1,3,4-thiadiazole aroyl urea compound, preparation method and application thereof

A compound and thiadiazole technology, applied in 1 field, can solve the problems of human health hazards, ecological environment pollution, backward production supervision and management, etc., and achieve the effects of good sterilization effect, broad market prospect and simple process method.

Inactive Publication Date: 2009-02-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the extensive use of pesticides, coupled with supervision and management lagging behind production, resulting in pollution to the ecological environment and harm to human health

Method used

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  • 1,3,4-thiadiazole aroyl urea compound, preparation method and application thereof
  • 1,3,4-thiadiazole aroyl urea compound, preparation method and application thereof
  • 1,3,4-thiadiazole aroyl urea compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1 2, the preparation of 6-difluorobenzoyl isocyanate

[0057] At room temperature, place 0.24mol of oxalyl chloride, 120mL of 1,2-dichloroethane and 0.1mol of 2,6-difluorobenzamide in a 250mL four-necked flask equipped with a reflux condenser, and install a drying tube and tail gas Absorption device, it takes about 5 hours to react under electromagnetic stirring until no gas is produced. The 1,2-dichloroethane and oxalyl chloride were distilled off first under normal pressure and then under reduced pressure, and the residue was a colorless oily liquid sealed in a desiccator for later use.

Embodiment 2

[0058] Example 2 Preparation of 2,6-difluoro-N-[5-(4-nitro)-1,3,4-thiadiazole-2-amino]benzamide

[0059] In a 250mL four-necked flask equipped with mechanical stirring and dropping funnel, add 0.01mol 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole and 60ml toluene, 0.014mol of 2,6-difluorobenzoyl isocyanate prepared in Synthesis Example 1 was added dropwise, stirred and reacted, and detected by TLC until the reaction was complete, which took about 12 hours. After filtration, the filtrate was evaporated to remove part of the solvent and then cooled to obtain the crude product, which was recrystallized from DMF to obtain a pinkish-yellow powder (1.1 g, yield 76%), melting point: 258-259°C.

[0060] 1 H NMR: 7.26-8.60 (7H, m), 11.81 (1H, s), 12.13 (1H, s).

Embodiment 3

[0061] Example 3 Preparation of 2,6-difluoro-N-[5-(4-methoxy)-1,3,4-thiadiazole-2-amino]benzamide

[0062] In a 250 mL four-necked flask equipped with mechanical stirring and dropping funnel, add 0.01 mol of 2-amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole and 80 mL of toluene, and 0.014mol of 2,6-difluorobenzoyl isocyanate prepared in Synthesis Example 1 was added dropwise, stirred and reacted, and detected by TLC until the reaction was complete, which took about 8 hours. After filtering, the filtrate was evaporated to remove part of the solvent and then cooled to obtain the crude product, which was recrystallized from ethanol to obtain white crystals (1.4 g, yield 83%), melting point: 203-205°C.

[0063] 1 H NMR: 3.84 (3H, s), 7.07-7.90 (7H, m), 11.73 (2H, s).

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Abstract

The invention discloses a 1, 3, 4-thiadiazole aroyl urea compound and a preparation method and the application thereof, the compound or pharmaceutically acceptable salt can be shown by general formula (I), wherein, R1, R2 or R3 is respectively hydrogen, nitryl, alkoxy, halogen, alkyl, substituted alkyl or phenoxyl, and the substituent is halogen, nitryl, amino, alkoxy or hydroxyl; R4 or R5 is respectively hydrogen, alkoxy or halogen. The compound has the advantages of good sterilization effect, simple technique and broad market prospect.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a 1,3,4-thiadiazolyl aroyl urea derivative with insecticidal effect, a preparation method and application thereof. Background technique [0002] my country is a big agricultural country, and it is also one of the big countries that produce and consume pesticides. Due to the extensive use of pesticides and the supervision and management lagging behind the production, it has caused pollution to the ecological environment and harm to human health. According to statistics, the world's crop production loses 14% every year due to pests, 10% due to diseases, and 11% due to weeds. From planting to storage, due to the harm of diseases, insects, weeds and rats, at least 10%-15% of food is lost, about 15% of cotton is lost, and about 20% of fruits and vegetables are lost, and most of the above can be recovered through the use of pesticides Loss. The development of high-efficiency, l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/12A01N47/36A01P7/00
Inventor 万嵘王锦堂韩锋殷利河王斌
Owner NANJING UNIV OF TECH
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