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Thiobenzamide compounds and application thereof

An o-aminothiobenzamide and compound technology, which is applied in the field of thiobenzamide compounds, can solve the problem that the insecticidal activity of the thioamide compounds has not been disclosed, and achieves the improvement of effective utilization, reduction of influence, good solubility

Inactive Publication Date: 2013-05-22
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, the preparation of the thioamide compounds as shown in the present invention and their insecticidal activity have not been disclosed

Method used

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  • Thiobenzamide compounds and application thereof
  • Thiobenzamide compounds and application thereof
  • Thiobenzamide compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation of embodiment 1 compound 1

[0029] (1) Synthesis of 8-methyl-1H-[1,3]-benzoxazine-2,4-dione

[0030]

[0031] Into a 500mL reaction flask, add 15.1g (0.1mol) 2-amino-3-methylbenzoic acid, 150mL ethyl acetate, 0.5g pyridine, dropwise add 19.8g (0.067mol) Sanko Gas and 100mL of ethyl acetate, dropwise, stirred and reacted at 30-35°C for 4 hours, then raised the temperature and refluxed for 2 hours, removed all phosgene, cooled to room temperature, filtered with suction, and washed with water to obtain 15.9g of white solid, collected The rate is 89.8%.

[0032] (2) Synthesis of 2-amino-N,3-dimethylbenzamide

[0033]

[0034] Add 17.8g (0.1mol) of 8-methyl-1H-[1,3]-benzoxazine-2,4-dione, 100mL ethyl acetate, 1.5g glacial acetic acid in 15- Gradually add 15.5g (0.2mol) of 40% methylamine aqueous solution at 20°C, drop it, stir at room temperature for 2 hours, separate the liquids, leave to stand to separate the water layer, dry with anhydrous magnes...

Embodiment 2

[0045] The preparation of embodiment 2 compound 3

[0046] (1) Synthesis of 2-amino-3-methyl-5-chloro-N-allylthiobenzamide

[0047]

[0048] To a 500mL four-necked bottle, add P 2 S 5 22.2g (0.1mol), Na 2 CO 310.6g (0.1mol), ethyl acetate 200mL, stir at room temperature for 1h until the system is clear, add 22.45g (0.1mol) 2-amino-3-methyl-5-chloro-N-allylbenzamide in batches (prepared according to the method of Example 1), the temperature was raised to reflux for 6 hours, and after the reaction of the raw materials was complete, the temperature was lowered to room temperature, and 30 mL of water was added until the system was clarified, and the liquid was separated. The ethyl acetate layer was washed with a saturated saline solution (30 mL×2), and no Water Na 2 SO 4 After drying, the solvent was evaporated to dryness to obtain 17.3 g of an orange-yellow solid with a yield of 71.93%.

[0049] (2) Synthesis of compound 3

[0050]

[0051] Add 2.4g (0.01mol) 2-amin...

Embodiment 3

[0052] The preparation of embodiment 3 compound 7

[0053] (1) Synthesis of 2-amino-3-methyl-5-chloro-N-isopropylthiobenzamide

[0054]

[0055] To a 500mL four-necked bottle, add P 2 S 5 22.2g (0.1mol), Na 2 CO 3 10.6g (0.1mol), ethyl acetate 200mL, stirred at room temperature for 1h until the system was clear, added 2-amino-3-methyl-5-chloro-N-isopropylbenzamide (prepared according to the method in Example 1) in batches ) 22.65g (0.1mol), heat up to reflux for 6h, after the reaction of the raw materials is complete, cool down to room temperature, add 30mL of water until the system is clear, separate the layers, wash the ethyl acetate layer with saturated saline solution (30mL×2), anhydrous Na 2 SO 4 After drying, the solvent was evaporated to dryness to obtain 17.8 g of a yellow solid with a yield of 73.4%.

[0056] (2) Synthesis of compound 7

[0057]

[0058] Add 2.42g (0.01mol) 2-amino-3-methyl-5-chloro-N-isopropylthiobenzamide in 100mL reaction flask, 20mL ...

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Abstract

The invention discloses novel thiobenzamide compounds. The structure of the thiobenzamide compounds is shown as a general formula I, wherein R1 is selected from Cl or Br; R2 is selected from methyl, isopropyl or allyl; and R3 is selected from H or Cl. The compounds shown in the general formula I have excellent insecticidal activity, and can be used for the control on common pests in agriculture and forestry, especially the control on resistant pests.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and relates to a thiobenzamide compound and an application thereof. Background technique [0002] Pests have developed varying degrees of resistance to existing insecticides due to extensive and frequent use of pesticides. The development of insecticides with new mechanisms of action is an effective means to control pest resistance. With the improvement of people's quality of life and environmental protection requirements, the research and development of high-efficiency, safe and green insecticides meet the requirements of the development trend of pesticides. WO2003 / 015519 discloses the following compounds (KC) having insecticidal activity. This compound has been commercialized as an insecticide (commercial name: Kang Kuan), which has the characteristics of super high efficiency and long-lasting effect on lepidopteran pests, but has disadvantages such as poor solubility and few formulati...

Claims

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Application Information

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IPC IPC(8): A01N43/56A01P7/04C07D401/04
Inventor 许良忠田帅关立婷王明慧袁冰
Owner QINGDAO UNIV OF SCI & TECH
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