Hydrocarbon-oxygen imino group dibenzo caprolactam derivative, as well as preparation method of the derivative and application of the derivative in serving as bactericide

A fungicide, benzyl technology, applied in the field of alkoxyiminodibenzocaprolactam derivatives and its preparation and application as a fungicide, can solve the problems of long synthetic route, not wide activity spectrum, high cost, etc., and achieve raw material Inexpensive, simple reaction route, good growth inhibition effect

Inactive Publication Date: 2011-08-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the synthesis of 12-(alkoxyimino)-1,15-pentadecanone needs seven to eight steps with cyclododecanone as raw material, th

Method used

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  • Hydrocarbon-oxygen imino group dibenzo caprolactam derivative, as well as preparation method of the derivative and application of the derivative in serving as bactericide
  • Hydrocarbon-oxygen imino group dibenzo caprolactam derivative, as well as preparation method of the derivative and application of the derivative in serving as bactericide
  • Hydrocarbon-oxygen imino group dibenzo caprolactam derivative, as well as preparation method of the derivative and application of the derivative in serving as bactericide

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Experimental program
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Effect test

Embodiment 1

[0058] Embodiment 1, the synthesis of alkoxyiminodibenzocaprolactam derivatives (CAUWL-2010)

[0059] Add 3mmol of intermediate 1 (R1=H) or intermediate 2 (R1=Cl, Br, I) and 3.6mmol of alkoxyamine hydrochloride into 10mL of pyridine, stir at 90°C for 16 hours, and concentrate the reaction solution to After 2 mL, it was poured into water to produce a white solid, which was washed successively with appropriate amount of dilute hydrochloric acid and water, dried and recrystallized with ethyl acetate and petroleum ether (v / v=1:10) to obtain two isomers (Z and E) mixtures. The existence of cis-trans isomers was confirmed by HPLC-MS, and the ratio was basically 1:1. The physicochemical and mass spectrometry data of the compound CAUWL-2010 are shown in Table 2, and the proton nuclear magnetic resonance spectrum data of the compound CAUWL-2010 are shown in Table 3.

[0060] references:

[0061] Wild, Hanno; Roeben, Wolfgang; Aichinger, Gerd, et al.Preparation of 5,6-dihydro-dibenz[...

Embodiment 2

[0062] Embodiment 2, the preparation of compound CAUWL-2010 emulsifiable concentrate

[0063] Add 1-10g of compound CAUWL-2010, 5-15g of emulsifier, and 0.1-1g of penetrant into a 100ml volumetric flask, and then use solvents such as toluene, xylene, etc. to dilute to obtain an emulsifiable concentrate with a content of 1-10%.

Embodiment 3

[0064] Embodiment 3, the preparation of compound CAUWL-2010 wettable powder

[0065] Take 15-50 g of compound CAUWL-2010, 10-20 g of surfactant, and 30-75 g of white carbon black, mix and pulverize to obtain a wettable powder with a content of 15-50%.

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Abstract

The invention discloses a hydrocarbon-oxygen imino group dibenzo caprolactam derivative CAUWL-2010, as well as a preparation method an application of the derivative. The constitutional formula of the derivative CAUWL-2010 is shown as in formula I, wherein R1 is H, C1, Br or I, R2 is C1-C4 alkyl, allyl, n-heptyl, myristyl, hexadecyl, benzyl or benzyl with 1-2 substituents; and the substituents in the benzyl with 1-2 substituents are F, C1, CH3, CF3 or NO2. The compound CAUWL-2010 is obtained by the reaction of the compound shown in the formula II with hydrocarbon-oxygen amine hydrochloride. Through bactericidal activity, the result indicates that both the compound CAUWL-2010 and the preparation of the compound CAUWL-2010 have excellent restraining effect for the growth of sclerotinia scleotiorum, cucumber Botrytis Cinerea, asparagus phomopsis asparagi and pyricularia grisea. (formula I) (formula II).

Description

technical field [0001] The invention relates to alkoxyimino dibenzocaprolactam derivatives, a preparation method thereof and an application as a fungicide. Background technique [0002] Chinese invention patent (ZL03156154.3) provides a preparation method of 12-(alkoxyimino)-1,15-pentadecanolactam and its use as a fungicide. But the synthesis of 12-(alkoxyimino)-1,15-pentadecanone needs seven to eight steps with cyclododecanone as raw material, the synthetic route is long, and the cost is higher; and the activity spectrum is not wide, only for two The pathogen is active. Contents of the invention [0003] The object of the present invention is to provide alkoxyiminodibenzocaprolactam derivative CAUWL-2010 and its preparation method. [0004] The structural formula of the compound CAUWL-2010 provided by the present invention is shown in formula I: [0005] [0006] (Formula I) [0007] In the formula, R 1 is H, Cl, Br or I, R 2 C1-C4 alkyl, allyl, n-heptyl, tetrade...

Claims

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Application Information

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IPC IPC(8): C07D223/20A01N43/46A01P3/00
Inventor 梁晓梅王道全张建军肖炎双
Owner CHINA AGRI UNIV
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