Double amide derivative containing sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing pyrazolecarboxamide and preparing method and purpose thereof

A technology of cyanomethylsulfiminomethylene and pyrazole carboxamide, which is applied in the field of diamide derivatives and can solve the problems of limited number of pesticides

Inactive Publication Date: 2013-12-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although bisamide insecticides have shown outstanding advantages in terms of activity, pests have shown varying degrees of resistance due to frequent over-application in some areas, and the number of commercialized varieties of this type of insecticides is very limited so far.

Method used

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  • Double amide derivative containing sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing pyrazolecarboxamide and preparing method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0062] The synthesis of embodiment 13-methyl-5-substituted-2-aminobenzoic acid III:

[0063] (1) Synthesis of 3-methyl-5-chloro(bromo)-2-aminobenzoic acid

[0064]

[0065] Add 20 mmoles of 3-methyl-2-aminobenzoic acid, 50 milliliters of DMF, 30 mmoles of N-chlorosuccinimide (or N-bromosuccinimide) in a 100-ml round-bottomed flask, and reflux After stirring for 3 hours, the reaction solution was poured into ice water, acidified with dilute hydrochloric acid to pH = 6, filtered, and the obtained solid was washed with a small amount of ethanol to obtain gray solid chlorinated or brominated anthranilic acid III with a yield of 83%. Y is selected from: chlorine, bromine. Among them, 3-methyl-5-chloro-2-aminobenzoic acid 1 H NMR (400MHz, DMS0-d 6 ): δ: 7.56 (d, 1H), 7.23 (d, 1H), 2.11 (s, 3H); 3-methyl-5-bromo-2-aminobenzoic acid 1 H NMR (400MHz, DMSO-d 6 ): δ: 7.88(s, 1H), 7.45(s, 1H), 2.08(s, 3H).

[0066] (2) Synthesis of 3-methyl-5-cyano-2-aminobenzoic acid

[0067] ...

Embodiment 23

[0069] The synthesis of embodiment 23-chloro-2-hydrazinopyridine

[0070]

[0071] In a 500 ml round-bottomed flask, add 50 g of 2,3-dichloropyridine, 150 ml of ethanol, and 127 g of 80% hydrazine hydrate in sequence, heat and reflux and stir for 26 hours. After TLC monitors that the reaction is complete, the reaction system is cooled to room temperature , a solid precipitated, filtered, washed the filter cake with water, and dried to obtain needle-like white crystals with a yield of 90.13%.

Embodiment 3

[0072] Example 31-(3-chloropyridin-2-yl)-3-methylthiomethylene-N-(6-methyl-2-substituted carbamoyl-4-substituted phenyl)-1H-pyrazole - Preparation of 5-formamide

[0073] (1) Synthesis of 2,2-dimethyl-4-chloromethyl-1,3-dioxolane V

[0074]

[0075] In a 1000 ml round bottom flask, add 350 ml of acetone and 2.58 g of p-toluenesulfonic acid in turn, abbreviated as p-TsO for 1 hour. After stirring and dissolving, add 37.82 ml of 1-chloroglycerin dropwise. After the dropwise addition, stir at room temperature for 12 hours. , adding triethylamine to adjust the pH to neutral, then distilling off acetone under normal pressure, and distilling under reduced pressure to collect the fraction at 46-48 degrees Celsius / 1.7kPa to obtain a colorless transparent liquid with a yield of 65.36%; 1 H NMR (400MHz, CDCl 3 ( s, 1H), 1.35 (s, 1H).

[0076] (2) Synthesis of 2,2-dimethyl-4-methylene-1,3-dioxolane VI

[0077]

[0078] In a 500 ml round bottom flask, add 22.35 g of potassium t...

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Abstract

The invention provides a double amide derivative containing a sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing pyrazolecarboxamide and a preparing method and purpose thereof, and relates to double amide derivatives containing the pyrazolecarboxamide. The double amide derivative containing the pyrazolecarboxamide has a chemical structure general formula as shown in the map I. The structure general formula and the synthetic method of the double amide derivative and the purpose for being used as insecticides, antiseptics, a plant virus resistance agent and a plant activator are disclosed. The double amide derivative containing the sulfur ether and N-sulfur cayano (sulphone) imine structure and replacing the pyrazolecarboxamide can be mixed with auxiliaries or synergists which are acceptable in agriculture to form a processing technology to be used for preparing the insecticides, the antiseptics, the plant virus resistance agent and the plant activator. The invention further discloses the purpose and preparing method of the double amide derivative containing the sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing the pyrazolecarboxamide combining with commodity insecticides, commodity antiseptics, commodity plant virus resistance agents and commodity plant activators to be used for preventing and curing plant diseases, insect pests, virus diseases in agriculture, forestry and horticulture.

Description

technical field [0001] The technical solution of the present invention relates to pyrazole compounds, in particular to diamide derivatives containing pyrazole heterocycles. Background technique [0002] In recent years, bisamide compounds have developed into a new type of high-efficiency insecticides due to their novel structure, unique mechanism of action, high activity, and high safety to mammals, including phthaloxene Imide insecticides, the representative drug is flubendiamide (EP1006107) discovered by Japan Agricultural Chemical Company; Cytraniliprole (WO2004067528). The two types of compounds have different structures, but their mechanism of action is to act on the ryanodine receptors of insects, causing the continuous release of calcium ions in muscle and nerve tissue cells, resulting in continuous muscle contraction of insects, and finally the death of insects (Gerorge P. Lahm , Bioorganic & Medicinal Chemistry, 2009, 17: 4127-4133). [0003] Although bisamide in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D417/14A01N47/40A01N43/78A01N43/56A01P3/00A01P7/04A01P1/00
Inventor 范志金华学文李娟娟梁小文陈晓燕王根豪姬晓恬宗广宁李凤云周立峰
Owner NANKAI UNIV
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