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A kind of preparation method of S body indoxacarb

A technology of indoxacarb and metal zirconium, which is applied in the field of preparation of S-indoxacarb, can solve the problems of unrecyclable catalyst, high production cost, low catalyst efficiency, etc., and achieves the benefits of industrialization, improved reaction speed, and enhanced selection. sexual effect

Active Publication Date: 2019-11-19
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] First, cinchona base catalysts such as cinchonin are used, but the efficiency of this type of catalyst is low, and the S body content of the synthesized indoxacarb original drug is about 70%;
[0005] Second, metal complex catalysts are used. In 2007, DuPont Company of the United States reported a metal zirconium catalyst, but this type of catalyst cannot be recycled, and the production cost is relatively high, and the S body content of the obtained indoxacarb original drug is about 90%;

Method used

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  • A kind of preparation method of S body indoxacarb
  • A kind of preparation method of S body indoxacarb
  • A kind of preparation method of S body indoxacarb

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1 A chiral catalyst containing metal zirconium and a method for preparing S body indoxacarb using the catalyst, the preparation method is as follows:

[0038] (1) Add 22.65g (0.1mol) 3-tert-butyl-5-chloromethyl salicylaldehyde to 100mL clean anhydrous reaction flask, then add 50mL methanol, then weigh 11.4g (0.1mol) cyclohexanedi Amine, slowly added dropwise at 20-25°C.

[0039] (2) After the dropwise addition, the temperature was raised to 65-70°C for reflux reaction. After the reaction, the temperature was lowered to 10°C, and the ligand polymer was obtained by filtration, dried and weighed.

[0040] (3) 2000 mL of a clean anhydrous reaction bottle was put into the ligand polymer in step (2), then 50 mL of toluene and 3.78 g (0.1 mol) of sodium borohydride were added, and the temperature was raised to reflux for reaction.

[0041] (4) Add 24.35 g (0.05 mol) of zirconium acetylacetonate to the above reaction system, fully soak and heat up to 80° C., and kee...

Embodiment 2

[0045] Embodiment 2 A chiral catalyst containing metal zirconium and a method for preparing S body indoxacarb using the catalyst, the preparation method is as follows:

[0046] (1) Add 22.65g (0.1mol) 3-tert-butyl-5-chloromethyl salicylaldehyde to 100mL clean anhydrous reaction flask, then add 50mL methanol, then weigh 17.1g (0.15mol) cyclohexanedi Amine, slowly added dropwise at 20-25°C.

[0047] (2) After the dropwise addition, the temperature was raised to 65-70°C for reflux reaction. After the reaction, the temperature was lowered to 10°C, and the ligand polymer was obtained by filtration, dried and weighed.

[0048] (3) 2000 mL of a clean anhydrous reaction bottle was put into the ligand polymer in step (2), then 50 mL of toluene and 5.4 g (0.1 mol) of potassium borohydride were added, and the temperature was raised to reflux for reaction.

[0049] (4) Add 24.35 g (0.05 mol) zirconium acetylacetonate to the above reaction system, fully swell and heat up to 80° C., heat p...

Embodiment 3

[0053] Embodiment 3. Recycling of metal polymer catalyst

[0054] The catalyst recovered by filtration in Example 2 was added to toluene, and then 113g of tert-butyl hydroperoxide and 224g of 5-chloro-2-methoxycarbonyl-1-indanone ester and 1200mL of toluene were added to carry out the asymmetric synthesis reaction, The temperature was raised to 110° C. for reflux reaction for 4 hours. After the reaction is completed, the metal polymer catalyst is recovered by filtration, and the obtained filtrate can be distilled under reduced pressure to obtain the key intermediate 5-chloro-2-methoxycarbonyl-2-hydroxyl-1-indanone; at the same time, the recovered catalyst is put into 50mL A suspension is formed in toluene solvent to continue the asymmetric synthesis reaction; the prepared intermediate is prepared according to the conventional prior art to obtain the S body indoxacarb.

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Abstract

The invention relates to the field of chemical synthesis, and specifically discloses a brand-new catalyst and a method for preparing S-body indoxacarb using the catalyst. The catalyst contains 3-tert-butyl-5-chloromethyl salicylaldehyde and ring Hexamethylenediamine is prepared from hexamethylenediamine, and the catalyst is used to replace the original cinchonine catalysts such as cinchonine, which is applied to the production of tert-butyl hydroperoxide and 5-chloro-2-methoxycarbonyl-1-indanone ester In the asymmetric synthesis reaction, the selectivity in the asymmetric synthesis process is greatly improved, the S body content is increased from 75% to more than 98%, and the recycling of high-efficiency chiral catalysts is realized, which greatly reduces the production cost. The synthesis process is simple, beneficial to industrialization, and lays a good foundation for the production of high-quality indoxacarb.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and specifically discloses a preparation method of S-body indoxacarb. Background technique [0002] Indoxacarb is a new type of oxadiazine insecticide with high efficiency and low toxicity developed by DuPont Company of the United States. It has dual effects of contact killing and stomach poisoning, and can effectively solve resistant pests. It has no cross-resistance with other insecticides such as pyrethroids, organophosphorus, and carbamates, and can well solve the problems of rice leaf rollers, rice stem borers and resistant diamondback moths that are difficult to control in the market. In addition, indoxacarb has a very wide insecticidal spectrum, and one drug can prevent multiple diseases. While preventing and controlling noctuid pests, it also has a good inhibitory effect on mirid bugs, so it is a very good comprehensive management tool. , can well solve the current problems of residues ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07D273/04C07B53/00C08G12/40C08G12/06
CPCC08G12/06C07D273/04C07B53/00C07C67/31C07C2602/08B01J31/1691B01J31/2243B01J2531/0216B01J2531/48B01J2531/0252C07C69/757B01J31/2217B01J31/4015C07B2200/07
Inventor 薄蕾芳成道泉刘建成冯培良刘花敏王中洋
Owner JINGBO AGROCHEM TECH CO LTD