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Heterocyclicacyl iminethiazole compound as well as preparation method and application thereof

A kind of technology of heterocyclic acyl imino thiazole and compound, which is applied in the field of agricultural pesticides and can solve the problems of undisclosed heterocyclic acyl imino thiazole compounds and the like

Inactive Publication Date: 2017-06-09
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The prior art does not disclose the heterocyclic imide thiazole compound provided by the application

Method used

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  • Heterocyclicacyl iminethiazole compound as well as preparation method and application thereof
  • Heterocyclicacyl iminethiazole compound as well as preparation method and application thereof
  • Heterocyclicacyl iminethiazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxy-[4-methyl-3-(2,4,5-trifluorophenyl)-3H-thiazole-2-ylidene Preparation of ]-amide (Compound No. 24)

[0100] Step 1: Synthesis of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride

[0101]

[0102] Add 53.00g of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid and 72mL of thionyl chloride to a single-necked flask, raise the temperature until the system refluxes, cool after reflux for 2 hours, and evaporate at normal pressure Unreacted thionyl chloride. The temperature of the system is lowered to below 60°C, an anhydrous calcium chloride drying tower is connected externally, and the low-boiling impurities are evaporated under reduced pressure by a water pump to obtain a red viscous liquid, which solidifies into white crystals overnight. Yield 78.25%.

[0103] The NMR data of white crystals are: 1 H NMR (400MHz, CDCl 3 ),δ:3.95(s,3H,N-CH 3 ),6.97(t,J H-F =54.20Hz,1H,-CHF 2 ), 8.06 (s, 1H, pyrazolyl-H...

Embodiment 2

[0114] 2-[2-(3-Chloro-pyridine)]-5-fluoromethoxy-2H-pyrazole-3-carboxy-[4-methyl-3-(2-methyl-4-heptafluoroiso Preparation of propyl-phenyl)-3H-thiazol-2-ylidene]-amide (compound 70)

[0115]

[0116] With reference to the reaction steps in Example 1, 1-{2- [2-(3-Chloro-pyridine)]-5-fluoromethoxy-2H-pyrazole-3-carbonyl}-3-(2-methyl-4-heptafluoroisopropyl-phenyl)-sulfur Urea, then reacted with bromoacetone to obtain the target product 2-[2-(3-chloro-pyridine)]-5-fluoromethoxy-2H-pyrazole-3-carboxy-[4-methyl-3-( 2-Methyl-4-heptafluoroisopropyl-phenyl)-3H-thiazol-2-ylidene]-amide, yield: 65.2%.

Embodiment 3

[0118] 1-(4-Difluoromethoxy-phenyl)-5-isopropyl-1H-[1,2,3]triazole-4-carboxy-[3-(5-chloro-2-cyano- Preparation of phenyl)-4-methyl-3H-thiazol-2-ylidene]-amide (compound 169)

[0119]

[0120] Referring to the reaction steps in Example 1, using 1-(4-difluoromethoxy-phenyl)-5-isopropyl-1H-[1,2,3]triazole-4-carboxylic acid as raw material 1-(5-chloro-2-cyano-phenyl)-3-[1-(4-difluoromethoxy-phenyl)-5-isopropyl-1H-[1,2,3] Triazole-4-carbonyl]-thiourea, then reacted with bromoacetone to obtain the target product 1-(4-difluoromethoxy-phenyl)-5-isopropyl-1H-[1,2,3]tri Azole-4-carboxy-[3-(5-chloro-2-cyano-phenyl)-4-methyl-3H-thiazol-2-ylidene]-amide, yield: 66.3%.

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Abstract

The invention discloses a heterocyclicacyl iminethiazole compound as shown in a general molecular formula (I) (shown in the description), wherein various substituent groups are described in the description. The heterocyclicacyl iminethiazole compound disclosed by the invention has a novel structure, and is applicable to agricultural deinsectization.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, in particular to a heterocyclic imidethiazole compound. Background technique [0002] Facing the pressure of the environment, pesticides are in the period of variety renewal, and pesticides with high activity and good environmental compatibility are constantly replacing old varieties. Thiazole compounds have become one of the hot spots in the research and development of new pesticides because of their excellent biological activity and low toxicity. Many thiazole pesticides, such as fungicides thifluzamide, ethaboxam, insecticides clothianidin, thiamethoxam, and herbicides mefenacet , has played an important role in crop protection. Some 1,3-thiazolidine compounds have also attracted the attention of many pesticide chemists because of their good biological activity. At present, a variety of new active compounds with bactericidal, insecticidal and herbicidal effects have been successfully...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14A01N43/78A01N43/80A01P7/04
CPCC07D417/12A01N43/78A01N43/80C07D417/14
Inventor 朱冰春彭伟立袁静黄红英郁季平魏优昌孔小林陈杰
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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