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Heterocyclic imide derivative containing bisamide structure and preparation method and application thereof

A technology for heterocyclic imines and derivatives, which is applied in the field of heterocyclic imine derivatives and their preparation, can solve the problems of serious cross-resistance, limited application space of chemical pesticides, proliferation of pest resistance problems, etc., and achieves easy availability of raw materials. , the preparation process is simple and easy, and the effect of broad application prospects

Active Publication Date: 2016-06-01
GUANGDONG ZHENGE BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the excessive and frequent use of conventional chemical pesticides has obviously led to a sharp increase in the problem of pest resistance, and the cross-resistance caused by the structural similarity between similar pesticide products is also quite serious, which limits the further application space of existing chemical pesticides

Method used

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  • Heterocyclic imide derivative containing bisamide structure and preparation method and application thereof
  • Heterocyclic imide derivative containing bisamide structure and preparation method and application thereof
  • Heterocyclic imide derivative containing bisamide structure and preparation method and application thereof

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Embodiment 1

[0031] The structural formula of part of the heterocyclic imine derivatives containing bisamide structure of the present invention is one of the specific compounds listed in Table 1:

[0032] Table 1: Representative compounds shown in structural formula I

[0033]

[0034]

Embodiment 2

[0036] Numbering is the preparation of the compound of I1 among the embodiment 1, and its reaction formula is:

[0037]

[0038] Its preparation method comprises the following steps:

[0039] 1) Using 5-methyl-1,3,4-oxadiazol-2(3H)-one (compound 1) and chloroacetone as starting materials to react under the condition of sodium hydroxide as base to obtain alkylation Intermediate 2a;

[0040] 2) Dissolve 10 mmol of the alkylation intermediate 2a in ethanol, add 12 mmol of hydrazine hydrate dropwise under stirring, slowly heat up to reflux after addition, continue the reaction, follow TLC until the reaction is complete, and obtain the heterocyclic intermediate after conventional post-treatment 3a;

[0041] 3) The heterocyclic intermediate 3a is deacetylated under acidic conditions to obtain the amino-substituted triazone heterocyclic intermediate 4a;

[0042] 4) Dissolve 10mmol of amino-substituted triazone heterocyclic intermediate 4a in 15mL of ethanol, add 10mmol of benza...

Embodiment 3

[0046] Numbering is the preparation of the compound of I10 among the embodiment 1, and its reaction formula is:

[0047]

[0048] Its preparation method comprises the following steps:

[0049] Steps 1) to 4) refer to Example 2 to obtain the imine intermediate 5aa;

[0050] 5) Weigh 2 mmol of imine compound 5aa, suspend it in 20 mL of anhydrous THF, then add 2.2 mmol of potassium tert-butoxide in batches, stir at room temperature for about 30 min, and then dropwise add 2.2 mmol of methyl chloroformate in THF Solution, dropwise, continue to stir the reaction, TLC traces the reaction is complete, add an appropriate amount of water to quench the reaction, use dichloromethane to extract three times, the organic phase is washed with brine and water, dried and concentrated to obtain the crude product, and then separated and purified by column chromatography to obtain the target product I10.

[0051] The physical and chemical properties of the target compound I10: 1 HNMR (CDCl ...

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Abstract

The invention discloses a heterocyclic imide derivative containing bisamide structure and a preparation method and application thereof. A structural formula of this derivative is shown as in the following formula I, and a preparation method of this derivative comprises subjecting 5-methyl-1,3,4-oxadiazol-2(3H)-one as a material successively to reactions such as alkylation, heterocyclization, hydrolysis, condensation and acylation to obtain the heterocyclic imide derivative containing bisamide structure, this derivative and its salts acceptable in pesticide science are significant in insecticidal activity, are widely applicable to the comprehensive prevention and control process of agricultural and forest pests and are insecticidal activity materials that are widely applicable.

Description

technical field [0001] The invention belongs to the technical field of organic medicine synthesis, and specifically refers to a heterocyclic imine derivative containing a bisamide structure and a preparation method and application thereof. Background technique [0002] The integrated control of agricultural diseases, insect pests and weeds is a major challenge faced by modern agriculture. As an important means of integrated pest management, pesticides play an irreplaceable role in agricultural production and are widely used in forestry, plant protection, aquatic products, Animal husbandry, sanitation pests and infectious disease prevention and control and other fields. With the increasing awareness of environmental protection and the orientation of China's agricultural development in the national 13th Five-Year Strategic Plan, it is required to implement comprehensive technology development for reducing chemical fertilizers and pesticides and increasing efficiency. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/06C07D401/12A01N43/707A01P7/04A01P7/02
CPCA01N43/707C07D253/06C07D401/12
Inventor 柯少勇杨自文张志刚王开梅梁英
Owner GUANGDONG ZHENGE BIOLOGICAL TECH CO LTD
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