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Benzimidazole amide bactericide

A technology of benzimidazolone amide and agricultural fungicide, applied in the field of pesticides, can solve problems such as unreported bacteriostatic activity, and achieve the effects of high reaction yield and product purity, simple raw materials, and few synthesis steps

Inactive Publication Date: 2011-07-20
PESTICIDE INST XIBEI AGRI & FORESTRY TECHUNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of compound is rarely reported in the literature, and its antibacterial activity has not been reported

Method used

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  • Benzimidazole amide bactericide
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  • Benzimidazole amide bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1. Synthesis of 1-(prop-1-en-2-yl)-3-propionyl-1H-benzimidazol-2-one

[0029] In the reaction flask equipped with a water separator, add 54g (0.5mol) o-phenylenediamine and 220mL xylene, after heating and stirring to reflux, slowly add 71.5g (0.55mol) of ethyl acetoacetate and mix with 20mL xylene After dripping, stir and reflux for azeotropic dehydration until no water drops appear, then continue to stir and reflux for 2 hours. After completion of the reaction, cool down to precipitate crystals, filter and dry to obtain 76.5 g of white granular crystals (yield 87.9%), which is the intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazole-2- Ketone, melting point 120~122℃. Take 1.74g (0.01mol) of the intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one and 0.01mol of triethylamine dissolved in 30mL of toluene, add dropwise at room temperature 0.01mol of propionyl chloride solution (0.92g of acryloyl chloride dissolved in 10mL of toluene), stirred at room tempera...

Embodiment 2

[0032] 2. Synthesis of 1-acryloyl-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

[0033] The synthesis of the intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one is the same as in Example 1. Take 1.74g (0.01mol) of intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one and 0.01mol of triethylamine dissolved in 30mL of toluene, add dropwise at room temperature 0.01mol of acryloyl chloride solution (0.90g of acryloyl chloride dissolved in 10mL of toluene), stirred at room temperature for 5-8 hours, washed three times with water, dried and precipitated to obtain 2.11g of the target compound (92.5% yield), melting point 108-110°C .

[0034]

Embodiment 3

[0036] 3. Synthesis of 1-(3-chloropropionyl-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

[0037] The synthesis of the intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one is the same as in Example 1. Take 1.74g (0.01mol) of intermediate 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one and 0.01mol of triethylamine dissolved in 30mL of toluene, add dropwise at room temperature 0.01mol 3-chloropropionyl chloride solution (1.26g 3-chloropropionyl chloride dissolved in 10mL toluene), stirred at room temperature for 5-8h, washed three times with water, dried and precipitated to obtain 2.23g of the target compound (84.4% yield) , Melting point 110~112℃.

[0038]

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Abstract

The present invention relates to a novel benzimidazole amide compound and an application thereof as an agricultural bactericide, belonging to the technical field of pesticides. The compound has the structural formula disclosed in the specification, wherein R represents an alkyl group with a carbon chain length of C2-C4, specifically an ethyl, a propyl, a normal-butyl and an isobutyl; an alkenylwith a carbon chain length of C2-C4, specifically a vinyl, an allyl, an isopropenyl and an isobutenyl; a halogenated alkyl with a carbon chain length of C1-C2, specifically a chloromethyl group, a brooethyl, a 2-chloroethane and a 2-bromomethyl; and different substituted aryl groups specifically refer to a parachloro-penyl methyl, a p-bromophenyl methyl, a p-methoxybenzene methyl, a p-nitro phenyl; and a furfuryl.

Description

technical field [0001] The technical scheme of the invention relates to a class of benzimidazolone amide fungicides, belonging to the technical field of pesticides. Background technique [0002] Crop disease is an important factor leading to the reduction of yield and quality of agricultural products, and chemical control is the main technical means of crop disease control. Organic synthetic fungicides are the main part of the current agricultural fungicides and an important part of the modern pesticide industry. However, the problem that cannot be ignored is that with the extensive use of organic synthetic fungicides, crop pathogens have shown different degrees of drug resistance or drug resistance. In order to solve this problem, it is a continuous problem faced by the pesticide industry to continuously develop various new fungicides. [0003] Since benomyl was discovered in 1968 to have excellent properties of preventing and controlling fungal diseases, the bactericidal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/26A01N43/52A01P3/00
Inventor 姬志勤吴文君张继文李圣坤
Owner PESTICIDE INST XIBEI AGRI & FORESTRY TECHUNIV