Methylene diphenyl amide compound and application thereof

A technology of methylene diphenylamides and compounds, which is applied in the field of methylene diphenylamides and their application as agricultural fungicides, and can solve the problem of unseen applications of methylene diphenylamides problems such as reports, to achieve the effect of high inhibitory activity, simple structure and good control effect

Inactive Publication Date: 2015-05-13
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, there is no report on the application of methylene diphenylamides in pesticides

Method used

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  • Methylene diphenyl amide compound and application thereof
  • Methylene diphenyl amide compound and application thereof
  • Methylene diphenyl amide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] compound (C 23 h 18 N 2 o 4 ) preparation

[0028] (1) Add 0.01mol of furan-2-carboxylic acid and 15mL of thionyl chloride to a 50mL three-necked flask, heat to 80°C and reflux for 2 hours, distill off excess thionyl chloride until no liquid flows out, Cool to room temperature to obtain furan-2-formyl chloride.

[0029] (2) Add 0.005mol 4,4,-diaminodiphenylmethane and 10mL dichloromethane into a 50mL three-neck flask, add 3mL triethylamine or pyridine, and add the newly prepared furan-2 dropwise under stirring at room temperature - formyl chloride. After the dropwise addition, continue the reaction at 35-55°C for 3 hours. After the reaction is complete, wash the reaction mixture with 10% hydrochloric acid, 10% NaOH and distilled water to neutrality, and place it in a refrigerator at 2-6°C until the solid precipitates Afterwards, filter, wash, and recrystallize with dimethyl sulfoxide and water to obtain a dark green crystalline product with a yield of 61%. The ...

Embodiment 2

[0033] compound (C 23 h 18 N 2 o 2 S 2 ) preparation

[0034] (1) Add 0.01mol thiophene-2-carboxylic acid and 15mL thionyl chloride to a 50mL three-neck flask, heat to 80°C and reflux for 2 hours, and distill off excess thionyl chloride until no liquid flows out, Cool to room temperature to obtain thiophene-2-formyl chloride.

[0035] (2) Add 0.005mol 4,4,-diaminodiphenylmethane and 10mL dichloromethane into a 50mL three-neck flask, add 3mL triethylamine or pyridine, and add the newly prepared thiophene-2 ​​dropwise under stirring at room temperature - formyl chloride. After the dropwise addition, continue the reaction at 35-55°C for 3 hours. After the reaction is complete, wash the reaction mixture with 10% hydrochloric acid, 10% NaOH and distilled water to neutrality, and place it in a refrigerator at 2-6°C until the solid precipitates Afterwards, filter, wash, and recrystallize with dimethyl sulfoxide and water to obtain a light yellow crystal product with a yield ...

Embodiment 3

[0039] Determination of Antibacterial Activity of Methylene Diphenylamide Compounds against Phytopathogenic Fungi

[0040] 1. Plant pathogenic fungi tested

[0041] Rice sheath blight, wheat head blight, corn spot blight, rapeseed sclerotinia, tomato cinerea, potato infestation, melon anthracnose, grape white rot, citrus green mold, and apple ringworm .

[0042] 2. Experimental method

[0043] The test compound was dissolved in dimethyl sulfoxide, then added to tap water containing 0.1% Tween-80, and mixed uniformly to form a 200 mg / L test solution. This solution was added to the sterilized PDA medium, and at the same time, streptomycin at a concentration of 50 mg / L was added. Using the corresponding solution not containing the test compound as the blank control, make a drug-containing flat plate with uniform thickness for use, and repeat three times. Use a sterilized hole puncher to select Ф5mm well-grown, non-polluted, and uniformly growing bacterial cakes, and insert th...

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Abstract

The invention discloses a methylene diphenyl amide compound and application thereof and relates to the field of agricultural fungicides. The compound has a structure represented by a general formula (I) as shown in the description, wherein X is an oxygen atom or a sulfur atom; and R is a hydrogen atom, a halogen atom, C1-C4 alkyl group or an alkoxy group, or a nitro group. The methylene diphenyl amide compound is simple in structure, and has good inhibitory activity on multiple plant pathogenic fungi such as bipolaris maydis and sclerotinia sclerotiorum. The methylene diphenyl amide compound can be used for preventing and controlling plant pathogenic fungi, which is a novel application of the compound in the field of pesticides.

Description

technical field [0001] The invention relates to the field of agricultural fungicides, in particular to methylene diphenylamide compounds and their application as agricultural fungicides. Background technique [0002] Pesticide resistance has always been an unavoidable problem in the control of agricultural diseases and insect pests. After a period of use of pesticides, pests or pathogenic bacteria will develop resistance to them, especially for some pesticides with strong targets, the resistance will develop faster. Therefore, in the face of this problem, there is a constant need to invent new and improved compounds and compositions with insecticidal or fungicidal activity in the control of agricultural diseases and insect pests. At the same time, along with people's increasing demand for agricultural and livestock products and increasing emphasis on environmental protection, new pesticides with lower cost and environmental friendliness are always required. [0003] Since ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C07D333/38A01N43/08A01N43/10A01P3/00
CPCA01N43/08A01N43/10C07D307/68C07D333/38
Inventor 唐孝荣王雪松高扬高素美杨建徐志宏张燕王玲
Owner XIHUA UNIV
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