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Diamide compound containing sydnone or sydnone imine and preparation and application of diamide compound

A compound and alkylene technology, which can be used as an active agent of pesticides to prevent and control pests, and can solve problems such as increased production costs and reduced yields

Pending Publication Date: 2020-06-12
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pest attack on growing crops as well as stored crops can lead to significantly lower yields, which in turn lead to increased production costs

Method used

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  • Diamide compound containing sydnone or sydnone imine and preparation and application of diamide compound
  • Diamide compound containing sydnone or sydnone imine and preparation and application of diamide compound
  • Diamide compound containing sydnone or sydnone imine and preparation and application of diamide compound

Examples

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preparation example Construction

[0064] The preparation method of the compound of the present invention

[0065] The compound represented by the general formula (I) of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactant, solvent, base, compound used, reaction temperature, reaction time required, etc. are not limited to the following explanations . The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

Embodiment 1

[0067] Example 1: (3-(2-(3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylbenzoyl )-Sydney ketimino)-N(6)-trifluoroacetamide preparation

[0068] 1.1 Preparation of 2-amino-5-chloro-3-methylbenzoyl chloride

[0069]

[0070] 5.568g (30mmol) of 2-amino-5-chloro-3-methylbenzoic acid, 100ml of dichloromethane, 23.8g (200mmol) of thionyl chloride and 3 drops of DMF were added to a 500ml single-necked flask successively , the temperature was raised to reflux for reaction, and after 3 hours of reaction, the solvent was suspended to obtain 5.8 g of a brown product with a yield of 95%. No further processing, proceed directly to the next step.

[0071] 1.2 Preparation of N-(1-cyanomethyl)-2-amino-5-chloro-3-methylbenzamide

[0072]

[0073] Add 2.775g (30mmol) of aminoacetonitrile hydrochloride, 10ml of tetrahydrofuran, 10ml of water, and 5.1g (60mmol) of sodium bicarbonate into a 250ml three-necked flask in sequence, and dropwise add 5.8g of 2 -Amino-...

Embodiment 2

[0086] Example 2: (3-(2-(3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylbenzoyl Preparation of )-Sydney ketimino)-N(6)-difluoroacetamide

[0087]

[0088] The synthesis of the target compound was similar to Example 1.6, except that trifluoroacetic acid was replaced by difluoroacetic acid. (Yield 52%, yellow solid). 1 H NMR (400MHz, CDCl 3 d) δ: 10.81(s,1H),8.61(m,1H),7.91(m,1H),7.80(s,1H),7.75(s,1H),7.71(m,1H),7.54(m, 1H),6.00(t,1H),6.68(s,1H),2.13(s,3H); HRMS(ESI)m / z[M+H] + C 21 h 13 BrN 7 o 4 Cl 2 f 3 , calculated value: 616.1732, measured value: 616.1736.

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Abstract

The invention discloses a diamide compound containing sydnone or sydnone imine and preparation and application of the diamide compound. The compound has a chemical structure shown as a formula I in the specification. The compound is used as an insecticide abd especially has a good control effect on armyworms, plutella xylostella, cotton bollworms, Asiatic corn borers and rice leaf folders and is expected to become a novel insecticide.

Description

technical field [0001] The present invention relates to diamide compounds containing Sydney ketone or Sydney ketimine, to methods for preparing them, to their use as active agents for pesticides, and to using these compounds and their compositions in agriculture, Methods and applications in pest control in forestry and horticultural environments. Background technique [0002] Plant diseases and insect pests are two major factors in the loss of agricultural production. Pest attack on growing crops as well as stored crops can lead to significantly lower yields, which in turn lead to increased production costs. [0003] Mesoionic compounds have a wide range of biological activities, such as insecticidal, bactericidal, anticancer and so on. Compounds with excellent insecticidal activity still need to be developed in this field. Contents of the invention [0004] The object of the present invention is to provide a class of diamide compounds containing Sydney ketone or Sydney...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/828A01P7/04
CPCC07D413/14A01N43/82
Inventor 钱旭红邵旭升杜少卿李忠徐晓勇
Owner EAST CHINA UNIV OF SCI & TECH