Spinetoram J
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| Category | Agricultural |
| Catalog number | BBF-04246 |
| CAS | 187166-40-1 |
| Molecular Weight | 748.00 |
| Molecular Formula | C42H69NO10 |
| Purity | >95% by HPLC |
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Description
It is the major component in the second generation spinosyn family of bio-insecticides marketed as spinetoram. It is a semi-synthetic compound prepared by selective ethylation and hydrogenation of spinosyn J, and it is also an insecticide.
Specification
| Synonyms | 3-Ethoxy-5,6-dihydro-spinosyn J; XDE-175-J; [2R-(2R*,3aR*,5aR*,5bS*,9S*,13S*,14R*,16aS*,16bR*)]-2-[(6-Deoxy-3-O-ethyl-2,4-di-O-methyl-α-L-mannopyranosyl)oxy]-13-[[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-9-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,16a,16b-hexadecahydro-14-methyl-1H-as-Indaceno[3,2-d]oxacyclododecin-7,15-dione; (2R,3aR,5aR,5bS,9S,13S,14R,16aS,16bR)-2-[(6-Deoxy-3-O-ethyl-2,4-di-O-methyl-α-L-mannopyranosyl)oxy]-13-[[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-9-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,16a,16b-hexadecahydro-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,5R,7R,9R,10S,14R,15S,19S)-15-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-7-[(2R,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-19-ethyl-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-11-ene-13,21-dione |
| Canonical SMILES | CCC1CCCC(C(C(=O)C2=CC3C(C2CC(=O)O1)CCC4C3CC(C4)OC5C(C(C(C(O5)C)OC)OCC)OC)C)OC6CCC(C(O6)C)N(C)C |
| InChI | InChI=1S/C42H69NO10/c1-10-27-13-12-14-35(53-37-18-17-34(43(6)7)24(4)49-37)23(3)38(45)33-21-31-29(32(33)22-36(44)51-27)16-15-26-19-28(20-30(26)31)52-42-41(47-9)40(48-11-2)39(46-8)25(5)50-42/h21,23-32,34-35,37,39-42H,10-20,22H2,1-9H3/t23-,24-,25+,26-,27+,28-,29-,30-,31-,32+,34+,35+,37+,39+,40-,41-,42+/m1/s1 |
| InChI Key | GOENIMGKWNZVDA-RWGFPKGXSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 803.5±65.0°C (Predicted) |
| Melting Point | >75°C (dec.) |
| Density | 1.15±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Chloroform, Methanol |
Reference Reading
1. Degradation kinetics of the insecticide spinetoram in a rice field ecosystem
Yong Zhu, Ting Yang, Yin-Liang Wu, Li Zhao, Yan Zhang, Jian Zhao, Guo Chen Chemosphere . 2015 Jan;119:1185-1191. doi: 10.1016/j.chemosphere.2014.10.026.
The fate of spinetoram was studied in a rice field ecosystem, and an efficient method for the determination of spinetoram (XDE-175-J and XDE-175-L) in soil, rice straw, paddy water, husk and brown rice was developed. Spinetoram residues were extracted from samples with a salting out extraction procedure. The extracts were diluted with 0.10% formic acid in water and analysed with liquid chromatography tandem mass spectrometry (LC-MS/MS) on a Waters Acquity BEH C18 column. The calibration curve was linear in the range 0.125-100 μg L(-1) and r>0.999. The average recovery was 82.9-89.0% from soil, 78.5-92.1% from rice straw, 93.6-100.3% from paddy water, 79.1-87.9% from brown rice and 72.7-82.9% from husk. The relative standard deviation (RSD) was less than 10%. These results are all within the accepted range for pesticide residue determination. The field test results showed that spinetoram degradation in paddy water, soil and rice straw coincided with C=0.0132e(-1.9685t), C=0.0308e(-0.1018t) and C=0.8530e(-0.6223t), respectively. The half-lives of spinetoram in paddy water, soil and rice straw were 0.35, 6.8 and 1.1 d, respectively. The final residue level was lower than the maximum residue limit (MRL) of 0.05 mg kg(-1) for spinetoram in rice with a harvest interval of 7d. A dosage of 450 mL ha(-1) was recommended, which can be considered safe for human beings and animals. The results of this study will contribute to establishing the scientific basis of the dosage of spinetoram for agricultural fields.
2. A novel semi-synthesis of spinetoram-J based on the selective hydrolysis of 5,6-dihydro spinosyn A
Lamusi A, Jiarong Li, Kai Zhang Nat Prod Res . 2019 Oct;33(19):2801-2808. doi: 10.1080/14786419.2018.1503265.
Spinetoram is a novel kind of fermentation-derived insecticide with a broad range of action against lots of insect pests. Due to the broad pest spectrum, high insecticidal activity, low environmental impact, and low toxicity to non-target species, spinetoram has been widely applied in pest control and stored-grain protection. Spinetoram is a mixture of spinetoram-J (XDE-175-J, major component) and spinetoram-L (XDE-175-L). In this study, a novel selective hydrolysis of C9-glycosidic bond of 5,6-dihydro spinosyn A was developed. And a 3-step semi-synthesis of spinetoram-J based on the selective hydrolysis was designed and discussed. All compounds in the synthesis were characterized by 1H NMR, 13C NMR and mass spectrum. In addition, the improved semi-synthesis also provides an efficient way to synthesize the rhamnose replacement analogues of spinetoram-J which may be promising in the pest control and fungus control.
3. A semisynthesis of 3'- O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone
Anjun Liu, Hongxin Chai, Shenglan Liu, Jiarong Li, Kai Zhang, Lamusi A Beilstein J Org Chem . 2017 Dec 6;13:2603-2609. doi: 10.3762/bjoc.13.257.
Spinetoram, a mixture of 3'-O-ethyl-5,6-dihydrospinosyn J (XDE-175-J, major component) and 3'-O-ethylspinosyn L (XDE-175-L, minor component), is a novel kind of green and efficient insecticide with a broad range of action against various insects. Nowadays, spinetoram is widely used in agriculture and food storage. This work reports a 7-step semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J from spinosyn A aglycone. The C9-OH and C17-OH of the aglycone are successively connected to 3-O-ethyl-2,4-di-O-methylrhamnose and D-forosamine after selective protection and deprotection steps. Then, with 10% Pd/C as catalyst, the 5,6-double bond of the macrolide was selectively reduced to afford 3'-O-ethyl-5,6-dihydrospinosyn J. In addition, the 3-O-ethyl-2,4-di-O-methylrhamnose is synthesized from rhamnose which is available commercially, while the D-forosamine and aglycone are obtained via the hydrolysis of spinosyn A. High yields were obtained in each step, and all intermediates in the synthesis were characterized by1H NMR,13C NMR and MS techniques. This study can be helpful for developing an efficient chemical synthesis of spinetoram, and it also offers opportunities to synthesize spinosyn analogues and rhamnose derivatives.
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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 ╳
