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Synthesis method and application of 4-oxo-trans-2-hexenal analogue

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

Active Publication Date: 2020-12-18
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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  • Synthesis method and application of 4-oxo-trans-2-hexenal analogue
  • Synthesis method and application of 4-oxo-trans-2-hexenal analogue
  • Synthesis method and application of 4-oxo-trans-2-hexenal analogue

Examples

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 compound 5-methyl-4-oxo trans-2-hexenal in the present invention is as follows figure 2 shown.

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

[0026] The physical properties, yield, NMR data and mass spectrometry data of 5-methy...

Embodiment 2

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

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

[0030] In a 100mL three-necked flask, add 2g (18.18mmol) of 2,2-difluoropropionic acid and 30mL of dry methanol solution, replace the air in the three-necked flask with nitrogen, pass in ammonia gas, and carry out the ammoniation reaction for 2 to 4 hours. The reaction temperature is room temperature. 1.6 g of 2,2-difluoropropanamide was produced, with a yield of 80.8%. 1.6g (14.68mmol) 2,2-difluoropropionamide was dissolved in 25mL toluene solution, in P 2 o 5 In the presence of dehydration into 2,2-difluoropropionitrile. 3,3-difluoro-2-butanone can be synthesized by reacting the generated 2,2-difluoropropionitrile with methylmagnesium iodide followed by hydrolysis, with a yield of 73.6%.

[0031] The concentration of 1g (9.25mmol) 3,3-difluoro-2-butanone dissolved in 30mL ...

Embodiment 3

[0035] Embodiment 3 field lures the green Lygus test

[0036] The lure cores prepared with the lucid lygus sex attractant composition are placed in boat-type traps, and the traps are placed in plots that may cause more harm to livid bugs. In order to ensure the release effect, 100-2000 μg of the lucid bug sex attractant composition is placed in every 1 mL of the rubber lure core. In order to further illustrate the feasibility of the present embodiment, 10 specific formulas are provided in Table 1.

[0037] Table 1

[0038]

[0039] Select the plots that may cause more harm of Lygus lygus, each formula sets traps about 120cm above the ground, and the distance between traps is 10m, randomly place the traps containing the above-mentioned Lygus sex pheromone composition, every Five replicates were set up for each treatment. The number of trapped Lygus spp. was surveyed every other day after placement, and the trapping location was changed randomly, and the survey continued f...

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Abstract

The invention discloses a synthesis method and application of a 4-oxo-trans-2-hexenal analogue, and belongs to the technical field of biological prevention and control. The analogues comprise 5-methyl-4-oxo-trans-2-hexenal, 5, 5-difluoro-4-oxo-trans-2-hexenal, 4-oxo-trans-2-hexenoic acid, 4-oxo-trans-2-hexenol and 4-hydroxy-trans-2-hexenal. One or more of the five compounds completely replace 4-oxo-trans-2-hexenal in sex pheromone components of apolygus lucorum, lygus pratensis and apolygus lucorum. The synthesis methods of the 5-methyl-4-oxo-trans-2-hexenal and the 5, 5-difluoro-4-oxo-trans-2-hexenal are found for the first time, the application composition can significantly reduce the release rate of the lure, prolong the trapping time and save the cost, the problem that the 4-oxo-trans-2-hexenal is unstable in the field can be avoided, and the application range of the 5-methyl-4-oxo-trans-2-hexenal is widened. Male insects such as apolygus lucorum, herbage miridae and apolygus lucorum can be trapped and killed more effectively.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and biological control, and specifically relates to a synthesis method and an application thereof of sex pheromone analogues used for preventing and treating Lygus spp. Background technique [0002] Apolygus lucorμm, Lygus pratensis Linnaeus, and Adelphocoris suturalis Jakovlev, all of which belong to the order Hemiptera and the family Miridae, are important pests in my country's cotton regions, causing serious damage to my country's cotton industry. huge loss. [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 of effect, and long-term use of 4-oxo-trans-2-hexenal may lead to insect resistance. Therefore, the preparation of sex pheromone analogues with slow release, long-lasting effect and strong attracti...

Claims

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Application Information

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Patent Type & Authority Applications(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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