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Pyrethroid compound, and preparation method and applications thereof

A technology for pyrethroids and compounds, applied in the field of pyrethroid compounds and their preparation, can solve the problems of low activity, phytotoxicity and the like

Inactive Publication Date: 2013-09-25
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of biological activity, some chiral compounds show high insecticidal, acaricidal, bactericidal or herbicidal activities, while their enantiomers show low activity or are phytotoxic.

Method used

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  • Pyrethroid compound, and preparation method and applications thereof
  • Pyrethroid compound, and preparation method and applications thereof
  • Pyrethroid compound, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The structure of some compounds of the present invention is one of the specific compounds listed in Table 1:

[0029] Table 1 List of representative compound structures

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

Embodiment 2

[0037] For the preparation of polysubstituted carboxylic acids, take intermediate III-1 as an example.

[0038]

[0039] Add compound II-1 (8mmol) into a 100mL single-necked flask, then add 40mL of tetrahydrofuran and stir to dissolve it, then add 10mL of water, cool the reaction solution to 0°C, add lithium hydroxide (9.6mmol) and Hydrogen peroxide (19.2mmol), react at 0°C for 24h, add a small amount of sodium sulfite to remove excess hydrogen peroxide, add dilute hydrochloric acid dropwise to adjust the pH of the solution to 2-3, extract with ether (2x30mL), wash the organic phase with saturated brine (50mL) and water, Anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to obtain the crude product III-1, which is directly used in the next reaction.

Embodiment 3

[0041] For the preparation of pyrethroid compounds, take compound I-A1 as an example.

[0042]

[0043] Weigh the crude product III-1 (1 g) from the previous step, add thymol 0.31 g (2.08 mmol), acetonitrile (10 mL), stir to dissolve, then add catalytic amount of DMAP (0.1 g) and condensation agent DCC 0.515g (2.50 mmol), stirred at room temperature for 16 h, removed DCU by suction filtration, washed the filtrate with aqueous sodium carbonate (2x30 mL), extracted with ethyl acetate (2x30 mL), combined the organic phase, and washed the organic phase with saturated brine ( 50 mL), washed with water, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to obtain a crude product, which is separated by column chromatography to obtain compound I-A1. The basic physical and chemical properties of the target compound I-A1 are as follows: White solid, mp: 53-54 o C. IR (KBr): υ 3063, 3029, 2960, 2917, 2865, 1745, 1505, 1486, 1454, 1136, 816, 757, 69...

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Abstract

The invention discloses a pyrethroid compound having a structure represented by general formula (I). The invention also discloses a preparation method of the compound, and uses of the compound. The method comprises the following steps: utilizing a chiral adjuvant induced asymmetric syntheses technology to construct a novel pyrethroid key intermediate chiral carboxylic acid, and condensing the chiral carboxylic acid with active molecules comprising plant essential oil micromolecules, substituted cyanohydrin, fluorine-containing benzyl alcohol and the like to obtain the novel pyrethroid compound. The pyrethroid compound is used for preparing pesticides or pesticide active components for killing important agricultural pests comprising cotton bollworms, diamondback moths, aphids, beet armyworms, armyworms and the like, and healthy pests comprising houseflies, Culex pipiens pallens and the like, and can be widely used for the comprehensive control of crop pests.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a pyrethroid compound and its preparation method and application. Background technique [0002] Nobuo Ohno of Japan's Sumitomo Chemical Company reported in 1974 that substituted phenylacetate compounds had excellent insecticidal activity and stable properties. This discovery led to the first commercialization and marketing of the photostable pyrethroid racemic compound fenvalerate in 1976. Then, in 1986, the single (S, S) isomer product esfenvalerate (Esfenvalerate) was put on the market, and its insecticidal activity was about four times that of its racemic compound (esfenvalerate). S-fenvalerate is a high-efficiency, broad-spectrum contact insecticide, which has certain stomach toxicity and no systemic activity, and can control various pests. However, pests are easy to develop resistance to it, and it is highly toxic to fish. [0003] In recent decades,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/616C07C69/65C07C69/734C07C69/86C07C255/38C07C67/08C07C253/30A01N37/10A01N37/38A01N37/40A01P7/04A01P7/02
Inventor 曹秀芳李皇勇韩勰汪淼徐胜臻陈长水
Owner HUAZHONG AGRI UNIV
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