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Pyrazole carboxyl thiourea derivative and its preparation method and application

A technology of pyrazole carboxyl thiourea and its derivatives, which is applied in the field of pyrazole carboxyl thiourea derivatives and their preparation, and can solve the problems that the insecticidal activity of pyrazole carboxyl thiourea derivatives has not been disclosed.

Inactive Publication Date: 2011-12-14
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the preparation of some insecticidally active benzoylthiourea compounds has been reported (CN1040789), in the prior art, the preparation of pyrazoleformylthiourea derivatives as shown in the present invention and its insecticidal Activity not disclosed

Method used

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  • Pyrazole carboxyl thiourea derivative and its preparation method and application
  • Pyrazole carboxyl thiourea derivative and its preparation method and application
  • Pyrazole carboxyl thiourea derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation method of compound 01.

[0042] Step A: Preparation of 3-chloro-2-hydrazinopyridine

[0043]

[0044] Add 29.6g (0.2mol) of 2,3-dichloropyridine and 120g (1.92mol) of 80% hydrazine hydrate into a 250mL round bottom flask, heat to reflux for 5 hours, cool to room temperature, filter with suction, wash with ethanol, and dry to obtain 27.6g of white crystals, yield 96%, m.p.163-164°C.

[0045] Step B: Preparation of ethyl 1-(3-chloropyridin-2-yl)-3-pyrazolidinone-5-carboxylate

[0046]

[0047] Add 140mL of absolute ethanol to a 250mL three-necked flask, slowly add small pieces of sodium metal (4.83g, 0.21mol), heat to reflux after the reaction is complete, add 27g (0.19mol) of 3-chloro-2-hydrazinopyridine, and then Reflux for 10 minutes, slowly add 36.1 g (0.21 mol) of diethyl maleate dropwise, and then stir and reflux for 30 minutes after the dropping is completed, and after cooling to 65°C, neutralize the reaction mixture with 24 g (0.4 mol) of aceti...

Embodiment 2

[0067] Preparation method of compound 22.

[0068] Step A: Preparation of 1-(furan-2-yl)-4,4,4-trifluoro-1,3-butanedione

[0069]

[0070] Add 20mL of absolute ethanol to a 100mL round bottom flask, slowly add 0.81g (35mmol) of sodium metal, after the reaction is complete, add 3.1g (25mmol) of 2-acetylfuran dissolved in 20mL of absolute ethanol, and stir at room temperature for 1 hour , add 4.2g (30mmol) ethyl trifluoroacetate dropwise under ice bath, then reflux for 24 hours, cool, add 50mL water to dilute, acidify with hydrochloric acid, extract with ethyl acetate (25mL×3), combine the organic phases, and saturated saline After washing, drying with anhydrous sodium sulfate, and precipitation, the residue was subjected to column chromatography to obtain 4.21 g of a red liquid with a yield of 81.7%.

[0071] Step B: Preparation of 1-(3-chloropyridin-2-yl)-3-trifluoromethyl-5-(furan-2-yl)-1H-pyrazole

[0072]

[0073] In a 100mL round bottom flask, add 2.71g (13mmol) 1-(f...

Embodiment 3

[0084] Preparation method of compound 35.

[0085] Step A: Preparation of 3-methyl-2-amino-5-chlorobenzoic acid

[0086]

[0087] Add 10g (66mmol) of 3-methyl-2-aminobenzoic acid and 40mL of DMF into a 100mL three-necked flask, stir to dissolve the solid, then add 8.81g (66mmol) of NCS, heat the reaction solution to 100°C for 40 minutes, cool, Let stand overnight. The reaction solution was slowly poured into 150mL of ice water, the solid was precipitated, filtered with suction, washed with water, then dissolved in 250mL of ethyl acetate, filtered to remove insoluble matter, the filtrate was dried over anhydrous magnesium sulfate, desolvated under reduced pressure, and the residue was used After washing with ether, 8.6 g of a light brown solid was obtained, with a yield of 70.2%, m.p.197°C (decomposition).

[0088] 3-Methyl-2-amino-5-bromobenzoic acid was synthesized in a similar way using NBS as bromination reagent, a yellow solid with a yield of 86%, m.p.213-216°C.

[0...

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Abstract

The invention relates to a pyrazole formylthiourea derivative and a preparation method and an application thereof. Based on pyrazolecarboxamide compounds, an amide bridge is reconstructed into an acylthiourea bridge, and the obtained derivatives are shown in general formula I, wherein the definition of each substituent group in the formula is described in the description. Compounds of general formula I have excellent insecticidal activity, and can be used to prevent and control insect pest.

Description

technical field [0001] The invention belongs to the field of insecticides, and in particular relates to a pyrazole carboxylthiourea derivative, a preparation method and an application thereof. Background technique [0002] Pest control is very important in the realization of various industries such as agriculture, forestry, animal husbandry, sideline, fishery and public health. Due to the incorrect use of pesticides such as continuous abuse and excessive use all over the world, it has played a role in the selection of pests, and long-term accumulation has led to serious resistance of pests. As people pay more and more attention to environmental issues, scientists need to continue to conduct innovative research to develop new insecticides with high efficiency, low toxicity, safety and different modes of action. [0003] O-formamidobenzamide compounds are effective insecticides developed in recent years against Lepidoptera pests. Nippon Agricultural Chemicals, Bayer and DuPo...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D413/14A01N47/34A01P7/04
CPCA01N47/34C07D401/04C07D413/14
Inventor 李正名王宝雷张吉凤徐俊英熊丽霞赵毓王刚
Owner NANKAI UNIV
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