Cyclic amino acid-containing diamide compound

A compound, cycloalkyl technology, applied in the field of insecticide active agent and pest control

Pending Publication Date: 2022-01-07
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compounds with excellent insecticidal activity have not been reported in this field

Method used

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  • Cyclic amino acid-containing diamide compound
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Examples

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preparation example Construction

[0139] The preparation method of the compound of the present invention

[0140] The diamide compounds containing cyclic amino acids of the present invention can be prepared by the following method, but the conditions of the method, such as reactants, solvents, bases, the amount of compounds used, reaction temperature, reaction time required, etc. are not limited to the following Explanation. The compounds of the present invention can also be conveniently prepared by combining various synthetic methods described in the specification or known in the art, and such combinations can be easily performed by those skilled in the art to which the present invention belongs.

[0141] The present invention synthesizes the diamide compounds containing cyclic amino acids represented by the general formulas (I)-(V), the preparation method is simple and easy, the operation is simple, the product is easy to purify, the cost is low, and the stability is improved. The diamide compound containin...

Embodiment 1

[0143] Embodiment 1: the preparation of 3-bromo-1-(3-chloropyridin-2-yl)-N-(1-(phenylcarbamoyl) cyclohexyl)-1H-pyrazole-5-carboxamide (compound I-1)

[0144] 1.1 Preparation of tert-butyl (1-(phenylcarbamoyl) cyclohexyl) carbamate

[0145]

[0146] 2.43g (10mmol) of 1-(tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid, 100mL of dichloromethane, 0.91g (9.5mmol) of aniline, 3.03g (30mmol) of triethyl Amine and 5.72 g (11 mmol) of benzotriazol-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate were sequentially added into a 250 mL three-necked flask. After reacting at room temperature for 4 h, 100 mL of water was added. The organic phase was separated off and the aqueous phase was extracted twice with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain 2.22 g of white solid with a yield of 73.5%.

[014...

Embodiment 2

[0158] Embodiment 2: Preparation of 3-bromo-1-(3-chloropyridin-2-yl)-N-(1-(phenylcarbamoyl)cyclopentyl)-1H-pyrazole-5-carboxamide ( Compound I-3)

[0159] 2.1 Preparation of tert-butyl (1-(phenylcarbamoyl) cyclopentyl) carbamate

[0160]

[0161] The synthesis of the target compound is similar to 1.1, except that the starting material is 1-(tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid instead of 1-(tert-butoxycarbonyl)amino)cyclohexane- 1-Carboxylic acid. The product is a white solid with a yield of 70.1%.

[0162]2.2 Preparation of 1-amino-N-phenylcyclopentane-1-carboxamide

[0163]

[0164] The synthesis of the target compound is similar to 1.2, except that the raw material is tert-butyl (1-(phenylcarbamoyl) cyclopentyl) carbamate instead of tert-butyl (1-(phenylcarbamoyl) Cyclohexyl) carbamate. The product is a yellow oily liquid with a yield of 98.3%. The next reaction was carried out directly without further treatment.

[0165] 2.3 Preparation of ...

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Abstract

The invention discloses a cyclic amino acid-containing diamide compound, a preparation method and application thereof, wherein the compound has a chemical structure as shown in a formula I described in the specification. The compound disclosed by the invention is used as an insecticide, especially has a good control effect on plutella xylostella, armyworm and the like, and is expected to become a novel insecticide.

Description

technical field [0001] The present invention relates to diamide compounds containing cyclic amino acids, to methods for preparing them, to their use as insecticide active agents, and to using these compounds and their compositions in agricultural, forestry, and gardening environments Methods and applications in pest control. Background technique [0002] Pests cause huge losses to agricultural production. Chemical pesticides are one of the effective means of integrated pest management. It has always been the demand and goal of plant protection workers to invent insecticides with high efficacy, environmental friendliness, unique mechanism of action, and no cross-resistance with existing pesticides. [0003] Patent US2005075372A1 discloses a diamide compound with insecticidal activity and its application. Among them, compound S1 has been developed as a commercial insecticide, the common name is chlorantraniliprole. [0004] [0005] Patent CN102924433A discloses a diami...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D409/14C07D405/14C07D401/14C07D231/16A01N43/56A01N53/12A01P7/04
CPCC07D401/04C07D409/14C07D405/14C07D401/14C07D231/16A01N43/56A01N53/00
Inventor 李忠陈睿嘉王俊杰冯婷婷董乐凤王港澳韩醴徐晓勇邵旭升
Owner EAST CHINA UNIV OF SCI & TECH
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