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Method for synthesizing phyllocnistis citrella stainton pheromone compound

A technology of citrus leafminers and a synthesis method, which can be applied in the directions of oxidative preparation of carbonyl compounds, organic chemistry, etc., can solve problems such as large damage, rampant pests, and impact on consumers' health.

Inactive Publication Date: 2010-05-26
WENZHOU MEDICAL UNIV +1
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Problems solved by technology

What is more serious is the wound caused by leafminer damage to leaves and branches, which is most likely to be invaded by the pathogenic bacteria of citrus canker, causing even greater damage.
At present, the main method of its control still relies on chemical pesticides, such as pyrethroid pesticides, but the long-term unrestrained use of chemical pesticides not only has a partial killing effect on pests, but also kills a large number of natural enemies and destroys the ecological balance of the orchard; As a result, pesticide residues in fruits seriously exceed the standard, which seriously affects the health of consumers and hinders the export of fruits; at the same time, it induces pests to develop resistance to various conventional pesticides, causing pests to become rampant again

Method used

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  • Method for synthesizing phyllocnistis citrella stainton pheromone compound
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  • Method for synthesizing phyllocnistis citrella stainton pheromone compound

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Embodiment 1

[0045] A method for synthesizing sex pheromone compounds of citrus leafminer, comprising three compounds (Z)-7-hexadecenal, (Z, Z)-7,11-hexadecanal in citrus leafminer sex pheromone The synthetic method of carbadienal and (Z, Z, E)-7,11,13-hexadecatrienal;

[0046] A kind of synthetic method of (Z)-7-hexadecenal, its concrete steps are: take 1,7-heptanediol and brominated n-nonane as starting raw materials; 1,7-heptanediol undergoes unilateral Protection and oxidation reaction to obtain heptanal with unilateral hydroxyl protection; n-nonyltriphenylphosphine bromide obtained from the reaction of brominated n-nonane and triphenylphosphine after alkali treatment, and heptanal with unilateral hydroxyl protection Wittig reaction, the product obtained is through deprotection and oxidation reaction, synthesized (Z)-7-hexadecenal; chemical reaction equation is:

[0047]

[0048] Synthesis of Compound 4: Add 16.2 g (0.12 mol) of diol and toluene (500 mL) into a 1L three-necked flas...

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Abstract

The invention relates to a method for synthesizing a phyllocnistis citrella stainton pheromone compound. (Z)-7-hexadecene aldehyde is synthesized by using 1,7-heptandiol and bromo-n-nonane as starting materials and through six steps of reactions (comprising a Witting reaction); (Z,Z)-7,11-hexadecadienoic aldehyde is synthesized by using the 1,7-heptandiol, 1,4-butanediol and bromo-n-pentane as starting materials and through multi-step of reactions (comprising two Witting reactions); and (Z,Z,E)-7,11,13-hexadecatrienoic aldehyde is synthesized by using 2-octyne-1-alcohol, 1-iodine-3-chloropropane and trans-2-amylene aldehyde as starting materials and through multi-step of reactions (comprising a coupling reaction and a Witting reaction). The invention has the advantages of low price and easy obtaining of raw materials, simple and reasonable synthesizing route, convenient and safe operation and high utilization rate of the raw materials.

Description

【Technical field】 [0001] The invention relates to the technical field of citrus leaf miner sex pheromones, in particular to a synthesis method of citrus leaf miner sex pheromone compounds. 【Background technique】 [0002] Citrus leafminer (Phyllocnistis citrella stainton) belongs to Lepidoptera Lepidoptera, is the main pest of citrus, and is distributed in citrus producing areas all over the country. The larvae sneak into the skin of young leaves and young shoots to feed, and bore into irregular silver-white tunnels. Therefore, fruit farmers in Guangdong and Guangxi call them "ghost painting symbols". Tree growth and fruiting. The damaged leaf curls are often "refuges" and wintering places for pests such as leaf tortrixes, so it is very difficult to prevent and control them. What's more serious is that the wounds caused by leaf miners' damage to leaves and branches are most likely to be invaded by citrus canker pathogenic bacteria, causing even greater damage. At present, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/21C07C45/29
Inventor 陈海滨胡武新杜永均叶晓霞
Owner WENZHOU MEDICAL UNIV
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