures could enhance the toxicity of insecticides in resistant insect pests, thus resulting as a potential resistance management tool. The toxicity of bifenthrin, cypermethrin, deltamethrin, chlorpyrifos, profenofos, emamectin benzoate and fipronil were assessed separately, and in mixtures against house flies. A field-collected population was significantly resistant to all the insecticides under investigation when compared with a laboratory susceptible strain. Most of the insecticide mixtures like one pyrethroid with other compounds evaluated under two conditions (1?1-"A" and LC50: LC50-"B") significantly increased the toxicity of pyrethroids in the field population. Under both conditions, the combination indices of pyrethroids with other compounds, in most of the cases, were significantly below 1, suggesting synergism. The enzyme inhibitors, PBO and DEF, when used in combination with insecticides against the resistant population, toxicities of bifenthrin, cypermethrin, deltamethrin and emamectin were significantly increased, suggesting esterase and monooxygenase based resistance mechanism. The toxicities of bifenthrin, cypermethrin and deltamethrin in the resistant population of house flies could be enhanced by the combination with chlorpyrifos, profenofos, emamectin and fipronil. The findings of the present study might have practical significance for resistance management in house flies.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有两个给药组，每组有2只雄性比格犬。第1组在第1天接受0.5 mg/kg的(3)H-MK-0243苯甲酸盐（1 mL/kg在5%乙醇中……0.239 mCi/mg；98.8%放射化学纯度），在第15天接受0.5 mg/kg的(3)H-MK-0243 HCl（1 mL/kg在去离子水中……0.229 mCi/mg；98.7%放射化学纯度）。第2组的给药顺序相反。每次给药前测定体重。在每次给药后的0.5、1、2、4、6、8、24、48、96和168小时，各取2 mL血液用于药物水平测定。在0至24小时和72至96小时收集尿液和粪便用于药物水平分析。没有发现药物效果的证据。苯甲酸盐和HCl盐的平均血浆半衰期分别为35.7 +/- 3.4小时和35.5 +/- 4.4小时。苯甲酸盐和HCl盐的平均血浆近似曲线下面积（AUC）分别为4479 +/- 1476和4574 +/- 1514 ng/g血浆/7天。两种盐的主要成分MK-0243的MAB1a平均血浆峰值水平约为100 ng当量/g血浆，在大约6小时出现。在第1天和第4天，粪便和尿液的总回收率分别约为40%和0.01%的剂量。结论是，这两种盐在雄性比格犬中是生物等效的。

There were 2 dosing groups, each consisting of 2 male beagles. Group 1 received 0.5 mg/kg of (3)H-MK-0243 benzoate (1 mL/kg in 5% ethanol ... 0.239 mCi/mg; 98.8% radiochemically pure) on day 1 and 0.5 mg/kg of (3)H-MK-0243 HCl (1 mL/kg in deionized water ... 0.229 mCi/mg; 98.7% radiochemically pure) on day 15. Dosing was reversed for Group 2. Body weights were determined before each dose. 2 mL of blood was withdrawn for drug level determinations following each dose at 0.5, 1, 2, 4, 6, 8, 24, 48, 96 and 168 hr. Urine and feces were collected for drug level analysis at 0 to 24 and 72 to 96 hr. There was no evidence of drug effects. The mean plasma half lives for the benzoate and HCl salts were 35.7 +/- 3.4 hr and 35.5 +/- 4.4 hr, respectively. The mean plasma approximate area under the curve (AUC) for the benzoate and HCl salts was 4479 +/- 1476 and 4574 +/- 1514 ng/g plasma/7days. The mean peak plasma MAB1a (the major component of MK-0243 at 90 to 95%) levels were ~100 ng equivalents/g plasma, occurring at ~6 hr for either salt. Combined fecal and urine recoveries during the 1st and 4th days were ~40% and 0.01% of the dose, respectively. It is concluded that the 2 salts are bioequivalent in male beagle dogs.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

实验性杀虫剂阿维菌素本贝酸盐的皮肤吸收在猕猴身上进行了研究。通过比较皮肤应用化合物的排泄物中放射性水平与等效静脉注射剂量后的放射性水平来计算皮肤吸收。给三只猴子静脉注射300微克(3)H-MAB1a(以丙二醇：盐水1:1溶液制备)后，血浆水平呈双相下降，放射性在最初的15分钟内迅速下降，随后较慢下降至背景水平。在给药后7天，大约90%和5%的给药放射性分别从粪便和尿液中回收。经过一段清洗期后，将300微克[(3)H]MAB1a(溶解在可乳化浓缩物中)涂在前臂剃毛的同一只猴子身上。经过10小时的暴露期后，大约90%的放射性通过肥皂和水清洗暴露的前臂回收。尽管血浆放射性水平通常保持在背景水平以下，但大约1.5%的给药剂量在排泄物中回收。阿维菌素本贝酸盐的皮肤吸收计算为1.6%。阿维菌素本贝酸盐的低皮肤渗透性表明，农业工作者实际接触该化合物的可能性极小。

The dermal absorption of the experimental avermectin insecticide emamectin benzoate was studied in the Rhesus monkey. Dermal absorption was calculated by comparing radioactivity levels in excreta following dermal application of the compound with those following administration of an equivalent intravenous dose. After iv administration of 300 ug (3)H-MAB1a (prepared as a 1:1 solution of propylene glycol:saline) to three monkeys, plasma levels decreased biphasically with a rapid decline in radioactivity during the first 15 min followed by a slower decline to background. By 7 days post-dose, approximately 90% and 5% of the administered radioactivity was recovered in the feces and urine, respectively. After a washout period, 300 micrograms [(3)H]MAB1a (dissolved in emulsifiable concentrate) was applied topically to the shaved forearm of the same monkeys. Following a 10-hr exposure period, approximately 90% of the radioactivity was recovered in a soap and water wash of the exposed forearms. Although plasma radioactivity levels generally remained below background levels, approximately 1.5% of the applied dose was recovered in the excreta. Dermal absorption of [()3H]emamectin benzoate was calculated as 1.6%. The low dermal penetration of emamectin benzoate indicates that minimal actual exposure of agricultural workers to this compound will occur.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

本研究的目标是调查在推荐剂量给药后血液、粘液和肌肉中的埃马霉素含量，以及与同一条鱼上的海虱感染的相关性（消除研究）。通过全身自动射线摄影和闪烁计数法，还研究了单次口服剂量后大西洋鲑鱼体内三标埃马霉素苄酯的分布情况（分布研究）。在消除研究中，埃马霉素苄酯的浓度在第7天（给药的最后一天）达到最高，分别为血液128、粘液105和肌肉68纳克/克（p.p.b.）。从第7天开始，血液中的浓度下降，直到第77天浓度低于检测限。除了第7天和第21天，粘液中的浓度高于血浆（P < 0.05）。埃马霉素苄酯的浓度从治疗结束（第7天）到第70天逐渐下降，肌肉、血浆和粘液的半衰期分别为9.2、10.0和11.3天。分布研究表明，在整个观察期（56天）内，粘膜（胃肠道、鳃）中的放射性活性很高。在整个研究期间，松果体、垂体和嗅球的活性很高。胆汁中的活性最高，表明这是排泄的重要途径。分布研究确认了消除研究中关于血液、皮肤粘液和肌肉浓度的结果。

The aims of this study were to investigate the content of emamectin in blood, mucus and muscle following field administration of the recommended dose, and correlation with sea lice infection on the same fish (elimination study). The tissue distribution of tritiated emamectin benzoate after a single oral dose in Atlantic salmon was also investigated by means of whole-body autoradiography and scintillation counting (distribution study). In the elimination study, concentrations of emamectin benzoate reached maximum levels of 128, 105 and 68 ng/g (p.p.b.) for blood, mucus and muscle respectively, on day 7, the last day of administration. From day 7, the concentration in the blood declined until concentration was less than the limit of detection on day 77. The concentration was higher in mucus compared with plasma (P < 0.05) except on days 7 and 21. The concentration of emamectin benzoate decreased gradually from the end of treatment (day 7) to day 70 with half-lives of 9.2, 10.0 and 11.3 days in muscle, plasma and mucus respectively. The distribution study demonstrated a high quantity of radioactivity in mucous membranes (gastrointestinal tract, gills) throughout the observation period (56 days). Activity was high in the epiphysis, hypophysis and olfactory rosette throughout the study. The highest activity was observed in the bile, indicating this to be an important route for excretion. The distribution study confirmed the results from the elimination study with respect to concentrations in blood, skin mucous and muscle.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大西洋鲑鱼（约1.3公斤）在5±1摄氏度的海水罐中饲养，通过饲料以名义上的50微克/公斤/天的剂量给予3H-依马美汀B1苄酯，连续7天。在最终剂量后的3小时和12小时以及1、3、7、15、30、45、60和90天，从每组10条鱼中收集组织、血液和胆汁。从最终剂量前开始，每天从罐中收集粪便，直到最终剂量后的90天。在给药期间，每日粪便样本的总放射性残留物（TRR）最大为0.25 ppm，且在覆盖给药期的合并粪便中，大于97%的TRR是依马美汀B1a。粪便TRR随后迅速下降，到最终剂量后1天大约降至0.05 ppm。90天给药期间组织的平均TRR范围如下：肾脏，1.4-3 ppm；肝脏，1.0-2.3 ppm；皮肤，0.04-0.09 ppm；肌肉，0.02-0.06 ppm；骨骼，小于0.01 ppm。按给药间隔合并的肝脏、肾脏、肌肉和皮肤样本的残留物组成为依马美汀B1a（81-100% TRR）和去甲基依马美汀B1a（0-17% TRR），在一些肌肉样本中可见到N-甲酰依马美汀B1a的微量（小于2%）。选作依马美汀残留监管监测的标志残留物是依马美汀B1a。使用高效液相色谱-荧光法在个体皮肤和肌肉样本中定量依马美汀B1a水平，在所有分析的样本中（给药后3小时至30天），均低于85 ppb。

Atlantic salmon (approximately 1.3 kg) maintained in tanks of seawater at 5 +/- 1 degrees C were dosed with 3H-emamectin B1 benzoate in feed at a nominal rate of 50 ug of emamectin benzoate/kg/day for 7 consecutive days. Tissues, blood, and bile were collected from 10 fish each at 3 and 12 hr and at 1, 3, 7, 15, 30, 45, 60, and 90 days post final dose. Feces were collected daily from the tanks beginning just prior to dosing to 90 days post final dose. The total radioactive residues (TRR) of the daily feces samples during dosing were 0.25 ppm maximal, and >97% of the TRR in pooled feces covering the dosing period was emamectin B1a. Feces TRR then rapidly declined to approximately 0.05 ppm by 1 day post final dose. The ranges of mean TRR for tissues over the 90 days post dose period were as follows: kidney, 1.4-3 ppm; liver, 1.0-2.3 ppm; skin, 0.04-0.09 ppm; muscle, 0.02-0.06 ppm; and bone, <0.01 ppm. The residue components of liver, kidney, muscle, and skin samples pooled by post dose interval were emamectin B1a (81-100% TRR) and desmethylemamectin B1a (0-17% TRR) with N-formylemamectin B1a seen in trace amounts (<2%) in some muscle samples. The marker residue selected for regulatory surveillance of emamectin residues was emamectin B1a. The emamectin B1a level was quantified in individual samples of skin and muscle using HPLC-fluorometry and was below 85 ppb in all samples analyzed (3 hr to 30 days post dose).

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

阿维菌素衍生品

埃玛菌素（emamectin，又称甲氨基阿维菌素）是以阿维菌素为母体通过半合成进行结构改造而开发出的一系列活性更高、选择性更强、安全性更优的衍生新品种。最初，阿维菌素主要用作驱寄生虫药剂，尽管它是一种优秀的兽用驱虫剂，但由于其经皮毒性很低但人畜口服毒性较高，做成口服剂时存在一个矛盾：用量太低效果不好，而用量太高则安全性不足。为了改善这一不足，默克公司对其化学结构进行了改造，从中筛选出了两个新的化合物即伊维菌素和埃玛菌素。

作用机理

伊维菌素明显地改善了人畜的急性口服毒性，因此兽用阿维菌素驱虫剂现在通常使用的是伊维菌素成分。埃玛菌素则扩大了阿维菌素的杀虫谱并克服了阿维菌素对鳞翅目害虫效果不佳的问题。埃玛菌素的制剂苯甲酸盐即为甲维盐，因此伊维菌素和甲维盐可视为原来阿维菌素的升级改良产品。伊维菌素毒性较低，主要用于动物（且其结构更稳定，也是全球销量最大的阿维菌素系列之一）。相比之下，甲维盐活性比阿维菌素高很多（胃毒毒性是阿维菌素的2146倍），尤其对鳞翅目、双翅目和蓟马类害虫表现出极高的活性。例如，对于斜纹夜蛾等鳞翅目害虫，阿维菌素效果不佳，但甲维盐却是特效药。

适用作物

埃玛菌素适用于蔬菜、果树、烟草、茶树、花卉及大田作物（如水稻、棉花、玉米、小麦和大豆等）。

防治对象

甲维盐对多种害虫具有其他农药无法比拟的活性，尤其对鳞翅目、双翅目和蓟马类害虫效果超群。具体防治对象包括红带卷叶蛾、烟蚜夜蛾、棉铃虫、烟草天蛾、小菜蛾黏虫、甜菜夜蛾、旱地贪夜蛾、纷纹夜蛾、甘蓝银纹夜蛾、菜粉蝶、菜心螟、甘蓝横条螟、番茄天蛾、马铃薯甲虫、墨西哥瓢虫、红蜘蛛和食心虫等。

合成方法

甲氨基阿维菌素可从一种天然的土壤放射菌——链霉菌的发酵分离得到。

文献信息

• TOPICAL PHARMACEUTICAL COMPOSITION CONTAINING A WATER-SENSITIVE ACTIVE PRINCIPLE
  申请人：Nadau-Fourcade Karine

  公开号：US20120004200A1

  公开（公告）日：2012-01-05

  A topical pharmaceutical composition including, as a pharmaceutical active agent, a water-sensitive compound in a solubilised form in a physiologically acceptable medium is described. A method for preparing such a composition, and uses thereof in dermatology are also described.

  一种局部制药组合物被描述，其中包括一种水敏感化合物的药物活性剂，以生理可接受的介质中的溶解形式存在。还描述了制备这种组合物的方法以及在皮肤科中的用途。
• Synergistic Combination of Glutamate-and Gaba-Gated Chloride Agonist Pesticide and at Least One Vitamin E, Niacin, or Derivatives Thereof
  申请人：Pedersen Morten

  公开号：US20090111759A1

  公开（公告）日：2009-04-30

  Presented are pesticidal compositions comprising at least one pesticide selected among Glutamate- or GABA-gated chloride channel agonist pesticides and at least one synergist which is selected among Vitamin E, Niacin and derivatives thereof. The combinations of these compounds show a synergistic effect allowing a composition to be prepared comprising a lesser amount of pesticide, while still controlling the harmful pests.

  提供的是杀虫组合物，包括至少一种从谷氨酸或GABA门控氯离子通道激动剂杀虫剂中选择的杀虫剂，以及至少一种从维生素E、烟酸及其衍生物中选择的协同剂。这些化合物的组合表现出协同效应，允许制备含较少杀虫剂的组合物，同时仍然控制有害的害虫。
• Synergistic combination of glutamate- and GABA-gated chloride agonist pesticide and at least one of Vitamin E or Niacin
  申请人：Cheminova A/S

  公开号：EP1849363A1

  公开（公告）日：2007-10-31

  Presented are pesticidal compositions comprising at least one compound A selected among Glutamate- or GABA-gated chloride channel agonist pesticides and at least one compound B which is selected among Vitamin E and Niacin. The combinations of these compounds show a synergistic effect in the control of harmful pests.

  所介绍的杀虫组合物包含至少一种选自谷氨酸或 GABA 门控氯离子通道激动剂杀虫剂的化合物 A 和至少一种选自维生素 E 和烟酸的化合物 B。这些化合物的组合在控制有害害虫方面显示出协同效应。
• Pesticidal compositions
  申请人：Cheminova A/S

  公开号：EP2033518A1

  公开（公告）日：2009-03-11

  Presented are pesticidal compositions comprising at least one pesticide selected among Glutamate- or GABA-gated chloride channel agonist pesticides and at least one synergist which is selected among long chain alcohols. The combinations of these compounds show a synergistic effect allowing a composition to be prepared comprising a lesser amount of pesticide, while still controlling the harmful pests.

  所介绍的杀虫组合物包含至少一种从谷氨酸或 GABA 门控氯离子通道激动剂杀虫剂中选出的杀虫剂和至少一种从长链醇中选出的增效剂。这些化合物的组合显示出协同增效作用，从而可以制备出含有较少杀虫剂的组合物，同时仍能控制有害害虫。
• Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren
  申请人：Bayer CropScience AG

  公开号：EP2227951A1

  公开（公告）日：2010-09-15

  Verwendung von Enaminocarbonylverbindungen der Formel (I) worin R1 und A die in der Beschreibung angegebenen Bedeutungen haben, oder von Wirkstoffkombinationen, die aus bekannten Enaminocarbonylverbindungen einerseits und weiteren bekannten insektiziden Wirkstoffen andererseits bestehen, zur Bekämpfung von durch Vektoren (Insekten) übertragenen Virosen.

  使用式 (I) 的烯羰基化合物 其中 R1 和 A 的含义见说明、 或由已知的烯氨羰基化合物和其他已知的杀虫活性成分组成的活性成分组合物，用于抗击由载体（昆虫）传播的病毒。