TW200716510A - A process for the large scale manufacture of indoxacarb and associated 1, 3, 4 oxadiazines - Google Patents
A process for the large scale manufacture of indoxacarb and associated 1, 3, 4 oxadiazinesInfo
- Publication number
- TW200716510A TW200716510A TW095115558A TW95115558A TW200716510A TW 200716510 A TW200716510 A TW 200716510A TW 095115558 A TW095115558 A TW 095115558A TW 95115558 A TW95115558 A TW 95115558A TW 200716510 A TW200716510 A TW 200716510A
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- oxadiazines
- indoxacarb
- isomer
- large scale
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 239000005907 Indoxacarb Substances 0.000 title abstract 3
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 title abstract 3
- 150000005068 1,3,4-oxadiazines Chemical class 0.000 title abstract 2
- 238000011031 large-scale manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000006835 carbomethoxylation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 150000005063 oxadiazines Chemical class 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 230000000717 retained effect Effects 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
This invention relates to an improved method for the N-Carbomethoxylation of the 1,3,4 oxadiazines of formula (II), and particularly Indoxacarb, using methyl chloro formate in the presence of sodium hydride resulting in compounds of formula (I) in which the ratio of the active S-isomer to the inactive R-isomer in the precursor can be retained. Ratios greater than or equal to 75% S-isomer, preferably greater than or equal to 99%, are achievable in the large scale manufacturing of the oxadiazines of formula (I) in the process. Wherein R1=F, Cl or C1-C3 fluroalkoxy, R2=C1-C3 linear or branched alkyl, or unsubstituted or hetero substituted aryl, R3=C1-C3 linear or branched alkyl, and R4=Trifluromethoxy, trifluromethyl, F, Cl or Br. The invention particularly relates to a process for the conversion of the compound of formula (II) to the compound of formula (I) wherein R1=C1, R2-CH3, R3-CH3 and R4=OCF3, i.e. a process for the production of Indoxacarb.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN530MU2005 IN241255B (en) | 2005-05-02 | 2005-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200716510A true TW200716510A (en) | 2007-05-01 |
| TWI405746B TWI405746B (en) | 2013-08-21 |
Family
ID=38134377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095115558A TWI405746B (en) | 2005-05-02 | 2006-05-02 | A process for the large scale manufacture of indoxacarb and associated 1, 3, 4 oxadiazines |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR053864A1 (en) |
| IN (1) | IN241255B (en) |
| MY (1) | MY141190A (en) |
| TW (1) | TWI405746B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111164A (en) * | 2013-10-11 | 2015-12-02 | 浙江大学 | Crystal form of refined indoxacarb |
| CN110662739A (en) * | 2017-03-29 | 2020-01-07 | 阿达玛马克西姆有限公司 | A new catalytic system for large-scale production of indoxacarb |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262285B (en) * | 2014-07-24 | 2016-08-17 | 浙江大学 | The synthetic method of agricultural insecticide indoxacarb intermediate |
| CN104193696A (en) * | 2014-08-26 | 2014-12-10 | 常州大学 | Preparation method for novel insecticide indoxacarb |
| WO2021005545A1 (en) * | 2019-07-10 | 2021-01-14 | Gharda Chemicals Limited | A process for obtaining indoxacarb crystals with specific purity and enantiomeric ratio |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5462938A (en) * | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
| JP3882195B2 (en) * | 1994-04-20 | 2007-02-14 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Manufacture of joint polycidal oxadiazine |
-
2005
- 2005-05-02 IN IN530MU2005 patent/IN241255B/en unknown
-
2006
- 2006-05-02 AR ARP060101774A patent/AR053864A1/en active IP Right Grant
- 2006-05-02 MY MYPI20062010A patent/MY141190A/en unknown
- 2006-05-02 TW TW095115558A patent/TWI405746B/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111164A (en) * | 2013-10-11 | 2015-12-02 | 浙江大学 | Crystal form of refined indoxacarb |
| CN110662739A (en) * | 2017-03-29 | 2020-01-07 | 阿达玛马克西姆有限公司 | A new catalytic system for large-scale production of indoxacarb |
| CN110662739B (en) * | 2017-03-29 | 2023-10-27 | 安道麦马克西姆有限公司 | Catalytic system for large-scale preparation of indoxacarb |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2005MU00530A (en) | 2005-11-14 |
| AR053864A1 (en) | 2007-05-23 |
| MY141190A (en) | 2010-03-31 |
| IN241255B (en) | 2010-06-25 |
| TWI405746B (en) | 2013-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |