Emamectin B1b
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| Category | Others |
| Catalog number | BBF-04243 |
| CAS | 121424-52-0 |
| Molecular Weight | 872.09 |
| Molecular Formula | C48H73NO13 |
| Purity | >99% by HPLC |
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Description
It is a semi-synthetic 4-epimethylamino analogue of avermectin B1b. It is prepared by oxidation of the 4-hydroxy moiety and reductive amination. It has strong insecticidal efficacy.
Specification
| Synonyms | Avermectin A1a, 5-O-demethyl-25-de(1-methylpropyl)-4''-deoxy-4''-(methylamino)-25-(1-methylethyl)-, (4''R)- |
| Storage | Store at -20°C |
| IUPAC Name | (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)-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-4-methoxy-5-[(2S,4S,5R,6S)-4-methoxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethyl-2-propan-2-ylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one |
| Canonical SMILES | CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)NC)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O |
| InChI | InChI=1S/C48H73NO13/c1-25(2)42-28(5)17-18-47(62-42)23-34-20-33(61-47)16-15-27(4)43(26(3)13-12-14-32-24-55-45-41(50)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-11)44(31(8)57-39)60-38-21-36(53-10)40(49-9)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,16,20-24H2,1-11H3/b13-12+,27-15+,32-14+/t26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41+,42+,43-,44-,45+,47+,48+/m0/s1 |
| InChI Key | DXIOOXFZLKCVHK-VAUHGISYSA-N |
| Source | Active ingredient in some commercial ant bait traps. |
Properties
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 928.4±65.0°C (Predicted) |
| Density | 1.22±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Toxicity
| Carcinogenicity | Not listed by IARC. |
| Mechanism Of Toxicity | It has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. |
Reference Reading
1. Ameliorative effect of vitamin C against hepatotoxicity induced by emamectin benzoate in rats
C Richeval, N Zerrouki-Daoudi, N Lebaili, N Djennas, D Allorge, M Baha, H Khaldoun Oularbi Hum Exp Toxicol . 2017 Jul;36(7):709-717. doi: 10.1177/0960327116661022.
In the present study, we aimed to assess the potential protective effect of ascorbic acid (AA) against emamectin benzoate (EMB)-induced hepatotoxicity. For this purpose, biochemical, histopathological and analytical investigations were performed. Male Wistar rats were distributed into three groups, that is, a control group, an EMB group given 10 mg EMB/kg body weight (BW) by gavage and an EMB + AA group given 10 mg EMB/kg BW and vitamin C intraperitoneally (200 mg/kg). The duration of the treatment was 28 days and the duration of the study was 42 days. There was a statistically significant increase of all hepatic biomarkers, that is, aspartate aminotransferase, alanine aminotransferase and gamma-glutamyltransferase activities, and glycemia, in EMB-treated group when compared with the control group. Light microscopic observations revealed variable signs of hepatotoxicity in the EMB group, which were represented by alteration of normal hepatic architecture, inflammatory cell infiltration, hepatocellular steatosis and foci of necrosis at 28 and 42 days post-treatment. However, co-treatment with vitamin C reduced EMB-related liver toxicity and diminished the abnormal biochemical and architectural damage. Emamectin B1a and B1b residues were detectable in all plasma samples of treated rats at 14, 21 and 28 days of treatment. The drug liver tissue concentration was significantly lower in EMB + AA group compared with EMB group at 28 and 42 days. In conclusion, the findings of the present study clearly indicate a significant protective action of vitamin C against EMB hepatotoxicity.
2. Toxicities of emamectin benzoate homologues and photodegradates to Lepidoptera
Richard K Jansson, Van R Starner, W Ross Halliday, Joseph A Argentine J Econ Entomol . 2002 Dec;95(6):1185-9. doi: 10.1603/0022-0493-95.6.1185.
The toxicity of a number of emamectin benzoate homologues and photodegradates to five species of Lepidoptera was investigated using diet and foliar bioassays. The emamectin benzoate homologues B1a and B1b were equally toxic in the diet and foliar assays to Spodoptera exigua (Hübner), Heliothis virescens (F.), Tricoplusia ni (Hübner), and Spodoptera frugiperda (J. E. Smith), within each of these species. Plutella xylostella (L.) was the most sensitive species to emamectin benzoate. The AB1a photodegradate of emamectin benzoate was as toxic as the parent compound in the diet assay. However, in the foliage assay AB1a was 4.4-fold less toxic to S. exigua than the parent compound. The MFB1a photodegradate of emamectin benzoate was as toxic as the parent compound to P. xylostella, and 3.1 to 6.2 times as toxic as the parent compound to the other species in the diet assay. The order of toxicity of the photodegradates were AB1a > MFB1a > FAB1a > 8,9-Z-MAB1a > PAB1a.
3. Simultaneous determination of residues of emamectin and its metabolites, and milbemectin, ivermectin, and abamectin in crops by liquid chromatography with fluorescence detection
K Yoshii, Y Tsumura, S Ishimitsu, Y Tonogai, A Kaihara J AOAC Int . 2001 May-Jun;84(3):910-7.
A liquid chromatographic (LC) method was developed for the determination of emamectin and its metabolites (8,9-Z-isomer, N-demethylated, N-formylated, and N-methylformylated emamectin) in various crops. The analytes were extracted with acetone, cleaned up on cartridge columns (C18 and NH2), derivatized with trifluoroacetic anhydride and 1-methylimidazole, and determined by LC with fluorescence detection. Because radish inhibited the formation of the fluorescent derivatives, an additional Bond Elut PRS cartridge was used in the cleanup of Japanese radish samples. During sample preparation, N-formylated emamectin partially degraded to emamectin B1b and emamectin B1a, and the 8,9-Z-isomer partially degraded to N-demethylated emamectin. Therefore, emamectin and its metabolites were determined as total emamectin, i.e., their sum was estimated as emamectin benzoate. Their recoveries from most crops were approximately 80-110% with the developed method. The detection limits for the analytes in vegetables were 0.1-0.3 parts per trillion (ppt). The results for these compounds were confirmed by LC/mass spectrometry (LC/MS; electrospray ionization mode). Because the fluorescent derivative of emamectin was undetectable by LC/MS, the results for the analyte were confirmed by using a sample solution without derivatization. Limits of detection by LC/MS were similar to the fluorescence detection limits, 0.1-0.3 ppt in vegetables. In addition to the emamectins, milbemectin, ivermectin, and abamectin were also determined by the developed method.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C48H73NO13
Molecular Weight (Monoisotopic Mass): 871.5082 Da
Molecular Weight (Avergae Mass): 872.0921 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C48H73NO13
Molecular Weight (Monoisotopic Mass): 871.5082 Da
Molecular Weight (Avergae Mass): 872.0921 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
