Synthetic method and application of 4-oxo-trans-2-hexenal analogues

A synthesis method and hexenal technology are applied in the field of synthesizing sex pheromone analogs, which can solve the problems of short duration, fast field release, generation of insect resistance, etc., and achieve long duration and strong specificity. , strong anti-stress effect

Active Publication Date: 2022-07-19
INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The research on insect sex pheromones has opened up a new green way to effectively control three kinds of Miridae pests. -2-hexenal has its own disadvantages such as easy condensation, fast release in the field, short duration, long-term use of 4-oxo-trans-2-hexenal may lead to insect resistance, etc.

Method used

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  • Synthetic method and application of 4-oxo-trans-2-hexenal analogues
  • Synthetic method and application of 4-oxo-trans-2-hexenal analogues
  • Synthetic method and application of 4-oxo-trans-2-hexenal analogues

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 The preparation method of 5-methyl-4-oxo-trans-2-hexenal

[0024] The synthetic route of the compound 5-methyl-4-oxo-2-hexenal in the present invention is as follows figure 2 shown.

[0025] In a 100mL flask, dissolve 1g (11.61mmol) of methyl isopropyl ketone in 30mL at a concentration of 0.08mol·L -1 In the sodium hydroxide solution, 0.85g (14.5mmol) of glyoxal solution was gradually added dropwise. The reaction process was monitored by TLC. After the raw materials were no longer reduced, the reaction was complete. The reaction temperature was maintained at 4-5°C and the reaction time was 5h. The crude product was poured into 25 mL of saturated saline solution, washed 3 times, dried over anhydrous magnesium sulfate for 30 min, filtered and evaporated under reduced pressure. The target compound was obtained by silica gel column chromatography (ethyl acetate:petroleum ether=1:50).

[0026] The physical properties, yield, nuclear magnetic resonance data and ...

Embodiment 2

[0028] Example 2 Preparation of 5,5-difluoro-4-oxo-trans-2-hexenal

[0029] The synthetic route of the compound 5,5-difluoro-4-oxo-trans-2-hexenal in the present invention is as follows image 3 shown.

[0030] In a 100 mL three-necked flask, add 2 g (18.18 mmol) of 2,2-difluoropropionic acid and 30 mL of dry methanol solution, replace the air in the three-necked flask with nitrogen, introduce ammonia gas, and conduct the ammoniation reaction for 2 to 4 h under the control of The reaction temperature was room temperature. 1.6 g of 2,2-difluoropropionamide was produced in a yield of 80.8%. 1.6g (14.68mmol) 2,2-difluoropropionamide was dissolved in 25mL toluene solution, in P 2 O 5 Dehydration in the presence of 2,2-difluoropropionitrile. The resulting 2,2-difluoropropionitrile was reacted with methylmagnesium iodide and hydrolyzed to synthesize 3,3-difluoro-2-butanone with a yield of 73.6%.

[0031] Dissolve 1g (9.25mmol) of 3,3-difluoro-2-butanone in 30mL at a concentrat...

Embodiment 3

[0035] Embodiment 3 The test of attracting chlorophyll bugs in the field

[0036] The lure cores prepared with the Lygus bug sex attractant composition are placed in boat-type traps, and the traps are placed on the plots where more Lygus bugs are likely to be harmed. In order to ensure the release effect, 100–2000 μg of the chlorophyll sex attractant composition was placed in each 1 mL of the rubber lure. In order to further illustrate the feasibility of this embodiment, 10 specific formulations are given in Table 1.

[0037] Table 1

[0038]

[0039] Select the plots where there may be more chlorotic bug hazards, set traps at a height of about 120cm from the ground for each formula, and the distance between the traps is 10m. Each treatment set up 5 replicates. After placement, the number of trapped green bugs was investigated every other day, and the trapping locations were randomly changed for 20 days. The survey results are shown in Table 2:

[0040] Table 2

[004...

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Abstract

The invention discloses a synthesis method and application of 4-oxo-trans-2-hexenal analogs belonging to the technical field of biological control. The analogs include 5-methyl-4-oxo-trans-2-hexenal, 5,5-difluoro-4-oxo-trans-2-hexenal, 4-oxo-trans-2-hexenal Hexenoic acid, 4-oxo-trans-2-hexenol, 4-hydroxy-trans-2-hexenal. One or more of the above-mentioned 5 kinds of compounds completely replace the 4-oxo-trans-2-hexenal in the sex pheromone components of Lygus chinensis, Lygus gracilis, and Lygus mesophilum. The 5-methyl-4-oxo-trans-2-hexenal and 5,5-difluoro-4-oxo-trans-2-hexenal synthesis methods of the present invention are all discovered for the first time, and the application compositions thereof can be Significantly slows down the release rate of lures, prolongs trapping time, saves costs, and can avoid the instability problem of 4-oxo-trans-2-hexenal in the field, and is more effective in trapping and killing Lygus chinensis, Lygus praecox, and black bug Bugs and other males.

Description

technical field [0001] The invention belongs to the technical fields of organic synthesis and biological control, and in particular relates to a method for synthesizing sex pheromone analogs for preventing and controlling Lygus chinensis, Lygus melanogaster and Lygus gracilis and application thereof. Background technique [0002] Apolygus lucorμm, Lygus pratensis Linnaeus, Adelphocoris suturalis Jakovlev, all belonging to Hemiptera, Lygus family, are important pests in my country's cotton areas, causing serious damage to my country's cotton industry. huge loss. [0003] The research on insect sex pheromone has opened up a new green way for the efficient control of three Lygus pests. -2-Hexenal has the disadvantages of easy condensation, fast release in the field, short duration, and long-term use of 4-oxo-trans-2-hexenal may lead to the generation of insect resistance. Therefore, the preparation of sex pheromone analogs with slow release, long lasting effect and strong attr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/258C07C45/74C07C233/05C07C231/02C07C255/10C07C253/20C07C49/167C07C45/00A01N35/02A01N37/06A01N25/18A01P19/00
CPCC07C49/258C07C45/74C07C45/004C07C231/02C07C253/20A01N35/02A01N37/06A01N25/18C07B2200/09C07C233/05C07C255/10C07C49/167
Inventor 宁君梅向东王留洋马好运吴孔明
Owner INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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