Preparation method of juvenile hormone analogue

A juvenile hormone and analogue technology, applied in the field of preparation of juvenile hormone analogues, can solve the problems of low material yield and content, high sewage treatment cost, cumbersome operation steps, etc., and achieve shortened reaction cycle and easy operation , the effect of simple processing steps

Active Publication Date: 2015-01-14
常州胜杰生命科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The removal of residual organic titanate in the system after the reaction is also cumbersome. The reaction solution needs to be diluted with a solvent first, washed with sulfuric acid, and then washed with glycolic acid and potassium carbonate solution separately to ensure that the titanate is removed completely and then concentrated to remove the washing step. Additional solvents are added to obtain the final product, the operation steps are cumbersome, the yield is lost, the amount of organic sewage produced by industrialization is large, the process is not environmentally friendly, and the cost of sewage treatment is high
[0004] CliveA.Henrick et al. Stereoselective synthesis of alkyl(2E,4E)-and(2Z,4E)-3,7,11-trimethyl-2,4-dodecadienoates in the journal of organic chemistry, Volume 40, Issue 1, 1975. Insect growth regulators with juvenile hormone activity used (2E,4E)11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid to react with SOCl2 to obtain acid chloride, and then reacted with iso Propanol reacts to obtain the target product, but the preparation process is complicated, and the yield and content of the obtained substance are not high

Method used

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  • Preparation method of juvenile hormone analogue
  • Preparation method of juvenile hormone analogue

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Prepare a dry and clean 1L four-necked reaction flask, and add (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid to the flask sequentially 26.9g (0.1mol), catalyst 4-dimethylaminopyridine 1.22g (0.01mol) and toluene 100mL, stirred at 15-30°C; add diisopropyl pyrocarbonate toluene solution dropwise into the flask (diisopropyl pyrocarbonate ester 26.6g, 0.14mol; toluene 133mL); after the dropwise addition, stir and react at 15-30°C for 2h; add 23.3mL water into the flask, stir for 5min, let stand for phase separation, and separate the upper toluene layer; The organic phase was concentrated under pressure, and 27.9 g of S-methoprene product was obtained by distillation, with a weight yield of 103.7% and a molar yield of 90%. Product content: 97.3%, isomer: 0.8%.

Embodiment 2

[0061] Prepare a dry and clean 1L four-necked reaction flask, and add (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid to the flask sequentially 26.9g (0.1mol), catalyst pyridine 9.1g (0.1mol) and dichloromethane 26.9mL, stir at 0-25°C; add diisopropyl pyrocarbonate dichloromethane solution (diisopropyl pyrocarbonate) dropwise into the flask Ester 38.0g, 0.2mol; dichloromethane 38mL); After the dropwise addition, add 64.9mL water in the flask, after stirring for 5min, let stand to separate the phases, separate the lower dichloromethane layer; concentrate the organic phase under reduced pressure, S-methoprene product was obtained by distillation 27.8g, with a weight yield of 103.3% and a molar yield of 90%. Product content: 97.4%, isomer: 0.8%.

Embodiment 3

[0063] Prepare a dry and clean 1L four-necked reaction flask, and add (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid to the flask sequentially 26.9g (0.1mol), diisopropyl pyrocarbonate 26.6g (0.14mol) and toluene 269mL, stirred at 15-25°C; add the toluene solution of the catalyst 4-dimethylaminopyridine (4-dimethylaminopyridine) dropwise into the flask Aminopyridine 1.22g, 0.01mol; toluene 6.1mL); after the dropwise addition, stir and react at 15-30°C for 1h. Add 138mL of water into the flask, stir for 5min, let stand to separate the phases, and separate the upper toluene layer; concentrate the organic phase under reduced pressure, and distill to obtain 27.9g of S-methoprene product, with a weight yield of 103.7% and a molar yield of 90 %. Product content: 97.3%, isomer: 0.8%.

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Abstract

The invention relates to the field of insecticides, and particularly relates to a preparation method of a juvenile hormone analogue (which comprises S-methoprene and S-hydroprene). The preparation method of the juvenile hormone analogues comprises the following steps of: A. adding (2E, 4E)-11-R-3,7,11-trimethyl-2,4-dodecadienoic acid (R is hydrogen or methoxyl) serving as raw material, an organic alkali catalyst and an organic solvent to a reaction vessel, and starting stirring; B. dropwise adding an organic solvent (the same as the organic solvent in the step A) solution of pyrocarbonate; C. after the addition is completed, reacting at 0-30 DEG C for 0-3 hours; D. adding water to stop reaction, and splitting phases of reaction liquid to obtain an organic phase; E. carrying out reduced pressure concentration and distillation to obtain a product, wherein the steps can also be carried out under the condition that the addition sequences of the pyrocarbonate and an organic strongly-alkaline catalyst are exchanged. The preparation method disclosed by the invention has the advantages of mild reaction condition, high product purity, high yield, environment-friendly and safe route and good industrial prospect.

Description

technical field [0001] The invention relates to the field of insecticides, in particular to a preparation method of juvenile hormone analogs. Background technique [0002] The juvenile hormone analogue S-methoprene (chemical name (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester) and S-methoprene (chemical name (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoic acid ethyl ester), belongs to insect growth regulator, is a new type, green, Environmental protection, non-toxic, no residue of biochemical pesticides. Different from traditional products that rely on toxicity to kill insects, juvenile hormone regulates the growth hormone in insects so that they cannot emerge into adults and achieve the effect of killing insects. The products can be applied to the elimination and control of vector organisms (mosquitoes, flies, midges and other organisms), tobacco beetle, stored grain pests, fire ants, fleas, mushroom mosquitoes and other pests. Its synthesis method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/11C07C69/734C07C69/587
CPCC07B2200/07C07C67/11C07C67/54C07C69/734C07C69/587
Inventor 苏衡王加高李海燕申传伟
Owner 常州胜杰生命科技股份有限公司
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