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Pyridazinone compound and application thereof

A kind of compound, technology of pyridazinone, applied in pyridazinone compound and its application field, can solve the problem that structure pyridazinone compound has not been reported etc.

Active Publication Date: 2018-04-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the prior art, the structure of the pyridazinone compound shown in the general formula I of the present invention has not been reported

Method used

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  • Pyridazinone compound and application thereof
  • Pyridazinone compound and application thereof
  • Pyridazinone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0481] Example 1: Preparation of Compounds 15-21

[0482] 1) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole

[0483] Take 21.35g (0.1mol) of 2,4-dichlorophenylhydrazine hydrochloride and 16.4g (0.1mol) of 1,1,3,3-tetramethoxypropane in a 250ml three-necked flask, 100ml of 95% ethanol aqueous solution As a solvent, the temperature was raised to reflux for 3-5 hours. After the completion of the reaction monitored by TLC, most of the ethanol was evaporated under reduced pressure, sodium carbonate aqueous solution was added to the residual liquid, the aqueous phase was extracted with (3×100 ml) ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and desolvated . The residue was separated by column chromatography (the eluent was ethyl acetate and petroleum ether, the volume ratio was 1:10) to obtain 18.06 g of a yellow solid with a yield of 84.8%.

[0484] 2) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde

[04...

Embodiment 2

[0496] Example 2: Preparation of compound 74-1

[0497] 1) 2.89 g (0.02 mol) of phenylhydrazine hydrochloride and 3.28 g (0.02 mol) of 1,1,3,3-tetramethoxypropane were added to 50 ml of 95% ethanol. The temperature was raised to 80°C and refluxed, and the reaction was carried out for 3-6 hours. After TLC monitoring was completed, the solvent was evaporated under reduced pressure, and (3×50ml) ethyl acetate was added for extraction. The organic phase was washed with saturated brine 50ml. Chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90° C.), volume ratio is 1:6) to obtain 2.45 g of oily liquid with a yield of 85.0%.

[0498] 2) 7.3g (0.1mol) DMF was added to the there-necked flask of 250ml, after stirring in an ice-salt bath, 15.4g (0.1mol) phosphorus oxychloride was added dropwise, and 2.88g (0.02mol) N- Phenylpyrazole was heated to 100°C and refluxed, and reacted for 3-6 hours. After TLC monitoring was completed, the reaction solution was pour...

Embodiment 3

[0504] Example 3: Preparation of compound 124-3

[0505] 1) 4.29 g (0.02 mol) of 4,6-dichloropyridylhydrazine hydrochloride and 3.28 g (0.02 mol) of 1,1,3,3-tetramethoxypropane were added to 50 ml of 95% ethanol. The temperature was raised to 80°C and refluxed, and the reaction was carried out for 3-6 hours. After TLC monitoring was completed, the solvent was evaporated under reduced pressure, and (3×50ml) ethyl acetate was added for extraction. The organic phase was washed with saturated brine 50ml. Chromatography (the eluent is ethyl acetate and petroleum ether (boiling range 60-90° C.), the volume ratio is 1:6), to obtain 3.51 g of oily liquid with a yield of 82.0%.

[0506] 2) 7.3g (0.1mol) DMF was added to the there-necked flask of 250ml, after stirring under the ice-salt bath, 15.4g (0.1mol) phosphorus oxychloride was added dropwise, and 4.28g (0.02mol) 4.28g (0.02mol) was added dropwise after 1 h, 6-dichloropyridine-1H-pyrazole was heated to 100°C and refluxed, and rea...

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PUM

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Abstract

The invention discloses a pyridazinone compound. The pyridazinone compound has a general structural formula I. In the formula I, substituents are shown in the specification. The pyridazinone compoundhas broad-spectrum bactericidal effects, insecticidal and acaricidal activity and good effects of preventing and treating cucumber downy mildew, wheat powdery mildew, corn rust, rice blast, cucumber anthracnose and the like.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, in particular to a pyridazinone compound and application thereof. Background technique [0002] Pyridaben [Test code: NC-129, NCI-129 (both Nissan), BAS-300I (BASF), common name: pyridaben, trade name: Sanmite (Nissan), Agrimit (Sundat), Dinomite (Vapco), Pyromite (Mobedco), Tarantula (Baocheng)] reported by K.Hirata, etc., pyridazinone insecticides and acaricides developed by Nissan Chemical Industry Co., Ltd. [0003] [0004] Chemical name 2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one. The English chemical name is 2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one. The CAS accession number is [96489-71-3]. [0005] Applicable crops are citrus, tea, cotton, vegetables, pears, hawthorn and ornamental plants. Pyridaben is a pyridazinone insecticide and acaricide, non-systemic, at 5~20g / hL or 100~300kg / hm 2 It has excellent control effect on the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D401/14C07D403/14C07D409/14C07D417/14C07D405/14C07D413/14A01N43/58A01N43/78A01N43/66A01N43/60A01N43/80A01P3/00A01P7/02A01P7/04
CPCA01N43/58A01N43/60A01N43/66A01N43/78A01N43/80C07D401/14C07D403/12C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14
Inventor 刘长令关爱莹孙芹杨金龙李志念孙旭峰夏晓丽马森杨帆
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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