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Substituted pyrazole (sulphur) ketone compound and application thereof

A technology of ketone compounds and pyrazoles, which is applied in the fields of agricultural sterilization and pesticides, and can solve the problems that have not been reported in the literature.

Active Publication Date: 2013-03-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The substituted pyrazolone compound or substituted pyrazolethione compound developed by the present invention has a novel structure and has not been reported in the literature

Method used

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  • Substituted pyrazole (sulphur) ketone compound and application thereof
  • Substituted pyrazole (sulphur) ketone compound and application thereof
  • Substituted pyrazole (sulphur) ketone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Embodiment 1: the preparation of compound I-A-1

[0186]

[0187] Add pyrazolol (II-1, see CN 1906171A for preparation method) (6.3 grams, 30 mmoles), benzyl chloride (III-1) (7.3 grams, 30 mmoles), anhydrous potassium carbonate (6.5 g, 47 mmol) and 40 ml of dimethyl sulfoxide, heated to 90°C with stirring, kept the reaction for 6 hours, and removed most of the solvent under reduced pressure. The residue was poured into 100 ml of water, extracted with ethyl acetate (100 ml × 3), the organic layers were combined, washed with saturated aqueous sodium chloride (100 ml), dried with anhydrous magnesium sulfate, filtered, and desolvated under reduced pressure , column chromatography (ethyl acetate:petroleum ether=1:10) of the residue gave 3.3 g of white solid (compound I-A-1), yield 28.9%, melting point 216-218°C. NMR data 1H-NMR (300MHz, internal standard TMS, solvent CDCl3) is as follows:

[0188] δ (ppm): 3.16 (d, J=16.5, 1H), 3.35 (d, J=16.5, 1H), 3.41 (s, NCH3, 3H),...

Embodiment 2

[0190] Embodiment 2: the preparation of compound I-A-2

[0191]

[0192] Compound I-A-1 (3.8 g, 10 mmol), 20 ml of ethanol and 10 ml of 10% sodium hydroxide aqueous solution were sequentially added into the reaction flask, and the temperature was raised to reflux for reaction, and the reaction was monitored by TLC. Ethanol was removed under reduced pressure, 20 ml of water was added, and the pH value was adjusted to weak acidity with dilute hydrochloric acid, and 3 g of white solid (compound I-A-2) was obtained by filtration, with a yield of 81.8% and a melting point of 200-202°C.

Embodiment 3

[0193] Embodiment 3: the preparation of compound I-A-23

[0194]

[0195] Add compound I-A-2 (0.74 g, 2 mmol) and 20 ml of tetrahydrofuran successively to the reaction flask, slowly add carbonyldiimidazole (0.35 g, 2.2 mmol) under stirring, react at room temperature for 1 hour, slowly add 1 Milliliter of 25% methylamine aqueous solution was added, and the reaction was continued for 1 hour, and the reaction was monitored by TLC. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to obtain 0.3 g of a white solid with a yield of 39.5% and a melting point of 128-130°C. NMR data 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0196]δ(ppm): 2.78(d, J=5.1, NHCH 3 , 3H), 3.03(d, J=16.5, 1H), 3.36(s, NCH 3 , 3H), 3.43(d, J=16.5, 1H), 5.91(s, CH, 1H), 6.42(s, NH, 1H), 7.04(m, 1H), 7.27(m, 4H), 7.46(m , 2H), 7.70 (m, 1H).

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Abstract

The invention discloses a substituted pyrazole (sulphur) ketone compound, shown as a general formula I, wherein definitions of substitutional groups are described in the specification. The compound shown as the general formula I has broad-spectrum bactericidal activity and a good control effect on multiple germs such as cucumber downy mildew, wheat powdery mildew, corn rust disease, tomato late blight, cucumber gray mold, rice blast and cucumber anthracnose, especially has a good control effect on the cucumber downy mildew even dosage is lower; and part of the compound disclosed by the invention also has better insecticidal activity and can be used for preventing and controlling plutella xylostella and beet armyworm, so that the compound shown as the general formula I disclosed by the invention can be used for preparing bactericide and pesticide drugs used for preventing and controlling germs and insect pests in agriculture or other fields.

Description

technical field [0001] The invention belongs to the field of agricultural sterilization and insecticide. Specifically, it relates to a substituted pyrazole (thio) ketone compound and its application. Background technique [0002] The substituted pyrazolone compound or substituted pyrazolethione compound developed by the present invention has a novel structure and has not been reported in the literature. Contents of the invention [0003] The object of the present invention is to develop a substituted pyrazole (thio)one compound with novel structure and capable of effectively controlling harmful bacteria or pests, so as to provide a new fungicide or insecticide for agriculture or other fields. [0004] Technical scheme of the present invention is as follows: [0005] A pyrazolone or pyrazolethione compound, as shown in general formula I: [0006] [0007] In the formula: [0008] R 1 selected from hydrogen, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 3 -C ...

Claims

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Application Information

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IPC IPC(8): C07D231/54A01N43/56A01N43/84A01P3/00A01P7/04
Inventor 刘长令李淼李志念柴宝山宋玉泉孙旭峰王军锋梁博
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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