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3,5-dihalogenation sulfo-benzamide insecticide

A dihalothiobenzamide and insecticide technology, applied in 3 fields, can solve the problems of undisclosed insecticidal activity, achieve good comprehensive performance, wide source of production raw materials, and low synthesis cost

Inactive Publication Date: 2013-06-05
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japan Pesticide Company, U.S. DuPont and Bayer Agricultural Science and Technology have carried out systematic research work on the structural transformation of this type of insecticide, but in the prior art, as shown in the present invention, 3,5-dihalothio Benzamide insecticides and their insecticidal activity have not been disclosed

Method used

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  • 3,5-dihalogenation sulfo-benzamide insecticide

Examples

Experimental program
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Effect test

example 1

[0024] The preparation of example 1 compound 1

[0025] (1) Preparation of 2-amino-N-methylbenzamide

[0026]

[0027] In a 250mL reaction flask, add 16.3g (0.1mol) of isatoic anhydride, 100mL of ethyl acetate, 1mL of glacial acetic acid, add 15.5g (0.15mol) of 40% methylamine aqueous solution dropwise under stirring at room temperature, continue stirring for 2 hours, The disappearance of raw materials was detected by layer chromatography (TLC), and ethyl acetate and water were distilled off to obtain 13.2 g of white solid with a yield of 88%.

[0028] (2) Synthesis of 2-amino-3,5-dichloro-N-methylbenzamide

[0029]

[0030] In a 250mL reaction flask, add 15g (0.1mol) of 2-amino-N-methylbenzamide, add 80mL of acetonitrile, control the temperature in an ice bath below 10°C, slowly add 33.75g (0.25mol) of sulfonyl chloride dropwise, dropwise over 30 minutes Complete, stir at room temperature for 3h, evaporate most of the acetonitrile under reduced pressure, and use 20% N...

example 2

[0037] The preparation of example 2 compound 10

[0038] (1) Preparation of 2-amino-N-isopropylbenzamide

[0039]

[0040] In a 250mL reaction flask, add 16.3g (0.1mol) isatoic anhydride, 100mL ethyl acetate, 1mL glacial acetic acid, raise the temperature to 40-50°C, add 8.85g (0.15mol) of isopropylamine dropwise, continue to stir for 2h, and detect by TLC The raw materials disappeared, and ethyl acetate and water were distilled off to obtain 16.9 g of white solid, with a yield of 94.9%.

[0041] (2) 2-amino-3, the preparation of 5 dibromo-N-isopropylbenzamides

[0042]

[0043] In a 250mL reaction flask, add 17.8g (0.1mol) of 2-amino-N-isopropylbenzamide, 100mL of glacial acetic acid, add 32g (0.2mol) of bromine dropwise at room temperature, continue to stir for 3h, suction filter, filter Saturated Na 2 CO 3 After washing with aqueous solution and water, 32.4 g of white solid was obtained, with a yield of 96.3%.

[0044] (3) Preparation of 2-amino-3,5 dibromo-N-iso...

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Abstract

The invention discloses a 3,5-dihalogenation sulfo-benzamide insecticide and preparation method and application thereof. The 3,5-dihalogenation sulfo-benzamide insecticide is represented as a structural formula I. In the formula I: R1 is C1 or Br, R2 is selected from methyl, isopropyl and allyl, and R3 is H or C1. The 3,5-dihalogenation sulfo-benzamide insecticide can be used for prevention and control of agricultural insects or forest insects.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and relates to a 3,5-dihalothiobenzamide insecticide. Background technique [0002] Conventional pesticides such as organophosphorus and carbamates are commonly used in the control of pests. Not only do they have problems such as high toxicity and residues, but they have also produced serious resistance to insecticides. The development of new mechanisms of action and highly active green insecticides is the future of agricultural insecticides. direction of development. WO2003 / 015519 discloses a compound KC (formula II) with insecticidal activity. The compound has the characteristics of super high efficiency, long-lasting effect, low resistance and low toxicity against Lepidoptera pests, and is a typical green and environmentally friendly insecticide. Japan Pesticide Company, U.S. DuPont and Bayer Agricultural Science and Technology have carried out systematic research work on the structura...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCA01N43/56C07D401/04
Inventor 许良忠田帅刘春风陈慰燕王明慧袁冰
Owner QINGDAO UNIV OF SCI & TECH
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