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[E]-beta-farnesene analogue, preparing method and application of the same

A condensation reaction and compound technology, which is applied to [trans]-β-farnesene analogs and the fields of preparation and application thereof, can solve the problems of effective utilization of unfavorable aphids and poor stability, and achieve good chemical killing activity and stability. Good, simple effect of product purification method

Inactive Publication Date: 2009-12-09
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the existence of conjugated double bonds in the EBF molecule, the stability is poor due to easy oxidation, which is not conducive to its effective use in actual aphid control. Therefore, many scholars have carried out structural modification and modification of the EBF molecule in order to find that both activity and stability compound of

Method used

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  • [E]-beta-farnesene analogue, preparing method and application of the same
  • [E]-beta-farnesene analogue, preparing method and application of the same
  • [E]-beta-farnesene analogue, preparing method and application of the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, preparation of [anti]-β-farnesene analog compound 3-(3,7-dimethyl-2,6-octadienyl)-2-carbonyl-1,3 oxazolidine

[0034]In a 100mL three-necked flask, put 4.3g of 2-carbonyl-1,3 oxazolidine (compound represented by formula H, wherein Y is O, Z is O, provided by Beijing Shubowei Chemical Instrument Co., Ltd., product number 09409- 100G), 1.5g of sodium hydroxide (basic compound) and 30mL of acetonitrile, stirred, to which 7mL of acetonitrile solution containing 8.3g of 1-chloro-3,7-dimethyl-2,6-octadiene was added dropwise, After the dropwise addition was completed, the reaction was carried out at 40°C for 5h. The reaction solution was cooled to room temperature, filtered with a Buchner funnel with a diameter of 10 cm, and the solid was washed with acetonitrile. After the filtrates were combined, the solvent was removed under reduced pressure to obtain a red liquid, and then the product after the solvent removal was directly passed through a silica gel column ...

Embodiment 2

[0039] Embodiment 2, preparation of [anti]-β-farnesene analog compound 3-(3,7-dimethyl-2,6-octadienyl)-2-thiazolethione

[0040] According to the preparation method of Example 1, 3-(3,7-dimethyl-2,6-octadienyl)-2-thiazolethione was prepared, wherein, 2-thiazolethione (the compound shown in formula II, Wherein Y is S, Z is S, purchased from Beijing Shubowei Chemical Instrument Co., Ltd., item number M6204-100G) as the reaction raw material to replace 2-carbonyl-1,3 oxazolidine, the solvent used is toluene, and sodium hydride is used instead of hydroxide Sodium, the reaction temperature is 80°C, and the reaction time is 8h.

[0041] According to the purification method described in Example 1, the product after the reaction was purified to obtain 5.6 g of a light yellow liquid product, which was 3-(3,7-dimethyl-2,6-octadienyl)-2-thiazole Thione (Y in formula I is s, Z is s), the yield is 45%.

[0042] After element analysis, the result is C 61.32, H 8.23, N 5.45, theoretical va...

Embodiment 3

[0046] Embodiment 3, [anti]-β-farnesene analog compound 3-(3,-dimethyl-2,6-octadienyl)-2-cyanoimino-1,3 thiazolidine ( Compound shown in formula V) preparation

[0047] According to the preparation method of Example 1, 3-(3,7-dimethyl-2,6-octadienyl)-2-thiazolethione was prepared, wherein, with 2-cyanoimino-1,3 thiazolidine (the compound shown in formula II, wherein Y is S, Z is NCN, purchased from Jiangsu Yixing Chemical Co., Ltd., product number 26363-65-8) is the reaction raw material to replace 2-carbonyl-1,3 oxazolidine, and the solvent used is N,N-dimethylformamide, the basic substance used is pyridine, the reaction temperature is 100°C, and the reaction time is 6h.

[0048] According to the purification method described in Example 1, the product after the reaction was purified to obtain 13 g of a light yellow liquid product, which was 3-(3,7-dimethyl-2,6-octadienyl)-2-cyano Imino-1,3 thiazolidine (Y in formula I is s, Z is NCN), the yield is 52.0%.

[0049] After ele...

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Abstract

The invention discloses a [trans]-β-farnesene analogue, a preparation method thereof and an application thereof. The [trans]-β-farnesene analog is a compound represented by formula I, wherein, in formula I, Y is O or S, and Z is O, S or NCN. The compound of the present invention has good chemical killing activity on aphids, especially at low concentrations, the aphidicidal activity of the compound of the present invention is better than that of the contrast agent thiacloprid, and compared with EBF, the compound of the present invention has a large molecular weight and stable Well, it can be practically applied in agricultural production.

Description

technical field [0001] The present invention relates to [trans]-β-farnesene analogs and their preparation methods and applications, in particular to a nitrogen-containing five-membered heterocyclic [trans]-β-farnesene analogs and their preparation methods and the Use of compounds in the control of aphids. Background technique [0002] Aphids are an important class of pests that endanger agricultural and forestry production worldwide, with the characteristics of various species and rapid reproduction. It mainly harms crops by directly eating and spreading plant viruses. At least 159 species of aphids are known to be able to carry plant viruses, ranking first in the world among insects that transmit viruses. Aphid control has always been a hot spot in the research of pest control in the agricultural field. one. Especially in recent years, the international environmental quality requirements have been gradually improved and the problems of traditional pesticides have become i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/12A01N43/76A01P7/00
Inventor 杨新玲康铁牛凌云孙玉凤王晓波陈馥衡
Owner CHINA AGRI UNIV
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