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3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof

A 5-d, pyrimidine technology, applied in the field of biological activity, can solve the problem of little pesticide activity

Inactive Publication Date: 2014-09-24
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

We noticed that: from most of the literature reports, this kind of compound mainly shows pharmacological activity, and its pesticide activity is rarely reported

Method used

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  • 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof
  • 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof
  • 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imide-5-methylthio-7-ethylthio pyrimido[4,5-d]pyrimidine with herbicidal activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Compound 1 preparation of

[0017] 3-O-fluorobenzamido-3,4-dihydro-4-imine-5,7-dimethylthiopyrimido[4,5-d]pyrimidine

[0018]

[0019] In a 50mL round bottom flask, add 0.05mol 4-amino-5-cyano-2,6 dimethylthiopyrimidine, 0.015mol triethyl orthoformate and a catalytic amount of trifluoroacetic acid, stir and heat to reflux for 8-9 Hour. After the reaction, the unreacted triethyl orthoformate was removed under reduced pressure, and the residue was washed several times with petroleum ether to obtain a light yellow solid 4-ethoxymethyleneamino-5-cyano-2,6-dimethylthio Pyrimidine, melting point 128-129°C, yield 73%.

[0020] Add 0.001 mol of 4-ethoxymethyleneamino-5-cyano-2,6-dimethylthiopyrimidine, 0.001 mol of fluoro-substituted benzohydrazide and 10 mL of ethylene glycol methyl ether into a 50 mL round bottom flask , stirred and heated to reflux for 3-5 hours. Cool and filter. The filter cake was washed several times with a small amount of ether, and dr...

Embodiment 2

[0173] Herbicidal activity experiment

[0174] Experimental Materials:

[0175] One electronic balance, beaker, dropper, pipette, ear washing ball, Petri dish, round filter paper, scale, distilled water, DMF, emulsifier (Tween-80), and samples to be tested.

[0176]The tested plants were Barnyard grass (Monocotyledonous plants), cucumber (Cucumber, Dicotyledonous plants), wheat (Wheat, Monocotyledonous plants), radish (Radish, Gemini Dicotyledonous plants).

[0177] testing method:

[0178] Herbicidal activity was tested using isolated petri dishes:

[0179] Weigh 3-5 mg of the sample to be tested with an electronic balance, add a small amount of DMF to dissolve, add 1 drop of emulsifier (Tween-80), and add 3-5 mL of distilled water to make a 1000 mg / L solution. Take 1 mL of this solution and add distilled water Dilute to 10mL to make 100mg / L sample solution. Also take 1mL 100mg / L sample solution and dilute to 10mL with distilled water to make 10mg / L sample solution. Us...

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Abstract

The general formula is shown in the following formula I. Herbicidally active 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imine-5-methylthio-7-ethylthiopyrimido[4,5 -d] pyrimidines. In the formula, R1 represents an n-alkyl group; R2 represents a fluorine-containing substituted phenyl group. These compounds have significant inhibitory effects on the growth of monocotyledonous or dicotyledonous plants, and are effective components of herbicides.

Description

technical field [0001] The present invention relates to 3-fluorine-containing substituted benzamido-3,4-dihydro-4-imine-5-methylthio-7-ethylthiopyrimido[4,5-d]pyrimidine with herbicidal activity Preparation of its intermediates, and its biological activity as a herbicide. Background technique [0002] Since the van der Waals radius of the fluorine atom is the closest to that of the hydrogen atom, the electronegativity is large and the bond energy of the carbon-fluorine bond is large, and the fluorine atom also has four effects: simulation effect, electronic effect, hindrance effect and penetration effect, its introduction It is possible to double the biological activity of the compound, so the study of fluorine-containing compounds is also very active. Scientists have discovered that introducing fluorine atoms and fluorine-containing groups into physiologically active heterocyclic compounds can greatly improve their physiological activity without causing teratogenic and car...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A01N43/90A01P13/00
Inventor 王涛罗劲徐晓明刘雪英顾成浩王文娟李志强汤君于丹红
Owner JIANGXI NORMAL UNIV