CN101948413B - Method for preparing flubendiamide - Google Patents
Method for preparing flubendiamide Download PDFInfo
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- CN101948413B CN101948413B CN 201010271402 CN201010271402A CN101948413B CN 101948413 B CN101948413 B CN 101948413B CN 201010271402 CN201010271402 CN 201010271402 CN 201010271402 A CN201010271402 A CN 201010271402A CN 101948413 B CN101948413 B CN 101948413B
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Abstract
The invention provides a method for preparing flubendiamide. The method comprises the following steps of: adding N2-[1,1-dimethyl-2-methylmercaptoacylethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrachloro-1-trifluoromethaneethyl)-1,2-phthalic diamide to a solvent; introducing air in the presence of nitric acid and manganese acetate which are used as catalysts to carry out an oxidizing reaction; and then collecting a target product from a reaction product. In the method, because the air is used for carrying out the oxidizing reaction, the cost is reduced, and the acid is reduced; the raw material conversion can reach higher than 99 percent; and the method has the advantages of reasonable process, simple and safe operation, low cost and convenience for industrial production.
Description
Technical field
The present invention relates to the preparation method of Flubendiamide.
Background technology
Flubendiamide belongs to Novel ortho benzenedicarboxamide insecticides, and nearly all lepidopteran class pest all has good activity, not only adult and larva is had good activity, and speed of action is fast, the lasting period is long.Rice-stem borer and leaf roll snout moth's larva there is special efficacy.Very low to honeybee toxicity, also very low to carp (hydrobiological representative) toxicity.Under general consumption to there being beneficial insect not have activity (almost non-toxic).Mainly contain at present following preparation method:
Document WO 2005063703 discloses with N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the 2-benzenedicarboxamide is raw material obtains Flubendiamide with hydrogen peroxide oxidation method:
Productive rate: 83-87%.The method solvent can not reuse, and spent acid is more.
In sum, above method produces more spent acid.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of Flubendiamide, the defective that exists to overcome prior art.
Method of the present invention is characterized in that, comprises the steps:
With N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the 2-benzenedicarboxamide is in solvent, in the presence of catalyzer nitric acid and manganese acetate, 60-120 ℃ passes into air and carries out oxidizing reaction, and the reaction times is 5～8 hours, then collects target product from reaction product;
Further, from reaction product, collect the method for target product, comprise decompression and solvent recovery and nitric acid, then add first alcohol and water recrystallization, the nitric acid of recovery and solvent reusable edible.
Nitric acid and N2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the weight ratio of 2-benzenedicarboxamide is 0.5～1: 1;
Manganese acetate and N2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the weight ratio of 2-benzenedicarboxamide is 0.01～0.1: 1;
Described solvent is more than one among DMF or the DMAC, in the solvent, and N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the content of 2-benzenedicarboxamide is 0.1-0.3g/ml.
Method of the present invention owing to adopting air to carry out oxidizing reaction, has therefore reduced cost, has reduced spent acid.The inventive method feedstock conversion can reach more than 99%, and technique is reasonable, simple to operate safe, with low cost, just with suitability for industrialized production.
Embodiment
Embodiment 1
With 450 milliliters of DMF, 50 gram weight concentration be 95% nitric acid, 2 the gram manganese acetates and 66.6 the gram (0.1 mole) N2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, in the reaction flask that the adding of 2-benzenedicarboxamide is 1000 milliliters, stirring is warming up to 70 ℃, pass into air and carry out atmospheric oxidation, the reaction times is 8 hours, tracks to feedstock conversion greater than 99% with HPLC.Then reclaim under reduced pressure DMF and nitric acid add first alcohol and water recrystallization.After the drying 60 gram products, productive rate approximately 88%.
Embodiment 2
Be the N2-[1 of 95% nitric acid, 5 gram manganese acetates and 66.6 grams (0.1 mole) with 450 milliliters of DMF, 50 gram weight concentration, 1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, in the reaction flask that the adding of 2-benzenedicarboxamide is 1000 milliliters, stirring is warming up to 105 ℃, pass into air and carry out atmospheric oxidation, the reaction times is 8 hours, tracks to feedstock conversion greater than 99% with HPLC.Then reclaim under reduced pressure DMF and nitric acid add first alcohol and water recrystallization.After the drying 57 gram products, productive rate approximately 84%.
Embodiment 3
With 400 milliliters of DMAC, 100 gram weight concentration be 95% nitric acid, 2 the gram manganese acetates and 66.6 the gram (0.1 mole) N2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-I-N1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, in the reaction flask that the adding of 2-benzenedicarboxamide is 1000 milliliters, stirring is warming up to 90 ℃, pass into air and carry out atmospheric oxidation, the reaction times is 5 hours, tracks to feedstock conversion greater than 99% with HPLC.Then reclaim under reduced pressure DMAC and nitric acid add first alcohol and water recrystallization.After the drying 56 gram products, productive rate approximately 82%.
Claims (7)
1. the preparation method of Flubendiamide is characterized in that, comprises the steps: N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-iodo-N
1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the 2-benzenedicarboxamide in the presence of catalyzer nitric acid and manganese acetate, passes into air and carries out oxidizing reaction in solvent, then collects target product from reaction product.
2. method according to claim 1 is characterized in that, collects the method for target product from reaction product, comprises decompression and solvent recovery and nitric acid, then adds first alcohol and water recrystallization, the nitric acid of recovery and solvent reusable edible.
3. method according to claim 1 is characterized in that, in the presence of catalyzer nitric acid and manganese acetate, 60-120 ℃ passes into air and carry out oxidizing reaction.
4. method according to claim 3 is characterized in that, the reaction times is 5～8 hours.
5. method according to claim 1 is characterized in that, nitric acid and N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-iodo-N
1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the weight ratio of 2-benzenedicarboxamide is 0.5～1: 1;
Manganese acetate and N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-iodo-N
1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the weight ratio of 2-benzenedicarboxamide is 0.01～0.1: 1.
6. method according to claim 1 is characterized in that, described solvent is more than one among DMF or the DMAC.
7. each described method is characterized in that according to claim 1～6, in the solvent, and N
2-[1,1-dimethyl-2-first sulfonyl ethyl]-3-iodo-N
1-[2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl) phenyl]-1, the content of 2-benzenedicarboxamide is 0.1-0.3g/ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010271402 CN101948413B (en) | 2010-08-31 | 2010-08-31 | Method for preparing flubendiamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010271402 CN101948413B (en) | 2010-08-31 | 2010-08-31 | Method for preparing flubendiamide |
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| Publication Number | Publication Date |
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| CN101948413A CN101948413A (en) | 2011-01-19 |
| CN101948413B true CN101948413B (en) | 2013-03-27 |
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| CN 201010271402 Active CN101948413B (en) | 2010-08-31 | 2010-08-31 | Method for preparing flubendiamide |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102320998B (en) * | 2011-07-11 | 2014-08-20 | 华东理工大学 | Phthalic diamide compounds containing 2'-hydroxy hexafluoro isopropyl group and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1255491A (en) * | 1998-11-30 | 2000-06-07 | 日本农药株式会社 | Butyl benzene orthobenzol diacid amide derivative or its salt, garderning pesticide and its application method |
| CN1906158A (en) * | 2003-12-26 | 2007-01-31 | 日本农药株式会社 | Method for producing 2-halogenated benzamides |
-
2010
- 2010-08-31 CN CN 201010271402 patent/CN101948413B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1255491A (en) * | 1998-11-30 | 2000-06-07 | 日本农药株式会社 | Butyl benzene orthobenzol diacid amide derivative or its salt, garderning pesticide and its application method |
| CN1906158A (en) * | 2003-12-26 | 2007-01-31 | 日本农药株式会社 | Method for producing 2-halogenated benzamides |
Non-Patent Citations (1)
| Title |
|---|
| 曹燕蕾，等.新型杀虫剂Flubendiamide及其合成工艺.《现代农药》.2006,第5卷(第3期),39－41. * |
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| CN101948413A (en) | 2011-01-19 |
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