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4-(1H-pyrazol-1-yl) biphenyl formamide compound containing diphenyl ether group and application thereof

A technology of biphenylcarboxamide and phenoxyaniline, which is applied in the field of pesticide synthesis, can solve the problems of abnormal fallen leaves, dead plants and the like, and achieves the effects of simple preparation method, easily available raw materials and novel molecular structure.

Pending Publication Date: 2022-01-04
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Torreya trees aged more than 50 years, if infected with purple root rot, will not easily cause plant death, but abnormal leaves will appear; , some of the plants will wither in the same year or several years; the saplings of Chinese torreya or newly planted seedlings will die in a few months or in the same year after being infected with the purple root rot pathogen

Method used

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  • 4-(1H-pyrazol-1-yl) biphenyl formamide compound containing diphenyl ether group and application thereof
  • 4-(1H-pyrazol-1-yl) biphenyl formamide compound containing diphenyl ether group and application thereof
  • 4-(1H-pyrazol-1-yl) biphenyl formamide compound containing diphenyl ether group and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Preparation of 4-(1H-pyrazol-1-yl) biphenyl carboxamides containing diphenyl ether group:

[0034] 4-(1H-pyrazol-1-yl)benzonitrile (0.338g, 1.0mmol) was dissolved in 25mL (ethanol / water, volume ratio, 1:1), heated to 105°C for 16h under stirring, and the reaction solution was poured Pour into water, extract with ethyl acetate (30 mL), acidify the aqueous phase with 6.0 mol / L to pH = 5, precipitate a solid, filter with suction, and dry to give 4-(1H-pyrazol-1-yl)benzoic acid as a white solid, Yield 65%. 1 H NMR (600MHz, DMSO) δ13.13(s, 1H), 8.65(d, J=2.3Hz, 1H), 8.10(d, J=8.5Hz, 2H), 8.02(d, J=8.6Hz, 2H ),7.85(s,1H),6.63(s,1H). 13 C NMR (150MHz, DMSO) δ166.71, 142.73, 141.88, 130.94, 128.24, 128.15, 117.92, 108.63.

[0035]

[0036] Add 4-(1H-pyrazol-1-yl)benzoic acid (1.2mmol), 4-phenoxyaniline (1.0mmol), 1-ethyl-(3-dimethylaminopropyl) into a 25mL one-mouth bottle Carbodiimide hydrochloride (EDCI, 1.2mmol), 4-dimethylaminopyridine (DMAP, 0.2mmol) and CH 2 Cl 2...

Embodiment 2

[0038]

[0039] Add 4-(1H-pyrazol-1-yl)benzoic acid (1.2mmol), 4-(4-chlorophenoxy)aniline (1.0mmol), 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide hydrochloride (EDCI, 1.2mmol), 4-dimethylaminopyridine (DMAP, 0.2mmol) and CH 2 Cl 2 (10mL), stirred at 25°C for 2-5h. TLC monitored the complete reaction of the raw materials, and the reaction solution was filtered with suction. The obtained solid was purified by beating with petroleum ether to obtain compound I-2, a white solid, m.p.243-245°C, and the yield was 73%. 1 H NMR (600MHz, DMSO) δ10.83(s, 1H), 7.98(dd, J1=7.8Hz, J2=1.5Hz, 2H), 7.84(d, J=9.0Hz, 2H), 7.60-7.55(m ,4H),7.50(s,1H),7.44-7.41(m,2H),7.10-7.08(m,2H),7.03-7.02(m,2H).13C NMR(150MHz,DMSO)δ164.46,156.33,151.69 ,141.80,141.69,135.40,132.00,129.80,129.28,128.16,126.72,122.19,119.54,119.47,117.71,108.47.ESI-HRMS:m / zcalcd.for C22H17ClN3O2[M+0H.1f.1f.

Embodiment 3

[0041]

[0042] Add 4-(1H-pyrazol-1-yl)benzoic acid (1.2mmol), 4-(2-chlorophenoxy)aniline (1.0mmol), 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide hydrochloride (EDCI, 1.2mmol), 4-dimethylaminopyridine (DMAP, 0.2mmol) and CH 2 Cl 2 (10mL), stirred at 25°C for 2-5h. TLC monitored the complete reaction of the raw materials, and the reaction solution was filtered with suction. The obtained solid was purified by beating with petroleum ether to obtain compound I-3, a white solid, m.p.189-190°C, and the yield was 89%. 1 H NMR (600MHz, DMSO) δ10.32(s, 1H), 8.65(d, J=2.5Hz, 1H), 8.10(d, J=8.8Hz, 2H), 8.02(d, J=8.8Hz, 2H ),7.82-7.79(m,3H),7.60(dd,J1=8.0Hz,J2=1.5Hz,1H),7.38-7.35(m,1H),7.22-7.19(m,1H),7.06(dd, J 1 =8.2Hz,J 2 =1.4Hz,1H),7.01-6.99(m,2H),6.62-6.61(m,1H).13C NMR(150MHz,DMSO)δ164.65,161.01,154.87,152.12,141.69,130.70,129.21,128.77,128.14, 125.02, 122.16, 122.05, 120.34, 118.10, 117.70, 108.46. ESI-HRMS: m / zcalcd. for C22H17ClN3O2[M+H]+: 390.1009; found 390.1011.

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Abstract

The invention discloses a 4-(1H-pyrazole-1-yl) biphenyl formamide compound containing a diphenyl ether group and application thereof, the structural formula is shown in the specification, and in the structural formula, R group is one of 4-H, 4-Cl, 2-Cl and 4-OCH3. According to the application of the 4-(1H-pyrazol-1-yl) biphenyl formamide compound containing the diphenyl ether group to prevention and treatment of plant pathogenic fungi and oomycetes in forestry or agriculture, the activity result shows that the compound has a relatively good prevention and treatment effect on pecan dry rot pathogen and botrytis cinerea.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, and specifically relates to 4-(1H-pyrazol-1-yl)biphenylcarboxamide compounds containing diphenyl ether groups and their applications. Background technique [0002] In recent years, forestry fungal diseases have gradually developed resistance to previous commercial fungicide varieties, such as hickory dry rot fungus or Torreya root rot fungus, which has a certain impact on the production of forestry resources. The pathogen of hickory dry rot is Botryosphaeria dothidea, which is one of the pathogens that cause disease and even death of hickory trees. There are dozens of disease spots at most, and the most serious ones can reach hundreds of disease spots, which will have a serious impact on the growth and output of hickory nuts. The disease occurred from the end of March until November. The main targets of attack are hickory trees under 30-40 years old. Spread on the branches and branc...

Claims

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Application Information

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IPC IPC(8): C07D231/12A01N43/56A01P3/00
CPCC07D231/12A01N43/56Y02A50/30
Inventor 谷文杨子辉刘青松孙月王石发
Owner NANJING FORESTRY UNIV
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