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New benzoyl urea compound and its synthesis and application

A technology for benzoyl urea and compounds, which is applied in the field of benzoyl urea compounds and their synthesis and application, and can solve problems such as high process requirements, increased overall synthesis difficulty, and uneconomical

Inactive Publication Date: 2005-11-23
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantages are: the structure of the phenyl part is complicated, it is difficult to synthesize, and the process requirements are high, thereby increasing the difficulty of the overall synthesis, high cost, and uneconomical

Method used

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  • New benzoyl urea compound and its synthesis and application
  • New benzoyl urea compound and its synthesis and application
  • New benzoyl urea compound and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0175] Preparation of N-(2,6-difluorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea: Weigh 0.1 mole of freshly prepared benzoyl isocyanate (II-2), Use dry 1,2-dichloroethane to dissolve and dilute it in a flask equipped with a stirrer; weigh 0.1 mole of aniline derivative V-1, and also use dry 1,2-dichloroethane to make it Dissolve into a solution, then slowly drop it into the reaction bottle cooled with ice cubes while stirring, and immediately precipitate a white solid. After the heat release is complete, continue to react at room temperature for 3 to 4 hours, heat back to reflux water for 1 hour, cool, and filter with suction Get solid. Recrystallized with ethyl acetate to obtain 35.2 g of white needle-like crystals N-(2,6-difluorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea (I-1), producing The rate is 92.6%.

Embodiment 2

[0177] Preparation of N-(2-chlorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea: Weigh 0.1 mole of freshly prepared benzoyl isocyanate (II-1), dry it with 1 , 2-dichloroethane to dissolve and dilute it in a flask equipped with a stirrer; take another 0.1 mole of aniline derivative V-1, and also use dry 1,2-dichloroethane to dissolve it into a solution , and then slowly dripped into the reaction flask cooled with ice cubes under stirring, and a white solid was precipitated immediately. After the exotherm was completed, the reaction was continued at room temperature for 3 to 4 hours, heated to reflux water for 1 hour, cooled, and suction filtered to obtain a solid. Recrystallized with ethyl acetate to obtain 34.7 g of white needle-like crystal N-(2-chlorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea (I-2), yield 91.8% .

Embodiment 3

[0179] Preparation of N-(2,6-dichlorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea: Weigh 0.1 mole of freshly prepared benzoyl isocyanate (II-3), Use dry 1,2-dichloroethane to dissolve and dilute it in a flask equipped with a stirrer; weigh 0.1 mole of aniline derivative V-1, and also use dry 1,2-dichloroethane to make it Dissolve into a solution, then slowly drop it into the reaction bottle cooled with ice cubes while stirring, and immediately precipitate a white solid. After the heat release is complete, continue to react at room temperature for 3 to 4 hours, heat back to reflux water for 1 hour, cool, and filter with suction Get solid. Recrystallization with ethyl acetate gave 37.4 grams of white needle-like crystals N-(2,6-dichlorobenzoyl)-N'-(2,3,5-trichlorophenyl)urea (I-3), producing The rate is 90.7%.

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Abstract

The synthesis process of new benzoyl urea compound includes the fluorination of chlorothalonil, the separate amination of chlorothalonil and the fluorinated product, the hydrolysis and decarboxylation of the aminated product in sulfuric acid solution to obtain compound V; the hydrolysis of compound VI in sulfuric acid solution to obtain compound VII, the reaction between compound VII and oxalyl chloride to obtain compound II; and the reaction of compound V and compound II. The benzoyl urea compound of the present invention has no halogen element in the place 4 of the phenyl group but very activity, and this has important theoretical significance. Practically, the present invention opens one new way of preparing benzoyl urea compound as insect growth regulator and the production line is short, mild in reaction condition, high in yield, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to preparation of benzoyl urea compounds by using compound halogenated benzoyl isocyanate and compound trihalogenated aniline or dihalogenated phenylenediamine, and the novel compound is used for killing diamondback moth, armyworm and mosquito. Background technique [0002] Among the existing phenylmethyl urea compounds, people have proved that a class of compounds whose basic structure is N-phenyl-N'-substituted benzoyl urea has a higher killing effect on pests through a large number of experiments. Insect activity, and has higher safety to beneficial aquatic crustacea, belongs to insect growth regulator. One of the better representatives is pyridron. Flubron has the following advantages: 1. Unique mechanism of action, low toxicity to beneficial organisms, easy to degrade, high selectivity, relatively safe, and is an insect growth regulator. 2. High biological activity, low effective dosage. 3. Has broad-spectrum insecticidal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N47/28C07C273/02C07C275/32
Inventor 林军严胜骄杨丽娟宗乾收徐蓉冒德寿刘复初
Owner YUNNAN UNIV
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